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Maiden Holdings, Ltd.

mhld · NASDAQ Financial Services
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Ticker mhld
Exchange NASDAQ
Sector Financial Services
Industry Insurance - Specialty
Employees 51-200
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FY2022 Annual Report · Maiden Holdings, Ltd.
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UNITED STATES SECURITIES AND EXCHANGE COMMISSION 
Washington, D.C. 20549

FORM 10-K 

(Mark One)

☒

☐

ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

For the Fiscal Year Ended December 31, 2022

For the transition period from _________ to _________

Commission File Number: 001-34042

MAIDEN HOLDINGS, LTD.

(Exact Name of Registrant As Specified in Its Charter)

Bermuda
(State or Other Jurisdiction of Incorporation or Organization)

98-0570192
(I.R.S. Employer Identification No.)

94 Pitts Bay Road, 1st Floor
Pembroke HM 08, Bermuda
(Address of Principal Executive Offices and Zip Code)
(441) 298-4900
(Registrant’s Telephone Number, Including Area Code) 

Securities registered pursuant to Section 12(b) of the Act:

Title of Each Class

Trading symbol(s)

Name of Each Exchange on Which Registered

Common Shares, par value $0.01 per share

MHLD

NASDAQ Capital Market

Indicate by check mark if the registrant is a well-known seasoned issuer, as defined in Rule 405 of the Securities Act. Yes ☐ No ☒
Indicate by check mark if the registrant is not required to file reports pursuant to Section 13 or Section 15(d) of the Act. Yes ☐ No ☒
Indicate by check mark whether the registrant (1) has filed all reports required to be filed by Section 13 or 15(d) of the Securities Exchange Act of 1934 during the preceding 12
months (or for such shorter period that the registrant was required to file such reports), and (2) has been subject to such filing requirements for the past 90 days. Yes ☒ No ☐
Indicate by check mark whether the registrant has submitted electronically every Interactive Data File required to be submitted pursuant to Rule 405 of Regulation S-T during the
preceding 12 months (or for such shorter period that the registrant was required to submit such files). Yes ☒ No ☐
Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or an emerging growth company.
See the definitions of “large accelerated filer,” “accelerated filer,” “smaller reporting company” and "emerging growth company" in Rule 12b-2 of the Exchange Act.

Large Accelerated Filer
Non-Accelerated Filer

☐
☐

Accelerated Filer
Smaller Reporting Company
Emerging growth company

☒
☒
☐

If  an  emerging  growth  company,  indicate  by  check  mark  if  the  registrant  has  elected  not  to  use  the  extended  transition  period  for  complying  with  any  new  or  revised  financial
accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐
Indicate by check mark whether the registrant has filed a report on and attestation to its management’s assessment of the effectiveness of its internal control over financial reporting
under Section 404(b) of the Sarbanes-Oxley Act (15 U.S.C. 7262(b)) by the registered public accounting firm that prepared or issued its audit report. ☒
Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Act). Yes ☐ No ☒
The aggregate market value of the voting and non-voting common shares held by non-affiliates of the registrant as of June 30, 2022 (the last business day of the registrant’s most
recently completed second fiscal quarter) was approximately $134.3 million based on the closing sale price of the registrant’s common shares on the NASDAQ Capital Market on
that date.
As of March 8, 2023, 101,532,151 common shares were outstanding. 142,971,499 common shares, par value $0.01 per share, were outstanding when the ownership by our affiliate
Maiden Reinsurance Ltd. of 41,439,348 common shares were included. These affiliated shares are treated as treasury shares and are not included in the computation of consolidated
book value and earnings per common share.

DOCUMENTS INCORPORATED BY REFERENCE

Portions  of  the  registrant's  definitive  proxy  statement  to  be  filed  with  the  Securities  and  Exchange  Commission  pursuant  to  Regulation  14A  with  respect  to  the  annual  general
meeting of the shareholders of the registrant scheduled to be held on May 3, 2023 are incorporated by reference into Part III of this Annual Report on Form 10-K.

 
 
Business
Risk Factors
Unresolved Staff Comments
Properties
Legal Proceedings
Mine Safety Disclosures

MAIDEN HOLDINGS, LTD. 

TABLE OF CONTENTS

PART I

PART II

Market for Registrant’s Common Equity, Related Stockholder Matters and Issuer Purchases of Equity Securities
Management's Discussion and Analysis of Financial Condition and Results of Operation
Financial Statements and Supplementary Data
Changes in and Disagreements with Accountants on Accounting and Financial Disclosure
Controls and Procedures
Other Information

Directors, Executive Officers and Corporate Governance
Executive Compensation
Security Ownership of Certain Beneficial Owners and Management and Related Stockholder Matters
Certain Relationships and Related Transactions, and Director Independence
Principal Accounting Fees and Services

PART III

PART IV

Item 1.
Item 1A.
Item 1B.
Item 2.
Item 3.
Item 4.

Item 5.
Item 7.
Item 8.
Item 9.
Item 9A.
Item 9B.

Item 10.
Item 11.
Item 12.
Item 13.
Item 14.

Exhibits, Financial Statement Schedules
Form 10-K Summary

Item 15.
Item 16.
Signatures
Exhibits
Consolidated Financial Statements

Page

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E-1
F-1

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PART I

Special Note About Forward-Looking Statements

Certain statements in this Annual Report on Form 10-K, other than purely historical information, including estimates, projections, statements relating to our
business plans, objectives and expected operating results and the assumptions upon which those statements are based are forward-looking statements within the
meaning  of  the  Private  Securities  Litigation  Reform  Act  of  1995,  Section  27A  of  the  Securities  Act  of  1933,  as  amended,  and  Section  21E  of  the  Securities
Exchange Act of 1934, as amended. These forward-looking statements include general statements both with respect to us and the insurance industry and generally
are identified with the words "anticipate", "believe", "expect", "predict", "estimate", "intend", "plan", "project", "seek", "potential", "possible", "could", "might",
"may",  "should",  "will",  "would",  "will  be",  "will  continue",  "will  likely  result"  and  similar  expressions.  In  light  of  the  risks  and  uncertainties  inherent  in  all
forward-looking statements, the inclusion of such statements in this Annual Report on Form 10-K should not be considered as a representation by us or any other
person that our objectives or plans or other matters described in any forward-looking statement will be achieved. These statements are based on current plans,
estimates, assumptions and expectations. Actual results may differ materially from those projected in such forward-looking statements and therefore, you should
not place undue reliance on them. Important factors that could cause actual results to differ materially from those in such forward-looking statements are set forth
in Item 1A "Risk Factors" in this Annual Report on Form 10-K.

We  caution  that  the  list  of  important  risk  factors  is  not  intended  to  be  and  is  not  exhaustive.  We  undertake  no  obligation  to  update  or  revise  publicly  any
forward-looking statements, whether as a result of new information, future events or otherwise, except as may be required by law, and all subsequent written and
oral forward-looking statements attributable to us or individuals acting on our behalf are expressly qualified in their entirety by this paragraph. If one or more risks
or uncertainties materialize, or if our underlying assumptions prove to be incorrect, our actual results may vary materially from what we projected. Any forward-
looking statements in this Annual Report on Form 10-K reflect our current view with respect to future events and are subject to these and other risks, uncertainties
and assumptions relating to our operations, results of operations, growth, strategy and liquidity. Readers are cautioned not to place undue reliance on the forward-
looking statements which speak only as of the dates of the documents in which such statements were made.

References  in  this  Annual  Report  on  Form  10-K  to  the  terms  "we","us","our","the  Company"  or  other  similar  terms  mean  the  consolidated  operations  of
Maiden  Holdings,  Ltd.  and  our  consolidated  subsidiaries,  unless  the  context  requires  otherwise.  References  in  this  Annual  Report  on  Form  10-K  to  the  term
"Maiden Holdings" means Maiden Holdings, Ltd. only. References in this Annual Report on Form 10-K to $ are to the lawful currency of the United States, unless
otherwise indicated. Any discrepancies between the amounts included in Parts  I  and  II  discussions  in  this  Annual  Report  on  Form  10-K  and  the  consolidated
financial statements in Item 8 of this Annual Report on Form 10-K are due to rounding.

Risk Factor Summary

We  are  subject  to  various  risks  that  could  have  a  material  adverse  impact  on  our  financial  position,  results  of  operations  or  cash  flows.  The  following  is  a
summary of the principal factors that make investing in our securities risky and may cause our actual results to differ materially from forward-looking statements
included in this Annual Report on Form 10-K. The following is only a summary of the principal risks that may materially adversely affect our business, financial
condition, results of operations and cash flows and should be read in conjunction with the more complete discussion of the risk factors we face, which are set forth
in the section entitled “Risk Factors” in Part I, Item 1A. in this report:

• we have incurred volatile operating results in recent years and there can be no assurance that we will maintain operating profitability or return to

active underwriting on new prospective reinsurance risks;

• management  may  not  successfully  implement  its  business  strategy  which  could  result  in  a  decline  of  capital  or  adversely  affect  our  financial

condition or results of operations and may create enhanced risks;

•

•

•

our actual losses may be greater than our reserve for loss and loss adjustment expenses ("loss and LAE");

our  reinsurers  may  not  pay  losses  in  a  timely  fashion,  or  at  all,  which  could  have  a  material  adverse  effect  on  our  results  of  operations  or
financial condition;

the failure of any of the loss limitation methods we have employed or could employ in the future could have a material adverse effect on our
results of operations or financial condition;

• we depend on the policies, procedures and expertise of ceding companies for the business we have written in the past; these companies may
have  failed  to  accurately  assess  and  price  the  risks  they  have  underwritten,  which  may  lead  us  to  inaccurately  assess  and  price  the  risks  we
assumed;

•

•

the failure of our underwriting process and risk management could have an adverse effect on our results of operations or financial condition;

failure of our information technology systems or breaches to our technology systems as a result of cyber-attacks could disrupt our business and
adversely impact our profitability;

• we may not have sufficient unrestricted liquidity to meet our obligations and favorable terms to obtain additional capital may not be available;

1

•

•

•

a significant amount of our invested assets are subject to changes in interest rates and market volatility. If we are unable to realize our investment
objectives, our financial condition and results of operations may be adversely affected;

the determination of the fair values of our investments and whether a decline in the fair value of an investment is other-than-temporary are based
on management’s judgment and may prove to be incorrect;

our investments in alternative investments and our investments in joint ventures and/or entities accounted for using the equity method may be
illiquid and volatile in terms of value and returns, which could negatively affect our investment income and liquidity;

• we do not anticipate paying any cash dividends on our common shares for the foreseeable future;

• we may not be able to comply with restrictive covenants contained in the documents governing our Senior Notes or any future credit facility

which could trigger prepayment obligations;

•

•

•

compliance  by  our  insurance  subsidiaries  with  the  legal  and  regulatory  requirements  to  which  they  are  subject  is  expensive.  Any  failure  to
comply could have a material adverse effect on our business;

our  industry  is  highly  regulated,  the  regulatory  requirements  are  expensive  and  we  are  subject  to  significant  legal  restrictions  and  these
restrictions may have a material adverse effect on us;

our holding company structure and certain regulatory and other constraints affect our ability to pay dividends and make other payments;

• we have risks related to our Senior Notes;
• Maiden Reinsurance owns 29% of our total outstanding common shares and thus has a significant ownership and voting stake in our common

shares;

•

•

•

a few significant shareholders may influence or control the direction of our business. If the ownership of our common shares continues to be
highly concentrated, it may limit your ability and the ability of other shareholders to influence significant corporate decisions;

the market price for our ordinary shares has been and may continue to be highly volatile, and if there is a further sustained decline in our share
price there could be limited liquidity for our common shares;

provisions  in  our  bye-laws  could  change  voting  rights  of  our  shares,  impede  an  attempt  to  replace  or  remove  our  directors,  and/or  make  it
difficult for a third party to acquire us which could diminish the value of our common shares;

• we may not be able to attract and retain key employees or successfully implement our business strategy;

•

•

•

•

•

significant  changes  in  our  reinsurance  relationship  with  AmTrust  Financial  Services,  Inc.  ("AmTrust")  have  reduced  our  current  and  future
revenues and create significant uncertainty for sources of future liquidity;

our  initial  arrangements  with  AmTrust  were  negotiated  while  we  were  its  affiliate  and  as  such  the  arrangements  could  be  challenged  as  not
reflecting terms that we would agree to in arm’s-length negotiations with an independent third party;

our non-executive Chairman of the Board of Directors (the "Board") currently holds the positions of Chief Executive Officer and Chairman of
AmTrust. These dual positions may present, and make us vulnerable to, difficult conflicts of interest and related legal challenges;

the property and casualty insurance and reinsurance industry are cyclical in nature, which may affect our overall financial performance; and

new operating losses (and certain other tax attributes or tax benefits of the Maiden NA tax group) may be subject to limitation under Section 382
of the Tax Code.

2

Item 1. Business.

General Overview

Maiden  Holdings  is  a  Bermuda-based  holding  company.  We  create  shareholder  value  by  actively  managing  and  allocating  our  assets  and  capital,  including
through ownership and management of businesses and assets primarily in the insurance and related financial services industries where we can leverage our deep
knowledge of those markets. We also provide a full range of legacy services to small insurance companies, particularly those in run-off or with blocks of reserves
that are no longer core to those companies' operations, working with clients to develop and implement finality solutions including acquiring entire companies that
enable  our  clients  to  meet  their  capital  and  risk  management  objectives.  We  expect  our  legacy  solutions  business  to  contribute  to  our  active  asset  and  capital
management strategies.

We  are  not  currently  underwriting  reinsurance  business  on  new  prospective  risks  but  are  actively  underwriting  risks  on  a  retroactive  basis  through  Genesis
Legacy  Solutions,  LLC  ("GLS").  We  also  have  various  historic  reinsurance  programs  underwritten  by  our  wholly  owned  subsidiary  Maiden  Reinsurance  Ltd.
("Maiden Reinsurance") which are in run-off, including the liabilities associated with AmTrust Financial Services, Inc. ("AmTrust") which was terminated in 2019
as discussed in "Note 10 — Related Party Transactions" of the Notes to Consolidated Financial Statements included in Part II Item 8. "Financial Statements and
Supplementary Data". In addition, we have a Loss Portfolio Transfer and Adverse Development Cover Agreement ("LPT/ADC Agreement") with Cavello Bay
Reinsurance Limited ("Cavello") and a commutation agreement that further reduces our exposure to and limits the potential volatility related to AmTrust liabilities
in run-off, which are discussed in "Note 8 — Reinsurance" of the Notes to Consolidated Financial Statements included in Part II Item 8. "Financial Statements and
Supplementary Data".

Short-term income protection business is written on a primary basis by our wholly owned subsidiaries Maiden Life Försäkrings AB ("Maiden LF") and Maiden
General  Försäkrings  AB  ("Maiden  GF")  in  the  Scandinavian  and  Northern  European  markets,  each  with  branches  in  the  United  Kingdom  ("U.K.").  Insurance
support services are provided to Maiden LF and Maiden GF through our wholly owned subsidiary, Maiden Global Holdings Ltd. (“Maiden Global”), which is also
a licensed intermediary in the U.K. Maiden Global had previously operated internationally by providing branded auto and credit life insurance products through
insurer partners, particularly those in Europe and other global markets. These products also produced reinsurance programs which were underwritten by Maiden
Reinsurance.

Business Strategy

We continued to implement our revised operating strategy during 2022 which leverages the significant assets and capital we retain. In addition to restoring
operating  profitability,  our  strategic  focus  centers  on  creating  the  greatest  risk-adjusted  shareholder  returns,  in  order  to  increase  book  value  for  our  common
shareholders, both near and long-term. This strategy has three principal areas of focus:

•Asset management - investing in assets and asset classes in a prudent but expansive manner in order to maximize investment returns and is principally
enabled by limiting the amount of insurance risk we assume in relation to the assets we hold and maintaining required regulatory capital at very strong
levels to manage our aggregate risk profile;

•Legacy  underwriting  -  judiciously  building  a  portfolio  of  legacy  run-off  acquisitions  and  retroactive  reinsurance  transactions  which  we  believe  will
produce attractive underwriting returns; and

•Capital management - effectively managing the capital we hold on our balance sheet and when appropriate, repurchasing securities or returning capital to
enhance common shareholder returns.

Further  details  are  discussed  in  the  "Business  Strategy"  section  of  Item  7  "Management’s  Discussion  and  Analysis  of  Financial  Condition  and  Results  of

Operations - Overview" of this Annual Report on Form 10–K.

Strategic Developments in 2022

During 2022, we continued to advance each pillar of our business strategy and our book value increased by 7.7% to $2.80 per common share at December 31,
2022. We made significant progress in the capital management pillar of our business strategy, repurchasing additional preference shares and ultimately executing
an exchange of all of our outstanding preference shares for our common shares as discussed in the "Exchange of Preference Shares" section below. These capital
management measures produced gains of $115.5 million and were the single biggest driver of our increase in book value.

We also grew our alternative investment portfolio by 21% during 2022 and produced a positive return of 2.0% on that portfolio in a very challenging year in
the  global  financial  markets.  Despite  the  volatility  experienced  in  financial  markets  during  2022,  we  believe  our  alternative  investment  portfolio  remains  well
positioned to achieve its targeted longer-term returns. As interest rates continue to rise, we are increasingly focusing our investing activities on opportunities that
will  produce  current  income.  While  we  continued  to  develop  the  business  platform  of  GLS  during  2022,  a  disappointing  operating  loss  was  reported  as  new
reinsurance contracts did not perform to expectations.

The run-off of our historic reinsurance programs significantly underperformed during 2022, and we experienced adverse prior year reserve development of
$32.6 million which offset much of the positive progress made in our capital and asset management strategies. Finally, volatile financial markets and sharply rising
interest rates resulted in downward pressure on both our book value and earnings as investment results, including both realized and unrealized, were adversely
affected.

Exchange of Preference Shares

On  December  27,  2022  (the  "Exchange  Date"),  the  Company  exchanged  all  outstanding  8.250%  Non-Cumulative  Preference  Shares,  Series  A  (“Series  A
Preference Shares”), 7.125% Non-Cumulative Preference Shares, Series C (“Series C Preference Shares”) and 6.700% Non-Cumulative Preference Shares, Series
D (“Series D Preference Shares” and, together with

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the  Series  A  Preference  Shares  and  the  Series  C  Preference  Shares,  the  “Preference  Shares”)  for  newly  issued  common  shares,  $0.01  par  value  per  share  (the
“Exchange”). To effectuate the Exchange under the terms of each series of the Preference Shares, the affirmative vote of holders of two-thirds of the issued shares
of  each  series  of  Preference  Shares  was  required.  Maiden  Reinsurance,  which  owned  approximately  74%  of  each  series  of  the  Preference  Shares  immediately
preceding  the  Exchange  Date,  consented  to  the  variations  for  each  of  the  series  of  Preference  Shares  in  order  to  effectuate  the  Exchange.  The  Exchange  was
approved by a special committee of the Board of the Company consisting of disinterested directors and, upon advice of the special committee's financial advisor,
approved  the  conversion  ratio.  The  Board  subsequently  approved  the  conversion  ratio  and  the  Exchange.  Under  the  terms  of  the  Exchange,  preference
shareholders  received  common  shares  of  the  Company  having  a  fair  value  that  meets  the  “Minimum  Price”  as  determined  in  accordance  with  the  rules  of  the
Nasdaq  and  as  described  in  an  information  statement  that  the  Company  filed  with  the  Securities  and  Exchange  Commission  (the  “SEC”)  and  distributed  to
preference shareholders.

As of December 27, 2022, Maiden Reinsurance owns 29% of the Company's total outstanding common shares as described above, which is eliminated for
accounting and financial reporting purposes on the Company’s consolidated financial statements. The voting power of Maiden Reinsurance, with respect to its
investment in Maiden Holdings common shares, will be capped at 9.5% pursuant to the bye-laws of the Company. The Exchange and ownership of the common
shares by Maiden Reinsurance was made in compliance with Maiden Reinsurance's investment policy which has been approved by the Vermont Department of
Financial  Regulation  ("Vermont  DFR").  The  Vermont  DFR  additionally  specifically  approved  the  ownership  of  the  Company's  common  shares  by  Maiden
Reinsurance related to the Exchange.

The Company offered three common shares as consideration for each share of the Series A, C and D Preference Shares tendered. A total of 1,500,050 shares of
Series A Preference Shares, 1,744,028 shares of Series C Preference Shares, and 1,542,806 shares of Series D Preference Shares were accepted, resulting in the
issuance of 14,360,652 common shares to non-affiliates at a fair value of $28.4 million. The value of each Preference Share exchanged was equal to three times
the average closing price of Common Shares (as reflected on Nasdaq.com) for the five trading days immediately preceding the Exchange Date of December 27,
2022 which was $1.98. Such Common Shares are listed for trading on the NASDAQ Capital Market under the symbol “MHLD.”

As a result of the Exchange, the Preference Shares were delisted from and no longer trade on the New York Stock Exchange as of the Exchange Date. No
Preference Shares are issued or outstanding, and the Preference Shares were deregistered under the Securities Exchange Act of 1934, as amended. In addition, all
rights of the former holders related to ownership of the Preference Shares have been terminated.

Details of our recent capital transactions are also discussed in our Notes to the Consolidated Financial Statements in "Note 6 — Shareholders' Equity" included
under Item 8 "Financial Statements and Supplementary Data" of this Annual Report on Form 10–K. Our future results, and our ability to generate an improved
risk-adjusted return on capital, may be impacted by risks and trends set forth in Item 1A, "Risk Factors", and elsewhere in this Annual Report on Form 10-K.
Our Principal Operating Subsidiaries

Maiden Reinsurance, a wholly owned subsidiary of Maiden Holdings, is an affiliated reinsurance company licensed in the State of Vermont in the U.S. and our
principal operating subsidiary which commenced operations in June 2007. Effective March 16, 2020, we re-domesticated Maiden Reinsurance from Bermuda to
Vermont  in  the  U.S.,  having  determined  that  re-domesticating  Maiden  Reinsurance  to  Vermont  enables  us  to  better  align  our  capital  and  resources  with  our
liabilities, which originate mostly in the U.S., resulting in a more efficient structure. Maiden Reinsurance is subject to the statutes and regulations of Vermont in
the ordinary course of business. The re-domestication did not apply to Maiden Holdings which remains a Bermuda-based holding company. Maiden Reinsurance
owns 29% of the total outstanding common shares of Maiden Holdings and subject to our bye-laws, has the ability to vote up to 9.5% of these shares.

Maiden Holdings North America, Ltd. ("Maiden NA") is our wholly owned U.S. holding company and is domiciled in the State of Delaware.

Maiden Global, a wholly owned subsidiary of Maiden Holdings, operates as an insurance services company. Maiden Global is organized under the laws of
England  and  Wales.  Maiden  LF  and  Maiden  GF,  both  wholly  owned  subsidiaries  of  Maiden  Holdings,  are  insurance  companies  organized  under  the  laws  of
Sweden and write income protection insurance on a primary basis in the Scandinavian and Northern European market.

GLS was formed in November 2020 and is a wholly owned subsidiary of Maiden Reinsurance domiciled in the State of Delaware. GLS Services Company
(“GLS Services”) is a wholly owned subsidiary of GLS. GLS specializes in providing a full range of legacy services to small insurance entities, particularly those
in  run-off  or  with  blocks  of  reserves  that  are  no  longer  core  to  those  companies'  operations,  working  with  clients  to  develop  and  implement  finality  solutions
including acquiring entire companies that enable our clients to meet their capital and risk management objectives. Genesis Legacy Insurance Company (Vermont)
Limited, is a wholly owned subsidiary of GLS Services licensed in Vermont, and is the operating entity utilized by GLS to assume portfolios of legacy liabilities.
Our Reportable Segments

Our business currently consists of two reportable segments: Diversified Reinsurance and AmTrust Reinsurance. Our Diversified Reinsurance segment consists
of  a  portfolio  of  predominantly  property  and  casualty  insurance  and  reinsurance  business  focusing  on  regional  and  specialty  property  and  casualty  insurance
companies  located  primarily  in  Europe.  This  segment  now  also  includes  transactions  entered  into  by  GLS.  Our  AmTrust  Reinsurance  segment  includes  all
business ceded to Maiden Reinsurance by AmTrust, primarily the quota share reinsurance agreement (“AmTrust Quota Share”) between Maiden Reinsurance and
AmTrust’s  wholly  owned  subsidiary,  AmTrust  International  Insurance,  Ltd.  (“AII”)  and  the  European  hospital  liability  quota  share  reinsurance  contract
("European Hospital Liability Quota Share") with AmTrust’s wholly owned

4

subsidiaries AmTrust Europe Limited ("AEL") and AmTrust International Underwriters DAC ("AIU DAC"), which are both in run-off effective January 1, 2019.

Financial data relating to our two reportable segments is included in Item 7. "Management’s Discussion and Analysis of Financial Condition and Results of
Operations" and in "Notes to Consolidated Financial Statements - Note 3. Segment Information" included under Item 8 "Financial Statements and Supplementary
Data" of this Annual Report on Form 10-K.

The table below compares net premiums earned, by reportable segment, reconciled to the total consolidated net premiums earned for the years ended December

31, 2022 and 2021:

For the Year Ended December 31,

($ in thousands)
Diversified Reinsurance
AmTrust Reinsurance

Total

2022

2021

Net Premiums 
Earned

% of Total

Net Premiums 
Earned

% of Total

$

$

27,983 
9,749 
37,732 

74.2 % $
25.8 %
100.0  % $

27,681 
25,312 
52,993 

52.2 %
47.8 %
100.0 %

Financial data relating to the geographical areas in which we operate and relating to our principal products by line of business may be found in "Notes  to
Consolidated Financial Statements - Note 3. Segment Information" included under Item 8 "Financial Statements and Supplementary Data" of this Annual Report
on Form 10-K.

Diversified Reinsurance Segment

In this segment, Maiden Reinsurance previously wrote treaties on both a quota share basis and excess of loss basis outside the U.S. whereas Maiden LF and
Maiden  GF  write  business  within  Europe  on  a  primary  basis.  Net  premiums  written  by  our  Diversified  Reinsurance  segment  operating  subsidiaries,  excluding
intercompany reinsurance, for the years ended December 31, 2022 and 2021 included:

For the Year Ended December 31,

($ in thousands)
Maiden Reinsurance
Maiden LF
Maiden GF

Total

2022

2021

Net Premiums 
Written

% of Total

Net Premiums 
Written

% of Total

$

$

(332)
14,531 
9,421 
23,620 

(1.4)% $
61.5 %
39.9 %
100.0 % $

(1,031)
9,553 
7,576 
16,098 

(6.4)%
59.3 %
47.1 %
100.0 %

Please refer to Item 7. "Management’s Discussion and Analysis of Financial Condition and Results of Operations" for a discussion on the performance of our

Diversified Reinsurance segment for the years ended December 31, 2022 and 2021.

Maiden  Global’s  business  development  teams  partnered  with  automobile  manufacturers,  dealer  associations  and  local  primary  insurers  to  design  and
implement point of sale insurance programs which generated revenue for the auto manufacturer and insurance premiums for the primary insurer ("IIS business").
However, all of these programs are now in run-off and no new programs are being sought. With no new written premium, the only remaining earned premium is
from the Australian program that continued through 2022. The table below shows IIS premiums by line of business for the years ended December 31, 2022 and
2021:

For the Year Ended December 31,

2022

2021

($ in thousands)
Personal Auto - Quota Share Reinsurance
Credit Life - Insurance

Total

Net 
Premiums 
Written

$

$

(320)
23,944 
23,624 

% of Total

(1.4)% $

101.4 %
100.0 % $

Net 
Premiums 
Written

(4,592)
20,716 
16,124 

% of Total

(28.5)%
128.5 %
100.0 %

For the years ended December 31, 2022 and 2021, the Company's net premiums written for Personal Auto on a quota share reinsurance basis were negative. In
2022, negative premiums in Personal Auto were due to the refund of overpaid premium in a U.K. Auto quota share reinsurance program, and in 2021, the negative
premiums were due to the return of unearned premiums written in a German Auto quota share reinsurance contract in our IIS business which went into run-off on
January 1, 2021.

AmTrust Reinsurance Segment

General

AmTrust is a multinational specialty property and casualty insurance holding company with operations in the U.S., Europe and Bermuda. Effective January 1,
2019  (a)  the  AmTrust  Quota  Share,  and  (b)  the  European  Hospital  Liability  Quota  Share  were  terminated  on  a  run-off  basis.  These  transactions  are  broadly
referred  to  herein  as  the  "Final  AmTrust  QS  Terminations".  Apart  from  certain  unearned  premiums  in  the  AmTrust  Quota  Share  and  the  European  Hospital
Liability Quota Share that were earned subsequent to December 31, 2019, there was no new premium written within this segment during 2022 and 2021.

5

 
 
 
 
 
 
 
 
Information  relating  to  our  founding  shareholders  that  are  affiliated  with  AmTrust  ("Founding  Shareholders")  may  be  found  in  "Notes  to  Consolidated
Financial Statements - Note 10. Related Party Transactions" included under Item 8 "Financial Statements and Supplementary Data" of this Annual Report on
Form 10-K. Through our reinsurance agreements with AmTrust, we reinsured specific lines of business within the following AmTrust business segments:

• Small  commercial  business  insurance,  which  includes  U.S. workers’  compensation,  commercial  package  and  other  low-hazard  property  and  casualty

insurance products;

• Specialty risk and extended warranty coverage for consumer and commercial goods and custom designed coverages, such as accidental damage plans and
payment protection plans offered in connection with the sale of consumer and commercial goods, in the U.S., U.K. and certain other global markets and
European hospital liability; and

• Specialty program which includes package products, general liability, commercial auto liability, excess and surplus lines programs and other specialty

commercial property and casualty insurance to a narrowly defined, homogeneous group of small and middle market companies.

AmTrust Quota Share

Under the AmTrust Quota Share with AII, effective July 1, 2007 and through 2018, we reinsured 40% of AmTrust’s premium written, net of reinsurance with
unaffiliated reinsurers, relating to all lines of business that existed on the effective date. We also had the option to reinsure additional programs, in addition to the
original lines of business entered into by AmTrust since the effective date of the AmTrust Quota Share. As AmTrust expanded into new lines of business, pursuant
to the terms of the AmTrust Quota Share, we had selectively added some of those lines and opted not to participate in others. Consequently our share of AmTrust's
overall gross premiums written declined below 40% over time.

As a result of the Final AmTrust QS Terminations described above, our active reinsurance contracts with AmTrust were terminated effective January 1, 2019.
Also,  effective  July  31,  2019,  Maiden  Reinsurance  and  AII  entered  into  a  Commutation  and  Release  Agreement  (which  is  broadly  referred  to  herein  as  the
"AmTrust WC Commutation") effective July 31, 2019, which provided for AII to assume all reserves ceded by AII to Maiden Reinsurance with respect to its
proportional 40% share of the ultimate net loss under the AmTrust Quota Share related to: (a) all losses incurred in Accident Year 2017 and Accident Year 2018
under California workers' compensation policies and as defined in the AmTrust Quota Share ("Commuted California Business"); and (b) all losses incurred in
Accident Year 2018 under New York workers' compensation policies ("Commuted New York Business" and together with the Commuted California Business,
"Commuted  Business")  in  exchange  for  the  release  and  full  discharge  of  Maiden  Reinsurance  of  all  of  its  obligations  to  AII  with  respect  to  the  Commuted
Business. The Commuted Business did not include any business classified by AII as Specialty Program or Specialty Risk business.

European Hospital Liability Quota Share

On  April  1,  2011,  Maiden  Reinsurance  entered  into  the  European  Hospital  Liability  Quota  Share  with  AEL  and  AIU  DAC  to  cover  those  entities'  medical
liability business within Europe, primarily in Italy and France. These contracts were terminated on a run-off basis effective January 1, 2019 as part of the Final
AmTrust QS Terminations. For more information, please refer to "Notes to Consolidated Financial Statements - Note 10. Related Party Transactions" included
under Item 8 "Financial Statements and Supplementary Data" of this Annual Report on Form 10-K.

Risk Management

Our  Enterprise  Risk  Management  ("ERM")  framework  reflects  the  ‘three  lines  of  defense’  approach  to  risk  management,  which  involves  (1)  individual
functions  having  responsibility  for  identifying  and  managing  risks;  (2)  the  ERM  Committee  providing  oversight  and  guidance  to  individual  functions;  and  (3)
internal  audit  performing  independent  reviews.  Our  Board  has  overall  responsibility  for  oversight  of  the  ERM  program  and  has  delegated  this  oversight  to  its
Audit Committee.

Our  ERM  Committee  (comprised  of  our  Co-Chief  Executive  Officers  and  most  other  senior  members  of  management)  monitors  and  oversees  the  risk
environment and provides direction to mitigate, to an acceptable level, the most significant and material risks that may adversely affect our ability to achieve our
goals.  The  ERM  Committee  continually  reviews  factors  that  may  impact  our  organizational  risk  and  develops  and  implements  strategies  and  action  plans  to
mitigate key risks.

Our ERM program is designed to achieve the following:

• Establish a process to assess strategies and business decisions on a risk/reward basis;

• Establish a risk governance structure with clearly defined roles and responsibilities;

•

Identify and assess all material risks from internal and external sources;

• Manage risks within our risk appetite; and

• Effective review and reporting of major loss events.

The  first  line  of  defense  assists  with  the  identification  of  risks,  creation  of  appropriate  responses  to  risks,  and  maintains  them  within  the  risk  appetite  and
tolerances  that  the  ERM  Committee  believes  are  necessary  to  achieve  our  business  strategies  and  objectives.  The  mitigation  of  risks  is  achieved  through  the
application and operation of controls, transferring of risk or tolerating risks within risk appetite.

Our internal audit department assesses the adequacy and effectiveness of our risk management framework and mitigating controls and coordinates risk-based
audits to evaluate and address risk within targeted areas of our business. The core functions of this department are to (1) assess the adequacy and effectiveness of
our internal control systems; (2) coordinate risk-based

6

audits and compliance reviews; and (3) carry out other initiatives to evaluate and address risk within targeted areas of our business. Internal audit integrates testing
of the risk management framework into its annual test plans.

Our Audit Committee, comprised solely of independent directors, meets at least quarterly to assess whether management is addressing risk issues in a timely
and appropriate manner. The Audit Committee receives a quarterly update on capital and risk management. Our risk appetite and tolerances have been formally
approved by the Audit Committee.

As a property and casualty holding company, our insurance subsidiaries are in the business of assuming risk. We are not currently underwriting reinsurance

business on prospective risks as we historically have, but are now actively underwriting risks on a retroactive basis. Our primary risks are categorized as follows:

• Strategic risk – the risk that strategic decisions have an unexpected or adverse impact on future earnings or capital adequacy. This includes the ability to

deploy capital in order to maximize risk adjusted returns in the most efficient way, without adversely impacting the adequacy of our capital position;

• Insurance risk - the risk that insured losses are higher than our expectations. This includes losses arising from inadequate loss reserves, losses from larger
than  expected  non-catastrophe  current  accident  year  losses,  and  catastrophe  losses  that  exceed  our  expectation  or  our  reinsurance  limits.  Maiden
Reinsurance is not engaged in active reinsurance underwriting on prospective risks and as a result our insurance risk from premiums is immaterial;

• Investment risk - the risk of loss in our investment portfolio potentially caused by fluctuations in interest rates, credit spreads, foreign exchange rates and

inflation on both assets and liabilities;

• Liquidity risk - the risk that the group does not have sufficient unrestricted or liquid funds to pay losses or meet contractual obligations as they become

due; and

• Operational risk - the risk of loss from inadequate or failed internal processes, people, systems and/or external events (i.e. cyber), which also includes legal

risks.

Reserve for Loss and LAE

General

We are required by applicable insurance laws and regulations in the U.S. and Sweden and by U.S. Generally Accepted Accounting Principles ("U.S. GAAP")
to establish loss reserves to cover our estimated liability for the payment of all loss and LAE incurred with respect to premiums earned on the policies and treaties
that we write. These reserves are balance sheet liabilities presenting estimates of loss and LAE which we are ultimately required to pay for insured or reinsured
claims that have occurred as of or before the balance sheet date. The loss and LAE reserves on our balance sheet represent management’s best estimate of the
outstanding  liabilities  associated  with  our  premium  earned.    In  developing  this  estimate,  management  considers  the  results  of  internal  and  external  actuarial
analyses,  trends  in  those  analyses  as  well  as  industry  trends.  Our  opining  independent  actuary  certifies  that  the  reserves  established  by  management  make  a
reasonable provision for our unpaid loss and LAE obligations.

These amounts include case reserves and provisions for Incurred But Not Reported ("IBNR") reserves. Case reserves are established for losses that have been
reported to us, and not yet paid. IBNR reserves represent the estimated cost of losses that have occurred but have not been reported to us and include a provision
for  additional  development  on  case  reserves.  We  establish  case  reserves  based  on  information  from  the  ceding  company,  reinsurance  intermediaries,  and  when
appropriate,  consultations  with  independent  legal  counsel.  The  IBNR  reserves  are  established  by  management  based  on  reported  loss  and  LAE  and  actuarially
determined estimates of ultimate loss and LAE.

A variety of standard actuarial methods are calculated to estimate ultimate loss and LAE. The majority of our business is reserved individually by cedant and
line of business, with the remainder reserved in homogeneous groupings. Ultimate loss selections are accumulated across the reserve segments, and appropriate
actuarial judgment is applied to determine the final selection of estimated ultimate losses. Ultimate losses are converted to IBNR reserves by subtracting inception
to date paid losses and case reserves from those amounts. The combined total of case and IBNR results in indicated reserves which are the basis for the carried
reserves for financial statements. Ultimate losses are also used to estimate premium and commission accruals for accounts with adjustable features.

Loss reserves do not represent an exact calculation of liability; rather, loss reserves are estimates of what we expect the ultimate resolution and administration
of claims will cost. These estimates are based on actuarial and statistical projections and on our assessment of currently available data, as well as estimates of
trends in claims severity and frequency, judicial theories of liability and other factors. Loss reserve estimates are refined as experience develops and as claims are
reported  and  resolved.  Establishing  an  appropriate  level  of  loss  reserves  is  an  inherently  uncertain  process.  In  addition,  the  relatively  long  reporting  periods
between when a loss occurs and when it may be reported to our claims department for our casualty lines of business also increase the uncertainties of our reserve
estimates in such lines. To assist us in establishing appropriate reserves for loss and LAE, we analyze a significant amount of internal data and external insurance
industry information with respect to the pricing environment and loss settlement patterns. In combination with our individual account pricing analyses and our
internal loss settlement patterns, this industry information is used to guide our loss and LAE estimates. These estimates are reviewed quarterly, at a high level of
detail, and any adjustments are reflected in earnings in the periods in which they are determined.

For additional information concerning our reserves, see Item 7,"Management’s Discussion and Analysis of Financial Condition and Results of Operations —
Critical Accounting Policies — Reserve for Loss and LAE" and "Notes to Consolidated Financial Statements - Note 9 — Reserve for Loss and Loss Adjustment
Expenses" included under Item 8 "Financial Statement and Supplementary Data", for further information regarding the specific actuarial models we utilize and
the uncertainties in establishing the reserve for loss and LAE.

7

Our Financial Strength Rating

We currently do not have a financial strength rating from any of the major rating agencies that cover our industry. A.M. Best has developed a rating system to
provide  an  opinion  of  an  insurer’s  or  reinsurer’s  financial  strength  and  ability  to  meet  ongoing  obligations  to  its  policyholders.  Each  rating  reflects  that  rating
agency’s independent opinion of the capitalization, management and sponsorship of the entity to which it relates, and is neither an evaluation directed to investors
in  our  common  shares  nor  a  recommendation  to  buy,  sell  or  hold  our  common  shares.  A.M.  Best  maintains  a  letter  scale  rating  system  ranging  from  "A++"
(Superior) to "F" (In Liquidation).

As presently constituted, we believe that our current business operations neither require a financial strength rating nor inhibit us from pursuing or achieving
our strategic objectives. However, as we continue to evaluate our ongoing business strategy, the lack of a financial strength rating from one of the major rating
agencies may limit or negatively impact our ability to market and sell our products in the future. It may also require us to use collateral more frequently to secure
client relationships, which could impact our unrestricted liquidity. Both of these factors would be key considerations as to whether and when we would resume
active underwriting of new prospective risks.

Our Employees

On  March  8,  2023,  we  had  approximately  49  full-time  and  part-time  employees  who  are  located  in  Bermuda,  the  U.S.,  the  U.K.,  Germany,  Ireland  and

Sweden. We believe that our employee relations are good. None of our employees are subject to collective bargaining agreements.

Regulatory Matters

General

The insurance and reinsurance industry are subject to regulatory and legislative oversight and regulation in various markets in which we operate.

U.S. Insurance Regulation

Maiden  Reinsurance  is  an  affiliated  reinsurer  organized  under  the  laws  of  Vermont.  Regulatory,  supervisory  and  administrative  authority  over  insurance
companies in the United States is primarily delegated to the states with the exception of federal authority over boycott, coercion and intimidation, federal antitrust
laws and where federal law is enacted specifically to regulate the business of insurance. Among other things, state insurance departments regulate insurer solvency
standards, insurer and agent licensing, authorized investments, loss and loss expense reserves and provisions for unearned premiums, and deposits of securities for
the  benefit  of  policyholders.  Maiden  Reinsurance  is  required  to  file  detailed  financial  statements  and  other  reports  with  the  Vermont  DFR.  These  financial
statements are subject to the supervision, regulation and periodic examination by the Vermont DFR.

State Insurance Department Examinations

Maiden Reinsurance is subject to the financial supervision and regulation of the Vermont DFR. As part of their regulatory oversight process, state insurance
departments conduct periodic detailed examinations of the financial reporting of insurance companies domiciled in their states, generally not less frequently than
once  every  five  years.  Examinations  may  be  carried  out  in  cooperation  with  the  insurance  departments  of  other  states  under  guidelines  promulgated  by  the
National Association of Insurance Commissioners ("NAIC").

Statutory Accounting Principles

Statutory  accounting  principles  ("SAP")  are  a  basis  of  accounting  developed  to  assist  insurance  regulators  in  monitoring  and  regulating  the  solvency  of
insurance  companies.  SAP  is  primarily  concerned  with  measuring  an  insurer's  surplus  to  policyholders.  Accordingly,  statutory  accounting  focuses  on  valuing
assets and liabilities of insurers at financial reporting dates in accordance with appropriate insurance law and regulatory provisions applicable in each insurer's
domiciliary state.

U.S. GAAP is concerned with a company's solvency, but is also concerned with other financial measurements, principally income and cash flows. Accordingly,
U.S. GAAP gives more consideration to appropriate matching of revenue and expenses and accounting for management's stewardship of assets than does SAP. As
a direct result, different assets and liabilities and different amounts of assets and liabilities will be reflected in financial statements prepared in accordance with
U.S. GAAP compared to SAP. Statutory accounting practices established by the NAIC and adopted in part by Vermont will determine, among other things, the
amount of statutory surplus and statutory net income of Maiden Reinsurance, and thus determine, in part, the amount of funds that could be available to pay as
dividends.

Holding Company Regulation

Maiden Reinsurance is subject to the U.S. statutory holding company laws of Vermont. The insurance holding company laws and regulations apply directly to
individual insurers, indirectly to non-insurance entities, and provide regulators the ability to look at any entity within an insurance holding company system (or
group). State regulations generally provide that each insurance company in an insurance holding company system must register with the insurance department of
its state of domicile. These laws vary from state to state, but each state has enacted legislation which requires licensed insurers that are subsidiaries of insurance
holding companies to register and file with state regulatory authorities certain reports including information concerning their capital structure, ownership, financial
condition and general business operations. All transactions involving the insurers in a holding company system and their affiliates must be fair and reasonable and
often require prior notice and non-disapproval by the state insurance department of their domicile. Further, state insurance holding company laws typically place
limitations on the amounts of dividends or other distributions payable by insurers. Any capital distribution of

8

any kind out of Maiden Reinsurance would be done consistent with Vermont regulations or as required, with the prior approval of the Vermont DFR.

State  insurance  holding  company  laws  also  require  prior  notice  and  state  insurance  department  approval  of  changes  in  control  of  an  insurer  or  its  holding
company. "Control" is generally defined as the possession, direct or indirect, of the power to direct or cause the direction of the management and policies of the
company, whether through the ownership of voting securities, by contract (except a commercial contract for goods or non-management services) or otherwise.
Maiden Reinsurance is domiciled in Vermont where any beneficial owner of 10% or more of the outstanding voting securities of an insurance company or its
holding company is presumed to have acquired control, unless this presumption is rebutted. Therefore, an investor who intends to acquire beneficial ownership of
10% or more of our outstanding voting securities may need to comply with these laws and would be required to file notices and reports with the Vermont DFR and
receive approval from the Vermont DFR or rebut the presumption of control before such acquisition.

As of December 27, 2022, Maiden Reinsurance owns 29% of the Company's total outstanding common shares as described above, which is eliminated for
accounting and financial reporting purposes on the Company’s consolidated financial statements. The voting power of Maiden Reinsurance, with respect to its
common shares, will be capped at 9.5% pursuant to the bye-laws of the Company. The Exchange and ownership of the common shares by Maiden Reinsurance
was made in compliance with Maiden Reinsurance's investment policy which has been approved by the Vermont DFR. The Vermont DFR additionally specifically
approved the ownership of the Company's common shares by Maiden Reinsurance related to the Exchange.

Additionally,  the  NAIC  Model  Holding  Company  Act  and  NAIC  Model  Holding  Company  Regulation  address  “enterprise”  risk  -  the  risk  that  an  activity,
circumstance, event, or series of events involving one or more affiliates of an insurer that, if not remedied promptly, is likely to have a material adverse effect upon
the financial condition or liquidity of the insurer or its insurance holding company system as a whole. The Vermont DFR adopted the requirement for a holding
company to annually submit an Enterprise Risk Report with the state commissioner. In addition, under the NAIC Model Holding Company Act, as adopted in
Vermont, any person divesting control (10% or more ownership) over an insurer must provide 30 days’ notice to the regulator and the insurer. After receipt of the
notice, the Vermont Insurance Commissioner must determine whether the parties seeking to divest or to acquire a controlling interest will be required to file for or
obtain approval of the transaction. That law may discourage potential acquisition proposals and may delay, deter or prevent an acquisition of control of a direct or
indirect parent of the Company (including Maiden Holdings) (in particular through an unsolicited transaction), even if the shareholders of such parent consider
that transaction to be desirable.

In 2012, the NAIC adopted the Risk Management and Own Risk and Solvency Assessment (“ORSA”) Model Act (the “ORSA Model Act”), which requires
domestic insurers to maintain a risk management framework and establishes a legal requirement for domestic insures to conduct an ORSA in accordance with
NAIC’s ORSA Guidance Manual. The ORSA Model Act provides that domestic insurers, or their insurance group, must regularly conduct an ORSA consistent
with a process comparable to the ORSA Guidance Manual process. The ORSA Model Act also provides that, no more than once a year, an insurer's domiciliary
regulator may request that an insurer submit an ORSA summary report, or any combination of reports that together contain the information described in the ORSA
Guidance Manual, with respect to the insurer and/or the insurance group of which it is a member. Vermont has adopted its version of the ORSA Model Act and the
Company believes that a Vermont statutory exemption (8 V.S.A. Section 3586) presently exempts the Company from the requirements of Vermont’s version of the
ORSA Model Act, because the Company’s and its group’s annual direct written and unaffiliated assumed premium are less than the applicable threshold.

Vermont also adopted the NAIC’s Corporate Governance Annual Disclosure Model Act ("CGAD"). CGAD requires an annual filing by an insurer or insurance
group  that  provides  detailed  information  regarding  their  governance  practices  as  well  as  sample  documentation  on  their  corporate  governance  structure  and
policies.

Risk-Based Capital

U.S. insurers are also subject to risk-based capital ("RBC") guidelines that provide a method to measure the total adjusted capital (statutory capital and surplus
plus other adjustments) of insurance companies taking into account the risk characteristics of a company's investments and products. The RBC formulas establish
capital  requirements  for  four  categories  of  risk:  asset  risk,  insurance  risk,  interest  rate  risk  and  business  risk.  For  each  category,  the  capital  requirement  is
determined by applying factors to asset, premium and reserve items, with higher factors applied to items with greater underlying risk and lower factors for less
risky items. Insurers that have less statutory capital than the RBC calculation required are considered to have inadequate capital and are subject to varying degrees
of regulatory action depending upon the level of capital inadequacy. Maiden Reinsurance filed its latest RBC reports in March 2023 for the 2022 calendar year,
and the reported RBC levels exceed Vermont's RBC requirements. Maiden Reinsurance continues to invest excess capital pursuant to our current business strategy
as our RBC requirements permit.

Reinsurance

The  ability  of  an  insurer  to  take  credit  for  the  reinsurance  purchased  from  reinsurance  companies  is  a  significant  component  of  reinsurance  regulation.
Typically, an insurer will only enter into a reinsurance agreement if it can obtain credit to its reserves on its statutory financial statements for the reinsurance ceded
to the reinsurer. With respect to U.S. domiciled reinsurers that reinsure U.S. insurers, credit is usually granted when the reinsurer is licensed, certified or accredited
in a state where the primary insurer is domiciled or, in some instances, in a state in which the primary insurer is licensed. States also generally permit primary
insurers to take credit for reinsurance if the reinsurer is (i) domiciled in a state with a credit for reinsurance law that is substantially similar to the standards in the
primary  insurer's  state  of  domicile,  and  (ii)  meets  certain  financial  requirements.  Credit  for  reinsurance  purchased  from  a  reinsurer  that  does  not  meet  the
foregoing  conditions  is  generally  allowed  to  the  extent  that  such  reinsurer  secures  its  obligations  with  qualified  collateral.  We  are  able  to  take  credit  for  all
reinsurance purchased and all cedants are able to take credit for reinsurance they purchase from us.

9

NAIC Ratios

The NAIC Insurance Regulatory Information System ("IRIS") was developed to help state regulators identify companies that may require special attention.
IRIS is comprised of statistical and analytical phases consisting of key financial ratios whereby financial examiners review annual statutory basis statements and
financial ratios. Each ratio has an established "usual range" of results and assists state insurance departments in executing their statutory mandate to oversee the
financial condition of insurance companies. A ratio result falling outside the usual range of IRIS ratios is not considered a failing result; rather unusual values are
viewed as part of the regulatory early monitoring system. Furthermore, in some years, it may not be unusual for financially sound companies to have several ratios
with results outside the usual ranges. An insurance company may fall out of the usual range for one or more ratios because of specific transactions that are in
themselves immaterial. Generally, an insurance company will become subject to regulatory scrutiny and may be subject to regulatory action if it falls outside the
usual ranges of four or more of the ratios. Maiden Reinsurance only completed its re-domestication to Vermont in 2020, and it is therefore possible that it may
produce unusual ratios outside the usual ranges for more than four tests, principally due to the lack of prior year statutory data which is required for many of the
ratios to be computed.

State Legislative and Regulatory Changes

From time to time, various regulatory and legislative changes are proposed in the insurance industry. Among the proposals that have in the past been or are at
present being considered are proposals in various state legislatures (some of which proposals have been enacted) to conform portions of their insurance laws and
regulations to various model acts adopted by the NAIC.

While we are not actively underwriting reinsurance on new prospective risks, our insurance subsidiaries are required to comply with a wide variety of laws and
regulations  applicable  to  insurance  or  reinsurance  companies,  both  in  the  jurisdictions  in  which  they  are  organized  and  where  they  may  sell  insurance  and
reinsurance products. The insurance and regulatory environment, in particular for offshore insurance and reinsurance companies, has become subject to increased
scrutiny in many jurisdictions, including the U.S., various states within the U.S. and the EU. In the past, there have been Congressional and other initiatives in the
U.S. regarding increased supervision and regulation of the insurance industry. It is not possible to predict the future impact of changes in laws and regulations on
our operations. The cost of complying with any new legal requirements affecting our subsidiaries could have a material adverse effect on our business.

In addition, our subsidiaries may not always be able to obtain or maintain necessary licenses, permits, authorizations or accreditations. They also may not be
able to fully comply with, or to obtain appropriate exemptions from, the laws and regulations applicable to them. Any failure to comply with applicable law or to
obtain appropriate exemptions could result in restrictions on either the ability of the company in question, as well as potentially its affiliates, to do business in one
or  more  of  the  jurisdictions  in  which  they  operate  or  on  brokers  on  which  we  rely  to  produce  business  for  us.  In  addition,  any  such  failure  to  comply  with
applicable laws or to obtain appropriate exemptions could result in the imposition of fines or other sanctions. Any of these sanctions could have a material adverse
effect on our business. To date, no material fine, penalty or restriction has been imposed on us for failure to comply with any insurance law or regulation.

International Standards

U.S. federal and state regulators have committed in principle to adopting international standards with respect to basic regulatory issues such as accounting, risk
management  and  corporate  governance.  International  regulatory  considerations  are  increasingly  being  deliberated  by  the  NAIC  and  could  increase  regulatory
burdens  for  Maiden  Reinsurance  and  have  the  potential  to  negatively  impact  all  U.S.  insurers,  regardless  of  size.  Various  trade  associations  and  industry
participants are aggressively working to impact the NAIC adoption of these standards. However, the final outcome of these deliberations is unknown at this time.

Federal

Although the regulation of the business of insurance and reinsurance is predominantly performed by the states, federal initiatives, such as the Dodd-Frank Wall
Street Reform and Consumer Protection Act ("Dodd-Frank"), often have an impact on the insurance industry. From time to time, various federal regulatory and
legislative  changes  have  been  proposed  in  the  insurance  and  reinsurance  industry.  While  we  cannot  predict  the  exact  nature,  timing  or  scope  of  possible
governmental initiatives, there may be increased regulatory intervention in our industry in the future. For example, Dodd-Frank impacts the reinsurance industry in
several areas, including tort reform, corporate governance and the taxation of reinsurance companies. Dodd-Frank also prohibits a state from denying credit for
reinsurance if the state of domicile of the insurer purchasing the reinsurance recognizes credit for reinsurance.

On  January  13,  2017,  the  U.S.  Department  of  the  Treasury  ("U.S.  Treasury  Department")  and  the  office  of  the  U.S.  Trade  Representative,  ("USTR"),
announced  the  successful  completion  of  negotiations  for  a  "covered  agreement"  in  the  meaning  of  the  Dodd-Frank  Act  for  the  U.S.  and  an  Agreement  under
Article 218 of the Treaty on the Functioning of the European Union for the EU ("Covered Agreement"). The agreement covers three areas of prudential oversight:
(1) reinsurance; (2) group supervision; and (3) the exchange of information between insurance supervisors.

On September 22, 2017, the U.S. Treasury Department, USTR, and the EU formally signed the Covered Agreement. The agreement requires states to eliminate
reinsurance collateral within five years or risk preemption. In exchange, the EU will not impose local presence requirements on U.S. firms operating in the EU,
and effectively must defer to U.S. group capital regulation for U.S. entities of EU-based firms. The U.S. Treasury Department and USTR also released a U.S.
policy statement clarifying their interpretation of the Covered Agreement in several key areas including capital, group supervision and reinsurance. On June 25,
2019, the NAIC Executive Committee and Plenary adopted revisions to the Credit for Reinsurance Model Law and Credit for Reinsurance Model Regulation,
which implement the reinsurance collateral provisions of the Covered Agreements with the EU and the U.K. Bermuda is not covered under this agreement.

10

Sweden Insurance Regulation

Maiden LF and Maiden GF are subject to regulation and supervision by Finansinpektionen, the Swedish financial supervisory authority (the “Swedish FSA”).
As  Sweden  is  a  member  of  the  EU,  the  Swedish  FSA  supervision  is  recognized  across  all  locations  within  the  EU.  Generally,  the  Swedish  FSA  has  broad
supervisory and administrative powers over such matters as licenses, standards of solvency, investments, methods of accounting, form and content of financial
statements, minimum capital and surplus requirements, passporting permissions, approval of directors and officers, and annual and other report filings. In general,
such  regulation  is  for  the  protection  of  policyholders  rather  than  shareholders.  The  Company  believes  that  it  is  in  compliance  with  all  applicable  laws  and
regulations pertaining to its business that would have a material effect on its financial position in the event of non-compliance.

United Kingdom Insurance Regulation

The  U.K  left  the  EU  on  January  31,  2020  ("Brexit").  Maiden  LF  and  Maiden  GF  subsequently  established  branches  in  the  U.K.  to  enable  us  to  continue
underwriting  in  the  U.K.  post-Brexit.  The  branches  were  initially  accepted  into  the  U.K.'s  Temporary  Permissions  Regime  which  allowed  them  to  continue  to
write  insurance  in  the  U.K.  In  May  2022,  both  branches  were  authorized  by  the  Prudential  Regulation  Authority  (“PRA”)  and  Financial  Conduct  Authority
(“FCA”).  Both  branches  are  now  authorized  and  regulated  by  the  PRA  and  FCA.  The  Company  believes  that  it  is  in  compliance  with  all  applicable  laws  and
regulations pertaining to its business that would have a material effect on its financial position in the event of non-compliance.

Certain Bermuda Law Considerations

Maiden Holdings has been designated as non-resident for exchange control purposes by the Bermuda Monetary Authority ("BMA") and is required to obtain
the  permission  of  the  BMA  for  the  issue  and  transfer  of  all  of  its  shares.  The  BMA  has  given  its  consent  for:  (a)  the  issue  and  transfer  of  Maiden  Holdings'
common  shares,  up  to  the  amount  of  its  authorized  capital  from  time  to  time,  to  and  among  persons  that  are  non-residents  of  Bermuda  for  exchange  control
purposes; and (b) the issue and transfer of up to 20% of Maiden Holdings' common shares in issue from time to time to and among persons resident in Bermuda
for exchange control purposes.

Transfers and issues of Maiden Holdings' common shares to any resident in Bermuda for exchange control purposes may require specific prior approval under
the Exchange Control Act 1972. Because we are designated as non-resident for Bermuda exchange control purposes, we are allowed to engage in transactions, and
to pay dividends to Bermuda non-residents who are holders of our common shares, in currencies other than the Bermuda Dollar.

The  Economic  Substance  Act  2018,  as  amended  (“ESA”)  came  into  force  in  Bermuda  on  January  1,  2019  and  impacts  every  Bermuda  registered  entity
engaged in a “relevant activity” to maintain a substantial economic presence in Bermuda and to satisfy economic substance requirements. Under the ESA, holding
entity activities (as defined in the ESA and the Economic Substance Regulations 2018, as amended) are deemed a relevant activity. To the extent that the ESA
applies to Maiden Holdings, we are required to demonstrate compliance with economic substance requirements that we have “adequate” economic substance in
Bermuda, and we must file an annual economic substance declaration with the Bermuda Registrar of Companies ("Registrar") on that basis. Any entity that must
satisfy economic substance requirements but fails to do so could face automatic disclosure to competent authorities in the EU of the information filed by the entity
with the Registrar, face financial penalties, restriction or regulation of its business activities and/or may be struck off as a registered entity in Bermuda.

The Terrorism Risk Insurance Program Reauthorization Act of 2019

Terrorism Risk Insurance Act of 2002 ("TRIA"), which was previously amended and extended in 2005, 2007, 2015 and again in 2019 by the Terrorism Risk
Insurance Program Reauthorization Act of 2019 ("TRIPRA"), was enacted to ensure the availability of insurance coverage for terrorist acts in the U.S. This law
renewed  the  prior  federal  terrorism  risk  insurance  program.  It  was  extended  through  December  31,  2027  with  certain  modifications  in  the  provisions  of  the
expiring program. TRIA does not apply to reinsurers directly but does apply directly to insurers and to excess and surplus lines insurers. TRIPRA has impacted
some of our reinsurance clients, but not all due to the lines of business covered by TRIA. Also, in general, our reinsurance contracts contain inuring language
regarding  any  potential  recoveries  from  TRIA.  Additional  material  for  TRIA  and  TRIPRA,  including  U.S.  Treasury  Department  issued  interpretive  letters,  are
found on the U.S. Treasury Department’s website.

Taxation of the Company and its Subsidiaries

The following summary of certain taxation matters is based upon current law. Legislative, judicial or administrative changes may be forthcoming that could
affect  this  summary.  Our  U.S.  subsidiaries  are  subject  to  federal,  state  and  local  corporate  income  taxes  and  other  taxes  applicable  to  U.S.  corporations.  The
Company has subsidiary operations in various other locations around the world, including Canada, Ireland, Sweden and the U.K., that are subject to relevant taxes
in those jurisdictions. The discussion below covers only the principal locations in which the Company or its subsidiaries are subject to taxation.

Bermuda

Maiden Holdings has received from the Minister of Finance an assurance under The Exempted Undertakings Tax Protection Act, 1966 to the effect that in the
event that there is any legislation enacted in Bermuda imposing tax computed on profits or income, or computed on any capital asset, gain or appreciation, or any
tax in the nature of estate duty or inheritance tax, then the imposition of any such tax shall not be applicable to Maiden Holdings or to any of its operations or the
shares, debentures or other obligations of Maiden Holdings until March 31, 2035. These assurances are subject to the proviso that they are not construed to prevent
the  application  of  any  tax  or  duty  to  such  persons  as  are  ordinarily  resident  in  Bermuda  (Maiden  Holdings  is  not  currently  so  designated)  or  to  prevent  the
application of any tax payable in accordance with the provisions of The Land Tax Act, 1967 of Bermuda or otherwise payable in relation to the property leased to
us.

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Sweden

Maiden  LF  and  Maiden  GF  are  subject  to  Swedish  taxation  on  net  profits  irrespective  of  whether  the  profits  are  generated  through  business  in  general  or
capital. To the extent that net profits are generated, profits are taxed at a rate of 20.6%. Foreign entities are subject to tax in Sweden only to the extent they have a
permanent establishment in Sweden or if the income is related to certain types of assets, typically real estate, or partnership income. Dividends paid to foreign
shareholders  may  be  subject  to  withholding  tax  with  a  maximum  of  30%  although  in  many  cases  tax  is  reduced  because  of  a  tax  treaty  or  under  domestic
legislation.  A  foreign  entity  is  deemed  to  have  a  permanent  establishment  in  Sweden  under  the  rules  very  similar  to  those  applied  by  The  Organisation  for
Economic  Co-operation  and  Development  ("OECD").  Other  than  Maiden  LF  and  Maiden  GF,  we  believe  that  the  Company  has  operated  and  will  continue  to
operate its business in a manner that will not cause it to be treated as having a permanent establishment in Sweden. There is no withholding tax on interest paid by
a Swedish borrower to a foreign lender.

United Kingdom

Maiden Global, Maiden LF U.K. Branch and Maiden GF U.K. Branch are tax residents in the U.K. and are currently subject to corporation tax in the U.K. on
their trading and other taxable profits. The main rate of U.K. corporation tax is currently 19% (rising to 25% from April 2023). Non-U.K. resident corporations are
within the scope of corporation tax in the U.K. if they carry on a trade in the U.K. through a permanent establishment. Reinsurance business developed previously
by Maiden Global was underwritten by Maiden Reinsurance. Other than in respect of Maiden Global, Maiden LF U.K. Branch and Maiden GF U.K. Branch, we
believe that the Company has operated and will continue to operate its business in a manner that will not cause it to be treated as carrying on a trade within the
U.K. Any U.K. source income of non-U.K. resident corporations may be subject to U.K. withholding tax, subject to the availability of treaty relief or any other
applicable  exemptions.  Dividends  paid  by  Maiden  Global  are  not  subject  to  U.K.  withholding  tax.  Interest  paid  by  Maiden  Global  may  be  subject  to  U.K.
withholding tax at a rate of up to 20%, subject to the availability of treaty relief or any other applicable exemptions.

United States of America

The Tax Cuts and Jobs Act (the "2017 Act") reduced the corporate U.S. tax rate to 21%, eliminated the alternative minimum tax and limited the deductibility of
interest  expense,  among  other  things.  In  the  context  of  the  taxation  of  U.S.  property/casualty  insurance  companies  such  as  the  Company,  the  2017  Act  also
modified  the  loss  reserve  discounting  rules  and  the  proration  rules  that  apply  to  reduce  reserve  deductions  to  reflect  the  lower  corporate  income  tax  rate.  In
addition, the 2017 Act included certain provisions intended to eliminate certain perceived tax advantages of companies (including insurance companies) that have
legal domiciles outside the U.S. but have certain U.S. connections and U.S. persons investing in such companies.  For example, the 2017 Act includes a base
erosion  anti-avoidance  tax  (the  "BEAT")  that  could  make  affiliate  reinsurance  between  U.S.  and  non-U.S.  members  of  our  group  economically  unfeasible.  As
discussed  in  more  detail  below,  the  2017  Act  also  revised  the  rules  applicable  to  passive  foreign  investment  companies  ("PFICs")  and  controlled  foreign
corporations ("CFCs"). Further, it is possible that other legislation could be introduced and enacted by the current Congress or future Congresses that could have
an adverse impact on us. Additionally, tax laws and interpretations regarding whether a company is engaged in a U.S. trade or business or whether a company is a
CFC or a PFIC or has related person insurance income ("RPII") are subject to change, possibly on a retroactive basis. The U.S. Treasury Department recently
issued final and proposed regulations intended to clarify the application of the insurance income exception to the classification of a non-U.S. insurer as a PFIC and
provide guidance on a range of issues relating to PFICs, and recently issued proposed regulations that would expand the scope of the RPII rules. New regulations
or pronouncements interpreting or clarifying such rules may be forthcoming as well. The Company cannot be certain if, when or in what form such regulations or
pronouncements may be provided and whether such guidance will have a retroactive effect.

Maiden  NA  and  its  subsidiaries  (collectively,  the  "Maiden  NA  Companies")  transact  business  in  and  are  subject  to  taxation  in  the  U.S.,  and  Maiden
Reinsurance  is  subject  to  taxation  in  the  U.S.  since  the  effective  date  of  its  re-domestication.  Other  than  the  Maiden  NA  Companies,  we  believe  that  we  have
operated and will continue to operate our business in a manner that will not cause us to be treated as engaged in a trade or business within the U.S. On this basis,
other than the Maiden NA Companies, we do not expect to be required to pay U.S. corporate income taxes (other than withholding and excise taxes as described
below). The maximum federal corporate income tax rate has been reduced by the 2017 Act to 21% for a foreign corporation’s income that is effectively connected
with a trade or business in the U.S. In addition, U.S. branches of foreign corporations may be subject to the branch profits tax, which imposes a tax on U.S. branch
after-tax earnings that are deemed repatriated out of the U.S., for a potential maximum effective federal tax rate of 44.7% on the net income connected with a U.S.
trade or business.

Foreign corporations not engaged in a trade or business in the U.S. are subject to U.S. income tax, effected through withholding by the payer, on certain fixed
or determinable annual or periodic gains, profits and income derived from sources within the U.S. as enumerated in Section 881(a) of the Internal Revenue Code,
such as dividends and interest on certain investments. The U.S. imposes an excise tax on insurance and reinsurance premiums paid to foreign insurers or reinsurers
with respect to risks of a U.S. person located wholly or partly within the U.S. ("U.S. person") or risks of a foreign person engaged in the conduct of a U.S. trade or
business located in the U.S. The rate of tax applicable to reinsurance is 1% of gross premiums.

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Where You Can Find More Information

We maintain our principal website at www.maiden.bm. The information on our websites is not incorporated by reference in this Annual Report on Form 10-K.
We make available, free of charge through our principal website, our financial information, including the information contained in our Annual Reports on Form
10-K, Quarterly Reports on Form 10-Q, Current Reports on Form 8-K and amendments to those reports filed or furnished pursuant to Section 13(a) or 15(d) of the
Securities Exchange Act of 1934, as amended (the "Exchange Act"), as soon as reasonably practicable after we electronically file such material with, or furnish
such material to the SEC. We also make available, free of charge through our principal website, our Audit Committee Charter, Compensation Committee Charter,
Nominating  and  Corporate  Governance  Committee  Charter,  and  Code  of  Business  Conduct  and  Ethics.  Such  information  is  also  available  in  print  for  any
shareholder  who  sends  a  request  to  Maiden  Holdings,  Ltd.,  Ideation  House,  94  Pitts  Bay  Road,  1   Floor,  Pembroke  HM  08,  Bermuda,  Attention:  Secretary.
Reports and other information we file with the SEC may also be viewed at the SEC’s website at www.sec.gov or viewed or obtained at the SEC Public Reference
Room at 100 F Street, N.E., Washington, DC 20549.

st

Information on the operation of the SEC Public Reference Room may be obtained by calling the SEC at 800-SEC-0330. Any shareholder or other interested
party who desires to contact any member of the Board (or our Board as a group) may do so in writing to the following address: Maiden Holdings, Ltd., Ideation
House, 94 Pitts Bay Road, 1  Floor, Pembroke HM 08, Bermuda, Attention: Secretary. Communications are distributed to the Board, or to any individual directors
as appropriate, depending on the facts and circumstances outlined in the communication.

st

13

Item 1A. Risk Factors.
Introduction

Investing in our securities carries risk. Managing risk effectively is critical to our success, and our organization is built around intelligent risk assumptions and
prudent risk management. We have identified what we believe reflect key significant risks to the organization, and in turn to our shareholders, which are outlined
below. Any of the risks described below could result in a significant or material adverse effect on our results of operations or financial condition. In addition to
these enumerated risks, we face numerous other strategic, operational and emerging risks that could in the aggregate lead to shortfalls to our long-term goals or
add to short-term volatility in our earnings. The following review of important risk factors should not be construed as exhaustive and should be read in conjunction
with  other  cautionary  statements  that  are  included  herein  or  elsewhere.  The  words  or  phrases  believe,  anticipate,  estimate,  project,  plan,  expect,  intend,  hope,
forecast, evaluate, will likely result or will continue or words or phrases of similar import generally involve forward-looking statements. All of the risks that may
affect our financial or operating performance may not be material at this time but may become material in the future. As used in these Risk Factors, the terms
"we", "our" or "us" may, depending upon the context, refer to the Company, to one or more of the Company’s consolidated subsidiaries or to all of them taken as a
whole.

Business

We  have  incurred  volatile  operating  results  in  recent  years.  There  can  be  no  assurance  that  we  will  maintain  operating  profitability  or  return  to  active
underwriting of new prospective reinsurance risks.

We produced a net loss of $60.0 million in 2022, compared to net income of $26.6 million during 2021, largely the result of loss development from the run-off
of  our  legacy  reinsurance  obligations.  While  we  have  taken  significant  actions  in  recent  years  to  strengthen  our  loss  reserve  and  capital  position,  these  older
liabilities are dependent on the reporting by our ceding companies and can be subject to volatility. While we have purchased additional reinsurance protection to
eliminate potential volatility of loss reserves from this legacy business, the accounting for this reinsurance protection precludes us from recognizing recoveries
until paid losses reach certain contractual retention limits in the agreement and thus our GAAP results reported herein will not reflect this reinsurance until those
limits are exceeded, which we presently expect to occur in 2025. There can be no assurance that this reinsurance or that the timing and accounting recognition of
recoveries under that reinsurance agreement will be sufficient to protect us against further declines in shareholders’ equity.

We  have  taken  steps  to  restructure  our  business  by  disposing  of  unprofitable  operations  and  terminating  reinsurance  agreements  in  both  of  our  reporting
segments while significantly reducing headcount and overhead expenses. While we believe these actions along with our revised strategy will produce operating
profitability, there can be no assurance that these actions will achieve their intended effects or that such reinsurance will be sufficient to protect us against further
adverse loss reserve development. Further, as our insurance liabilities continue to run off, our investment income will continue to decrease which may adversely
affect our profitability. While we continue to reduce our operating expenses, make additional investments which we believe will produce enhanced investment
returns,  and  now  write  new  legacy  retroactive  risks,  there  can  be  no  assurance  that  these  measures  will  overcome  the  expected  decline  in  investment  income.
Finally, we have not yet determined if and when we may resume active underwriting of new prospective risks which would result in increased revenue.

While  we  continue  to  believe  we  will  operate  as  a  going  concern,  there  can  be  no  assurance  that  this  will  continue  to  be  the  case  if  we  do  not  maintain

operating profitability or if future significant declines in our shareholders’ equity occur.

The  inability  of  management  to  successfully  implement  its  business  strategy  could  result  in  a  further  decline  of  capital,  materially  adversely  affecting  our
financial condition and results of operations and may create enhanced risks.

Management continues to evaluate various operating strategies that are likely to be significantly different than our prior strategic business focus. In November
2020, we formed GLS which specializes in providing a full range of legacy services to small insurance entities, particularly those in run-off or with blocks of
reserves  that  are  no  longer  core  to  those  companies'  operations,  working  with  clients  to  develop  and  implement  finality  solutions  including  acquiring  entire
companies.  We  believe  the  formation  of  GLS  is  highly  complementary  to  our  overall  longer-term  strategy.  However,  it  may  take  some  time  for  GLS  to  gain
sufficient  scale  to  achieve  its  objectives,  and  its  results  may  not  reach  the  objectives  we  expect  to  establish  for  it  over  time.  Since  2020,  our  revised  strategy
includes  expanded  investment  activities.  This  has  included  changes  to  our  approaches  to  asset  and  capital  management  and  we  may  or  may  not  resume  active
reinsurance underwriting of new prospective risks in the future. Further, as part of its re-domestication to the State of Vermont in the U.S., Maiden Reinsurance is
required  to  closely  consult  with  the  Vermont  DFR  before  it  considers  resuming  active  reinsurance  underwriting  of  new  prospective  risks  and  on  any  matters
related  to  capital  management  and  business  strategy.  There  can  be  no  assurance  that  the  implementation  of  the  new  business  plan  will  succeed  or  will  be
satisfactory to the Vermont DFR, which could have a material adverse effect on our business, operations and financial condition.

Any new business initiatives involving the development of new products or expanding existing products in new or historically targeted markets may involve
substantial capital and operating expenditures, which may negatively impact our results of operations and shareholders' equity. In addition, the demand for new
products or in new markets may not meet our expectations. To the extent we can market new products or expand in new markets, our risk exposures may change
and the data and models we use to manage such exposures may not be as sophisticated as those we use in existing markets or with existing products. This, in turn,
could lead to losses in excess of expectations. Additionally, the re-domestication of Maiden Reinsurance to the U.S. may limit our ability to reinsure risk outside
of the U.S. and may have an adverse effect on our capital and ability to write new business.

As part of our ongoing efforts to continually improve our performance, we regularly evaluate our business plans and strategies, which may result in material
changes to those plans. We are subject to increasing risks related to our ability to successfully implement our evolving plans and strategies. Changing plans and
strategies requires significant management of time and effort and may divert management’s attention from our core operations and competencies, and our efforts
to improve

14

our capital position and solvency. Moreover, modifications we undertake to our operations may not immediately result in improved financial performance.

Therefore,  risks  associated  with  implementing  or  changing  our  business  strategies  and  initiatives,  including  risks  related  to  developing  or  enhancing  the
operations, controls and other infrastructure required for these strategies and initiatives, may not have a positive impact on our publicly reported results until many
years after implementation, possibly leading to an adverse effect on our long-term results of operations and financial condition.

Our  actual  losses  may  be  greater  than  our  reserve  for  loss  and  LAE,  which  could  materially  negatively  impact  our  financial  condition  and  results  of
operations.

Our success depends upon our ability to assess accurately the risks associated with the businesses that we will reinsure, that we have acquired or will acquire in
the future. Significant periods of time often elapse between the occurrence of an insured loss, the reporting of the loss to an insurer and the reporting of the loss by
the insurer to its reinsurer and the ultimate disposition of that loss. The reserves we establish represent estimates of amounts needed to pay reported losses and
unreported losses and the related LAE. Loss reserves are only an estimate of what an insurer or reinsurer anticipates the ultimate costs of claims to be and do not
represent  an  exact  calculation  of  liability.  Estimating  loss  reserves  is  a  difficult  and  complex  process  involving  many  variables,  inherent  uncertainty,  statistical
modeling,  and  subjective  judgments.  As  part  of  our  reserving  process,  we  review  historical  data  as  well  as  perform  actuarial  and  statistical  projections  using
proprietary  models  and  consider  the  impact  of  various  factors  such  as:  trends  in  claim  frequency  and  severity;  changes  in  operations;  emerging  economic  and
social trends; inflation; and changes in the regulatory and litigation environments.

This process assumes that past experience, adjusted for the effects of current developments and anticipated trends, is an appropriate basis for predicting future
events. In addition, reserving models that are capable of estimating reserves using a variety of methodologies are utilized during the reserving process. There is no
precise method, however, for evaluating the impact of any specific factor on the adequacy of reserves, and actual results are likely to differ from original estimates.
Reserve models can introduce further process and parameter risk when data and methodologies are interpreted or utilized in a manner which is inconsistent with
the actual underlying characteristics of the reinsured exposure. These risks could arise due to incorrect use of the models, or the use of a model or methodology
that is inappropriate. In addition, unforeseen losses, the type or magnitude of which we cannot predict, may emerge in the future. Given the inherent uncertainty in
the reserving process and models used for reserve estimation, we may not accurately react to the reporting and payment of loss in the projection of our reserve for
loss and LAE.

We will establish or adjust reserves for our insurance subsidiaries in part based upon loss data received from the ceding companies with which we do business.
There is a time delay that elapses between the receipt and recording of claims results by the ceding insurance companies and the receipt and recording of those
results by us. Accordingly, the establishment and adjustment of reserves for our insurance subsidiaries is dependent upon timely and accurate estimate reporting
from cedants and agents.

We  use  our  own  proprietary  models  to  provide  us  with  an  objective  risk  assessment  relating  to  risks  in  our  reinsurance  portfolio.  These  models  help  us  to
inform management and other stakeholders of capital requirements and to improve the risk/return profile or minimize the amount of capital required to cover the
risks  in  each  reinsurance  contract  in  our  overall  portfolio  of  reinsurance  contracts.  However,  given  the  inherent  uncertainty  of  modeling  techniques  and  the
application of such techniques, these models and databases may not accurately address the emergence of a variety of matters which might be deemed to impact
certain of our coverages. Accordingly, these models may understate the exposures we are assuming and our financial results may be adversely impacted, perhaps
significantly.

In addition, the COVID-19 pandemic disrupted established claims adjudication and settlement processes. These disruptions could impact the consistency of
data received from our cedants and agents. While we do not believe these disruptions have materially impacted our ability to appropriately evaluate the exposures,
it could potentially impact the judgments we make in setting reserves.

While we have established our reserves to a level we believe to be sufficient to cover losses assumed by us when we recognize prior period development, there
can be no assurance that losses will not deviate from our reserves, possibly by material amounts. We have experienced significant adverse development of our loss
reserves in prior years, including in 2022. Further, the additional reinsurance protection we have purchased to protect against further adverse development in loss
reserves may be insufficient compared to the actual losses that emerge and we may need to recognize adverse development which would reduce our results of
operations and shareholders' equity, possibly materially. To the extent our actual reported losses exceed expected losses, the carried estimate of the ultimate losses
will be increased, which would represent unfavorable reserve development, and in turn could have a material adverse effect on our financial condition.

The effects of emerging claims and coverage issues on our business are uncertain.

As  industry  practices  and  legal,  judicial,  social  and  other  environmental  conditions  change,  unexpected  issues  related  to  claims  and  coverage  may  emerge.
These issues may adversely affect our business by either extending coverage beyond our underwriting intent or by increasing the number or size of claims. In
some instances, these changes may not become apparent until sometime after we have issued insurance or reinsurance contracts that are affected by the changes.
As  a  result,  the  full  extent  of  liability  under  our  reinsurance  contracts  may  not  be  known  for  many  years  after  a  contract  is  issued.  Our  exposure  to  these
uncertainties could be exacerbated by an increase in insurance and reinsurance contract disputes, arbitration and litigation.

Our business is subject to risks related to litigation. Losses from legal and regulatory actions may have a material adverse effect on our reputation, operating
results, cash flows, financial condition and prospects.

We may from time to time be subject to litigation or other legal or regulatory actions in the ordinary course of business relating to our current and past business

operations, including, but not limited to, disputes over coverage or claims adjudication,

15

including claims alleging that we have acted in bad faith in the administration of claims by our policyholders, disputes with our agents, producers and termination
of contracts and related claims and disputes with former employees. We also cannot determine with any certainty what new theories of recovery may evolve or
what their impact may be on our business.

We also may be subject to litigation from security holders due to the diminution in value of our securities as a result of our operating results and financial
condition. Defending against these actions may require us to utilize significant resources in our defense as well as result in a significant amount of time by our
senior management.

An adverse resolution of one or more lawsuits or arbitration could have a material adverse effect on our results of operations in a particular fiscal quarter or

year.

Our reinsurers may not pay losses in a timely fashion, or at all, which could have a material adverse effect on our results of operations or financial condition.

At  December  31,  2022,  we  had  $550.5  million  due  to  us  from  one  reinsurer,  Cavello,  consisting  of  losses  recoverable  from  Cavello  under  the  retrocession
agreement  of  $60.1  million  and  reinsurance  recoverable  on  unpaid  losses  under  the  retroactive  reinsurance  agreement  of  $490.4  million.  Cavello  provided
collateral in the form of a letter of credit in the amount of $445.0 million to AmTrust under the LPT/ADC Agreement with Enstar Group Limited ("Enstar") on
July  31,  2019,  pursuant  to  which  Cavello  assumed  the  loss  reserves  as  of  December  31,  2018  associated  with  the  AmTrust  Quota  Share,  subject  to  additional
collateral funding requirements. As of December 31, 2022, the amount of collateral required was $461.6 million.

We may or may not use retrocessional and reinsurance coverage to limit our exposure to risks. Any retrocessional or reinsurance coverage that we obtain may
be limited, and credit and other risks associated with our retrocessional and reinsurance arrangements may result in losses which could adversely affect our
financial condition and results of operations.

We have provided reinsurance to our clients and in turn we may or may not retrocede reinsurance we have assumed to other insurers and reinsurers. If we do
not  use  or  cannot  obtain  retrocessional  coverage  or  reinsurance,  our  exposure  to  losses  will  be  greater  than  if  we  did  obtain  such  coverage.  If  we  do  obtain
retrocessional or reinsurance coverage, some of the insurers or reinsurers to whom we may retrocede coverage or reinsure with may be domiciled in Bermuda or
other non-U.S. locations. We would be subject to credit and other risks that depend upon the financial strength of these reinsurers. Further, we will be subject to
credit risk with respect to any retrocessional or reinsurance arrangements because the ceding of risk to reinsurers and retrocessionaires would not relieve us of our
liability  to  the  clients  or  companies  we  insure  or  reinsure.  Our  failure  to  establish  adequate  reinsurance  or  retrocessional  arrangements  or  the  failure  of  any
retrocessional arrangements to protect us from overly concentrated risk exposure could adversely affect our business, financial condition and results of operation.
We may attempt to mitigate such risks by retaining collateral or trust accounts for premiums and claims receivables, but nevertheless we cannot be assured that
reinsurance will be fully collectable in the case of all potential claims outcomes.

The  failure  of  any  of  the  loss  limitation  methods  we  have  employed  or  could  employ  in  the  future  could  have  a  material  adverse  effect  on  our  results  of
operations or financial condition.

We seek to limit loss exposure through loss limitation provisions in policies we write, such as limitations on the amount of losses that can be claimed under a
policy, limitations or exclusions from coverage and provisions relating to choice of forum, which are intended to assure that our policies are legally interpreted as
intended.  There  can  be  no  assurance  that  these  contractual  provisions  will  be  enforceable  in  the  manner  expected  or  that  disputes  relating  to  coverage  will  be
resolved in our favor. If the loss limitation provisions in the policies are not enforceable or disputes arise concerning the application of such provisions, the losses
we incur could be materially higher than expected and our financial condition and results of operations could be adversely affected.

We depend on the policies, procedures and expertise of ceding companies for the business we have written in the past; these companies may have failed to
accurately assess and price the risks they have underwritten, which may lead us to inaccurately assess and price the risks we assumed.

While  we  are  not  presently  engaged  in  active  reinsurance  underwriting  of  new  prospective  risks,  we  are  engaged  in  active  reinsurance  underwriting  of
retroactive risks. Our participation in these property and casualty reinsurance markets means the success of our prior underwriting efforts depends, in part, upon
the policies, procedures and expertise of the ceding companies making the original underwriting decisions. As is common among reinsurers, we do not separately
evaluate each of the individual risks assumed under reinsurance treaties. We face the risk that these ceding companies may have failed to accurately assess the
risks that they assumed initially, which, in turn, may lead us to inaccurately assess the risks we assumed.

If we have failed to establish and receive appropriate pricing or failed to contractually limit our exposure to such risks, we could face significant losses on these

contracts, which could have a material adverse impact on our financial results.

The failure of our underwriting process and risk management could have an adverse effect on our results of operations or financial condition.

As noted, while we are not presently engaged in active reinsurance underwriting of new prospective reinsurance risks, we are engaged in active reinsurance
underwriting of retroactive risks. We also assume risk on a primary basis through Maiden LF & Maiden GF. As we write these risks, we similarly seek to manage
our  loss  exposure  by  maintaining  a  disciplined  underwriting  process  throughout  our  (re)insurance  operations.  Underwriting  is  a  matter  of  judgment,  involving
important assumptions about matters that are inherently unpredictable and beyond our control, and for which historical experience and probability analysis may
not provide sufficient guidance. The failure of any of the underwriting risk management strategies that we employ could have a material adverse effect on our
financial condition, results of operations or cash flows.

We rely on internal controls and underwriting guidelines to limit our risk exposure within prescribed parameters. However, our controls and monitoring efforts

may have been ineffective, permitting one or more underwriters to exceed underwriting

16

authority  and  causing  us  to  (re)insure  risks  outside  the  agreed  upon  guidelines.  To  the  extent  that  our  underwriters  exceeded  their  authorities,  agreed  to
inappropriate contract terms and conditions or were influenced by broker incentives, or if there was inaccurate underwriting data captured and reported leading to
licensing and sanction breaches, our financial condition or results of operations could be materially adversely affected.

We may be required to accelerate the amortization of deferred acquisition costs or establish premium deficiency reserves.

Deferred acquisition costs represent incremental direct costs related to the successful acquisition of new or renewal insurance contracts. The balances of such
costs are capitalized as an asset and amortized into income over the expected lives of the underlying insurance contracts. On an ongoing basis, we test these assets
recorded on our balance sheet to determine whether the amounts are recoverable under current assumptions. To date, we have concluded that no such premium
deficiency exists. If facts and circumstances change, these tests and reviews could lead to the establishment of a premium deficiency reserve which would require
a write down in the carried value of our deferred acquisition costs. Such results could have an adverse effect on the results of our operations and our financial
condition.

Failure of our information technology systems could disrupt our business and adversely impact our profitability.

We believe our information technology and application systems are critical to our business and reputation. We have licensed certain systems and data from
third  parties.  We  cannot  be  certain  that  we  will  have  access  to  these,  or  comparable  service  providers,  or  that  our  technology  or  applications  will  continue  to
operate as intended. A major defect or failure in our internal controls or information technology and application systems could result in management distraction,
harm to our reputation, a loss or delay of revenues or increased expense.

Technology breaches or failures, including, but not limited to, those resulting from cyber-attacks on us or our business partners and service providers, could
disrupt or otherwise negatively impact our business.

Information technology and application systems can streamline many business processes and ultimately reduce the cost of operations, however, technology
initiatives  present  certain  risks.  Our  business  is  dependent  upon  our  employees  and  outsources  ability  to  perform,  in  an  efficient  and  uninterrupted  fashion,
necessary business functions. Like all companies, our information technology systems are vulnerable to data breaches, interruptions or failures due to events that
may be beyond our control, including, but not limited to, natural disasters, theft, terrorist attacks, computer viruses, hackers and general technology failures. Our
information technology systems include the Internet and third-party hosted services. We use information systems to process financial information and results of
operations  for  internal  reporting  purposes  and  for  regulatory  financial  reporting,  legal  and  tax  requirements.  We  also  use  information  systems  for  electronic
communications with customers and our various locations.

A shutdown or inability to access one or more of our facilities, a power outage, a security breach, or a failure of one or more of our information technology,
telecommunications  or  other  systems  could  significantly  impair  our  ability  to  perform  such  functions  on  a  timely  basis.  These  incidents  could  be  caused  by
malicious  or  disruptive  software,  computer  hackers,  rogue  employees,  cyber-attacks,  failures  of  telecommunications  systems  or  other  catastrophic  events.  If
sustained  or  repeated,  such  a  business  interruption,  system  failure  or  service  denial  could  result  in  a  deterioration  of  our  ability  to  write  and  process  business,
provide customer service, pay claims in a timely manner or perform other necessary business functions. Furthermore, a significant portion of the communications
between our employees and our business, banking and investment partners depends on information technology and electronic information exchange. In addition,
we may suffer financial and reputational damage because of lost or misappropriated confidential information belonging to us, and may become subject to legal
action and increased regulatory oversight. We could also be required to spend significant financial and other resources to remedy any damage caused to repair or
replace information systems.

We believe that we have established and implemented appropriate security measures, controls and procedures to safeguard our information technology systems
and to prevent unauthorized access to such systems and any data processed and/or stored in such systems, and we periodically employ third parties to evaluate and
test the adequacy of such systems, controls and procedures. In addition, we have established a business continuity plan which is designed to ensure that we are
able to maintain all aspects of our key business processes functioning in the midst of certain disruptive events, including any disruptions to or breaches of our
information  technology  systems.  We  continue  to  make  investments  in  technologies,  cyber-insurance  and  training.  Our  business  continuity  plans  are  tested  and
evaluated for adequacy. Despite these safeguards, disruptions to and breaches of our information technology systems are possible and may negatively impact our
business.

Like  most  major  corporations,  the  Company’s  information  systems  are  a  target  of  attacks.  Although  we  have  experienced  no  known  material  or  threatened
cases involving unauthorized access to our information technology systems and data or unauthorized appropriation of such data to date, we have no assurance that
such technology breaches will not occur in the future.

Ongoing economic uncertainty could materially and adversely affect our business, our liquidity and financial condition.

Global  economies  and  financial  markets  have,  from  time  to  time,  experienced  significant  disruption  or  deterioration  and  likely  will  experience  periods  of
disruption  or  deterioration  in  the  future.  In  addition,  U.S.  federal  and  state  governments  continue  to  experience  significant  structural  fiscal  deficits,  creating
uncertainty as to levels of taxation, inflation, regulation and other economic fundamentals that may impact future growth prospects. The continuing presence of
the COVID-19 virus globally continues to inject significant economic uncertainty which may have a material effect on the global economy and financial markets.
Continuation of these conditions may potentially affect (among other aspects of our business) the demand for and claims made under our products, the ability of
clients, counterparties and others to establish or maintain their relationships with us, our ability to access and efficiently use internal and external capital resources
and our investment performance.

Our agency mortgage-backed securities ("Agency MBS") constitute 10.9% of fixed maturity investments at December 31, 2022.  As with other fixed income

investments, the fair value of these securities fluctuates depending on market and other

17

general economic conditions and the interest rate environment. Changes in interest rates can expose us to changes in the prepayment rate on these investments. In
periods of declining interest rates, mortgage prepayments generally increase and mortgage-backed securities ("MBS") are prepaid more quickly, requiring us to
reinvest the proceeds at lower market rates. Conversely, in periods of rising rates, mortgage prepayments generally fall, preventing us from taking full advantage
of the higher level of rates. However, economic conditions may curtail prepayment activity on the underlying mortgages if refinancing is difficult, thus limiting
prepayments on the MBS portfolio. In the event that these conditions persist and result in a prolonged period of economic uncertainty, our results of operations,
our financial condition and/or liquidity, and our prospects could be materially and adversely affected.

We may face substantial exposure to losses from terrorism, acts of war and political instability.

We may have exposure to losses resulting from acts of terrorism, acts of war and political instability as a reinsurer of U.S. domiciled insurers. U.S. insurers are
required by state and federal law to offer coverage for terrorism in certain commercial lines. These risks are inherently unpredictable, although recent events may
lead  to  increased  frequency  and  severity.  It  is  difficult  to  predict  the  occurrence  of  these  perils  with  statistical  certainty  or  to  estimate  the  amount  of  loss  an
occurrence will generate. We closely monitor the amount and types of coverage we provide for terrorism risk under insurance policies and reinsurance treaties. We
often seek to exclude or limit terrorism when we cannot reasonably evaluate the risk of loss or charge an appropriate premium for such risk. Even in cases where
we have deliberately sought to exclude coverage, we may not be able to eliminate our exposure to terrorist acts, and thus it is possible that these acts could have a
material adverse effect on us.

Liquidity, Capital Resources and Investments

We may not have sufficient unrestricted liquidity to meet our obligations.

Maiden Holdings is a holding company. As a result, we do not have, and will not have, any significant operations or assets other than our ownership of the
shares of our subsidiaries. Dividends and other permitted payments from our operating subsidiaries are expected to be our sole source of funds to meet ongoing
cash requirements at Maiden Holdings, including debt service payments and other expenses. As of December 31, 2022 and as of the date hereof, our insurance
subsidiaries' ability to make distributions require the prior approvals of their respective domestic regulators. Maiden Holdings may need to borrow funds from its
subsidiaries if funds from dividends are not available to meet ongoing cash requirements. The impact of applicable regulatory capital requirements such as risk
based capital ratios under U.S. law could impact the ability of Maiden Reinsurance to pay future cash dividends.

Maiden Reinsurance uses trust accounts, loan to related party, funds withheld and letters of credit to meet collateral requirements. Consequently, cash and cash
equivalents  and  investments  are  pledged  in  favor  of  ceding  companies  in  order  to  comply  with  relevant  insurance  regulations  or  contractual  requirements.  At
December 31, 2022, restricted cash and cash equivalents and fixed maturity investments used as collateral were $296.8 million and represents 82.2% of the fair
value of our total fixed maturity investments and cash and cash equivalents (including restricted cash and cash equivalents) at that date. At December 31, 2022,
Maiden Reinsurance had $20.5 million in unrestricted cash and cash equivalents and fixed maturity investments. On a consolidated basis, the Company had $64.3
million in unrestricted cash and cash equivalents and fixed maturity investments at December 31, 2022.

Based on our current estimate of 2023 financial projections, we believe we will have sufficient liquidity to meet and fulfill our obligations including payments
due under our outstanding publicly-traded senior notes which were issued in 2013 (the "2013 Senior Notes") by Maiden NA in the principal amount of $152.5
million,  all  of  which  is  currently  outstanding  and  is  subject  to  a  guarantee  by  Maiden  Holdings,  and  our  outstanding  publicly-traded  senior  notes  which  were
issued in 2016 (the "2016 Senior Notes") in the principal amount of $110.0 million, all of which is currently outstanding (the 2016 Senior Notes collectively with
the  2013  Senior  Notes,  the  "Senior  Notes").  However,  should  our  operating  results  deteriorate,  should  additional  collateral  be  required  under  our  contractual
arrangements  with  reinsured  prior  to  the  receipt  of  recoveries  under  reinsurance  agreements  we  have  entered  into  or  should  excess  collateral  under  those
arrangements not be returned to the Company quickly enough, we cannot assure that we will maintain sufficient unrestricted liquidity to meet those obligations.

A significant amount of our invested assets are subject to changes in interest rates and market volatility. If we are unable to realize our investment objectives,
our financial condition and results of operations may be adversely affected.

Investment income is an important component of our consolidated net income. At December 31, 2022, total investments of $587.1 million represented 92.6%
of  our  total  cash  and  investments.  Total  investments  included  other  investments  of  $148.8  million,  or  25.3%  of  our  total  investment  portfolio,  comprised  of  a
combination  of  private  credit  funds,  private  equity  funds,  other  privately  held  investments  and  investments  in  direct  lending  activities.  As  a  result  of  market
conditions prevailing at a particular time, the allocation of our portfolio to various asset types may vary. The fair market value of these assets and the investment
income from these assets will fluctuate depending on general economic and market conditions. We classify our fixed maturity investments as available-for-sale
("AFS") and therefore changes in the market value are reflected in our shareholders’ equity through accumulated other comprehensive income ("AOCI").

Our  Board  has  established  our  investment  policies,  including  the  purchase  of  affiliated  securities,  approved  by  the  Vermont  DFR,  and  our  executive
management is implementing our investment strategy with the assistance of our investment managers. Although these guidelines stress diversification and capital
preservation,  our  investment  results  will  be  subject  to  a  variety  of  risks,  including  risks  related  to  changes  in  the  business,  financial  condition  or  results  of
operations  of  the  entities  in  which  we  invest,  as  well  as  changes  in  general  economic  conditions  and  overall  market  conditions,  interest  rate  fluctuations  and
market volatility. Given our reliance on external investment managers, we are also exposed to operational risks, which may include, but are not limited to, a failure
of these managers to follow our investment policy guidelines, a failure to maintain proper internal controls, technological and staffing deficiencies and inadequate
disaster recovery plans.

A substantial portion of our investment portfolio consists of interest rate-sensitive instruments, such as bonds, which may be adversely affected by changes in

interest rates. Interest rates are highly sensitive to many factors, including governmental

18

monetary policies and domestic and international economic and political conditions and other factors beyond our control. Changes in interest rates could have an
adverse  effect  on  the  value  of  our  fixed  maturity  investment  portfolio  and  future  investment  income.  For  example,  changes  in  interest  rates  can  expose  us  to
prepayment  risks  on  U.S.  Government  Agency  MBS  included  in  our  investment  portfolio  (all  Agency  MBS  are  currently  "AA+"  rated  by  S&P).  Increases  in
interest rates will decrease the fair market value of our investments in fixed-income securities. If increases in interest rates occur during periods when we sell
investments  to  satisfy  liquidity  needs,  we  may  experience  investment  losses.  In  addition,  a  declining  interest  rate  environment  can  result  in  reductions  in  our
investment  yield  as  new  funds  and  proceeds  from  sales  and  maturities  of  fixed  income  securities  are  reinvested  at  lower  rates  which  reduces  our  overall
profitability.

Interest  rates  are  highly  sensitive  to  many  factors,  including  governmental  monetary  policies,  inflation,  domestic  and  international  economic  and  political
conditions and other factors beyond our control. To limit our exposure to unexpected interest rate increases which would reduce the value of our fixed income
securities and reduce our shareholders' equity, we attempt to maintain the duration of our fixed maturity investment portfolio combined with our cash and cash
equivalents, both restricted and unrestricted, within a reasonable range of the duration of our loss reserves. As a result of the LPT/ADC Agreement, the duration of
our  liability  for  loss  reserves  will  be  materially  shortened  and  if  we  do  not  correspondingly  shorten  the  duration  of  the  investments  in  our  fixed  maturity
investment portfolio, our risk of exposure to unexpected changes in interest rates could adversely affect our operations and financial condition.

At December 31, 2022 and 2021, these respective durations in years were as follows:

At December 31,
Fixed maturities and cash and cash equivalents
Reserve for loss and LAE - gross of LPT/ADC Agreement reserves
Reserve for loss and LAE - net of LPT/ADC Agreement reserves

2022

2021

1.3
5.3
1.1

1.5
4.4
1.4

The differential in duration between these assets and liabilities may fluctuate over time and in the case of fixed maturities, is affected by factors such as market

conditions, asset allocations and prepayment speeds in the case of Agency MBS.

We believe we have historically mitigated our exposure to liquidity risk through prudent duration management and strong operating cash flow. Our business
has undergone significant changes since 2019, which have transformed our operations and materially reduced the risk on our balance sheet. As a result, our gross
and  net  premiums  written  will  continue  to  be  materially  lower  going  forward  and  investment  income  will  continue  to  be  a  significantly  larger  portion  of  our
revenues. We believe this will significantly reduce our operating cash flow.

However,  we  generally  expect  negative  operating  cash  flows  to  be  met  or  exceeded  by  positive  investing  cash  flows.  Overall,  we  expect  our  cash  flows,
together with our existing capital base and unrestricted cash and investments to be sufficient to meet cash requirements and to operate our business. The LPT/ADC
Agreement  has  shortened  the  duration  of  our  liabilities,  which  in  turn  may  require  us  to  adjust  the  duration  of  our  fixed  maturities  which  could  lower  our
investment income. We also have very limited property catastrophe exposures which could cause an immediate need for cash. However, if we do not structure our
investment  portfolio  so  that  it  is  appropriately  matched  with  our  reinsurance  liabilities  or  our  operating  cash  flow  declines,  we  may  be  forced  to  liquidate
investments  prior  to  maturity  at  a  significant  loss  to  cover  such  liabilities.  For  this  or  any  of  the  other  reasons  discussed  above,  investment  losses  could
significantly  decrease  our  asset  base,  which  would  adversely  affect  our  ability  to  conduct  business.  Any  significant  decline  in  our  investment  income  would
adversely affect our business, financial condition and results of operations.

The  determination  of  the  fair  values  of  our  investments  and  whether  a  decline  in  the  fair  value  of  an  investment  is  other-than-temporary  are  based  on
management’s judgment and may prove to be incorrect.

We hold a significant amount of assets without readily available, active, quoted market prices or for which fair value cannot be measured from actively quoted
prices. These assets are generally deemed to require a higher degree of judgment used in measuring fair value. The assumptions used by management to measure
fair values could turn out to be inaccurate and the actual amounts that may be realized in an orderly transaction with a willing market participant could be either
lower or higher than our estimates of fair value. We review our investment portfolio for factors that may indicate that a decline in the fair value of an investment is
other-than-temporary. This evaluation is based on subjective factors, assumptions and estimates and may prove to be materially incorrect, which may result in us
recognizing additional losses in the future as new information emerges or recognizing losses in the current period that may never materialize in the future in an
orderly transaction with a willing market participant.

Our investments in alternative investments and our investments in joint ventures and/or entities accounted for using the equity method may be illiquid and
volatile in terms of value and returns, which could negatively affect our investment income and liquidity.

In addition to fixed maturity securities, we have invested, and may from time to time continue to invest, in alternative investments such as hedge funds, fixed
income funds, equity funds, privately held investments, private equity and private credit funds and co-investments, real estate funds and co-investments and other
alternative investments. During 2022, we increased the amount allocated to such investments, and at December 31, 2022, 43.0% of our total cash and investments
were categorized as equities, other investments and equity method Investments on our consolidated balance sheets compared to 25.4% as of December 31, 2021.
We expect to continue to increase this allocation over future periods and have committed $113.0 million to future investments as of December 31, 2022. These and
other similar investments may be illiquid due to restrictions on sales, transfers and redemption terms, may have different, more significant risk characteristics than
our investments in fixed maturity securities and may also have more volatile values and returns, all of which could negatively affect our investment income and
overall portfolio liquidity.

19

We  have  also  invested,  and  from  time  to  time  may  continue  to  make  investments  in  joint  ventures  and  in  other  entities  that  we  do  not  control.  In  these
investments,  many  of  which  are  accounted  for  using  the  equity  method,  we  may  lack  management  and  operational  control  over  the  entities  in  which  we  are
invested, which may limit our ability to take actions that could protect or increase the value of our investment. In addition, these investments may be illiquid due
to contractual provisions, and our lack of operational control may prevent us from obtaining liquidity through distributions from these investments in a timely
manner or on favorable terms.

Alternative or "other" investments may not meet regulatory admissibility requirements or may result in increased regulatory capital charges to our insurance
subsidiaries that hold these investments, which could limit those subsidiaries’ ability to make capital distributions to us and, consequently, negatively impact our
liquidity. For more information on our alternative investments, please see Item 7. "Management's Discussion & Analysis: Liquidity and Capital Resources - Cash
& Investments".

We may require additional capital in the future, which may not be available on favorable terms or at all.

Our future capital requirements will depend on many factors. We also may not be able to grow significantly without additional capital. Our future business
needs are uncertain and we may need to raise additional funds to further capitalize Maiden Reinsurance or our IIS business. We anticipate that any such additional
funds would be raised through equity, debt, hybrid financings or entering into reinsurance agreements. While we currently have no commitment from any lender
with  respect  to  a  credit  facility  or  a  loan  facility,  we  may  enter  into  an  unsecured  or  secured  revolving  credit  facility  or  a  term  loan  facility  with  one  or  more
syndicates of lenders. Any equity, debt or hybrid financing, if available at all, may be on terms that are not favorable to us. Recent turbulence in financial markets
due to higher interest rates along with tighter credit underwriting may limit our ability to access the credit or equity markets. If we are able to raise capital through
equity financings, the interest of shareholders in our Company would be diluted, and the securities we issue may have rights, preferences and privileges that are
senior to those of our common shares.

We no longer have an S&P rating or A.M. Best rating. The absence of credit ratings on our outstanding securities could impact our ability to obtain additional
debt or hybrid capital at reasonable terms or at all. Credit ratings are an opinion by third parties of our financial strength and ability to meet ongoing obligations to
our future policyholders.  The lack of a credit rating may make it difficult for investors to evaluate an investment in our securities and for us to raise additional
capital in the future on acceptable terms or at all. Similarly, our access to funds may be impaired if regulatory authorities take negative actions against us. Finally,
our operating results in the last several years may make investors reluctant to commit capital to us at reasonable valuations and/or pricing. Our internal sources of
liquidity may prove to be insufficient, and in such case, we may not be able to successfully obtain additional financing on favorable terms, or at all. Establishing a
credit rating on our securities, if needed in the future, may be difficult to obtain.

The availability of additional financing will also depend on a variety of other factors such as market conditions, the general availability of capital, the volume
of  trading  activities  and  the  overall  availability  of  capital  to  the  financial  services  industry.  As  such,  we  may  be  forced  to  delay  raising  capital,  issue  shorter
maturity securities than we prefer, or bear an unattractive cost of capital which could decrease our profitability and significantly reduce our financial flexibility. If
we cannot obtain adequate capital, our business prospects, results of operations and financial condition could be adversely affected.

We do not anticipate paying any cash dividends on our common shares for the foreseeable future.

We currently intend to retain our future earnings, if any, to strengthen our regulatory capital and solvency ratios, improve our liquidity and working capital and
for other general corporate purposes. The insurance laws and regulations of our insurance subsidiaries generally contain restrictions on the ability to pay dividends
or  distributions  to  Maiden  Holdings,  which  may  restrict  our  ability  to  pay  dividends  on  common  shares.  Any  capital  distribution  of  any  kind  out  of  Maiden
Reinsurance would be done consistent with Vermont regulation which requires the prior approval of the Vermont DFR. Any future determination to pay dividends
on our common shares will be at the discretion of our Board, subject to applicable laws, and will depend on our financial condition, results of operations, capital
requirements, general business conditions, and other factors that our Board considers relevant.

Our failure to comply with restrictive covenants contained in the documents governing our Senior Notes or any future credit facility could trigger prepayment
obligations, which could adversely affect our business, financial condition and results of operations.

The indentures governing our Senior Notes contain covenants that impose restrictions on us and certain of our subsidiaries with respect to, among other things,
the  incurrence  of  liens  and  the  disposition  of  capital  stock  of  these  subsidiaries.  In  addition,  any  future  credit  facility  may  require  us  and/or  certain  of  our
subsidiaries to comply with certain covenants, which may include the maintenance of a minimum consolidated net tangible worth and restrictions on the payment
of dividends. Our failure to comply with these covenants could result in an event of default under the indentures or any future credit facility, which, if not cured or
waived,  could  result  in  us  being  required  to  repay  the  notes  or  any  amounts  outstanding  under  such  credit  facility  prior  to  maturity.  We  believe  we  are  in
compliance with all of the covenants in the Indentures governing the Senior Notes. However, our business, financial condition and results of operations could be
adversely affected if we were found to be in default of these covenants.

For more details on our indebtedness, see “Management’s Discussion and Analysis of Financial Condition and Results of Operations" included under Item 7
and "Notes to Consolidated Financial Statements - "Note 7 — Long-Term Debt" included under Item 8. "Financial Statements and Supplementary Data" of this
Annual Report on Form 10-K.

We may be adversely impacted by claims inflation.

Our  operations,  like  those  of  other  property  and  casualty  insurers  and  reinsurers,  are  susceptible  to  the  effects  of  claims  inflation  because  premiums  are
established before the ultimate amounts of loss and LAE are known. Although we consider the potential effects of claims inflation when setting premium rates,
our premiums may not fully offset the effects of inflation and

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essentially result in our underpricing the risks we insure and reinsure. Our reserve for loss and LAE includes assumptions about future payments for settlement of
claims and claims handling expenses, such as the value of replacing property and associated labor costs for the property business we write, the value of medical
treatments and litigation costs. To the extent claims inflation causes these costs to increase above reserves established for these claims, we will be required to
increase our loss reserves with a corresponding reduction in our net income in the period in which the deficiency is identified, which may have a material adverse
effect on our financial condition or results of operations.

Climate change may adversely impact our results of operations and/or our financial position.

Global  climate  change  has  been  linked  to  a  number  of  factors  that  contribute  to  the  increased  unpredictability,  frequency,  duration  and  severity  of  weather
events, including changing weather patterns, a rise in ocean temperatures, and sea level rise. Global climate change and global climate change transitions could
lead to new or enhanced regulation, which may be difficult or costly to comply with, or impact assets that we invest in, which may result in realized and unrealized
losses in future periods that could have a material adverse impact on our results of operations and/or financial position. It is not possible to foresee the impacts of
potential future climate regulation, or which, if any, assets, industries or markets may be materially and adversely affected by global climate change and global
climate change transitions, nor is it possible to foresee the magnitude of such effects.

A decrease in the fair value of our subsidiaries may result in future impairments.

The determination of impairments taken on our investments and loans varies by type of asset and is based upon our periodic evaluation and assessment of
known  and  inherent  risks  associated  with  the  respective  asset  class.  Such  evaluations  and  assessments  are  revised  as  conditions  change  and  new  information
becomes  available.  Management  updates  its  evaluations  regularly  and  reflects  impairments  in  operations  as  such  evaluations  are  revised.  There  can  be  no
assurance that our management has accurately assessed the level of impairments taken in our financial statements. Furthermore, additional impairments may need
to  be  taken  in  the  future,  which  could  materially  impact  our  financial  position  or  results  of  operations.  Historical  trends  may  not  be  indicative  of  future
impairments.

Regulation

Compliance by our insurance subsidiaries with the legal and regulatory requirements to which they are subject is expensive. Any failure to comply could have
a material adverse effect on our business.

Our insurance subsidiaries are required to comply with a wide variety of laws and regulations applicable to insurance or reinsurance companies, both in the
jurisdictions in which they are organized and where they sell their insurance and reinsurance products. The insurance and regulatory environment has become
subject to increased scrutiny in many jurisdictions, including the U.S., various states within the U.S. and the EU. In the past, there have been Congressional and
other initiatives in the U.S. regarding increased supervision and regulation of the insurance industry. It is not possible to predict the future impact of changes in
laws and regulations on our operations. The cost of complying with any new legal requirements affecting our subsidiaries could have a material adverse effect on
our business.

In addition, our subsidiaries may not always be able to obtain or maintain necessary licenses, permits, authorizations or accreditations. They also may not be
able to fully comply with, or to obtain appropriate exemptions from, the laws and regulations applicable to them. Any failure to comply with applicable law or to
obtain appropriate exemptions could result in restrictions on either the ability of the company in question, as well as potentially its affiliates, to do business in one
or  more  of  the  jurisdictions  in  which  they  operate  or  on  brokers  on  which  we  rely  to  produce  business  for  us.  In  addition,  any  such  failure  to  comply  with
applicable laws or to obtain appropriate exemptions could result in the imposition of fines or other sanctions. Any of these sanctions could have a material adverse
effect on our business.

Our industry is highly regulated and we are subject to significant legal restrictions and these restrictions may have a material adverse effect on our business,
financial condition, results of operations, liquidity, cash flows and prospects.

The  financial  services  industry  is  the  focus  of  increased  regulatory  scrutiny  as  various  state  and  federal  governmental  agencies  and  self-regulatory
organizations conduct inquiries and investigations into the products and practices of the companies within this industry. Governmental authorities in the U.S. and
worldwide have become increasingly interested in potential risks posed by the insurance industry as a whole, and to commercial and financial systems in general.
Among the proposals that are being considered is the possible introduction of global regulatory standards for the amount of capital that insurance groups must
maintain across the group, such as the development of the risk-based global insurance capital standard for internationally active insurance groups being developed
by the International Association of Insurance Supervisors as well as the U.S. group capital calculation being developed by the NAIC. In 2021, the NAIC adopted
the final version of group capital calculation template and instructions and proposed revisions to the Insurance Holding Company System Act and Regulation to
implement the filing of the group capital calculation with the lead state insurance commissioner. This establishes a filing requirement for insurance groups for the
purposes of evaluating solvency at the group level. State legislatures and insurance departments have begun to implement the holding company system revisions
Please see Item 1. "Business - Regulatory Matters" for further discussion. While we cannot predict the exact nature, timing or scope of possible governmental
initiatives, there may be increased regulatory intervention in the insurance and financial services industry in the future.

Europe

Under EU Freedom of Services, a firm authorized in a European Economic Area ("EEA") state can offer certain products or services in other EEA states if it
has the relevant passport. Maiden LF and Maiden GF are established in an EEA state (Sweden) and have passports for a number of EEA states. Maiden LF is
licensed  by  the  Swedish  financial  regulator  (Finansinspektionen)  to  write  insurance  and  reinsurance  of  short-term  life  insurance  (Class  1a)  and  supplementary
insurance to Class 1a (Class 1b). Maiden GF is licensed by Finansinspektionen to write insurance and reinsurance of accident and sickness (Classes 1 and 2), other
property damage (Class 9) and other miscellaneous financial losses (Class 16). We cannot predict the impact laws and

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regulations adopted in the EU or other non-U.S. jurisdictions may have on the financial markets generally or on our businesses, results of operations or cash flows.
It  is  possible  that  changes  in  such  laws  and  regulations  may  alter  our  business  practices.  They  may  also  limit  our  ability  to  engage  in  capital  or  liability
management, require us to raise additional capital, and impose burdensome requirements and additional costs. It is possible that the laws and regulations adopted
in foreign jurisdictions will differ from one another, and that they could be inconsistent with the laws and regulations of other jurisdictions including the U.S.

United States

Our U.S. subsidiaries are subject to a complex and extensive array of laws and regulations that are administered and enforced by state insurance regulators,
state  securities  administrators,  state  banking  authorities,  the  SEC,  FINRA,  the  DOL,  the  IRS  and  the  Office  of  the  Comptroller  of  the  Currency.  See  Item  1.
“Business - Regulatory Matters” for a summary of certain U.S. state and federal laws and regulations applicable to our business. Failure to comply with these
laws and regulations could subject us to administrative penalties imposed by a particular governmental or self-regulatory authority, unanticipated costs associated
with remedying such failure or other claims, harm to our reputation, or interruption of our operations, any of which could have a material and adverse effect on our
capital, surplus, or other aspects of our financial position, results of operations and cash flows.

In addition, these statutes and regulations may, in effect, restrict the ability of our subsidiaries to write new business or, as indicated below, distribute funds to
Maiden  Holdings.  In  recent  years,  some  U.S.  state  legislatures  have  considered  or  enacted  laws  that  may  alter  or  increase  state  authority  to  regulate  insurance
companies  and  insurance  holding  companies.  Moreover,  the  NAIC  and  state  insurance  regulators  regularly  re-examine  existing  laws  and  regulations  and
interpretations of existing laws and develop new laws. The new interpretations or laws may be more restrictive or may result in higher costs to us than current
statutory requirements.

Changes in accounting principles and financial reporting requirements could result in material changes to our reported results of operations and financial
condition.

U.S.  GAAP  and  related  financial  reporting  requirements  are  complex,  continually  evolving  and  may  be  subject  to  varied  interpretation  by  the  relevant
authoritative bodies. Such varied interpretations could result from differing views related to specific facts and circumstances. Changes in U.S. GAAP and financial
reporting  requirements,  or  in  the  interpretation  of  U.S.  GAAP  or  those  requirements,  could  result  in  material  changes  to  our  reported  results  and  financial
condition.

Legislation enacted in Bermuda in response to the EU’s review of harmful tax competition could adversely affect our operations.

During 2017, the EU Economic and Financial Affairs Council released a list of non-cooperative jurisdictions for tax purposes. The stated aim of this list, and
accompanying report, was to promote good governance worldwide in order to maximize efforts to prevent tax fraud and tax evasion. Bermuda was not on the list
of non-cooperative jurisdictions but did feature in the report (along with approximately 40 other jurisdictions) as having committed to address concerns relating to
economic substance by December 31, 2018. In accordance with that commitment, Bermuda enacted the Economic Substance Act 2018 (as amended) of Bermuda
(the “ESA”) that came into force on January 1, 2019. As noted above under “Regulatory Matters – Certain Bermuda Law Regulations”, the ESA requires an in-
scope registered entity (other than an entity which is resident for tax purposes in certain jurisdictions outside Bermuda) that carries on as a business any one or
more of the “relevant activities” referred to in the ESA, to comply with economic substance requirements.

Under  the  ESA,  holding  entity  activities  (as  defined  in  the  ESA  and  the  Economic  Substance  Regulations  2018,  as  amended)  satisfy  the  requirement  of
undertaking a “relevant activity” and therefore would apply to Maiden Holdings. However, because Maiden Holdings’ primary function is to acquire and hold
shares or equitable interests in other entities and it does not perform any commercial activities, we believe we are only subject to the ESA’s minimum economic
substance requirements, and we file an annual declaration with the Registrar on that basis.

Even  as  a  pure  equity  holding  entity,  Maiden  Holdings  will  still  be  required  to  demonstrate  compliance  with  the  ESA  that  we  have  “adequate”  economic

substance in Bermuda, and therefore should have adequate people for holding and managing equity participation, and adequate premises in Bermuda.

Given that the legislation is new and remains subject to further clarification and interpretation, the meaning of "adequate" in this context remains unclear. It is
not currently possible to ascertain the steps required to ensure our continued compliance with the ESA, which makes it difficult to predict its future impact. Any
entity that must satisfy economic substance requirements but fails to do so could face financial penalties or could be ordered by a court to take action to remedy
such failure. It may also be faced with a restriction of its business activities, automatic reporting by the Bermuda authorities to competent authorities in the EU on
an entity's non-compliance or may be struck off as a registered entity in Bermuda. If any one of the foregoing were to occur, it may adversely impact the business
operations of Maiden Holdings.

Corporate Governance and Risks Related to an Investment in our Securities

Our holding company structure and certain regulatory and other constraints affect our ability to pay dividends and make other payments.

Maiden Holdings is a holding company. As a result, we do not have, and will not have, any significant operations or assets other than our ownership of the
shares  of  our  subsidiaries.  We  expect  that  dividends  and  other  permitted  distributions  from  Maiden  Global  (and  its  subsidiaries),  Maiden  LF,  Maiden  GF  and
Maiden NA (and its subsidiaries) will be our sole source of funds to pay any dividends to common shareholders and meet ongoing cash requirements, including
debt service payments, if any, and other expenses. The jurisdictions in which our operating subsidiaries are licensed to write business impose regulations requiring
companies to maintain or meet statutory solvency and liquidity requirements and also place restrictions on the declaration and payment of dividends and other
distributions. The inability of our subsidiaries to pay dividends in an amount

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sufficient to enable us to meet our cash requirements at the holding company level could have a material adverse effect on our business, financial condition and
results of operations. Any capital distribution of any kind out of Maiden Reinsurance requires the prior approval of the Vermont DFR.

The timing and amount of any cash dividends on our common shares are at the discretion of our Board and will depend upon the results of operations and cash

flows, our financial position and capital requirements, and any other factors that our Board deems relevant.

We have risks related to the Company’s Senior Notes.

Maiden NA issued the 2013 Senior Notes and Maiden Holdings issued the 2016 Senior Notes, both of which are currently outstanding. We may be dependent
on dividends from Maiden Reinsurance, which required regulatory approval, to provide cash flows to pay interest on both the 2013 Senior Notes and the 2016
Senior Notes. If we are unable to maintain a level of cash flows from operating and investment activities, our ability to pay our obligations on our Senior Notes
could be adversely affected.

We may also incur additional indebtedness in the future. The level of debt outstanding could adversely affect our financial flexibility. Our indebtedness could

have adverse consequences, including:

•

•

•

•

•

•

•

limiting our ability to pay dividends to our common shareholders;

limiting our subsidiaries’ ability to pay dividends;

increasing our vulnerability to changing economic, regulatory and industry conditions;

limiting our ability to compete and our flexibility in planning for, or reacting to, changes in our business and the industry;

limiting our ability to borrow additional funds;

requiring us to dedicate a substantial portion of our cash flow from operations to payments on our debt, thereby, reducing funds available for working
capital, capital expenditures, acquisitions and other purposes; and

impacting  regulators  assessment  of  our  capital  position,  adequacy  and  flexibility  and  therefore,  the  financial  strength  ratings  of  rating  agencies  and
regulators' assessment of our solvency.

Maiden Reinsurance owns 29% of our total outstanding common shares and thus has a significant ownership and voting stake in our common shares.

As a result of the exchange of our previously outstanding preference shares for our common shares on December 27, 2022, Maiden Reinsurance owns 29% of
our total outstanding common shares and subject to our bye-laws, has the ability to vote up to 9.5% of these shares. As our wholly owned subsidiary, Maiden
Reinsurance’s economic and voting interests in our common shares may not be aligned with other shareholders and it could take positions that may differ from,
and which could adversely affect the interests of, other shareholders.

Our common shares owned by Maiden Reinsurance are not retired and could be sold to other shareholders, which could dilute the ownership interests  of
other shareholders and reduce our book value and earnings per common share.

For the purposes of our consolidated financial statements, our common shares owned by Maiden Reinsurance are treated similar to treasury shares and not
included in the computation of consolidated book value and earnings per common share. However, these shares are not retired and Maiden Reinsurance retains
both economic and voting interests in our shares (subject to limitations in our bye-laws, Maiden Reinsurance has a 9.5% voting interest in our common shares).
Maiden Reinsurance thus retains the ability to sell those shares in the open market or through privately negotiated transactions, subject to applicable securities
laws  and  regulations.  If  Maiden  Reinsurance  were  to  engage  in  such  transactions,  then  the  number  of  outstanding  shares  for  consolidated  financial  reporting
purposes would increase and thus reduce our book value and earnings per common share.

A  few  significant  shareholders  may  influence  or  control  the  direction  of  our  business.  If  the  ownership  of  our  common  shares  continues  to  be  highly
concentrated, it may limit your ability and the ability of other shareholders to influence significant corporate decisions.

The interests of our significant shareholders may not be fully aligned with our interests, and this may lead to a strategy that is not in our best interest. Although
they do not have any voting agreements or arrangements, our Founding Shareholders or other significant shareholders could exercise significant influence over
matters requiring shareholder approval, and their concentrated holdings may delay or deter possible changes in control of Maiden Holdings, which may reduce the
market price of our common shares.

Our revenues and results of operations may fluctuate as a result of factors beyond our control, which may cause the price of our shares to be volatile.

The revenues and results of operations of reinsurance companies historically have been subject to significant fluctuations and uncertainties. In addition, we are
not  currently  engaged  in  reinsurance  underwriting  of  new  prospective  risks  and  may  not  do  so  for  the  foreseeable  future.  This  has  resulted  in  a  significant
reduction in our revenues. Our profitability can also be affected significantly by:

•

•

fluctuations in interest rates, inflationary pressures and other changes in the investment environment that impact returns on invested assets;

changes in the frequency or severity of claims;

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• volatile and unpredictable developments, including man-made, weather-related and other natural catastrophes, terrorist attacks or pandemics, such as the

spread of the COVID-19 virus;

• price competition;

•

•

inadequate loss and LAE reserves;

cyclical nature of the property and casualty insurance market; and

• negative developments in the specialty property and casualty reinsurance sectors in which we operate.

These factors may cause the price of the Company's shares to be volatile.

The market price for our common shares has been and may continue to be highly volatile, and if there is a further sustained decline in our share price there
could be limited liquidity for our common shares.

The market price for our common shares has fluctuated significantly. Future sales of our common shares by our shareholders or us, or the perception that such
sales  may  occur,  could  adversely  affect  the  market  price  of  our  common  shares.  As  of  March  8,  2023,  101,532,151  common  shares  were  outstanding  as  the
41,439,348 common shares issued to Maiden Reinsurance in the Exchange are reflected as treasury shares on the Consolidated Balance Sheet and are not treated
as  outstanding  shares  in  the  computation  of  consolidated  book  value  and  earnings  per  common  share  on  December  31,  2022.  A  significant  percentage  of  our
outstanding common shares are held by affiliates, including Maiden Reinsurance, and as a result, your common shares may not have sufficient liquidity in the
trading markets.

In addition, we have reserved 7,681,477 common shares for issuance under our 2019 Omnibus Incentive Plan. As of March 8, 2023, there were 141,000 stock
options  outstanding  and  492,463  restricted  shares  outstanding.  Sales  of  substantial  amounts  of  our  shares,  or  the  perception  that  such  sales  could  occur,  could
adversely affect the prevailing price of the shares and may make it more difficult for us to sell our equity securities in the future, or for shareholders to sell their
shares, at a time and price that they deem appropriate.

Provisions in our bye-laws may reduce or increase the voting rights of our shares.

In general, and except as provided under our bye-laws and as provided below, the common shareholders have one vote for each common share held by them
and  are  entitled  to  vote,  on  a  non-cumulative  basis,  at  all  meetings  of  shareholders.  However,  if,  and  so  long  as,  the  shares  of  a  shareholder  are  treated  as
"controlled shares" (as determined pursuant to Sections 957 and 958 of the Internal Revenue Code of 1986, as amended (the "IRS Code")) of any U.S. Person (as
that term is defined in the Risk Factors under the section captioned "Taxation" within this Item that owns shares directly or indirectly through non-U.S. entities)
and such controlled shares constitute 9.5% or more of the votes conferred by our issued shares, the voting rights with respect to the controlled shares owned by
such  U.S.  Person  will  be  limited,  in  the  aggregate,  to  a  voting  power  of  less  than  9.5%,  under  a  formula  specified  in  our  bye-laws.  The  formula  is  applied
repeatedly until the voting power of all 9.5% U.S. Shareholders has been reduced to less than 9.5%. In addition, our Board may limit a shareholder’s voting rights
when  it  deems  it  appropriate  to  do  so  to  (i)  avoid  the  existence  of  any  9.5%  U.S.  Shareholder;  and  (ii)  avoid  certain  material  adverse  tax,  legal  or  regulatory
consequences to us, to any of our subsidiaries or any direct or indirect shareholder or its affiliates. "Controlled shares" include, among other things, all shares that
a U.S. Person is deemed to own directly, indirectly or constructively (within the meaning of section 958 of the IRS Code). The amount of any reduction of votes
that occurs by operation of the above limitations will generally be reallocated proportionately among our other shareholders whose shares were not "controlled
shares" of the 9.5% U.S. Shareholder so long as such reallocation does not cause any person to become a 9.5% U.S. Shareholder.

Under these provisions, certain shareholders may have their voting rights limited, while other shareholders may have voting rights in excess of one vote per
share. Subject to limitations in our bye-laws, Maiden Reinsurance will be limited to a 9.5% voting interest in our common shares. Moreover, these provisions
could  have  the  effect  of  reducing  the  votes  of  certain  shareholders  who  would  not  otherwise  be  subject  to  the  9.5%  limitation  by  virtue  of  their  direct  share
ownership.

We are authorized under our bye-laws to request information from any shareholder for the purpose of determining whether a shareholder’s voting rights are to
be reallocated under the bye-laws. If any holder fails to respond to this request or submits incomplete or inaccurate information, we may, in our sole discretion,
eliminate or adjust the shareholder’s voting rights.

Anti-takeover provisions in our bye-laws could impede an attempt to replace or remove our directors, which could diminish the value of our common shares.

Our bye-laws contain provisions that may entrench directors and make it more difficult for shareholders to replace directors even if the shareholders consider it
beneficial  to  do  so.  In  addition,  these  provisions  could  delay  or  prevent  a  change  of  control  that  a  shareholder  might  consider  favorable.  For  example,  these
provisions may prevent a shareholder from receiving the benefit from any premium over the market price of our common shares offered by a bidder in a potential
takeover. Even in the absence of an attempt to effect a change in management or a takeover attempt, these provisions may adversely affect the prevailing market
price of our common shares if they are viewed as discouraging changes in management and takeover attempts in the future.

Examples of provisions in our bye-laws that could have such an effect include the following:

• our Board may reduce the total voting power of any shareholder to avoid adverse tax, legal or regulatory consequences to us or any direct or indirect

holder of our shares or its affiliates; and

• our Board may, in their discretion, decline to record the transfer of any common shares on our share register, if they are not satisfied that all required

regulatory approvals for such transfer have been obtained or if they determine such

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transfer may result in a non-de minimis adverse tax, legal or regulatory consequence to us or any direct or indirect holder of shares or its affiliates.

It may be difficult for a third party to acquire us.

Provisions of our organizational documents may discourage, delay or prevent a merger, amalgamation, tender offer or other change of control that holders of
our shares may consider favorable. These provisions impose various procedural and other requirements that could make it more difficult for shareholders to affect
various corporate actions. These provisions could:

• have the effect of delaying, deferring or preventing a change in control of us;

• discourage bids for our securities at a premium over the market price;

•

•

adversely affect the price of, and the voting and other rights of the holders of our securities; or

impede the ability of the holders of our securities to change our management.

U.S. persons who own our shares may have more difficulty in protecting their interests than U.S. persons who are shareholders of a U.S. corporation.

The  Companies  Act  in  Bermuda,  which  applies  to  us,  differs  in  certain  material  respects  from  laws  generally  applicable  to  U.S.  corporations  and  their
shareholders. As a result of these differences, U.S. persons who own our shares may have more difficulty protecting their interests than U.S. persons who own
shares of a U.S. corporation. Set forth below is a summary of certain significant provisions of the Companies Act, including modifications adopted pursuant to our
bye-laws, applicable to us, which differ in certain respects from provisions of Delaware corporate law. Because the following statements are summaries, they do
not discuss all aspects of Bermuda law that may be relevant to us and our shareholders.

Interested Directors. Bermuda law provides that if a director has a personal interest in a transaction to which the company is also a party and if the director
discloses the nature of this personal interest at the first opportunity, either at a meeting of directors or in writing to the directors, then the company will not be able
to declare the transaction void solely due to the existence of that personal interest and the director will not be liable to the company for any profit realized from the
transaction. In addition, Bermuda law and our bye-laws provide that, after a director has made the declaration of interest referred to above, he is allowed to be
counted for purposes of determining whether a quorum is present and to vote on a transaction in which he has an interest, unless disqualified from doing so by the
chairman of the relevant board meeting.

Under Delaware law, such transaction would not be voidable if:

•

•

•

•

the material facts as to such interested director’s relationship or interests are disclosed or are known to the board of directors and the board in good faith
authorizes the transaction by the affirmative vote of a majority of the disinterested directors;

such material facts are disclosed or are known to the shareholders entitled;

to vote on such transaction and the transaction is specifically approved in good faith by vote of the majority of shares entitled to vote thereon; or

the transaction is fair as to the corporation as of the time it is authorized, approved or ratified.

Under Delaware law, such interested director could be held liable for a transaction in which such director derived an improper personal benefit.

Mergers and Similar Arrangements. The amalgamation or merger of a Bermuda company with another company or corporation (other than certain affiliated
companies) requires the amalgamation agreement to be approved by the company’s board of directors and by its shareholders. Under our bye-laws, we may, with
the  approval  of  a  majority  of  votes  cast  at  a  general  meeting  of  our  shareholders  at  which  a  quorum  is  present,  amalgamate  or  merge  with  another  Bermuda
company or with a body incorporated outside Bermuda. In the case of an amalgamation or merger, a shareholder that did not vote in favor of the amalgamation or
merger may apply to a Bermuda court for a proper valuation of such shareholder’s shares if such shareholder is not satisfied that fair value has been paid for such
shares. Under Delaware law, with certain exceptions, a merger, consolidation or sale of all or substantially all the assets of a corporation must be approved by the
board of directors and a majority of the outstanding shares entitled to vote thereon. Under Delaware law, a shareholder of a corporation participating in certain
major corporate transactions may, under certain circumstances, be entitled to appraisal rights pursuant to which such shareholder may receive cash in the amount
of the fair value of the shares held by such shareholder (as determined by a court) in lieu of the consideration such shareholder would otherwise receive in the
transaction.

Shareholders’ Suit. The rights of shareholders under Bermuda law are not as extensive as the rights of shareholders under legislation or judicial precedent in
many U.S. jurisdictions. Class actions and derivative actions are generally not available to shareholders under the laws of Bermuda. However, the Bermuda courts
ordinarily would be expected to follow English case law precedent, which would permit a shareholder to commence an action in the name of the company to
remedy a wrong done to the company where the act complained of is alleged to be beyond the corporate power of the company, is illegal or would result in the
violation of our memorandum of association or bye-laws. Furthermore, consideration would be given by the court to acts that are alleged to constitute a fraud
against the minority shareholders or where an act requires the approval of a greater percentage of our shareholders than actually approved it. The winning party in
such an action generally would be able to recover a portion of attorneys’ fees incurred in connection with such action. Our bye-laws provide that shareholders
waive all claims or rights of action that they might have, individually or in the right of the company, against any director or officer for any act or failure to act in
the performance of such director’s or officer’s duties, except with respect to any fraud or dishonesty of such director or officer. Class actions and derivative actions
generally are available to shareholders under Delaware law for,

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among other things, breach of fiduciary duty, corporate waste and actions not taken in accordance with applicable law. In such actions, the court has discretion to
permit the winning party to recover attorneys’ fees incurred in connection with such action.

Indemnification of Directors. We may indemnify our directors or officers in their capacity as directors or officers of any loss arising or liability attaching to
them by virtue of any rule of law in respect of any negligence, default, breach of duty or breach of trust of which a director or officer may be guilty in relation to
the company other than in respect of his or her own fraud or dishonesty. Under Delaware law, a corporation may indemnify a director or officer of the corporation
against  expenses  (including  attorneys’  fees),  judgments,  fines  and  amounts  paid  in  settlement  actually  and  reasonably  incurred  in  defense  of  an  action,  suit  or
proceeding by reason of such position if such director or officer acted in good faith and in a manner he or she reasonably believed to be in or not opposed to the
best  interests  of  the  corporation  and,  with  respect  to  any  criminal  action  or  proceeding,  such  director  or  officer  had  no  reasonable  cause  to  believe  his  or  her
conduct was unlawful. In addition, we have entered into indemnification agreements with our directors and officers.

We are a Bermuda company, and it may be difficult to enforce judgments against us or our directors and executive officers.

We are incorporated under the laws of Bermuda and our holding company is based in Bermuda. In addition, all of our directors and officers reside outside
Bermuda and a substantial portion of our assets will be and the assets of these persons are, and will continue to be, located in jurisdictions outside Bermuda. As
such, it may be difficult or impossible to effect service of process within the U.S. upon us or those persons or to recover against us or them on judgments of U.S.
courts, including judgments predicated upon civil liability provisions of the U.S. federal securities laws. Further, no claim may be brought in Bermuda against us
or our directors and officers in the first instance for violation of U.S. federal securities laws because these laws have no extraterritorial jurisdiction under Bermuda
law and do not have force of law in Bermuda. A Bermuda court may, however, impose civil liability, including the possibility of monetary damages, on us or our
directors and officers if the facts alleged in a complaint constitute or give rise to a cause of action under Bermuda law.

We have been previously advised by Conyers Dill & Pearman Limited, our Bermuda counsel, that there is doubt as to whether the courts of Bermuda would
enforce judgments of U.S. courts obtained in actions against us or our directors and officers, as well as the experts named in this Annual Report, predicated upon
the civil liability provisions of the U.S. federal securities laws or original actions brought in Bermuda against us or these persons predicated solely upon U.S.
federal  securities  laws.  Further,  we  have  been  advised  by  Conyers  Dill  &  Pearman  Limited  that  there  is  no  treaty  in  effect  between  the  U.S.  and  Bermuda
providing for the enforcement of judgments of U.S. courts, and there are grounds upon which Bermuda courts may not enforce judgments of U.S. courts. Some
remedies available under the laws of U.S. jurisdictions, including some remedies available under the U.S. federal securities laws, may not be allowed in Bermuda
courts as contrary to that jurisdiction’s public policy. Because judgments of U.S. courts are not automatically enforceable in Bermuda, it may be difficult for you to
recover against us based upon such judgments.

Employee Issues

We are dependent on our key executives. We may not be able to attract and retain key employees or successfully implement our business strategy.

Our success depends largely on our senior management, which includes, among others, Lawrence F. Metz, our President and Co-Chief Executive Officer, and
Patrick J. Haveron, our Co-Chief Executive Officer and Chief Financial Officer (Messrs. Metz and Haveron are referred to as the "Co-CEOs"). We have entered
into employment agreements with these executive officers.

In addition to the officers listed above, we require key staff with actuarial, legal, reinsurance, accounting and administrative skills. We have a significantly
smaller  staff  and  given  our  current  business  circumstances,  and  it  may  be  difficult  for  us  to  retain  staff  and  recruit  competent  new  executives  and  staff.  Our
inability to attract and retain additional personnel or the loss of the services of any of our senior executives or key employees could delay or prevent us from fully
implementing our business strategy and could significantly and negatively affect our business.

Our business in Bermuda could be adversely affected by Bermuda employment restrictions.

Currently, Maiden Holdings employs seven non-Bermudians who are work permit holders in our Bermuda office including our Co-CEOs. Under Bermuda law,
non-Bermudians  (other  than  spouses  of  Bermudians  and  holders  of  permanent  residents’  certificates)  may  not  engage  in  any  gainful  occupation  in  Bermuda
without a valid government work permit. A work permit may be granted or renewed upon showing that, after proper public advertisement, no Bermudian, spouse
of a Bermudian, or holder of a permanent resident’s or working resident’s certificate who meets the minimum standards reasonably required by the employer has
applied for the job. Work permits are issued with expiry dates that range from one, two, three, four and five years. A waiver from advertising is automatically
granted in respect of any chief executive officer position and other chief officer positions. We may not be able to use the services of one or more of our non-
Bermudian employees if we are not able to obtain work permits for them, which could have a material adverse effect on our business, financial condition and
results of operations.

International Operations

Our offices that operate in jurisdictions outside Bermuda and the U.S. are subject to certain limitations and risks that are unique to foreign operations.

Our  international  operations  are  regulated  in  various  jurisdictions  with  respect  to  licensing  requirements,  currency,  reserves,  employees  and  other  matters.
International operations may be harmed by political developments in foreign countries, which may be hard to predict in advance. Regulations governing technical
reserves and remittance balances in some countries may hinder remittance of profits and repatriation of assets.

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The U.K.'s exit from the EU could adversely affect us.

The UK left the EU on January 31, 2020. Maiden LF and Maiden GF have established UK branches to enable us to continue underwriting in the UK post-
Brexit. Maiden LF, UK Branch and Maiden GF, UK Branch were authorized by the Prudential Regulatory Authority and Financial Conduct Authority on May 30,
2022 and May 12, 2022 respectively. As a result, our regulatory compliance oversight and reporting requirements have increased.

The risks associated with the potential consequences that may follow Brexit, including volatility in financial markets, exchange rates and interest rates, remain
uncertain. These uncertainties could increase the volatility of, or adversely affect, our investment results in particular periods or over time. Brexit could adversely
affect European or worldwide political, regulatory, economic or market conditions and could contribute to instability in global political institutions and regulatory
agencies which, in turn, could adversely affect our business, results of our operations and our financial condition.

Foreign currency fluctuations may reduce our net income and our capital levels, adversely affecting our financial condition.

We conduct business in a variety of non-U.S. currencies, the principal exposures being the euro and the British pound. Assets and liabilities denominated in
foreign currencies are exposed to changes in currency exchange rates. Our reporting currency is the U.S. dollar, and exchange rate fluctuations relative to the U.S.
dollar may materially impact our results of operations and financial position. Our principal exposure to foreign currency risk is our obligation to settle claims in
foreign currencies. In addition, we maintain and expect to continue to maintain a portion of our investment portfolio in investments denominated in currencies
other than the U.S. dollar. While the Company may be able to match its foreign currency denominated assets against its net reinsurance liabilities both by currency
and duration to protect the Company against foreign exchange and interest rate risks, a natural offset does not exist for all currencies.

We may employ various strategies (including hedging) to manage our exposure to foreign currency exchange risk. To the extent that these exposures are not
fully hedged or the hedges are ineffective, our results or equity may be reduced by fluctuations in foreign currency exchange rates that could materially adversely
affect our financial condition and results of operations. At December 31, 2022, no such hedges or hedging strategies were in force or had been entered into.

Relationship with AmTrust

Significant  changes  in  our  reinsurance  relationship  with  AmTrust  have  reduced  our  current  and  future  revenues  and  create  significant  uncertainty  for
sources of future liquidity.

During  2019,  we,  through  our  subsidiary  Maiden  Reinsurance,  executed  the  partial  termination  amendment  ("Partial  Termination  Amendment")  effective
January  1,  2019  which  amended  the  AmTrust  Quota  Share,  the  Final  AmTrust  QS  Terminations,  the  AmTrust  WC  Commutation  and  several  post-termination
endorsements. These transactions served to eliminate all new premium revenues from AmTrust, return certain unearned premiums to AmTrust, commuted and
returned certain workers’ compensation loss reserves to AmTrust, capped the loss corridor on certain program business reinsured from AmTrust and increased the
levels of collateral provided to AmTrust as security against the obligations the Company has assumed under the reinsurance contracts with AmTrust.

While  these  transactions  have  contributed  significantly  to  the  reduction  in  required  regulatory  capital  needed  to  operate  our  business  and  the  subsequent
strengthening  of  our  capital  and  solvency  ratios,  these  transactions  have  resulted  in  a  significant  reduction  in  revenues  which  is  likely  to  continue  for  the
foreseeable future as we are not presently engaged in active reinsurance underwriting on prospective risks. As a result, our financial condition could be adversely
affected  by  these  actions.  Due  to  this  loss  of  revenue,  we  will  need  to  rely  on  unrestricted  cash  from  operations  and  returns  on  our  investments  to  fund  our
operations,  maintain  liquidity  and  meet  our  financial  obligations  and  capital  allocation  priorities.  While  we  believe  we  have  sufficient  sources  to  meet  these
obligations, deterioration in our results of operations or other adverse financial events could impact our ability to continue meeting these obligations.

Our  initial  arrangements  with  AmTrust  were  negotiated  while  we  were  its  affiliate.  The  arrangements  could  be  challenged  as  not  reflecting  terms  that  we
would  agree  to  in  arm’s-length  negotiations  with  an  independent  third  party;  moreover,  our  business  relationship  with  AmTrust  and  its  subsidiaries  may
present, and may make us vulnerable to, possible adverse tax consequences, difficult conflicts of interest, and legal claims that we have not acted in the best
interest of our shareholders.

Effective July 1, 2007, we entered into a quota share agreement with AII, which reinsures AmTrust’s insurance company subsidiaries, and a master agreement
with  AmTrust,  as  amended  ("Master  Agreement"),  pursuant  to  which  Maiden  Reinsurance  and  AII  entered  into  the  AmTrust  Quota  Share.  Because  Leah
Karfunkel  (wife  of  the  late  Michael  Karfunkel),  George  Karfunkel  and  Barry  Zyskind  (the  Company's  non-executive  chairman)  collectively  own  or  control
approximately 55.2% of the outstanding common shares of Evergreen Parent, L.P., the ultimate parent of AmTrust, and our Founding Shareholders sponsored our
formation,  we  may  be  deemed  to  be  an  affiliate  of  AmTrust.  Leah  Karfunkel  (wife  of  the  late  Michael  Karfunkel),  George  Karfunkel  and  Barry  Zyskind  (the
Company's non-executive chairman) each own or control less than 5.0% of the outstanding shares of the Company based on their most recent individual public
filings. Due to our close business relationship with AmTrust, we may be presented with situations involving conflicts of interest with respect to the agreements
and  other  arrangements  we  will  enter  into  with  AmTrust  and  its  subsidiaries,  exposing  us  to  possible  claims  that  we  have  not  acted  in  the  best  interest  of  our
shareholders. The arrangements between us and AmTrust were modified after they were originally entered into and there could be future modifications.

Our  non-executive  Chairman  of  the  Board  currently  holds  the  positions  of  Chief  Executive  Officer  and  Chairman  of  AmTrust.  These  dual  positions  may
present, and make us vulnerable to, difficult conflicts of interest and related legal challenges.

Barry Zyskind, our non-executive Chairman of the Board, is the Chief Executive Officer and Chairman of the Board of AmTrust and, as such, he does not
serve our Company on a full-time basis. Mr. Zyskind is expected to continue in both of his positions for the foreseeable future. Conflicts of interest could arise
with respect to business opportunities that could be

27

advantageous to AmTrust or its subsidiaries, on the one hand, and us or our subsidiary, on the other hand. In addition, potential conflicts of interest may arise
should the interests of the Company and AmTrust diverge. However, the Audit Committee of our Board, which consists entirely of independent directors, does
exclusively review and approve all related party transactions.

The amount of collateral we provide to AmTrust could limit our unrestricted liquidity and impact our ability to fulfill our obligations in certain circumstances.

As a result of our use of trust accounts, funds withheld, letters of credit and a loan, a substantial portion of our assets will not be available to us for other uses,
which could reduce our financial flexibility and could impact our ability to fulfill our obligations in certain circumstances. If further collateral is required to be
provided to any other AmTrust subsidiaries under applicable law or regulatory requirements, Maiden Reinsurance will provide collateral to the extent required.

At December 31, 2022, we provided $820.4 million of collateral to AmTrust, AII and AEL in the form of trusts, letters of credit, funds withheld and a loan.
This collateral includes $416.8 million transferred to AmTrust from existing trust accounts used for collateral on the AmTrust Quota Share to a funds withheld
arrangement in January 2019, which currently has an annual interest rate of 2.1%, subject to annual adjustment. The annual interest rate was 1.8% for the duration
of 2021.

Maiden  Reinsurance  is  not  a  party  to  the  reinsurance  agreements  between  AII  and  AmTrust’s  U.S.  insurance  subsidiaries  or  the  related  reinsurance  trust
agreements  and  has  no  rights  thereunder.  If  one  or  more  of  these  AmTrust  subsidiaries  withdraws  Maiden  Reinsurance’s  assets  from  their  trust  account  or
misapplies  withheld  funds  that  are  due  to  Maiden  Reinsurance  and  that  subsidiary  is  or  becomes  insolvent,  we  believe  it  may  be  more  difficult  for  Maiden
Reinsurance to recover any such amounts to which we are entitled than it would be if Maiden Reinsurance had entered into reinsurance and trust agreements with
these AmTrust subsidiaries directly. AII has agreed to immediately return to Maiden Reinsurance any collateral provided by Maiden Reinsurance that one of those
subsidiaries  improperly  utilizes  or  retains,  and  AmTrust  has  agreed  to  guarantee  AII’s  repayment  obligation  and  AII’s  payment  obligations  under  its  loan
agreement with Maiden Reinsurance. We are subject to the risk that AII and/or AmTrust may be unable or unwilling to discharge these obligations.

Insurance and Reinsurance Markets

The property and casualty insurance and reinsurance industry is cyclical in nature, which may affect our overall financial performance.

Historically,  the  financial  performance  of  the  property  and  casualty  insurance  and  reinsurance  industry  has  tended  to  fluctuate  in  cyclical  periods  of  price
competition and excess capacity (known as a soft market) followed by periods of high premium rates and shortages of underwriting capacity (known as a hard
market).  Although  the  financial  performance  of  an  individual  insurance  or  reinsurance  company  is  dependent  on  its  own  specific  business  characteristics,  the
profitability of most property and casualty insurance and reinsurance companies tends to follow this cyclical market pattern.

In recent years, the market has been in a competitive environment in which underwriting capacity has expanded, risk selection became less disciplined and
price competition increased sharply. During that period, market participants' capital levels have continued to improve due to positive earnings and improved values
of risk assets over that time. In addition, an influx of new market participants with different operating models than traditional reinsurers such as us have entered
the market place. While many of these new market participants specialize in property catastrophe oriented business and do not directly compete with us, they are
influencing competitive conditions in the broader reinsurance market. This additional underwriting capacity resulted in increased competition from other insurance
and reinsurance companies expanding the types or amounts of business they write, or from companies seeking to maintain or increase market share at the expense
of underwriting discipline.

Because this cyclicality is due in large part to the actions of our competitors and general economic factors beyond our control, we cannot predict with certainty
the  timing  or  duration  of  changes  in  the  market  cycle.  These  cyclical  patterns,  the  actions  of  our  competitors,  and  general  economic  factors  could  cause  our
revenues and net income to fluctuate, which may cause the price of our common shares to be volatile. The ultimate outcome of these events and their market
impact is not known at this time.

Negative developments in the U.S. workers’ compensation insurance industry could adversely affect our financial condition and results of operations.

Approximately 37.1% of our AmTrust Reinsurance segment's reserve for loss and LAE at December 31, 2022 was related to the reinsurance of U.S. workers'
compensation risks which is our largest exposure to a particular line of business. Our AmTrust Reinsurance segment includes all business ceded by AmTrust to
Maiden Reinsurance, primarily the AmTrust Quota Share and the European Hospital Liability Quota Share. Both contracts in this segment have been terminated
effective  January  1,  2019.  Negative  developments  in  the  economic,  competitive  or  regulatory  conditions  affecting  the  U.S.  workers’  compensation  insurance
industry could have an adverse effect on our financial condition and results of operations. For example, if legislators in our larger markets were to enact legislation
to  increase  the  scope  or  amount  of  benefits  for  employees  under  U.S.  workers’  compensation  insurance  policies  without  related  loss  control  measures,  or  if
regulators  made  other  changes  to  the  regulatory  system  governing  U.S.  workers’  compensation  insurance,  this  could  negatively  affect  the  U.S.  workers’
compensation insurance industry in the affected markets.

Reinsurance is a highly competitive industry.

The reinsurance industry is highly competitive. While we are not currently engaged in active reinsurance underwriting of new prospective risks, we are writing
risks  on  a  retroactive  basis  and  compete  with  major  U.S.  and  non-U.S.  reinsurers,  including  other  Bermuda-based  reinsurers,  on  an  international  and  regional
basis. Many of these entities have significantly larger amounts of capital, higher ratings from rating agencies and more resources than us. We currently do not have
a  financial  strength  or  credit  rating  from  S&P  or  A.M.  Best  and  the  lack  of  such  ratings  will  likely  limit  the  opportunities  we  have  to  write  new  reinsurance
business  if  we  resume  active  underwriting  of  new  prospective  risks.  Historically,  periods  of  increased  capacity  levels  in  our  industry  have  led  to  increased
competition which puts pressure on reinsurance pricing.

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In recent years, significant increases in the use of risk-linked securities and derivative and other non-traditional risk transfer mechanisms and vehicles are being
developed and offered by other parties, including entities other than insurance and reinsurance companies. The availability of both these non-traditional products
and  sources  of  capital  could  reduce  the  demand  for  traditional  insurance  and  reinsurance,  and  if  we  were  to  resume  active  reinsurance  underwriting  of  new
prospective  risks,  it  may  result  in  fewer  contracts  written,  lower  premium  rates,  increased  expenses  for  customer  acquisition  and  retention  and  less  favorable
policy terms and conditions, which could have a material adverse impact on our growth and profitability.

Consolidation in the insurance and reinsurance industry and increased competition on premium rates could lead to lower margins for us and less demand for
our products and services if and when we resume active reinsurance underwriting of new prospective risks.

The insurance and reinsurance industry continues to undergo a process of consolidation as industry participants seek to enhance their product and geographic
reach, client base, operating efficiency and general market power through merger and acquisition activities. It is possible that the larger combined entities resulting
from these mergers and acquisition activities may seek to use the benefits of consolidation, including improved efficiencies and economies of scale, to, among
other things, implement price reductions for their products and services to increase their market shares. Consolidation among primary insurance companies may
also lead to reduced use of reinsurance as the resulting larger companies may be able to retain more risk and may also have bargaining power in negotiations with
reinsurers.

We are not presently engaged in active reinsurance underwriting of new prospective risks. If and when we do decide to resume active reinsurance underwriting

of new prospective risks, these competitive pressures could compel us to write business at unprofitable operating margins.

As the insurance and reinsurance industry consolidates, competition may become more intense and the importance of acquiring and properly servicing each
customer will become greater. If and when we do decide to resume active reinsurance underwriting on prospective risks, we could incur greater expenses relating
to customer acquisition and retention, which could reduce our operating margins. When the property-casualty insurance industry has exhibited a greater degree of
competition, premium rates have come under downward pressure as a result.

Taxation

We may become subject to taxes in Bermuda after 2035, which may have a material adverse effect on our financial condition and operating results and on an
investment in our shares.

The  Bermuda  Minister  of  Finance,  under  the  Exempted  Undertakings  Tax  Protection  Act  1966,  as  amended,  of  Bermuda,  has  given  Maiden  Holdings  an
assurance  that  if  any  legislation  is  enacted  in  Bermuda  that  would  impose  tax  computed  on  profits  or  income,  or  computed  on  any  capital  asset,  gain  or
appreciation, or any tax in the nature of estate duty or inheritance tax, then the imposition of any such tax will not be applicable to Maiden Holdings, or any of its
respective operations or its respective shares, debentures or other obligations (except insofar as such tax applies to persons ordinarily resident in Bermuda or to
any taxes payable by them in respect of real property or leasehold interests in Bermuda held by it) until March 31, 2035. Given the limited duration of the Minister
of  Finance’s  expected  assurance,  we  cannot  be  certain  that  we  will  not  be  subject  to  any  Bermuda  tax  after  March  31,  2035.  Since  Maiden  Holdings  is
incorporated in Bermuda, we will be subject to changes in law or regulation in Bermuda that may have an adverse impact on our operations, including imposition
of tax liability.

OECD two-pillar solution to address the tax challenges arising from the digital economy may apply to our activities.

On May 31, 2019, the OECD published a “Programme of Work” designed to address the tax challenges created by an increasing digitalized economy which
was divided into two pillars. Pillar One addresses the broader challenge of a digitalized economy and focuses on the allocation of group profits among taxing
jurisdictions based on a market based concept rather than historical “permanent establishment” concepts, but includes explicit exclusions for Regulated Financial
Services, so is not expected to have a material impact on insurance and reinsurance groups. Pillar Two addresses the remaining BEPS risk of profit shifting to
entities in low tax jurisdictions by introducing a global minimum tax and a proposed tax on base eroding payments, which would operate through a denial of a
deduction or imposition of source-based taxation (including withholding tax) on certain payments.

In  2021,  significant  steps  were  taken  to  develop  a  plan  for  implementing  the  two-pillar  solution.  In  October  2021,  the  OECD/G20  Inclusive  Framework
released a statement agreeing a two-pillar solution to address the tax challenges arising from the digital economy. In December 2021, the OECD issued Pillar Two
model rules for domestic implementation of the global minimum tax and shortly thereafter the European Commission proposed a Directive to implement the Pillar
Two rules into EU law, which will require EU member states to transpose the rules into their national laws by December 31, 2023 with certain measures initially
coming into effect from January 1, 2024. The proposals, in particular in relation to Pillar Two, are broad in scope and we are unable to determine at this time
whether they would have a material adverse impact on our operations and results.

We may be subject to U.S. federal income tax, which would have an adverse effect on our financial condition and results of operations and on an investment
in our shares.

If Maiden Holdings or one of its non-U.S. subsidiaries were considered to be engaged in a trade or business in the U.S., it could be subject to U.S. federal
income and additional branch profits taxes on the portion of its earnings that are effectively connected to such U.S. business. Maiden Holdings is a Bermuda-based
holding company. We intend to manage our business so that Maiden Holdings and its non-U.S. subsidiaries operate in such a manner that none of these companies
should  be  treated  as  engaged  in  a  U.S.  trade  or  business  and,  thus,  should  not  be  subject  to  U.S.  federal  taxation  (other  than  the  U.S.  federal  excise  tax  on
insurance and reinsurance premium income attributable to insuring or reinsuring U.S. risks and U.S. federal withholding tax on certain U.S. source investment
income). Maiden Reinsurance is currently subject to U.S. taxation as a domestic corporation from the effective date of its re-domestication to the State of Vermont
on March 16, 2020.

29

However, there is considerable uncertainty as to which activities constitute being engaged in a trade or business within the U.S., so we cannot be certain that

the IRS will not contend successfully that we are engaged in a trade or business in the U.S.

Net operating losses ("NOL") (and certain other tax attributes or tax benefits of the Maiden NA tax group) may be subject to limitation under Section 382 of
the Tax Code.

Maiden  NA  has  significant  tax  NOL  carryforwards  as  of  December  31,  2022.  As  a  result  of  the  Maiden  NA  NOL  and  other  tax  attributes,  the  Company
presently has a net deferred tax asset with a full valuation allowance against it which may be recognized in future periods. It is possible that certain ownership
changes  of  Maiden  NA,  if  they  were  to  occur,  could  result  in  an  “ownership  change”  of  Maiden  NA  for  purposes  of  Section  382  of  the  Tax  Code.  If  such  an
ownership change (as defined) were to occur, the value and amount of the Maiden NA NOL would be substantially impaired, increasing the U.S. federal income
tax liability of Maiden NA and materially reducing the value of Maiden NA. Should the NOL be limited in any way, it could also limit or eliminate the Company's
ability to recognize and realize that asset in the future.

U.S.  Persons  who  hold  our  shares  may  be  subject  to  U.S.  federal  income  taxation  at  ordinary  income  rates  on  their  proportionate  share  of  Maiden
Reinsurance’s RPII.

If U.S. persons are treated as owning 25% or more of Maiden Holdings’ shares (by vote or by value) (as is expected to be the case) and the RPII of a non-U.S.
insurance subsidiary of Maiden Holdings (determined on a gross basis) were to equal or exceed 20% of its gross insurance income in any taxable year and direct
or indirect insureds (and persons related to those insureds) own directly or indirectly through entities 20% or more of the voting power or value of our shares, then
a U.S. Person who owns any shares of a non-U.S. insurance subsidiary of Maiden Holdings (directly or indirectly through non-U.S. entities) on the last day of the
taxable year would be required to include in its income for U.S. federal income tax purposes such person’s pro rata share of such non-U.S. insurance subsidiary’s
RPII for the entire taxable year, determined as if such RPII were distributed proportionately only to U.S. Persons at that date, regardless of whether such income is
distributed. In addition, any RPII that is includible in the income of a U.S. tax-exempt organization generally will be treated as unrelated business taxable income.
The amount of RPII earned by a non-U.S. insurance subsidiary of Maiden Holdings (generally, premium and related investment income from the direct or indirect
insurance or reinsurance of any direct or indirect U.S. holder of shares or any person related to such holder) will depend on a number of factors, including the
identity of persons directly or indirectly insured or reinsured by a non-U.S. insurance subsidiary.

We believe that either (i) the direct or indirect insureds of Maiden Holdings (and related persons) should not directly or indirectly own 20% or more of either
the voting power or value of our shares or (ii) the RPII (determined on a gross basis) of a non-U.S. insurance subsidiary of Maiden Holdings should not equal or
exceed  20%  of  its  gross  insurance  income  for  the  taxable  year.  However,  we  cannot  be  certain  that  this  will  be  the  case  because  some  of  the  factors  which
determine the extent of RPII may be beyond our control.

U.S. Persons who dispose of our shares may be subject to U.S. federal income taxation at the rates applicable to dividends on a portion of their gains if any.

The RPII rules provide that if a U.S. Person disposes of shares in a non-U.S. insurance corporation in which U.S. Persons own 25% or more of the shares
(even if the amount of gross RPII is less than 20% of the corporation’s gross insurance income or the ownership of its shares by direct or indirect insureds and
related  persons  is  less  than  the  20%  threshold),  any  gain  from  the  disposition  will  generally  be  treated  as  a  dividend  to  the  extent  of  the  holder’s  share  of  the
corporation’s undistributed earnings and profits that were accumulated during the period that the holder owned the shares (whether or not such earnings and profits
are attributable to RPII). In addition, such a holder will be required to comply with certain reporting requirements, regardless of the number of shares owned by
the holder. These RPII rules should not apply to dispositions of our shares because Maiden Holdings will not be directly engaged in the insurance business. The
RPII provisions, however, have never been interpreted by the courts or the U.S. Treasury Department in final regulations, and regulations interpreting the RPII
provisions  of  the  Code  exist  only  in  proposed  form.  It  is  not  certain  whether  these  regulations  will  be  adopted  in  their  proposed  form  or  what  changes  or
clarifications might ultimately be made thereto or whether any such changes, as well as any interpretation or application of the RPII rules by the IRS, the courts, or
otherwise,  might  have  retroactive  effect.  The  U.S.  Treasury  Department  has  authority  to  impose,  among  other  things,  additional  reporting  requirements  with
respect  to  RPII.  Accordingly,  the  meaning  of  the  RPII  provisions  and  the  application  thereof  to  Maiden  Holdings  and  its  non-U.S.  insurance  subsidiary's  is
uncertain.

U.S. Persons who hold our shares will be subject to adverse U.S. federal income tax consequences if Maiden Holdings is considered to be a passive foreign
investment company.

If Maiden Holdings is considered a PFIC for U.S. federal income tax purposes, a U.S. Person who owns directly or, in some cases, indirectly (e.g. through a
non-U.S. partnership) any of our shares will be subject to adverse U.S. federal income tax consequences, including subjecting the investor to a greater tax liability
than  might  otherwise  apply  and  subjecting  the  investor  to  a  tax  on  amounts  in  advance  of  when  such  tax  would  otherwise  be  imposed,  in  which  case  your
investment could be materially adversely affected. In addition, if Maiden Holdings were considered a PFIC, upon the death of any U.S. individual owning our
shares,  such  individual’s  heirs  or  estate  would  not  be  entitled  to  a  "step-up"  in  the  basis  of  the  shares  which  might  otherwise  be  available  under  U.S.  federal
income tax laws. We believe that we are not, and we currently do not expect to become, a PFIC for U.S. federal income tax purposes; however, there can be no
assurance  that  we  will  not  be  deemed  a  PFIC  by  the  IRS.  As  discussed  below,  the  IRS  issued  final  and  proposed  PFIC  regulations.  New  regulations  or
pronouncements interpreting or clarifying these rules may be forthcoming. We cannot predict what impact, if any, such guidance would have on a shareholder that
is subject to U.S. federal income taxation.

U.S. Persons who hold 10% or more of Maiden Holdings’ shares directly or through foreign entities may be subject to taxation under the U.S. CFC rules.

Each 10% U.S. shareholder of a foreign corporation that is a CFC at any time during a taxable year that owns shares in the foreign corporation directly or

indirectly through foreign entities on the last day of the foreign corporation's taxable year during

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which it is a CFC must include in its gross income for U.S. federal income tax purposes its pro rata share of the CFC's "subpart F income," even if the subpart F
income is not distributed. In addition, upon a sale of shares of a CFC, certain 10% U.S. shareholders may be subject to U.S. federal income tax on a portion of
their gain at ordinary income rates.

The Company believes that because of the dispersion of the share ownership in Maiden Holdings, no U.S. Person who owns Maiden Holdings’ shares directly
or  indirectly  through  foreign  entities  should  be  treated  as  a  10%  U.S.  shareholder  of  Maiden  Holdings  or  of  any  of  its  foreign  subsidiaries.  However,  Maiden
Holdings’ shares may not be as widely dispersed as we believe due to, for example, the application of certain ownership attribution rules, and no assurance may be
given that a U.S. Person who owns our shares will not be characterized as a 10% U.S. shareholder, in which case such U.S. Person may be subject to taxation
under U.S. CFC rules.

The 2017 U.S. tax reform legislation, as well as possible future tax legislation and regulations, could materially adversely affect an investment in our shares.

The  2017  Act  amends  a  range  of  U.S.  federal  tax  rules  applicable  to  individuals,  businesses  and  international  taxation,  with  certain  provisions  intended  to
eliminate  certain  perceived  tax  advantages  of  companies  (including  insurance  companies)  that  have  legal  domiciles  outside  the  U.S.  but  have  certain  U.S.
connections and U.S. persons investing in such companies. For example, the 2017 Act includes a BEAT that could make affiliate reinsurance between U.S. and
non-U.S.  members  of  our  group  economically  unfeasible.  In  addition,  the  21%  corporate  income  tax  rate  could  lead  to  higher  after-tax  income  for  most  U.S.
insurance companies in the long term that could result in increased competition for our products and services.

The 2017 Act may also increase the likelihood that we or our non-U.S. subsidiaries will be deemed to be CFCs for U.S. federal tax purposes. Specifically, the
2017  Act  expands  the  definition  of  "10%  U.S.  shareholder"  for  CFC  purposes  to  include  U.S.  persons  who  own  10%  or  more  of  the  value  of  a  foreign
corporation’s shares, rather than only looking to voting power held. As a result, the "voting cut-back" provisions included in our Amended and Restated Bye-laws
that limit the voting power of any shareholder to 9.5% of the total voting power of our capital stock will be ineffective in avoiding "10% U.S. shareholder" status
for U.S. persons who own 10% or more of the value of our shares. The 2017 Act also expands certain attribution rules for stock ownership in a way that would
cause foreign subsidiaries in a foreign parented group that includes at least one U.S. subsidiary to be treated as CFCs. In the event a corporation is characterized as
a CFC, any "10% U.S. shareholder" of the CFC is required to include its pro rata share of certain insurance and related investment income in income for a taxable
year, even if such income is not distributed. In addition, U.S. tax exempt entities subject to the unrelated business taxable income ("UBTI") rules that own 10% or
more of the value of our non-U.S. subsidiaries that are characterized as CFCs may recognize UBTI with respect to such investment.

In addition to changes in the CFC rules, the 2017 Act contains modifications to certain provisions relating to PFIC status that could, for example, discourage
U.S. persons from investing in our company. The 2017 Act makes it more difficult for a non-U.S. insurance company to avoid PFIC status under an exception for
certain non-U.S. insurance companies engaged in the active conduct of an insurance business. The 2017 Act limits this exception to a non-U.S. insurance company
that would be taxable as an insurance company if it were a U.S. corporation and that maintains insurance liabilities of more than 25% of such company’s assets for
a taxable year (or maintains reserves that at least equal 10% of its assets, is predominantly engaged in an insurance business and satisfies a facts and circumstances
test that requires a showing that the failure to exceed the 25% threshold is due to runoff-related or rating-related circumstances) (the "Reserve Test"). In addition,
the IRS recently issued final and proposed regulations (the "2020 Regulations") intended to clarify the application of the PFIC provisions to an insurance company
and provide guidance on a range of issues relating to PFICs including the application of the look-through rule, the treatment of income and assets of certain U.S.
insurance subsidiaries for purposes of the look-through rule and the extension of the look-through rule to 25% or more owned partnerships.

The 2020 Regulations define insurance liabilities for purposes of the Reserve Test, tighten the Reserve Test and the statutory cap on insurance liabilities, and
provide guidance on the runoff-related and rating-related circumstances for purposes of qualifying as a qualifying insurance corporation under the alternative test
(including tightening the scope of non-U.S insurers that can qualify for the rating-related circumstances test). The 2020 Regulations also propose that a non-U.S.
insurer  will  qualify  for  the  insurance  company  exception  only  if  a  factual  requirements  test  or  an  active  conduct  percentage  test  is  satisfied.  The  factual
requirements test will be met if the non-U.S. insurer's officers and employees perform its substantial managerial and operational activities (taking into account
activities of officers and employees of certain related entities in certain cases). The active conduct percentage test will be satisfied if (1) the total costs incurred by
the non-U.S. insurer with respect to its officers and employees (including officers and employees of certain related entities) for services related to core functions
(other than investment activities) equal at least 50% of the total costs incurred for all such services and (2) the non-U.S. insurer's officers and employees oversee
any part of the non-U.S. insurer's core functions, including investment management, that are outsourced to an unrelated party. Services provided by officers and
employees  of  certain  related  entities  are  only  taken  into  account  in  the  numerator  of  the  active  conduct  percentage  if  the  non-U.S.  insurer  exercised  regular
oversight  and  supervision  over  such  services  and  compensation  arrangements  meet  certain  requirements.  The  2020  Regulations  also  propose  that  a  non-U.S.
insurer with no or a nominal number of employees that relies exclusively or almost exclusively upon independent contractors (other than certain related entities) to
perform its core functions. While we believe that our non-U.S. insurance subsidiaries have met, and will continue to meet, the Reserve Test and that we should not
be characterized as a PFIC for the foreseeable future, we cannot assure you that this will continue to be the case in future years.

Impact of U.S. Tax Reform

We  are  unable  to  predict  all  the  ultimate  impacts  of  the  2017  Act  and  other  proposed  tax  reform  regulations  and  legislation  on  our  business  and  results  of
operations. It  is  possible  the  IRS  will  construe  the  intent  of  the  2017  Act  as  having  been  reduce  or  eliminate  certain  perceived  tax  advantages  of  companies
(including insurance companies) that have legal domicile outside the U.S., and its interpretation, enforcement actions or regulatory changes could increase the
impact of the 2017 Act beyond prevailing current assessments or our own estimates. Further, it is possible that other legislation could be introduced and enacted in
the future that would have an adverse impact on us. These events and trends towards more punitive taxation of cross

31

border transactions could in the future materially adversely impact the insurance and reinsurance industry and our own results of operations by increasing taxation
of certain activities and transactions in our industry. Accordingly, we cannot reliably estimate what the potential impact of any such changes could be to us or our
non-U.S. subsidiaries or investors or the market generally, however, it is possible these changes could materially adversely impact our results of operations.

We may be subject to U.K. taxes, which would have an adverse effect on our financial condition and results of operations and on an investment in our shares.

A company which is resident in the U.K. for U.K. corporation tax purposes is subject to U.K. corporation tax in respect of its worldwide income and gains.
While  Maiden  Global  is  a  U.K.  company,  neither  Maiden  Holdings  nor  Maiden  Reinsurance  are  incorporated  in  the  U.K.  Nevertheless,  Maiden  Holdings  or
Maiden Reinsurance would be treated as being resident in the U.K. for U.K. corporation tax purposes if its central management and control were exercised in the
U.K. The concept of central management and control is indicative of the highest level of control of a company’s affairs, which is wholly a question of fact. The
directors and officers of both Maiden Holdings and Maiden Reinsurance intend to manage their affairs so that both companies are resident in Bermuda, and not
resident in the U.K., for U.K. tax purposes. However, HM Revenue & Customs could challenge our tax residence status.

A company which is not resident in the U.K. for U.K. corporation tax purposes can nevertheless be subject to U.K. corporation tax at the rate of 19% (rising to
25% from April 2023) if it carries on a trade in the U.K. through a permanent establishment in the U.K., but the charge to U.K. corporation tax is limited to profits
(both income profits and chargeable gains) attributable directly or indirectly to such permanent establishment.

The directors and officers of Maiden Reinsurance intend to operate the business of Maiden Reinsurance in such a manner that it does not carry on a trade in the
U.K. through a permanent establishment in the U.K. Nevertheless, HM Revenue & Customs might contend successfully that Maiden Reinsurance is trading in the
U.K. through a permanent establishment in the U.K. because there is considerable uncertainty as to the activities which constitute carrying on a trade in the U.K.
through a permanent establishment in the U.K.

The U.K. has no income tax treaty with Bermuda. Companies that are neither resident in the U.K. nor entitled to the protection afforded by a double tax treaty
between the U.K. and the jurisdiction in which they are resident are liable to income tax in the U.K., at the basic rate of 20%, on the profits of a trade carried on in
the U.K., where that trade is not carried on through a permanent establishment in the U.K. The directors and officers of Maiden Reinsurance intend to operate the
business in such a manner that Maiden Reinsurance will not fall within the charge to income tax in the U.K. (other than by way of deduction or withholding).

In addition, diverted profits tax ("DPT") applies to foreign companies with sales in the U.K. (such as Maiden Reinsurance) that design their affairs to avoid
creating a taxable presence (in the form of a permanent establishment) in the U.K., or to U.K. companies that enter into transactions with connected companies
which  lack  economic  substance  to  exploit  differentials  in  tax  rates.  DPT  is  charged  at  25%  (rising  to  31%  from  April  2023)  of  the  profits  representing  the
contribution of the U.K. activities to the group’s results.

If either Maiden Holdings or Maiden Reinsurance were treated as being resident in the U.K. for U.K. corporation tax purposes, or if Maiden Reinsurance were
treated  as  carrying  on  a  trade  in  the  U.K.,  whether  through  a  permanent  establishment  or  otherwise,  or  if  DPT  applied,  the  results  of  our  operations  would  be
materially adversely affected.

Any arrangements (including with regard to the provision of services or financing) between Maiden Global and any non-U.K. resident members of the group
are subject to the U.K. transfer pricing regime.  Consequently, if any such arrangement were found not to be on arm’s length terms and, as a result, a U.K. tax
advantage was being obtained, an adjustment would be required to compute U.K. tax profits as if such arrangement were on arm’s length terms.  Any transfer
pricing  adjustment  could  adversely  impact  the  tax  charge  suffered  by  Maiden  Global.  The  U.K.  has  implemented  the  BEPS  recommendation  for  "country-by-
country" reporting. As a result, our approach to transfer pricing may become subject to greater scrutiny from the U.K. tax authorities.

Clients, Brokers and Financial Institutions

Our retroactive underwriting utilizes reinsurance brokers and other producers, including third party administrators and financial institutions, and the failure
to develop or maintain these relationships could materially adversely affect our ability to market our products and services should we begin to pursue active
reinsurance underwriting.

While we do not presently engage in active reinsurance underwriting of prospective risks, we actively underwrite retroactive risks and source certain of those
opportunities  from  brokers  and  other  producers,  thus  our  failure  to  further  develop  or  maintain  relationships  with  brokers  and  other  producers,  including  third
party  administrators  and  financial  institutions,  from  whom  we  expect  to  receive  our  business  could  have  a  material  adverse  effect  on  our  business,  financial
condition and results of operations.

Our reliance on brokers subjects us to their credit risk.

In accordance with industry practice, we anticipate that we will frequently pay amounts owed on claims under our reinsurance contracts to brokers, and these
brokers  in  turn  are  required  to  pay  and  will  pay  these  amounts  over  to  the  clients  that  have  purchased  reinsurance  from  us.  If  a  broker  fails  to  make  such  a
payment, it is highly likely that we will be liable to the client for the deficiency under local laws or contractual obligations, notwithstanding the broker’s obligation
to make such payment. Likewise, when the client pays premiums for these policies to brokers for payment over to us, these premiums are considered to have been
paid  and,  in  most  cases,  the  client  will  no  longer  be  liable  to  us  for  those  amounts,  whether  or  not  we  actually  receive  the  premiums  from  the  brokers.
Consequently, we will assume a degree of credit risk associated with brokers with whom we work with respect to some of our reinsurance business.

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We could incur substantial losses and reduced liquidity if one of the financial institutions we use in our operations fails.

We  have  exposure  to  counterparties  in  many  different  industries  and  routinely  execute  transactions  with  counterparties  in  the  financial  services  industry,
including  brokers  and  dealers,  commercial  banks,  and  other  institutions.  Many  of  these  transactions  expose  us  to  credit  risk  in  the  event  of  default  of  our
counterparty. In addition, with respect to secured transactions, our credit risk may be exacerbated when the collateral held by us cannot be realized or is liquidated
at prices not sufficient to recover the full amount of the obligation.

We  maintain  cash  balances,  including  restricted  cash  held  in  trust  accounts,  significantly  in  excess  of  the  Federal  Deposit  Insurance  Corporation  insurance
limits at various depository institutions. We also maintain cash balances in foreign banks and institutions. If one or more of these financial institutions were to fail,
our ability to access cash balances may be temporarily or permanently limited, which could have a material adverse effect on our results of operations, financial
condition or cash flows.

Item 1B. Unresolved Staff Comments.

None.

Item 2. Properties.

We  currently  lease  office  space  in  Pembroke,  Bermuda  (our  corporate  headquarters),  New  York,  the  U.K.,  Sweden  and  Germany  for  the  operation  of  our
business.  We  renew  and  enter  into  new  leases  in  the  ordinary  course  of  business  as  needed.  We  believe  that  the  office  space  from  these  leased  properties  is
sufficient for us to conduct our operations for the foreseeable future. To date, the cost of acquiring and maintaining our office space has not been material to us as
a whole.

33

Item 3. Legal Proceedings.

We  may  become  involved  in  various  claims  and  legal  proceedings  that  arise  in  the  normal  course  of  our  business,  which  are  not  likely  to  have  a  material

adverse effect on our financial position, results of operations or liquidity.

Except  as  noted  below,  we  are  not  a  party  to  any  material  legal  proceedings.  From  time  to  time,  we  are  subject  to  routine  legal  proceedings,  including
arbitrations,  arising  in  the  ordinary  course  of  business.  These  legal  proceedings  generally  relate  to  claims  asserted  by  or  against  us  in  the  ordinary  course  of
insurance or reinsurance operations. Based on our opinion, the eventual outcome of these legal proceedings is not expected to have a material adverse effect on our
financial condition or results of operations.

In  April  2009,  we  learned  that  Bentzion  S.  Turin,  the  former  Chief  Operating  Officer,  General  Counsel  and  Secretary  of  Maiden  Holdings  and  Maiden
Reinsurance,  sent  a  letter  to  the  U.S.  Department  of  Labor  claiming  that  his  employment  with  the  Company  was  terminated  in  retaliation  for  corporate
whistleblowing in violation of the whistleblower protection provisions of the Sarbanes-Oxley Act of 2002. Mr. Turin alleged that he was terminated for raising
concerns regarding corporate governance with respect to the negotiation of the terms of the Trust Preferred Securities Offering. He seeks reinstatement as Chief
Operating Officer, General Counsel and Secretary of Maiden Holdings and Maiden Reinsurance, back pay and legal fees incurred. On December 31, 2009, the
U.S. Secretary of Labor found no reasonable cause for Mr. Turin’s claim and dismissed the complaint in its entirety. Mr. Turin objected to the Secretary's findings
and  requested  a  hearing  before  an  administrative  law  judge  in  the  U.S.  Department  of  Labor.  The  Company  moved  to  dismiss  Mr.  Turin's  complaint,  and  its
motion was granted by the Administrative Law Judge on June 30, 2011. On July 13, 2011, Mr. Turin filed a petition for review of the Administrative Law Judge's
decision with the Administrative Review Board in the U.S. Department of Labor. On March 29, 2013, the Administrative Review Board reversed the dismissal of
the complaint on procedural grounds, and remanded the case to the administrative law judge. The administrative hearing began in September 2014 and concluded
in  November  2018.  On  September  2,  2021,  Administrative  Law  Judge  Theresa  C.  Timlin  of  the  U.S.  Department  of  Labor  issued  a  decision  and  order  which
denied  Mr.  Turin’s  complaint  in  full.  On  September  16,  2021,  Mr.  Turin  filed  a  petition  for  review  of  the  Administrative  Law  Judge's  decision  with  the
Administrative Review Board in the U.S. Department of Labor. We believe that we had good and sufficient reasons for terminating Mr. Turin's employment and
that the claim is without merit. We will continue to vigorously defend ourself against this claim.

A putative class action complaint was filed against Maiden Holdings, Arturo M. Raschbaum, Karen L. Schmitt, and John M. Marshaleck in the United States
District Court for the District of New Jersey on February 11, 2019. On February 19, 2020, the Court appointed lead plaintiffs, and on May 1, 2020, lead plaintiffs
filed an amended class action complaint (the “Amended Complaint”). The Amended Complaint asserts violations of Section 10(b) of the Exchange Act and Rule
10b-5 (and Section 20(a) for control person liability) arising in large part from allegations that Maiden failed to take adequate loss reserves in connection with
reinsurance  provided  to  AmTrust.  Plaintiffs  further  claim  that  certain  of  Maiden  Holdings’  representations  concerning  its  business,  underwriting  and  financial
statements were rendered false by the allegedly inadequate loss reserves, that these misrepresentations inflated the price of Maiden Holdings' common stock, and
that when the truth about the misrepresentations was revealed, the Company’s stock price fell, causing Plaintiffs to incur losses. On September 11, 2020, a motion
to dismiss was filed on behalf of all Defendants. On August 6, 2021, the Court issued an order denying, in part, Defendants’ motion to dismiss, ordering Plaintiffs
to file a shorter amended complaint no later than August 20, 2021, and permitting discovery to proceed on a limited basis. On February 7, 2023, the District Court
denied  Plaintiffs’  motion  for  reconsideration  of  the  District  Court’s  decision  denying  Plaintiffs’  objection  to  the  Magistrate  Judge’s  December  2021  ruling  on
discovery.  The  Company  expects  to  file  a  dispositive  motion  in  the  near  future.  We  believe  the  claims  are  without  merit  and  we  intend  to  vigorously  defend
ourselves. It is possible that additional lawsuits will be filed against the Company, its subsidiaries and its respective officers due to the diminution in value of our
securities as a result of our operating results and financial condition. It is currently uncertain as to the effect of such litigation on our business, operating results
and financial condition.

Item 4. Mine Safety Disclosures.

Not applicable.

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Item 5. Market for Registrant’s Common Equity, Related Stockholder Matters and Issuer Purchases of Equity Securities.

PART II

Our common shares began publicly trading on NASDAQ Stock Market LLC ("NASDAQ") under the symbol "MHLD" on May 6, 2008 and currently trades on
the NASDAQ Capital Market. At March 10, 2023, the closing sale price of our common share was $2.57 per share and there were 20 holders of record of our
common shares. This figure does not represent the actual number of beneficial owners of our common shares because shares are frequently held in "street name"
by securities dealers and others for the benefit of beneficial owners who may vote the shares.

No dividends have been declared by our Board on our common shares since the third quarter of 2018. The future declaration and payment of dividends to
common  shareholders  will  be  at  the  discretion  of  our  Board  subject  to  specified  legal,  regulatory,  financial  and  other  restrictions.  Please  see  "Notes  to
Consolidated Financial Statements - Note 15 — Statutory Requirements and Dividend Restrictions" under Item 8 "Financial Statements and Supplementary Data"
of this Annual Report on Form 10-K for discussion regarding dividend restrictions on subsidiary's ability to transfer funds to Maiden Holdings.

On February 21, 2017, our Board approved the repurchase of up to $100.0 million of our common shares from time to time at market prices. During the years
ended December 31, 2022 and 2021, the Company did not repurchase any common shares under its share repurchase authorization. At December 31, 2022, we
have  a  remaining  authorization  of  $74.2  million  for  share  repurchases.  No  repurchases  of  common  shares  were  made  subsequent  to  December  31,  2022  and
through the period ended March 15, 2023 under its share repurchase authorization.

During the year ended December 31, 2022, we repurchased a total of 403,716 (2021 - 834,851) common shares at an average price of $2.50 per share (2021 -
$2.97)  from  employees,  which  represent  tax  withholding  in  respect  of  tax  obligations  on  the  vesting  of  both  non-performance-based  and  discretionary
performance-based restricted shares.

Exchange of Preference Shares

On December 27, 2022, the Company completed the Exchange with record holders of the Series A, C and D Preference Shares. The Company offered three
common shares as consideration for each share of the Series A, C and D Preference Shares tendered. A total of 1,500,050 shares of Series A Preference Shares,
1,744,028  shares  of  Series  C  Preference  Shares,  and  1,542,806  shares  of  Series  D  Preference  Shares  were  accepted,  resulting  in  the  issuance  of  14,360,652
common shares to non-affiliates at a fair value of $28.4 million. The Exchange was accounted for as an extinguishment resulting in derecognition of the $119.7
million carrying amount of Series A, C and D Preference Shares tendered, elimination of $4.0 million of original issuance costs, recognition of the $25.9 million
excess of the fair value of the common shares issued over par value, net of $2.4 million issuance costs, as additional paid in capital, and recognition of the $87.2
million excess of the carrying amount of the Preference Shares redeemed over the fair value of the common shares issued as an increase to retained earnings.

The number of the Company's Series A, C and D Preference Shares held by Maiden Reinsurance pursuant to the 2020 Tender Offer and the 2021 Preference
Share Repurchase Program was 13,813,116 at the Exchange Date. Therefore, 41,439,348 common shares were issued to Maiden Reinsurance in exchange for the
Preference Shares held which are reflected as treasury shares on the Consolidated Balance Sheet and are not treated as outstanding shares on December 31, 2022.

As a result of the Exchange, the Preference Shares were delisted from and no longer trade on the New York Stock Exchange as of the Exchange Date. No
Preference Shares are issued or outstanding, and the Preference Shares were deregistered under the Securities Exchange Act of 1934, as amended. In addition, all
rights of the former holders related to ownership of the Preference Shares have terminated.

Preference Shares Repurchases

On March 3, 2021, our Board approved the repurchase, including the repurchase by Maiden Reinsurance in accordance with its investment guidelines, of up to
$100.0 million of our Preference Shares from time to time at market prices in open market purchases or as may be privately negotiated. On May 6, 2021, our
Board approved the additional repurchase, including the repurchase by Maiden Reinsurance in accordance with its investment guidelines (as may be amended), of
up to $50.0 million of our Preference Shares from time to time at market prices in open market purchases or as may be privately negotiated. The authorizations
that were approved on March 3, 2021 and May 6, 2021 as described above are collectively referred to as the "2021 Preference Share Repurchase Program". For
further information and a summary of the Company's preference shares repurchases made during the years ended December 31, 2022 and 2021, please see "Notes
to  Consolidated  Financial  Statements  -  Note  6.  Shareholders'  Equity"  included  under  Item  8  "Financial  Statements  and  Supplementary  Data"  of  this  Annual
Report on Form 10-K.

Please also see "Notes to Consolidated Financial Statements - Note 14. Share Compensation and Pension Plans" included under Item 8 "Financial Statements

and Supplementary Data" of this Annual Report on Form 10-K for a discussion about the Company's equity compensation plans.

35

Item 7. Management’s Discussion and Analysis of Financial Condition and Results of Operations.

The  following  discussion  and  analysis  of  our  financial  condition  and  results  of  operations  should  be  read  in  conjunction  with  our  Consolidated  Financial
Statements and related notes included elsewhere in this Annual Report on Form 10-K and Item 1, "Business - General Overview". Except as explicitly described
as discontinued operations, and unless otherwise noted, all discussions and amounts presented herein relate to the Company's continuing operations except for net
income  (loss)  and  net  income  available  to  Maiden  common  shareholders.  Amounts  in  tables  may  not  reconcile  due  to  rounding  differences.  Some  of  the
information contained in this discussion and analysis or set forth elsewhere in this Report, including information with respect to our plans and strategy for our
business, includes forward-looking statements that involve risk and uncertainties. Please see the "Special Note About Forward-Looking Statements" in this Annual
Report on Form 10-K for more information on factors that could cause actual results to differ materially from the results described in or implied by any forward-
looking statements contained in this discussion and analysis. You should review the "Risk Factors" set forth in this Annual Report on Form 10-K for a discussion
of important factors that could cause actual results to differ materially from the results described in or implied by the forward-looking statements contained herein.

Overview

Maiden  Holdings  is  a  Bermuda-based  holding  company.  We  create  shareholder  value  by  actively  managing  and  allocating  our  assets  and  capital,  including
through ownership and management of businesses and assets mostly in the insurance and related financial services industries where we can leverage our deep
knowledge of those markets. Through GLS, we also provide a full range of legacy services to small insurance companies, particularly those in run-off or with
blocks of reserves that are no longer core to those companies' operations, working with clients to develop and implement finality solutions including acquiring
entire companies that enable our clients to meet their capital and risk management objectives. We expect our legacy solutions business to contribute to our active
asset and capital management strategies.

We are not currently underwriting reinsurance business on new prospective risks but are actively underwriting risks on a retroactive basis through GLS. We
also have various historic reinsurance programs underwritten by Maiden Reinsurance which are in run-off, including the liabilities associated with AmTrust which
we  terminated  in  2019  as  discussed  in  "Note 10 — Related Party Transactions" of  the  Notes  to  Consolidated  Financial  Statements  included  in  Part  II  Item  8.
"Financial Statements and Supplementary Data". In addition, we have a LPT/ADC Agreement with Cavello and a commutation agreement that further reduces
our exposure to and limits the potential volatility related to our AmTrust liabilities in run-off, as discussed in "Note 8 — Reinsurance" of the Notes to Consolidated
Financial Statements included in Part II Item 8. "Financial Statements and Supplementary Data".

Short-term income protection business is written on a primary basis by our wholly owned subsidiaries Maiden LF and Maiden GF in the Scandinavian and
Northern European markets. Insurance support services are provided to Maiden LF and Maiden GF through our wholly owned subsidiary, Maiden Global, which
is also a licensed intermediary in the U.K.. Maiden Global had previously operated internationally by providing branded auto and credit life insurance products
through insurer partners, particularly those in Europe and other global markets. These products also produced reinsurance programs which were underwritten by
our wholly owned subsidiary Maiden Reinsurance.

Our business currently consists of two reportable segments: Diversified Reinsurance and AmTrust Reinsurance. Our Diversified Reinsurance segment consists
of a portfolio of predominantly property and casualty reinsurance business focusing on regional and specialty property and casualty insurance companies located
primarily  in  Europe.  This  segment  also  includes  transactions  entered  into  by  GLS  which  was  formed  in  November  2020. Our  AmTrust  Reinsurance  segment
includes all business ceded to Maiden Reinsurance by AmTrust, primarily the AmTrust Quota Share and the European Hospital Liability Quota Share, both of
which are in run-off effective as of January 1, 2019. Please refer to Item 1. "Business - Our Reportable Segments" section for further discussion on our reportable
segments.

Business Strategy

We continued to implement our revised operating strategy during 2022, which leverages the significant assets and capital we retain. In addition to restoring
operating  profitability,  our  strategic  focus  centers  on  creating  the  greatest  risk-adjusted  shareholder  returns  in  order  to  increase  book  value  for  our  common
shareholders, both near and long-term. This strategy has three principal areas of focus:

•Asset management - investing in assets and asset classes in a prudent but expansive manner in order to maximize investment returns and is principally
enabled by limiting the amount of insurance risk we assume in relation to the assets we hold and maintaining required regulatory capital at very strong
levels to manage our aggregate risk profile;

•Legacy  underwriting  -  judiciously  building  a  portfolio  of  legacy  run-off  acquisitions  and  retroactive  reinsurance  transactions  which  we  believe  will
produce attractive underwriting returns; and

•Capital management - effectively managing the capital we hold on our balance sheet and when appropriate, repurchasing securities or returning capital to
enhance common shareholder returns.

The  returns  expected  to  be  produced  by  each  pillar  of  our  strategy  are  evaluated  in  relation  to  our  cost  of  debt  capital,  which  carries  a  weighted  average
effective interest rate of 7.6%. To the extent our experience or belief indicates we cannot exceed the cost of debt capital, we expect to refrain from activities in
those areas.

As an example, our present assessment of the reinsurance marketplace along with our current operating profile continues to be that the risk-adjusted returns

that may be produced via active reinsurance underwriting of new prospective risks are likely to

36

be  lower  over  the  long-term  than  our  cost  of  capital.  However,  as  interest  rates  have  increased  and  moved  towards  historically  observed  levels,  risk-adjusted
returns  for  active  reinsurance  underwriting  of  new  prospective  risks  may  become  more  attractive  and  while  we  have  no  immediate  plans  to  resume  such
underwriting, we continue to evaluate if such a strategy would produce suitable value for shareholders.

The measures implemented in recent years have allowed us to more flexibly allocate capital to those activities most likely to produce the greatest returns for
shareholders, and we are actively engaged in evaluating and deploying funds in all pillars of the strategies as discussed herein. We also believe that these areas of
strategic  focus  will  enhance  our  profitability  through  increased  returns,  which  we  believe  also  increase  the  likelihood  of  fully  utilizing  the  significant  NOL
carryforwards described above which would create additional common shareholder value.

As  part  of  our  expanded  asset  management  activities,  we  have  evaluated  and  continue  to  consider  investing  in  various  initiatives  in  the  insurance  industry
across a variety of segments which we believe will produce appropriate risk-adjusted returns while maintaining the option to consider underwriting activities in the
future. We believe these expanded activities will produce a broad range of positive impacts on our financial condition, including current income, longer-term gains
and in certain instances, fee income.

In  recent  years,  we  have  invested  approximately  $272.5  million  into  alternative  investments  which  include  equity  securities,  other  investments  and  equity
method investments in a wide variety of asset classes and we believe these activities will exceed that benchmark cost of capital with adjustments as necessary if
those returns do not emerge.

In November 2020, we formed GLS which specializes in providing a full range of legacy services to small insurance entities, particularly those in run-off or
with  blocks  of  reserves  that  are  no  longer  core  to  those  companies'  operations,  working  with  clients  to  develop  and  implement  finality  solutions  including
acquiring entire companies that enable our clients to meet their capital and risk management objectives. We acquire legacy liabilities and (re)insurance reserves
from  companies  and  provide  retroactive  reinsurance  coverage  for  portfolios  of  (re)insurance  business,  primarily  via  loss  portfolio  transfer  contracts  (“LPT”).
Additionally, we provide reinsurance contracts to other (re)insurers to mitigate some of their risk of future adverse development (an adverse development cover, or
“ADC”) on insurance risks relating to prior accident years.

We believe the formation of GLS is highly complementary to our overall longer-term strategy and will produce risk-adjusted returns in excess of our debt cost
of  capital.  In  addition,  while  we  anticipate  profitable  growth  from  the  GLS  portfolio  as  it  develops,  we  expect  our  required  capital  to  continue  to  decline  as
insurance risk incurred by GLS will be more than offset by the run-off of insurance liabilities from our prior reinsurance strategies. GLS, along with other recent
insurance industry investments, enables us to leverage our knowledge base while not re-entering active underwriting of new prospective risks and maintaining an
efficient operating profile. We believe GLS not only enhances our profitability through both fee income and effective claims management services, but it will also
increase our asset base through the addition of blocks of reserves or companies that can be successfully wound down.

Effective October 1, 2021, GLS completed its first loss portfolio transfer transaction which includes an ADC cover. GLS and its subsidiaries have completed
additional transactions in 2022 and as of December 31, 2022, GLS and its subsidiaries have insurance related liabilities totaling $45.1 million which included total
reserves of $28.2 million, derivative liability on retroactive reinsurance of $14.6 million, and deferred gains on retroactive reinsurance of $2.3 million.

GLS continues to write additional retroactive reinsurance transactions consistent with its business plan and in 2022 acquired its first insurance company to run-
off. In addition to producing long-term returns that exceed the target cost of capital, we expect the business produced through GLS should further enhance our
ability to pursue the asset and capital management pillars of our business strategy. The nature of GLS business plan is that it may take a sustained period of growth
in insurance liabilities to produce the targeted returns. In addition, early stage initiatives such as GLS may take a period of time to reach profitability. Finally, the
nature of legacy transactions which GLS seeks to execute may be inconsistent as to their timing and not predictable as regards how many transactions may be
completed in any fiscal period.

Our capital management strategy is significantly informed by the required capital needed to operate our business in a prudent manner and our ongoing analysis
of  our  loss  development  trends.  Trends  in  recent  years  have  increased  our  confidence  in  our  recorded  ultimate  losses  for  our  insurance  liabilities  in  run-off,
however a prudent assessment dictates that the run-off portfolio still requires additional maturity to fully emerge, as evidenced by the adverse loss development we
experienced in 2022. While there is no assurance that these recent positive long-term loss development trends will persist, as our confidence has increased, it has
enabled us to pursue continued capital management initiatives, primarily the repurchase of our preference shares and the subsequent Exchange, which we believe
provided the greatest risk-adjusted returns to our common shareholders.

Completion of the Exchange represents a significant milestone in our capital management plan and we continue to evaluate other capital management options
that may be available to us. However, there can be no assurance that we will pursue such initiatives, or that they will provide appropriate risk-adjusted returns. Our
ability to execute our asset and capital management initiatives is dependent on maintaining adequate levels of unrestricted liquidity and cash flows. Further, there
can be no assurance that our insurance liabilities will run-off at levels that will permit further capital management activities, which we continually review as part
of our strategy.

Please refer to the "Liquidity and Capital Resources" section for further information on our asset and capital management activities.

37

2022 Developments

During 2022, we continued to advance each pillar of our business strategy and our book value increased by 7.7% to $2.80 per common share at December 31,
2022. We made significant progress in the capital management pillar of our business strategy, repurchasing additional preference shares and ultimately executing
an exchange of all of our outstanding preference shares for our common shares as discussed in the "Exchange of Preference Shares" section below. These capital
management measures produced gains of $115.5 million and were the single biggest driver of our increase in book value.

We also grew our alternative investment portfolio by 21% and produced a positive return of 2.0% on that portfolio in a very challenging year in the global
financial markets. Despite the volatility experienced in financial markets during 2022, we believe our alternative investment portfolio remains well positioned to
achieve its targeted longer-term returns. As interest rates continue to rise, we are increasingly focusing our investing activities on opportunities that will produce
current  income.  While  we  continued  to  develop  the  business  platform  of  GLS  during  2022,  a  disappointing  operating  loss  was  reported  as  new  reinsurance
contracts did not perform to expectations.

The run-off of our historic reinsurance programs significantly underperformed during 2022, and we experienced adverse prior year reserve development of
$32.6 million which offset much of the positive progress made in our capital and asset management strategies. Finally, volatile financial markets and sharply rising
interest rates resulted in downward pressure on both our book value and earnings as investment results, including both realized and unrealized, were adversely
affected.

Exchange of Preference Shares

On  the  Exchange  Date,  the  Company  exchanged  all  of  its  outstanding  Preference  Shares  for  its  common  shares,  $0.01  par  value  per  share.  The  Company
offered three common shares as consideration for each share of the Series A, C and D Preferred Stock tendered. A total of 1,500,050 shares of Series A Preference
Shares, 1,744,028 shares of Series C Preference Shares, and 1,542,806 shares of Series D Preference Shares were accepted, resulting in the issuance of 14,360,652
common shares to non-affiliates at a fair value of $28.4 million. The Exchange was accounted for as an extinguishment resulting in the derecognition of the $119.7
million carrying amount of Series A, C and D Preference Shares tendered, elimination of $4.0 million of original issuance costs, recognition of the $25.9 million
excess of the fair value of the common shares issued over par value, net of $2.4 million issuance costs, as additional paid in capital, and recognition of the $87.2
million excess of the carrying amount of the Preference Shares redeemed over the fair value of the common shares issued as an increase to retained earnings.

Prior to the Exchange, Maiden Reinsurance owned approximately 74% of the outstanding Preference Shares. After the Exchange, Maiden Reinsurance owns

29% of our total outstanding common shares and subject to limitations in our bye-laws, has a 9.5% voting interest in our common shares.

Please refer to "Notes to Consolidated Financial Statements - Note 6 — Shareholders' Equity" under Item 8 "Financial Statements and Supplementary Data" of

this Annual Report on Form 10-K for further information on the Exchange.

We believe Maiden NA’s investments, including its ownership of Maiden Reinsurance and its active asset management strategy, will create opportunities to
utilize NOL carryforwards of $280.7 million at December 31, 2022. The NOL carryforwards combined with additional net deferred tax assets ("DTA") primarily
related to our insurance liabilities result in U.S. DTA (before valuation allowance) of $116.2 million or $1.14 per common share at December 31, 2022.

Net U.S. DTA of $116.2 million is not presently recognized on the Company's consolidated balance sheet as a full valuation allowance is carried against it. At
this time, while positive evidence in support of reducing the valuation allowance is growing, the Company believes it is necessary to maintain a full valuation
allowance against the net U.S. DTA as more evidence is needed regarding the utilization of these losses, primarily the adverse loss development experienced in
2022. As circumstances further develop, we will continuously evaluate the amount of the valuation allowance held against the net U.S. DTA.

For further details please see "Note 13 — Income Taxes"  included  under  Item  8  "Financial  Statements  and  Supplementary  Data"  of  this  Annual  Report  on
Form  10–K.  Taken  together,  we  believe  these  measures  should  generate  additional  income  for  Maiden  NA  in  a  tax-efficient  manner,  while  sharing  in  the
improvement in profitability anticipated in Maiden Reinsurance as a result of the measures enacted as described above.

38

2022 and 2021 Financial Highlights

For the Year Ended December 31,
Summary Consolidated Statement of Income Data:
Net (loss) income
Gain from repurchase & exchange of preference shares
Net income attributable to Maiden common shareholders
Basic and diluted earnings per common share:
Net income attributable to Maiden common shareholders
Gain from repurchase/exchange of preference shares per common share
Gross premiums written
Net premiums earned
Underwriting (loss) income
Net investment results
Non-GAAP measures:
Non-GAAP operating earnings
Non-GAAP diluted operating earnings per common share
Non-GAAP operating return on average common shareholders' equity

(13)

(2)

(1)

(1)

(3)

(1)

(4)

At December 31,
Consolidated Financial Condition
Total investments and cash and cash equivalents
Total assets
Reserve for loss and LAE
Senior notes - principal amount
Common shareholders' equity
Shareholders' equity
Total capital resources
Ratio of debt to total capital resources
Book Value calculations:
Book value per common share
Accumulated dividends per common share

(12)

(10)

(6)

(5)

Book value per common share plus accumulated dividends
Change in book value per common share plus accumulated dividends
Diluted book value per common share
Non-GAAP measures:
Adjusted book value per common share
(9)
Adjusted Maiden shareholders' equity
Adjusted total capital resources
Ratio of debt to adjusted total capital resources

(11)

(9)

(8)

(7)

$

$

$

$

$

2022

2021

Change

($ in thousands except per share data)
$

$

26,645 
90,998 
117,643 

(60,041)
115,473 
55,432 

0.63 
1.33 
5,479 
37,732 
(54,934)
24,725 

52,070 
0.60 
17.2 %

1.35 
1.06 
10,938 
52,993 
11,572 
52,409 

60,481 
0.70 
25.0 %

(86,686)
24,475 
(62,211)

(0.72)
0.27 
(5,459)
(15,261)
(66,506)
(27,684)

(8,411)
(0.10)
(7.8)

2022

2021

Change

($ in thousands except per share data)
$

$

633,684 
1,846,866 
1,131,408 
262,500 
284,579 
284,579 
547,079 

888,699 
2,322,610 
1,489,373 
262,500 
225,047 
384,257 
646,757 

48.0 %

2.80 
4.27 
7.07 

2.9 %

2.79 

$

$

$

40.6 %

2.60 
4.27 
6.87 

2.59 

$

$

$

3.25 
329,987 
592,487 

44.3 %

3.18 
434,200 
696,700 

37.7 %

(255,015)
(475,744)
(357,965)
— 
59,532 
(99,678)
(99,678)
7.4 

0.20 
— 
0.20 

0.20 

0.07 
(104,213)
(104,213)
6.6 

(1) Non-GAAP  operating  earnings,  non-GAAP  diluted  operating  earnings  per  common  share  and  non-GAAP  operating  return  on  average  common  shareholders'  equity  are  non-GAAP  financial

measures. See "Key Financial Measures" for additional information.

(2) Please refer to "Notes to Consolidated Financial Statements - Note 12. Earnings per Common Share" included under Item 8 "Financial Statements and Supplementary Data" of this Annual Report

on Form 10-K for the calculation of basic and diluted earnings per common share.

(3) Underwriting  (loss)  income  is  a  non-GAAP  measure  and  is  calculated  as  net  premiums  earned  plus  other  insurance  (expense)  revenue,  less  net  loss  and  LAE,  commission  and  other  acquisition

expenses and general and administrative expenses directly related to underwriting activities. See "Key Financial Measures" for additional information.

39

(4) Total investments and cash and cash equivalents includes both restricted and unrestricted.
(5) Total capital resources is the sum of the Company's principal amount of debt and Maiden shareholders' equity. See "Key Financial Measures" for additional information.
(6) Book  value  per  common  share  is  calculated  using  common  shareholders’  equity  (shareholders'  equity  excluding  the  aggregate  liquidation  value  of  our  Preference  Shares,  if  any)  divided  by  the

number of common shares outstanding. See "Key Financial Measures" for additional information.

(7) Diluted  book  value  per  common  share  is  calculated  by  dividing  common  shareholders'  equity,  adjusted  for  assumed  proceeds  from  the  exercise  of  dilutive  options,  divided  by  the  number  of

outstanding common shares plus dilutive options and restricted shares (assuming exercise of all dilutive share based awards).

(8) Adjusted  book  value  per  common  share  is  a  non-GAAP  measure  that  is  calculated  using  common  shareholders'  equity,  adjusted  by  adding  the  following  items  to  shareholders'  equity:  1)  the
unamortized deferred gain on retroactive reinsurance arising from the LPT/ADC Agreement; and 2) an adjustment which reflects the equity method accounting related to the fair value of certain
hedged liabilities within an equity method investment in a limited partnership investment held by the Company wherein the ultimate realizable value of the asset supporting the hedged liabilities
cannot currently be recognized at fair value, divided by the number of common shares outstanding. See "Key Financial Measures" for additional information.

(9) Adjusted shareholders' equity and adjusted total capital resources are calculated by adding the following items to shareholders' equity: 1) the unamortized deferred gain on retroactive reinsurance
arising from the LPT/ADC Agreement; and 2) an adjustment which reflects the equity accounting related to the fair value of certain hedged liabilities within an equity method investment held by the
Company wherein the ultimate realizable value of the asset supporting the hedged liabilities cannot currently be recognized at fair value. The deferred gain arises from the LPT/ADC Agreement with
Cavello relating to losses from the AmTrust Quota Share. Under U.S. GAAP, the deferred gain shall be amortized over the estimated remaining settlement period. See "Key Financial Measures" for
additional information.

(10) Ratio of debt to total capital resources is calculated using the total principal amount of debt divided by the sum of total capital resources.
(11) Ratio of debt to adjusted total capital resources is calculated using the total principal amount of debt divided by the sum of adjusted total capital resources.
(12) Accumulated dividends per common share includes the cumulative sum of dividends declared and paid in the past on the Company's issued common shares since inception.
(13) Net investment results include the sum of net investment income, net realized and unrealized gains (losses), and interest in income (loss) of equity method investments.

Key Financial Measures

Revenues

We historically derived the majority of our revenues from premiums on reinsurance contracts, net of any reinsurance or retrocessional coverage purchased and
to a minor extent from premiums from insurance policies. Reinsurance premiums are a function of the amount and types of policies and contracts we write, as well
as  prevailing  market  prices.  Our  prices  are  determined  before  our  ultimate  costs,  which  may  extend  far  into  the  future,  are  known.  As  a  result  of  significant
strategic transactions, our gross and net premiums written continue to be materially lower and our net investment income will increasingly become a significantly
larger portion of our total revenues compared to prior periods.

The  Company's  revenues  also  include  fee  income  earned  from  both  our  GLS  business  and  IIS  business  as  well  as  income  generated  from  our  investment
portfolio. The Company's investment portfolio is comprised of AFS fixed maturity investments and other investments including equities, private equity and credit
funds, privately held investments, hedge funds, equity method investments and other non-fixed income investments. In accordance with U.S. GAAP, our fixed
maturity investments are carried at fair market value and any unrealized gains and losses are included in AOCI as a separate component of shareholders' equity. If
unrealized losses are considered to be other-than-temporarily impaired due to a credit-related event, such impairment losses are recognized within earnings as a
realized loss under total other-than-temporary impairment losses. Equity and other investments include limited partnerships, hedge funds and start-up insurance
entities  which  are  carried  at  fair  market  value  with  any  unrealized  gains  or  losses  included  in  earnings  under  net  realized  gains  (losses)  on  investment.  Our
investments made by special purpose vehicles focused on lending activities are carried at cost. Any indication of impairment is recognized immediately within net
income.

Expenses

Our  expenses  currently  consist  largely  of  net  loss  and  LAE,  commission  and  other  acquisition  expenses,  general  and  administrative  expenses,  interest  and
amortization expenses, foreign exchange and other gains or losses, the latter of which includes on a non-recurring basis any gains or losses from the disposal of
subsidiaries.

Net loss and LAE has three main components: (1) losses paid, which are actual cash payments to insureds, net of recoveries from reinsurers; (2) change in
outstanding loss or case reserves, which represent cedants' best estimate of the likely settlement amount for known claims, less the portion that can be recovered
from reinsurers; and (3) change in IBNR reserves, which we establish to respond to changes in the values of claims that have been reported to us but are not yet
settled, as well as claims that have occurred but have not yet been reported to us. The portion recoverable from reinsurers is deducted from the gross estimated
loss.

Commission and other acquisition expenses include commissions, brokerage fees and insurance taxes. Commissions and brokerage fees are usually calculated
as  a  percentage  of  premiums  and  depend  on  the  market  and  line  of  business  and  can,  in  certain  instances,  vary  based  on  loss  sensitive  features  of  reinsurance
contracts.  Commission  and  other  acquisition  expenses  are  reported  after:  (1)  deducting  commissions  received  on  ceded  reinsurance;  (2)  deducting  the  part  of
commission  and  other  acquisition  expenses  relating  to  unearned  premiums;  and  (3)  including  the  amortization  of  previously  deferred  commission  and  other
acquisition expenses.

General  and  administrative  expenses  include  personnel  expenses  (including  share-based  compensation  expense),  audit  fees,  rent  expenses,  legal  and

professional fees, information technology costs and other general operating expenses. General and

40

administrative expenses are allocated to the reportable segments on an actual basis except salaries and benefits where management’s judgment is applied; however
general corporate expenses are not allocated to the segments.

Non-GAAP Financial Measures

In addition to our key financial measures presented in accordance with GAAP in the Consolidated Balance Sheets and Consolidated Statements of Income and
Comprehensive Income, management uses certain non-GAAP financial measures to evaluate the Company's financial performance and the overall growth in value
generated  for  the  Company’s  common  shareholders.  Management  believes  that  these  measures,  which  may  be  defined  and  calculated  differently  by  other
companies,  explain  the  Company’s  results  to  investors  in  a  manner  that  allows  for  a  more  complete  understanding  of  the  underlying  trends  in  the  Company’s
business. The non-GAAP financial measures should not be viewed as a substitute for those determined in accordance with U.S. GAAP. The calculation of some of
these  key  financial  measures  including  the  reconciliation  of  non-GAAP  financial  measures  to  the  nearest  GAAP  measure  and  relevant  discussions  are  found
within Item 7 - "Management's Discussion and Analysis of Financial Condition and Results of Operations". These non-GAAP financial measures are:

Non-GAAP  operating  earnings  and  non-GAAP  diluted  operating  earnings  per  common  share:  Management  believes  that  the  use  of  non-GAAP  operating
earnings and non-GAAP diluted operating earnings per common share enables investors and other users of the Company’s financial information to analyze its
performance  in  a  manner  similar  to  how  management  analyzes  performance.  Management  also  believes  that  these  measures  generally  follow  industry  practice
therefore allowing the users of financial information to compare the Company’s performance with its industry peer group, and that the equity analysts and certain
rating agencies which follow the Company, and the insurance industry as a whole, generally exclude these items from their analyses for the same reasons. Non-
GAAP operating earnings should not be viewed as a substitute for U.S. GAAP net income. Non-GAAP operating earnings is an internal performance measure
used by management as these measures focus on the underlying fundamentals of the Company's operations by excluding, on a recurring basis: (1) net realized and
unrealized investment gains (losses); (2) foreign exchange and other gains (losses); (3) the portion of favorable or unfavorable prior year reserve development for
which we have ceded the risk under the LPT/ADC Agreement and related changes in amortization of the deferred gain liability; and (4) interest in income (loss) of
equity  method  investments.  We  excluded  net  realized  and  unrealized  gains  (losses)  on  investment,  interest  in  income  (loss)  of  equity  method  investments  and
foreign exchange and other gains (losses) as we believe these are influenced by market opportunities and other factors. We do not believe that ceded risks under
the  LPT/ADC  Agreement  are  representative  of  our  ongoing  and  future  business  which  are  different  to  retroactive  reinsurance  risks  written  by  GLS  that  are
representative  of  our  ongoing  and  future  business.  We  believe  all  of  these  amounts  are  substantially  independent  of  our  business  and  any  potential  future
underwriting process, therefore, including them would distort the analysis of underlying trends in our operations.

Underwriting income (loss) is a non-GAAP measure and is calculated as net premiums earned plus other insurance revenue (expense), net less net loss and
LAE, commission and other acquisition expenses and general and administrative expenses directly related to underwriting activities. For purposes of these non-
GAAP  operating  measures,  the  fee-generating  business  which  is  included  in  our  Diversified  Reinsurance  segment,  is  considered  part  of  the  underwriting
operations of the Company. The fair value changes in underwriting-related derivative instruments is also included within other insurance (expense) revenue as the
Company considers these contracts to be part of its underwriting operations. Management believes that this measure is important in evaluating the underwriting
performance of the Company and its segments. This measure is also a useful tool to measure the profitability of the Company separately from the investment
results  and  is  also  a  widely  used  performance  indicator  in  the  insurance  industry.  A  reconciliation  of  the  Company's  underwriting  results  can  be  found  in  the
Company's Consolidated Financial Statements in the "Notes to Consolidated Financial Statements Note 3. Segment Information" included under Item 8 "Financial
Statements and Supplementary Data" of this Annual Report on Form 10-K.

The Company no longer presents certain non-GAAP measures such as combined ratio and its related components in this Annual Report on Form 10-K for the
year ended December 31, 2022, as it believes that as the run-off of our reinsurance portfolios progresses, such ratios are increasingly not meaningful and of less
value to readers as they evaluate the financial results of the Company, particularly compared to historical data.

While  an  important  metric  of  success,  underwriting  income  (loss)  does  not  reflect  all  components  of  profitability,  as  it  does  not  recognize  the  impact  of
investment income earned on premiums between the time premiums are received and the time loss payments are ultimately paid to clients. Because we do not
manage  our  cash  and  investments  by  segment,  investment  income  and  interest  expense  are  not  allocated  to  the  reportable  segments.  Certain  general  and
administrative expenses are generally allocated to segments based on actual costs incurred.

Non-GAAP  Operating  Return  on  Average  Adjusted  Common  Equity  ("Non-GAAP  Operating  ROACE"):  Management  uses  non-GAAP  operating  return  on
average adjusted common shareholders' equity as a measure of profitability that focuses on the return to common shareholders. It is calculated using non-GAAP
operating earnings available to common shareholders (as defined above) divided by average adjusted common shareholders' equity.

Book Value per Common Share and Diluted Book Value per Common Share: Book value per common share and diluted book value per common share are non-
GAAP measures. Management uses growth in both of these metrics as a prime measure of the value we are generating for our common shareholders, because
management  believes  that  growth  in  each  metric  ultimately  results  in  growth  in  the  Company’s  common  share  price.  These  metrics  are  impacted  by  the
Company’s net income and external factors, such as interest rates, which can drive changes in unrealized gains or losses on our fixed income investment portfolio,
as well as common or preference share repurchases.

Ratio  of  Debt  to  Total  Capital  Resources:  Management  uses  this  non-GAAP  measure  to  monitor  the  financial  leverage  of  the  Company.  This  measure  is

calculated using the total principal amount of debt divided by the sum of total capital resources.

41

Non-GAAP  underwriting  loss,  Non-GAAP  earnings,  and  Non-GAAP  net  loss  and  LAE:  Management  has  further  adjusted  underwriting  income,  as  defined
above, as well as reported loss and LAE by excluding the portion of favorable or unfavorable prior year reserve development for which we ceded the risk under
retroactive reinsurance agreements such as the LPT/ADC Agreement. The losses are estimated to be fully recoverable from Cavello and management believes
adjusting for this development shows the ultimate economic benefit of the LPT/ADC Agreement on our underwriting results. We believe reflecting the economic
benefit of this retroactive reinsurance agreement is helpful to understand future trends in our operations.

Adjusted  Total  Shareholders'  Equity,  Adjusted  Total  Capital  Resources,  Ratio  of  Debt  to  Adjusted  Total  Capital  Resources  and  Adjusted  Book  Value  per
Common Share: Management has adjusted GAAP shareholders' equity by adding the following items to shareholders' equity: 1) unamortized deferred gain on
ceded retroactive reinsurance under the LPT/ADC Agreement; and 2) an adjustment which reflects the equity accounting related to the fair value of certain hedged
liabilities within an equity method investment previously held by the Company wherein the ultimate realizable value of the asset supporting the hedged liabilities
cannot currently be recognized at fair value ("LP Investment Adjustment"). The unamortized deferred gain on ceded retroactive reinsurance under the LPT/ADC
Agreement includes the aggregate impact of: 1) cumulative increases to losses incurred prior to December 31, 2018 for which we have ceded the risk under the
LPT/ADC  Agreement  with  Cavello;  and  2)  changes  in  estimated  ultimate  losses  for  certain  workers'  compensation  reserves  previously  commuted  to  AmTrust
which are subject to specific terms and conditions pursuant to the LPT/ADC Agreement. As a result, by virtue of this adjustment, management has also adjusted
Total Capital Resources and computed the Ratio of Debt to Adjusted Capital Resources and Adjusted Book Value per Common Share. The deferred gain liability
on  retroactive  reinsurance  under  the  LPT/ADC  Agreement  represents  loss  reserves  estimated  to  be  fully  recoverable  from  Cavello  and  management  believes
adjusting for this shows the ultimate economic benefit of the LPT/ADC Agreement. We believe reflecting the economic benefit of this non-recurring retroactive
reinsurance agreement is helpful to understand future trends in our operations, which will improve our shareholders' equity over the settlement or contract periods,
respectively.

Alternative  investments  is  the  total  of  the  Company's  holdings  of  equity  securities,  other  investments  and  equity  method  investments  as  reported  on  the

Company's Consolidated Balance Sheets.

42

Critical Accounting Policies and Estimates

It  is  important  to  understand  our  accounting  policies  in  order  to  understand  our  financial  position  and  results  of  operations.  The  Company’s  Consolidated
Financial  Statements  have  been  prepared  in  accordance  with  U.S.  GAAP.  The  preparation  of  financial  statements  in  conformity  with  U.S.  GAAP  requires
management to make estimates and assumptions that affect the reported amounts of assets and liabilities at the date of the financial statements and the reported
amounts of revenues and expenses during the reporting period. The following presents a discussion of those accounting policies and estimates that management
believes  are  the  most  critical  to  its  operations  and  require  the  most  difficult,  subjective  and  complex  judgment.  If  actual  events  differ  significantly  from  the
underlying  assumptions  and  estimates  used  by  management,  there  could  be  material  adjustments  to  prior  estimates  that  could  potentially  adversely  affect  the
Company’s results of operations, financial condition and liquidity. These critical accounting policies and estimates should be read in conjunction with "Notes to
Consolidated  Financial  Statements  -  Note  2.  Significant  Accounting  Policies"  included  under  Item  8  "Financial  Statements  and  Supplementary  Data"  of  this
Annual Report Form 10-K for a full understanding of the Company’s accounting policies.

Reserve for Loss and LAE

General: The amount of time that elapses before a claim is reported to the cedant and then subsequently reported to the reinsurer is commonly referred to in the
industry  as  the  reporting  tail.  Lines  of  business  for  which  claims  are  reported  quickly  are  commonly  referred  to  as  short-tailed  lines;  and  lines  of  business  for
which a longer period of time elapses before claims are reported to the reinsurer are commonly referred to as long-tailed lines. In general, for reinsurance, the time
lags are longer than for primary business due to the delay that occurs between the cedant becoming aware of a loss and reporting the information to its reinsurer(s).
The delay varies by reinsurance market (country of cedant), type of treaty, whether losses are paid by the cedant and the size of the loss. The delay could vary
from a few weeks to a year or sometimes longer.

Because a significant amount of time can elapse, particularly on longer-tail lines of business written on an excess of loss basis, between the assumption of risk,
the occurrence of a loss event, the reporting of the event to an insurance company (the primary company or the cedant), the subsequent reporting to the reinsurance
company  ("the  reinsurer")  and  the  ultimate  payment  of  the  claim  on  the  loss  event  by  the  reinsurer,  the  Company’s  liability  for  unpaid  loss  and  LAE  ("loss
reserves") is based largely upon estimates. The Company categorizes loss reserves into two types of reserves: reported outstanding loss reserves ("case reserves")
and IBNR reserves. Case reserves represent, for each individual claim, an estimate of unpaid losses, either by the Company’s cedants or the Company’s claims
handling  professionals,  and  recorded  by  the  Company.  IBNR  reserves  represent  a  provision  for  claims  that  have  been  incurred  but  not  yet  reported  to  the
Company,  as  well  as  future  loss  development  on  losses  already  reported,  in  excess  of  the  case  reserves.  The  Company  updates  its  estimates  for  each  of  the
aforementioned categories primarily on a quarterly basis using information received from its cedants.

For excess of loss treaties, cedants generally are required to report losses that either (i) exceed 50% of their retention; or (ii) have a reasonable probability of
exceeding the retention; or (iii) meet defined reporting criteria. All excess of loss reinsurance claims that are reserved are reviewed on a periodic basis. In addition,
reserves  for  loss  and  LAE  are  reviewed  every  quarter  for  each  cedant.  For  proportional  treaties,  cedants  are  required  to  give  a  periodic  statement  of  account,
generally  monthly  or  quarterly.  These  periodic  statements  typically  include  information  regarding  premiums  written,  premiums  earned,  unearned  premiums,
ceding commissions, brokerage amounts, applicable taxes, paid losses and reported outstanding losses. They can be submitted up to ninety days after the close of
the reporting period. Some proportional treaties have specific language requiring earlier notice of serious claims.

For  all  lines,  the  Company’s  objective  is  to  reasonably  estimate  ultimate  loss  and  LAE.  Total  loss  reserves  are  then  calculated  by  subtracting  losses  paid.
Similarly,  IBNR  reserves  are  calculated  by  subtracting  case  reserves  from  total  loss  reserves.  IBNR  is  the  estimated  liability  for:  (1)  changes  in  the  values  of
claims  that  have  been  reported  to  us  but  are  not  yet  settled;  (2)  claims  that  have  occurred  but  have  not  yet  been  reported;  and  (3)  claims  that  are  closed  but
subsequently reopened. Each claim is settled individually based upon its merits, and particularly for longer-tailed lines of business, it is not unusual for a claim to
take several years after being initially reported to be settled and paid, especially if legal action is involved. These claims may also require changes in anticipated
future payments due to changes in medical conditions or changes in expected inflationary pressures. As a result, the reserve for loss and LAE includes significant
estimates for IBNR reserves.

The  reserve  for  IBNR  is  generally  estimated  by  management  based  on  various  factors,  including  actuarial  analysis  and  actual  loss  experience  to  date.  Our
actuaries  employ  standard  actuarial  methodologies  to  determine  estimated  ultimate  loss  reserves.  In  selecting  management's  best  estimate  of  loss  and  LAE
reserves,  we  consider  the  range  of  results  produced  by  many  actuarial  methods  and  the  appropriateness  of  those  estimates.  These  actuarial  methodologies  are
described in "Notes to Consolidated Financial Statements - Note 9. Reserve for Loss and Loss Adjustment Expenses" included under Item 8 "Financial Statement
and Supplementary Data".

The composition of the reserve for loss and LAE at December 31, 2022 and 2021 was as follows:

December 31,

Reserve for reported loss and LAE
Reserve for losses incurred but not reported

Reserve for loss and LAE

2022

2021

($ in thousands)

$

$

702,691  $
428,717 
1,131,408  $

851,950 
637,423 
1,489,373 

43

The  loss  reserves  in  the  table  above  exclude  the  impact  of  the  LPT/ADC  Agreement.  While  management  believes  that  our  case  reserves  and  IBNR  are
sufficient to cover losses assumed by us, there can be no assurance that losses will not deviate from our reserves, possibly by material amounts. The analysis of the
appropriateness of the reserve for IBNR is reviewed quarterly, with adjustments made as appropriate. To the extent that actual reported losses exceed expected
losses, the carried estimate of the ultimate losses may be increased (i.e. unfavorable reserve development), and to the extent actual reported losses are less than our
expectations, the carried estimate of ultimate losses may be reduced (i.e. favorable reserve development). We record any changes in our loss reserve estimates and
the related reinsurance recoverable in the periods in which they are determined. Reinsurance recoverable on unpaid losses covered by the ADC portion of the
LPT/ADC  Agreement  are  recorded  as  part  of  the  deferred  gain  on  retroactive  reinsurance  shown  on  the  Consolidated  Balance  Sheets  which  represents  the
cumulative adverse loss development under the AmTrust Quota Share covered by the LPT/ADC Agreement at December 31, 2022. Amortization of the deferred
gain will not occur until paid losses have exceeded the minimum retention under the LPT/ADC Agreement, which is estimated to be in 2025.

Loss reserves do not represent an exact calculation of liability. Rather, loss reserves are estimates of what we reasonably expect the ultimate resolution and
administration of claims will cost. These estimates are based on actuarial projections and on our assessment of currently available data, as well as estimates of
future  trends  in  claims  severity  and  frequency,  judicial  theories  of  liability  and  other  factors.  Loss  reserve  estimates  are  refined  as  experience  develops  and  as
claims are reported and resolved. In addition, the relatively long periods between when a loss occurs and when it may be reported to our claims department for our
casualty reinsurance lines of business also increase the uncertainties of reserve estimates in such lines.

With  the  guidance  of  the  methods  described  in  "Notes  to  Consolidated  Financial  Statements  -  Note  9.  Reserve  for  Loss  and  Loss  Adjustment  Expenses"
included under Item 8 "Financial Statement and Supplementary Data" of this Annual Report on Form 10-K, actuarial judgment is applied in the determination of
ultimate losses. In general, the Company’s segments have varying levels of seasoning with which the Company has direct experience and as a result, differing
methods are utilized to estimate loss and LAE reserves within each segment.

In our Diversified Reinsurance segment, we hold books of business that have been in runoff for several years, as well as books of business that have been
underwritten only during the last few years. In general, we utilize the Expected Loss Ratio ("ELR") approach at the onset of reserving an account, the Bornhuetter-
Ferguson  ("BF")  method  for  business  with  less  but  maturing  loss  experience,  and  then,  as  the  experience  matures,  the  Loss  Development  ("LD")  method  is
utilized.  The  runoff  book  of  business  primarily  uses  the  LD  method  due  to  its  maturity  and  the  amount  of  experience  which  has  emerged  over  the  years.  For
proportional business, the Company relies heavily on the actual contract experience, whereas for excess of loss business, there will be more usage of industry
and/or Company specific benchmark assumptions in the reserving process.

The Company underwrote the AmTrust Reinsurance segment from July 1, 2007 until Maiden Reinsurance and AII agreed to terminate the remaining business
subject  to  the  AmTrust  Quota  Share  and  European  Hospital  Liability  Quota  Share,  both  on  a  run-off  basis,  effective  January  1,  2019.  A  large  portion  of  the
exposure  in  the  underlying  book  of  business  has  significant  seasoning,  and  allows  for  a  significant  amount  of  credibility  in  using  parameters  derived  from
historical experience to calculate reserve estimates. Some segments of the book are a result of recent acquisitions or newer markets for AmTrust. These segments
require a greater level of assumptions and professional judgment in deriving reserve levels, which inherently implies a wider range of reasonable estimates. In
addition, changes to case reserving and claims settlement practices by AmTrust have required the use of methods which adjust historical paid and incurred losses
to reflect the current basis. As a result, we have tended to rely on a weighted approach which primarily employs the LD method for aspects of the segment with
ample historical data, while also considering the ELR or BF method for exposure resulting from recent acquisitions, or a relative business with a more limited
level of experience. The LD method can also be based on AmTrust specific historical information, historical information adjusted to current levels, or information
derived  from  industry  sources,  with  actuarial  judgment  being  used  as  to  the  credibility  weighting  employed.  The  Frequency-Severity  ("FS")  method  is  also
considered for segments of the AmTrust book for which claim count information is available. Additional data detailing items such as the class of business, state of
occurrence, claim counts, and the frequency and severity of claims is available in many instances, further enhancing the loss reserve analysis.

Significant  Assumptions  Employed  in  the  Estimation  of  Reserve  for  Loss  and  Loss  Adjustment  Expenses:  The  most  significant  assumptions  used  at

December 31, 2022 to estimate the reserve for loss and LAE within our reporting segments are as follows:

• the information developed from internal and independent external sources can be used to develop meaningful estimates of the likely future performance

of business bound by the Company;

• the loss and exposure information provided by ceding companies, insureds and brokers in support of their reinsurance submissions have been used by the
Company's pricing actuaries to derive meaningful estimates of the likely future performance of business bound with respect to each contract and policy;

• historic loss development and trend experience may be used to predict future loss development and trends;

• no significant emergence of losses or types of losses that are not represented in the information supplied to the Company by its brokers, ceding companies

and insureds will occur; and

• the Company is able to identify and properly adjust for changes to case reserving and claims settlement rates in the underlying data.

The  five  assumptions  above  significantly  influence  the  Company’s  determination  of  initial  expected  loss  ratios  and  expected  loss  reporting  and  payment

patterns that are the key inputs which impact potential variability in the estimate of the

44

reserve for loss and LAE and are applicable to each of the Company’s business segments. These factors are combined with the actuarial judgment exercised by our
reserving actuaries. While there can be no assurance that any of the above assumptions will prove to be correct, we believe that this process represents a realistic
and appropriate basis for estimating the reserve for loss and LAE. Loss emergence factors and expected loss ratios used in the reserving process are based on a
blend of our own direct experience, cedant experience and industry benchmarks, when appropriate. The benchmarks selected were those that we believe are most
similar to our underwriting business.

Factors Creating Uncertainty in the Estimation of the Reserve for Loss and Loss Adjustment Expenses: While  management  does  not  include  an  explicit  or
implicit provision for uncertainty in its reserve for loss and LAE, certain of the Company’s business lines are by their nature subject to additional uncertainties,
which are discussed in detail below. In addition, the Company’s reserves are subject to additional factors which add to the uncertainty of estimating reserve for
loss and LAE. Time lags in the reporting of losses can also introduce further ambiguity to the process of estimating reserve for loss and LAE.

The inherent uncertainty of estimating the Company’s reserve for loss and LAE increases principally due to:

• the  lag  in  time  between  the  time  claims  are  initially  reported  to  the  ceding  company  and  the  time  they  are  ultimately  reported  through  one  or  more

reinsurance broker intermediaries to the Company;

• the differing case reserving practices among ceding companies;

• changes to characteristics of a claim over time, such as future medical needs or assessment of liability;

• the diversity of loss development patterns among different types of reinsurance treaties or contracts;

• the Company’s need to rely on its ceding companies for loss information, which also exposes the Company to changes in the reserving philosophy of the

ceding company and the adequacy of its underlying case reserves; and

• changes in internal company operations such as alterations in claims handling procedures.

To verify the accuracy and completeness of the information provided to us by our ceding company counterparties, the Company’s actuaries, accountants and
claims  personnel  perform  claims  reviews,  and  at  times  also  accounting  and  financial  audits,  of  the  Company’s  ceding  companies.  Any  material  findings  are
communicated to the ceding companies and utilized in the establishment or revision of the Company’s case reserves and related IBNR reserve. On occasion, these
reviews  reveal  that  the  ceding  company’s  reported  loss  and  LAE  do  not  comport  with  the  terms  of  the  contract  held  with  the  Company.  In  such  events,  the
Company strives to resolve the outstanding differences in an amicable fashion. The large majority of such differences are resolved in this manner. In the infrequent
instance where an amicable solution is not feasible, the Company’s policy is to vigorously defend its position in litigation or arbitration. At December 31, 2022,
the Company was not involved in any material claims litigation or arbitration proceedings.

Due to the large volume of potential transactions that must be recorded in the insurance and reinsurance industry, backlogs in the recording of the Company’s
business activities can also impair the accuracy of its loss and LAE reserve estimates. At December 31, 2022, there were no significant backlogs related to the
processing of policy or contract information in any of our reporting segments.

The Company assumes in its loss and LAE reserving process that, on average, the time period between the recording of expected losses and the reporting of
actual losses are predictable when measured in the aggregate and over time. The time period over which all losses are expected to be reported to the Company
varies  significantly  by  line  of  business.  This  period  can  range  from  a  few  quarters  for  some  lines,  such  as  property,  to  many  years  for  some  casualty  lines  of
business. To the extent that actual reported losses are reported more quickly or more slowly than expected, the Company may adjust its estimate of ultimate loss
accordingly.

Potential Volatility in the Reserve for Loss and LAE: In addition to the factors creating uncertainty in the Company’s estimate of loss and LAE, the Company’s
estimated reserve for loss and LAE can change over time because of unexpected changes in the external environment. Potential changing external factors include:

• changes in the inflation rate for goods and services related to the covered damages;

• changes in the general economic environment that could cause unanticipated changes in claim frequency or severity;

• changes in the litigation environment regarding the representation of plaintiffs and potential plaintiffs;

• changes  in  the  judicial  and/or  arbitration  environment  regarding  the  interpretation  of  policy  and  contract  provisions  relating  to  the  determination  of

coverage and/or the amount of damages awarded for certain types of claims;

• changes in the social environment regarding the general attitude of juries in the determination of liability and damages;

• changes in the legislative environment regarding the definition of damages;

• new types of injuries caused by new types of injurious activities or exposures; and

• assessment of changes in ceding company case reserving and reporting patterns.

The change in loss reserve estimates from the prior year is referred to as Prior Year Development ("PPD"). We experienced adverse PPD of $32.6 million for
the year ended December 31, 2022 compared to favorable PPD of $27.6 million for the year ended December 31, 2021, primarily within the AmTrust Reinsurance
segment.

45

Please refer to “Notes to Consolidated Financial Statements - Note 9 — Reserve for Loss and Loss Adjustment Expenses” included under Item 8. "Financial

Statements and Supplementary Data" of this Form 10-K for further details.

The  Company  creates  a  statistical  distribution  around  the  estimate  of  reserve  for  loss  and  LAE  based  on  an  assumption  of  the  volatility  inherent  in  the
estimate. The Company, in the analysis of reserves for loss and LAE, in addition to selecting a best point estimate, makes a selection of a range of reasonable
reserves.  This  range  is  based  on  a  combination  of  objective  and  subjective  data,  including  the  underlying  characteristics  of  the  exposure,  the  volatility  in
historical emergence, the credibility of the information available to estimate the reserve for loss and LAE, and professional actuarial judgement. The size of the
range is related to the level of confidence associated with the point estimate, as well as the amount of uncertainty inherent in the characteristics of the exposure
being evaluated.

Based on this range of reasonable reserves, our required reserves after reinsurance recoverable could increase by approximately $153.0 million, or 14.3%, of
our consolidated net loss and LAE reserves, excluding the impact of the LPT/ADC Agreement. If the LPT/ADC Agreement were to be considered, our required
reserves could increase by approximately $73.0 million, or 12.6% of our consolidated net loss and LAE reserves.

For  the  range  of  reasonable  reserves,  we  have  assumed  what  we  believe  is  an  appropriate  confidence  level.  However,  the  range  is  not  intended  to  be  a

measurement of all possible future outcomes, and there can be no assurance that our claim obligation will not vary outside of this range.

Premiums and Commissions and Other Acquisition Expenses

For pro-rata contracts and excess-of-loss contracts where no deposit or minimum premium is specified in the contract, premium written is recognized based on
estimates of ultimate premiums provided by the ceding companies. Initial estimates of premium written are recognized in the period in which the underlying risks
are incepted. Subsequent adjustments, based on reports of actual premium by the ceding companies, or revisions in estimates, are recorded in the period in which
they are determined. Reinsurance premiums assumed are generally earned on a pro rata basis over the terms of the underlying policies or reinsurance contracts.

Contracts and policies written on a "losses occurring" basis cover claims that may occur during the term of the contract or policy, which is typically twelve
months.  Accordingly,  the  premium  is  earned  evenly  over  the  contract  term.  Contracts  which  are  written  on  a  "risks  attaching"  basis  cover  claims  from  all
underlying insurance policies written during the terms of such contracts. Premiums earned on such contracts extend beyond the original term of the reinsurance
contract, typically resulting in recognition of premiums earned over a twenty-four-month period.

Reinsurance premiums on specialty risk and extended warranty are earned based on the estimated program coverage period. These estimates are based on the
expected distribution of coverage periods by contract at inception, because a single contract may contain multiple coverage period options and these estimates are
revised based on the actual coverage period selected by the original insured.

Unearned premiums represent the portion of premiums written which is applicable to the unexpired term of the contract or policy in force. These premiums can
be  subject  to  estimates  based  upon  information  received  from  ceding  companies  and  any  subsequent  differences  arising  on  such  estimates  are  recorded  in  the
period in which they are determined.

The Company provides proportional and non-proportional reinsurance coverage to cedants (insurance companies). Cedants' actual premiums are unknown at
the time they enter into reinsurance agreement so treaties are based upon estimates of those premiums at the time the treaties are written and are typically adjusted
as premiums are known. Reporting delays are inherent in the reinsurance industry and vary in length by type of treaty. As delays can vary from a few weeks to a
year or sometimes longer, the Company produces accounting estimates to report premiums and commission and other acquisition expenses until it receives the
cedants’  actual  results.  Under  proportional  treaties,  the  Company  shares  proportionally  in  both  the  premiums  and  losses  of  the  cedant  and  pays  the  cedant  a
commission to cover the cedants' acquisition expenses. Under this type of treaty, the Company’s ultimate premiums written and earned and acquisition expenses
are not known at the inception of the treaty and must be estimated until the cedant reports its actual results to the Company. Under non-proportional treaties, the
Company  is  typically  exposed  to  loss  events  in  excess  of  a  predetermined  dollar  amount  or  loss  ratio  and  receives  a  deposit  or  minimum  premium,  which  is
subject to adjustment depending on the premium volume written by the cedant.

Reported premiums written and earned and commission and other acquisition expenses on proportional treaties are generally based upon reports received from
cedants  and  brokers,  supplemented  by  the  Company’s  own  estimates  of  premiums  written  and  commission  and  other  acquisition  expenses  for  which  ceding
company reports have not been received. Premium and acquisition expense estimates are determined at the individual treaty level based upon contract provisions.
The determination of estimates requires a review of the Company’s experience with cedants, a thorough understanding of the individual characteristics of each line
of business and the ability to project the impact of current economic indicators on the volume of business written and ceded by the Company’s cedants. Estimates
for premiums and commission and other acquisition expenses are updated continuously as new information is received from the cedants. Differences between such
estimates and actual amounts are recorded in the period in which estimates are changed or the actual amounts are determined.

Assessing  whether  or  not  a  reinsurance  contract  meets  the  condition  for  risk  transfer  requires  judgment.  The  determination  of  risk  transfer  is  critical  to
reporting premiums written and is based, in part, on the use of actuarial and pricing models and assumptions. If we determine that a reinsurance contract does not
transfer sufficient risk, we account for the contract as a deposit liability rather than a premium written.

46

Acquisition expenses represent the costs of writing business that vary with, and are primarily related to, the production of the business. Acquisition expenses
that  are  related  to  successful  contracts  are  deferred  and  recognized  as  expense  over  the  same  period  in  which  the  related  premiums  are  earned.  Only  certain
expenses incurred in the successful acquisition of new and renewal insurance contracts are capitalized. Those expenses include incremental direct costs of contract
acquisition that result directly from and are essential to the contract transaction and would not have been incurred had the contract transaction not occurred. All
other acquisition-related expenses, such as costs incurred for soliciting business, administration, and unsuccessful acquisition or renewal efforts are charged to
expense as incurred. Administrative expenses, including rent, depreciation, occupancy, equipment, and all other general overhead expenses are considered indirect
and are expensed as incurred.

The  Company  considers  anticipated  investment  income  in  determining  the  recoverability  of  these  deferred  costs  and  believes  they  are  fully  recoverable.  A
premium deficiency is recognized if the sum of anticipated losses and LAE, unamortized acquisition expenses and anticipated investment income exceed unearned
premium.

Retroactive Reinsurance

Retroactive reinsurance policies provide indemnification for losses and LAE with respect to past loss events. For our GLS run-off business in our Diversified
Reinsurance segment, we use the balance sheet accounting approach for assumed loss portfolio transfers, whereby at the inception of the contract there are no
premiums or losses recorded in earnings.

At the inception of a run-off retroactive reinsurance contract, if the estimated undiscounted ultimate losses payable are in excess of the premiums received, a
deferred charge asset is recorded for the excess; whereas, if the premiums received are in excess of the estimated undiscounted ultimate losses payable, a deferred
gain  liability  is  recorded  for  the  excess,  such  that  we  do  not  record  any  gain  or  loss  at  the  inception  of  these  retroactive  reinsurance  contracts.  The  premium
consideration that we charge the ceding companies under retroactive reinsurance contracts may be lower than the undiscounted estimated ultimate losses payable
due  to  the  time  value  of  money.  After  receiving  the  premium  consideration  in  full  from  our  cedents  at  the  inception  of  the  contract,  we  invest  the  premium
received over an extended period of time, thereby generating investment income. We expect to generate profits from these retroactive reinsurance contracts when
taking into account the premium received and expected investment income, less contractual obligations and expenses.

Deferred charge assets will be recorded in other assets (if and when applicable), and deferred gain liabilities are recorded in other liabilities, and amortized over
the  estimated  claim  payment  period  of  the  related  contract  with  the  periodic  amortization  reflected  in  earnings  as  a  component  of  losses  and  LAE.  The
amortization  of  deferred  charge  assets  and  deferred  gain  liabilities  is  adjusted  at  each  reporting  period  to  reflect  new  estimates  of  the  amount  and  timing  of
remaining loss and LAE payments. Changes in the estimated amount and timing of payments of unpaid losses may have an effect on the unamortized deferred
charge assets and deferred gain liabilities and the amount of periodic amortization.

Fair Value of Financial Instruments

Please refer to "Notes to Consolidated Financial Statements - Note 5. Fair Value of Financial Instruments" included under Item 8 "Financial Statements and
Supplementary  Data"  of  this  Annual  Report  on  Form  10-K  for  a  discussion  on  the  fair  value  methodology  and  valuation  techniques  used  by  the  Company  to
determine the fair value of the financial instruments held at December 31, 2022 and 2021.

Other-Than-Temporary Impairment ("OTTI") of Investments

Please  refer  to  "Notes  to  Consolidated  Financial  Statements  -  Note  2.  Significant  Accounting  Policies"  included  under  Item  8  "Financial  Statements  and
Supplementary Data" of this Annual Report on Form 10-K for a discussion on the impairment evaluation performed by the Company on its investment portfolio.
For the years ended December 31, 2022 and December 31, 2021, the Company did not recognize any OTTI impairment losses in its results of operation. Please
see "Notes to Consolidated Financial Statements: Note 4. Investments"  included  under  Item  8  "Financial  Statements  and  Supplementary  Data"  of  this  Annual
Report on Form 10-K for further details.

47

Results of Operations

The following table sets forth our selected Consolidated Statement of Income data for each of the years indicated:

For the Year Ended December 31,

Gross premiums written

Net premiums written
Net premiums earned
Other insurance (expense) revenue, net
Net loss and LAE
Commission and other acquisition expenses
General and administrative expenses
Underwriting (loss) income
Other general and administrative expenses
Net investment income
Net realized and unrealized (losses) gains on investment
Foreign exchange and other gains
Interest and amortization expenses

(1)

(1)

(2)

Income tax benefit (expense)
Interest in (loss) income in equity method investments
Net (loss) income

Gain from repurchase and exchange of preference shares

Net income available to Maiden common shareholders

2022

2021

($ in thousands)
5,479  $

5,082  $

37,732  $
(4,530)
(57,991)
(18,511)
(11,634)
(54,934)
(19,313)
30,070 
(5,140)
8,255 
(19,331)
557 
(205)
(60,041)
115,473 
55,432  $

10,938 

10,403 

52,993 
1,067 
(7,307)
(24,840)
(10,341)
11,572 
(25,679)
32,013 
12,648 
7,685 
(19,327)
(15)
7,748 
26,645 
90,998 
117,643 

$

$

$

$

(1) Underwriting  related  general  and  administrative  expenses  is  a  non-GAAP  measure.  Please  refer  to  "General  and  Administrative  Expenses"  below for  additional  information  related  to  these

corporate expenses and the reconciliation to those presented in our Consolidated Statements of Income.

(2) Underwriting income (loss) is a non-GAAP measure and is calculated as net premiums earned plus other insurance revenue (expense), less net loss and LAE, commission and other acquisition

expenses and general and administrative expenses directly related to underwriting activities.

(3) The  Company  no  longer  presents  certain  non-GAAP  measures  such  as  combined  ratio  and  its  related  components  in  its  results  of  operation,  as  it  believes  that  as  the  run-off  of  its  reinsurance

portfolios progresses, such ratios are increasingly not meaningful and of less value to readers as they evaluate our financial results.

Net Income

Net income available to Maiden common shareholders for the year ended December 31, 2022 was $55.4 million compared to net income available to Maiden

common shareholders of $117.6 million in 2021.

The net income for the year ended December 31, 2022 included combined gains from the Exchange and repurchase of our Preference Shares of $115.5 million

for the year ended December 31, 2022 compared to the gain of $91.0 million for Preference Share repurchases during 2021.

Excluding the combined gain on the Exchange and repurchase of our Preference Shares, our net loss for the year ended December 31, 2022 was $60.0 million

compared to net income of $26.6 million in 2021. The net decrease in results for the year ended December 31, 2022 compared to 2021 was primarily due to:

• underwriting loss of $54.9 million in the year ended December 31, 2022 compared to underwriting income of $11.6 million in the same period in 2021

largely due to:

• adverse  prior  year  loss  development  of  $32.6  million  for  the  year  ended  December  31,  2022  compared  to  favorable  development  of  $27.6

million in 2021 detailed as follows:

• Our  AmTrust  Reinsurance  segment  had  adverse  prior  year  loss  development  of  $28.1  million  for  2022,  compared  to  favorable  prior

year loss development of $24.0 million in 2021.     

• Our Diversified Reinsurance segment had adverse prior year loss reserve development of $4.6 million for 2022, including $1.8 million

of adverse development in GLS, compared to favorable development of $3.6 million in 2021;

• on a current accident year basis, an underwriting loss of $22.3 million for the year ended December 31, 2022 compared to an underwriting loss
of $16.0 million in 2021, primarily due to results in AmTrust Reinsurance segment and Diversified Reinsurance segment as discussed further
below in the segment analysis;

48

• negative earned premium adjustments of $15.8 million in the AmTrust Reinsurance segment related to premium adjustments for surcharges on
Workers'  Compensation  policies  and  inuring  AmTrust  reinsurance  for  certain  programs  in  Specialty  Risk  and  Extended  Warranty  cessions
(collectively  the  "AmTrust  Cession  Adjustments"  which  are  discussed  in  greater  detail  in  the  AmTrust  Reinsurance  segment).  Net  of
commission and loss adjustments, this contributed an underwriting loss of $5.1 million to our reported results for the year ended December 31,
2022; and

• an exit cost of $3.7 million for the Commutation Agreement in our AmTrust Reinsurance segment.

• total  income  from  investment  activities  was  $24.7  million  for  the  year  ended  December  31,  2022  compared  to  $52.4  million  in  2021  which  was

comprised of:

• net investment income decreased to $30.1 million for the year ended December 31, 2022 compared to $32.0 million in 2021, as a decline in

average fixed income assets of 31.7% was partially offset by higher yields on these assets as interest rates rose during 2022;

• realized and unrealized losses on investment of $5.1 million for the year ended December 31, 2022 compared to realized and unrealized gains of

$12.6 million in 2021; and

• interest in loss of equity method investments of $0.2 million for the year ended December 31, 2022 compared to an interest in income of equity

method investments of $7.7 million in 2021.

The decrease in our results as discussed above was partially offset by the following:

• corporate general and administrative expenses decreased to $19.3 million for the year ended December 31, 2022 compared to $25.7 million in 2021; and

• foreign exchange and other gains increased to $8.3 million for the year ended December 31, 2022 compared to foreign exchange and other gains of $7.7

million in 2021.

Net Premiums Written

The table below compares net premiums written by our reportable segments, reconciled to the total consolidated net premiums written for the years ended

December 31, 2022 and 2021:

For the Year Ended December 31,
($ in thousands)
Diversified Reinsurance
AmTrust Reinsurance

Total

2022
Total

2021
Total

Change in

$

%

$

$

23,620  $
(18,538)

5,082  $

16,098  $
(5,695)
10,403  $

7,522 
(12,843)
(5,321)

46.7 %
225.5 %

(51.1)%

Net premiums written for the year ended December 31, 2022 were $5.1 million compared to net premiums written of $10.4 million during 2021 due to the

following:

• Net premiums written in the Diversified Reinsurance segment increased by $7.5 million or 46.7% for the year ended December 31, 2022 compared to
2021 primarily due to the prior year return of unearned premiums written in a German Auto quota share reinsurance contract in our IIS business which
went into run-off on January 1, 2021 as well as direct premiums written by Maiden LF and Maiden GF which increased by $3.0 million or 14.0% during
the year ended December 31, 2022 compared to 2021; and

• Negative  premiums  written  in  the  AmTrust  Reinsurance  segment  for  the  year  ended  December  31,  2022  was  primarily  related  to  $15.8  million  of

AmTrust Cession Adjustments.

Please refer to the analysis below of our Diversified Reinsurance and AmTrust Reinsurance segments for further details.

Net Premiums Earned

Net premiums earned decreased by $15.3 million or 28.8% for the year ended December 31, 2022 compared to 2021. The table below compares net premiums

earned by our reportable segments, reconciled to the total consolidated net premiums earned, for the years ended December 31, 2022 and 2021:

For the Year Ended December 31,
($ in thousands)
Diversified Reinsurance
AmTrust Reinsurance

Total

2022
Total

2021
Total

Change in

$

%

$

$

27,983  $
9,749 
37,732  $

27,681  $
25,312 
52,993  $

302 
(15,563)
(15,261)

1.1 %
(61.5)%

(28.8)%

Net premiums earned in the AmTrust Reinsurance segment for the year ended December 31, 2022 decreased by $15.6 million or 61.5% compared to 2021

primarily due to $15.8 million of AmTrust Cession Adjustments. Please refer to the analysis of our AmTrust Reinsurance segment for further discussion.

49

Net premiums earned in the Diversified Reinsurance segment for the year ended December 31, 2022 increased by $0.3 million or 1.1% compared to 2021.

Please refer to the analysis of our Diversified Reinsurance segment for further discussion.

Other Insurance Revenue (Expense), Net

All other insurance revenue (expense), net is produced by our Diversified Reinsurance segment. Please refer to the analysis of our Diversified Reinsurance

segment for further discussion regarding the sources of other insurance revenue (expense), net.

Net Investment Income

Net investment income decreased by $1.9 million or 6.1% for the year ended December 31, 2022 compared to 2021. This was primarily due to a decline in
average  aggregate  fixed  income  assets  of  31.7%  driven  by  continued  run-off  of  reinsurance  liabilities  previously  written  on  prospective  risks,  resulting  in
significant  negative  operating  cash  flows  as  we  run-off  our  existing  reinsurance  liabilities.  Net  investment  income  for  the  year  ended  December  31,  2022  was
favorably impacted by a reversal of investment expense relating to certain alternative investments, which was a non-recurring item.

Net investment income experienced an increase in annualized average book yields to 2.2% for the year ended December 31, 2022 compared to 1.9% in 2021.
Despite the sharp decline in average invested fixed income assets noted above, net investment income decreased at a much lower rate due to the following factors:

shorter duration on our fixed income portfolio combined with 29.6% of fixed income investments as of December 31, 2022 are floating rate investments

•
which enabled us to take advantage of a higher interest rate environment by reinvesting at higher yields more quickly;
•
ended December 31, 2022, which increased to 2.1% in 2022 from 1.8% in 2021; and
•

a higher weighted average interest rate on our loan to related party of $168.0 million which increased to 3.7% in 2022 from 2.1% in 2021.

a  higher  crediting  interest  rate  on  our  funds  withheld  balance  with  AmTrust,  which  had  an  average  ending  balance  of  $514.4  million  during  the  year

The following table details our average aggregate fixed income assets (at cost) and investment book yield for the years ended December 31, 2022 and 2021:

For the Year Ended December 31,

Average aggregate fixed income assets, at cost 
Annualized investment book yield

(1)

2022

2021

($ in thousands)

$

1,226,134

$

1,794,173

2.2 %

1.9 %

(1) Fixed income assets include AFS securities, cash and restricted cash, funds held receivable, and loan to related party. These amounts are an average of the amounts disclosed in our quarterly U.S.

GAAP consolidated financial statements.

Net Realized and Unrealized Investment (Losses) Gains

Net realized and unrealized investment losses of $5.1 million for the year ended December 31, 2022, and net realized and unrealized investment gains of $12.6
million for 2021 primarily reflect sales of fixed maturity bonds for the settlement of claim payments to AmTrust, the sale of which resulted in net realized losses
of $3.0 million in 2022 compared to net realized gains of $9.1 million in 2021. The table below shows the breakdown of net realized investment gains (losses) and
net unrealized investment gains (losses) by investment category for the years ended December 31, 2022 and 2021:

For the Year Ended December 31,

Net realized investment (losses) gains - Fixed maturity securities

Net realized investment gains - Equity securities
Net unrealized investment gains - Equity securities
Net realized and unrealized investment gains - Equity securities

Net realized investment gains - Other investments
Net unrealized investment (losses) gains - Other investments
Net realized and unrealized investment (losses) gains - Other investments

2022

2021

$

($ in thousands)

(2,983) $

111 
2,225 
2,336 

79 
(4,572)
(4,493)

9,097 

441 
335 
776 

275 
2,500 
2,775 

Total net realized and unrealized investment (losses) gains

$

(5,140) $

12,648 

50

The following table summarizes our net realized and unrealized investment gains (losses) for the years ended December 31, 2022 and 2021, respectively:

For the Year Ended December 31,
Net realized (losses) gains:
Fixed income assets
Other investments, including equity securities
Total net realized (losses) gains

(1)

Net unrealized (losses) gains:
Other investments, including equity securities
Total net unrealized (losses) gains

Total net realized and unrealized investment (losses) gains

Interest in Income (Loss) of Equity Method Investments

2022

2021

($ in thousands)

(2,983)
190 
(2,793)

(2,347)
(2,347)

9,097 
716 
9,813 

2,835 
2,835 

$

(5,140) $

12,648 

The interest in loss of equity method investments was $0.2 million for the year ended December 31, 2022 compared to an interest in income of equity method
investments of $7.7 million for the year ended December 31, 2021. The results from equity method investments decreased by $8.0 million primarily due to a $5.1
million loss in our hedge fund equity method investments during the year ended December 31, 2022.

The Company's equity method investments include hedge fund investments of $5.4 million, real estate investments of $40.9 million and other investments of
$33.8  million  as  of  December  31,  2022.  The  following  table  details  our  interest  in  the  (loss)  income  of  equity  method  investments  for  the  years  ended
December 31, 2022 and 2021, respectively:

For the Year Ended December 31,

Hedge fund investments
Real estate investments
Other equity method investments

Interest in (loss) income of equity method investments

Net Loss and Loss Adjustment Expenses

2022

2021

($ in thousands)

$

$

(5,053) $
29 
4,819 
(205) $

3,494 
— 
4,254 
7,748 

Net loss and LAE increased by $50.7 million during the year ended December 31, 2022 compared to 2021 largely due to significant net adverse prior year loss
development in the AmTrust Reinsurance Segment compared to considerable favorable development experienced in this segment for 2021. The cessation of active
reinsurance  underwriting  on  prospective  risks  included  the  termination  of  the  AmTrust  Quota  Share  and  European  Hospital  Liability  Quota  Share  effective
January 1, 2019.

Net  loss  and  LAE  for  2022  was  impacted  by  net  adverse  prior  year  reserve  development  of  $32.6  million  compared  to  net  favorable  prior  year  reserve
development  of  $27.6  million  during  2021.  The  prior  year  development  is  discussed  in  greater  detail  in  the  individual  segment  discussion  and  analysis  and  is
primarily associated with the run-off of terminated reinsurance contracts in the AmTrust Reinsurance and Diversified Reinsurance segments.

Commission and Other Acquisition Expenses

Commission and other acquisition expenses decreased by $6.3 million or 25.5% for the year ended December 31, 2022 compared to 2021 primarily due to
negative earned premiums in the AmTrust Reinsurance segment which reduced commission costs related to the AmTrust Cession Adjustments by $5.4 million.
Please see further discussion in the individual segment analysis below.

General and Administrative Expenses

General and administrative expenses include both segment and corporate expenses segregated for analytical purposes as a component of underwriting income.
Total general and administrative expenses decreased by $5.1 million or 14.1% for the year ended December 31, 2022, compared to 2021 primarily due to lower
corporate-related administrative expenses.

Corporate general and administrative expenses for the year ended December 31, 2022 decreased by $6.4 million or 24.8% compared to 2021 due to lower

payroll costs, equity-based incentive staff compensation and lower regulatory and professional fees incurred.

51

General and administrative expenses for the years ended December 31, 2022 and 2021 are comprised of:    

For the Year Ended December 31,

General and administrative expenses – segments
General and administrative expenses – corporate

Total general and administrative expenses

Interest and Amortization Expenses

2022

2021

($ in thousands)

$

$

11,634  $
19,313 
30,947  $

10,341 
25,679 
36,020 

The interest and amortization expenses related to outstanding senior notes issued by Maiden Holdings in 2016 and Maiden NA in 2013 were $19.3 million for
the years ended December 31, 2022 and 2021, respectively. Please refer to "Notes to Consolidated Financial Statements - Note 7 — Long-Term Debt" included
under Item 8 "Financial Statements and Supplementary Data" of this Form 10-K for further details on the Senior Notes. The weighted average effective interest
rate for the Senior Notes was 7.6% for the years ended December 31, 2022 and 2021, respectively.

Foreign Exchange and Other Gains

Net foreign exchange and other gains amounted to $8.3 million during the year ended December 31, 2022 compared to net foreign exchange and other gains of

$7.7 million in 2021.

At  December  31,  2022,  net  foreign  exchange  gains  were  primarily  driven  by  exposures  to  euro,  British  pound  and  other  non-USD  denominated  net  loss
reserves  and  insurance  related  liabilities  in  excess  of  foreign  currency  assets.  Our  non-USD  denominated  liabilities  at  December  31,  2022  included  net  loss
reserves  of  $333.9  million.  There  was  no  new  business  written  in  non-USD  currencies  during  the  year  ended  December  31,  2022.  Our  foreign  currency  asset
exposures  at  December  31,  2022  included  $205.1  million  of  fixed  maturity  securities  managed  by  our  investment  managers  who  have  the  discretion  to  hold
foreign currency exposures as part of their total return strategy as well as $20.9 million of equity method real estate investments denominated in Canadian dollars.

Net  foreign  exchange  gains  of  $8.9  million  and  $7.5  million  for  the  years  ended  December  31,  2022  and  2021,  respectively,  were  attributable  to  the

strengthening of the U.S. dollar on the re-measurement of net loss reserves and insurance related liabilities denominated in British pound and euro.

Income Tax Benefit (Expense)

The Company recognized an income tax benefit of $0.6 million for the year ended December 31, 2022 compared to an income tax expense of $15.0 thousand
recognized for 2021. The income tax expense for 2021 was largely generated on the operating losses of our international subsidiaries. The effective rate of income
tax was 0.9% for the year ended December 31, 2022 compared to an income tax rate of 0.1% for the year ended December 31, 2021. The effective tax rate on the
Company's net income differs from the statutory rate of zero percent under Bermuda law due to tax on foreign operations, primarily the U.S. and Sweden.

Underwriting Results by Reportable Segment

Diversified Reinsurance Segment

The underwriting results for our Diversified Reinsurance segment for the years ended December 31, 2022 and 2021 were as follows:

For the Year Ended December 31,

Gross premiums written
Net premiums written
Net premiums earned
Other insurance (expense) revenue
Net loss and LAE
Commission and other acquisition expenses
General and administrative expenses

Underwriting (loss) income

2022

2021

($ in thousands)

$
$
$

$

24,017  $
23,620  $
27,983  $
(4,530)
(12,483)
(14,164)
(8,857)
(12,051) $

16,633 
16,098 
27,681 
1,067 
(4,286)
(15,093)
(7,827)
1,542 

Underwriting results in the Diversified Reinsurance segment decreased for the year ended December 31, 2022 compared to 2021. This was primarily due to
results  from  GLS  operations,  which  reported  an  underwriting  loss  of  $8.9  million  for  the  year  ended  December  31,  2022  compared  to  $0.1  million  in  2021,
primarily  driven  by  a  $4.8  million  decrease  in  the  fair  value  of  underwriting-related  derivatives  due  to  the  acceleration  of  covered  payments  which  triggered
coverage in excess of the contracts risk margin during the year ended December 31, 2022.

52

Underwriting (loss) income by business unit is detailed in the table below for the Diversified Reinsurance segment for the years ended December 31, 2022 and

2021:

For the Year Ended December 31,

International
GLS
Other run-off lines

Underwriting (loss) income

2022

2021

($ in thousands)

$

$

(1,103) $
(8,923)
(2,025)
(12,051) $

261 
(137)
1,418 
1,542 

Premiums - Gross premiums written increased by $7.4 million, or 44.4% for the year ended December 31, 2022 compared to 2021 primarily due to the prior
year return of unearned premiums written in a German Auto quota share reinsurance contract in our IIS business which went into run-off on January 1, 2021.
Direct premiums written by Maiden LF and Maiden GF increased by $2.7 million or 12.3% during the year ended December 31, 2022 compared to 2021.

Net premiums written for the year ended December 31, 2022 increased by $7.5 million or 46.7% compared to 2021 due to the prior year return of unearned

premiums in our German Auto quota share reinsurance contract which went into run-off on January 1, 2021.

Net premiums earned increased by $0.3 million or 1.1% during the year ended December 31, 2022 compared to 2021.

Other Insurance (Expense) Revenue, Net - Other insurance (expense) revenue, net for the year ended December 31, 2022 includes fee income earned from
our GLS business, fair value changes in derivatives related to certain coverages on retroactive reinsurance contracts written by GLS, and fee income derived from
our IIS business not directly associated with premium revenue assumed by the Company as specified in the table below.

Total  other  insurance  (expense)  revenue,  net  decreased  by  $5.6  million  for  the  year  ended  December  31,  2022  compared  to  2021  largely  due  to  fair  value
changes on non-hedged underwriting-related derivatives in GLS. The decrease in the fair value of underwriting-related derivatives of $4.8 million was due to the
acceleration of covered payments which triggered coverage in excess of the contracts risk margin. The decline of International fee income was primarily due to an
auto customer program that went into run-off on July 31, 2021.

The table below shows other insurance (expense) revenue, net by source for the years ended December 31, 2022 and 2021:

For the Year Ended December 31,

Change in fair value of non-hedged underwriting-related derivatives
Other service fee income
International fee income

Total other insurance (expense) revenue, net

2022

2021
($ in thousands)

Change in $

$

$

(4,825) $
194 
101 
(4,530) $

—  $
302 
765 
1,067  $

(4,825)
(108)
(664)
(5,597)

Net Loss and LAE - Net loss and LAE increased by $8.2 million or 191.3% for the year ended December 31, 2022 compared to 2021. Net Loss and LAE was
impacted  by  adverse  prior  year  loss  reserve  development  of  $4.6  million  during  2022,  compared  to  the  impact  of  favorable  development  of  $3.6  million
experienced during 2021.

The  adverse  prior  year  development  in  2022  was  primarily  due  to  GLS  contracts  and  other  reinsurance  run-off  lines  partly  offset  by  favorable  reserve
development in German Auto Programs. The favorable prior year loss development in 2021 was due to German Auto Programs, the run-off of European Capital
Solutions and facultative reinsurance run-off lines.

The table below details prior year loss development by line of business for the years ended December 31, 2022 and 2021:

For the Year Ended December 31,
Prior Year Loss Development adverse (favorable)
IIS business
GLS
Other run-off lines

Total Diversified Reinsurance Prior Year Development

2022

2021

($ in thousands)

$

$

(1,683) $
1,825 
4,410 
4,552  $

(2,044)
— 
(1,517)
(3,561)

53

 
 
 
 
 
Commission  and  Other  Acquisition  Expenses  -  Commission  and  other  acquisition  expenses  decreased  by  $0.9  million  or  6.2%  for  the  year  ended
December 31, 2022 compared to 2021. The lower commission expense for the year ended December 31, 2022 was largely related to an auto customer program
that went into run-off on July 31, 2021.

General  and  Administrative  Expenses -  General  and  administrative  expenses  increased  by  $1.0  million  or  13.2%  for  the  year  ended  December  31,  2022

compared to 2021.

AmTrust Reinsurance Segment

The AmTrust Reinsurance segment reported an underwriting loss of $42.9 million for the year ended December 31, 2022 compared to underwriting income of
$10.0 million for the year ended December 31, 2021. The decrease in underwriting results for the year ended December 31, 2022 was largely driven by adverse
prior  year  loss  development  of  $28.1  million  during  the  year  ended  December  31,  2022,  which  is  detailed  herein,  compared  to  net  favorable  prior  year  loss
development of $24.0 million in 2021.

A significant portion of the loss development for the year ended December 31, 2022 was the result of the receipt of newly emergent adverse loss data for both
known and unknown claims across a series of liability lines detailed in "Net Loss and Loss Adjustment Expenses" further below, primarily on older underwriting
years reported by AmTrust. Accordingly, we have adjusted our carried IBNR and continue to be responsive and proactive to the loss data we are receiving.

The  AmTrust  Cession  Adjustments  contributed  an  underwriting  loss  of  $5.1  million  to  our  reported  results  during  the  year  ended  December  31,  2022;
excluding  these  adjustments,  the  AmTrust  Reinsurance  segment  had  an  underwriting  loss  of  $37.8  million  on  the  run-off  of  unearned  premium  for  terminated
AmTrust reinsurance contracts.

The underwriting results for the AmTrust Reinsurance segment for the years ended December 31, 2022 and 2021 were as follows:

For the Year Ended December 31,

Gross premiums written
Net premiums written
Net premiums earned
Net loss and LAE
Commission and other acquisition expenses
General and administrative expenses

Underwriting (loss) income

2022

2021

($ in thousands)

$
$
$

$

(18,538) $
(18,538) $
9,749  $

(45,508)
(4,347)
(2,777)
(42,883) $

(5,695)
(5,695)
25,312 
(3,021)
(9,747)
(2,514)
10,030 

Premiums -  The table below shows net premiums written by category for the years ended December 31, 2022 and 2021:

For the Year Ended December 31,

Net Premiums Written
Small Commercial Business
Specialty Program
Specialty Risk and Extended Warranty

Total AmTrust Reinsurance

2022

2021
($ in thousands)

Change in $

$

$

(15,143) $
747 
(4,142)
(18,538) $

(6,445) $
(876)
1,626 
(5,695) $

(8,698)
1,623 
(5,768)
(12,843)

The negative gross and net premiums written for the year ended December 31, 2022 reflect the AmTrust Cession Adjustments which consist of higher than

expected adjustments related to the following items:

•$11.0 million of premium reductions on Workers Compensation policy surcharges in Small Commercial Business subsequent to the termination of the
AmTrust Quota Share; and

•$4.8 million of premium reductions to AmTrust's inuring reinsurance for certain programs in Specialty Risk and Extended Warranty which reduced the
amount of premium ceded to Maiden.

There were also negative gross and net premiums written for the year ended December 31, 2022 and 2021 due to premium adjustments on Small Commercial
Business policies in the AmTrust Quota Share. Furthermore, the termination of the AmTrust Quota Share and the European Hospital Liability Quota Share as of
January 1, 2019 resulted in no new business written under these contracts since 2018.

54

 
Net premiums earned decreased by $15.6 million for the year ended December 31, 2022 compared to 2021 due to AmTrust Cession Adjustments and due to
the termination of the AmTrust Quota Share and European Hospital Liability Quota Share as of January 1, 2019. Excluding AmTrust Cession Adjustments of
$15.8 million, net premiums earned were $25.5 million for the year ended December 31, 2022 compared to $25.3 million in 2021. Negative premiums earned in
the years ended December 31, 2022 and 2021 in Small Commercial Business were due to premium adjustments on such policies in the AmTrust Quota Share.

The table below details net premiums earned by category for the years ended December 31, 2022 and 2021:

For the Year Ended December 31,
($ in thousands)
Net Premiums Earned
Small Commercial Business
Specialty Program
Specialty Risk and Extended Warranty

Total AmTrust Reinsurance

2022

2021

Total

% of Total

Total

% of Total

$

$

(15,131)
748 
24,132 
9,749 

(155.2)% $
7.7 %
247.5 %
100.0 % $

(6,095)
(853)
32,260 
25,312 

(24.1)%
(3.4)%
127.5 %
100.0 %

Net Loss and Loss Adjustment Expenses - Net loss and LAE increased by $42.5 million for the year ended December 31, 2022 compared to 2021 largely due
to net adverse prior year loss development of $28.1 million during the year ended December 31, 2022, compared to net favorable prior year loss development of
$24.0 million in 2021.

Net adverse prior year loss development of $28.1 million during the year ended December 31, 2022 was due to unfavorable movements in Commercial Auto
Liability,  General  Liability,  Other  Specialty  Risk  &  Extended  Warranty  and  European  Hospital  Liability  partly  offset  by  continued  favorable  development  in
Workers Compensation. European Hospital Liability was due in part to higher than expected loss emergence in Italian Hospital Liability policies as well as the
agreed exit cost of $3.7 million (€3.4 million) for the commutation of French Hospital Liability policies as described in "Note 10. Related Party Transactions".

Net favorable prior year loss development in 2021 was due to Workers Compensation and Commercial Auto Liability partly offset by adverse development in

General Liability and European Hospital Liability.

The table below details prior year loss development by lines of business for the years ended December 31, 2022 and 2021:

For the Year Ended December 31,
Prior Year Loss Development adverse (favorable) before the impact of the LPT/ADC Agreement
Workers Compensation
Commercial Auto Liability
General Liability
European Hospital Liability
Other Lines
Other Specialty Risk & Extended Warranty

Total AmTrust Reinsurance Prior Year Development

2022

2021

($ in thousands)

$

$

(38,131) $
19,088 
18,452 
13,247 
(1,685)
17,113 
28,084  $

(22,242)
(29,918)
20,868 
7,885 
(637)
— 
(24,044)

As  of  December  31,  2022,  the  reinsurance  recoverable  on  unpaid  losses  under  the  LPT/ADC  Agreement  was  $490.4  million.  The  LPT/ADC  Agreement
provides Maiden Reinsurance with $155.0 million in adverse development cover over its carried AmTrust Quota Share loss reserves at December 31, 2018. All
lines  of  business  in  the  table  above  are  covered  by  the  LPT/ADC  Agreement,  except  for  European  Hospital  Liability  which  is  not  part  of  the  AmTrust  Quota
Share. European Hospital Liability business is not covered under the LPT/ADC Agreement and therefore, adverse development in this line of business may result
in significant losses.

Commission and Other Acquisition Expenses - Commission and other acquisition expenses decreased by $5.4 million for the year ended December 31, 2022

compared to 2021 primarily due to AmTrust Cession Adjustments which resulted in negative earned premiums and a reduction to related brokerage fees.

Excluding AmTrust Cession Adjustments of $5.4 million, commission and other acquisition expenses were $9.7 million for the year ended December 31, 2022

compared to $9.7 million in 2021.

General  and  Administrative  Expenses -  General  and  administrative  expenses  increased  by  $0.3  million  or  10.5%  for  the  year  ended  December  31,  2022

compared to 2021 primarily due to higher letter of credit fees associated with the LPT/ADC Agreement.

55

Liquidity and Capital Resources

Liquidity

Maiden Holdings is a holding company and transacts no business of its own. We therefore rely on cash flows in the form of dividends, advances, loans and
other permitted distributions from our subsidiary companies to pay expenses and make dividend payments on our common shares. The jurisdictions in which our
operating subsidiaries are licensed to write business impose regulations requiring companies to maintain or meet statutory solvency and liquidity requirements and
also place restrictions on the declaration and payment of dividends and other distributions.

As  of  December  31,  2022,  the  Company  had  investable  assets  of  $1.2  billion  compared  to  $1.7  billion  as  of  December  31,  2021.  Investable  assets  are  the
combined total of our investments, cash and cash equivalents (including restricted cash), loan to a related party and funds withheld receivable. The decrease in our
investable assets is primarily the result of the cessation of active reinsurance underwriting of new prospective risks since 2019 which subsequently resulted in
negative operating cash flows to settle claim payments from the run-off of liabilities from our reinsurance portfolio in 2022.

As discussed in "Item 1. Business", Maiden Reinsurance re-domesticated from Bermuda to Vermont on March 16, 2020. We continue to be actively engaged
with  the  Vermont  DFR  regarding  Maiden  Reinsurance's  longer  term  business  plan,  including  its  investment  policy,  changes  to  which  require  prior  regulatory
approval as stipulated by Vermont law or the Vermont DFR for any active underwriting, capital management or other strategic initiatives. Maiden Reinsurance has
received all necessary approvals required to date by the Vermont DFR, including its activities via GLS and its investment policy, which includes: 1) the expansion
of approved asset classes for investment reflecting not only Maiden Reinsurance’s solvency position but the material reduction in required capital necessary to
operate its business as discussed further in Item 7. Management's Discussion and Analysis of Financial Condition and Results of Operations – Liquidity & Capital
Resources  –  Cash  and  Investments;  and  2)  the  purchase  of  affiliated  securities  as  demonstrated  in  the  recent  preference  share  tender  offers  and  the  recently
completed Exchange. The Investment Policy, as approved and as amended, maintains our established investment management and governance practices.

During  the  second  quarter  of  2022,  the  Vermont  DFR  approved  an  annual  dividend  program  to  be  paid  by  Maiden  Reinsurance  to  Maiden  NA,  with
notification  to  the  Vermont  DFR  as  dividends  are  paid.  Subsequent  to  that  approval,  Maiden  Reinsurance  has  paid  $18.8  million  in  dividends  to  Maiden  NA
during the year ended December 31, 2022.

Maiden  Reinsurance  is  regulated  by  the  Vermont  DFR  and  is  the  principal  operating  subsidiary  of  Maiden  Holdings.  At  December  31,  2022,  Maiden
Reinsurance had statutory capital and surplus of $898.1 million, exceeding the amounts required to be maintained of $107.0 million at December 31, 2022. Under
its license as an affiliated reinsurer under the captive licensing laws in the State of Vermont, Maiden Reinsurance requires the approval of the Vermont DFR for the
payment  of  any  dividends.  During  the  year  ended  December  31,  2022,  Maiden  Reinsurance  paid  dividends  of  $18.8  million  to  Maiden  NA.  During  the  years
ended December 31, 2022 and 2021, Maiden NA did not pay any dividends to Maiden Holdings during both periods.

Maiden  Holdings  has  two  Swedish  domiciled  operating  subsidiaries,  Maiden  LF  and  Maiden  GF,  which  are  both  regulated  by  the  Swedish  FSA.  At
December 31, 2022, Maiden LF and Maiden GF each had a statutory capital and surplus of $7.8 million and $8.5 million, respectively, exceeding the amounts
required to be maintained of $4.3 million and $5.6 million, respectively, at December 31, 2022. Maiden LF and Maiden GF are subject to statutory and regulatory
restrictions under the Swedish FSA that limit the maximum amount of annual dividends or distributions paid by Maiden LF and Maiden GF to Maiden Holdings.
At December 31, 2022, Maiden LF and Maiden GF are not allowed to pay dividends or distributions without the permission of the Swedish FSA. During the years
ended December 31, 2022 and 2021, Maiden LF and Maiden GF did not pay any dividends to Maiden Holdings.

Maiden  Holdings’  wholly  owned  U.K.  subsidiary,  Maiden  Global,  operates  as  a  reinsurance  services  and  holding  company.  Maiden  Global  is  subject  to
regulation  by  the  U.K.  Financial  Conduct  Authority  (the  "FCA").  At  December  31,  2022,  Maiden  Global  is  allowed  to  pay  dividends  or  distributions  not
exceeding $3.8 million. Maiden Global paid dividends of $1.1 million to Maiden Holdings during the year ended December 31, 2022, however there were no
dividends paid in 2021.

We may experience continued volatility in our results of operations which could negatively impact our financial condition and create a reduction in the amount
of  available  distribution  or  dividend  capacity  from  our  regulated  reinsurance  subsidiaries,  which  would  also  reduce  liquidity.  Further,  we  and  our  insurance
subsidiaries may need additional capital to maintain compliance with regulatory capital requirements and/or be required to post additional collateral under existing
reinsurance arrangements, which could reduce our liquidity.

Operating, investing and financing cash flows

Our sources of funds historically have consisted of premium receipts net of commissions and brokerage, investment income, net proceeds from capital raising
activities, and proceeds from sales, maturities, pay downs and redemption of investments. Cash is currently used primarily to pay loss and LAE, ceded reinsurance
premium, general and administrative expenses, and interest expense, with the remainder of cash in excess of our operating requirements made available to our
investment managers for investment in accordance with our investment policy, as well as for capital management such as repurchasing our shares.

Our business has undergone significant changes since 2018. As previously noted, we have engaged in a series of transactions that have materially reduced our
balance sheet risk and transformed our operations. As a result of these transactions, we are not engaged in any active underwriting of new prospective reinsurance
business  thus  our  net  premiums  written  will  continue  to  be  materially  lower  and  investment  income  will  become  a  significantly  larger  portion  of  our  total
revenues. We are writing new retroactive risks through GLS, however this will be smaller in relation to the run-off of our prior reinsurance business. Despite

56

the initial inflow of new business from GLS, the run-off of our prior reinsurance business has continued to cause significant negative operating cash flows as we
run off the AmTrust Reinsurance segment reserves as shown in the cash flows table below.

While the development of the GLS platform over time should further enhance our ability to pursue the asset and capital management pillars of our business

strategy, we expect the trend of negative overall cash flows to continue to reduce our asset base going forward into 2023 and beyond.

We expect to use funds from cash and investment portfolios, collected premiums on reinsurance contracts in force or being run-off, investment income and
proceeds from investment sales and redemptions to meet our expected claims payments and operational expenses. Claim payments will be principally from the
run-off  of  existing  reserves  for  losses  and  LAE.  A  significant  portion  of  those  liabilities  are  collateralized  and  claim  payments  will  be  funded  by  using  this
collateral which should provide sufficient funding to fulfill those obligations.

The Company’s management believes its current sources of liquidity are adequate to meet its cash requirements for the next twelve months as we generally
expect negative operating cash flows to be sufficiently offset by positive investing cash flows. While we continue to expect our cash flows to be sufficient to meet
our  cash  requirements  and  to  operate  our  business,  our  ability  to  execute  our  asset  and  capital  management  initiatives  are  dependent  on  maintaining  adequate
levels of unrestricted liquidity and cash flows. Our expanded asset management strategy can be impacted by both investment specific and broader financial market
conditions and may not produce the expected liquidity and cash flows these investments are designed to achieve, or the timing thereof may also be impacted by
those factors. We experienced such conditions during 2022.

At December 31, 2022 and 2021, unrestricted cash and cash equivalents and unrestricted fixed maturity investments were $64.3 million and $81.1 million,

respectively. The decrease of $16.8 million in unrestricted cash and fixed maturity investments during 2022 was primarily the result of the following key items:

• $10.0 million utilized for the 2021 Preference Share Repurchase Program,

•$47.2 million utilized for net purchases of alternative investments including equity method investments, and

•$19.1 million utilized for interest payments on the Senior Notes, partly offset by:

•excess collateral releases of $64.6 million during the year including $45.0 million of collateral released by AmTrust.

Please  see  the  related  discussion  on  cash  flows  from  investing  and  financing  activities  below.  The  table  below  summarizes  our  operating,  investing  and

financing cash flows for the years ended December 31, 2022 and 2021:

For the Year Ended December 31,

Operating activities
Investing activities
Financing activities
Effect of exchange rate changes on foreign currency cash

Total decrease in cash, cash equivalents and restricted cash

Cash Flows from Operating Activities

2022

2021

($ in thousands)

(195,928) $
188,790 
(10,983)
(1,342)
(19,463) $

(394,430)
464,064 
(138,903)
(470)
(69,739)

$

$

Cash  flows  used  in  operating  activities  for  the  year  ended  December  31,  2022  were  $195.9  million  compared  to  cash  flows  used  in  operating  activities  of
$394.4 million for the year ended December 31, 2021, a decrease of $198.5 million. The operating cash flows used in operations for the years ended December 31,
2022 and 2021 were primarily the result of claims payments for the runoff of existing reserves for terminated AmTrust Quota Share and the European Hospital
Liability Quota Share contracts as well as return of premiums due to AmTrust Cession Adjustments.

Cash Flows from Investing Activities

Cash  flows  provided  by  investing  activities  consist  of  proceeds  from  sales  and  maturities  of  investments  net  of  payments  for  investments  acquired.  Net
cash provided by investing activities was $188.8 million for the year ended December 31, 2022 compared to $464.1 million for 2021 due to proceeds from sales of
fixed  maturity  investments  which  were  made  primarily  to  settle  claim  payments  and  repurchase  the  Company's  preference  shares  during  the  years  ended
December 31, 2022 and 2021.

For the year ended December 31, 2022, the proceeds from the sales, maturities and calls exceeded the purchases of fixed maturity securities by $233.4 million
compared to net proceeds of $575.4 million during 2021. The net proceeds were partly offset by $47.2 million utilized for net purchases of alternative investments,
including equity method investments, during the year ended December 31, 2022.

Cash Flows from Financing Activities

Cash flows used in financing activities were $11.0 million for the year ended December 31, 2022 compared to $138.9 million during 2021 primarily due to the
repurchase  of  the  Company's  Preference  Shares.  The  Company  paid  $10.0  million  for  the  repurchase  of  1,581,509  preference  shares  pursuant  to  the  2021
Preference Share Repurchase Program during the year ended December 31, 2022 compared to $136.3 million paid during 2021 for 9,404,012 preference shares.
The Company also paid $1.0

57

million for common share repurchases from employees which represent tax withholding in respect of tax obligations on vesting of both non-performance-based
and discretionary performance-based restricted shares during 2022.

No dividends on common or preference shares were paid during 2022 and 2021. Our Board of Directors has not declared any common or preference share

dividends since the third quarter of 2018. After the Exchange, there are no longer any preference shares outstanding as of December 31, 2022.

Restrictions, Collateral and Specific Requirements

Maiden Reinsurance is generally required to post collateral security with respect to any reinsurance liabilities it assumes from ceding insurers domiciled in the
U.S. to obtain credit on their U.S. statutory financial statements with respect to reinsurance recoverables due to them. Consequently, cash and cash equivalents and
investments are pledged in favor of ceding companies to comply with relevant insurance regulations or contractual requirements.

At December 31, 2022, the Company had letters of credit outstanding of $40.3 million for collateral purposes which are secured by cash and fixed maturities

with a fair value of $47.1 million.

At  December  31,  2022  and  2021,  restricted  cash  and  cash  equivalents  and  fixed  maturity  investments  used  as  collateral  were  $296.8  million  and  $582.1
million,  respectively.  This  collateral  represents  82.2%  and  87.8%  of  the  fair  value  of  our  total  fixed  maturity  investments  and  cash,  restricted  cash  and  cash
equivalents  at  December  31,  2022  and  2021,  respectively.  The  following  table  provides  additional  information  on  restricted  cash  and  fixed  maturities  used  as
collateral at December 31, 2022 and 2021:

December 31,

($ in thousands)
Diversified Reinsurance
AmTrust Reinsurance

Total

Restricted Cash & 
Equivalents

2022

Fixed 
Maturities

Total

Restricted Cash & 
Equivalents

2021

Fixed 
Maturities

$

$

13,122
2,516
15,638

$

$

48,101
233,091
281,192

$

$

61,223
235,607
296,830

$

$

34,298
5,121
39,419

$

$

48,845
493,883
542,728

$

$

Total

83,143
499,004
582,147

As a % of Consolidated Balance Sheet
captions

100.0%

89.4%

89.9%

100.0%

90.9%

91.5%

Maiden Reinsurance loaned funds of $168.0 million to AmTrust at December 31, 2022 and 2021, respectively, to partially satisfy its collateral requirements
with AII. Advances under the loan are secured by promissory notes and the loan is carried at cost. On January 30, 2019, in connection with the termination of the
AmTrust  Quota  Share,  the  Company  and  AmTrust  amended  the  Loan  Agreement  between  Maiden  Reinsurance,  AmTrust  and  AII,  originally  entered  into  on
November 16, 2007, to extend the maturity date to January 1, 2025 and the parties acknowledged that due to the termination of the AmTrust Quota Share, no
further loans or advances may be made pursuant to the Loan Agreement.

On January 11, 2019, a portion of the existing trust accounts used for collateral on the AmTrust Quota Share were converted to a funds withheld arrangement.
The Company transferred $575.0 million to AmTrust as a funds withheld receivable which bears an annual interest rate of 2.1%, subject to annual adjustment. The
annual  interest  rate  was  1.8%  for  the  duration  of  2021.  At  December  31,  2022,  the  funds  withheld  balance  was  $416.8  million  compared  to  $575.0  million  at
December 31, 2021.

On January 24, 2019, Maiden Reinsurance transferred cash of €45.1 million ($51.2 million) to AIU DAC as a funds withheld receivable to serve as collateral
for the European Hospital Liability Quota Share. AIU DAC paid Maiden Reinsurance a fixed annual interest rate of 0.5% on the average daily funds withheld
balance.  Effective  July  1,  2022,  Maiden  Reinsurance  and  AIU  DAC  entered  into  an  agreement  ("Commutation  Agreement")  which  provided  for  AIU  DAC  to
assume all reserves ceded by AIU DAC to Maiden Reinsurance with respect to AIU DAC’s French Medical Malpractice exposures for underwriting years 2012
through  2018  reinsured  by  Maiden  Reinsurance  under  the  European  Hospital  Liability  Quota  Share.  In  accordance  with  the  Commutation  Agreement,  Maiden
Reinsurance paid $31,291 (€29,401) to AIU DAC, which is the sum of net ceded reserves of $27,625 (€25,956) and an agreed exit cost of $3,666 (€3,444). As a
result of the Commutation Agreement, Maiden Reinsurance reduced its exposure to AmTrust's Hospital Liability business, however, it continues to have exposure
to Italian medical malpractice liabilities under the European Hospital Liability Quota Share. For AIU DAC, the Company utilized funds withheld to satisfy its
collateral requirements which was used to settle the Commutation Agreement on September 12, 2022. Therefore, at December 31, 2022, the funds withheld under
this agreement was eliminated compared to $26.5 million held at December 31, 2021.

Collateral arrangements with ceding insurers may subject our assets to security interests or require that a portion of our assets be pledged to, or otherwise held
by, third parties. Although the investment income derived from these assets, while held in trust, accrues to our benefit, the investment of these assets is governed
by the terms of the letter of credit facilities or the investment regulations of the state or territory of domicile of the ceding insurer, which may be more restrictive
than the investment regulations applicable to the Company under U.S. law in the State of Vermont. The restrictions may result in lower investment yields on these
assets, which may adversely affect our profitability.

We  do  not  anticipate  that  restrictions  on  liquidity  resulting  from  restrictions  on  the  payments  of  dividends  by  our  subsidiary  companies  or  from  assets
committed in trust accounts or those assets used to collateralize letter of credit facilities will have a material impact on our ability to carry out our normal business
activities.

58

 
 
 
 
Cash and Investments

Historically, the investment of our funds had generally been designed to ensure safety of principal while generating current income. Accordingly, the majority

of our funds had been invested in liquid, investment-grade fixed income securities which are all designated as AFS at December 31, 2022.

As our insurance liabilities continue to run-off and the required capital to operate our business for regulatory purposes decreases, we have modified Maiden
Reinsurance’s investment policy (which has been approved by the Vermont DFR as noted) and have expanded the range of asset classes we invest in to enhance
the income and total returns our investment portfolio produces. We categorize these investments as alternative investments which include "Other Investments",
"Equity Securities", and "Equity Method Investments" on  our  consolidated  balance  sheets  as  discussed  in  "Note 2 — Significant Accounting Policies" included
under Part II Item 8 "Financial Statements and Supplementary Data" of this Annual Report on Form 10-K.

As of December 31, 2022 and 2021, our cash and investments consisted of:

At December 31,

Fixed maturities, available-for-sale, at fair value
Equity investments, at fair value
Equity method investments
Other investments
Total investments
Cash and cash equivalents
Restricted cash and cash equivalents

Total Investments and Cash (including cash equivalents)

2022

2021

($ in thousands)

$

$

314,527  $
43,621 
80,159 
148,753 
587,060 
30,986 
15,638 
633,684  $

597,145 
24,003 
83,742 
117,722 
822,612 
26,668 
39,419 
888,699 

In addition to the discussion on Cash and Cash Equivalents and Fixed Maturities that follows herein, please see "Notes to Consolidated Financial Statements -
Note 4 — Investments" included under Part II Item 8 "Financial Statements and Supplementary Data" of this Annual Report on Form 10-K for further discussion
on our AFS fixed income securities.

Under this revised investment policy, we have continued to increase the amount of alternative investments during 2022 and 2021, and we expect to continue to
increase  the  amounts  invested  therein.  Under  our  investment  policy,  alternative  investments  could  include,  but  are  not  limited  to,  privately  held  investments,
private equities, private credit lending funds, fixed-income funds, hedge funds, equity funds, real estate (including joint ventures and limited partnerships) and
other non-fixed-income investments.

For  further  details  on  our  alternative  investments,  in  addition  to  the  discussion  of  the  investments  herein,  please  see  "Notes  to  Consolidated  Financial
Statements  Note  4(b).  Other  Investments,  Equity  Securities  and  Equity  Method  Investments"  included  under  Part  II  Item  8  "Financial  Statements  and
Supplementary Data" of this Annual Report on Form 10-K.

Our investment performance is subject to a variety of risks, including risks related to general economic conditions, market volatility, interest rate fluctuations,
foreign  exchange  risk,  liquidity  risk  and  credit  and  default  risk.  Interest  rates  are  highly  sensitive  to  many  factors,  including  governmental  monetary  policies,
domestic and international economic and political conditions and other factors beyond our control. An increase in interest rates could result in significant losses,
realized  or  unrealized,  in  the  value  of  our  investment  portfolio.  A  portion  of  our  portfolio  consists  of  alternative  investments  that  subject  us  to  restrictions  on
redemption, which may limit our ability to withdraw funds for some period of time after the initial investment. The values of, and returns on, such investments
may also be more volatile.

We believe our other investments, equity securities and equity method investments portfolio provides diversification against our fixed-income investments and
an opportunity for improved risk-adjusted return, however, the returns of these investments may be more volatile and we may experience significant unrealized
gains or losses in a particular quarter or year. While we believe the returns produced by these investments will exceed our cost of capital, in particular our cost of
debt capital, it is too soon to determine if the actual returns will achieve this objective and it may be an extended period of time before that determination can be
made.

We may utilize and pay fees to various companies to provide investment advisory and/or management services related to these investments. These fees, which
would  be  predominantly  based  upon  the  amount  of  assets  under  management,  would  be  included  in  net  investment  income.  In  addition,  costs  associated  with
evaluating, analyzing and monitoring these investments may require additional expenditures than traditional marketable securities. During 2022, our investment
expenses associated with our alternative investments decreased compared to 2021.

The substantial majority of our current and future investments are held by Maiden Reinsurance, whose investment policy has been approved by the Vermont
DFR. We utilized a portion of Maiden Reinsurance's unrestricted assets to purchase affiliated securities and, during the year ended December 31, 2022, we utilized
$10.0 million in conjunction with the 2021 Preference Share Repurchase Program. Maiden Reinsurance received all necessary approvals for its investment policy.
Prior to the Exchange, we cumulatively invested $176.4 million in the preference shares of Maiden Holdings which have since been extinguished and exchanged
for 41,439,348 common shares of the Company pursuant to the Exchange.

59

 
As  a  result  of  the  Exchange,  there  are  no  preference  shares  outstanding.  The  market  value  of  our  common  shares  held  by  Maiden  Reinsurance  was  $87.4

million at December 31, 2022.

Cash & Cash Equivalents

At December 31, 2022, we consider the levels of cash and cash equivalents we are holding to be within our targeted ranges. During periods when interest rates
experience greater volatility, we have periodically maintained more cash and equivalents to better assess current market conditions and opportunities within our
defined risk appetite, and may do so in future periods.

Fixed Maturity Investments

The  average  yield  and  average  duration  of  our  fixed  maturities,  by  asset  class,  and  our  cash  and  cash  equivalents  (both  restricted  and  unrestricted)  are  as

follows:

December 31, 2022
AFS Fixed maturities
U.S. treasury bonds
U.S. agency bonds – mortgage-backed
Collateralized mortgage-backed securities
Non-U.S. government bonds
Collateralized loan obligations
Corporate bonds
Total fixed maturities
Cash and cash equivalents

Total

December 31, 2021
AFS fixed maturities
U.S. treasury bonds
U.S. agency bonds – mortgage-backed
Collateralized mortgage-backed securities
Non-U.S. government bonds
Collateralized loan obligations
Corporate bonds
Total AFS fixed maturities
Cash and cash equivalents

Total

Original or 
Amortized 
Cost

Gross 
Unrealized 
Gains

Gross 
Unrealized 
Losses

Fair 
Value

Average
(1)
yield

Average
(2)
duration

55,647  $
38,767 
7,199 
12,643 
119,120 
97,063 
330,439 
46,624 
377,063  $

($ in thousands)
1  $

— 
— 
— 
— 
— 
1 
— 

1  $

(116) $

(4,402)
(432)
(825)
(5,028)
(5,110)
(15,913)
— 
(15,913) $

55,532 
34,365 
6,767 
11,818 
114,092 
91,953 
314,527 
46,624 
361,151 

4.0 %
2.7 %
5.3 %
0.3 %
3.1 %
1.5 %
2.7 %
1.2 %

2.5 %

0.7 
4.7 
2.7 
2.8 
0.3 
2.1 
1.5 
0.0 

1.3 

Original or 
Amortized 
Cost

Gross 
Unrealized 
Gains

Gross 
Unrealized 
Losses

Fair 
Value

Average
(1)
yield

Average
(2)
duration

59,989  $
96,554 
14,972 
3,163 
183,974 
236,692 
595,344 
66,087 
661,431  $

($ in thousands)
—  $

2,429 
565 
113 
140 
10,094 
13,341 
— 
13,341  $

(110) $
(193)
— 
— 
(5,093)
(6,144)
(11,540)
— 
(11,540) $

59,879 
98,790 
15,537 
3,276 
179,021 
240,642 
597,145 
66,087 
663,232 

0.2 %
2.7 %
3.2 %
0.3 %
1.3 %
2.5 %
1.9 %
— %

1.7 %

0.9 
2.1 
3.1 
7.3 
0.3 
2.7 
1.7 
0.0 

1.5 

$

$

$

$

(1)    Average yield is calculated by dividing annualized investment income for each sub-component of fixed maturity securities and cash and cash equivalents (including amortization of premium or

discount) by amortized cost.
(2)    Average duration in years.

During the year ended December 31, 2022, the yield on the 10-year U.S. Treasury bond increased by 236 basis points to 3.88%. The 10-year U.S. Treasury rate
is the key risk-free determinant in the fair value of many of the fixed income securities in our portfolio. The U.S. Treasury yield curve experienced a material
upward shift during the year ended December 31, 2022, reflecting concerns of the U.S. Federal Reserve about ongoing inflation emanating from the combination
of: 1) the continuing strength of the U.S. economy combined with inflationary pressures, particularly in labor markets; 2) geopolitical instability in Eastern Europe
which threatened additional inflation and global economic stability; 3) the levels of fiscal stimulus administered by the U.S. federal government in recent years to
support the economy, particularly during the COVID-19 pandemic; and 4) the anticipated monetary policy responses required to collectively temper these factors.
Central banks globally have responded in similar fashion and continue to indicate additional interest rate increases are likely in 2023.

As a result of these and other factors, the movement in the market values of our fixed maturity portfolio during the year ended December 31, 2022 generated
net unrealized losses of $17.7 million which reduced our book value per common share by $0.17 during that period. Current outlooks for global monetary policy
indicate that substantial quantitative tightening by central banks in the U.S. and globally appears likely to continue. Our investment portfolios, in particular our
fixed maturity portfolio, may be adversely impacted by unfavorable market conditions caused by these measures, which could cause continued volatility in our
results of operations and negatively impact our financial condition.

60

 
 
 
 
 
 
 
 
 
 
 
 
 
 
Interest rate risk is the price sensitivity of a security to changes in interest rates. Credit spread risk is the price sensitivity of a security to changes in credit
spreads. As noted, the fair value of our fixed maturity investments will fluctuate with changes in interest rates and credit spreads. We attempt to maintain adequate
liquidity in our fixed maturity investments portfolio with a strategy designed to emphasize the preservation of our invested assets and provide sufficient liquidity
for the prompt payment of claims and contract liabilities. Because we collateralize a significant portion of our insurance liabilities, unanticipated or large increases
in  interest  rates  could  require  us  to  utilize  significant  amounts  of  unrestricted  cash  and  fixed  maturity  securities  to  provide  additional  collateral,  which  could
impact our asset and capital management strategy described herein.

We also monitor the duration and structure of our investment portfolio as discussed below. As of December 31, 2022, the aggregate hypothetical change in fair
value from an immediate 100 basis points increase in interest rates, assuming credit spreads remain constant, in our fixed maturity investments portfolio would
decrease the fair value of that portfolio by $9.1 million. Actual shifts in interest rates may not change by the same magnitude across the maturity spectrum or on an
individual security and, as a result, the impact on the fair value of our fixed maturity securities may be materially different from the resulting change in value
described above.

To limit our exposure to unexpected interest rate increases which would reduce the value of our fixed income securities and reduce our shareholders' equity, we
attempt to maintain the duration of our fixed maturity investment portfolio combined with our cash and cash equivalents, both restricted and unrestricted, within a
reasonable range of the duration of our loss reserves. At December 31, 2022 and 2021, these respective durations in years were as follows:

December 31,
Fixed maturities and cash and cash equivalents
Reserve for loss and LAE - gross of LPT/ADC Agreement reserves
Reserve for loss and LAE - net of LPT/ADC Agreement reserves

2022

2021

1.3
5.3
1.1

1.5
4.4
1.4

During the year ended December 31, 2022, the weighted average duration of our fixed maturity investment portfolio decreased by 0.2 years to 1.3 years while
the duration for reserve for loss and LAE increased by 0.9 years to 5.3 years. The differential in duration between these assets and liabilities may fluctuate over
time and, in the case of our fixed maturities, historically has been affected by factors such as market conditions, changes in asset mix and prepayment speeds in the
case of both our U.S. agency mortgage-backed bonds ("Agency MBS") and commercial mortgage-backed securities. At December 31, 2022, the duration of our
fixed maturity investment portfolio decreased compared to December 31, 2021 due to continued sales of fixed maturity investments primarily made to settle claim
payments with AmTrust.

At December 31, 2022, the duration of our loss reserves net of the LPT/ADC Agreement was slightly lower than the duration of our fixed maturity investment
portfolio at December 31, 2022 driven by the commutation of certain European Hospital Liability policies which were long-tailed in nature and were not subject to
the LPT/ADC Agreement.

To  limit  our  exposure  to  unexpected  interest  rate  increases  that  could  reduce  the  value  of  our  fixed  maturity  securities  and  our  shareholders'  equity,  the
Company holds floating rate securities whose fair values are less sensitive to changes in interest rates. At December 31, 2022 and December 31, 2021, 29.6% and
23.6%, respectively, of our fixed income investments are comprised of floating rate securities. The floating rate investment holdings at December 31, 2022 and
December 31, 2021 were as follows:

December 31,
($ in thousands)
Floating rate securities
Collateralized loan obligations
Collateralized mortgage-backed securities
Corporate bonds
Total floating rate AFS fixed maturities at fair value
Loan to related party

Total floating rate securities

Total fixed income investments at fair value 

(1)

2022

2021

Fair Value

% of Total

Fair Value

% of Total

$

$

$

114,092 
4,773 
— 
118,865 
167,975 
286,840 

970,538 

11.8 % $
0.5 %
— %
12.3 %
17.3 %
29.6 % $

174,873 
3,007 
1,145 
179,025 
167,975 
347,000 

$

1,467,619 

11.9 %
0.2 %
0.1 %
12.2 %
11.4 %
23.6 %

(1) Total fixed income investments at fair value include AFS fixed maturities, cash and restricted cash, funds withheld receivable, and loan to related party.

61

 
At  December  31,  2022,  100.0%  of  the  Company’s  U.S.  agency  bond  holdings  are  mortgage-backed.  Additional  details  on  the  Agency  MBS  holdings  at

December 31, 2022 and 2021 were as follows:

December 31,
($ in thousands)
FNMA – fixed rate
FHLMC – fixed rate
GNMA - variable rate

Total U.S. agency bonds

2022

2021

Fair Value

% of Total

Fair Value

% of Total

$

$

18,750 
13,034 
2,581 
34,365 

54.6 % $
37.9 %
7.5 %
100.0 % $

47,419 
47,758 
3,613 
98,790 

48.0 %
48.3 %
3.7 %
100.0 %

Total U.S. agency MBS comprise 10.9% of our fixed maturity investment portfolio at December 31, 2022. Given their relative size to our total investments, if
faster  prepayment  patterns  were  to  occur  over  an  extended  period  of  time,  this  could  potentially  limit  the  growth  in  our  investment  income  in  certain
circumstances or reduce the total amount of investment income we earn.

At  December  31,  2022  and  2021,  98.5%  and  97.8%,  respectively,  of  our  fixed  maturity  investments  consisted  of  investment  grade  securities.  We  define  a
security as being below investment grade if it has an S&P credit rating of BB+ or equivalent, or less. Please see "Part II, Item 8 - Notes to Consolidated Financial
Statements Note 4. Investments" for additional information on the credit rating of our fixed income portfolio.

The security holdings by sector and financial strength rating of our corporate bond holdings at December 31, 2022 and 2021 were as follows:

December 31, 2022
Corporate bonds
Basic Materials
Communications
Consumer
Energy
Financial Institutions
Industrials

Total Corporate bonds

December 31, 2021
Corporate bonds
Basic Materials
Communications
Consumer
Energy
Financial Institutions
Industrials
Technology

Total Corporate bonds

(1)    Ratings as assigned by S&P, or equivalent

AAA

A+, A, A-

BBB+, BBB, BBB-

BB+ or lower

Fair Value

% of Corporate
bonds

Ratings

(1)

— %
— %
— %
— %
1.6 %
— %
1.6 %

— %
5.7 %
6.3 %
0.9 %
20.3 %
2.3 %
35.5 %

Ratings

(1)

5.3 %
5.2 %
39.1 %
7.7 %
0.4 %
— %
57.7 %

— % $
— %
— %
— %
5.2 %
— %
5.2 % $

($ in thousands)

4,912 
10,004 
41,767 
7,860 
25,272 
2,138 
91,953 

5.3 %
10.9 %
45.4 %
8.6 %
27.5 %
2.3 %
100.0 %

AAA

A+, A, A-

BBB+, BBB, BBB-

BB+ or lower

Fair Value

% of Corporate
bonds

1.7 %
3.2 %
31.3 %
4.8 %
12.9 %
— %
— %
53.9 %

— % $
— %
2.8 %
— %
2.6 %
— %
— %
5.4 % $

($ in thousands)

9,995 
13,480 
87,753 
34,068 
84,025 
2,393 
8,928 
240,642 

4.1 %
5.6 %
36.5 %
14.2 %
34.9 %
1.0 %
3.7 %
100.0 %

— %
— %
— %
— %
0.6 %
— %
— %
0.6 %

2.4 %
2.4 %
2.4 %
9.4 %
18.8 %
1.0 %
3.7 %
40.1 %

62

The table below includes the Company’s ten largest corporate holdings at fair value and as a percentage of all fixed income securities held as at December 31,

2022, of which 100.0% are Euro denominated, with 54.7% invested in the Consumer Sector and 19.3% invested in the Financial Institutions sector:

December 31, 2022

Anheuser-Busch INBEV NV, 2.875%, Due 9/25/2024
Chubb Ina Holdings Inc., 1.55%, Due 3/15/2028
Kraft Heinz Foods Co., 1.5%, Due 5/24/2024
Glencore Finance (Europe) LTD, 1.875%, Due 9/13/2023
Santander Consumer Finance SA, 1.125%, Due 10/9/2023
Volkswagen International Finance NV, 1.125%, Due 10/2/2023
America Movil SAB DE CV, 1.5%, Due 3/10/2024
Utah Acquisition Sub Inc., 2.25%, Due 11/22/2024
Molson Coors Beverage Co., 1.25%, Due 7/15/2024
PPG Industries Inc., 0.875%, Due 11/3/2025

Total

(1)    Ratings as assigned by S&P, or equivalent

Fair Value
($ in thousands)

% of Total Fixed Income
Holdings

Rating

(1)

$

$

10,638 
6,139 
6,118 
5,299 
5,281 
5,277 
5,221 
5,165 
5,164 
4,912 
59,214 

3.4 %
1.9 %
1.9 %
1.7 %
1.7 %
1.7 %
1.7 %
1.6 %
1.6 %
1.6 %
18.8 %

BBB+
A
BBB-
BBB+
A
A-
A-
BBB-
BBB-
BBB+

At December 31, 2022 and 2021, respectively, we held the following non-U.S. dollar denominated securities:

December 31,
($ in thousands)

Non-U.S. dollar denominated collateralized loan obligations
Non-U.S. dollar denominated corporate bonds
Non-U.S. government bonds

Total non-U.S. dollar denominated securities

2022

2021

Fair Value

% of Total

Fair Value

% of Total

$

$

102,812 
90,491 
11,818 
205,121 

50.1 % $
44.1 %
5.8 %
100.0 % $

113,399 
147,740 
3,275 
264,414 

42.9 %
55.9 %
1.2 %
100.0 %

At December 31, 2022 and 2021, respectively, 100.0% of our non-U.S. dollar denominated securities above were invested in euro. The net decrease in non-
U.S.  dollar  denominated  fixed  maturities  is  largely  due  to  the  relative  depreciation  of  euro  denominated  corporate  bonds  during  the  year  ended  December  31,
2022. At December 31, 2022 and 2021, all of the Company's non-U.S. government issuers have a rating of AA- or higher by S&P.

For our non-U.S. dollar denominated corporate bonds, the following table summarizes the composition of the fair value of our fixed maturity investments by

ratings at December 31, 2022 and 2021:

(1)

Ratings  at December 31,
($ in thousands)
A+, A, A-
BBB+, BBB, BBB-
BB+ or lower

Total non-U.S. dollar denominated corporate bonds

(1)     Ratings as assigned by S&P, or equivalent

2022

2021

Fair Value

% of Total

Fair Value

% of Total

$

$

32,633 
53,094 
4,764 
90,491 

36.0 % $
58.7 %
5.3 %
100.0 % $

56,669 
78,021 
13,050 
147,740 

38.4 %
52.8 %
8.8 %
100.0 %

The Company does not employ any credit default protection against any of the fixed maturity investments held in non-U.S. dollar denominated currencies at

December 31, 2022 and 2021, respectively.

Other Investments, Equity Investments and Equity Method Investments

Our  alternative  investments  are  categorized  as  other  investments,  equity  securities  and  equity  method  investments  as  reported  on  our  consolidated  balance
sheets. These include private equity funds, private credit funds and hedge funds investments, investments in limited partnerships, as well as investments in direct
lending entities and investments in technology-oriented insurance related businesses known as insurtechs. Private equity investments consist of direct investments
in privately held entities, investments in private equity funds and private equity co-investments with sponsoring entities. Private credit investments consist of loans
and other debt securities of privately held entities or investment sponsors.

63

Our alternative investments as of December 31, 2022 and 2021 consisted of the following categories:

December 31,
($ in thousands)

2022

2021

Carrying Value

% of Total

Carrying Value

% of Total

Publicly traded equity investments in common stocks
Privately held common stocks
Privately held preferred stocks
Total equity securities

$

Hedge fund investments
Real estate investments
Other equity method investments
Total equity method investments

Private equity funds
Private credit funds
Privately held equity investments
Investment in direct lending funds (at cost)
Total other investments

386 
32,290 
10,945 
43,621 

5,376 
40,944 
33,839 
80,159 

34,278 
24,374 
34,014 
56,087 
148,753 

0.1  % $
11.9  %
4.0  %
16.0 %

2.0  %
15.0  %
12.4  %
29.4 %

12.6  %
8.9  %
12.5  %
20.6  %
54.6 %

1,174 
22,029 
800 
24,003 

32,929 
44,050 
6,763 
83,742 

23,324 
20,922 
30,500 
42,976 
117,722 

0.5  %
9.8  %
0.4  %
10.7 %

14.6  %
19.5  %
3.0  %
37.1 %

10.3  %
9.3  %
13.5  %
19.1  %
52.2 %

Total alternative investments

$

272,533 

100.0 % $

225,467 

100.0 %

Our  allocation  to  alternative  investments  increased  to  43.0%  of  our  total  cash  and  investments  as  of  December  31,  2022  compared  to  25.4%  as  of

December 31, 2021; and increased to 95.8% of our total shareholders' equity as of December 31, 2022 compared to 58.7% as of December 31, 2021.

In addition to the categories described above, we also evaluate our alternative investments by the following asset classes:

December 31,
($ in thousands)
Private Equity
Private Credit
Hedge Funds
Alternatives
Venture Capital
Real Estate

Total alternative investments

2022

2021

Carrying Value

% of Total

Carrying Value

% of Total

$

$

60,227 
51,783 
5,376 
85,866 
21,126 
48,155 
272,533 

22.1  % $
19.0  %
2.0  %
31.5  %
7.7  %
17.7  %
100.0 % $

66,290 
20,863 
32,929 
46,490 
7,344 
51,551 
225,467 

29.4  %
9.2  %
14.6  %
20.6  %
3.3  %
22.9  %
100.0 %

During  2022,  we  funded  $49.5  million  of  new  investments  largely  focused  on  income  producing  assets  reflecting  the  increase  in  interest  rates  experienced
during the year. To the extent that interest rates and risk-adjusted credit quality remains appropriate, we expect to continue to focus on investments that will take
advantage of that environment to produce current income.

For further details on these alternative investments, please see "Notes to Consolidated Financial Statements: Note 4(b) Other Investments, Equity Securities

and Equity Method Investments" included under Part II Item 8 "Financial Statements and Supplementary Data" of this Annual Report on Form 10-K.

Certain  of  the  Company's  investments  in  limited  partnerships  are  related  to  real  estate  joint  ventures  with  interests  in  multi-property  projects  with  varying
strategies  ranging  from  the  development  of  properties  to  the  ownership  of  income-producing  properties.  In  certain  of  these  joint  ventures,  the  Company  has
provided  certain  indemnities,  guarantees  and  commitments  to  certain  parties  such  that  it  may  be  required  to  make  payments  now  or  in  the  future.  For  further
details on these financial guarantees, please see "Notes to Consolidated Financial Statements: Note 11 - Commitments, Contingencies and Guarantees" included
under Part II Item 8 "Financial Statements and Supplementary Data" of this Annual Report on Form 10-K.

64

 
 
 
   
 
Investment Results

The following table summarizes our investment results for the years ended December 31, 2022 and 2021, respectively:

For the Year Ended December 31,
Net investment income
Fixed income investments
Cash and restricted cash
Other investments, including equities
Investment expenses
Total net investment income

(1)

Net realized (losses) gains:
Fixed income assets
Other investments, including equities
Total net realized (losses) gains

(1)

Net unrealized (losses) gains:
Other investments, including equities
Total net unrealized (losses) gains

Interest in (loss) income of equity method investments:
Interest in (loss) income of equity method investments
Total interest in (loss) income of equity method investments

Total investment return included in earnings (A)

Other comprehensive loss:
Unrealized losses on AFS securities and equity method investments excluding foreign exchange (B)

Total investment return = (A) + (B)

Annualized income from fixed income assets
Average aggregate fixed income assets, at cost
Annualized investment book yield

(2)

(2)

Average aggregate invested assets, at fair value
Investment return included in net earnings
Total investment return

(3)

$

$

$
$

$

$

2022

2021

($ in thousands)

$

$

$
$

$

27,055 
428 
2,987 
(400)
30,070 

(2,983)
190 
(2,793)

(2,347)
(2,347)

(205)
(205)

24,725 

(24,247)
478 

27,483 
1,226,134 

2.2 %

33,261 
(3)
1,103 
(2,348)
32,013 

9,097 
716 
9,813 

2,835 
2,835 

7,748 
7,748 

52,409 

(32,880)
19,529 

33,258 
1,794,173 

1.9 %

1,468,077 

$

1,986,000 

1.7 %
— %

2.6 %
1.0 %

1. Fixed income investments include AFS securities as well as funds withheld receivable, and loan to related party.
2. Fixed income assets include AFS portfolio, cash and restricted cash, funds withheld receivable, and loan to related party.
3. Average aggregate invested assets include all investments (AFS and alternative investments), cash and restricted cash, loan to related party and funds withheld receivable and is computed as an

average of the amounts disclosed in our quarterly U.S. GAAP consolidated financial statements.

65

The following table details total investment returns for our fixed income investments for the year ended December 31, 2022 and 2021, respectively:

(1)

Fixed Income Investments
($ in thousands)
Gross investment income
Net realized (losses) gains
Change in AOCI

 (3)

Gross investment returns

Average invested assets, at fair value 

(4)

Gross Investment Returns

Investment expenses

Net investment returns

Net Investment Returns

For the Year Ended December 31,

2022

2021

$

$

$

$
$

27,483 
(2,983)
(28,661)
(4,161)

1,219,079

(0.3)%

417 
(4,578)

$

$

$

$
$

33,258 
9,097 
(28,466)
13,889 

1,819,818

0.8 %

845 
13,044 

(0.4)%

0.7 %

Despite higher book yields on our fixed income investments, total returns on fixed income investments were negative for the year ended December 31, 2022

due to the impact of interest rates which increased during the year ended December 31, 2022 compared to 2021.

The following table details total investment returns for our alternative investments for the year ended December 31, 2022 and 2021, respectively:

For the Year Ended December 31,

2022

2021

$

$

$

$
$

2,782 
(2,157)
4,414 
5,039 

249,000

2.0 %

(17)
5,056 

$

$

$

$
$

8,851 
3,551 
(4,414)
7,988 

166,182

4.8 %

1,503 
6,485 

2.0 %

3.9 %

(2)

Alternative Investments
($ in thousands)
Gross investment income
Net realized and unrealized (losses) gains
Change in AOCI

 (3)

Gross investment returns

Average invested assets, at fair value 

(4)

Gross Investment Returns

Investment expenses

Net investment returns

Net Investment Returns

1. Fixed income investments includes AFS securities as well as cash, restricted cash, funds withheld receivable, and loan to related party.
2. Alternative investments includes other investments, equity securities, and equity method investments.
3. Change in AOCI excludes unrealized foreign exchange gains and losses.
4. Average invested assets is the average of the amounts disclosed in our quarterly U.S. GAAP consolidated financial statements.

66

 
 
 
 
 
 
The following table details total investment returns for alternative investments by asset class at December 31, 2022:

December 31, 2022

Private Equity

Private Credit

Hedge Funds

Gross investment income
Net realized and unrealized
(losses) gains
Change in AOCI

Total Investment Return

$

$

1,269

$

2,025

$

(5,053)

(1,717)
—
(448)

$

(2,487)
—
(462)

$

—
—
(5,053)

Average Investments

$63,259

$36,323

$19,153

Alternative
Assets

($ in thousands)
3,993

$

29
4,414
8,436

66,178

$

$

Venture Capital

Real Estate

Total

$

$

$

125

$

423

$

2,782

2,307
—
2,432

14,235

$

$

(289)
—
134

49,853

$

$

(2,157)
4,414
5,039

249,000

Gross Investment Returns

(0.7)%

(1.3)%

(26.4)%

12.7 %

17.1 %

0.3 %

2.0 %

Total investment returns on alternative investments were positive for the year ended December 31, 2022, however, net investment returns were lower compared
to 2021. During the year ended December 31, 2022, positive returns in our alternative and venture capital asset classes were partly offset by losses in our hedge
fund asset class as well as by modest losses in both private equity and private credit asset classes, largely due to rising interest rates and the resulting volatility in
financial markets. The hedge fund asset class reported a loss of $5.1 million which reduced gross investment returns by 2.4% during the period. Excluding our
hedge fund assets, our gross investment return would have been 4.4% for the year ended December 31, 2022.

The following table details total investment returns for alternative investments by asset class at December 31, 2021:

December 31, 2021

Private Equity

Private Credit

Hedge Funds

Gross investment income
Net realized and unrealized
(losses) gains
Change in AOCI

Total Investment Return

Average Investments

$

$

$

444

$

659

$

2,185
—
2,629

46,965

$

$

668
—
1,327

10,432

$

$

3,494

—
—
3,494

31,182

Alternative
Assets

($ in thousands)
4,254

$

275
(4,414)
115

46,756

$

$

Venture Capital

Real Estate

Total

$

$

$

— $

— $

8,851

423
—
423

5,072

$

$

—
—
— $

3,551
(4,414)
7,988

25,776

$

166,182

Gross Investment Returns

5.6 %

12.7 %

11.2 %

0.2 %

8.3 %

— %

4.8 %

For the year ended December 31, 2021, investment returns benefited from positive returns in the hedge fund and private credit asset classes largely resulting

from strong financial markets performance.

Despite  the  volatility  experienced  in  financial  markets  during  2022,  we  believe  our  alternative  investment  portfolio  remains  well  positioned  to  achieve  its

targeted longer-term returns.

Other Balance Sheet Changes

The following table summarizes the Company's other material balance sheet changes at December 31, 2022 and 2021:

December 31,
($ in thousands)
Reinsurance balances receivable, net
Deferred commission and other acquisition expenses
Funds withheld receivable
Reserve for loss and LAE
Unearned premiums
Deferred gain on retroactive reinsurance
Accrued expenses and other liabilities

2022

2021

Change
$

Change
%

$

10,707  $
24,976 
441,412 
1,131,408 
67,081 
47,708 
60,518 

19,507  $
36,703 
636,412 
1,489,373 
100,131 
48,960 
44,542 

(8,800)
(11,727)
(195,000)
(357,965)
(33,050)
(1,252)
15,976 

(45.1)%
(32.0)%
(30.6)%
(24.0)%
(33.0)%
(2.6)%
35.9 %

67

 
 
 
The Company's deferred commission and other acquisition expenses decreased by 32.0% and unearned premiums decreased by 33.0% primarily due to the
termination of the remaining business under both quota share contracts with AmTrust which have been in run-off since January 1, 2019. Reinsurance balances
receivable decreased by 45.1% primarily due to the collection of premiums receivable due from the European Hospital Liability Quota Share during the second
quarter of 2022.

Funds withheld receivable decreased by 30.6% primarily due to lower funds withheld to be utilized as collateral for AmTrust Reinsurance segment with the
commutation  of  French  Hospital  Liability  polices  under  the  European  Hospital  Liability  Quota  Share  during  the  third  quarter  of  2022  and  settlement  of
reinsurance losses payable due under the AmTrust Quota Share.

Accrued expenses and other liabilities increased by 35.9% primarily due to recognition of a derivative liability on retroactive reinsurance of $14.6 million for
GLS policies as of December 31, 2022. The Company's reserve for loss and LAE decreased by 24.0% primarily due to the settlement of prior year loss claims for
contracts under the AmTrust Quota Share.

The deferred gain on retroactive reinsurance decreased by 2.6% for the year ended December 31, 2022. Of the net adverse prior year loss development of $28.1
million  reported  in  the  AmTrust  Reinsurance  segment,  $15.5  million  of  this  development  was  subject  to  coverage  under  the  LPT/ADC  Agreement,  and  was
substantially offset by $16.0 million of favorable loss development on certain Workers Compensation losses that were commuted to AmTrust in 2019 that inure to
the benefit of Cavello as opposed to the Company under the terms of LPT/ADC Agreement.

Capital Resources

During the year ended December 31, 2022, book value per common share increased by 7.7% to $2.80 and diluted book value per common share increased by
7.7% to $2.79, compared to December 31, 2021 primarily due to net income available to Maiden common shareholders of $55.4 million partly offset by a net
decrease in AOCI of $29.0 million for the year ended December 31, 2022. Capital resources consist of funds deployed in support of our operations. The following
table shows the movement in our capital resources at December 31, 2022 and 2021:

December 31,
($ in thousands)
Preference shares
Common shares at par value
Additional paid-in capital
Accumulated other comprehensive loss
Accumulated deficit
Treasury shares, at cost
Common shareholders' equity
Total Maiden shareholders' equity
Senior Notes - principal amount

Total capital resources

2022

2021

—  $

1,492 
884,259 
(41,234)
(442,863)
(117,075)
284,579 
284,579 
262,500 
547,079  $

159,210  $
923 
768,650 
(12,215)
(498,295)
(34,016)
225,047 
384,257 
262,500 
646,757  $

Change
$
(159,210)
569 
115,609 
(29,019)
55,432 
(83,059)
59,532 
(99,678)
— 
(99,678)

$

$

Change
%

(100.0)%
61.6 %
15.0 %
237.6 %
(11.1)%
244.2 %
26.5 %
(25.9)%
— %

(15.4)%

Total capital resources decreased by $99.7 million, or 15.4% compared to December 31, 2021 primarily due to the following:

•net  decrease  in  Preference  Shares  of  $159.2  million  at  par  value  due  to  the  repurchase  and  Exchange  of  remaining  shares  during  the  year  ended
December 31, 2022;
•net increase in additional paid-in capital of $115.6 million due to $5.3 million relating to elimination of Preference Share issuance costs on remaining
shares which were repurchased and exchanged during the year; and additional paid-in capital of $107.6 million for the total common shares issued under
the Exchange, and share-based compensation of $2.7 million;
•net decrease in AOCI of $29.0 million which arose due to: (1) net unrealized losses on investment of $13.0 million due to a decrease of $17.7 million for
our fixed income investment portfolio relating to market price movements from rising interest rates in the year ended December 31, 2022, partly offset by
$4.4 million increase for equity method investments and $0.3 million increase in deferred taxes; and (2) a decrease in cumulative translation adjustments
of $16.0 million during the year ended December 31, 2022;
•accumulated deficit decreased by $55.4 million due to gains recognized on the repurchase and Exchange of Preference Shares of $115.5 million for the
year ended December 31, 2022 which increased retained earnings partly offset by a net loss of $60.0 million for the year ended December 31, 2022; and
•treasury  shares  increased  by  $83.1  million  primarily  due  to  common  shares  issued  to  Maiden  Reinsurance  under  the  Exchange  of  $82.1  million  and
shares repurchased due to tax obligations on restricted shares vesting of $1.0 million.

Please refer to "Notes to Consolidated Financial Statements - Note 6 — Shareholders' Equity" included under Item 8 "Financial Statements and Supplementary

Data" of this Annual Report on Form 10-K for a discussion of the equity instruments issued by the Company at December 31, 2022 and 2021.

68

 
Book value and diluted book value per common share at December 31, 2022 and 2021 were computed as follows:

December 31,

Ending Maiden common shareholders’ equity
Proceeds from assumed conversion of dilutive options

Numerator for diluted book value per common share calculation

Common shares outstanding
Shares issued from assumed conversion of dilutive options and restricted share units

Denominator for diluted book value per common share calculation

Book value per common share
Diluted book value per common share

Common Shares

2022

2021

($ in thousands except share and per share data)

284,579  $

4 

284,583  $

101,532,151 
499,963 
102,032,114 

225,047 
10 
225,057 

86,467,242 
494,926 
86,962,168 

2.80  $
2.79 

2.60 
2.59 

$

$

$

On February 21, 2017, the Company's Board of Directors approved the repurchase of up to $100.0 million of the Company's common shares from time to time
at market prices. During the year ended December 31, 2022, the Company did not repurchase any common shares under its share repurchase authorization as it
was precluded from repurchasing its common shares due to its failure to pay dividends on its preference shares that were previously outstanding. At December 31,
2022, the Company had a remaining authorization of $74.2 million for share repurchases.

Preference Shares

On  March  3,  2021  and  May  6,  2021,  the  Company's  Board  of  Directors  approved  the  repurchase,  including  the  repurchase  by  Maiden  Reinsurance  in
accordance with its investment guidelines, of up to $100.0 million and $50.0 million, respectively, of the Company's preference shares from time to time at market
prices  in  open  market  purchases  or  as  were  privately  negotiated.  The  authorizations  are  collectively  referred  to  as  the  "2021  Preference  Share  Repurchase
Program".

Please refer to "Notes to Consolidated Financial Statements - 'Note 6 — Shareholders' Equity" under Item 8 "Financial Statements and Supplementary Data"

of this Annual Report on Form 10-K for a summary of repurchases made of the Company's preference shares during the year ended December 31, 2022.

On December 27, 2022, the Exchange was completed with record holders of the Series A, C and D Preference Shares and three common shares was exchanged
as consideration for each of the Series A, C and D Preference Shares tendered. A total of 1,500,050 shares of Series A Preference Shares, 1,744,028 shares of
Series  C  Preference  Shares,  and  1,542,806  shares  of  Series  D  Preference  Shares  were  extinguished  upon  the  issuance  of  14,360,652  common  shares  to  non-
affiliates at a fair value of $28.4 million.

The number of the Company's Series A, C and D Preference Shares held by Maiden Reinsurance pursuant to the 2020 Tender Offer and the 2021 Preference
Share Repurchase Program was 13,813,116 at the Exchange date. Therefore, 41,439,348 common shares were issued to Maiden Reinsurance in exchange for the
preference  shares  held  which  are  reflected  as  treasury  shares  on  the  Consolidated  Balance  Sheet  and  are  not  treated  as  outstanding  shares  for  purposes  of
determining certain financial measures, both GAAP and non-GAAP, as of, and for the period ending, December 31, 2022.

As a result of the Exchange, the Preference Shares were delisted from and no longer trade on the New York Stock Exchange as of the Exchange Date. No
Preference Shares are issued or outstanding, and the Preference Shares were deregistered under the Securities Exchange Act of 1934, as amended. In addition, all
rights of the former holders related to ownership of the Preference Shares have terminated.

Please refer to "Notes to Consolidated Financial Statements - Note 6 — Shareholders' Equity" under Item 8 "Financial Statements and Supplementary Data" of

this Annual Report on Form 10-K for further information on the above transactions.

Senior Notes

There were no changes in the Company’s Senior Notes at December 31, 2022 compared to December 31, 2021 and the Company did not enter into any short-
term  borrowing  arrangements  during  the  year  ended  December  31,  2022.  Please  refer  to  "Notes  to  Consolidated  Financial  Statements  -  Note  7  —  Long-Term
Debt" included under Item 8 "Financial Statements and Supplementary Data" of this Annual Report on Form 10-K for a discussion of the Senior Notes issued by
the Company. The 2013 Senior Notes issued by Maiden NA are fully and unconditionally guaranteed by Maiden Holdings. The Senior Notes are unsecured and
unsubordinated obligations of the Company.

Maiden  Holdings  does  not  have  any  significant  operations  or  assets  other  than  our  ownership  of  the  shares  of  our  subsidiaries.  The  dividends  and  other
permitted  distributions  from  Maiden  NA  (and  its  subsidiaries)  will  be  our  sole  source  of  funds  to  meet  ongoing  cash  requirements,  including  debt  service
payments. Factors that may affect payments to holders of the 2013 Senior

69

Notes include restrictions on the payments of dividends by Maiden Reinsurance to Maiden NA which provides the sole source of income for interest payments on
the 2013 Senior Notes. During the second quarter of 2022, the Vermont DFR approved an annual dividend program to be paid by Maiden Reinsurance to Maiden
NA, with notification to the Vermont DFR as dividends are paid. Subsequent to that approval, Maiden Reinsurance paid $18.8 million in dividends to Maiden NA
during the year ended December 31, 2022.

Summarized financial information of Maiden NA and Maiden Holdings as of December 31, 2022 and for the year ended December 31, 2022 were as follows:

Total assets
Total liabilities
Amounts due from subsidiaries (not included in total assets above)
Amounts due to subsidiaries (not included in total liabilities above)
Related party loan payable (not included in total liabilities above)
Total revenue
Net loss

Maiden NA

Maiden Holdings

$

($ in thousands)
5,345  $

150,142 
68 
13,646 
— 
361 
(19,566)

8,460 
109,843 
1,924 
2,505 
270,904 
3,788 
(20,649)

The summarized financial information above has been presented on a combined basis for the issuer Maiden NA and the guarantor Maiden Holdings, excluding
all other subsidiaries. Intercompany balances and transactions between Maiden NA and Maiden Holdings, whose information is presented above on a combined
basis, have been eliminated. Any investment by Maiden NA or Maiden Holdings in subsidiaries that are not issuers or guarantors is not presented in the financial
information above. Intercompany balances with subsidiaries that are not issuers or guarantors and any related party transactions were separately disclosed above
and are not included in the total assets and total liabilities presented for Maiden NA and Maiden Holdings.

The  net  loss  for  Maiden  NA  and  Maiden  Holdings  was  largely  due  to  interest  and  amortization  expenses  on  the  Senior  Notes  as  well  as  general  and

administrative expenses. The net loss in Maiden NA was also due to income tax expense incurred.

 The ratio of Debt to Total Capital Resources at December 31, 2022 and 2021 was computed as follows:

December 31,

Senior notes - principal amount
Maiden shareholders’ equity
Total capital resources

Ratio of debt to total capital resources

Off-Balance Sheet Arrangements

$

$

2022

2021

($ in thousands)

262,500 
284,579 
547,079 

$

$

48.0 %

262,500 
384,257 
646,757 

40.6 %

Certain  of  the  Company's  investments  in  limited  partnerships  are  related  to  real  estate  joint  ventures  with  interests  in  multi-property  projects  with  varying
strategies  ranging  from  the  development  of  properties  to  the  ownership  of  income-producing  properties.  In  certain  of  these  joint  ventures,  the  Company  has
provided  certain  indemnities,  guarantees  and  commitments  to  certain  parties  such  that  it  may  be  required  to  make  payments  now  or  in  the  future  as  further
described  in  the  "Notes  to  Consolidated  Financial  Statements  -  Note  11  —  Commitments,  Contingencies  and  Guarantees  "  included  under  Item  8  "Financial
Statements and Supplementary Data" of this Annual Report on Form 10-K.

Any loss for which the Company could be liable would be contingent on the default of a loan by the real estate joint venture entity for which the Company
provided  a  financial  guarantee  to  a  lender.  While  the  Company  has  committed  to  aggregate  limits  as  to  the  amount  of  guarantees  it  will  provide  as  part  of  its
limited  partnerships,  guarantees  are  only  provided  on  an  individual  transaction  basis  and  are  subject  to  the  terms  and  conditions  of  each  transaction  mutually
agreed by the parties involved. The Company is not bound to such guarantees without its express authorization.

As discussed above, at December 31, 2022, guarantees of $42.1 million have been provided to lenders by the Company on behalf of real estate joint ventures,
however, the likelihood of the Company incurring any losses pertaining to project level financing guarantees was determined to be remote. Therefore, no liability
has been accrued under ASC 450-20.

70

 
Non-GAAP Financial Measures

As defined and described in the Key Financial Measures section, management uses certain key financial measures, some of which are non-GAAP measures, to
evaluate  the  Company's  financial  performance  and  the  overall  growth  in  value  generated  for  the  Company’s  common  shareholders.  Management  believes  that
these financial measures, which may be defined differently by other companies, explain the Company’s results to investors in a manner that allows for a more
complete understanding of the underlying trends in the Company’s business. The calculation, reconciliation to nearest GAAP measure and discussion of relevant
non-GAAP measures used by management are discussed below.

Non-GAAP operating  earnings  were  $52.1  million  for  the  year  ended  December  31,  2022,  compared  to  non-GAAP  operating  earnings  of  $60.5  million  in
2021.  The  reduction  in  the  Company's  non-GAAP  operating  results  was  largely  due  to  a  non-GAAP  underwriting  loss  of  $55.4  million  for  the  year  ended
December 31, 2022, compared to a non-GAAP underwriting loss of $17.5 million in 2021. Underwriting performance was offset by gains of $115.5 million from
the repurchase and exchange of preference shares at market values for the year ended December 31, 2022 compared to gains of $91.0 million for preference share
repurchases during 2021.

Non-GAAP operating earnings and Non-GAAP diluted operating earnings per share attributable to common shareholders

Non-GAAP operating earnings and Non-GAAP diluted operating earnings per share attributable to common shareholders can be reconciled to the nearest U.S.

GAAP financial measure as follows:

For the Year Ended December 31,

Net income available to Maiden common shareholders
Add (subtract):
Net realized and unrealized investment losses (gains)
Foreign exchange and other gains
Decrease in deferred gain on retroactive reinsurance
Interest in loss (income) of equity method investments

Non-GAAP operating earnings

Diluted earnings per share attributable to common shareholders
Add (subtract):
Net realized and unrealized investment losses (gains)
Foreign exchange and other gains
Decrease in deferred gain on retroactive reinsurance
Interest in loss (income) of equity method investments

Non-GAAP diluted operating earnings per common share attributable to common shareholders

Non-GAAP Operating ROACE

Non-GAAP Operating ROACE for the years ended December 31, 2022 and 2021 was as follows:

For the Year Ended December 31, and at December 31,

Non-GAAP operating earnings
Opening adjusted common shareholders’ equity
Ending adjusted common shareholders’ equity
Average adjusted common shareholders’ equity
Non-GAAP Operating ROACE

71

2022

2021

($ in thousands except per share data)

55,432  $

117,643 

5,140 
(8,255)
(452)
205 
52,070  $

0.63  $

0.06 
(0.09)
(0.01)
0.01 
0.60  $

(12,648)
(7,685)
(29,081)
(7,748)
60,481 

1.35 

(0.14)
(0.09)
(0.33)
(0.09)
0.70 

$

$

$

$

$

2022

2021

($ in thousands)

$

52,070 
274,990 
329,987 
302,489 

60,481 
208,447 
274,990 
241,719 

17.2 %

25.0 %

Non-GAAP Underwriting Results

The following summarizes our non-GAAP underwriting results for the years ended December 31, 2022 and 2021:

For the Year Ended December 31,

Gross premiums written
Net premiums written
Net premiums earned
Other insurance (expenses) revenue
Non-GAAP net loss and LAE
Commission and other acquisition expenses
General and administrative expenses
Non-GAAP underwriting loss

(1)

(1)

2022

2021

($ in thousands)
5,479  $
5,082  $
37,732  $
(4,530)
(58,443)
(18,511)
(11,634)
(55,386) $

10,938 
10,403 
52,993 
1,067 
(36,388)
(24,840)
(10,341)
(17,509)

$
$
$

$

(1) Non-GAAP underwriting loss and non-GAAP net loss and LAE for the years ended December 31, 2022 and 2021 are adjusted for prior year reserve development subject to the LPT/ADC Agreement.
Please see the "Key Financial Measures" section for definitions of non-GAAP underwriting loss and non-GAAP net loss and LAE.

The non-GAAP underwriting results include the impact of favorable prior year reserve development under the AmTrust Quota Share which is fully recoverable
from Cavello under the LPT/ADC Agreement to show the ultimate economic benefit to the Company. As shown in the table above, adjusted for the decrease in the
deferred gain under the LPT/ADC Agreement of $0.5 million during the year ended December 31, 2022, the non-GAAP underwriting loss was $55.4 million. This
compared to a non-GAAP underwriting loss of $17.5 million for 2021 when adjusted for the decrease in the deferred gain under the LPT/ADC Agreement of
$29.1 million during the year ended December 31, 2021. The non-GAAP underwriting loss above was driven by:

• underwriting results in the AmTrust Reinsurance segment not covered by the LPT/ADC Agreement, specifically the run-off of the AmTrust Quota Share
with losses occurring after December 31, 2018;

• adverse loss development of $13.2 million in the European Hospital Liability Quota Share, which is not covered by the LPT/ADC Agreement;

•  favorable  development  on  commuted  Workers  Compensation  losses  which  are  contractually  covered  by  the  LPT/ADC  Agreement  that  reduced  the
deferred gain liability on retroactive reinsurance for the year ended December 31, 2022; and

•  underwriting  loss  of  $12.1  million  in  the  Diversified  Reinsurance  segment  which  included  an  underwriting  loss  of  $8.9  million  from  GLS  operations
during the year ended December 31, 2022.

Non-GAAP Net Loss and LAE

Adjusted  for  the  decrease  in  the  deferred  gain  under  the  LPT/ADC  Agreement,  the  non-GAAP  net  loss  and  LAE  for  the  year  ended  December  31,  2022
increased by $0.5 million (2021 - $29.1 million) due to favorable loss experience for AmTrust reserves covered by the LPT/ADC Agreement which are ultimately
recoverable from Cavello. This adjustment is reflected in the calculation of non-GAAP Loss and LAE in the table below:

For the Year Ended December 31,

Net loss and LAE
Less: change in deferred gain on retroactive reinsurance under the LPT/ADC Agreement

Non-GAAP net loss and LAE

2022

2021

($ in thousands)

$

$

57,991  $
(452)
58,443  $

7,307 
(29,081)
36,388 

Adjusted Shareholders' Equity, Adjusted Total Capital Resources, Adjusted Book Value per Common Share and Ratio of Debt to Total Adjusted Capital Resources

The Adjusted Shareholders' Equity, Adjusted Total Capital Resources and Adjusted Book Value per Common Share at December 31, 2022 and 2021 reflect the
addition of the unamortized deferred gain under the LPT/ADC Agreement to the GAAP shareholders' equity as depicted in the computations below. The deferred
gain  under  the  LPT/ADC  Agreement  was  $45.4  million  at  December  31,  2022  compared  to  $45.9  million  at  December  31,  2021,  and  relates  to  loss  reserves
subject to that agreement that are fully recoverable from Cavello.

The decrease in the unamortized deferred gain under the LPT/ADC Agreement for the year ended December 31, 2022 is attributable to $0.5 million in loss and
LAE  recognized  as  favorable  loss  development  in  the  Company's  GAAP  income  statement  for  policies  subject  to  the  LPT/ADC  Agreement.  We  believe  the
inclusion of this unamortized deferred gain under

72

these  metrics  better  reflects  the  ultimate  economic  benefit  of  the  LPT/ADC  Agreement,  which  will  improve  the  Company's  shareholders'  equity  over  the
settlement period under the terms of the agreement.

The Adjusted Shareholders' Equity, Adjusted Total Capital Resources and Adjusted Book Value per Common Share at December 31, 2021 also reflected the LP
Investment  Adjustment  of  $4.1  million,  which  pertained  to  the  equity  accounting  related  to  the  fair  value  of  certain  hedged  liabilities  in  an  equity  method
investment held by the Company wherein the ultimate realizable value of the asset supporting the hedged liabilities was not recognized at fair value until its sale in
2022. We believe that this adjustment recognized the future realizable value and reflected the ultimate economic benefit of this investment which was sold at a
realized gain during the year ended December 31, 2022 and improved the Company's shareholders' equity over the hedged contract period of the investment.

Reconciliation of shareholders' equity to Adjusted shareholders' equity and Adjusted Total Capital Resources

The  following  table  computes  adjusted  shareholders'  equity  and  adjusted  total  capital  resources  by  recognizing  the  unamortized  deferred  gain  under  the
LPT/ADC  Agreement  at  December  31,  2022  and  2021  as  well  as  the  LP  Investment  Adjustment  for  the  realizable  value  of  an  intangible  asset  in  a  limited
partnership investment at December 31, 2021:

December 31,

($ in thousands)
Preference shares
Common shareholders' equity
Total shareholders' equity
LP Investment Adjustment
Unamortized deferred gain on LPT/ADC Agreement
Adjusted shareholders' equity
Senior Notes - principal amount

Adjusted total capital resources

2022

2021

Change

$

$

—  $

284,579 
284,579 
— 
45,408 
329,987 
262,500 
592,487  $

159,210  $
225,047 
384,257 
4,083 
45,860 
434,200 
262,500 
696,700  $

$
(159,210)
59,532 
(99,678)
(4,083)
(452)
(104,213)
— 
(104,213)

Change

%

(100.0)%
26.5 %
(25.9)%
(100.0)%
(1.0)%
(24.0)%
— %

(15.0)%

Reconciliation of Book Value per Common Share to Adjusted Book Value per Common Share

The adjusted book value per common share as reconciled for the recognition of the unamortized deferred gain under the LPT/ADC Agreement as well as the
LP Investment Adjustment for the realizable value of an intangible asset in a limited partnership investment at December 31, 2022 and 2021 was computed as
follows:

December 31,
Book value per common share
Unamortized deferred gain on LPT/ADC Agreement
LP Investment Adjustment

Adjusted book value per common share

Ratio of Debt to Adjusted Total Capital Resources

2022

2021

$

$

2.80  $
0.45 
— 
3.25  $

2.60 
0.53 
0.05 
3.18 

 Management uses this non-GAAP measure to monitor the financial leverage of the Company. This measure is calculated using the total principal amount of
debt divided by the sum of adjusted total capital resources as computed in the table above. The ratio of Debt to Adjusted Total Capital Resources at December 31,
2022 and 2021 was computed as follows:

December 31,

Senior notes - principal amount
Adjusted shareholders’ equity

Adjusted total capital resources
Ratio of debt to adjusted total capital resources

$

$

2022

2021

($ in thousands)

262,500 
329,987 
592,487 

$

$

44.3 %

262,500 
434,200 
696,700 

37.7 %

73

 
Currency and Foreign Exchange

We  conduct  business  in  a  variety  of  foreign  (non-U.S.)  currencies,  the  principal  exposures  being  the  euro  and  the  British  pound.  Assets  and  liabilities
denominated in foreign currencies are exposed to changes in currency exchange rates. Our reporting currency is the U.S. dollar, and exchange rate fluctuations
relative to the U.S. dollar may materially impact our results and financial position. Our principal exposure to foreign currency risk is our obligation to settle claims
in  foreign  currencies.  In  addition,  to  minimize  this  risk,  we  maintain  and  expect  to  continue  to  maintain  a  portion  of  our  investment  portfolio  in  investments
denominated in currencies other than the U.S. dollar. We may employ various strategies (including hedging) to manage our exposure to foreign currency exchange
risk.  To  the  extent  that  these  exposures  are  not  fully  hedged  or  the  hedges  are  ineffective,  our  results  of  operations  or  equity  may  be  adversely  effected.  At
December  31,  2022,  no  such  hedges  or  hedging  strategies  were  in  force  or  had  been  entered  into.  We  measure  monetary  assets  and  liabilities  denominated  in
foreign  currencies  at  period  end  exchange  rates,  with  the  resulting  foreign  exchange  gains  and  losses  recognized  in  the  Consolidated  Statements  of  Income.
Revenues  and  expenses  in  foreign  currencies  are  converted  at  quarterly  average  exchange  rates  during  the  year.  The  effect  of  the  translation  adjustments  for
foreign operations is included in AOCI.

Net foreign exchange gains were $8.9 million during the year ended December 31, 2022 compared to net foreign exchange gains of $7.5 million during the

year ended December 31, 2021.

At  December  31,  2022,  net  foreign  exchange  gains  were  primarily  driven  by  exposures  to  euro,  British  pound  and  other  non-USD  denominated  net  loss
reserves and insurance related liabilities in excess of foreign currency assets. Our non-USD denominated liabilities at December 31, 2022 included reserves for net
loss and LAE of $333.9 million. There was no new business written in non-USD currencies during the year ended December 31, 2022. Our foreign currency asset
exposures at December 31, 2022 include $205.1 million of fixed maturity securities managed by our investment managers who have the discretion to hold foreign
currency exposures as part of their total return strategy as well as $20.9 million of equity method real estate investments denominated in Canadian dollars.

Effects of Inflation

The anticipated effects of inflation are considered explicitly in the pricing of the insured exposures, which are used as the initial estimates of reserves for loss
and LAE. In addition, inflation is also implicitly accounted for in subsequent estimates of loss and LAE reserves, as the expected rate of emergence is in part
predicated upon the historical levels of inflation that impact ultimate claim costs. To the extent inflation causes these costs, particularly medical treatments and
litigation costs, to vary from the assumptions made in the pricing or reserving estimates, the Company will be required to change the reserve for loss and LAE
with  a  corresponding  change  in  its  earnings  in  the  period  in  which  the  variance  is  identified.  The  actual  effects  of  inflation  on  the  results  of  operations  of  the
Company cannot be accurately known until claims are ultimately settled.

We continue to monitor inflationary impacts resulting from recent government stimulus, sharp increases in demand, labor force and supply chain disruptions,
among  other  factors,  on  our  loss  cost  trends.  Our  reserves  predominantly  consist  of  workers’  compensation,  general  liability,  and  hospital  liability.  These long
tailed lines of business have been subject to the longer term trend of social inflation, but we have not observed significant impacts for the recently elevated levels
of inflation. We proactively analyze available data and we incorporate trends into our loss reserving assumptions to ensure we are considerate of current and future
economic conditions.

Governmental policy responses to inflation have significantly increased interest rates which, in the short term, have contributed to unrealized losses on our
fixed income investments, particularly on our fixed maturity securities. There remains uncertainty around the rate and direction of inflation and we continue to
monitor our liquidity, capital and potential earnings impact of these changes but remain focused on our asset allocation decisions as described in our "Business
Strategy" section of Item 7 "Management’s Discussion and Analysis of Financial Condition and Results of Operations - Overview".

Inflation may also result in increased wage pressures for our operating expenses, as we remain focused on being a competitive employer in our market. Labor
shortages arising from the conditions of the COVID-19 pandemic have contributed to uncertainty in attracting and retaining talent that may put pressure on higher
wage costs. Currently, salaries and incentive compensation costs comprise more than one-half of our total general and administrative expenses and thereby could
have a material impact our net operating results.

Recent Accounting Pronouncements

Refer to "Notes to Consolidated Financial Statements - Note 2. Significant Accounting Policies" included under Item 8 "Financial Statement and Supplementary

Data", of this Annual Report on Form 10-K for a discussion on recently issued accounting pronouncements not yet adopted.

74

Item 8. Financial Statements and Supplementary Data.

See our Consolidated Financial Statements and Notes thereto commencing on pages F-1 through F-60 below.

Item 9. Changes in and Disagreements with Accountants on Accounting and Financial Disclosure.

None.

75

Item 9A. Controls and Procedures.

Evaluation of Disclosure Controls and Procedures

In connection with the preparation of this Report, our management has performed an evaluation, with the participation of our Principal Executive Officer and
Principal Financial Officer, of the effectiveness of our disclosure controls and procedures (as defined in Rule 13a-15(e) and 15d-15(e) under the Exchange Act) at
December  31,  2022.  Based  on  their  evaluation,  our  Principal  Executive  Officer  and  Principal  Financial  Officer  concluded  that,  at  December  31,  2022,  our
Company’s disclosure controls and procedures were effective.

Management’s Annual Report on Internal Control over Financial Reporting

Our management is responsible for establishing and maintaining adequate internal control over financial reporting as defined in Rules 13a-15(f) and 15d-15(f)
under  the  Exchange  Act  and  for  the  assessment  of  the  effectiveness  of  internal  control  over  financial  reporting.  As  defined  by  the  SEC,  internal  control  over
financial  reporting  is  a  process  designed  by,  or  under  the  supervision  of,  our  principal  executive  and  principal  financial  officers  and  effected  by  our  Board  of
Directors, management and other personnel, to provide reasonable assurance regarding the reliability of financial reporting and the preparation of the consolidated
financial statements in accordance with U.S. GAAP.

Our internal control over financial reporting includes those policies and procedures that (1) pertain to the maintenance of records that, in reasonable detail,
accurately and fairly reflect our transactions and dispositions of our assets; (2) provide reasonable assurance that transactions are recorded as necessary to permit
preparation of the consolidated financial statements in accordance with U.S. GAAP, and that our receipts and expenditures are being made only in accordance with
authorizations of our management and directors; and (3) provide reasonable assurance regarding prevention or timely detection of unauthorized acquisition, use or
disposition of our assets that could have a material effect on the consolidated financial statements.

Because of its inherent limitations, internal control over financial reporting may not prevent or detect misstatements. Also, projections of any evaluation of
effectiveness to future periods are subject to the risk that controls may become inadequate because of changes in conditions, or that the degree of compliance with
the policies or procedures may deteriorate.

In  connection  with  the  preparation  of  our  annual  consolidated  financial  statements,  management  has  undertaken  an  assessment  of  the  effectiveness  of  our
internal  control  over  financial  reporting  as  of  December  31,  2022  based  on  criteria  established  in  Internal  Control  —  Integrated  Framework  issued  by  the
Committee of Sponsoring Organizations of the Treadway Commission ("COSO") 2013. Management’s assessment included an evaluation of the design of our
internal  control  over  financial  reporting  and  testing  of  the  operational  effectiveness  of  those  controls.  Based  on  this  evaluation,  management,  including  our
Principal Executive Officer and Principal Financial Officer, have concluded that our internal control over financial reporting is effective as of December 31, 2022
based on those criteria.

The Company's independent auditors have issued an audit opinion on the Company's internal control over financial reporting as of December 31, 2022. This

report appears below in the Report of Independent Registered Public Accounting Firm.

Changes in Internal Control Over Financial Reporting

No changes were made in our internal controls over financial reporting, as such term is defined in Exchange Act Rules 13a-15(f) and 15(d) – 15(f), during the

fourth quarter ended December 31, 2022 that have materially affected, or are reasonably likely to materially affect, our internal control over financial reporting.

76

Report of Independent Registered Public Accounting Firm

To the Shareholders and Board of Directors of Maiden Holdings, Ltd.

Opinion on Internal Control Over Financial Reporting

We have audited Maiden Holdings, Ltd.’s internal control over financial reporting as of December 31, 2022, based on criteria established in Internal Control—
Integrated Framework issued by the Committee of Sponsoring Organizations of the Treadway Commission (2013 framework) (the COSO criteria). In our opinion,
Maiden Holdings, Ltd. (the Company) maintained, in all material respects, effective internal control over financial reporting as of December 31, 2022, based on
the COSO criteria.

We  also  have  audited,  in  accordance  with  the  standards  of  the  Public  Company  Accounting  Oversight  Board  (United  States)  (PCAOB),  the  consolidated
balance  sheets  of  the  Company  as  of  December  31,  2022  and  2021  and  the  related  consolidated  statements  of  income,  comprehensive  income,  changes  in
shareholders’ equity and cash flows for each of the years then ended, and the related notes and our report dated March 15, 2023 expressed an unqualified opinion
thereon.

Basis for Opinion

The  Company’s  management  is  responsible  for  maintaining  effective  internal  control  over  financial  reporting  and  for  its  assessment  of  the  effectiveness  of
internal  control  over  financial  reporting  included  in  the  accompanying  “Management’s  Annual  Report  on  Internal  Control  over  Financial  Reporting”.  Our
responsibility is to express an opinion on the Company’s internal control over financial reporting based on our audit. We are a public accounting firm registered
with the PCAOB and are required to be independent with respect to the Company in accordance with the U.S. federal securities laws and the applicable rules and
regulations of the Securities and Exchange Commission and the PCAOB.

We  conducted  our  audit  in  accordance  with  the  standards  of  the  PCAOB.  Those  standards  require  that  we  plan  and  perform  the  audit  to  obtain  reasonable

assurance about whether effective internal control over financial reporting was maintained in all material respects.

Our  audit  included  obtaining  an  understanding  of  internal  control  over  financial  reporting,  assessing  the  risk  that  a  material  weakness  exists,  testing  and
evaluating the design and operating effectiveness of internal control based on the assessed risk, and performing such other procedures as we considered necessary
in the circumstances. We believe that our audit provides a reasonable basis for our opinion.

Definition and Limitations of Internal Control Over Financial Reporting

A company’s internal control over financial reporting is a process designed to provide reasonable assurance regarding the reliability of financial reporting and
the  preparation  of  financial  statements  for  external  purposes  in  accordance  with  generally  accepted  accounting  principles.  A  company’s  internal  control  over
financial reporting includes those policies and procedures that (1) pertain to the maintenance of records that, in reasonable detail, accurately and fairly reflect the
transactions and dispositions of the assets of the company; (2) provide reasonable assurance that transactions are recorded as necessary to permit preparation of
financial  statements  in  accordance  with  generally  accepted  accounting  principles,  and  that  receipts  and  expenditures  of  the  company  are  being  made  only  in
accordance with authorizations of management and directors of the company; and (3) provide reasonable assurance regarding prevention or timely detection of
unauthorized acquisition, use, or disposition of the company’s assets that could have a material effect on the financial statements.

Because of its inherent limitations, internal control over financial reporting may not prevent or detect misstatements. Also, projections of any evaluation of
effectiveness to future periods are subject to the risk that controls may become inadequate because of changes in conditions, or that the degree of compliance with
the policies or procedures may deteriorate.

/s/ Ernst & Young LLP

New York, NY
March 15, 2023

77

Item 9B. Other Information.

None.

PART III

Item 10. Directors, Executive Officers and Corporate Governance.

The  information  required  by  this  item  is  incorporated  by  reference  from  the  information  responsive  thereto  in  the  sections  in  the  Proxy  Statement  for  our
Annual Meeting of Shareholders to be held on May 3, 2023 (the "Proxy Statement") captioned "Election of Directors", "Executive Officers", "Audit Committee",
"Section 16(a) Beneficial Ownership Reporting Compliance" and "Nominating and Corporate Governance Committee".

We  have  adopted  a  Code  of  Business  Conduct  and  Ethics  for  all  employees.  The  Code  of  Business  Conduct  and  Ethics  is  available  free  of  charge  on  our
website  at  www.maiden.bm  and  is  available  in  print  to  any  shareholder  who  requests  it.  We  intend  to  disclose  any  amendments  to  this  code  by  posting  such
information on our website, and disclose any waivers of this code applicable to our principal executive officer, principal financial officer, principal accounting
officer or controller and other executive officers who perform similar functions through such means or by filing a Form 8-K.

Item 11. Executive Compensation.

The information required by this item is incorporated by reference from the information responsive thereto in the sections in the Proxy Statement captioned
"Compensation Discussion and Analysis", "Director Compensation for 2022", "Compensation Committee Interlocks and Insider Participation" and "Compensation
Committee Report".

Item 12. Security Ownership of Certain Beneficial Owners and Management and Related Stockholder Matters.

The information required by this item is incorporated by reference from the information responsive thereto in the sections in the Proxy Statement captioned

"Security Ownership of Certain Beneficial Owners", "Equity Compensation Plan Information" and "Security Ownership of Management".

Item 13. Certain Relationships and Related Transactions, and Director Independence.

The information required by this item is incorporated by reference from the information responsive thereto in the sections in the Proxy Statement captioned
"Certain  Relationships  and  Related  Transactions",  "Audit  Committee",  "Board  Independence",  "Compensation  Committee"  and  "Nominating  and  Corporate
Governance Committee".

Item 14. Principal Accounting Fees and Services.

The information required by this item is incorporated by reference from the information responsive thereto in the section in the Proxy Statement captioned

"Appointment of Independent Auditors of Maiden Holdings, Ltd.".

Item 15. Exhibits, Financial Statement Schedules.

(a) Financial statements and schedules

PART IV

Financial statements listed in the accompanying index to our Consolidated Financial Statements starting on page F-1 are filed as part of this Annual Report on

Form 10-K, and are included in Item 8. "Financial Statement and Supplementary Data".

All other schedules for which provision is made in the applicable regulation of the Securities and Exchange Commission are not required under the related

instructions or are inapplicable, and therefore have been omitted.

(b) Exhibits

The exhibits listed in the Exhibit Index starting on page E-1 following the signature page are filed herewith, which Exhibit Index is incorporated herein by

reference.

Item 16. Form 10-K Summary.

None.

78

Pursuant to the requirements of Section 13 or 15(d) of the Securities Exchange Act of 1934, the registrant has duly caused this Report to be signed on its

behalf by the undersigned, thereunto duly authorized, in Pembroke, Bermuda on March 15, 2023.

SIGNATURES

MAIDEN HOLDINGS, LTD.
By:

/s/ Lawrence F. Metz
Name: Lawrence F. Metz
Title: President and Co-Chief Executive Officer

/s/ Patrick J. Haveron
Name: Patrick J. Haveron
Title: Co-Chief Executive Officer and Chief Financial Officer

Pursuant to the requirements of the Securities Exchange Act of 1934, this report has been signed below by the following persons on behalf of the registrant

and in the capacities and on the dates indicated.

Signature

/s/ Lawrence F. Metz
Lawrence F. Metz
/s/ Patrick J. Haveron
Patrick J. Haveron
/s/ Barry D. Zyskind
Barry D. Zyskind
/s/ Steven H. Nigro
Steven H. Nigro
/s/ Holly L. Blanchard
Holly L. Blanchard
/s/ Simcha G. Lyons
Simcha G. Lyons
/s/ Raymond M. Neff
Raymond M. Neff
/s/ Yehuda L. Neuberger
Yehuda L. Neuberger
/s/ Keith A. Thomas
Keith A. Thomas

Title

Date

President and Co-Chief Executive Officer
(Principal Executive Officer)
Co-Chief Executive Officer and Chief Financial Officer
(Principal Financial Officer)
Chairman

Vice Chairman and Lead Independent Director

Director

Director

Director

Director

Director

79

March 15, 2023

March 15, 2023

March 15, 2023

March 15, 2023

March 15, 2023

March 15, 2023

March 15, 2023

March 15, 2023

March 15, 2023

 
EXHIBIT INDEX

Description

Memorandum of Association (as amended)
Bye-Laws
Form of Common Share Certificate
Form  of  Indenture  for  Debt  Securities  by  and  among  Maiden  Holdings  North  America,  Ltd.,  Maiden  Holdings,  Ltd.,  as
guarantor, and Wilmington Trust Company, as trustee
Third  Supplemental  Indenture,  dated  November  25,  2013,  by  and  among  Maiden  Holdings  North  America,  Ltd.,  Maiden
Holdings, Ltd., as guarantor, and Wilmington Trust Company, as trustee
Form of 7.75% Notes due 2043 (included in Exhibit 4.3)
Form of Indenture for Debt Securities by and between Maiden Holdings, Ltd., and Wilmington Trust National Association, as
trustee
First Supplemental Indenture, dated as of June 14, 2016, by and between Maiden Holdings, Ltd., as guarantor, and Wilmington
Trust National Association, as trustee
Form of 6.625% Notes due 2046 (included in Exhibit 4.6)
Description of the Registrant's Securities Registered Pursuant to Section 12 of the Securities Exchange Act of 1934
2019 Omnibus Incentive Plan as of December 10, 2019
Form of Share Option Agreement under 2019 Omnibus Incentive Plan
Form of Restricted Share under 2019 Omnibus Incentive Plan
Form of Employment Agreement by and between Maiden and Patrick J. Haveron and Lawrence F. Metz, dated as of November
1, 2011
Master Agreement by and between Maiden Holdings, Ltd. and AmTrust Financial Services, Inc., dated as of July 3, 2007
Amendment No. 1 to the Master Agreement by and between Maiden Holdings, Ltd. and AmTrust Financial Services, Inc., dated
as of September 17, 2007
Amendment No. 2 to the Master Agreement by and between Maiden Holdings, Ltd. and AmTrust Financial Services, Inc., dated
as of January 30, 2019
Amended  and  Restated  Quota  Share  Reinsurance  Agreement  by  and  between  Maiden  Insurance  Company  Ltd.  and  AmTrust
International Insurance, Ltd. and dated as of June 1, 2008
Loan  Agreement  by  and  between  AmTrust  International  Insurance,  Ltd.  and  Maiden  Insurance  Company  Ltd.,  dated  as  of
November 16, 2007
Amendment  No.  1  to  the  Loan  Agreement  by  and  between  AmTrust  International  Insurance,  Ltd.  and  Maiden  Insurance
Company Ltd., dated as of February 15, 2008
Amendment No. 2 to the Loan Agreement by and between Maiden Reinsurance Ltd. and AmTrust Financial Services, Inc., dated
as of December 18, 2017
2019 Amendment to the Loan Agreement by and between AmTrust International Insurance, Ltd. and Maiden Reinsurance Ltd.,
dated as of January 30, 2019.
Asset Management Agreement by and between AII Insurance Management Limited and Maiden Reinsurance Ltd. dated as of
January 1, 2018
Novation  Agreement  between  AII  Insurance  Management  Limited,  AmTrust  Financial  Services,  Inc  and  Maiden  Reinsurance
Ltd. dated as of September 9, 2020
Asset Management Agreement by and between AII Insurance Management Limited and Maiden Life Forsakrings, AB dated as
of January 1, 2018

Novation Agreement between AII Insurance Management Limited, AmTrust Financial Services, Inc. and Maiden Life
Forsakrings, AB dated as of September 9, 2020

Exhibit 
No.
3.1
3.2
4.1

4.2

4.3

4.4

4.5

4.6

4.7
4.8
10.1*
10.2*
10.3*

10.4*

10.5

10.6

10.7

10.8

10.9

10.10

10.11

10.12

10.13

10.14

10.15

10.16

Reference
(1)
(2)
(3)

(4)

(5)

(5)

(6)

(6)

(6)
(7)
(8)
(7)
(7)

(9)

(3)

(3)

(10)

(11)

(12)

(12)

(13)

(10)

(13)

(13)

(13)

(13)

E-1

 
10.17

10.18

10.19

10.20

10.21

10.22

10.23

10.24

10.25

10.26

10.27

10.28

10.29

10.30

10.31

10.32

10.33

10.34

10.35

10.36

Asset Management Agreement by and between AII Insurance Management Limited and Maiden General Forsakrings, AB dated
as of January 1, 2018

Novation Agreement between AII Insurance Management Limited, AmTrust Financial Services, Inc. and Maiden General
Forsakrings, AB dated as of September 9, 2020

Endorsement  No.  1  to  the  Amended  and  Restated  Quota  Share  Reinsurance  Agreement  by  and  between  Maiden  Insurance
Company Ltd. and AmTrust International Insurance, Ltd. dated as of July 26, 2011
Endorsement  No.  2  to  the  Quota  Share  Reinsurance  Contract  by  and  between  Maiden  Insurance  Company  Ltd.  and  AmTrust
International Insurance, Ltd. dated as of March 7, 2013
Endorsement No. 3 to the Amended and Restated Quota Share Agreement between AmTrust International Insurance, Ltd. and
Maiden Reinsurance Ltd. dated as of September 30, 2015
Endorsement No 4. to the Amended and Restated Quota Share Reinsurance Contract by and between Maiden Reinsurance Ltd.
and AmTrust International Insurance, Ltd. dated as of August 8, 2018
Endorsement No. 5 to the Amended and Restated Quota Share Reinsurance Contract by and between Maiden Reinsurance Ltd.
and AmTrust International Insurance, Ltd. dated as of November 6, 2018.
Quota  Share  Reinsurance  Contract  by  and  between  Maiden  Insurance  Company  Ltd.  and  AmTrust  Europe  Limited  and/or
AmTrust International Underwriters Limited dated as of April 1, 2011
Endorsement  No.  1  to  the  Quota  Share  Reinsurance  Contract  by  and  between  Maiden  Insurance  Company  Ltd.  and  AmTrust
Europe Limited and/or AmTrust International Underwriters Limited dated as of July 26, 2011
Endorsement  No.  2  to  the  Quota  Share  Reinsurance  Contract  by  and  between  Maiden  Insurance  Company  Ltd.  and  AmTrust
Europe Limited and/or AmTrust International Underwriters Limited dated as of August 7, 2012
Endorsement No. 3 to the Amended and Restated Quota Share Reinsurance Agreement by and between Maiden Reinsurance Ltd.
and AmTrust International Insurance, Ltd. dated as of March 1, 2015
Endorsement  No.  4  to  the  Quota  Share  Reinsurance  Contract  by  and  between  Maiden  Reinsurance  Ltd.  and  AmTrust  Europe
Limited and/or AmTrust International Underwriters Limited dated as of July 1, 2016
Form of Indemnification Agreement between Maiden Holdings, Ltd. and its officers and directors
Partial  Termination  Endorsement  to  the  Amended  and  Restated  Quota  Share  Reinsurance  Agreement  by  and  between  Maiden
Reinsurance Ltd. and AmTrust International Insurance, Ltd. dated January 1, 2019
Termination  Endorsement  to  the  Amended  and  Restated  Quota  Share  Reinsurance  Agreement  by  and  between  Maiden
Reinsurance Ltd. and AmTrust International Insurance, Ltd. dated January 30, 2019

Termination Endorsement to the Quota Share Reinsurance Contract by and between Maiden Reinsurance Ltd. and AmTrust
Europe Limited and AmTrust International Underwriters DAC dated January 30, 2019

Master Agreement by and among Maiden Holdings, Ltd., Maiden Reinsurance Ltd. and Enstar Group Limited dated as of March
1, 2019
Adverse Development Cover Agreement by and between Maiden Reinsurance Ltd. and Cavello Bay Reinsurance Limited, dated
July 31, 2019
Commutation Agreement and Release between Maiden Reinsurance Ltd. and AmTrust International Insurance, dated July 31,
2019
Master Collateral Agreement between Maiden Reinsurance Ltd., Cavello Bay Reinsurance Limited, AmTrust Financial Services,
Inc., AmTrust International Insurance, Ltd. and Technology Insurance Company, Inc., dated July 31, 2019

(13)

(13)

(14)

(15)

(16)

(17)

(18)

(14)

(14)

(19)

(20)

(21)

(22)

(23)

(10)

(10)

(24)

(25)

(25)

(25)

E-2

10.37

10.38

10.39

10.40

10.41

14.1
21.1
22.1
23.1
31.1
31.2
32.1
32.2

101.1

Post-Termination Endorsement No. 1 between Maiden Reinsurance Ltd. and AmTrust International Insurance, Ltd. to the
Amended and Restated Quota Share Reinsurance Agreement, dated July 31, 2019
Post-Termination Endorsement No. 1 between Maiden Reinsurance Ltd. and AmTrust Europe Limited and AmTrust International
Underwriters DAC to the Quota Share Reinsurance Contract, dated January 13, 2020
Post-Termination  Endorsement  No.  2  between  Maiden  Reinsurance  Ltd.  and  AmTrust  International  Insurance,  Ltd  to  the
Amended and Restated Quota Share Reinsurance Agreement, dated January 13, 2020
Post-Termination Endorsement No. 2 between Maiden Reinsurance Ltd. and AmTrust Europe Limited and AmTrust International
Underwriters DAC to the Quota Share Reinsurance Contract, dated May 12, 2020
Commutation  Agreement  and  Release  by  and  between  AmTrust  International  Insurance,  Ltd.  and  Maiden  Reinsurance  Ltd.,
dated May 20, 2020
Code of Business Conduct and Ethics
Subsidiaries of the registrant
List of subsidiary issuers of parent guaranteed securities
Consent of Ernst & Young LLP
Section 302 Certification of CEO
Section 302 Certification of CFO
Section 906 Certification of CEO
Section 906 Certification of CFO
The  following  financial  information  from  Maiden  Holdings,  Ltd.'s  Annual  Report  on  Form  10-K  for  the  year  ended  December  31,  2022,
formatted in XBRL (eXtensive Business Reporting Language): (i) the Consolidated Balance Sheets at December 31, 2022 and 2021; (ii) the
Consolidated  Statements  of  Income  for  the  years  ended  December  31,  2022  and  2021;  (iii)  the  Consolidated  Statements  of  Comprehensive
Income for the years ended December 31, 2022 and 2021; (iv) the Consolidated Statements of Changes in Shareholders' Equity for the years
ended December 31, 2022 and 2021; (v) the Consolidated Statements of Cash Flows for the years ended December 31, 2022 and 2021; and (vi)
Notes to Consolidated Financial Statements.

(25)

(8)

(8)

(13)

(13)

(13)
 †
†
†
 †
 †
 †
 †

 †

1.

2.

3.

4.

5.
6.
7.

8.
9.

10.
11.

12.

Incorporated by reference to the filing of such exhibit with the registrant's Registration Statement on Form S-8 filed with the SEC on May 18, 2010 (File No. 333-166934).

Incorporated by reference to the filing of such exhibit with the registrant's Registration Statement on S-8 initially filed with the SEC on January 17, 2020 (File No. 333-
235948).
Incorporated by reference to the filing of such exhibit with the registrant's Registration Statement on S-1 initially filed with the SEC on September 17, 2007, subsequently
amended and declared effective May 6, 2008 (File No. 333-146137).
Incorporated by reference to the filing of such exhibit with the registrant's Registration Statement on S-3 filed with the SEC on February 7, 2011 (File Nos. 333-172107
and 333-172107-01).
Incorporated by reference to the filing of such exhibit with the registrant's Current Report on Form 8-K filed with the SEC on November 25, 2013 (File No. 001-34042).
Incorporated by reference to the filing of such exhibit with the registrant’s Current Report on Form 8-K filed with the SEC on June 14, 2016 (File No. 001-34042).
Incorporated by reference to the filing of such exhibit with the registrant's Annual Report on Form 10-K for the fiscal year ended December 31, 2019 filed with the SEC
on March 18, 2020 (File No. 001-34042).
Incorporated by reference to the filing of such exhibit with the registrant's Proxy Statement on Schedule 14A filed with the SEC on November 8, 2019.
Incorporated by reference to the filing of such exhibit with the registrant's Annual Report on Form 10-K for the fiscal year ended December 31, 2011 filed with the SEC
on March 13, 2012 (File No. 001-34042).
Incorporated by reference to the filing of such exhibit with the registrant’s Current Report on Form 8-K filed with the SEC on January 30, 2019 (File No. 001-34042).
Incorporated by reference to the filing of such exhibit with the registrant's Annual Report on Form 10-K for the fiscal year ended December 31, 2008 filed with the SEC
on March 31, 2009 (File No. 001-34042).
Incorporated by reference to the filing of such exhibit with Amendment No. 2 to the registrant's Registration Statement on S-1 filed with the SEC on March 28, 2008 (File
No. 333-146137).

E-3

13.

14.

15.

16.

17.

18.

19.

20.

21.

22.

23.
24.
25.

Incorporated by reference to the filing of such exhibit with the registrant's Annual Report on Form 10-K for the fiscal year ended December 31, 2020 filed with the SEC
on March 15, 2021 (File No. 001-34042).
Incorporated  by  reference  to  the  filing  of  such  exhibit  with  the  registrant's  Quarterly  Report  on  Form  10-Q  for  the  period  ended  June  30,  2011  filed  with  the  SEC  on
August 8, 2011 (No. 001-34042).
Incorporated by reference to the filing of such exhibit with the registrant's Annual Report on Form 10-K for the fiscal year ended December 31, 2012 filed with the SEC
on March 11, 2013 (File No. 001-34042).
Incorporated  by  reference  to  the  filing  of  such  exhibit  with  the  registrant's  Quarterly  Report  on  Form  10-Q  for  the  period  ended  June  30,  2016  filed  with  the  SEC  on
August 9, 2016 (No. 001-34042).
Incorporated by reference to the filing of such exhibit with the registrant's Annual Report on Form 10-K for the fiscal year ended December 31, 2018 filed with the SEC
on March 15, 2019 (File No. 001-34042).
Incorporated by reference to the filing of such exhibit with the registrant's Quarterly Report on Form 10-Q for the period ended September 30, 2018 filed with the SEC on
November 9, 2018 (No. 001-34042).
Incorporated  by  reference  to  the  filing  of  such  exhibit  with  the  registrant's  Quarterly  Report  on  Form  10-Q  for  the  period  ended  June  30,  2012  filed  with  the  SEC  on
August 9, 2012 (File No. 001-34042).
Incorporated by reference to the filing of such exhibit with the registrant's Annual Report on Form 10-K for the fiscal year ended December 31, 2017 filed with the SEC
on March 1, 2018 (File No. 001-34042).
Incorporated by reference to the filing of such exhibit with the registrant's Quarterly Report on Form 10-Q for the period ended September 30, 2016 filed with the SEC on
November 8, 2016 (File No. 001-34042).
Incorporated by reference to the filing of such exhibit with the registrant's Annual Report on Form 10-K for the fiscal year ended December 31, 2021 filed with the SEC
on March 14, 2022 (File No. 001-34042).
Incorporated by reference to the filing of such exhibit with the registrant’s Current Report on Form 8-K filed with the SEC on January 3, 2019 (File No. 001-34042).
Incorporated by reference to the filing of such exhibit with the registrant’s Current Report on Form 8-K filed with the SEC on March 4, 2019 (File No. 001-34042).
Incorporated  by  reference  to  the  filing  of  such  exhibit  with  the  registrant's  Quarterly  Report  on  Form  10-Q  for  the  period  ended  June  30,  2019  filed  with  the  SEC  on
August 9, 2019 (File No. 001-34042).
† Filed herewith. * Management contract or compensatory plan or arrangement

E-4

Item 8. Financial Statements and Supplementary Data.

Index to Consolidated Financial Statements and Related Notes
Report of Independent Registered Public Accounting Firm (PCAOB ID No. 42)
Consolidated Balance Sheets as of December 31, 2022 and 2021
Consolidated Statements of Income for the Years Ended December 31, 2022 and 2021
Consolidated Statements of Comprehensive Income for the Years Ended December 31, 2022 and 2021
Consolidated Statements of Changes in Shareholders’ Equity for the Years Ended December 31, 2022 and 2021
Consolidated Statements of Cash Flows for the Years Ended December 31, 2022 and 2021
Notes to Consolidated Financial Statements

Note 1 — Organization
Note 2 — Significant Accounting Policies
Note 3 — Segment Information
Note 4 — Investments
Note 5 — Fair Value Measurements
Note 6 — Shareholders' Equity
Note 7 — Long-Term Debt
Note 8 — Reinsurance
Note 9 — Reserve for Loss and Loss Adjustment Expenses
Note 10 — Related Party Transactions
Note 11 — Commitments, Contingencies and Guarantees
Note 12 — Earnings Per Common Share
Note 13 — Income Taxes
Note 14 — Share Compensation and Pension Plans
Note 15 — Statutory Requirements and Dividend Restrictions

F-1

Page

F-2
F-4
F-5
F-6
F-7
F-8

F-9
F-10
F-16
F-20
F-25
F-28
F-31
F-32
F-33
F-48
F-51
F-54
F-55
F-57
F-59

REPORT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM

To the Shareholders and the Board of Directors of Maiden Holdings, Ltd.

Opinion on the Financial Statements

We  have  audited  the  accompanying  consolidated  balance  sheets  of  Maiden  Holdings,  Ltd.  (the  Company)  as  of  December  31,  2022  and  2021,  the  related
consolidated statements of income, comprehensive income, changes in shareholders' equity and cash flows for each of the years then ended, and the related notes
(collectively referred to as the “consolidated financial statements”). In our opinion, the consolidated financial statements present fairly, in all material respects, the
financial  position  of  the  Company  at  December  31,  2022  and  2021,  and  the  results  of  its  operations  and  its  cash  flows  for  each  of  the  years  then  ended,  in
conformity with U.S. generally accepted accounting principles.

We also have audited, in accordance with the standards of the Public Company Accounting Oversight Board (United States) (PCAOB), the Company’s internal
control  over  financial  reporting  as  of  December  31,  2022,  based  on  criteria  established  in  Internal  Control-Integrated  Framework  issued  by  the  Committee  of
Sponsoring Organizations of the Treadway Commission (2013 framework) and our report dated March 15, 2023 expressed an unqualified opinion thereon.

Basis for Opinion

These  financial  statements  are  the  responsibility  of  the  Company's  management.  Our  responsibility  is  to  express  an  opinion  on  the  Company’s  financial
statements based on our audits. We are a public accounting firm registered with the PCAOB and are required to be independent with respect to the Company in
accordance with the U.S. federal securities laws and the applicable rules and regulations of the Securities and Exchange Commission and the PCAOB.

We conducted our audits in accordance with the standards of the PCAOB. Those standards require that we plan and perform the audit to obtain reasonable
assurance about whether the financial statements are free of material misstatement, whether due to error or fraud. Our audits included performing procedures to
assess the risks of material misstatement of the financial statements, whether due to error or fraud, and performing procedures that respond to those risks. Such
procedures included examining, on a test basis, evidence regarding the amounts and disclosures in the financial statements. Our audits also included evaluating the
accounting principles used and significant estimates made by management, as well as evaluating the overall presentation of the financial statements. We believe
that our audits provide a reasonable basis for our opinion.

Critical Audit Matters

The critical audit matter communicated below is a matter arising from the current period audit of the financial statements that was communicated or required to
be communicated to the audit committee and that: (1) relates to accounts or disclosures that are material to the financial statements and (2) involved our especially
challenging, subjective or complex judgments. The communication of the critical audit matter does not alter in any way our opinion on the consolidated financial
statements, taken as a whole, and we are not, by communicating the critical audit matter below, providing a separate opinion on the critical audit matter or on the
account or disclosures to which it relates.

F-2

Description of the Matter

Valuation of Incurred but not Reported Reserves

At December 31, 2022, the Company’s reserve for loss and loss adjustment expenses was $1,131 million of which a significant
portion is incurred but not reported reserves. As explained in Notes 2 and 9 of the consolidated financial statements, the reserve
for  loss  and  loss  adjustment  expenses  represents  management’s  estimate  of  the  ultimate  costs  of  all  reported  and  unreported
losses incurred. There is significant uncertainty inherent in determining management’s estimate of the ultimate cost of all claims
that have occurred which is used to determine the incurred but not reported reserves. In particular, the estimate is sensitive to the
selection and weighting of actuarial methodologies used to project the ultimate costs and the selection of assumptions such as
payment and reporting patterns used to determine loss development factors and expected loss ratios.

Auditing management’s estimate of incurred but not reported reserves was complex due to the highly judgmental nature of the
significant  assumptions  used  in  the  valuation  of  the  estimate.  The  significant  judgment  was  primarily  due  to  the  sensitivity  of
management’s estimate to the actuarial methods selected and the assumptions used in the determination of the loss development
factors and ultimate claim costs.

How We Addressed the Mater
in our Audit

We  obtained  an  understanding,  evaluated  the  design  and  tested  the  operating  effectiveness  of  controls  over  the  Company’s
incurred but not reported reserving process. This included, among others, controls over the review and approval processes that
management has in place for the selection of actuarial methods and assumptions used in estimating the incurred but not reported
reserves.

To test the Company’s estimate of incurred but not reported reserves, our audit procedures included among others, the assistance
of  our  actuarial  specialists  to  evaluate  the  assumptions  used  by  comparing  the  significant  assumptions,  including  payment
patterns  and  expected  loss  ratios,  to  the  Company’s  historical  experience.  In  addition,  we  evaluated  the  selection  and  the
weighting of actuarial methods used by management against the maturity of the accident periods, changes in case reserve levels
and claims settlement patterns. We developed a range of reasonable reserve estimates, which included performing independent
projections for a sample of lines of business and compared the Company’s recorded reserves to the range of reasonable reserve
estimates. We also performed a review of the subsequent development of prior year loss and loss adjustment expense reserves.

/s/ Ernst & Young LLP

We have served as the Company’s auditor since 2020.

New York, NY
March 15, 2023

F-3

 
 
 
 
MAIDEN HOLDINGS, LTD.
CONSOLIDATED BALANCE SHEETS
As of December 31, 2022 and 2021
(In thousands of U.S. dollars, except share and per share data)

ASSETS

Investments:
Fixed maturities, available-for-sale, at fair value (amortized cost 2022 - $330,439; 2021 - $595,344)
Equity securities, at fair value (cost 2022 - $40,509; 2021 - $23,228))
Equity method investments
Other investments
Total investments
Cash and cash equivalents
Restricted cash and cash equivalents
Accrued investment income
Reinsurance balances receivable, net (includes $8,395 and $17,471 from related parties in 2022 and 2021,
respectively)
Reinsurance recoverable on unpaid losses
Loan to related party
Deferred commission and other acquisition expenses (includes $23,632 and $34,170 from related parties in 2022 and
2021, respectively)
Funds withheld receivable (includes $416,835 and $601,460 from related parties in 2022 and 2021, respectively)
Other assets

Total assets

LIABILITIES

Reserve for loss and loss adjustment expenses (includes $988,684 and $1,338,269 from related parties in 2022 and
2021, respectively)
Unearned premiums (includes $63,443 and $91,730 from related parties in 2022 and 2021, respectively)
Deferred gain on retroactive reinsurance
Accrued expenses and other liabilities (includes $33,278 and $29,408 from related parties in 2022 and 2021,
respectively)
Senior notes - principal amount
Less: unamortized issuance costs
Senior notes, net
Total liabilities
Commitments and Contingencies

EQUITY

Preference shares
Common shares ($0.01 par value; 149,224,080 and 92,316,107 shares issued in 2022 and 2021, respectively; 101,532,151 and
86,467,242 shares outstanding in 2022 and 2021, respectively)
Additional paid-in capital
Accumulated other comprehensive loss
Accumulated deficit
Treasury shares, at cost (47,691,929 and 5,848,865 shares in 2022 and 2021, respectively)
Total Maiden shareholders’ equity

Total liabilities and equity

$

$

$

$

See accompanying notes to Consolidated Financial Statements

F-4

2022

2021

314,527  $
43,621 
80,159 
148,753 
587,060 
30,986 
15,638 
4,122 

10,707 
556,116 
167,975 

24,976 
441,412 
7,874 
1,846,866  $

1,131,408  $
67,081 
47,708 

60,518 
262,500 
6,928 
255,572 
1,562,287 

597,145 
24,003 
83,742 
117,722 
822,612 
26,668 
39,419 
5,695 

19,507 
562,845 
167,975 

36,703 
636,412 
4,774 
2,322,610 

1,489,373 
100,131 
48,960 

44,542 
262,500 
7,153 
255,347 
1,938,353 

— 

159,210 

1,492 
884,259 
(41,234)
(442,863)
(117,075)
284,579 
1,846,866  $

923 
768,650 
(12,215)
(498,295)
(34,016)
384,257 
2,322,610 

 
 
MAIDEN HOLDINGS, LTD.
CONSOLIDATED STATEMENTS OF INCOME
(In thousands of U.S. dollars, except share and per share data)

For the Year Ended December 31,
Revenues
Gross premiums written
Net premiums written
Change in unearned premiums

Net premiums earned

Other insurance (expense) revenue, net
Net investment income
Net realized and unrealized investment (losses) gains

Total revenues

Expenses
Net loss and loss adjustment expenses
Commission and other acquisition expenses
General and administrative expenses
Interest and amortization expenses
Foreign exchange and other gains, net

Total expenses

(Loss) income before income taxes and interest in (loss) income of equity method investments
Income tax (benefit) expense
Interest in (loss) income in equity method investments
Net (loss) income

Gain from repurchase and exchange of preference shares

Net income available to Maiden common shareholders

Basic and diluted earnings per share available to common shareholders
Weighted average number of common shares - basic
Adjusted weighted average number of common shares and assumed conversions - diluted

See accompanying notes to Consolidated Financial Statements.

F-5

$

$

$

$

2022

2021

5,479  $

5,082  $

32,650 
37,732 
(4,530)
30,070 
(5,140)
58,132 

57,991 
18,511 
30,947 
19,331 
(8,255)
118,525 
(60,393)
(557)
(205)
(60,041)
115,473 
55,432  $

10,938 

10,403 
42,590 
52,993 
1,067 
32,013 
12,648 
98,721 

7,307 
24,840 
36,020 
19,327 
(7,685)
79,809 
18,912 
15 
7,748 
26,645 
90,998 
117,643 

0.63  $

87,112,711 
87,113,974 

1.35 
86,068,278 
86,072,667 

MAIDEN HOLDINGS, LTD.
CONSOLIDATED STATEMENTS OF COMPREHENSIVE INCOME
(In thousands of U.S. dollars)

For the Year Ended December 31,
Net (loss) income
Other comprehensive loss
Net unrealized holdings losses on fixed maturity investments arising during the year
Net unrealized holdings gains (losses) on equity method investments arising during the year
Adjustment for reclassification of net realized gains recognized in net (loss) income
Foreign currency translation adjustment
Other comprehensive loss, before tax
Income tax benefit related to components of other comprehensive loss
Other comprehensive loss, after tax

Comprehensive loss

$

See accompanying notes to Consolidated Financial Statements.

F-6

2022

2021

$

(60,041) $

26,645 

(10,906)
4,414 
(6,807)
(16,044)
(29,343)
324 
(29,019)
(89,060) $

(28,900)
(4,414)
(18,787)
15,978 
(36,123)
51 
(36,072)
(9,427)

MAIDEN HOLDINGS, LTD. 
CONSOLIDATED STATEMENTS OF CHANGES IN SHAREHOLDERS' EQUITY
(In thousands of U.S. dollars)

For the Year Ended December 31,
Preference shares – Series A, C and D
Beginning balance
Repurchase and exchange of Preference Shares – Series A
Repurchase and exchange of Preference Shares – Series C
Repurchase and exchange of Preference Shares – Series D
Ending balance
Common shares
Beginning balance
Shares issued on exchange of Preference Shares – Series A, C and D
Issuance of common shares from vesting of stock based compensation
Ending balance
Additional paid-in capital
Beginning balance
Issuance of common shares from vesting of share-based compensation
Share-based compensation expense
Repurchase and exchange of preference shares
Cash settlement of restricted shares granted
Issuance of common shares due to exchange of preference shares
Ending balance
Accumulated other comprehensive (loss) income
Beginning balance
Change in net unrealized losses on investment
Foreign currency translation adjustment
Ending balance
Accumulated deficit
Beginning balance
Cash settlement of restricted shares granted
Net (loss) income
Gain on repurchase and exchange of preference shares
Ending balance
Treasury shares
Beginning balance
Shares held by Maiden Reinsurance Ltd.
Shares repurchased for tax purposes
Ending balance

Total equity

2022

2021

$

$

159,210  $
(48,392)
(59,245)
(51,573)
— 

923 
558 
11 
1,492 

768,650 
(11)
2,740 
5,319 
10 
107,551 
884,259 

(12,215)
(12,975)
(16,044)
(41,234)

(498,295)
— 
(60,041)
115,473 
(442,863)

(34,016)
(82,050)
(1,009)
(117,075)
284,579  $

394,310 
(87,977)
(75,669)
(71,454)
159,210 

898 
— 
25 
923 

756,122 
(25)
4,771 
7,847 
(65)
— 
768,650 

23,857 
(52,050)
15,978 
(12,215)

(615,837)
(101)
26,645 
90,998 
(498,295)

(31,534)
— 
(2,482)
(34,016)
384,257 

See accompanying notes to Consolidated Financial Statements.

F-7

 
MAIDEN HOLDINGS, LTD. 
CONSOLIDATED STATEMENTS OF CASH FLOWS 
(In thousands of U.S. dollars)

For the Year Ended December 31,
Cash flows from operating activities:
Net (loss) income
Adjustments to reconcile net (loss) income to net cash flows from operating activities:
Depreciation, amortization and share-based compensation
Interest in loss (income) of equity method investments
Net realized and unrealized losses (gains) on investment
Foreign exchange and other gains, net

Changes in assets – (increase) decrease:

Reinsurance balances receivable, net
Reinsurance recoverable on unpaid losses
Accrued investment income
Deferred commission and other acquisition expenses
Funds withheld receivable
Other assets

Changes in liabilities – increase (decrease):
Reserve for loss and loss adjustment expenses
Unearned premiums
Deferred gain on retroactive reinsurance
Accrued expenses and other liabilities
Net cash used in operating activities
Cash flows from investing activities:
Purchases of fixed maturities
Purchases of other investments
Purchases of equity method investments
Purchases of equity securities
Proceeds from sales of fixed maturities
Proceeds from maturities, paydowns and calls of fixed maturities
Proceeds from sale and redemption of other investments
Proceeds from sale and redemption of equity method investments
Proceeds from sale and redemption of equity securities
Net proceeds from acquisition of a subsidiary
Others, net
Net cash provided by investing activities
Cash flows from financing activities:
Repurchase of preference shares
Cash settlement of restricted shares granted and options exercised
Repurchase of common shares
Net cash used in financing activities
Effect of exchange rate changes on foreign currency cash
Net decrease in cash, cash equivalents and restricted cash
Cash, cash equivalents and restricted cash - beginning of year
Cash, cash equivalents and restricted cash - end of year

Reconciliation of cash and restricted cash reported within Consolidated Balance Sheets:
Cash and cash equivalents, end of year
Restricted cash and cash equivalents, end of year

Total cash and cash equivalents and restricted cash and equivalents, end of year

Supplemental cash flow information:
Cash paid for interest, net of amounts capitalized
Cash paid for income taxes

See accompanying notes to Consolidated Financial Statements.

F-8

2022

2021

$

(60,041) $

26,645 

(112)
205 
5,140 
(8,255)

8,530 
10,822 
1,245 
11,601 
3,926 
(1,915)

(154,974)
(32,655)
2,335 
18,220 
(195,928)

(79,027)
(39,928)
(55,629)
(17,281)
213,944 
98,462 
4,403 
61,209 
— 
2,725 
(88)
188,790 

(9,984)
10 
(1,009)
(10,983)
(1,342)
(19,463)
66,087 
46,624  $

30,986  $
15,638 
46,624  $

19,106  $
1,149 

8,224 
(7,748)
(12,648)
(7,685)

(11,577)
594 
5,390 
15,013 
15,749 
(1,834)

(377,706)
(43,416)
3,100 
(6,531)
(394,430)

(247,553)
(55,165)
(44,050)
(20,523)
477,920 
344,989 
832 
6,777 
441 
421 
(25)
464,064 

(136,255)
(166)
(2,482)
(138,903)
(470)
(69,739)
135,826 
66,087 

26,668 
39,419 
66,087 

19,106 
109 

$

$

$

$

 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

1. Organization

Maiden  Holdings,  Ltd.  (sometimes  referred  to  as  "Maiden  Holdings"  or  "Parent  Company")  is  a  Bermuda-based  holding  company.  Together  with  its
subsidiaries (collectively referred to as the "Company", "we" or "Maiden"), Maiden creates shareholder value by actively managing and allocating our assets and
capital, including through ownership and management of businesses and assets primarily in the insurance and related financial services industries where we can
leverage  our  deep  knowledge  of  those  markets.  We  are  currently  underwriting  reinsurance  risks  on  a  retroactive  basis  through  our  indirect  wholly  owned
subsidiary Genesis Legacy Solutions ("GLS") which provides a full range of legacy services to small insurance companies, particularly those in run-off or with
blocks of reserves that are no longer core to those companies operations. GLS works with clients to develop and implement finality solutions including acquiring
entire companies that enable our clients to meet their capital and risk management objectives. We expect this legacy solutions business to contribute to our active
asset and capital management strategies. The Company does not presently underwrite prospective reinsurance risks.

Short-term income protection business is written on a primary basis by our wholly owned subsidiaries Maiden Life Försäkrings AB ("Maiden LF") and Maiden
General Försäkrings AB ("Maiden GF") in the Scandinavian and Northern European markets. Insurance support services are provided to Maiden LF and Maiden
GF  by  our  wholly  owned  subsidiary  services  company,  Maiden  Global  Holdings  Ltd.  (“Maiden  Global”),  which  is  also  a  licensed  intermediary  in  the  United
Kingdom.  Maiden  Global  had  previously  operated  internationally  by  providing  branded  auto  and  credit  life  insurance  products  through  insurer  partners,
particularly  those  in  the  European  Union  ("EU")  and  other  global  markets  ("IIS  business").  These  products  also  produced  reinsurance  programs  which  were
underwritten by our wholly owned subsidiary Maiden Reinsurance Ltd. (“Maiden Reinsurance”).

We  also  have  various  historic  reinsurance  programs  underwritten  by  Maiden  Reinsurance  which  are  in  run-off,  including  the  liabilities  associated  with
AmTrust Financial Services, Inc. ("AmTrust") reinsurance agreements which were terminated in 2019 as discussed in "Note 10 — Related Party Transactions". In
addition, we have a retroactive reinsurance agreement and a commutation agreement that further reduces our exposure and limits the potential volatility related to
AmTrust liabilities, which are discussed in "Note 8 — Reinsurance" of the Notes to Consolidated Financial Statements.

Genesis Legacy Solutions

Effective October 1, 2021, GLS completed its first loss portfolio transfer transaction which included an adverse development cover. GLS continues to write
additional retroactive reinsurance transactions and in 2022 has acquired insurance companies for run-off purposes, both consistent with its business plan. As of
December  31,  2022,  GLS  related  companies  and  its  subsidiaries  have  insurance  liabilities  that  it  assumed  through  retroactive  reinsurance  contracts  of  $45,089
which  included  total  reserves  of  $28,230,  an  underwriting-related  derivative  liability  of  $14,559,  and  deferred  gains  on  retroactive  reinsurance  of  $2,300.  In
addition to producing returns that exceed the target cost of capital, on a longer-term basis we expect business produced through GLS to further enhance our ability
to pursue the asset and capital management pillars of our business strategy.

Exchange of Preference Shares

On  December  27,  2022  (the  "Exchange  Date"),  the  Company  exchanged  all  of  its  outstanding  8.250%  Non-Cumulative  Preference  Shares,  Series  A  (the
“Series A Preference Shares”), 7.125% Non-Cumulative Preference Shares, Series C (the “Series C Preference Shares”) and 6.700% Non-Cumulative Preference
Shares, Series D (the “Series D Preference Shares” and, together with the Series A Preference Shares and the Series C Preference Shares, the “Preference Shares”)
for  its  common  shares,  $0.01  par  value  per  share  (the  "Exchange").  To  effectuate  the  Exchange  under  the  terms  of  each  series  of  the  Preference  Shares,  the
affirmative vote of holders of two-thirds of the issued shares of each series of Preference Shares was required. Maiden Reinsurance, which owned approximately
74% of each series of Preference Shares immediately preceding the Exchange Date, consented to the variation in order to effectuate the Exchange. The Exchange
was  approved  by  a  special  committee  of  the  Board  of  the  Company  consisting  of  disinterested  directors  and,  upon  advice  of  the  special  committee's  financial
advisor, approved a conversion ratio of three common shares per preference share for record holders of the Preference Shares. Under the terms of the Exchange,
preference shareholders received common shares of the Company having a fair value that meets the “Minimum Price” as determined in accordance with the rules
of the Nasdaq and as described in an information statement that the Company filed with the Securities and Exchange Commission (the “SEC”) and distributed to
preference shareholders. As a result of the Exchange, the Preference Shares were delisted and no longer trade on the New York Stock Exchange, and there are no
remaining  issued  and  outstanding  Preference  Shares  as  at  December  31,  2022.  All  rights  of  the  former  holders  related  to  ownership  of  the  Preference  Shares
terminated upon completion of the Exchange.

As of December 27, 2022, Maiden Reinsurance owns 29% of the Company's total outstanding common shares as described above, which is eliminated for
accounting and financial reporting purposes on the Company’s consolidated financial statements. The voting power of Maiden Reinsurance, with respect to its
common shares, will be capped at 9.5% pursuant to the bye-laws of the Company. The Exchange and the ownership of the common shares by Maiden Reinsurance
was  made  in  compliance  with  Maiden  Reinsurance's  investment  policy  which  was  approved  by  the  Vermont  Department  of  Financial  Regulation  ("Vermont
DFR"). The Vermont DFR additionally specifically approved the ownership of the Company's common shares by Maiden Reinsurance related to the Exchange.

The Company recorded a gain of approximately $87,240 as a result of the Exchange. Please see "Note 6 — Shareholders' Equity" for further discussion.

F-9

 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

2. Significant Accounting Policies

Basis  of  Reporting  and  Consolidation  —  These  Consolidated  Financial  Statements  have  been  prepared  in  conformity  with  accounting  principles  generally
accepted in the U.S. ("U.S. GAAP") and include the accounts of Maiden Holdings and all of its subsidiaries. These Consolidated Financial Statements reflect all
adjustments that are, in the opinion of management, necessary for a fair presentation of the results for the period and all such adjustments are of a normal recurring
nature.  All  significant  intercompany  transactions  and  accounts  have  been  eliminated.  Certain  prior  year  comparatives  have  been  reclassified  to  conform  to  the
current year presentation. The effect of these reclassifications had no impact on previously reported shareholders' equity or net income.

Estimates  —  The  preparation  of  U.S.  GAAP  Consolidated  Financial  Statements  requires  management  to  make  estimates  and  assumptions  that  affect  the
reported and disclosed amounts of assets and liabilities and disclosure of contingent assets and liabilities at the date of the Consolidated Financial Statements and
the reported amounts of revenues and expenses during the reporting period. Actual results could materially differ from those estimates. The significant estimates
include,  but  are  not  limited  to,  reserve  for  loss  and  loss  adjustment  expenses  ("loss  and  LAE"),  deferred  gain  on  retroactive  reinsurance;  recoverability  of
reinsurance balances receivable, reinsurance recoverable on unpaid losses, funds withheld and deferred commission and other acquisition expenses; valuation of
financial instruments and deferred tax assets; and the determination of other-than-temporary impairment ("OTTI") of investments.

Fixed Maturity Investments — The Company classifies its fixed maturity investments as available-for-sale ("AFS"). The AFS portfolio is reported at fair value
and any unrealized gains or losses are reported as a component of accumulated other comprehensive income ("AOCI") in shareholders' equity. The fair value of
fixed maturity investments is generally determined from quotations received from third-party nationally recognized pricing services ("Pricing Service"), or when
such prices are not available, by reference to broker or underwriter bid indications.

Short-term investments - These investments are comprised of securities due to mature within one year of the date of purchase. The Company held no short-term

investments as at December 31, 2022 and 2021.

Equity securities - Equity securities include publicly traded common and preferred stocks, and privately held common and preferred stocks. The fair value of
publicly traded common and preferred stocks is primarily priced by pricing services, reflecting the closing price quoted for the final trading day of the period.
These  investments  are  carried  at  fair  value  using  a  combination  of  observable  and  unobservable  inputs  including  but  not  limited  to  market  pricing  data  and
quarterly  financial  statements.  Any  unrealized  gains  or  losses  on  the  investment,  including  the  portion  attributable  to  changes  in  foreign  exchange  rates,  are
recorded in net income in the reporting period in which it occurs. The privately held common and preferred stocks are valued using significant inputs that are
unobservable where there is little or no market activity. Unadjusted third party pricing sources or management's assumptions and internal valuation models may be
used to determine their fair values.

Other  investments  —  The  Company  accounts  for  its  other  investments  at  fair  value  in  accordance  with  Financial  Accounting  Standards  Board  ("FASB")
Accounting  Standards  Codification  ("ASC")  Topic  944-325,  "Financial  Services  -  Insurance  -  Investments  -  Other"  ("ASC  944-325").  Other  investments  are
comprised of the following types of investments:

•Privately held investments: These are direct equity investments in common and preferred stock of privately held entities. The fair values are estimated
using  guideline  public  company  data  to  determine  a  price-to-book  ratio  trading  multiple  which  was  applied  to  book  values  shown  on  the  quarterly
financial statements as well as recent private market transactions. These investments are also comprised of investments in insurtech and other insurance
focused companies. The fair value of start-up insurance entities are determined using recent private market transactions where applicable. Any changes in
fair value are reported in net realized and unrealized gains (losses) and recognized in net earnings.

•Private credit funds: These are privately held equity investments in limited partnerships or common stock of entities that lend money valued using the
most  recently  available  or  quarterly  net  asset  value  ("NAV")  statements  as  provided  by  the  external  fund  manager  or  third-party  administrator.  Any
changes in fair value are reported in realized gains (losses) and recognized in net earnings.

•Private equity funds: These are comprised of private equity funds, private equity co-investments with sponsoring entities and investments in real estate
limited partnerships and joint ventures. The fair value is estimated based on the most recently available NAV as advised by the external fund manager or
third-party administrator. Any changes in fair value are reported in realized gains (losses) and recognized in net earnings.

•Investments  in  direct  lending  entities:  These  investments  are  carried  at  cost  less  impairment,  if  any,  with  any  indication  of  impairment  recognized  in
income when determined.

The valuation of other investments is further described in Note 5 — Fair Value Measurements. Due to a lag in the valuations of certain funds reported by the
investment  managers,  the  Company  may  record  changes  in  valuation  with  up  to  a  three-month  lag.  The  Company  regularly  reviews  and  discusses  fund
performance with the investment managers or sponsors to corroborate the reasonableness of the reported NAV and to assess whether any events have occurred
within the lag period that would affect the valuation of the investments.

Equity  Method  Investments  —  Investments  in  which  the  Company  has  significant  influence  over  the  operating  and  financial  policies  of  the  investee  are
classified as equity method investments and accounted for using the equity method of accounting. In applying the equity method of accounting, investments are
initially recorded at cost and are subsequently adjusted based on the Company’s proportionate share of the investee's net income or loss, net of any contributions
and distributions received.

F-10

 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

2. Significant Accounting Policies (continued)

Adjustments are based on the most recent available financial information from the investee. Changes in the carrying value of these investments are recorded in
net  income  (loss)  as  the  interest  in  income  (loss)  of  equity  method  investments.  The  Company  records  its  share  of  the  investee’s  other  comprehensive  income
("OCI") activity based on its proportionate share of the investee's common stock or capital, and books any OCI activity directly to the equity method investments
account, with the offset recorded to the Company's AOCI.

Purchases and sales of investments are recorded on a trade date basis. Realized gains or losses on investment sales are determined based on the first in first out
cost method. Net investment income is recognized when earned and includes accrued interest and dividend income together with amortization of market premiums
and discounts using the constant yield method, net of investment management fees. For U.S. government agency mortgage-backed securities ("Agency MBS") and
any other holdings for which there is a prepayment risk, prepayment assumptions are evaluated and revised as necessary. Any changes required due to movements
in effective yields and maturities are recognized on a prospective basis through yield adjustments.

A security is potentially impaired when its fair value falls below its amortized cost. On a quarterly basis, all potentially impaired securities are reviewed to
determine  whether  the  impairment  is  temporary  or  OTTI.  OTTI  assessments  are  inherently  judgmental,  especially  where  securities  have  experienced  severe
declines  in  fair  value  over  a  short  period.  The  Company's  review  process  begins  with  a  quantitative  analysis  to  identify  securities  to  be  further  evaluated  for
potential  classification  as  OTTI.  For  all  identified  securities,  further  fundamental  analysis  is  performed  that  considers,  but  is  not  limited  to,  the  following
quantitative and qualitative factors: historic and implied volatility of the security; length of time and extent to which the fair value has been less than amortized
cost; adverse conditions specifically related to the security or to specific conditions in an industry or geographic area; failure, if any, of the issuer of the security to
make scheduled payments; and recoveries or additional declines in fair value subsequent to the balance sheet date.

The Company recognizes OTTI losses within earnings for its impaired fixed maturity securities (i) for which the Company has the intent to sell the security or
(ii) it is more likely than not that the Company will be required to sell the debt security before its anticipated recovery and (iii) for those securities which have a
credit loss. In assessing whether a credit loss exists, the Company compares the present value of the cash flows expected to be collected from the security with the
amortized cost basis of the security. In instances in which a determination is made that an impairment exists but the Company does not intend to sell the security
and it is not more likely than not that the Company will be required to sell the security before the anticipated recovery of its remaining amortized cost basis, the
impairment is separated into (i) the amount of the total impairment related to the credit loss and (ii) the amount of the total impairment related to all other factors.

The amount of the total OTTI related to the credit loss is recognized in earnings. The amount of the total OTTI related to all other factors is recognized in OCI.
In  periods  after  the  recognition  of  OTTI  on  the  fixed  maturity  securities,  the  Company  accounts  for  such  securities  as  if  they  had  been  purchased  on  the
measurement  date  of  the  OTTI  at  an  amortized  cost  basis  equal  to  the  previous  amortized  cost  basis  less  the  OTTI  recognized  in  earnings.  For  fixed  maturity
securities in which an OTTI loss was recognized in earnings, the difference between the new amortized cost basis and the cash flows expected to be collected will
be amortized into net investment income.

As the Company's fixed maturity investment portfolio is one of the largest component of its consolidated assets, any OTTI on fixed maturity securities could be

material to the Company's financial condition and results particularly during periods of dislocation in the financial markets.

Fair Value Measurements — ASC Topic 820, "Fair Value Measurements and Disclosures" ("ASC 820") defines fair value as the price that would be received
upon the sale of an asset or paid to transfer a liability in an orderly transaction between open market participants at the measurement date. Additionally, ASC 820
establishes  a  hierarchy  for  inputs  used  in  measuring  fair  value  that  maximizes  the  use  of  observable  inputs  and  minimizes  the  use  of  unobservable  inputs  by
requiring that the most observable inputs be used when available. The hierarchy is broken down into three levels based on the reliability of inputs:

• Level 1 — Valuations based on unadjusted quoted market prices for identical assets or liabilities that we have the ability to access. Because valuations are
based  on  quoted  prices  that  are  readily  and  regularly  available  in  an  active  market,  valuation  of  these  products  does  not  entail  a  significant  degree  of
judgment. Examples of assets and liabilities utilizing Level 1 inputs include: U.S. Treasury bonds;

• Level 2 — Valuations based on quoted prices for similar assets or liabilities in active markets, quoted prices for identical assets or liabilities in inactive
markets, or valuations based on models where the significant inputs are observable (e.g. interest rates, yield curves, prepayment speeds, default rates, loss
severity,  etc.)  or  can  be  corroborated  by  observable  market  data.  Examples  of  assets  and  liabilities  utilizing  Level  2  inputs  include:  U.S.  government-
sponsored  agency  securities;  non-U.S.  government  and  supranational  obligations;  commercial  mortgage-backed  securities  ("CMBS");  collateralized  loan
obligations ("CLO"); corporate and municipal bonds; and

• Level 3 — Valuations based on models where significant inputs are not observable. The unobservable inputs reflect our own assumptions about assumptions
that  market  participants  would  use,  developed  on  the  basis  of  the  best  information  available  in  the  particular  circumstances.  Examples  of  assets  and
liabilities utilizing Level 3 inputs include: an investment in preference shares of a start-up insurance producer.

The availability of observable inputs can vary and is affected by a wide variety of factors, including, for example, the type of financial instrument, whether the

financial instrument is new and not yet established in the marketplace, and other characteristics particular to the transaction.

F-11

 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

2. Significant Accounting Policies (continued)

To  the  extent  that  valuation  is  based  on  models  or  inputs  that  are  less  observable  or  unobservable  in  the  market,  the  determination  of  fair  value  requires
significantly more judgment. Accordingly, the degree of judgment exercised by management in determining fair value is greatest for instruments categorized in the
Level 3 hierarchy.

The Company uses prices and inputs that are current as at the measurement date. In periods of market dislocation, the observability of prices and inputs may be

reduced for many instruments. This condition could cause a financial instrument to be reclassified between hierarchy levels.

For investments that have quoted market prices in active markets, the Company uses the quoted market prices as fair value and includes these in the Level 1
hierarchy. The Company receives quoted market prices from a third party nationally recognized Pricing Service. When quoted market prices are unavailable, the
Company utilizes the Pricing Service to determine an estimate of fair value. The fair value estimates are included in the Level 2 hierarchy. The Company will
challenge  any  prices  for  its  investments  which  are  considered  not  to  be  representative  of  fair  value.  If  quoted  market  prices  and  an  estimate  from  the  Pricing
Service  are  unavailable,  the  Company  produces  an  estimate  of  fair  value  based  on  dealer  quotations  for  recent  activity  in  positions  with  the  same  or  similar
characteristics to that investment being valued. The Company determines whether the fair value estimate is in the Level 2 or Level 3 hierarchy depending on the
level of observable inputs available when estimating the fair value. The Company bases its estimates of fair values for assets on the bid price as it represents what
a third party market participant would be willing to pay in an orderly transaction.

Cash and Cash Equivalents — The Company maintains cash accounts in several banks and brokerage institutions. Cash equivalents consist of investments in
money market funds and short-term investments with an original maturity of 90 days or less and are stated at cost, which approximates fair value. Restricted cash
and  cash  equivalents  are  separately  reported  in  the  Consolidated  Balance  Sheets.  The  Company  maintains  certain  cash  and  investments  in  trust  accounts  used
primarily  as  collateral  for  unearned  premiums  and  loss  and  LAE  reserves  owed  to  insureds.  The  Company  is  required  to  maintain  minimum  balances  in  these
restricted accounts based on pre-determined formulas. Please see "Note 4. (e) Investments" for further details.

Premiums and Related Expenses — For pro-rata contracts and excess-of-loss contracts where no deposit or minimum premium is specified in the contract,
premium written is recognized based on estimates of ultimate premiums provided by the ceding companies. Initial estimates of premium written are recognized in
the  period  in  which  the  underlying  risks  are  incepted.  Subsequent  adjustments,  based  on  reports  of  actual  premium  by  the  ceding  companies,  or  revisions  in
estimates, are recorded in the period in which they are determined. Reinsurance premiums assumed are generally earned on a pro-rata basis over the terms of the
underlying  policies  or  reinsurance  contracts.  Contracts  and  policies  written  on  a  "losses  occurring"  basis  cover  claims  that  may  occur  during  the  term  of  the
contract or policy, which is typically twelve months. Accordingly, the premium is earned evenly over the term. Contracts which are written on a "risks attaching"
basis cover claims which attach to the underlying insurance policies written during the terms of such contracts. Premiums earned on such contracts usually extend
beyond the original term of the reinsurance contract, typically resulting in recognition of premiums earned over a 24-month period.

Reinsurance premiums on specialty risk and extended warranty are earned based on the estimated program coverage period. These estimates are based on the
expected distribution of coverage periods by contract at inception, because a single contract may contain multiple coverage period options, and these estimates are
revised based on the actual coverage period selected by the original insured. Unearned premiums represent the portion of premiums written which is applicable to
the unexpired term of the contract or policy in force. These premiums can be subject to estimates based upon information received from ceding companies and any
subsequent differences arising on such estimates are recorded in the period in which they are determined.

Assumed and ceded reinsurance contracts that lack a significant transfer of risk are treated as deposits. No deposit contracts are held as at December 31, 2022

and 2021.

Acquisition expenses represent the costs of writing business that vary with, and are primarily related to, the production of that business. Policy and contract

acquisition expenses, including assumed commissions, are deferred and recognized as expense as the related premiums are earned.

The Company considers anticipated investment income in determining the recoverability of these costs and believes they are fully recoverable. A premium
deficiency is recognized if the sum of anticipated loss and LAE, unamortized acquisition expenses less anticipated investment income exceed unearned premiums.

Loss and LAE — Loss and LAE represent the estimated ultimate net costs of all reported and unreported losses incurred through December 31 of the latest
fiscal year. The reserve for loss and LAE is estimated using a statistical analysis of actuarial data and is not discounted for the time value of money. Although
considerable variability is inherent in the estimates of reserves for loss and LAE, management believes that the reserve for loss and LAE is adequate based on
known information to date. In estimating loss reserves, the Company utilizes a variety of standard actuarial methods. These estimates are continually reviewed and
adjusted as necessary as experience develops or new information becomes available. Such adjustments are included and reported in current operations as favorable
or unfavorable prior period development.

Reinsurance — Reinsurance premiums and loss and LAE ceded to other companies are accounted for on a basis consistent with those used in accounting for
original policies issued and pursuant to the terms of the reinsurance contracts. The Company records premiums earned and loss and LAE incurred and ceded to
other companies as reduction of premium revenue and loss and LAE, respectively. The unexpired portion of reinsurance purchased by the Company (retrocession
or reinsurance premiums ceded) is included in other assets and amortized over the contract period in proportion to the amount of insurance protection provided.
The ultimate amount of premiums, including adjustments, is recognized as premiums ceded and amortized over the applicable contract period to which they apply.

F-12

 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

2. Significant Accounting Policies (continued)

Premiums earned are reported net of reinsurance in the Consolidated Statements of Income. Reinsurance recoverable on unpaid losses relate to the portion of
reserves  and  paid  losses  and  LAE  that  are  ceded  to  other  companies.  Reinsurance  recoverable  on  unpaid  losses  are  separately  recorded  as  an  asset  in  the
Consolidated Balance Sheets. The Company remains contingently liable for all loss payments in the event of failure to collect from reinsurers.

Retroactive Reinsurance - Retroactive reinsurance agreements are those in which a reinsurer agrees to reimburse the ceding company for liabilities incurred as
a result of past insurable loss events. We do not record any income or expense on recognition of the reinsurance contract's assets and liabilities at inception, except
for any gains realized as a result of bargain purchase acquisitions which are recorded as part of foreign exchange and other gains (losses) immediately in income.
Any subsequent remeasurement of the value of liabilities is recorded to net loss and LAE within the Consolidated Statements of Income.

For ceded retroactive agreement, the excess of the amounts ultimately collectible under the agreement over the consideration paid is recognized as a deferred
gain liability which is amortized into income over the settlement period of the ceded reserves once the paid losses have exceeded the minimum retention. The
amount of the deferral is recalculated each period based on actual loss payments and updated estimates of ultimate losses. If the consideration paid exceeds the
ultimate losses collectible under the agreement, the net loss on the retroactive reinsurance agreement is recognized within income immediately.

At the inception of a run-off retroactive reinsurance contract, if the estimated undiscounted ultimate losses payable are in excess of the premiums received, a
deferred charge asset is recorded for the excess; whereas, if the premiums received are in excess of the estimated undiscounted ultimate losses payable, a deferred
gain  liability  is  recorded  for  the  excess,  such  that  we  do  not  record  any  gain  or  loss  at  the  inception  of  these  retroactive  reinsurance  contracts.  The  premium
consideration that we charge the ceding companies under retroactive reinsurance contracts may be lower than the undiscounted estimated ultimate losses payable
due to the time value of money. After receiving the premium consideration in full from cedents at the inception of the contract, we invest the premium received
over an extended period of time, thereby generating investment income. We expect to generate profits from these retroactive reinsurance contracts when taking
into account the premium received and expected investment income, less contractual obligations and expenses.

Deferred charge assets will be recorded in other assets (if and when applicable), and deferred gain liabilities are shown separately in the Consolidated Balance
Sheets, and amortized over the estimated claim payment period of the related contract with the periodic amortization reflected in income as a component of net
loss and LAE. The amortization of deferred charge assets and deferred gain liabilities is adjusted at each reporting period to reflect new estimates of the amount
and  timing  of  remaining  loss  and  LAE  payments.  Changes  in  the  estimated  amount  and  timing  of  payments  of  unpaid  losses  may  have  an  effect  on  the
unamortized deferred charge assets and deferred gain liabilities and the amount of periodic amortization.

Debt Obligations and Deferred Debt Issuance Costs — Costs incurred in issuing debt are capitalized and amortized over the contractual life of the debt. The
amortization of these costs are included in interest and amortization expenses in the Consolidated Statements of Income. The unamortized amount of issuance
costs is presented as a deduction from the related principal liability for senior notes in the Consolidated Balance Sheets.

Leases — The Company's leases are all currently classified as operating leases and none of them have non-lease components. For operating leases that have a
lease term of more than twelve months, the Company recognized a lease liability (presented as part of accrued expenses and other liabilities) and a right-of-use
asset (presented as part of other assets) in the Consolidated Balance Sheets at the present value of the remaining lease payments until expiration. As the lease
contracts  generally  do  not  provide  an  implicit  discount  rate,  the  Company  used  a  weighted-average  discount  rate  of  10%,  representing  its  estimated  secured
incremental borrowing rate, in calculating the present value of the lease liability. The Company has made an accounting policy election not to include renewal,
termination, or purchase options that are not reasonably certain of exercise when determining the term of the borrowing. The Company recognizes the related
leasing expense on a straight-line basis over the lease term in the Company's Consolidated Statements of Income.

Derivative  Instruments  —  The  Company  has  certain  reinsurance  contracts  that  are  accounted  for  as  derivatives.  These  reinsurance  contracts  provide
indemnification to an insured or cedant as a result of a change in a variable as opposed to an identifiable insurable event. The Company considers these contracts
to be part of its underwriting operations. The derivatives are initially valued at cost which approximates fair value. In subsequent measurement periods, the fair
values  of  the  underwriting-related  derivatives  are  determined  using  internally  developed  discounted  cash  flow  models  using  appropriate  discount  rates.  The
selection  of  an  appropriate  discount  rate  is  judgmental  and  is  the  most  significant  unobservable  input  used  in  the  valuation  of  these  derivatives.  A  significant
increase (decrease) in this input in isolation could result in a significantly lower (higher) fair value measurement for the derivative contract. The fair value changes
in underwriting-related derivative instruments is included within other insurance (expense) revenue. The underwriting-related derivative liability is presented as
part of accrued expenses and other liabilities in the Consolidated Balance Sheets and adjusted as a non-cash item in net cash flows from operating activities in the
Consolidated Statement of Cash Flows.

Income Taxes — The Company accounts for income taxes using ASC Topic 740 "Income Taxes" for subsidiaries operating in taxable jurisdictions. Deferred
income taxes reflect the expected future tax consequences of temporary differences between the carrying amounts of assets and liabilities for financial reporting
purposes and amounts used for income tax purposes. A valuation allowance is recorded if it is more likely than not that some or all of a deferred tax asset may not
be realized. The Company considers future taxable income and feasible tax planning strategies in assessing the need for a valuation allowance. In the event the
Company determines that it will not be able to realize all or part of its deferred income tax assets in the future, an adjustment to the deferred income tax assets
would be charged to income in the period in which such determination is made.

F-13

 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

2. Significant Accounting Policies (continued)

In addition, if the Company subsequently assesses that the valuation allowance is no longer needed, a benefit would be recorded to income in the period in
which such determination is made. U.S. GAAP allows for the recognition of tax benefits of uncertain tax positions only where the position is more likely than not
to be sustained assuming examination by tax authorities. A liability is established for any tax benefit claimed in a tax return in excess of this threshold. Income tax
related interest and penalties would be included as income tax expense. The Company has not recorded or accrued any interest or penalties during the years ended
December 31, 2022 and 2021.

Share-Based  Compensation  Expense  —  Pursuant  to  the  2019  Omnibus  Incentive  Plan,  the  Company  is  authorized  to  issue  restricted  share  awards  and
performance-based  restricted  shares,  share  options  and  other  equity-based  awards  to  its  employees  and  directors.  The  Company  recognizes  the  compensation
expense for share options and restricted share grants based on the fair value of the award on the date of grant, over the requisite service vesting period. Forfeitures
are accounted for if and when they occur. The estimated fair value of the grant is amortized ratably over its vesting period as a charge to compensation expense (as
a component of general and administrative expenses) and an increase to additional paid-in capital in the Consolidated Shareholders’ Equity.

Earnings Per Share — Basic earnings per share are computed based on the weighted-average number of common shares outstanding and exclude any dilutive
effects  of  share  options,  and  unvested  restricted  shares  units.  Dilutive  earnings  per  share  are  computed  using  the  weighted-average  number  of  common  shares
outstanding during the period adjusted for the dilutive impact of share options. The two-class method is used to determine earnings per share based on dividends
declared on common shares and participating securities (i.e. distributed earnings) and participation rights of participating securities in any undistributed earnings.
Each unvested restricted share granted by the Company to certain employees and directors is considered a participating security and the two-class method is used
to calculate net income attributable to Maiden common shareholders per common share – basic and diluted. However, any undistributed losses are not allocated to
the participating securities.

Net  income  available  to  Maiden  common  shareholders  per  common  share  –  basic  and  diluted  is  also  adjusted  for  any  gain  or  loss  from  the  redemption  or
extinguishment of the Company's preference shares. The gain on the repurchase and exchange of preference shares had an impact of $1.33 per common share for
the year ended December 31, 2022.

Treasury Shares — Treasury shares include common shares repurchased by the Company and not subsequently cancelled as well as share repurchases from
employees,  which  represent  withholding  in  respect  of  tax  obligations  on  the  vesting  of  restricted  shares  and  performance  based  shares.  Treasury  shares  are
recorded at cost and result in a reduction of the total Maiden shareholders’ equity in the Consolidated Balance Sheets.

Treasury shares also include common shares owned by Maiden Reinsurance due to the Exchange which are eliminated for accounting and financial reporting
purposes  in  the  Company’s  consolidated  financial  statements.  The  common  shares  held  by  Maiden  Reinsurance  are  presented  as  treasury  shares  on  the
Consolidated Balance Sheet at December 31, 2022. Since treasury shares are not considered outstanding for share count purposes, the common shares held by
Maiden Reinsurance are excluded from the average number of common shares outstanding for basic and diluted earnings per share.

Common share issuance costs incurred directly as a result of the Exchange have been deferred and offset against additional paid-in capital of the new common

shares issued to non-affiliates.

Foreign Currency Transactions  — The  functional  currency  of  the  Company  and  many  of  its  subsidiaries  is  the  U.S.  dollar.  For  these  companies,  monetary
assets and liabilities denominated in foreign currencies are translated at year-end exchange rates, with resulting foreign exchange gains and losses recognized in
the Consolidated Statements of Income. Revenues and expenses in foreign currencies are converted at average exchange rates during the year. Monetary assets and
liabilities include cash and cash equivalents, reinsurance balances receivable, reinsurance recoverable on unpaid losses, funds withheld receivable, reserve for loss
and LAE and accrued expenses and other liabilities. Accounts that are classified as non-monetary such as deferred commission and other acquisition expenses and
unearned premiums are not revalued.

Assets and liabilities of foreign subsidiaries and divisions, whose functional currency is not the U.S. dollar, are translated at year-end exchange rates. Revenues
and  expenses  of  these  entities  are  translated  at  average  exchange  rates  during  the  year.  The  effects  of  the  foreign  currency  translation  adjustment  for  foreign
entities are included in AOCI. The amount of the cumulative translation adjustment at December 31, 2022 was $(25,566) (2021 - $(9,522)).

Recently Adopted Accounting Standards Updates

No new accounting standards have been recently adopted for the year ended December 31, 2022.

Recently Issued Accounting Standards Not Yet Adopted

Accounting for Measurement of Credit Losses on Financial Instruments

In June 2016, the FASB issued ASU 2016-13 "Financial Instruments: Credit Losses (Topic 326)" replacing the "incurred loss" impairment methodology with
an  approach  based  on  "expected  losses"  to  estimate  credit  losses  on  certain  types  of  financial  instruments  and  requires  consideration  of  a  broader  range  of
reasonable and supportable information to inform credit loss estimates. The guidance requires financial assets to be presented at the net amount expected to be
collected. The allowance for credit losses is a valuation account that is deducted from the cost of the financial asset to present the net carrying value at the amount
expected to be collected on the financial asset.

F-14

 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

2. Significant Accounting Policies (continued)

ASU  2016-13  also  modified  the  accounting  for  AFS  debt  securities,  which  must  be  individually  assessed  for  credit  losses  when  fair  value  is  less  than  the
amortized cost basis, in accordance with Subtopic 326-30, Financial Instruments: Credit Losses Available-for-Sale Debt Securities. Credit losses relating to AFS
debt securities will be recorded through an allowance for credit losses rather than under the current OTTI methodology.

In  April  2019,  the  FASB  issued  ASU  2019-04  for  targeted  improvements  related  to  ASU  2016-13  which  clarify  that  an  entity  should  include  all  expected
recoveries in its estimate of the allowance for credit losses. In addition, for collateral dependent financial assets, the amendments mandate that an allowance for
credit losses that is added to the amortized cost basis of the financial asset should not exceed amounts previously written off. It also clarifies FASB’s intent to
include  all  reinsurance  recoverables  within  the  scope  of  Topic  944  to  be  within  the  scope  of  Subtopic  326-20,  regardless  of  the  measurement  basis  of  those
recoverables. The Company's reinsurance recoverable on unpaid losses is currently the most significant financial asset within the scope of ASU 2016-13.

The guidance is effective for public business entities, excluding entities eligible to be smaller reporting companies ("SRCs") as defined by the SEC, for annual
periods beginning after December 15, 2019, and interim periods therein. The guidance is effective for all other entities, including public entities eligible to be
SRCs, for fiscal years beginning after December 15, 2022, including interim periods within those fiscal years. As of December 31, 2022, the Company qualified
for SRC status, as determined on the last business day of its most recent second quarter, and thus remains eligible to follow the reporting deadlines and effective
dates applicable to SRCs. Therefore, Topic 326 will be adopted by the Company on January 1, 2023.

The  Company  has  evaluated  the  impact  of  this  guidance  on  its  results  of  operations,  financial  condition  and  liquidity  and  has  determined  that  a  $5,586
allowance  for  expected  credit  losses  will  be  necessary  on  the  reinsurance  recoverable  on  unpaid  losses  and  other  investments  held  at  the  time  of  adoption  on
January 1, 2023.

Fair Value Measurement of Equity Securities Subject to Contractual Sale Restrictions

In  June  2022,  FASB  issued  Accounting  Standards  Update  ("ASU")  2022-03  "Fair  Value  Measurement  of  Equity  Securities  Subject  to  Contractual  Sale
Restrictions"  an  amendment  of  Fair  Value  Measurement  (Topic  820).  The  amendments  in  this  ASU  require  the  Company  to  provide  disclosures  for  equity
securities subject to contractual sale restrictions under 820-10-50-6B including the fair value of equity securities subject to contractual sale restrictions reflected in
the balance sheet; the nature and remaining duration of the restrictions; and any circumstances that could cause a lapse in the restrictions. For public business
entities, the amendments are effective for fiscal years beginning after December 15, 2023, and interim periods within those fiscal years.

Certain of the Company's equity securities are subject to restrictions on redemptions and sales that are determined by the governing documents, which could
limit our ability to liquidate those investments. These restrictions may include lock-ups, redemption gates, restricted share classes, restrictions on the frequency of
redemption and notice periods as described in "Note 4. (b) Investments". The Company is currently assessing the required disclosures for equity securities that
may be subject to contractual sales restrictions. These amendments only impact disclosures made in "Note 4. Investments" therefore, the adoption of this standard
will not impact the Company’s consolidated balance sheets, results of operations or statement of cash flows.

F-15

 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

3. Segment Information

The Company currently has two reportable segments: Diversified Reinsurance and AmTrust Reinsurance. Our Diversified Reinsurance segment consists of a
portfolio  of  predominantly  property  and  casualty  reinsurance  business  focusing  on  regional  and  specialty  property  and  casualty  insurance  companies  located
primarily in Europe. This segment also includes transactions entered into by GLS which was formed in November 2020 as described in "Note 1 — Organization".
Our AmTrust Reinsurance segment includes all business ceded to Maiden Reinsurance by AmTrust, primarily the quota share reinsurance agreement (“AmTrust
Quota Share”) between Maiden Reinsurance and AmTrust’s wholly owned subsidiary, AmTrust International Insurance, Ltd. (“AII”), and the European hospital
liability  quota  share  reinsurance  contract  ("European  Hospital  Liability  Quota  Share")  with  AmTrust’s  wholly  owned  subsidiaries,  AmTrust  Europe  Limited
("AEL") and AmTrust International Underwriters DAC ("AIU DAC"), which are both in run-off effective January 1, 2019. Please refer to "Note 10 — Related
Party Transactions" for additional information regarding the AmTrust Reinsurance segment.

The  Company  evaluates  segment  performance  based  on  segment  profit  separately  from  the  results  of  our  investment  portfolio.  General  and  administrative
expenses  are  allocated  to  the  reportable  segments  on  an  actual  basis  except  salaries  and  benefits  where  management’s  judgment  is  applied;  however  general
corporate expenses are not allocated to the segments. In determining total assets by reportable segment, the Company identifies those assets that are attributable to
a particular segment such as reinsurance balances receivable, reinsurance recoverable on unpaid losses, deferred commission and other acquisition expenses, funds
withheld receivable, loan to related party, and restricted cash and investments. All remaining assets are allocated to Corporate.

The following tables summarize the underwriting results of our reportable segments and the reconciliation of our reportable segments' underwriting results to

consolidated net income:

For the Year Ended December 31, 2022
Gross premiums written
Net premiums written
Net premiums earned
Other insurance expense
Net loss and LAE
Commission and other acquisition expenses
General and administrative expenses

Underwriting loss
Reconciliation to net loss
Net investment income and net realized and unrealized losses on investment
Interest and amortization expenses
Foreign exchange and other gains, net
Other general and administrative expenses
Income tax expense
Interest in loss from equity method investments

Net loss

Diversified
Reinsurance

AmTrust Reinsurance

Total

$
$
$

$

24,017  $
23,620  $
27,983  $
(4,530)
(12,483)
(14,164)
(8,857)
(12,051) $

(18,538) $
(18,538) $
9,749  $
— 
(45,508)
(4,347)
(2,777)
(42,883)

$

F-16

5,479 
5,082 
37,732 
(4,530)
(57,991)
(18,511)
(11,634)

(54,934)

24,930 
(19,331)
8,255 
(19,313)
557 
(205)
(60,041)

 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

3. Segment Information (continued)

For the Year Ended December 31, 2021
Gross premiums written
Net premiums written
Net premiums earned
Other insurance revenue
Net loss and LAE
Commission and other acquisition expenses
General and administrative expenses

Underwriting income
Reconciliation to net income
Net investment income and net realized and unrealized gains on investment
Interest and amortization expenses
Foreign exchange and other gains, net
Other general and administrative expenses
Income tax expense
Interest in income from equity method investments

Net income

Diversified
Reinsurance

AmTrust Reinsurance

Total

$
$
$

$

16,633  $
16,098  $
27,681  $
1,067 
(4,286)
(15,093)
(7,827)
1,542  $

(5,695) $
(5,695) $
25,312  $
— 
(3,021)
(9,747)
(2,514)
10,030 

$

10,938 
10,403 
52,993 
1,067 
(7,307)
(24,840)
(10,341)

11,572 

44,661 
(19,327)
7,685 
(25,679)
(15)
7,748 
26,645 

F-17

 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

3. Segment Information (continued)

The  following  tables  summarize  the  financial  position  of  our  reportable  segments  including  the  reconciliation  to  the  Company's  consolidated  total  assets  at

December 31, 2022 and 2021:

December 31, 2022

Reinsurance balances receivable, net
Reinsurance recoverable on unpaid losses
Deferred commission and other acquisition expenses
Loan to related party
Restricted cash and cash equivalents and investments
Funds withheld receivable
Other assets
Total assets - reportable segments
Corporate assets

Total Assets

December 31, 2021

Reinsurance balances receivable, net
Reinsurance recoverable on unpaid losses
Deferred commission and other acquisition expenses
Loan to related party
Restricted cash and cash equivalents and investments
Funds withheld receivable
Other assets
Total assets - reportable segments
Corporate assets

Total Assets

Diversified
Reinsurance

AmTrust Reinsurance

Total

2,213  $
5,596 
1,344 
— 
61,223 
24,577 
2,337 
97,290 
— 
97,290  $

8,395  $

490,408 
23,632 
167,975 
235,607 
416,835 
— 
1,342,852 
— 

1,342,852  $

10,608 
496,004 
24,976 
167,975 
296,830 
441,412 
2,337 
1,440,142 
406,724 
1,846,866 

Diversified
Reinsurance

AmTrust Reinsurance

Total

1,927  $
2,979 
2,533 
— 
83,143 
34,952 
582 
126,116 
— 
126,116  $

17,471  $
490,860 
34,170 
167,975 
499,004 
601,460 
— 
1,810,940 
— 

1,810,940  $

19,398 
493,839 
36,703 
167,975 
582,147 
636,412 
582 
1,937,056 
385,554 
2,322,610 

$

$

$

$

The following table shows an analysis of gross and net premiums written and net premiums earned by geographic location for the years ended December 31,

2022 and 2021. In the case of reinsurance business assumed from AmTrust, the table refers to the location of the relevant AmTrust subsidiaries.

For the Year Ended December 31,
Gross premiums written – North America
Gross premiums written – Other (predominantly Europe)

Gross premiums written – Total
Net premiums written – North America
Net premiums written – Other (predominantly Europe)

Net premiums written – Total
Net premiums earned – North America
Net premiums earned – Other (predominantly Europe)

Net premiums earned – Total

F-18

2022

2021

$

$

$

$

$

$

(14,600) $
20,079 

5,479  $

(14,396) $
19,478 

5,082  $

(14,383) $
52,115 
37,732  $

(7,649)
18,587 
10,938 

(7,320)
17,723 
10,403 

(6,948)
59,941 
52,993 

 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

3. Segment Information (continued)

The  following  table  sets  forth  financial  information  relating  to  net  premiums  written  by  major  line  of  business  and  reportable  segment  for  the  years  ended

December 31, 2022 and 2021:

For the Year Ended December 31,
Diversified Reinsurance
International

Total Diversified Reinsurance

AmTrust Reinsurance
Small Commercial Business
Specialty Program
Specialty Risk and Extended Warranty

Total AmTrust Reinsurance

Total Net Premiums Written

2022

2021

$

$

23,620  $
23,620 

(15,143)
747 
(4,142)
(18,538)

5,082  $

16,098 
16,098 

(6,445)
(876)
1,626 
(5,695)
10,403 

The  following  table  sets  forth  financial  information  relating  to  net  premiums  earned  by  major  line  of  business  and  reportable  segment  for  the  years  ended

December 31, 2022 and 2021:

For the Year Ended December 31,

Diversified Reinsurance
International

Total Diversified Reinsurance

AmTrust Reinsurance
Small Commercial Business
Specialty Program
Specialty Risk and Extended Warranty

Total AmTrust Reinsurance

Total Net Premiums Earned

2022

2021

Total

% of Total

Total

% of Total

$

$

27,983 
27,983 

(15,131)
748 
24,132 
9,749 
37,732 

74.2 % $
74.2 %

(40.1)%
2.0 %
63.9 %
25.8 %
100.0 % $

27,681 
27,681 

(6,095)
(853)
32,260 
25,312 
52,993 

52.2 %
52.2 %

(11.5)%
(1.6)%
60.9 %
47.8 %
100.0 %

F-19

 
 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

4. Investments

As discussed in Note 2 — Significant Accounting Policies, the Company holds: (i) AFS portfolios of fixed maturity securities, carried at fair value; (ii) other
investments, of which certain investments are carried at fair value and investments in direct lending entities are carried at cost less impairment; (iii) equity method
investments; and (iv) funds held - directly managed.

a) Fixed Maturities

The amortized cost, gross unrealized gains and losses, and fair value of fixed maturities at December 31, 2022 and 2021 are as follows:

December 31, 2022
U.S. treasury bonds
U.S. agency bonds – mortgage-backed
Collateralized mortgage-backed securities
Non-U.S. government bonds
Collateralized loan obligations
Corporate bonds

Total fixed maturity investments

December 31, 2021
U.S. treasury bonds
U.S. agency bonds – mortgage-backed
Collateralized mortgage-backed securities
Non-U.S. government bonds
Collateralized loan obligations
Corporate bonds

Total fixed maturity investments

Original or 
amortized cost

Gross 
unrealized gains

Gross 
unrealized losses

Fair value

55,647  $
38,767 
7,199 
12,643 
119,120 
97,063 
330,439  $

1  $

— 
— 
— 
— 
— 

1  $

(116) $

(4,402)
(432)
(825)
(5,028)
(5,110)
(15,913) $

55,532 
34,365 
6,767 
11,818 
114,092 
91,953 
314,527 

Original or 
amortized cost

Gross 
unrealized gains

Gross 
unrealized losses

Fair value

59,989  $
96,554 
14,972 
3,163 
183,974 
236,692 
595,344  $

—  $

2,429 
565 
113 
140 
10,094 
13,341  $

(110) $
(193)
— 
— 
(5,093)
(6,144)
(11,540) $

59,879 
98,790 
15,537 
3,276 
179,021 
240,642 
597,145 

$

$

$

$

The contractual maturities of our fixed maturities are shown below. Actual maturities may differ from contractual maturities because borrowers may have the

right to call or prepay obligations with or without call or prepayment penalties.

December 31, 2022

Maturity

Due in one year or less
Due after one year through five years
Due after five years through ten years

U.S. agency bonds – mortgage-backed
Collateralized mortgage-backed securities
Collateralized loan obligations

Total fixed maturities

F-20

Fixed maturities

Amortized cost

Fair value

$

$

72,870  $
76,439 
16,044 
165,353 
38,767 
7,199 
119,120 
330,439  $

72,571 
72,883 
13,849 
159,303 
34,365 
6,767 
114,092 
314,527 

 
 
 
 
 
 
 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

4. Investments (continued)

The following tables summarize fixed maturities in an unrealized loss position and the aggregate fair value and gross unrealized loss by length of time the

security has continuously been in an unrealized loss position:

December 31, 2022
U.S. treasury bonds
U.S. agency bonds – mortgage-backed
Collateralized mortgage-backed securities
Non-U.S. government bonds
Collateralized loan obligations
Corporate bonds

$

Total temporarily impaired fixed maturity securities $

Less than 12 Months

12 Months or More

Total

Fair 
value

Unrealized 
losses

Fair 
value

Unrealized 
losses

Fair 
value

Unrealized 
losses

53,094  $
31,394 
6,768 
11,818 
17,959 
87,212 
208,245  $

(114) $

(3,697)
(432)
(825)
(1,032)
(4,325)
(10,425) $

148  $

2,971 
— 
— 
96,133 
4,740 
103,992  $

(2) $

(705)
— 
— 
(3,996)
(785)
(5,488) $

53,242  $
34,365 
6,768 
11,818 
114,092 
91,952 
312,237  $

(116)
(4,402)
(432)
(825)
(5,028)
(5,110)
(15,913)

At  December  31,  2022,  there  were  88  securities  in  an  unrealized  loss  position  with  a  fair  value  of  $312,237  and  unrealized  losses  of  $15,913.  Of  these
securities in an unrealized loss position, there were 26 securities in our portfolio that have been in an unrealized loss position for twelve months or greater with a
fair value of $103,992 and unrealized losses of $5,488.

December 31, 2021
U.S. treasury bonds
U.S. agency bonds – mortgage-backed
Collateralized loan obligations
Corporate bonds

Total temporarily impaired fixed maturity
securities

Less than 12 Months

12 Months or More

Total

Fair 
value

Unrealized 
losses

Fair 
value

Unrealized 
losses

Fair 
value

Unrealized 
losses

$

59,879  $
4,415 
117,148 
38,537 

(110) $
(193)
(5,057)
(2,775)

—  $
— 
5,064 
27,852 

—  $
— 
(36)
(3,369)

59,879  $
4,415 
122,212 
66,389 

(110)
(193)
(5,093)
(6,144)

$

219,979  $

(8,135) $

32,916  $

(3,405) $

252,895  $

(11,540)

At  December  31,  2021,  there  were  44  securities  in  an  unrealized  loss  position  with  a  fair  value  of  $252,895  and  unrealized  losses  of  $11,540.  Of  these
securities in an unrealized loss position, there were 8 securities in our portfolio that have been in an unrealized loss position for twelve months or greater with a
fair value of $32,916 and unrealized losses of $3,405.

OTTI

The  Company  performs  quarterly  reviews  of  its  fixed  maturities  in  order  to  determine  whether  declines  in  fair  value  below  the  amortized  cost  basis  were
considered other-than-temporary in accordance with applicable guidance. At December 31, 2022, we determined that unrealized losses on fixed maturities were
primarily  due  to  changes  in  interest  rates  since  their  date  of  purchase.  All  fixed  maturity  securities  continue  to  pay  the  expected  coupon  payments  under  the
contractual terms of the securities. Any credit-related impairment related to fixed maturity securities that the Company does not intend to sell or is not more likely
than not that the Company will be required to sell before its anticipated recovery of their amortized cost basis is recognized in net income, with the non-credit
related impairment recognized in comprehensive income.

Based on the Company's analysis, our fixed maturity portfolio is of high credit quality and we believe the amortized cost basis of the securities will ultimately
be recovered. The Company continually monitors the credit quality of the fixed maturity investments to assess if it is probable that it will receive the contractual or
estimated  cash  flows  in  the  form  of  principal  and  interest.  For  the  years  ended  December  31,  2022  and  2021,  there  was  no  impairment  recognized  on  the
Company's portfolio of fixed maturity securities.

F-21

 
 
 
 
 
 
 
 
 
 
 
 
 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

4. Investments (continued)

The following tables summarize the credit ratings of our fixed maturity securities as at December 31, 2022 and 2021:

December 31, 2022
U.S. treasury bonds
U.S. agency bonds
AAA
AA+, AA, AA-
A+, A, A-
BBB+, BBB, BBB-
BB+ or lower

Total fixed maturities

(1)

December 31, 2021
U.S. treasury bonds
U.S. agency bonds
AAA
AA+, AA, AA-
A+, A, A-
BBB+, BBB, BBB-
BB+ or lower

Total fixed maturities

(1)

(1)    

Based on Standard & Poor’s ("S&P"), or equivalent, ratings

Amortized cost

Fair value

% of Total 
fair value

55,647  $
38,767 
112,775 
23,974 
38,549 
55,374 
5,353 
330,439  $

55,532 
34,365 
108,136 
22,640 
35,996 
53,094 
4,764 
314,527 

17.7 %
10.9 %
34.4 %
7.2 %
11.4 %
16.9 %
1.5 %
100.0 %

Amortized cost

Fair value

% of Total 
fair value

59,989  $
96,554 
161,179 
38,999 
99,748 
126,770 
12,105 
595,344  $

59,879 
98,790 
156,706 
39,140 
99,962 
129,618 
13,050 
597,145 

10.0 %
16.6 %
26.2 %
6.6 %
16.7 %
21.7 %
2.2 %
100.0 %

$

$

$

$

b) Other Investments, Equity Securities and Equity Method Investments

Certain  of  the  Company's  other  investments  and  equity  method  investments  are  subject  to  restrictions  on  redemptions  and  sales  that  are  determined  by  the
governing  documents,  which  could  limit  our  ability  to  liquidate  those  investments.  These  restrictions  may  include  lock-ups,  redemption  gates,  restricted  share
classes, restrictions on the frequency of redemption and notice periods. A gate is the ability to deny or delay a redemption request. Certain other investments and
equity method investments may not have any restrictions governing their sale, but there is no active market and no assurance that we will be able to execute a sale
in  a  timely  manner.  In  addition,  even  if  certain  other  investments  and  equity  method  investments  are  not  eligible  for  redemption  or  sales  are  restricted,  the
Company may still receive income distributions from those investments.

Other investments

The table below shows the composition of the Company's other investments as at December 31, 2022 and 2021:

December 31,

Privately held equity investments
Private credit funds
Private equity funds
Total other investments at fair value
Investments in direct lending entities (at cost)

Total other investments

2022

2021

Carrying Value

% of Total

Carrying Value

% of Total

$

$

34,014 
24,374 
34,278 
92,666 
56,087 
148,753 

22.9 % $
16.4 %
23.0 %
62.3 %
37.7 %
100.0 % $

30,500 
20,922 
23,324 
74,746 
42,976 
117,722 

25.9 %
17.8 %
19.8 %
63.5 %
36.5 %
100.0 %

The Company's investments in direct lending entities of $56,087 at December 31, 2022 (2021 - $42,976) are carried at cost less impairment, if any, with any
indication of impairment recognized in net income when determined. No impairment was recognized for the year ended December 31, 2022 and 2021. Please see
"Note 5(d) - Fair Value Measurements" for additional information regarding this investment.

F-22

 
 
 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

4. Investments (continued)

Equity Securities

Equity securities include publicly traded equity investments in common stocks and privately held equity investments in common and preferred stocks. The
Company's publicly traded equity investments in common stocks trade on major exchanges. The Company's privately held equity investments in common and
preferred  stocks  are  direct  investments  in  companies  that  the  Company  believes  offer  attractive  risk  adjusted  returns  or  offer  other  strategic  advantages.  Each
investment  may  have  its  own  unique  terms  and  conditions  and  there  may  be  restrictions  on  disposals.  There  is  no  active  market  for  these  investments.  The
following table provides the cost and fair values of the equity securities held at December 31, 2022 and 2021:

December 31,

Publicly traded equity investments in common stocks
Privately held common stocks
Privately held preferred stocks

Total equity securities

Equity Method Investments

2022

2021

Cost

Fair Value

Cost

Fair Value

$

$

559  $

32,775 
7,175 
40,509  $

386  $

32,290 
10,945 
43,621  $

559  $

21,869 
800 
23,228  $

1,174 
22,029 
800 
24,003 

The equity method investments include real estate investments, hedge fund investments and other investments. The table below shows the carrying value of the

Company's equity method investments as of December 31, 2022 and 2021:

December 31,

Real estate investments
Hedge fund investments
Other investments

Total equity method investments

2022

2021

Carrying Value

% of Total

Carrying Value

% of Total

$

$

40,944 
5,376 
33,839 
80,159 

51.1 % $
6.7 %
42.2 %
100.0 % $

44,050 
32,929 
6,763 
83,742 

52.6 %
39.3 %
8.1 %
100.0 %

The equity method investments above include limited partnerships which are variable interests issued by variable interest entities ("VIEs"). The Company does
not  have  the  power  to  direct  the  activities  that  are  most  significant  to  the  economic  performance  of  these  VIEs,  therefore,  the  Company  is  not  the  primary
beneficiary  of  these  VIEs.  The  Company  is  deemed  to  have  limited  influence  over  the  operating  and  financial  policies  of  the  investee  and  accordingly,  these
investments are reported under the equity method of accounting. In applying the equity method of accounting, the investments are initially recorded at cost and are
subsequently  adjusted  based  on  the  Company’s  proportionate  share  of  the  investee's  net  income  or  loss.  Generally,  the  maximum  exposure  to  loss  on  these
interests is limited to the amount of commitment made by the Company as more fully described in "Note 11 - Commitments, Contingencies and Guarantees" in
these consolidated financial statements.

c) Net Investment Income

Net investment income was derived from the following sources for the years ended December 31, 2022 and 2021:

For the Year Ended December 31,
Fixed maturities
Income on funds withheld
Interest income from loan to related party
Cash and cash equivalents and other investments

Investment expenses

Net investment income

2022

2021

$

$

9,736  $
11,117 
6,202 
3,415 
30,470 
(400)
30,070  $

19,146 
10,623 
3,492 
1,100 
34,361 
(2,348)
32,013 

d) Net Realized and Unrealized Investment Gains (Losses)

Realized gains or losses on the sale of investments are determined on the basis of the first in first out cost method. The following tables show the net realized

and unrealized investment gains (losses) included in the Consolidated Statements of Income for the years ended December 31, 2022 and 2021:

F-23

 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

4. Investments (continued)

For the Year Ended December 31, 2022
Fixed maturities
Equity securities
Other investments

Net realized and unrealized investment gains (losses)

For the Year Ended December 31, 2021
Fixed maturities
Equity securities
Other investments

Net realized and unrealized investment gains (losses)

Gross gains

Gross losses

Net

$

$

1,829  $
3,770 
1,543 
7,142  $

(4,812) $
(1,434)
(6,036)
(12,282) $

(

(
(

Gross gains

Gross losses

Net

$

$

9,838  $
5,168 
3,002 
18,008  $

(741) $

(4,392)
(227)
(5,360) $

9,097 
776 
2,775 
12,648 

Realized  and  unrealized  investment  gains  and  losses  from  equity  securities  detailed  above  include  both  sales  of  equity  securities  and  unrealized  gains  and
losses stemming from fair value changes. The unrealized gains recognized in net income for investments still held at December 31, 2022 and 2021, respectively,
were as follows:

For the Year Ended December 31,
Net gains recognized for equity securities
Net gains recognized for equity securities divested

Net unrealized gains recognized for equity securities still held at reporting date

2022

2021

$

$

2,336  $
(111)
2,225  $

776 
(441)
335 

Proceeds from sales of fixed maturities were $213,944 and $477,920 for the years ended December 31, 2022, and 2021, respectively. Net unrealized gains

(losses) included in AOCI were as follows at December 31, 2022 and 2021, respectively:

December 31,
Fixed maturity investments
Equity method investments
Total net unrealized losses
Deferred income tax

Net unrealized losses, net of deferred income tax
Change in net unrealized losses, net of deferred income tax

e) Restricted Cash and Cash Equivalents and Investments

2022

2021

$

$

$

(15,912) $
— 
(15,912)
244 
(15,668) $

(12,975) $

1,801 
(4,414)
(2,613)
(80)
(2,693)

(52,050)

The Company is required to provide collateral for its reinsurance liabilities under various reinsurance agreements and utilizes trust accounts to collateralize
business with reinsurance counterparties. The assets in trust as collateral are primarily cash and highly rated fixed maturities. The fair values of restricted assets
were as follows at December 31, 2022 and 2021:

December 31,
Restricted cash – third party agreements
Restricted cash – related party agreements
Total restricted cash
Restricted investments – in trust for third party agreements at fair value (amortized cost: 2022 – $48,181; 2021 –
 $48,860)
Restricted investments – in trust for related party agreements at fair value (amortized cost: 2022 – $246,325; 2021 –
 $493,128)
Total restricted investments

Total restricted cash and investments

2022

2021

$

$

13,122  $
2,516 
15,638 

48,101 

233,091 
281,192 
296,830  $

19,177 
20,242 
39,419 

48,845 

493,883 
542,728 
582,147 

F-24

 
 
 
 
 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

5. Fair Value Measurements

a) Fair Values of Financial Instruments measured at fair value

ASC 825, "Disclosure About Fair Value of Financial Instruments", requires all entities to disclose the fair value of their financial instruments for both assets
and liabilities recognized and not recognized within the balance sheet, and for which it is practicable to estimate fair value. The following describes the valuation
techniques used by the Company to determine the fair value of financial instruments measured at fair value held at December 31, 2022 and 2021.

U.S. government and U.S. agency bonds — Bonds issued by the U.S. Treasury, the Federal Home Loan Bank, the Federal Home Loan Mortgage Corporation,
Government National Mortgage Association, Federal National Mortgage Association and the Federal Farm Credit Banks Funding Corporation. The fair values of
U.S. treasury bonds are based on quoted market prices in active markets, and are included in the Level 1 fair value hierarchy. We believe the market for U.S.
treasury bonds is an actively traded market given the high level of daily trading volume. The fair values of U.S. agency bonds are determined using the spread
above the risk-free yield curve. As the yields for the risk-free yield curve and the spreads for these securities are observable market inputs, the fair values of U.S.
agency bonds are included in the Level 2 fair value hierarchy.

Non-U.S. government bonds — These securities are generally priced by independent pricing services. The Pricing Service may use current market trades for
securities with similar quality, maturity and coupon. If no such trades are available, the Pricing Service typically uses analytical models which may incorporate
spreads, interest rate data and market/sector news. As the significant inputs used to price non-U.S. government bonds are observable market inputs, the fair values
of non-U.S. government and bonds are included in the Level 2 fair value hierarchy.

Collateralized  loan  obligations  ("CLO")  -  These  asset  backed  securities  are  originated  by  a  variety  of  financial  institutions  that  on  acquisition  are  rated
BBB-/Baa3 or higher. These securities are priced by independent pricing services and brokers. The pricing provider applies dealer quotes and other available trade
information, prepayment speeds, yield curves and credit spreads to the valuation. As the significant inputs used to price the CLO are observable market inputs, the
fair values are included in the Level 2 fair value hierarchy.

Commercial mortgage-backed securities ("CMBS") - These asset backed securities are originated by a variety of financial institutions that on acquisition are
rated BBB-/Baa3 or higher. These securities are priced by independent pricing services and brokers. The pricing provider applies dealer quotes and other available
trade information, prepayment speeds, yield curves and credit spreads to the valuation. As the significant inputs used to price the CMBS are observable market
inputs, the fair values are included in the Level 2 fair value hierarchy.

Corporate and municipal bonds — Bonds issued by corporations, U.S. state and municipality entities or agencies. that on acquisition are rated BBB-/Baa3 or
higher.  These  securities  are  generally  priced  by  independent  pricing  services.  The  credit  spreads  are  sourced  from  broker/dealers,  trade  prices  and  new  issue
market. Where pricing is unavailable from pricing services, custodian pricing or non-binding quotes are obtained from broker-dealers to estimate fair values. As
significant inputs used to price corporate and municipal bonds are observable market inputs, fair values are included in the Level 2 fair value hierarchy.

Equity securities - Equity securities include publicly traded common and preferred stocks, and privately held common and preferred stocks. The fair value of
publicly traded common and preferred stocks is primarily priced by pricing services, reflecting the closing price quoted for the final trading day of the period.
These investments are carried at fair value using observable market pricing data and is included in the Level 1 fair value hierarchy. Any unrealized gains or losses
on  the  investment  is  recorded  in  net  income  in  the  reporting  period  in  which  it  occurs.  The  privately  held  common  and  preferred  stocks  are  valued  using
significant inputs that are unobservable where there is little or no market activity. Unadjusted third party pricing sources or management's assumptions and internal
valuation models may be used to determine the fair values, therefore, these investments are classified as Level 3 in the fair value hierarchy.

Other investments — These investments are comprised of the following types of investments:

•Privately held investments: These are direct equity investments in common and preferred shares of privately held entities. The fair values are estimated
using  quarterly  financial  statements  and/or  recent  private  market  transactions  and  thus  included  under  Level  3  of  the  fair  value  hierarchy  due  to
unobservable market data used for valuation.

•Private credit funds: These are privately held equity investments in common stock of entities that lend money valued using the most recently available or
quarterly  NAV  statements  as  provided  by  the  external  fund  manager  or  third-party  administrator  and  therefore  measured  using  the  NAV  as  a  practical
expedient.

•Private equity funds: These are comprised of private equity funds, private equity co-investments with sponsoring entities and investments in real estate
limited partnerships and joint ventures. The fair value is estimated based on the most recently available NAV as advised by the external fund manager or
third-party administrator. The fair values are therefore measured using the NAV as a practical expedient.

Derivative  Instruments  -  The  Company  has  recently  entered  into  retroactive  reinsurance  contracts  that  are  accounted  for  as  derivatives.  These  reinsurance
contracts  provide  indemnification  to  an  insured  or  cedant  as  a  result  of  a  change  in  a  variable  as  opposed  to  an  identifiable  insurable  event.  The  Company
considers  these  contracts  to  be  part  of  its  underwriting  operations.  The  derivatives  are  initially  valued  at  cost  which  approximates  fair  value.  In  subsequent
measurement periods, the fair values of these derivatives are determined using internally developed discounted cash flow models using appropriate discount rates.
The selection of an appropriate discount rate is judgmental and is the most significant unobservable input used in the valuation of these derivatives.

F-25

 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

5. Fair Value Measurements (continued)

The  fair  value  changes  in  underwriting-related  derivative  instruments  is  included  within  other  insurance  revenue  (expense),  net.  The  derivative  liability  on
retroactive reinsurance is presented as part of accrued expenses and other liabilities. A  significant  increase  (decrease)  in  this  input  in  isolation  may  result  in  a
significantly lower (higher) fair value measurement for the derivative contract. As the significant inputs used to price these derivatives are unobservable, the fair
values of these contracts are classified as Level 3 in the fair value hierarchy.

b) Fair Value Hierarchy

The Company’s estimates of fair value for its financial assets and financial liabilities are based on the framework established in ASC 820. The framework is
based on the inputs used in valuation and gives the highest priority to quoted prices in active markets and requires that observable inputs be used in the valuation
methodology whenever available. In determining the level of the hierarchy in which the estimate is disclosed, the highest priority is given to unadjusted quoted
prices in active trading markets and the lowest priority to unobservable inputs that reflect significant market assumptions.

At  December  31,  2022  and  2021,  the  Company  classified  its  financial  instruments  measured  at  fair  value  on  a  recurring  basis  in  the  following  valuation

hierarchy:

December 31, 2022
Fixed maturities
U.S. treasury bonds
U.S. agency bonds – mortgage-backed
Collateralized mortgage-backed bonds
Non-U.S. government bonds
Collateralized loan obligations
Corporate bonds
Equity securities
Other investments

Total
As a percentage of total assets

Underwriting-related derivative liability

December 31, 2021
Fixed maturities
U.S. treasury bonds
U.S. agency bonds – mortgage-backed
Collateralized mortgage-backed bonds
Non-U.S. government bonds
Collateralized loan obligations
Corporate bonds
Equity investments
Other investments

Total

Quoted Prices 
in Active 
Markets for Identical
Assets 
(Level 1)

Significant 
Other 
Observable 
Inputs 
(Level 2)

Significant 
Unobservable 
Inputs 
(Level 3)

Fair Value Based on
NAV Practical
Expedient

Total Fair 
Value

$

$

$

$

$

55,532 
— 
— 
— 
— 
— 
386 
— 
55,918 

3.0 %

— 

Quoted Prices 
in Active 
Markets for 
Identical Assets 
(Level 1)

59,879 
— 
— 
— 
— 
— 
1,174 
— 
61,053 

$

$

$

$

$

— 
34,365 
6,767 
11,818 
114,092 
91,953 
— 
1,000 
259,995 

14.1 %

— 

Significant 
Other 
Observable 
Inputs 
(Level 2)

— 
98,790 
15,537 
3,276 
179,021 
240,642 
— 
— 
537,266 

$

$

$

$

$

— 
— 
— 
— 
— 
— 
17,806 
1,000 
18,806 

1.0 %

14,559 

$

$

$

— 
— 
— 
— 
— 
— 
25,429 
90,666 
116,095 

6.3 %

— 

Significant 
Unobservable 
Inputs 
(Level 3)

Fair Value Based on
NAV Practical
Expedient

— 
— 
— 
— 
— 
— 
5,094 
2,000 
7,094 

$

$

— 
— 
— 
— 
— 
— 
17,735 
72,746 
90,481 

$

$

$

$

$

55,532 
34,365 
6,767 
11,818 
114,092 
91,953 
43,621 
92,666 
450,814 

24.4 %

14,559 

Total Fair 
Value

59,879 
98,790 
15,537 
3,276 
179,021 
240,642 
24,003 
74,746 
695,894 

As a percentage of total assets

2.6 %

23.1 %

0.3 %

3.9 %

29.9 %

The Company utilizes the Pricing Service to assist in determining the fair value of its investments; however, management is ultimately responsible for all fair
values  presented  in  the  Company’s  financial  statements.  This  includes  responsibility  for  monitoring  the  fair  value  process,  ensuring  objective  and  reliable
valuation practices, and pricing of assets and liabilities and use of pricing sources. The Company analyzes and reviews the information and prices received from
the Pricing Service to ensure that the prices provided represent a reasonable estimate of fair value.

F-26

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

5. Fair Value Measurements (continued)

The  Pricing  Service  was  utilized  to  estimate  fair  value  measurements  for  98.5%  and  99.0%  of  our  fixed  maturities  at  December  31,  2022  and  2021,
respectively. The Pricing Service utilizes market quotations for fixed maturity securities that have quoted market prices in active markets. Since fixed maturities
other than U.S. treasury bonds generally do not trade actively on a daily basis, the Pricing Service prepares estimates of fair value measurements using relevant
market data, benchmark curves, sector groupings and matrix pricing and these have been classified as Level 2 within the fair value hierarchy.

At December 31, 2022 and 2021, approximately 1.5% and 1.0%, respectively, of our fixed maturities were valued using the market approach. At December 31,
2022, one security or $4,764 (2021 - one security or $6,225) of fixed maturities classified as Level 2 was priced using a quotation from a broker and/or custodian
as opposed to the Pricing Service due to lack of information available. At December 31, 2022 and 2021, the Company has not adjusted any pricing provided to it
based on the review performed by its investment managers.

During  the  year  ended  December  31,  2021,  the  Company  transferred  its  equity  investment  in  an  insurtech  start-up  company  focused  on  technological
advancement in the automobile insurance industry out of Level 3 within the fair value hierarchy and into Level 1 due to the recent completion of its initial public
offering. There were no transfers to or from Level 3 during the year ended December 31, 2022.

c) Level 3 Financial Instruments

At December 31, 2022, the Company holds Level 3 financial instruments which include privately held equity investments of $18,806 (2021 - $7,094) which
are included in total investments and an underwriting-related derivative liability of $14,559 on a reinsurance contract written by GLS which is included in accrued
expenses and other liabilities.

The  fair  value  of  privately  held  equity  securities  are  estimated  using  quarterly  unaudited  capital  or  financial  statements  provided  by  the  investee  or  recent
private market transactions, where applicable. Any changes to the financial information provided by the investee could result in a significantly higher or lower
valuation  at  the  reporting  date.  The  fair  value  of  underwriting-related  derivative  instruments  is  determined  using  a  discounted  cash  flow  model  in  which  the
Company examines current market conditions, historical results as well as contract specific information that may impact future cash flows in order to assess the
reasonableness of inputs used in the valuation model. Due to significant unobservable inputs in these valuations, the Company classifies the fair values as Level 3
within the fair value hierarchy.

The following table provides a summary of quantitative information regarding the significant unobservable inputs used in determining the fair value of other

investments measured at fair value on a recurring basis under the Level 3 classification at December 31, 2022:

Fair Value

Valuation Technique

Unobservable Inputs

Range of Unobservable
Inputs

Privately held equity securities - common

shares

Privately held equity securities - preferred

shares

Total Level 3 investments

Underwriting-related derivative liability

$

$

$

6,861 

11,945 
18,806 

14,559 

Quarterly financial
statements

Quarterly financial
statements

Price/book ratios of comparable public
companies

Privately calculated enterprise
valuations

Discounted cash flows

Duration matched discount rates

2.0%

to

3.0%

The following table shows the reconciliation of the beginning and ending balances for other investments measured at fair value on a recurring basis using Level
3 inputs for the years ended December 31, 2022 and 2021. The Company includes any related interest and dividend income in net investment income and thus, are
excluded from the reconciliation in the table below:

For the Year Ended December 31,
Balance - beginning of period
Sales
Net unrealized gains recognized in the statement of income
Purchases
Transfers out of Level 3

Total Level 3 investments - end of period

2022

2021

$

$

7,094  $
(2,000)
3,770 
9,942 
— 
18,806  $

2,844 
— 
— 
5,250 
(1,000)
7,094 

F-27

 
 
 
 
 
 
 
 
 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

5. Fair Value Measurements (continued)

d) Financial Instruments Disclosed, But Not Carried, at Fair Value

The  fair  value  of  financial  instruments  accounting  guidance  also  applies  to  financial  instruments  disclosed,  but  not  carried  at  fair  value,  except  for  certain

financial instruments related to insurance contracts.

At  December  31,  2022,  the  carrying  values  of  cash  and  cash  equivalents  (including  restricted  amounts),  accrued  investment  income,  reinsurance  balances
receivable,  loan  to  related  party  and  certain  other  assets  and  liabilities  approximate  their  fair  values  due  to  their  inherent  short  duration.  As  these  financial
instruments are not actively traded, the fair values of these financial instruments are classified as Level 2.

The investments made by direct lending entities are carried at cost less impairment, if any, which approximates fair value. The fair value estimates of these

investments are not based on observable market data and, as a result, have been categorized as Level 3.

The fair values of the Senior Notes (as defined in Note 7 — Long-Term Debt) are based on indicative market pricing obtained from a third-party pricing service
which uses observable market inputs, and therefore the fair values of these liabilities are classified as Level 2. The following table presents the respective carrying
value and fair value for the Senior Notes as at December 31, 2022 and 2021:

December 31,

2016 Senior Notes – 6.625%

2013 Senior Notes – 7.75%

Total Senior Notes

6. Shareholders’ Equity

2022

2021

Carrying Value

Fair Value

Carrying Value

Fair Value

$

$

110,000  $

76,560  $

110,000  $

152,500 
262,500  $

113,826 
190,386  $

152,500 
262,500  $

94,820 

140,300 
235,120 

At December 31, 2022, the aggregate authorized share capital of the Company is 150,000,000 shares from which 149,224,080 common shares were issued, of
which 101,532,151 common shares are outstanding, and 47,691,929 shares are treasury shares. Included in treasury shares are 41,439,348 common shares issued
to Maiden Reinsurance in the Exchange which are not treated as outstanding shares on the Consolidated Balance Sheet on December 31, 2022.

The remaining 775,920 shares are undesignated at December 31, 2022. At December 31, 2022, 492,463 common shares will be issued and outstanding upon

vesting of restricted shares.

a) Common shares

The Company's common shares have a par value of $0.01 per share. Our common shareholders are entitled to receive dividends and allocated one vote per
common share subject to downward adjustment under certain circumstances. For the years ended December 31, 2022 and 2021, the Company's Board of Directors
did not declare any dividends to common shareholders.

The following table shows the summary of changes in the Company's common shares outstanding for the years ended December 31, 2022 and 2021:

For the Year Ended December 31,
Outstanding shares – January 1
Shares issued pursuant to the Exchange
Issuance of vested restricted shares and exercised common share options
Shares repurchased for tax purposes
Less: Common shares held by Maiden Reinsurance as treasury shares
(1)

Outstanding shares – December 31

2022
86,467,242 
55,800,000 
1,107,973 
(403,716)
(41,439,348)
101,532,151 

2021
84,801,16
—
2,500,932
(834,851
—
86,467,242

(1) Outstanding shares at December 31, 2022 exclude 41,439,348 common shares issued to Maiden Reinsurance in exchange for the preference shares previously held which are reflected as treasury

shares on the Consolidated Balance Sheet and are not treated as outstanding common shares.

b) Preference shares

Exchange of Preference Shares

On December 27, 2022, the Company completed the Exchange, as fully described in "Note 1. Organization", with record holders of the Series A, C and D

Preference Shares. The Company offered three common shares as consideration for each share of the Series A, C and D Preferred Shares tendered.

F-28

 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

6. Shareholders’ Equity (continued)

A total of 1,500,050 shares of Series A Preference Shares, 1,744,028 shares of Series C Preference Shares, and 1,542,806 shares of Series D Preference Shares
were  accepted,  resulting  in  the  issuance  of  14,360,652  common  shares  to  non-affiliates  at  a  fair  value  of  $28,434.  The  Exchange  was  accounted  for  as  an
extinguishment resulting in derecognition of the $119,672 carrying amount of Series A, C and D Preference Shares tendered, elimination of $3,998 of original
issuance costs, recognition of the $25,915 excess of the fair value of the common shares issued over par value, net of $2,375 issuance costs, as additional paid in
capital, and recognition of the $87,240 excess of the carrying amount of the Preference Shares extinguished over the fair value of the common shares issued as an
increase to retained earnings.

The number of the Company's Series A, C and D Preference Shares held by Maiden Reinsurance pursuant to the 2020 Tender Offer and the 2021 Preference
Share Repurchase Program was 13,813,116 at the Exchange Date. Therefore, 41,439,348 common shares were issued to Maiden Reinsurance in exchange for the
Preference  Shares  held  which  are  reflected  as  treasury  shares  on  the  Consolidated  Balance  Sheet  and  are  not  treated  as  outstanding  common  shares  on
December 31, 2022.

As a result of the Exchange, the Preference Shares were delisted from and no longer trade on the New York Stock Exchange as of the Exchange Date. No
Preference Shares are issued or outstanding, and the Preference Shares were deregistered under the Securities Exchange Act of 1934, as amended. In addition, all
rights of the former holders related to ownership of the Preference Shares have terminated.

Prior to the Exchange, on March 3, 2021 and May 6, 2021, the Company's Board of Directors approved the repurchase, including the repurchase by Maiden
Reinsurance in accordance with its investment guidelines, of up to $100,000 and $50,000, respectively, of the Company's preference shares from time to time at
market  prices  in  open  market  purchases  or  as  may  be  privately  negotiated.  The  authorizations  are  collectively  referred  to  as  the  "2021  Preference  Share
Repurchase Program". The following table shows the summary of the Company's preference shares repurchases made during the years ended December 31, 2022
and 2021:

For the Year Ended December 31,

2022

2021

Series A
Series C
Series D

Total

Number of shares
purchased

Average price of shares
purchased

Number of shares
purchased

Average price of shares
purchased

435,639  $
625,742 
520,128 
1,581,509 

5.27 
7.08 
6.26 

6.31 

3,519,093  $
3,026,764 
2,858,155 
9,404,012 

14.74 
14.36 
14.27 

14.48 

Total price paid for preference shares

Gain on purchase of preference shares

$

$

9,983 

28,233 

$

$

136,155 

90,998 

The following table shows the Company's preference shares (including the total preference shares previously held by Maiden Reinsurance pursuant to the 2020

Tender Offer and the 2021 Preference Share Repurchase Program) prior to the Exchange that occurred on December 27, 2022:

Outstanding shares issued by Maiden Holdings
Less: Total shares previously held by Maiden Reinsurance

Total shares previously held by non-affiliates
Percentage previously held by Maiden Reinsurance

c) Treasury Shares

Series A

Series C

Series D

6,000,000 
4,499,950 
1,500,050 

6,600,000 
4,855,972 
1,744,028 

6,000,000 
4,457,194 
1,542,806 

Total
18,600,000 
13,813,116 
4,786,884 

75.0 %

73.6 %

74.3 %

74.3 %

On February 21, 2017, the Company's Board of Directors approved the repurchase of up to $100,000 of the Company's common shares from time to time at
market  prices.  At  December  31,  2022  and  2021,  the  Company  has  a  remaining  authorization  of  $74,245  for  common  share  repurchases.  No  repurchases  were
made during the years ended December 31, 2022 and 2021 under the common share repurchase plan.

During the year ended December 31, 2022, the Company repurchased 403,716 (2021 - 834,851) common shares at an average price per share of $2.50 (2021 -
$2.97)  from  employees  which  represent  tax  withholding  in  respect  of  tax  obligations  on  the  vesting  of  both  non-performance-based  and  discretionary
performance-based restricted shares.

The  41,439,348  common  shares  issued  to  Maiden  Reinsurance  as  part  of  the  Exchange  are  reflected  as  treasury  shares  and  are  not  treated  as  outstanding

common shares at December 31, 2022.

F-29

 
 
 
 
 
 
 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

6. Shareholders’ Equity (continued)

The table below includes the total number of treasury shares outstanding at December 31, 2022 and 2021:

December 31,
Number of treasury shares held by Maiden Reinsurance due to the Exchange
Number of treasury shares due to common share repurchases for tax purposes

Total number of treasury shares at the end of the reporting period

d) Accumulated Other Comprehensive Income (Loss)

2022
41,439,348
6,252,581
47,691,929

2021

—
5,848,865
5,848,865

The following tables set forth financial information regarding the changes in the balances of each component of AOCI for the years ended December 31, 2022

and 2021:

For the Year Ended December 31, 2022
Beginning balance
Other comprehensive loss before reclassifications
Amounts reclassified from AOCI to net income, net of tax
Net current period other comprehensive loss

Ending balance, Maiden shareholders

For the Year Ended December 31, 2021
Beginning balance
Other comprehensive (loss) income before reclassifications
Amounts reclassified from AOCI to net income, net of tax
Net current period other comprehensive (loss) income

Ending balance, Maiden shareholders

Change in net
unrealized gains on
investment

Foreign currency
translation adjustments

Total

(2,693) $
(6,168)
(6,807)
(12,975)
(15,668) $

(9,522) $
(16,044)
— 
(16,044)
(25,566) $

(12,215)
(22,212)
(6,807)
(29,019)
(41,234)

Change in net
unrealized gains on
investment

Foreign currency
translation adjustments

Total

49,357  $
(33,263)
(18,787)
(52,050)
(2,693) $

(25,500) $
15,978 
— 
15,978 
(9,522) $

23,857 
(17,285)
(18,787)
(36,072)
(12,215)

$

$

$

$

F-30

 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

7. Long-Term Debt

Senior Notes

At December 31, 2022 and 2021, Maiden Holdings had outstanding publicly-traded senior notes which were issued in 2016 ("2016 Senior Notes") and its
wholly owned subsidiary, Maiden Holdings North America, Ltd. ("Maiden NA") had outstanding publicly-traded senior notes which were issued in 2013 ("2013
Senior  Notes"(collectively  "Senior  Notes").  The  2013  Senior  Notes  issued  by  Maiden  NA  are  fully  and  unconditionally  guaranteed  by  Maiden  Holdings.  The
Senior Notes are unsecured and unsubordinated obligations of the Company.

The following tables detail the issuances outstanding at December 31, 2022 and 2021:

December 31, 2022
Principal amount
Less: unamortized issuance costs

Carrying value

December 31, 2021
Principal amount
Less: unamortized issuance costs

Carrying value

Other details:
Original debt issuance costs
Maturity date
Earliest redeemable date (for cash)
Coupon rate
Effective interest rate

2016 Senior Notes

2013 Senior Notes

Total

$

$

$

$

$

$

$

$

$

$

110,000 
3,406 
106,594 

2016 Senior Notes

110,000 
3,463 
106,537 

3,715 

June 14, 2046
June 14, 2021
6.625 %
7.07 %

152,500 
3,522 
148,978 

2013 Senior Notes

152,500 
3,690 
148,810 

$

$

$

$

262,500 
6,928 
255,572 

Total

262,500 
7,153 
255,347 

5,054 

December 1, 2043
December 1, 2018
7.75 %
8.04 %

The interest expense incurred on the Senior Notes for the year ended December 31, 2022 was $19,106 (2021 - $19,106), of which $1,342 was accrued at both
December 31, 2022 and 2021, respectively. The issuance costs related to the Senior Notes were capitalized and are being amortized over the effective life of the
Senior Notes. The amortization expense was $225 for the year ended December 31, 2022 (2021 - $221).

Under the terms of the 2013 Senior Notes, the 2013 Senior Notes can be redeemed, in whole or in part, at Maiden NA's option at any time and from time to
time, until maturity at a redemption price equal to 100% of the principal amount of the notes to be redeemed plus accrued but unpaid interest on the principal
amount being redeemed to, but not including, the redemption date. Maiden NA is required to give at least thirty days and not more than sixty days' notice prior to
the redemption date.

Under the terms of the 2016 Senior Notes, the 2016 Senior Notes can be redeemed, in whole or in part, at Maiden Holdings' option at any time and from time
to time, until maturity at a redemption price equal to 100% of the principal amount of the notes to be redeemed plus accrued but unpaid interest on the principal
amount being redeemed to, but not including, the redemption date. Maiden Holdings is required to give at least thirty days and not more than sixty days notice
prior to the redemption date.

F-31

 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 
(In thousands of U.S. dollars, except share and per share data)

8. Reinsurance

The  Company  uses  reinsurance  and  retrocessional  agreements  ("ceded  reinsurance")  to  mitigate  volatility,  reduce  its  exposure  to  certain  risks  and  provide
capital  support.  Ceded  reinsurance  provides  for  the  recovery  of  a  portion  of  loss  and  LAE  under  certain  circumstances  without  relieving  the  Company  of  its
obligations to the policyholders. The Company remains liable to the extent that any of its reinsurers or retrocessionaires fails to meet their obligations. Loss and
LAE incurred and premiums earned are reported after deduction for ceded reinsurance. In the event that one or more of our reinsurers or retrocessionaires are
unable to meet their obligations under these agreements, the Company would not realize the full value of the reinsurance recoverable balances.

The  effect  of  ceded  reinsurance  on  net  premiums  written  and  earned  and  on  net  loss  and  LAE  for  the  years  ended  December  31,  2022  and  2021  was  as

follows:

For the Year Ended December 31,
Premiums written
Direct
Assumed
Ceded

Net
Premiums earned
Direct
Assumed
Ceded

Net
Loss and LAE
Gross loss and LAE
Loss and LAE ceded

Net

2022

2021

$

$

$

$

$

$

24,553  $
(19,074)
(397)
5,082  $

24,534  $
13,599 
(401)
37,732  $

53,508  $
4,483 
57,991  $

21,866 
(10,928)
(535)
10,403 

22,857 
31,497 
(1,361)
52,993 

9,344 
(2,037)
7,307 

The  Company's  reinsurance  recoverable  on  unpaid  losses  balance  as  at  December  31,  2022  was  $556,116  (2021  -  $562,845)  presented  in  the  Consolidated

Balance Sheets. At December 31, 2022 and 2021, the Company had no valuation allowance against reinsurance recoverable on unpaid losses.

On  December  27,  2018,  Cavello  Bay  Reinsurance  Limited  ("Cavello")  and  Maiden  Reinsurance  entered  into  a  retrocession  agreement  pursuant  to  which
certain assets and liabilities associated with the U.S. treaty reinsurance business held by Maiden Reinsurance were 100.0% retroceded to Cavello in exchange for a
ceding commission. The reinsurance recoverable on unpaid losses due from Cavello under this retrocession agreement was $60,112 at December 31, 2022 (2021 -
$69,006).

On  July  31,  2019,  Maiden  Reinsurance  and  Cavello  entered  into  a  Loss  Portfolio  Transfer  and  Adverse  Development  Cover  Agreement  ("LPT/ADC
Agreement"), pursuant to which Cavello assumed the loss reserves as of December 31, 2018 associated with the AmTrust Quota Share in excess of a $2,178,535
retention  up  to  $600,000,  in  exchange  for  a  retrocession  premium  of  $445,000.  The  $2,178,535  retention  is  subject  to  adjustment  for  paid  losses  subsequent
to December 31, 2018. The LPT/ADC Agreement provides Maiden Reinsurance with $155,000 in adverse development cover over its carried AmTrust Quota
Share  loss  reserves  at  December  31,  2018.  The  LPT/ADC  Agreement  meets  the  criteria  for  risk  transfer  and  is  thus  accounted  for  as  retroactive  reinsurance.
Cumulative ceded losses exceeding $445,000 are recognized as a deferred gain liability and amortized into income over the settlement period of the ceded reserves
in proportion to cumulative losses collected over the estimated ultimate reinsurance recoverable. The amount of the deferral is recalculated each period based on
loss  payments  and  updated  estimates.  Consequently,  cumulative  adverse  development  subsequent  to  December  31,  2018  may  result  in  significant  losses  from
operations until periods when the deferred gain is recognized as a benefit to earnings. As of December 31, 2022, the reinsurance recoverable on unpaid losses
under the LPT/ADC Agreement was $490,408 while the deferred gain liability under the LPT/ADC Agreement was $45,408 (December 31, 2021 - $490,860 and
$45,860, respectively). Amortization of the deferred gain will not occur until paid losses have exceeded the minimum retention under the LPT/ADC Agreement,
which is presently estimated to be in 2025.

Cavello  provided  collateral  in  the  form  of  a  letter  of  credit  in  the  amount  of  $445,000  to  AmTrust  under  the  LPT/ADC  Agreement.  Cavello  is  subject  to
additional collateral funding requirements as explained in "Note 10 — Related Party Transactions". As of December 31, 2022, the amount of collateral required
was  $461,563.  Under  the  terms  of  the  LPT/ADC  Agreement,  the  covered  losses  associated  with  the  Commutation  and  Release  Agreement  with  AmTrust  are
eligible to be covered but recoverable only when such losses are paid or settled by AII or its affiliates, provided such losses and other related amounts shall not
exceed  $312,786.  Cavello's  parent  company,  Enstar  Group  Limited  ("Enstar"),  has  credit  ratings  of  BBB  from  both  Standard  &  Poor's  and  Fitch  Ratings  at
December 31, 2022.

F-32

 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

9. Reserve for Loss and Loss Adjustment Expenses

General

The  Company  uses  both  historical  experience  and  industry-wide  loss  development  factors  to  provide  a  reasonable  basis  for  estimating  future  losses.  In  the
future,  certain  events  may  be  beyond  the  control  of  management,  such  as  changes  in  law,  judicial  interpretations  of  law,  and  rates  of  inflation,  which  may
favorably or unfavorably impact the ultimate settlement of the Company’s loss and LAE reserves.

The  anticipated  effect  of  inflation  is  implicitly  considered  when  estimating  liabilities  for  loss  and  LAE.  While  anticipated  changes  in  claim  costs  due  to
inflation  are  considered  in  estimating  the  ultimate  claim  costs,  changes  in  the  average  severity  of  claims  are  caused  by  a  number  of  factors  that  vary  with  the
individual  type  of  policy  written.  Ultimate  losses  are  projected  based  on  historical  trends  adjusted  for  implemented  changes  in  underwriting  standards,  claims
handling, policy provisions, and general economic trends. Those anticipated trends are monitored based on actual development and are modified if necessary.

The reserving process begins with the collection and analysis of paid losses and incurred claims data for each of the Company's contracts. While reserves are
mostly reviewed on a contract by contract basis, paid loss and incurred claims data is also aggregated into reserving segments. The segmental data is disaggregated
by reserving class and further disaggregated by either accident year (i.e. the year in which the loss event occurred) or by underwriting year (i.e. the year in which
the contract generating the premium and losses incepted). In cases where the Company uses underwriting year information, reserves are subsequently allocated to
the respective accident year. The reserve for loss and LAE comprises:

December 31,
Reserve for reported loss and LAE
Reserve for losses incurred but not reported ("IBNR")

Reserve for loss and LAE

The following table represents a reconciliation of the beginning and ending gross and net loss and LAE reserves:

For the Year Ended December 31,
Gross loss and LAE reserves, January 1
Less: reinsurance recoverable on unpaid losses, January 1
Net loss and LAE reserves, January 1
Net incurred losses related to:

Current year
Prior years

Net paid losses related to:

Current year
Prior years

Change in deferred gain on retroactive reinsurance
GLS run-off business acquired or assumed
Effect of foreign exchange rate movements
Net loss and LAE reserves, December 31
Reinsurance recoverable on unpaid losses, December 31

Gross loss and LAE reserves, December 31

Actuarial Methods Used to Estimate Loss and LAE Reserves

2022

2021

702,691  $
428,717 
1,131,408  $

851,950 
637,423 
1,489,373 

2022

2021

1,489,373  $
562,845 
926,528 

25,355 
32,636 
57,991 

(701)
(398,499)
(399,200)
3,587 
10,905 
(24,519)
575,292 
556,116 
1,131,408  $

1,893,299 
592,571 
1,300,728 

34,912 
(27,605)
7,307 

(10,026)
(389,231)
(399,257)
29,081 
14,825 
(26,156)
926,528 
562,845 
1,489,373 

$

$

$

$

The Company utilizes a variety of standard actuarial methods in its analysis of loss reserves. The selections from these various methods are based on the loss

development characteristics of the specific line of business and significant actuarial judgment. The actuarial methods utilized include:

The Expected Loss Ratio ("ELR") method is a technique that is multiplicative and applies an expected loss ratio to premium earned to yield the estimated
ultimate losses. The ELR assumption is generally derived from pricing information and historical experience of the business. This method is frequently used for
the purpose of stability in the early valuations of an underwriting year with large and uncertain loss development factors. This technique does not take into account
actual  loss  emergence  for  the  underwriting  year  being  projected.  As  an  underwriting  year  matures  and  actual  loss  experience  becomes  more  credible,  other
methods may be applied in determining the estimated ultimate losses.

F-33

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

9. Reserve for Loss and Loss Adjustment Expenses (continued)

The Loss Development ("LD") method is a reserving method in which ultimate losses are estimated by applying a loss development factor to actual reported
(or  paid)  loss  experience.  This  method  fully  utilizes  actual  experience.  Multiplication  of  underwriting  year  actual  reported  (or  paid)  losses  by  its  respective
development factor produces the estimated ultimate losses. The LD method is based upon the assumption that the relative change in a given underwriting year’s
losses  from  one  evaluation  point  to  the  next  is  similar  to  the  relative  change  in  prior  underwriting  years’  losses  at  similar  evaluation  points.  In  addition,  this
method is based on the assumption that the reserving and payment patterns as well as the claim handling procedures have not changed substantially over time. In
the case where changes to the payment patterns or the claim handling procedures are identified, historical losses are adjusted to the current basis, and development
factors are selected based on the relative change of the adjusted losses (the Berquist Sherman method is one example of this approach). When a company has a
sufficiently  reliable  loss  development  history,  a  development  pattern  based  on  the  company’s  historical  indications  may  be  used  to  develop  losses  to  ultimate
values.

The Bornhuetter-Ferguson ("BF") reserving technique is used for long-tailed or lower frequency, more volatile lines. It is also useful in situations where the
reported  loss  experience  is  relatively  immature  and/or  lacks  sufficient  credibility  for  the  application  of  methods  that  are  more  heavily  reliant  on  emerged
experience.  The  BF  method  is  an  additive  IBNR  method  that  combines  the  ELR  and  LD  techniques  by  splitting  the  expected  loss  into  two  pieces  -  expected
reported (or paid) losses and expected unreported (or unpaid) losses. Expected unreported (unpaid) losses, estimated by the use of loss development factors, are
added  to  the  current  actual  reported  (or  paid)  losses  to  produce  an  estimate  of  ultimate  losses  by  underwriting  year.  The  BF  method  introduces  an  element  of
stability that moderates the impact of inconsistent changes in paid and reported losses.

The average frequency and severity ("FS") reserving technique is used for lines where claim count is available, and the estimate of loss development factors is
more difficult due to volatility in historical data. The available data for such lines is usually more volatile in the estimation of future losses using the LD and BF
reserving  methods.  The  FS  method  uses  historical  data  to  estimate  the  average  number  of  ultimate  claims  (frequency)  and  the  average  costs  of  closed  claims
(severity). The estimate of ultimate losses by underwriting year is the result of the multiplication of the ultimate number of claims and the average cost of a claim.

With  the  guidance  of  the  methods  above,  actuarial  judgment  is  applied  in  the  determination  of  ultimate  losses.  In  general,  the  Company’s  segments  have
varying levels of seasoning with which the Company has direct experience and as a result, differing methods are utilized to estimate loss and LAE reserves in each
segment.

In the Diversified Reinsurance segment, the Company utilizes the ELR approach at the onset of reserving an account, the BF method for business with less but
maturing loss experience, and as the experience matures the LD method. For proportional or pro-rata business, the Company typically relies heavily on the actual
historical contract experience to estimate reserving parameters such as loss development factors, whereas for excess of loss business there will be more usage of
industry and/or Company benchmark assumptions.

The Company underwrote the AmTrust Reinsurance segment from July 1, 2007 until January 30, 2019, when Maiden Reinsurance and AII agreed to terminate
the  remaining  business  subject  to  the  AmTrust  Quota  Share  on  a  run-off  basis  effective  as  of  January  1,  2019,  and  Maiden  Reinsurance,  AEL  and  AIU  DAC
agreed  to  terminate  the  European  Hospital  Liability  Quota  Share  on  a  run-off  basis  effective  as  of  January  1,  2019.  A  large  proportion  of  the  exposure  in  the
underlying book of business has significant seasoning, and allows for a significant amount of credibility in using parameters derived from historical experience to
calculate reserve estimates. Some segments of the book are a result of recent acquisitions or newer markets for AmTrust. These segments require a greater level of
assumptions and professional judgment in deriving ultimate losses, which inherently implies a wider range of reasonable estimates. As a result, the Company has
tended to rely on a weighted approach which primarily employs the LD method for aspects of the segment with ample historical data, while also considering the
ELR  or  BF  method  for  exposure  resulting  from  recent  acquisitions,  or  a  relative  business  with  a  more  limited  level  of  experience.  The  FS  method  is  also
considered for segments of the AmTrust Reinsurance book of business for which claim count information is available. Additional data detailing items such as
class of business, state, claim counts, frequency and severity is available, further enhancing the reserve analysis.

Prior Year Development

Prior period development arises from changes to loss estimates recognized in the current year that relate to loss reserves established in previous calendar years.
The  favorable  or  unfavorable  development  reflects  changes  in  management's  best  estimate  of  the  ultimate  losses  under  the  relevant  reinsurance  policies  after
considerable review of changes in actuarial assessments. The following table summarizes the (adverse) favorable prior period development experienced in each of
our reportable segments for the years ended December 31, 2022 and 2021:

For the Year Ended
December 31, 2022
December 31, 2021

Diversified
Reinsurance

AmTrust
Reinsurance

$

(4,552) $
3,561 

(28,084) $
24,044 

Total

(32,636)
27,605 

F-34

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

9. Reserve for Loss and Loss Adjustment Expenses (continued)

During 2022, the Company's incurred losses increased for 2021 and prior accident years by $32,636 or 3.5% of prior year net loss and LAE reserves. The
Company  had  decreased  incurred  losses  for  2020  and  prior  accident  years  of  $27,605  or  2.1%  during  2021.  The  net  adverse  prior  year  loss  development  of
$32,636  for  the  year  ended  December  31,  2022  was  primarily  driven  by  adverse  loss  development  of  $28,084  in  the  AmTrust  Reinsurance  segment  and  net
adverse loss development of $4,552 in the Diversified Reinsurance segment.

In the Diversified Reinsurance segment, net adverse prior year loss development of $4,552 for the year ended December 31, 2022 (2021 - favorable $3,561)
was due to adverse development in GLS, European Capital Solutions and facultative reinsurance run-off business partly offset by favorable reserve development
in German Auto Programs. The net favorable prior year loss development of $3,561 for the year ended December 31, 2021 was due to favorable development in
facultative reinsurance run-off lines as well as auto programs in Australia, the U.K. and Germany. The table below details prior year loss development by line of
business for the years ended December 31, 2022 and 2021:

For the Year Ended December 31,
Prior Year Loss Development adverse (favorable)
IIS business
GLS
Other run-off lines

Total Diversified Reinsurance Prior Year Development

2022

2021

$

$

(1,683) $
1,825 
4,410 
4,552  $

(2,044)
— 
(1,517)
(3,561)

In the AmTrust Reinsurance segment, net adverse prior year development was $28,084 for the year ended December 31, 2022 (2021 - favorable $24,044). Net
adverse prior year loss development of $28,084 during the year ended December 31, 2022 is driven by unfavorable movements in Commercial Auto Liability,
General Liability, Other Specialty Risk & Extended Warranty and European Hospital Liability, partly offset by favorable development in Workers Compensation.
European Hospital Liability was due in part to higher than expected loss emergence in Italian Hospital Liability policies as well as the agreed exit cost of $3,666
(€3,444) for the commutation of French Hospital Liability policies as described in "Note 10. Related Party Transactions".

Net  favorable  prior  year  loss  development  in  2021  was  largely  due  to  Workers  Compensation  and  Commercial  Auto  Liability  partly  offset  by  adverse
development in General Liability and European Hospital Liability. The table below details prior year loss development by lines of business for the years ended
December 31, 2022 and 2021:

For the Year Ended December 31,
Prior Year Loss Development adverse (favorable) before impact of LPT/ADC Agreement
Workers Compensation
Commercial Auto Liability
General Liability
European Hospital Liability
Other Lines
Other Specialty Risk & Extended Warranty

Total AmTrust Reinsurance Prior Year Development

2022

2021

$

$

(38,131) $
19,088 
18,452 
13,247 
(1,685)
17,113 
28,084  $

(22,242)
(29,918)
20,868 
7,885 
(637)
— 
(24,044)

The change in the deferred gain on retroactive reinsurance of $3,587 for the year ended December 31, 2022 (2021 - $29,081) relates to retroactive reinsurance
in GLS and the LPT/ADC Agreement in the AmTrust Reinsurance Segment. The decrease in the deferred gain liability and related reinsurance recoverable on
unpaid losses under the LPT/ADC Agreement with Cavello was $452 in the year ended December 31, 2022 (2021 - $29,081) due to favorable development on
loss  reserves  covered  under  the  LPT/ADC  Agreement,  specifically  Workers  Compensation.  The  deferred  gain  on  retroactive  reinsurance  under  the  LPT/ADC
Agreement represents the cumulative adverse development for covered risks under the AmTrust Quota Share as of December 31, 2022 and 2021. Amortization of
the deferred gain will not occur until paid losses have exceeded the minimum retention under the LPT/ADC Agreement, which is estimated to be in 2025.

F-35

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

9. Reserve for Loss and Loss Adjustment Expenses (continued)

a) Claims Development

The  following  is  a  summary  of  the  Company's  incurred  and  paid  loss  development  by  accident  year,  net  of  reinsurance,  from  the  last  ten  calendar  years
including the total reserve for losses, IBNR, plus development on reported loss and LAE for specific lines of business in our reportable segments, Diversified
Reinsurance and AmTrust Reinsurance, as of December 31, 2022. Information prior to 2022 is included as unaudited supplementary information. The incurred and
paid amounts have been translated from the local currency to U.S. dollars using the December 31, 2022 spot rate for all years presented in the table below in order
to isolate changes in foreign exchange rates from loss development. As a reinsurer of primarily quota share contracts, claim counts are available on a very limited
basis. Therefore claim counts have not been provided in the tables below as it is impractical to do so.

Diversified Reinsurance segment incurred and paid losses are analyzed by following lines of business: (1) International; (2) GLS and (3) Other run-off lines.
Loss development tables have not been presented for GLS and other run-off lines as loss development tables are not required for currently insignificant categories,
therefore the GLS contracts and other run-off lines have been aggregated into two separate categories and included in the reconciliation disclosure only.

AmTrust Reinsurance segment incurred and paid losses are analyzed by the following lines of business: (1) Workers’ Compensation; (2) Commercial Auto
Liability;  (3)  General  Liability;  (4)  European  Hospital  Liability;  and  (5)  All  Other  Lines.  There  are  a  number  of  factors  to  consider  when  evaluating  the
information in these tables:

• In the Diversified Reinsurance segment, contracts in the International business are written on both an accident year and underwriting year basis, some are
multi-line and the majority of the premium is associated with proportional contracts. Many proportional treaty reinsurance contracts are submitted using
quarterly bordereau reporting by underwriting year. However, the remaining losses can generally only be allocated to accident years based on estimated
premium  earning  and  loss  reporting  patterns.  Further  estimates  are  required  to  allocate  losses  to  line  of  business.  Multi-line  accounts  are  generally
analyzed on an individual basis by line of business, but are booked in the Company’s records to a contract, rather than to each individual line of business
within  a  contract.  For  the  purpose  of  this  disclosure  allocations  are  made  to  the  various  lines  of  business.  Management’s  assumptions  and  allocation
procedures for these tables may produce results that differ from the actual loss emergence reported by line of business each quarter;

• The AmTrust Reinsurance segment consists primarily of two contracts, the European Hospital Liability Quota Share and a much larger quota share that
includes all other covered business, the AmTrust Quota Share. There is also a small amount of excess of loss business that has not been written since
2009 which is included as a reconciling item. Maiden receives several cession statements and uses these to report premiums in three categories - Small
Business  Commercial,  Specialty  Program  and  Specialty  Risk  and  Extended  Warranty  in  Note  3.  Segment  Information.  The  tables  provided  include
allocations of IBNR reserves to line of business by accident year.

• Management’s assumptions and allocation procedures for these tables may produce results that differ from the actual loss emergence reported by line of

business each quarter; and

• For both segments, the premium and exposure for prior accident years is often reported to us in subsequent periods, as reporting lags exist from an insurer
to a reinsurer. This leads to increases in the provision for loss and LAE in prior years, but does not reduce expected income (and in many cases can result
in additional income).

Diversified Reinsurance Segment: GLS

GLS provides a full range of legacy services to small insurance companies, particularly those in run-off or with blocks of reserves that are no longer core to
those companies' operations. GLS works with clients to develop and implement finality solutions including acquiring entire companies that enable our clients to
meet their capital and risk management objectives.

Loss development tables have not been presented for GLS as the loss reserves and paid claims for each individual contract is currently insignificant, therefore
the loss reserves for all the GLS contracts have been aggregated into a separate category and included in the reconciliation disclosure only. For GLS exposure, loss
reserves are calculated primarily from utilizing the LD or FS methods. As the exposure being reinsured is typically retroactive in nature and covers more mature
portfolios, the ELR or BF approach is not highly relied upon.

As  of  December  31,  2022,  GLS  related  companies  and  its  subsidiaries  have  insurance  liabilities  assumed  primarily  through  a  few  retroactive  reinsurance
contracts  which  included  total  loss  reserves  of  $28,230  and  a  loss  recoverable  of  $4,669.  Losses  incurred  for  the  year  ended  December  31,  2022  include  paid
losses of $7,129 and total loss reserves include IBNR reserves of $14,595 at December 31, 2022.

Also, please see "Note 5 — Fair Value Measurements" for the derivative liability of $14,559 on a reinsurance contract written by GLS which is included in
accrued  expenses  and  other  liabilities.  The  fair  value  of  this  derivative  instrument  is  determined  using  a  discounted  cash  flow  model  in  which  the  Company
examines current market conditions, historical results as well as contract specific information that may impact future cash flows to assess the reasonableness of
inputs used in the valuation model.

F-36

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

9. Reserve for Loss and Loss Adjustment Expenses (continued)

Diversified Reinsurance Segment: IIS Business

The following tables represent information on the Company's incurred loss and LAE and cumulative paid loss and LAE, both net of reinsurance, since 2013 for
the  Company's  IIS  business  in  the  Diversified  Reinsurance  segment.  The  development  tables  below  included  reserves  acquired  from  the  loss  portfolio  transfer
agreement associated with the GMAC International Insurance Services ("IIS") business as at November 30, 2010 of $98,827. For the purposes of disclosure, the
reserves from the loss portfolio transfer was allocated to the original accident year.

Many pro-rata contracts are big enough that specific company development patterns are used. The ELR from the pricing of the account is typically used for the
first year or more until the data suggests an alternative result is likely. Use of the ELR method transitions to the BF and then the LD method. For smaller contracts,
benchmark  development  patterns  may  be  used  in  both  the  pricing  to  establish  the  ELR  and  the  reserving.  The  use  of  benchmark  patterns  is  more  prevalent  in
excess of loss business and the movement to experience based methods is slower.

The IIS business written by the Company's IIS team is mainly proportional treaty business, a significant portion of which is Personal Auto quota share but also
comprises credit life quota share. Life and personal accident business is also written on a direct basis by Maiden LF. The IIS business team works with insurance
partners,  automobile  manufacturers  and  their  related  credit  providers  and  other  organizations  to  design  and  implement  insurance  programs  in  both  auto
distribution-related and other consumer insurance products.

For the auto quota share exposure, initial underwriting year loss projections are generally based on the ELR method, derived from account pricing analyses.
Payment and reporting patterns are predominantly short-tailed, and the movement away from the ELR to BF or LD methods typically happens very rapidly. Credit
life reserves are primarily a function of reporting lag, typically only one or several months on average. The reserves are calculated using a FS methodology, where
the frequency is a function of the average claims lag and the average per claims severity.

F-37

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

9. Reserve for Loss and Loss Adjustment Expenses (continued)

Diversified
Reinsurance - IIS
business
For the Year
Ended December
31,

Accident Year:
2010
2011
2012
2013
2014
2015
2016
2017
2018
2019
2020
2021
2022
Total

For the Year
Ended December
31,

Accident Year:
2010
2011
2012
2013
2014
2015
2016
2017
2018
2019
2020
2021
2022
Total

Incurred loss and LAE, net of reinsurance

At
December 31
2022

2013

2014

2015

2016

2017

2018

2019

2020

2021

2022

Total IBNR

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

$

74,743  $
45,794 
45,177 
42,423 

74,417  $
45,974 
45,443 
47,521 
42,353 

72,469  $
45,931 
45,547 
48,835 
48,084 
42,615 

74,544  $
45,762 
45,630 
48,337 
47,947 
44,026 
38,500 

76,544  $
46,140 
45,891 
48,937 
47,843 
44,510 
40,487 
36,543 

76,259 
46,391 
45,612 
48,770 
47,641 
44,183 
39,874 
37,344 
41,124 

77,255  $
46,349 
45,559 
49,138 
47,705 
44,219 
39,860 
36,275 
39,484 
34,665 

77,373  $
46,310 
45,491 
49,073 
47,464 
44,080 
40,239 
35,413 
39,659 
36,632 
23,417 

77,666  $
46,310 
45,590 
49,173 
47,354 
43,821 
39,953 
35,432 
39,689 
35,713 
22,584 
6,337 

$

77,870  $
46,422 
45,626 
49,219 
47,401 
43,842 
40,044 
35,239 
39,854 
35,869 
21,528 
6,433 
7,383 
496,730  $

(583
10
29
(115
6
(122
(68
12
(31
1,47
1,77
5
1,71
4,41

Cumulative paid loss and LAE, net of reinsurance

2013

2014

2015

2016

2017

2018

2019

2020

2021

2022

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

$

45,531  $
44,406 
38,237 
22,864 

47,263  $
45,638 
40,608 
42,125 
23,559 

48,852  $
46,055 
41,692 
44,599 
41,807 
21,584 

50,367  $
46,287 
42,017 
45,940 
44,070 
39,143 
22,112 

51,847  $
46,428 
42,599 
46,408 
45,292 
41,199 
36,206 
18,824 

53,423  $
46,534 
42,706 
46,608 
45,531 
42,137 
37,912 
32,343 
19,613 

54,794  $
46,597 
42,719 
46,683 
45,632 
42,525 
38,612 
33,993 
35,506 
16,250 

55,834  $
46,677 
42,799 
46,985 
45,742 
42,787 
39,199 
34,764 
37,472 
29,408 
11,192 

56,888  $
46,727 
42,891 
47,393 
45,801 
42,988 
39,685 
35,007 
38,454 
31,986 
18,898 
5,693 

57,801 
46,719 
42,808 
47,460 
45,800 
42,988 
40,466 
35,044 
38,999 
32,464 
19,848 
10,122 
1,175 
461,694 

$

35,036 

Total net reserves

F-38

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

9. Reserve for Loss and Loss Adjustment Expenses (continued)

The following tables represent information on the Company's incurred loss and LAE and cumulative paid loss and LAE, both net of reinsurance, by significant
line of business since 2011 for our AmTrust Reinsurance segment. All data shown for the AmTrust Reinsurance segment in the tables that follow are from the
Company’s  quota  share  contracts  with  AmTrust,  both  the  multi-year  AmTrust  Quota  Share  and  European  Hospital  Liability  Quota  Share.  AmTrust  purchases
significant reinsurance for losses above $10 million covered by the AmTrust Quota Share. The Company’s share of AmTrust’s losses net of reinsurance in the
AmTrust Quota Share is generally 40%.

Additionally,  for  the  Specialty  Program  portion  of  Covered  Business  only,  AmTrust  will  be  responsible  for  ultimate  net  loss  otherwise  recoverable  from
Maiden Reinsurance to the extent that the loss ratio to Maiden Reinsurance, which shall be determined on an inception to date basis from July 1, 2007 through the
date of calculation, is between 81.5% and 95% ("Loss Corridor"). Above and below the Loss Corridor, Maiden Reinsurance has reinsured losses at its proportional
40% share per the AmTrust Quota Share. Effective July 31, 2019, the Loss Corridor was amended such that the maximum amount covered is $40,500, the amount
calculated  by  Maiden  Reinsurance  for  the  Loss  Corridor  coverage  as  of  March  31,  2019.  As  of  December  31,  2022,  the  projected  amount  subject  to  the  Loss
Corridor is $52,950 which exceeds the maximum amount covered. Any further development above this amount will be subject to the coverage of the LPT/ADC
Agreement.

Recoverables from the LPT/ADC Agreement are displayed in the column "Impact of LPT/ADC" in the tables below. Amounts have been allocated to Accident
Year and line of business according to the timing of the respective losses, based on the currently projected payout patterns. These allocations may shift over time
as actual payments are made and payout patterns are re–estimated. Please refer to "Note 8 — Reinsurance" for additional information regarding the LPT/ADC
Agreement.

AmTrust Reinsurance: Workers’ Compensation 

This reserve class consists of the Workers’ Compensation portion of the AmTrust Quota Share. The business is written in the U.S. by AmTrust from both their
Small Commercial Business and Specialty Program business units. The Small Commercial Business unit focuses on writing smaller, niche workers' compensation
exposures in generally low-hazard occupations. Workers’ Compensation business written in the Specialty Program unit is typically part of programs consisting of
multiple lines of business. The business is produced by managing general agents with AmTrust regularly adding new programs and terminating or renegotiating
unprofitable  ones.  Our  initial  underwriting  year  loss  projections  are  generally  based  on  the  ELR  method,  derived  from  historical  performance  after  the
consideration of loss and premium trends. Since it is proportional exposure, and due to the size and the classes of business insured by AmTrust, this reserving class
is much shorter tailed than a traditional workers compensation book, and the transition to the BF and the LD methods happens relatively quickly, within the first
several years.

This line of business is covered under the LPT/ADC Agreement pursuant to which Cavello has assumed the loss reserves as of December 31, 2018 associated
with  the  AmTrust  Quota  Share  and  therefore  any  adverse  development  will  be  recoverable  as  per  terms  of  the  agreement.  Recoverables  from  the  LPT/ADC
Agreement are displayed in the column "Impact of LPT/ADC" in the loss triangle tables below.

F-39

Workers'
Compensation

For the Year
Ended
December 31,

Accident Year:
2008
2009
2010
2011
2012
2013
2014
2015
2016
2017
2018
2019

Total

For the Year
Ended
December 31,

Accident Year:
2008
2009
2010
2011
2012
2013
2014
2015
2016
2017
2018
2019
Total

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

9. Reserve for Loss and Loss Adjustment Expenses (continued)

Incurred loss and LAE, net of reinsurance (excluding impact of LPT/ADC Agreement)

At December 31, 2022

2013
Unaudited

2014
Unaudited

2015
Unaudited

2016
Unaudited

2017
Unaudited

2018
Unaudited

2019
Unaudited

2020
Unaudited

2021
Unaudited

2022

Total IBNR

Impact of
LPT/ADC

$

82,438 

$

81,240 

$

82,301 

$

83,039 

$

83,622 

$

84,710 

$

83,952  $

86,117  $

86,292  $

86,415 

$

2,351 

$

103,864 

118,209 

130,712 

168,016 

237,019 

109,213 

120,243 

132,728 

173,946 

245,765 

379,589 

106,204 

125,020 

133,995 

171,040 

238,392 

365,515 

474,140 

105,901 

124,073 

133,916 

172,692 

242,447 

382,260 

474,212 

528,906 

107,165 

123,968 

135,379 

181,616 

261,915 

419,748 

526,269 

568,006 

615,957 

110,175 

127,215 

138,600 

192,087 

276,249 

457,363 

551,145 

627,728 

654,362 

592,566 

109,664 

127,381 

139,685 

188,879 

273,571 

455,521 

545,271 

603,529 

613,577 

580,528 

12,751 

109,021 

126,621 

141,272 

192,263 

281,580 

449,374 

549,857 

579,849 

593,920 

575,765 

9,945 

110,207 

126,516 

137,355 

187,089 

277,365 

445,258 

547,439 

568,791 

591,122 

585,009 

10,871 

109,384 

126,308 

140,257 

189,114 

277,226 

441,185 

537,963 

559,440 

580,155 

577,485 

10,152 

1,899 

6,848 

5,193 

8,935 

10,213 

21,099 

28,451 

40,851 

30,646 

32,953 

(1,534)

3,388 

3,846 

5,672 

7,479 

11,453 

16,426 

32,018 

45,036 

54,400 

70,284 

84,446 

— 

$

3,635,084 

$

187,905 

$

334,448 

Cumulative paid loss and LAE, net of reinsurance

2013
Unaudited

2014
Unaudited

2015
Unaudited

2016
Unaudited

2017
Unaudited

2018
Unaudited

2019
Unaudited

2020
Unaudited

2021
Unaudited

2022

$

76,018 

$

77,370 

$

78,161 

$

79,230 

$

81,159 

$

82,436 

$

82,709  $

82,286  $

82,676  $

89,462 

95,120 

91,414 

88,382 

56,249 

93,425 

103,280 

105,584 

119,059 

121,182 

69,512 

96,396 

108,171 

114,107 

138,706 

168,785 

189,954 

86,695 

98,811 

114,639 

115,966 

150,543 

199,300 

268,467 

246,616 

110,051 

100,103 

115,014 

122,579 

158,807 

216,527 

321,258 

338,642 

284,501 

111,508 

101,823 

115,959 

124,315 

164,512 

227,502 

355,414 

388,640 

380,602 

274,596 

110,954 

102,877 

116,332 

125,843 

168,154 

234,342 

370,176 

417,736 

428,651 

448,551 

409,986 

3,907 

103,771 

114,730 

129,408 

172,251 

248,103 

383,529 

448,867 

449,347 

485,611 

465,762 

5,821 

104,205 

115,508 

130,413 

174,436 

252,506 

392,101 

466,868 

471,382 

507,903 

499,349 

8,070 

82,761 

104,434 

115,765 

130,958 

175,021 

255,720 

398,441 

476,769 

484,367 

520,180 

515,459 

9,024 

3,268,899 

364 

366,549 

Total net reserves excluding impact of LPT/ADC Agreement

All outstanding liabilities prior to 2008, net of reinsurance

Less: Impact of LPT/ADC Agreement
Total net reserves including impact of LPT/ADC Agreement

(334,448)

$

32,101 

F-40

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

9. Reserve for Loss and Loss Adjustment Expenses (continued)

AmTrust Reinsurance: General Liability 

This reserve class consists of the General Liability portion of the AmTrust Quota Share. The business is written in the U.S. by AmTrust from both their Small
Commercial  Business  and  Specialty  Program  business  units.  The  Small  Commercial  Business  unit  focuses  on  writing  smaller  niche  business,  typically  under-
served by the broader insurance market, which typically have limits of $1,000. General Liability business written in the Small Commercial Business unit grew
substantially  following  AmTrust’s  renewal  rights  acquisition  in  2014.  Specialty  Program  business  may  contain  a  mix  of  exposures  from  retail  operations,
contractors, manufacturers, and other premises.

Our initial underwriting year loss projections are generally based on the ELR method, derived from historical performance after the consideration of loss and
premium trends. This proportional exposure is medium tailed, and the IBNR is typically derived from the use of the initial ELR, or the FS method as claim counts
emerge, for the first several years following the earning of the exposure, followed by a transition to the BF and the LD methods.

F-41

General
Liability
For the Year
Ended
December 31,
Accident
Year:
2008
2009
2010
2011
2012
2013
2014
2015
2016
2017
2018
2019

Total

For the Year
Ended
December 31,
Accident
Year:
2008
2009
2010
2011
2012
2013
2014
2015
2016
2017
2018
2019
Total

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

9. Reserve for Loss and Loss Adjustment Expenses (continued)

Incurred loss and LAE, net of reinsurance (excluding impact of LPT/ADC Agreement)

2013

2014

2015

2016

2017

2018

2019

2020

2021

2022

At December 31, 2022

Total
IBNR

Impact of
LPT/ADC

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

$

33,051 

$

33,792 

$

34,169 

$

35,985 

$

36,627 

$

37,605 

$

36,996  $

40,398  $

40,381  $

40,017 

$

3,036 

$

29,123 

34,761 

35,628 

33,445 

42,021 

30,902 

36,455 

40,557 

42,450 

43,116 

65,469 

32,418 

38,536 

42,100 

48,851 

66,869 

66,558 

118,111 

34,040 

38,298 

45,303 

50,800 

68,641 

77,930 

95,766 

98,149 

34,863 

41,597 

49,338 

55,991 

79,731 

99,873 

122,942 

114,864 

116,158 

35,138 

42,884 

52,746 

59,948 

89,204 

111,970 

139,518 

120,911 

133,533 

121,991 

35,410 

43,062 

53,499 

63,429 

92,032 

116,085 

154,071 

148,371 

165,268 

153,822 

5,427 

36,228 

45,490 

55,607 

63,704 

95,050 

119,367 

154,529 

147,858 

161,354 

148,817 

6,017 

35,733 

44,778 

54,683 

64,052 

96,342 

119,782 

154,939 

147,996 

162,856 

148,295 

5,981 

35,495 

44,856 

54,288 

63,615 

96,388 

119,413 

155,234 

150,019 

167,257 

151,791 

3,906 

431 

330 

278 

3,450 

2,159 

6,211 

7,150 

11,764 

18,159 

18,617 

1,962 

121 

143 

340 

600 

1,426 

3,606 

7,612 

13,950 

20,042 

29,737 

35,974 

— 

$

1,082,279 

$

73,547 

$

113,551 

Cumulative paid loss and LAE, net of reinsurance

2013

2014

2015

2016

2017

2018

2019

2020

2021

2022

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

$

29,384 

$

32,849 

$

32,423 

$

32,765 

$

34,935 

$

36,699 

$

34,893  $

37,253  $

37,278  $

19,727 

19,010 

12,158 

13,224 

4,996 

24,298 

26,429 

22,963 

18,020 

10,226 

3,503 

28,312 

30,948 

31,619 

29,752 

32,249 

24,581 

20,849 

30,924 

34,125 

39,350 

40,864 

44,698 

36,026 

33,963 

6,402 

32,878 

37,317 

41,257 

45,775 

58,377 

57,678 

52,350 

21,959 

6,967 

33,473 

39,214 

47,141 

53,526 

70,074 

77,259 

79,291 

45,855 

27,001 

7,907 

32,487 

39,888 

49,178 

56,538 

76,996 

86,101 

98,278 

67,064 

51,545 

24,618 

27 

34,984 

42,509 

51,492 

55,350 

83,571 

92,861 

112,542 

88,627 

79,531 

42,792 

314 

34,999 

43,076 

52,592 

57,913 

87,178 

96,521 

120,546 

101,764 

97,356 

65,947 

717 

37,473 

35,093 

44,040 

53,064 

58,889 

89,473 

102,290 

131,224 

114,422 

119,417 

90,841 

1,218 

877,444 

16 

204,851 

Total net reserves excluding impact of LPT/ADC Agreement

All outstanding liabilities prior to 2008, net of reinsurance

Less: Impact of LPT/ADC Agreement

Total net reserves including impact of LPT/ADC Agreement

(113,551)

$

91,300 

F-42

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

9. Reserve for Loss and Loss Adjustment Expenses (continued)

AmTrust Reinsurance: Commercial Auto Liability  

Commercial Auto Liability is written in the U.S. and included in the Small Commercial Business and Specialty Program business units within the AmTrust
Quota Share. The Small Commercial Business unit focuses on writing smaller niche business, typically under-served by the broader insurance market, and policies
typically  have  limits  of  $1,000.  Auto  Liability  business  written  in  the  Small  Commercial  Business  unit  grew  substantially  following  a  large  renewal  rights
acquisition completed by AmTrust in 2014. Commercial Auto Liability business written in the Specialty Program unit is typically part of programs consisting of
multiple lines of business.

Our initial underwriting year loss projections are generally based on the ELR method, derived from historical performance after the consideration of loss and
premium trends. This proportional exposure is relatively short tailed, and the transition to the BF and the LD methods happens relatively quickly, within the first
several years.

F-43

Commercial
Auto Liability

For the Year
Ended
December 31,
Accident
Year:
2008
2009
2010
2011
2012
2013
2014
2015
2016
2017
2018
2019
2020

Total

For the Year
Ended
December 31,
Accident
Year:
2008
2009
2010
2011
2012
2013
2014
2015
2016
2017
2018
2019
2020
Total

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

9. Reserve for Loss and Loss Adjustment Expenses (continued)

Incurred loss and LAE, net of reinsurance (excluding impact of LPT/ADC Agreement)

2013

2014

2015

2016

2017

2018

2019

2020

2021

2022

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

$ 33,700  $ 34,522  $ 34,584  $ 35,975  $

28,551 
37,154 
29,577 
32,691 
33,473 

30,812 
38,043 
32,578 
40,076 
44,771 
47,525 

31,024 
40,193 
33,839 
44,812 
50,647 
55,023 
66,967 

30,468 
40,523 
34,790 
48,116 
59,702 
73,966 
92,955 
121,828 

35,521  $
30,919 
42,146 
36,149 
46,150 
63,162 
82,427 
106,560 
118,210 
156,575 

35,382  $
31,033 
41,996 
36,065 
45,753 
62,163 
89,299 
119,141 
144,077 
189,257 
177,150 

35,542  $
31,064 
42,070 
34,643 
45,917 
63,620 
92,572 
127,560 
171,504 
220,457 
224,780 
79,172 

37,746  $
31,082 
40,637 
34,707 
45,902 
63,532 
94,238 
129,849 
170,275 
230,972 
230,200 
77,371 

37,854  $
31,019 
40,631 
34,690 
45,753 
63,589 
93,208 
129,082 
167,479 
220,471 
219,800 
73,023 

37,885  $
30,979 
40,608 
34,633 
45,860 
63,500 
93,164 
129,632 
170,221 
224,132 
230,516 
74,553 
— 

$

1,175,683  $

At December 31, 2022

Total
IBNR

Impact of
LPT/ADC

2,063  $
397 
192 
476 
(41)
249 
818 
492 
588 
5,775 
12,231 
9,976 
(7)
33,209  $

13 
50 
32 
— 
4 
79 
462 
848 
2,658 
6,907 
14,413 
— 
— 
25,466 

Cumulative paid loss and LAE, net of reinsurance

2013

2014

2015

2016

2017

2018

2019

2020

2021

2022

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

$ 30,975  $ 32,643  $ 33,536  $ 34,074  $

22,959 
28,602 
18,813 
14,979 
8,267 

26,975 
34,855 
25,808 
26,508 
19,865 
8,450 

29,226 
37,734 
29,769 
35,460 
34,379 
22,858 
13,102 

29,829 
39,413 
32,362 
43,745 
48,122 
42,960 
39,179 
19,071 

34,803  $
29,842 
39,750 
33,130 
44,165 
57,349 
64,459 
62,945 
48,595 
26,863 

35,284  $
30,204 
40,282 
33,155 
45,555 
59,600 
79,766 
86,433 
76,635 
69,657 
30,018 

36,968  $
31,194 
40,395 
33,451 
45,751 
62,331 
87,458 
107,707 
113,174 
115,623 
67,080 
9,456 

34,982  $
30,337 
40,407 
33,872 
45,819 
62,562 
90,761 
118,753 
133,826 
154,600 
107,184 
22,799 
7 

35,013  $
30,340 
40,411 
34,005 
45,812 
62,968 
91,000 
121,605 
145,727 
176,863 
138,770 
34,365 
7 

35,339 
30,341 
40,416 
34,158 
45,825 
63,070 
91,115 
125,415 
158,822 
197,857 
178,479 
49,073 
7 
1,049,917 
59 
125,825 

Total net reserves excluding impact of LPT/ADC Agreement

All outstanding liabilities prior to 2008, net of reinsurance

Less: Impact of LPT/ADC Agreement

Total net reserves including impact of LPT/ADC Agreement

(25,466)
100,359 

$

F-44

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

9. Reserve for Loss and Loss Adjustment Expenses (continued)

AmTrust Reinsurance: European Hospital Liability

AmTrust entered this line of business in Italy in 2010 when it believed there were significant opportunities in what had traditionally been an under-performing
market. European Hospital Liability policies are written on a claim made basis. Maiden wrote a separate annually renewable contract covering this exposure in
2011 which is not part of the AmTrust Quota Share. Currently, most exposure remains in Italy with a modest amount of exposure to other European nations. The
European  Hospital  Liability  Quota  Share  is  a  claims  made  exposure,  and  in  many  instances  claims  are  eventually  closed  with  no  liability.  This  phenomena  is
estimated during the reserving process, and can result in a provision for pure IBNR (reserves for claims which have not yet been reported) which is minimal or
negative. This estimate will vary as the exposure matures which could result in changes to the level of reserves. Also, severity for known claims and expenses can
increase over time, which requires a provision for IBNR. The net result is a relatively small amount of IBNR. European Hospital Liability business is not covered
under the LPT/ADC Agreement, therefore any adverse development in this line of business may result in significant losses.

Our initial underwriting year loss projections are generally based on the ELR method, derived from historical performance after the consideration of loss and
premium trends. As the exposure matures, the projection methodology transitions to the LD method. The underlying policies assumed are subject to deductibles
on both a per claim and aggregate basis. The LD method is applied to both the net of deductible data, as well as individually to gross and deductible protections,
with a final estimate made by evaluating both methodologies.

European
Hospital
Liability
For the Year
Ended December
31,

Accident Year:
2011
2012
2013
2014
2015
2016
2017
2018
2019

Total

For the Year
Ended December
31,

Accident Year:
2011
2012
2013
2014
2015
2016
2017
2018
2019
Total

Incurred loss and LAE, net of reinsurance

At
December 31,
2022

2013
Unaudited

2014
Unaudited

2015
Unaudited

2016
Unaudited

2017
Unaudited

2018
Unaudited

2019
Unaudited

2020
Unaudited

2021
Unaudited

2022

Total IBNR

$ 34,017  $ 46,998  $ 44,705  $ 61,558  $ 59,690  $ 57,234  $

76,985 
46,409 

76,239 
58,306 
48,283 

97,757 
60,822 
50,843 
45,015 

87,448 
79,904 
54,459 
43,704 
42,146 

82,802 
73,060 
60,595 
56,903 
48,519 
38,800 

107,010 
93,646 
76,408 
62,565 
63,503 
49,435 
42,238 

59,387  $
111,624 
99,193 
81,397 
65,550 
65,905 
51,452 
29,957 
15,049 

59,656  $
112,513 
100,519 
82,391 
65,776 
64,463 
50,078 
30,843 
13,930 

60,384  $
113,902 
102,074 
83,677 
67,979 
65,746 
48,183 
30,234 
14,854 

67,547  $
117,038 
104,022 
83,496 
69,511 
65,220 
47,010 
32,374 
14,800 
$ 601,018  $

72 
(958)
(15)
(68)
3,215 
3,414 
3,472 
241 
650 
10,023 

Cumulative paid loss and LAE, net of reinsurance

2013
Unaudited

2014
Unaudited

2015
Unaudited

2016
Unaudited

2017
Unaudited

2018
Unaudited

2019
Unaudited

2020
Unaudited

2021
Unaudited

2022

$ 12,141  $ 22,279  $ 27,253  $ 33,862  $ 39,178  $ 43,149  $

14,556 
2,829 

33,129 
14,230 
3,982 

43,149 
24,483 
11,216 
3,288 

55,476 
37,356 
23,314 
10,456 
3,393 

65,413 
46,959 
33,182 
21,587 
10,079 
1,211 

73,016 
52,626 
37,234 
27,550 
16,700 
4,181 
872 

46,731  $
78,817 
59,493 
43,920 
33,086 
22,214 
7,167 
2,147 
10,856 

51,046  $
88,334 
72,015 
55,203 
43,398 
32,971 
13,910 
5,114 
1,517 

53,859  $
93,133 
77,288 
58,012 
42,931 
35,440 
19,172 
7,359 
2,865 

57,899 
99,707 
84,916 
67,693 
52,110 
44,924 
28,407 
20,980 
9,973 
466,609 
$ 134,409 

Total net reserves

F-45

$

$

All Other
Lines

For the Year
Ended
December 31,

Accident
Year:
2008
2009
2010
2011
2012
2013
2014
2015
2016
2017
2018
2019
2020
2021

Total

For the Year
Ended
December 31,

Accident
Year:
2008
2009
2010
2011
2012
2013
2014
2015
2016
2017
2018
2019
2020
2021

Total

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

9. Reserve for Loss and Loss Adjustment Expenses (continued)

AmTrust  Reinsurance:  All  Other  Lines  Includes  all  lines  except  Workers'  Compensation,  General  Liability,  and  Commercial  Auto  from  Small  Commercial
Business and Specialty Program Divisions. The predominant exposures include property and auto physical damage.

Incurred loss and LAE, net of reinsurance (excluding impact of LPT/ADC Agreement)

At December 31, 2022

2013

2014

2015

2016

2017

2018

2019

2020

2021

2022

Total IBNR

Impact of
LPT/ADC

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

$

28,715 
11,959 
24,718 
26,343 
18,443 
17,806 

$

29,149 
13,329 
15,484 
27,509 
19,426 
17,630 
20,597 

$

29,237 
14,309 
16,078 
22,359 
21,898 
28,058 
25,268 
52,706 

$

29,070 
14,492 
16,105 
22,616 
18,673 
22,918 
26,021 
54,857 
79,654 

29,576 
16,088 
17,071 
23,376 
19,850 
21,313 
24,958 
49,631 
74,948 
104,637 

Unaudited
$

29,574 
15,653 
17,059 
23,506 
20,260 
21,669 
26,278 
49,463 
72,384 
96,812 
96,910 

Unaudited
$

29,519  $
14,617 
15,438 
21,469 
19,578 
21,735 
24,929 
47,882 
73,602 
92,904 
103,489 
37,945 

Unaudited

Unaudited

24,045  $
15,750 
15,905 
21,515 
17,969 
20,644 
21,496 
44,939 
67,060 
96,196 
101,553 
43,146 

24,016  $
15,373 
15,905 
21,500 
17,811 
20,639 
21,491 
44,749 
66,944 
96,104 
101,913 
43,554 

$

24,013 
15,373 
15,905 
21,496 
17,819 
20,637 
21,493 
44,456 
66,791 
96,267 
102,061 
42,003 
— 
— 

$

(4,931)
373 
52 
151 
(260)
1,174 
(17)
711 
6,512 
1,507 
(1,546)
1,025 
(103)
(66)

— 
— 
— 
— 
152 
247 
122 
50 
113 
173 
275 
— 
— 
— 

$

488,314 

$

4,582 

$

1,132 

2013

2014

2015

2016

2017

2018

2019

2020

2021

2022

Cumulative paid loss and LAE, net of reinsurance

Unaudited

Unaudited

Unaudited

Unaudited

Unaudited

$

29,900 
8,743 
13,012 
17,571 
14,031 
11,877 

$

31,217 
11,093 
15,375 
21,279 
16,033 
15,997 
12,028 

$

29,388 
13,105 
15,748 
22,044 
16,936 
17,509 
20,277 
28,929 

$

29,177 
13,870 
16,058 
22,715 
17,946 
20,258 
20,940 
45,208 
42,795 

30,833 
15,224 
16,919 
23,892 
18,205 
20,456 
22,018 
42,631 
69,805 
48,903 

Unaudited
$

30,683 
15,051 
16,786 
23,661 
18,685 
20,447 
26,194 
41,962 
65,452 
80,726 
56,539 

All outstanding liabilities prior to 2008, net of reinsurance

Total net reserves excluding impact of LPT/ADC Agreement

Less: Impact of LPT/ADC Agreement

Total net reserves including impact of LPT/ADC Agreement

F-46

Unaudited
$

Unaudited

Unaudited

29,234  $
14,009 
15,285 
21,481 
17,559 
19,343 
21,405 
44,179 
63,234 
80,735 
86,455 
22,095 

24,706  $
14,954 
15,853 
21,343 
18,071 
20,146 
21,497 
43,622 
63,450 
93,212 
98,386 
38,793 
4 

28,850  $
14,986 
15,854 
21,339 
18,077 
19,465 
21,493 
43,895 
60,008 
93,541 
101,158 
40,427 
103 
66 

28,850 
14,986 
15,854 
21,334 
18,077 
19,463 
21,509 
43,742 
59,967 
94,206 
102,587 
40,670 
103 
66 

481,414 
(5)

6,895 

(1,132)

5,763 

$

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

9. Reserve for Loss and Loss Adjustment Expenses (continued)

Reconciliation of Loss Development Tables to Consolidated Balance Sheet

The  following  table  represents  a  reconciliation  of  the  net  incurred  and  paid  loss  development  tables  to  the  reserve  for  loss  and  LAE  in  the  Consolidated

Balance Sheet at December 31, 2022:

Diversified Reinsurance

IIS business
Other reconciling items excluded from loss development tables

GLS
Other run-off lines

Total Diversified Reinsurance
AmTrust Reinsurance

Workers' Compensation
General Liability
Commercial Auto Liability
European Hospital Liability
All Other Lines
Total
Other reconciling items excluded from loss development tables
Total AmTrust Reinsurance

Total Net Reserves
(including impact of
ADC)

December 31, 2022

Reinsurance
Recoverables on
unpaid claims

Total Gross Reserves

$

35,036  $

927  $

35,963 

23,561 
18,419 
77,016 

32,101 
91,300 
100,359 
134,409 
5,763 
363,932 
134,344 
498,276 

4,669 
— 
5,596 

334,448 
113,551 
25,466 
— 
1,132 
474,597 
15,811 
490,408 

28,230 
18,419 
82,612 

366,549 
204,851 
125,825 
134,409 
6,895 
838,529 
150,155 
988,684 

US Treaty business ceded to Cavello

— 

60,112 

60,112 

Total reserves for loss and LAE

b) Claims duration disclosure

$

575,292  $

556,116  $

1,131,408 

The following unaudited supplementary information represents the average annual percentage payout of net loss and LAE by age, net of reinsurance, for both

our reportable segments at December 31, 2022:

Year 1

Year 2

Year 3

Year 4

Year 5

Year 6

Year 7

Year 8

Year 9

Year 10

Average annual payout of incurred claims by age, net of reinsurance

Diversified Reinsurance
International
AmTrust Reinsurance
Workers' Compensation
General Liability
Commercial Auto
Liability
European Hospital
Liability
All other lines

49.7 %

39.4 %

3.8 %

2.3 %

1.4 %

0.5 %

0.2 %

(0.5)%

— %

0.2 %

18.9 %
6.1 %

32.1 %
10.8 %

18.1 %
13.5 %

8.7 %
16.3 %

4.8 %
14.2 %

3.7 %
10.3 %

12.0 %

17.8 %

19.0 %

18.4 %

14.2 %

7.5 %

3.5 %
57.1 %

7.8 %
32.4 %

11.4 %
2.8 %

14.9 %
4.9 %

10.0 %
2.6 %

7.5 %
(2.5)%

3.0 %
6.9 %

4.5 %

7.2 %
0.5 %

2.4 %
6.1 %

1.2 %

6.6 %
(0.6)%

1.6 %
3.1 %

0.4 %

6.0 %
(2.9)%

1.5 %
3.3 %

0.4 %

3.9 %
(0.2)%

The  average  annual  payout  of  incurred  claims  by  age,  net  of  reinsurance,  is  calculated  using  the  amount  of  claims  paid  in  each  development  year  and  is

compared with the estimated incurred claims as of the most recent period presented.

F-47

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

10. Related Party Transactions

The Founding Shareholders of the Company were Michael Karfunkel, George Karfunkel and Barry Zyskind. Based on each individual's most recent public
filing, Leah Karfunkel (wife of the late Michael Karfunkel), George Karfunkel and Barry Zyskind (the Company's non-executive chairman) each own or control
less than 5.0% of the Company's outstanding common shares. Leah Karfunkel and George Karfunkel are directors of AmTrust, and Barry Zyskind is the chief
executive officer and chairman of AmTrust. Leah Karfunkel, George Karfunkel and Barry Zyskind own or control approximately 55.2% of the ownership interests
of Evergreen Parent, L.P., the ultimate parent of AmTrust.

The following describes transactions that have transpired between the Company and AmTrust:

AmTrust Quota Share

Effective  July  1,  2007,  the  Company  and  AmTrust  entered  into  a  master  agreement,  as  amended  ("Master  Agreement"),  by  which  they  caused  Maiden
Reinsurance and AII to enter into the AmTrust Quota Share by which AII retroceded to Maiden Reinsurance an amount equal to 40% of the premium written by
subsidiaries of AmTrust, net of the cost of unaffiliated inuring reinsurance and 40% of losses. The Master Agreement further provided that AII receive a ceding
commission of 31% of ceded written premiums. On June 11, 2008, Maiden Reinsurance and AII amended the AmTrust Quota Share to add Retail Commercial
Package  Business  to  the  Covered  Business  (as  defined  in  the  AmTrust  Quota  Share).  AII  receives  a  ceding  commission  of  34.375%  on  Retail  Commercial
Package Business. On July 1, 2016, the agreement was renewed through June 30, 2019. Effective July 1, 2018, the amount AEL ceded to Maiden Reinsurance was
reduced to 20%.

Effective  July  1,  2013,  for  the  Specialty  Program  portion  of  Covered  Business  only,  AII  was  responsible  for  ultimate  net  loss  otherwise  recoverable  from
Maiden Reinsurance to the extent that the loss ratio to Maiden Reinsurance, which shall be determined on an inception to date basis from July 1, 2007 through the
date of calculation, is between 81.5% and 95%. Above and below the Loss Corridor, Maiden Reinsurance continued to reinsure losses at its proportional 40%
share  of  the  AmTrust  Quota  Share.  Effective  July  31,  2019,  the  Loss  Corridor  was  amended  such  that  the  maximum  amount  covered  is  $40,500,  the  amount
calculated by Maiden Reinsurance for the Loss Corridor coverage as of March 31, 2019. Any development above this maximum amount will be subject to the
coverage of the LPT/ADC Agreement.

Effective January 1, 2019, Maiden Reinsurance and AII entered into a partial termination amendment ("Partial Termination Amendment") which amended the
AmTrust  Quota  Share.  The  Partial  Termination  Amendment  provided  for  the  cut-off  of  the  ongoing  and  unearned  premium  of  AmTrust’s  Small  Commercial
Business, comprising workers’ compensation, general liability, umbrella liability, professional liability (including cyber liability) insurance coverages, and U.S.
Specialty  Risk  and  Extended  Warranty  ("Terminated  Business")  as  of  December  31,  2018.  Under  the  Partial  Termination  Amendment,  the  ceding  commission
payable by Maiden Reinsurance for its remaining in-force business immediately prior to January 1, 2019 increased by five percentage points with respect to in-
force remaining business (excluding Terminated Business) and related unearned premium as of January 1, 2019. The Partial Termination Amendment resulted in
Maiden Reinsurance returning $647,980 in unearned premium to AII, or $436,760 net of applicable ceding commission and brokerage as calculated during the
second quarter of 2019.

Subsequently, on January 30, 2019, Maiden Reinsurance and AII agreed to terminate the remaining business subject to the AmTrust Quota Share on a run-off

basis effective as of January 1, 2019.

Effective July 31, 2019, Maiden Reinsurance and AII entered into a Commutation and Release Agreement which provided for AII to assume all reserves ceded
by AII to Maiden Reinsurance with respect to its proportional 40% share of the ultimate net loss under the AmTrust Quota Share related to the commuted business
including: (a) all losses incurred in Accident Year 2017 and Accident Year 2018 under California workers' compensation policies and as defined in the AmTrust
Quota Share ("Commuted California Business"); and (b) all losses incurred in Accident Year 2018 under New York workers' compensation policies ("Commuted
New York Business"), and together with the Commuted California Business ("Commuted Business") in exchange for the release and full discharge of Maiden
Reinsurance's obligations to AII with respect to the Commuted Business. The Commuted Business excludes any business classified by AII as Specialty Program
or Specialty Risk business.

Maiden  Reinsurance  paid  $312,786  ("Commutation  Payment"),  which  is  the  sum  of  the  net  ceded  reserves  in  the  amount  of  $330,682  with  respect  to  the
Commuted Business as of December 31, 2018 less payments in the amount of $17,896 made by Maiden Reinsurance with respect to the Commuted Business from
January 1, 2019 through July 31, 2019. The Commutation Payment was settled on August 12, 2019 and Maiden Reinsurance paid AII approximately $6,335 in
interest related to the Commutation Payment premium, calculated at the rate of 3.30% per annum from January 1, 2019 through August 12, 2019.

AII  and  Maiden  Reinsurance  also  agreed  that  as  of  July  31,  2019,  the  AmTrust  Quota  Share  was  deemed  amended  as  applicable  so  that  the  Commuted

Business is no longer included as part of Covered Business under the AmTrust Quota Share.

On  January  30,  2019,  in  connection  with  the  termination  of  the  reinsurance  agreement  described  above,  the  Company  and  AmTrust  entered  into  a  second
amendment to the Master Agreement between the parties, originally entered into on July 3, 2007, to remove the provisions requiring AmTrust to reinsure business
with the Company.

European Hospital Liability Quota Share

Effective April 1, 2011, Maiden Reinsurance entered into the European Hospital Liability Quota Share with AEL and AIU DAC. Pursuant to the terms of the
European  Hospital  Liability  Quota  Share,  Maiden  Reinsurance  assumed  40%  of  the  premiums  and  losses  related  to  policies  classified  as  European  Hospital
Liability, including associated liability coverages and policies covering physician defense costs, written or renewed on or after April 1, 2011. 

F-48

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

10. Related Party Transactions (continued)

The European Hospital Liability Quota Share also covers policies written or renewed on or before March 31, 2011, but only with respect to losses that occur,
accrue or arise on or after April 1, 2011. The maximum limit of liability attaching shall be €5,000 (€10,000 effective January 1, 2012) or currency equivalent (on a
100%  basis)  per  original  claim  for  any  one  original  policy.  Maiden  Reinsurance  paid  a  ceding  commission  of  5%  on  contracts  assumed  under  the  European
Hospital Liability Quota Share.

Effective July 1, 2016, the European Hospital Liability Quota Share was amended such that Maiden Reinsurance assumes from AEL 32.5% of the premiums
and losses of all policies written or renewed on or after July 1, 2016 until June 30, 2017 and 20% of all policies written or renewed on or after July 1, 2017.
Thereafter, on January 30, 2019, Maiden Reinsurance, AEL and AIU DAC agreed to terminate the European Hospital Liability Quota Share on a run-off basis
effective as of January 1, 2019.

Effective July 1, 2022, Maiden Reinsurance and AIU DAC entered into an agreement ("Commutation Agreement") which provided for AIU DAC to assume
all reserves ceded by AIU DAC to Maiden Reinsurance with respect to AIU DAC’s French Medical Malpractice exposures for underwriting years 2012 through
2018 reinsured by Maiden Reinsurance under the European Hospital Liability Quota Share. In accordance with the Commutation Agreement, Maiden Reinsurance
paid $31,291 (€29,401) to AIU DAC, which is the sum of net ceded reserves of $27,625 (€25,956) and an agreed exit cost of $3,666 (€3,444). As a result of the
Commutation Agreement, Maiden Reinsurance reduced its exposure to AmTrust's Hospital Liability business, however, it continues to have exposure to Italian
medical malpractice liabilities under the European Hospital Liability Quota Share.

The table below shows the effect of both of these quota share arrangements with AmTrust on the Company's Consolidated Income Statements for the years

ended December 31, 2022 and 2021, respectively:

For the Year Ended December 31,
Gross and net premiums written
Net premiums earned
Net loss and loss adjustment expenses
Commission and other acquisition expenses

Collateral provided to AmTrust

a) AmTrust Quota Share

2022

2021

$

(18,538) $
9,749 
(45,508)
(4,347)

(5,695)
25,312 
(3,438)
(9,747)

To provide AmTrust's U.S. insurance subsidiaries with credit for reinsurance on their statutory financial statements, AII, as the direct reinsurer of AmTrust's
insurance  subsidiaries,  established  trust  accounts  ("Trust  Accounts")  for  their  benefit.  Maiden  Reinsurance  has  provided  appropriate  collateral  to  secure  its
proportional  share  under  the  AmTrust  Quota  Share  of  AII's  obligations  to  the  AmTrust  subsidiaries  to  whom  AII  is  required  to  provide  collateral  which  can
include  (a)  assets  loaned  by  Maiden  Reinsurance  to  AII  for  deposit  into  the  Trust  Accounts,  pursuant  to  a  loan  agreement  between  those  parties,  (b)  assets
transferred  by  Maiden  Reinsurance  for  deposit  into  the  Trust  Accounts,  or  (c)  a  letter  of  credit  obtained  by  Maiden  Reinsurance  and  delivered  to  an  AmTrust
subsidiary on AII's behalf. Maiden Reinsurance may provide any or a combination of these forms of collateral, provided that the aggregate value thereof equals
Maiden Reinsurance's proportionate share of its obligations under the AmTrust Quota Share. The collateral requirements under the AmTrust Quota Share with AII
was satisfied as follows:

•. by lending funds of $167,975 at December 31, 2022 and 2021 pursuant to a loan agreement entered into between those parties. Advances under the loan
are secured by promissory notes. This loan was assigned by AII to AmTrust effective December 31, 2014 and is carried at cost. Interest is payable at a
rate equivalent to the Federal Funds Effective Rate ("Fed Funds") plus 200 basis points per annum. The interest income on the loan was $6,202 for the
year ended December 31, 2022 (2021 - $3,492) and the effective yield was 3.7% (2021 - 2.1%).

•. on January 30, 2019, in connection with the termination of the reinsurance agreements described above, the Company and AmTrust amended the Loan
Agreement between Maiden Reinsurance, AmTrust and AII, originally entered into on November 16, 2007, by extending the maturity date to January 1,
2025 and specifies that due to the termination of the AmTrust Quota Share, no further loans or advances may be made pursuant to the Loan Agreement;

•. effective December 1, 2008, the Company entered into a Reinsurer Trust Assets Collateral agreement to provide to AII sufficient collateral to secure its
proportional share of AII's obligations to the U.S. AmTrust subsidiaries. The amount of the collateral at December 31, 2022 was approximately $42,305
(2021 - $246,874) and the accrued interest was $224 (2021 - $1,171). Please refer to "Note 4. (e) Investments" for additional information.

•. on  January  11,  2019,  a  portion  of  the  existing  Trust  Accounts  used  for  collateral  on  the  AmTrust  Quota  Share  were  converted  to  a  funds  withheld
arrangement. The Company transferred $575,000 to AmTrust as a funds withheld receivable which had an annual interest rate for 2022 of 2.1%, subject
to annual adjustment (2021 - 1.8%). At December 31, 2022, the balance of funds withheld was $416,835 (2021 - $575,000) and the accrued interest was
$2,359 (2021 - $2,609). The interest income on the funds withheld receivable was $10,791 for the year ended December 31, 2022 (2021 - $10,350).

F-49

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

10. Related Party Transactions (continued)

Pursuant to the terms of the LPT/ADC Agreement, Maiden Reinsurance, Cavello and AmTrust and certain of its affiliated companies entered into a Master
Collateral  Agreement  (“MCA”)  to  define  and  enable  the  operation  of  collateral  provided  under  the  AmTrust  Quota  Share.  Under  the  MCA,  Cavello  provided
letters  of  credit  on  behalf  of  Maiden  Reinsurance  to  AmTrust  in  an  amount  representing  Cavello's  obligations  under  the  LPT/ADC  Agreement.  Because  these
letters of credit replaced other collateral previously provided directly by Maiden Reinsurance to AmTrust, the MCA coordinates the collateral protection that will
be provided to AmTrust to ensure that no gaps in collateral funding occur by operation of the LPT/ADC Agreement and related MCA. As a result of entering into
both the LPT/ADC Agreement and the MCA, certain post-termination endorsements (“PTEs”) to the AmTrust Quota Share between AII and Maiden Reinsurance
were required.

Effective July 31, 2019, the PTEs: i) enable the operation of both the LPT/ADC Agreement and MCA by making provision for certain forms of collateral,
including letters of credit provided by Cavello on Maiden Reinsurance’s behalf, and further defines the permitted use and return of collateral; and ii) increase the
required  funding  percentage  for  Maiden  Reinsurance  under  the  collateral  arrangements  between  the  parties  to  105%  of  its  obligations,  subject  to  a  minimum
excess funding requirement of $54,000, as may be mutually amended by the parties from time to time. Under certain defined conditions, Maiden Reinsurance may
be required to increase this funding percentage to 110%.

Effective March 16, 2020, Maiden Reinsurance discontinued as a Bermuda company and completed its re-domestication to the State of Vermont. Bermuda is a
Solvency  II  equivalent  jurisdiction  and  the  State  of  Vermont  is  not  such  a  jurisdiction;  therefore,  the  collateral  provided  under  the  respective  agreements  with
AmTrust  subsidiaries  was  strengthened  to  reflect  the  impact  of  the  re-domestication  concurrent  with  the  date  of  Maiden  Reinsurance’s  re-domestication  to
Vermont. Maiden Reinsurance and AmTrust agreed to: 1) amend the AmTrust Quota Share pursuant to Post Termination Endorsement No. 2 effective March 16,
2020; and 2) amend the European Hospital Liability Quota Share pursuant to Post Termination Endorsement No. 1 effective March 16, 2020.

Pursuant to the terms of Post Termination Endorsement No. 2 to the AmTrust Quota Share, Maiden Reinsurance strengthened the collateral protection provided
by Maiden Reinsurance to AII by increasing the required funding percentage for Maiden Reinsurance under the collateral arrangements between the parties to
110%  of  its  obligations,  subject  to  a  minimum  excess  funding  requirement  of  $54,000,  as  may  be  mutually  amended  by  the  parties  from  time  to  time.  Post
Termination Endorsement No. 2 also sets forth conditions by which the funding percentage will be reduced and the sequence of how collateral will be utilized as
obligations  as  defined  under  the  AmTrust  Quota  Share  are  satisfied.  Pursuant  to  the  terms  of  Post  Termination  Endorsement  No.  2,  Maiden  Reinsurance
anticipates that the funding percentage will be reduced to 107.5% no later than the first quarter of 2023.

Pursuant to the terms of Post Termination Endorsement No. 1 to the European Hospital Liability Quota Share, Maiden Reinsurance strengthened the collateral
protection provided by Maiden Reinsurance to AEL and AIU DAC by increasing the required funding percentage for Maiden Reinsurance under the collateral
arrangements between the parties to the greater of 120% of the Exposure (as defined therein) and the amount of security required to offset the increase in the
Solvency Capital Requirement (“SCR”) that results from the changes in the SCR which arise out of Maiden Reinsurance's re-domestication as compared to the
SCR  calculation  if  Maiden  Reinsurance  had  remained  domesticated  in  a  Solvency  II  equivalent  jurisdiction  with  a  solvency  ratio  above  100%  and  provided
collateral equivalent to 100% of the Exposure.

b) European Hospital Liability Quota Share

Collateral  has  been  provided  to  both  AEL  and  AIU  DAC  under  the  European  Hospital  Liability  Quota  Share.  For  AEL,  the  amount  of  collateral  held  in
reinsurance trust accounts at December 31, 2022 was $188,473 (2021 - $244,488) and the accrued interest was $966 (2021 - $1,273). For AIU DAC, the Company
utilized  funds  withheld  to  satisfy  its  collateral  requirements  which  was  used  to  settle  the  Commutation  Agreement  on  September  12,  2022.  Therefore,  at
December 31, 2022, the funds withheld balance was $0 (2021 - $26,460) and the accrued interest was $0 (2021 - $141). AIU DAC paid Maiden Reinsurance a
fixed annual interest rate of 0.5% on the average daily funds withheld balance. The interest income on the funds withheld receivable was $59 for the year ended
December 31, 2022 (2021 - $147).

Asset Management Agreement

Effective  July  1,  2007,  the  Company  entered  into  an  asset  management  agreement  with  AII  Insurance  Management  Limited  ("AIIM"),  a  wholly  owned
subsidiary of AmTrust, pursuant to which AIIM agreed to provide investment management services to the Company. Effective January 1, 2018, AIIM provides
investment management services for a quarterly fee of 0.02125% of the average value of the account. The agreement may be terminated upon 30 days written
notice by either party. The Company recorded $417 of investment management fees for the year ended December 31, 2022 (2021 - $846) under this agreement.

On September 9, 2020, Maiden Reinsurance, AmTrust and AIIM entered into a novation agreement, effective July 1, 2020, which provided for the novation of
the asset management agreement, dated January 1, 2018 between Maiden Reinsurance and AIIM, and the release by Maiden Reinsurance of AIIM's obligations
under the asset management agreement. The novation mandates that AmTrust is to be bound by the terms of the asset management agreement in place of AIIM
and AmTrust agrees to perform any and all past, present and future obligations of AIIM under the asset management agreement.

On  November  13,  2020,  Maiden  LF,  Maiden  GF,  AmTrust  and  AIIM  entered  into  a  novation  agreement,  effective  July  1,  2020,  which  provided  for  the
novation of the asset management agreement, dated January 1, 2018 between Maiden LF, Maiden GF and AIIM, and the release by Maiden LF and Maiden GF of
AIIM's obligations under the asset management agreement. The novation mandates that AmTrust is to be bound by the terms of the asset management agreement
in place of AIIM and AmTrust agrees to perform any and all past, present and future obligations of AIIM under the asset management agreement.

F-50

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

11. Commitments, Contingencies and Guarantees

a) Concentrations of Credit Risk

At  December  31,  2022  and  2021,  the  Company’s  assets  where  significant  concentrations  of  credit  risk  may  exist  include  investments,  cash  and  cash
equivalents, loan to related party, reinsurance recoverable on unpaid losses and funds withheld receivable. Please refer to "Note 8 — Reinsurance" for additional
information regarding the Company's credit risk exposure on its reinsurance counterparties including the impact of the LPT/ADC Agreement effective January 1,
2019. The Company requires its reinsurers to have adequate financial strength. The Company evaluates the financial condition of its reinsurers and monitors its
concentration  of  credit  risk  on  an  ongoing  basis.  Provisions  are  made  for  amounts  considered  potentially  uncollectible.  Letters  of  credit  are  provided  by  its
reinsurers for material amounts recoverable as discussed in "Note 8 — Reinsurance".

The Company manages the concentration of credit risk in its investment portfolio through issuer and sector exposure limitations. The Company believes it
bears  minimal  credit  risk  in  its  cash  on  deposit.  The  Company  also  monitors  the  credit  risk  related  to  the  loan  to  related  party  and  funds  withheld  receivable,
within which the largest balances are due from AmTrust. AmTrust has a financial strength/credit rating of A- (Excellent) from A.M. Best at December 31, 2022.
To mitigate credit risk, the Company generally has a contractual right of offset thereby allowing claims to be settled net of any premiums or loan receivable. The
Company believes these balances as at December 31, 2022 will be fully collectible.

b) Concentrations of Revenue

During the year ended December 31, 2022, net premiums earned from AmTrust accounted for $9,749 or 25.8% of total net premiums earned (2021 – $25,312

or 47.8%).

c) Brokers

The Company formerly marketed its Diversified Reinsurance segment through third-party intermediaries as well as directly through its own marketing efforts.
The majority of business within the Diversified Reinsurance segment was marketed directly through our own efforts with no significant reliance on brokers for the
years ended December 31, 2022 and 2021.

d) Letters of Credit

At December 31, 2022, the Company had letters of credit outstanding of $40,319 (2021 - $53,566) for collateral purposes which are secured by cash and fixed

maturities with a fair value of $47,110 at December 31, 2022 (2021 - $72,823).

e) Employment Agreements

The Company has entered into employment agreements with certain individuals. The employment agreements provide for executive benefits and severance

payments under certain circumstances.

f) Operating Lease Commitments

The Company leases office spaces, housing, office equipment and company vehicles under various operating leases expiring in various years through 2024.
The Company's leases are currently classified as operating leases and none of them have any non-lease components. For operating leases that have a lease term of
more  than  twelve  months,  and  whose  lease  payments  are  above  a  certain  threshold,  the  Company  recognizes  a  lease  liability  and  a  right-of-use  asset  in  the
Consolidated Balance Sheets at the present value of the remaining lease payments until expiration. As the lease contracts generally do not provide an implicit
discount rate, the Company used the weighted-average discount rate of 10%, representing its secured incremental borrowing rate, in calculating the present value
of the lease liability.

At  December  31,  2022,  the  Company's  future  lease  obligations  of  $300  (2021  -  $473)  were  calculated  based  on  the  present  value  of  future  annual  rental
commitments excluding taxes, insurance and other operating costs for non-cancellable operating leases discounted using its secured incremental borrowing rate.
This amount has been recognized on the Consolidated Balance Sheets as a lease liability within accrued expenses and other liabilities with an equivalent amount
for the right-of-use asset presented as part of other assets.

The Company has made an accounting policy election not to include renewal, termination, or purchase options that are not reasonably certain of exercise when
determining the term of the borrowing. The Company’s lease agreements do not contain any material residual value guarantees or material restrictive covenants.
The Company's weighted-average remaining lease term is 1.8 years at December 31, 2022.

Under Topic  842,  Leases,  the  Company  continues  to  recognize  the  related  leasing  expense  on  a  straight-line  basis  over  the  lease  term  on  the  Consolidated
Statements of Income. The Company's total lease expense for the year ended December 31, 2022 was $375 (2021 - $613) recognized within net income consistent
with the prior accounting treatment under Topic 840.

F-51

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

11. Commitments, Contingencies and Guarantees (continued)

g) Investment Commitments and Related Financial Guarantees

The Company had total unfunded commitments on alternative investments of $112,989 at December 31, 2022 (2021 - $121,627) which included commitments
for other investments, private equity securities and equity method investments. The table below shows the total unfunded commitments by type of investment as at
December 31, 2022 and 2021:

December 31,

Private equity funds
Private credit funds
Investments in direct lending entities
Other privately held investments
Total unfunded commitments on other investments

Total unfunded commitments on equity securities

Total unfunded commitments on equity method investments

2022

2021

Fair Value

% of Total

Fair Value

% of Total

$

54,996 
13,906 
— 
705 
69,607 

16,509 

26,873 

48.7 % $
12.3 %
— %
0.6 %
61.6 %

14.6 %

23.8 %

46,149 
4,897 
13,216 
4,000 
68,262 

27,415 

25,950 

37.9 %
4.0 %
10.9 %
3.3 %
56.1 %

22.6 %

21.3 %

Total unfunded commitments on alternative investments

$

112,989 

100.0 % $

121,627 

100.0 %

Certain  of  the  Company's  investments  in  limited  partnerships  are  related  to  real  estate  joint  ventures  with  interests  in  multi-property  projects  with  varying
strategies  ranging  from  the  development  of  properties  to  the  ownership  of  income-producing  properties.  In  certain  of  these  joint  ventures,  the  Company  has
provided certain indemnities, guarantees and commitments to certain parties such that it may be required to make payments now or in the future.

Any loss for which the Company could be liable would be contingent on the default of a loan by the real estate joint venture entity for which the Company
provided  a  financial  guarantee  to  a  lender.  While  the  Company  has  committed  to  aggregate  limits  as  to  the  amount  of  guarantees  it  will  provide  as  part  of  its
limited  partnerships,  guarantees  are  only  provided  on  an  individual  transaction  basis  and  are  subject  to  the  terms  and  conditions  of  each  transaction  mutually
agreed by the parties involved. The Company is not bound to such guarantees without its express authorization.

As discussed above, at December 31, 2022, guarantees of $42,141 (2021 - $33,305) were provided to lenders by the Company on behalf of real estate joint
ventures, however, the likelihood of the Company incurring any losses pertaining to project level financing guarantees was determined to be remote. Therefore, no
liability has been accrued under ASC 450-20.

h) Other Collateral

In the ordinary course of business, the Company enters into reinsurance agreements that may include terms which could require the Company to collateralize

certain of its obligations as further discussed in Note 8 — Reinsurance and Note 10 — Related Party Transactions.

i) Deposit Insurance

The Company maintains cash and cash equivalents balances at financial institutions in the U.S., Bermuda and other international jurisdictions. In the U.S., the
Federal  Deposit  Insurance  Corporation  secures  accounts  up  to  $250.  In  certain  other  international  jurisdictions,  there  exist  similar  protections.  Management
monitors balances in excess of insured limits and believes they do not represent a significant credit risk to the Company.

j) Legal Proceedings

Except  as  noted  below,  the  Company  is  not  a  party  to  any  material  legal  proceedings.  The  Company  may  become  involved  in  various  claims  and  legal
proceedings, including arbitrations, that arise in the normal course of its business. These legal proceedings generally relate to claims asserted by or against the
Company in the ordinary course of its insurance or reinsurance operations. Based on the Company's opinion, the eventual outcome of these legal proceedings are
not likely to have a material adverse effect on its financial condition, results of operations or liquidity.

In  April  2009,  the  Company  learned  that  Bentzion  S.  Turin,  the  former  Chief  Operating  Officer,  General  Counsel  and  Secretary  of  Maiden  Holdings  and
Maiden Reinsurance, sent a letter to the U.S. Department of Labor claiming that his employment with the Company was terminated in retaliation for corporate
whistleblowing in violation of the whistleblower protection provisions of the Sarbanes-Oxley Act of 2002. Mr. Turin alleged that he was terminated for raising
concerns regarding corporate governance with respect to the negotiation of the terms of the Trust Preferred Securities Offering. He seeks reinstatement as Chief
Operating Officer, General Counsel and Secretary of Maiden Holdings and Maiden Reinsurance, back pay and legal fees incurred.

F-52

 
 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

11. Commitments, Contingencies and Guarantees (continued)

On December 31, 2009, the U.S. Secretary of Labor found no reasonable cause for Mr. Turin’s claim and dismissed the complaint in its entirety. Mr. Turin
objected to the Secretary's findings and requested a hearing before an administrative law judge in the U.S. Department of Labor. The Company moved to dismiss
Mr. Turin's complaint, and its motion was granted by the Administrative Law Judge on June 30, 2011. On July 13, 2011, Mr. Turin filed a petition for review of
the Administrative Law Judge's decision with the Administrative Review Board in the U.S. Department of Labor. On March 29, 2013, the Administrative Review
Board reversed the dismissal of the complaint on procedural grounds, and remanded the case to the administrative law judge. The administrative hearing began in
September 2014 and concluded in November 2018. On September 2, 2021, Administrative Law Judge Theresa C. Timlin of the U.S. Department of Labor issued a
decision and order which denied Mr. Turin’s complaint in full. On September 16, 2021, Mr. Turin filed a petition for review of the Administrative Law Judge's
decision with the Administrative Review Board in the U.S. Department of Labor. The Company believes that it had good and sufficient reasons for terminating
Mr. Turin's employment and that the claim is without merit. The Company will continue to vigorously defend itself against this claim.

A putative class action complaint was filed against Maiden Holdings, Arturo M. Raschbaum, Karen L. Schmitt, and John M. Marshaleck in the United States
District Court for the District of New Jersey on February 11, 2019. On February 19, 2020, the Court appointed lead plaintiffs, and on May 1, 2020, lead plaintiffs
filed an amended class action complaint (the “Amended Complaint”).The Amended Complaint asserts violations of Section 10(b) of the Exchange Act and Rule
10b-5 (and Section 20(a) for control person liability) arising in large part from allegations that Maiden failed to take adequate loss reserves in connection with
reinsurance  provided  to  AmTrust.  Plaintiffs  further  claim  that  certain  of  Maiden  Holdings’  representations  concerning  its  business,  underwriting  and  financial
statements were rendered false by the allegedly inadequate loss reserves, that these misrepresentations inflated the price of Maiden Holdings' common stock, and
that when the truth about the misrepresentations was revealed, the Company’s stock price fell, causing Plaintiffs to incur losses. On September 11, 2020, a motion
to dismiss was filed on behalf of all Defendants. On August 6, 2021, the Court issued an order denying, in part, Defendants’ motion to dismiss, ordering Plaintiffs
to file a shorter amended complaint no later than August 20, 2021, and permitting discovery to proceed on a limited basis. On February 7, 2023, the District Court
denied  Plaintiffs’  motion  for  reconsideration  of  the  District  Court’s  decision  denying  Plaintiffs’  objection  to  the  Magistrate  Judge’s  December  2021  ruling  on
discovery.  The  Company  expects  to  file  a  dispositive  motion  in  the  near  future.  We  believe  the  claims  are  without  merit  and  we  intend  to  vigorously  defend
ourselves. It is possible that additional lawsuits will be filed against the Company, its subsidiaries and its respective officers due to the diminution in value of our
securities as a result of our operating results and financial condition. It is currently uncertain as to the effect of such litigation on our business, operating results
and financial condition.

F-53

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

12. Earnings per Common Share

The following is a summary of the elements used in calculating basic and diluted earnings per common share:

For the Year Ended December 31,
Numerator:
Net (loss) income
Gain from exchange of preference shares – Series A, C and D
Gain from repurchase of preference shares – Series A, C and D
Amount allocated to participating common shareholders
Net income allocated to Maiden common shareholders
Denominator:
Weighted average number of common shares – basic
Potentially dilutive securities:
Share options and restricted share units
Adjusted weighted average common shares – diluted

(2)

(1)

Basic and diluted earnings per share attributable to Maiden common shareholders

2022

2021

(60,041) $
87,240 
28,233 
(314)
55,118  $

26,645 
— 
90,998 
(1,021)
116,622 

87,112,711 

86,068,278 

1,263 
87,113,974 

0.63  $

4,389 
86,072,667 
1.35 

$

$

$

(1) This represents the share in net income using the two-class method for holders of non-vested restricted shares issued to the Company's employees under the 2019 Omnibus Incentive Plan.
(2) Please  refer  to  "Note  6  —  Shareholders'  Equity"  and  "Note  14  —  Share  Compensation  and  Pension  Plans"  in  the  Notes  to  Consolidated  Financial  Statements  for  the  terms  and  conditions  of

securities that could potentially be dilutive in the future. For the year ended December 31, 2022, there were 1,263 potentially dilutive securities (2021 - 4,389).

F-54

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

13. Income Taxes

Under current Bermuda law, Maiden Holdings received an undertaking from the Bermuda government exempting them from all local income, withholding and
capital gains taxes until March 31, 2035. At the present time, no such taxes are levied in Bermuda. Maiden Holdings believes that they operate in a manner such
that they will not be considered to be engaged in a trade or business in the U.S. Accordingly, Maiden Holdings has not recorded any provision for U.S. taxation.

Maiden NA files a consolidated federal income tax return for the Company’s U.S. based subsidiaries, including Maiden Reinsurance, which re-domesticated to
Vermont on March 16, 2020 and, as a result, became subject to U.S. taxes. Maiden NA has Net Operating Loss carry-forwards ("NOL") and other Deferred Tax
Assets  (“DTA”)  and  Deferred  Tax  Liabilities  (“DTL”)  that  are  not  presently  recognized  as  a  net  DTA  because  a  full  valuation  allowance  is  currently  carried
against them.

Our U.S. subsidiaries are subject to federal, state and local corporate income taxes and other taxes applicable to U.S. corporations. The provision for federal
income  taxes  was  determined  under  the  principles  of  the  consolidated  tax  provisions  of  the  U.S.  Internal  Revenue  Code  and  Regulations.  Should  our  U.S.
subsidiaries pay a dividend outside the U.S. group, withholding taxes will apply. Tax years 2019 to 2021 are subject to examination in the U.S by the Internal
Revenue Service.

The Company has subsidiary operations in various other locations around the world, including Canada, Ireland, Sweden and the United Kingdom, that are
subject  to  relevant  taxes  in  those  jurisdictions.  These  subsidiaries  are  not  under  examination  but  generally  remain  subject  to  examination  in  all  applicable
jurisdictions  for  tax  years  from  2018  through  2022.  Deferred  income  taxes  have  not  been  accrued  with  respect  to  certain  undistributed  earnings  of  foreign
subsidiaries as it is the intention that such earnings will remain reinvested or will not be taxable. If the earnings were to be distributed, as dividends or otherwise,
such amounts may be subject to withholding tax in the country of the paying entity. Currently, however, no withholding taxes have been accrued.

There were no unrecognized tax benefits at December 31, 2022 and 2021. Total (loss) income before income taxes and total income tax (benefit) expense for

the years ended December 31, 2022 and 2021 are as follows:

For the Year Ended December 31,
Loss before income taxes – Domestic (Bermuda)
(Loss) income before income taxes – Foreign (U.S. and others)

Total (loss) income before income taxes

Current tax expense – Domestic (Bermuda)
Current tax (benefit) expense – Foreign (U.S. and others)
Total current tax (benefit) expense

Deferred tax expense – Domestic (Bermuda)
Deferred tax benefit – Foreign (U.S. and others)
Total deferred tax benefit

Total income tax (benefit) expense

2022

2021

(20,509) $
(40,089)
(60,598) $

(23,345)
50,005 
26,660 

—  $

(478)
(478)

— 
(79)
(79)

(557) $

— 
244 
244 

— 
(229)
(229)

15 

$

$

$

$

The following table is a reconciliation of the actual income tax rate for the years ended December 31, 2022 and 2021 to the amount computed by applying the

effective tax rate of 0.0% under Bermuda law to the Company's loss before income taxes:

For the Year Ended December 31,
(Loss) income before income taxes
Less: income tax (benefit) expense

Net (loss) income
Reconciliation of effective tax rate (% of income before income taxes)
Bermuda tax rate
U.S. taxes at statutory rates
Valuation allowance in respect of U.S. taxes
Other jurisdictions

Actual tax rate

2022

2021

$

$

(60,598)
(557)
(60,041)

$

$

— %
36.5 %
(36.5)%
0.9 %
0.9 %

26,660 
15 
26,645 

— %
24.3 %
(22.3)%
(1.9)%
0.1 %

F-55

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

13. Income Taxes (continued)

Deferred income taxes reflect the tax impact of temporary differences between the carrying amounts of assets and liabilities for financial reporting and income

tax purposes. The significant components of the Company's deferred tax assets and liabilities at December 31, 2022 and 2021 were as follows:

December 31,
Deferred tax assets:
Net operating losses
Unearned premiums
Capital loss carry-forward
Net unrealized losses on investments
Discounting of net loss and LAE reserves
Interest limitation
Deferred gain on retroactive reinsurance
Others
Deferred tax assets before valuation allowance
Valuation allowance
Deferred tax assets, net
Deferred tax liabilities:
Deferred commission and other acquisition expenses
Others
Deferred tax liabilities

Net deferred tax asset

2022

2021

$

$

58,939  $
2,813 
3,036 
23,276 
22,964 
— 
11,032 
1,175 
123,235 
116,237 
6,998 

5,767 
56 
5,823 
1,175  $

48,346 
4,202 
2,831 
2,236 
30,423 
11 
10,282 
840 
99,171 
90,077 
9,094 

8,201 
53 
8,254 
840 

The net deferred tax asset at December 31, 2022 was $1,175 (2021 - $840). A valuation allowance has been established against the net U.S. deferred tax assets
which  is  primarily  attributable  to  net  operating  losses  and  capital  losses.  At  this  time,  the  Company  believes  it  is  necessary  to  establish  a  valuation  allowance
against the U.S. net deferred tax assets as more evidence is needed regarding the utilization of these losses. During 2022, the Company recorded an increase in the
valuation allowance of $26,160 (2021 - decrease of $6,337).

At December 31, 2022, the Company has available net operating loss carry-forwards of $280,664 (2021 - $230,220) for income tax purposes which expire
beginning in 2029. At December 31, 2022, the Company also has a capital loss carry-forward of $14,458 (2021 - $13,483) which will expire in beginning in 2023.

F-56

MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

14. Share Compensation and Pension Plans

The Company’s Amended and Restated 2007 Share Incentive Plan ("2007 Plan") provided for grants of options, restricted shares and restricted share units.
New  shares  were  issued  upon  exercise  of  options  and  vesting  of  restricted  shares  and  share  units.  The  total  number  of  common  shares  currently  reserved  for
issuance  under  the  Plan  was  10,000,000.  The  2007  Plan  was  administered  by  the  Compensation  Committee  of  the  Board  of  Directors  (the  "Compensation
Committee").

2019 Omnibus Incentive Plan

During  the  2019  Annual  General  Meeting  of  Shareholders  of  the  Company  held  on  December  10,  2019,  the  2007  Plan  was  terminated,  assumed  by  and
replaced with the 2019 Omnibus Incentive Plan ("2019 Omnibus Plan"). The Company filed the Form S-8 "Securities offered to employees pursuant to employee
benefit plans" with the SEC on January 20, 2020, which covers the offer and resale of up to 11,289,956 of the Company's common shares. Such shares may be
offered and sold from time to time by certain officers and directors of the Company who have acquired or will acquire shares pursuant to the 2019 Omnibus Plan.
The 2019 Omnibus Plan is administered by the Compensation Committee.

Share Options

Exercise prices of options are established at or above the fair market value of the Company’s common shares at the date of grant. Under the 2019 Omnibus
Plan, unless otherwise determined by the Committee and provided in an award agreement, 25% of the options will become exercisable on the first anniversary of
the grant date, with an additional 6.25% of the options vesting each quarter thereafter based on the grantee’s continued employment over a four-year period, and
will expire ten years after grant date.

The fair value of each option grant is separately estimated for each vesting date. The fair value of each option is amortized into compensation expense on a
straight-line basis between the grant date for the award and each vesting date. The Company has estimated the fair value of all share option awards on the date of
the grant by applying the Black-Scholes-Merton multiple-option pricing valuation model. The application of this valuation model involves assumptions that are
judgmental and highly sensitive in the determination of compensation expense.

This table shows all share option activity under the 2019 Omnibus Plan for the years ended December 31, 2022 and 2021:

Outstanding, December 31, 2020

Expired

Outstanding, December 31, 2021

Exercised
Expired
Forfeited

Outstanding, December 31, 2022

Total exercisable, December 31, 2022

Number of 
Share 
Options

Weighted 
Average 
Exercise 
Price

264,500  $
(49,500)
215,000 
(7,500)
(57,250)
(6,250)
144,000 
144,000 

9.22 
10.57 
8.91 
1.31 
7.20 
7.20 
9.72 

9.72 

Weighted 
Average 
Remaining 
Contractual 
Term
4.72 years

4.28 years

3.40 years

3.40 years

Aggregate 
Intrinsic 
Value

$

Range of Option Exercise Prices
(Low to High)

$1.31

$13.98

1.31

13.98

3.24

3.24

13.98

13.98

— 

13 
7 

— 

— 

The  weighted  average  grant  date  fair  value  is  $2.29  (2021  -  $2.13)  for  all  options  outstanding  at  December  31,  2022.  There  was  $0  (2021  -  $1)  of  total
unrecognized compensation cost related to non-vested options outstanding at December 31, 2022. There were 7,500 share options exercised during the year ended
December 31, 2022 (2021 - zero).

Restricted Shares

The fair value of each restricted share is determined based on the market value of the Company's common shares on the date of grant. The total estimated fair
value is amortized as an expense on a straight-line basis over the requisite service period as determined by the Committee, which varies between zero  to  three
years for employees and one year for directors.

Non-Performance-Based ("NPB") Restricted Shares

It is the Company's intention that annually, on or around June 1, each non-employee director will receive a grant of $65 worth of compensation which, if non-
cash compensation, will vest on the first anniversary of the grant. On an annual basis, the Company grants each non-employee director $65 worth of compensation
in the form of either restricted shares, which vest on the first anniversary of the grant, share options or cash. For the year ended December 31, 2022, the Company
issued  a  total  of  382,436  (2021  -  238,750)  restricted  shares  to  non-employee  directors  as  well  as  employees  for  compensation  related  to  their  services.  The
restricted shares for non-employee directors were issued on June 1, 2022 pursuant to the 2019 Omnibus Plan and vest in full on June 1, 2023.

The restricted shares issued to other employees will vest after two years of service. The total fair value of NPB Restricted Shares that vested during the year

ended December 31, 2022 was $455 (2021 - $1,442).

F-57

 
 
 
 
 
 
 
 
 
 
 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

14. Share Compensation and Pension Plans (continued)

Discretionary Performance-Based ("PB") Restricted Shares

During the year ended December 31, 2022, a total of 724,702 (2021 - 1,322,410) restricted shares were granted to senior management and employees pursuant
to  the  2019  Omnibus  Plan,  of  which  724,702  (2021  -  1,322,410)  restricted  shares  vested  immediately.  The  remaining  restricted  shares  issued  to  other  senior
employees vested within two years of service. The total fair value of PB Restricted Shares that vested during the year ended December 31, 2022 was $2,148 (2021
- $3,623).

The following table shows the summary of activity for the Company's restricted share awards:

Non-vested at December 31, 2020

Awards granted
Awards vested
Awards forfeited

Non-vested at December 31, 2021

Awards granted
Awards vested
Awards forfeited

Non-vested at December 31, 2022

Non-Performance-Based Restricted Shares
Weighted Average
Grant-Date Fair
Value

Number of 
Restricted Shares

1,243,270  $
238,750 
(1,178,522)
(54,166)
249,332 
382,436 
(137,677)
(1,628)
492,463 

1.22 
3.44 
1.22 
1.20 
3.35 
2.51 
3.30 
3.07 

2.71 

Discretionary Performance-Based
Restricted Shares

Number of 
Restricted Shares

238,294  $

1,322,410 
(1,322,410)
(200)
238,094 
724,702 
(962,796)
— 
— 

Weighted Average
Grant-Date Fair
Value

1.26 
2.74 
2.74 
1.26 
1.26 
2.55 
2.23 
— 

— 

Total unrecognized compensation cost of $567 related to restricted shares at December 31, 2022, which will be recognized during the next 0.90 years. Total

share-based expense for the year ended December 31, 2022 was $2,740 (2021 - $4,771).

Pension Plans

The  Company  provides  pension  benefits  to  eligible  employees  principally  through  its  sponsorship  of  various  defined  contribution  plans  which  vary  by

subsidiary. The Company’s total expenses for its defined contribution pension plans for the year ended December 31, 2022 was $707 (2021 - $764).

F-58

 
 
MAIDEN HOLDINGS, LTD. 
  NOTES TO CONSOLIDATED FINANCIAL STATEMENTS
(In thousands of U.S. dollars, except share and per share data)

15. Statutory Requirements and Dividend Restrictions

Our insurance and reinsurance operations are subject to insurance and/or reinsurance laws and regulations in the jurisdictions in which they operate. These
regulations include certain liquidity and solvency requirements whereby restrictions are imposed on the amount of dividends or other distributions, such as loans
or cash advances, available to shareholders without prior approval of the insurance regulatory authorities. The statutory capital and surplus and statutory net (loss)
income of our principal operating subsidiaries in their respective jurisdictions were as follows:

Statutory Capital and Surplus
December 31, 2022
December 31, 2021

Statutory Net Income (Loss)
For the Year Ended December 31, 2022
For the Year Ended December 31, 2021

a) United States of America

Maiden Reinsurance
(a)

Maiden LF (b)

Maiden GF (b)

  $

$

898,137  $
999,843 

7,807  $
8,250 

(88,240) $
36,309 

(507) $
(899)

8,471 
9,972 

(289)
(1,018)

Under Vermont statutory regulations, no captive insurance company may pay a dividend out of, or other distribution with respect to, capital or surplus without
the prior approval of the Commissioner. Approval of an ongoing plan for the payment of dividends or other distributions shall be conditioned upon the retention,
at the time of each payment, of capital or surplus in excess of amounts specified by, or determined in accordance with formulas approved by, the Commissioner.
Notwithstanding  the  provisions  of  11B  Vermont  Statutes  Annotated  chapter  13,  a  captive  insurance  may  make  such  distributions  as  are  in  conformity  with  its
purposes  and  approved  by  the  Commissioner.  In  the  second  quarter  of  2022,  the  Vermont  DFR  approved  an  annual  dividend  program  to  be  paid  by  Maiden
Reinsurance  to  Maiden  NA,  with  notification  to  the  Vermont  DFR  as  dividends  are  paid.  Subsequent  to  that  approval,  Maiden  Reinsurance  paid  $18,750  in
dividends to Maiden NA during the year ended December 31, 2022.

Maiden Reinsurance is also required to maintain minimum levels of solvency and liquidity as determined by Vermont law, and to comply with Risk-Based
Capital ("RBC") requirements and licensing rules as specified by the National Association of Insurance Commissioners ("NAIC"). RBC is used to evaluate the
adequacy of capital and surplus maintained by Maiden Reinsurance in relation to risks associated with: (i) asset risk; (ii) insurance risk; (iii) interest rate risk and
(iv) business risk. At December 31, 2022, Maiden Reinsurance's statutory capital and surplus exceeded the amount required to be maintained of $106,976 as of
that date.

b) Sweden

The Company has two Swedish domiciled insurance subsidiaries in Sweden, Maiden LF and Maiden GF, both regulated by the Swedish Finansinspektionen

("Swedish FSA").

Maiden LF was required to maintain a minimum level of statutory capital and surplus of $4,341 at December 31, 2022 (2021 - $4,207). This requirement was
met by Maiden LF throughout the respective years. LF's statutory assets were $15,812 at December 31, 2022 (2021 - $17,545) and its statutory capital and surplus
was $7,807 at December 31, 2022 (2021 - $8,250). Maiden LF is subject to statutory and regulatory restrictions under the Swedish FSA that limit the maximum
amount of annual dividends or distributions paid by Maiden LF to Maiden Holdings. As of December 31, 2022 and 2021, Maiden LF was not allowed to pay
dividends or distributions without the permission of the Swedish FSA. No dividends were paid during the years ended December 31, 2022 and 2021.

Maiden GF was required to maintain a minimum level of statutory capital and surplus of $5,616 at December 31, 2022 (2021 - $5,059). This requirement was
met by Maiden GF throughout the respective years. GF's statutory assets were $13,500 at December 31, 2022 (2021 - $15,573) and its statutory capital and surplus
was $8,471 at December 31, 2022 (2021 - $9,972). Maiden GF is subject to statutory and regulatory restrictions under the Swedish FSA that limit the maximum
amount of annual dividends or distributions paid by Maiden GF to Maiden Holdings. As of December 31, 2022, Maiden GF was not allowed to pay dividends or
distributions without the permission of the Swedish FSA. No dividends were paid during the years ended December 31, 2022 and 2021.

F-59

 
 
SUBSIDIARIES OF THE REGISTRANT

Exhibit 21.1

Subsidiary
Maiden Holdings, Ltd.

Maiden Holdings North America, Ltd.

Maiden Global Servicing Company, LLC

     Maiden Reinsurance Ltd.

       Genesis Legacy Solutions, LLC ("GLS")

   GLS Services Company ("GLS Services")

         Genesis Legacy Insurance Company (Vermont) Limited
         Cypress – Genesis Incorporated Cell Company
         AMS – Genesis Incorporated Cell Company
         MFB – Genesis Incorporated Cell Company

CPA Insurance Inc.

NEKO 2018 A, LLC
NEKO 2018 D, LLC
NEKO 2018 E, LLC
94 Pembroke GP Corp.
94 Pembroke LP Corp.
Maiden Life Försäkrings AB
Maiden General Försäkrings AB
Regulatory Capital Limited
Maiden Global Holdings Ltd.

Note
(1)

(2)
(3)
(4)
(5)
(6)
(7)
(8)
(9)
(10)
(11)
(11)
(11)
(11)
(11)

Jurisdiction

Delaware
Delaware
Vermont
Delaware
Delaware
Vermont
Vermont
Vermont
Vermont
Vermont
Texas
Texas
Texas
British Columbia
British Columbia
Sweden
Sweden
Ireland
England & Wales

100% wholly owned subsidiary of Maiden Holdings North America, Ltd.

(1) All subsidiaries are 100% wholly owned by Maiden Holdings, Ltd. unless otherwise noted.
(2)
(3) Effective March 16, 2020, Maiden Reinsurance Ltd. is domiciled in Vermont, United States and became 100% wholly owned subsidiary of Maiden Holdings North America, Ltd.
(4) GLS was acquired by Maiden Reinsurance Ltd. on November 24, 2020.
(5)
(6)
(7)
(8)
(9)
(10) 100% wholly owned subsidiary of GLS acquired on December 30, 2022.
(11) 100% wholly owned subsidiary of Maiden Reinsurance Ltd.

100% wholly owned subsidiary of GLS.
100% wholly owned subsidiary of GLS Services incorporated on July 19, 2021
100% wholly owned subsidiary of GLS Services incorporated on July 21, 2021.
100% wholly owned subsidiary of GLS Services incorporated on December 29, 2021.
100% wholly owned subsidiary of GLS Services incorporated on March 22, 2022.

 
 
 
 
 
 
 
 
Exhibit 22.1

List of each of the parent company’s subsidiaries that is a guarantor, issuer, or co-issuer of guaranteed
securities registered or being registered that the parent company issues, co-issues, or guarantees.

Subsidiary
Maiden Holdings, Ltd.

Maiden Holdings North America, Ltd.

Note
(1)
(2)

Jurisdiction

Delaware

1. Maiden  Holdings'  100%  wholly  owned  subsidiary,  Maiden  Holdings  North  America,  Ltd.  has  outstanding  publicly-traded  senior  notes

which were issued in 2013 ("2013 Senior Notes").

2. The 2013 Senior Notes issued by Maiden Holdings North America, Ltd. are fully and unconditionally guaranteed by Maiden Holdings. The

Senior Notes are unsecured and insubordinate obligations of Maiden Holdings.

 
    
 
 
Consent of Independent Registered Public Accounting Firm

We consent to the incorporation by reference in the Registration Statement (Form S-8 No. 333-235948) pertaining to Maiden Holdings,
Ltd. 2019 Omnibus Incentive Plan of our reports dated March 15, 2023, with respect to the consolidated financial statements of Maiden
Holdings,  Ltd.  and  the  effectiveness  of  internal  control  over  financial  reporting  of  Maiden  Holdings,  Ltd.  included  in  this  Annual
Report (Form 10-K) for the year ended December 31, 2022.

Exhibit 23.1

/s/ Ernst & Young LLP

New York, NY

March 15, 2023

 
I, Lawrence F. Metz, certify that:

1. 

I have reviewed this annual report on Form 10-K of Maiden Holdings, Ltd.;

CERTIFICATION

EXHIBIT 31.1

2.  Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements

made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report;

3.  Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial

condition, results of operations and cash flows of the registrant as of, and for, the periods presented in this report;

4.  The registrant's other certifying officer and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Exchange Act
Rules 13a-15(e) and 15d-15(e)) and internal control over financial reporting (as defined in Exchange Act Rules 13a-15(f) and 15d-15(f) for the registrant and
have:

(a) Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure
that  material  information  relating  to  the  registrant,  including  any  consolidated  subsidiaries,  is  made  known  to  us  by  others  within  those  entities,
particularly during the period in which this report is being prepared;

(b) Designed such internal control over financial reporting, or caused such internal control over financial reporting to be designed under our supervision, to
provide  reasonable  assurance  regarding  the  reliability  of  financial  reporting  and  the  preparation  of  financial  statements  for  external  purposes  in
accordance with generally accepted accounting principles.

(c) Evaluated the effectiveness of the registrant's disclosure controls and procedures and presented in this report our conclusions about the effectiveness of

the disclosure controls and procedures, as of the end of the period covered by this report based on such evaluation; and

(d) Disclosed in this report any change in the registrant's internal control over financial reporting that occurred during the registrant's most recent fiscal
quarter (the registrant's fourth fiscal quarter in the case of an annual report) that has materially affected, or is reasonably likely to materially affect, the
registrant's internal control over financial reporting; and

5.  The  registrant's  other  certifying  officer  and  I  have  disclosed,  based  on  our  most  recent  evaluation  of  internal  control  over  financial  reporting,  to  the

registrant's auditors and the audit committee of the registrant's board of directors (or persons performing the equivalent functions):

(a) All significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely

to adversely affect the registrant's ability to record, process, summarize and report financial information; and

(b) Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant's internal control over

financial reporting.

March 15, 2023

/s/ Lawrence F. Metz
Lawrence F. Metz 
President and Co-Chief Executive Officer

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
I, Patrick J. Haveron, certify that:

1. 

I have reviewed this annual report on Form 10-K of Maiden Holdings, Ltd.;

CERTIFICATION

EXHIBIT 31.2

2.  Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements

made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report;

3.  Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial

condition, results of operations and cash flows of the registrant as of, and for, the periods presented in this report;

4.  The registrant's other certifying officer and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Exchange Act
Rules 13a-15(e) and 15d-15(e)) and internal control over financial reporting (as defined in Exchange Act Rules 13a-15(f) and 15d-15(f)) for the registrant
and have:

(a) Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure
that  material  information  relating  to  the  registrant,  including  any  consolidated  subsidiaries,  is  made  known  to  us  by  others  within  those  entities,
particularly during the period in which this report is being prepared;

(b) Designed such internal control over financial reporting, or caused such internal control over financial reporting to be designed under our supervision, to
provide  reasonable  assurance  regarding  the  reliability  of  financial  reporting  and  the  preparation  of  financial  statements  for  external  purposes  in
accordance with generally accepted accounting principles.

(c) Evaluated the effectiveness of the registrant's disclosure controls and procedures and presented in this report our conclusions about the effectiveness of

the disclosure controls and procedures, as of the end of the period covered by this report based on such evaluation; and

(d) Disclosed in this report any change in the registrant's internal control over financial reporting that occurred during the registrant's most recent fiscal
quarter (the registrant's fourth fiscal quarter in the case of an annual report) that has materially affected, or is reasonably likely to materially affect, the
registrant's internal control over financial reporting; and

5.  The  registrant's  other  certifying  officer  and  I  have  disclosed,  based  on  our  most  recent  evaluation  of  internal  control  over  financial  reporting,  to  the

registrant's auditors and the audit committee of the registrant's board of directors (or persons performing the equivalent functions):

(a) All significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely

to adversely affect the registrant's ability to record, process, summarize and report financial information; and

(b) Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant's internal control over

financial reporting.

March 15, 2023

/s/ Patrick J. Haveron
Patrick J. Haveron
Co-Chief Executive Officer and Chief Financial Officer

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
CERTIFICATION

Exhibit 32.1

Pursuant  to  Section  906  of  the  Sarbanes-Oxley  Act  of  2002  (subsections  (a)  and  (b)  of  Section  1350,  chapter  63  of  title  18,  United  States  Code),  the

undersigned officer of Maiden Holdings, Ltd. (the “Company”), hereby certifies, to such officer's knowledge, that:

The Company's Annual Report on Form 10-K for the year ended December 31, 2022 (the “Report”) fully complies with the requirements of Section 13(a) or
15(d)  of  the  Securities  Exchange  Act  of  1934  and  the  information  contained  in  the  Report  fairly  presents,  in  all  material  respects,  the  financial  condition  and
results of operations of the Company.

March 15, 2023

By:  

/s/ Lawrence F. Metz
Lawrence F. Metz 
President and Co-Chief Executive Officer

The  foregoing  certification  is  being  furnished  solely  pursuant  to  Section  906  of  the  Sarbanes-Oxley  Act  of  2002  (subsections  (a)  and  (b)  of  Section  1350,

chapter 63 of title 18, United States Code) and is not being filed as part of the Report.

 
 
 
 
 
 
 
 
 
 
 
CERTIFICATION

Exhibit 32.2

Pursuant  to  Section  906  of  the  Sarbanes-Oxley  Act  of  2002  (subsections  (a)  and  (b)  of  Section  1350,  chapter  63  of  title  18,  United  States  Code),  the

undersigned officer of Maiden Holdings, Ltd. (the “Company”), hereby certifies, to such officer's knowledge, that:

The Company's Annual Report on Form 10-K for the year ended December 31, 2022 (the “Report”) fully complies with the requirements of Section 13(a) or
15(d)  of  the  Securities  Exchange  Act  of  1934  and  the  information  contained  in  the  Report  fairly  presents,  in  all  material  respects,  the  financial  condition  and
results of operations of the Company.

March 15, 2023

By:  

/s/ Patrick J. Haveron
Patrick J. Haveron
Co-Chief Executive Officer and Chief Financial Officer

The  foregoing  certification  is  being  furnished  solely  pursuant  to  Section  906  of  the  Sarbanes-Oxley  Act  of  2002  (subsections  (a)  and  (b)  of  Section  1350,

chapter 63 of title 18, United States Code) and is not being filed as part of the Report.