This Proxy Statement and the accompanying form of proxy are furnished to you and ~~the~~ other holders of the 8.25% Non-Cumulative Preference Shares Series A, 7.125% Non-Cumulative Preference Shares Series C and/or 6.7% Non-Cumulative Preference Shares Series D (all three series of preference shares are collectively referred to in this Proxy Statement as the “Preference Shareholders” or "shareholders)shareholders of Maiden Holdings, Ltd. (“Maiden Holdings,” “Company,” “our,” “us,” or “we”) on behalf of our board of directors (the “Board” or the “Board of Directors”) for use at the ~~Special~~Annual General Meeting ~~of Preference Shareholders (the “Special Meeting” or the “Meeting”), who will be voting together as a single class on the matter described herein,~~ to be held ~~as a virtual meeting via webcast which can be accessed directly~~ at ~~https://shareholder.maiden.bm~~Rosewood Bermuda, 60 Tucker's Point Drive, Hamilton Parish HS 02, Bermuda on ~~Tuesday, December 15, 2020,~~Wednesday, May 3, 2023, at 9:3:00 ~~a.m. (Eastern~~p.m. (Atlantic Daylight Time) and any adjournment or postponement thereof. Due to the public health impact of the COVID-19 pandemic and to support the health and well-being of its shareholders, employees and directors, as well as their families and communities, the decision was made to conduct a virtual meeting via webcast. While shareholders will not have an opportunity to attend the Special Meeting in person, allAll shareholders are entitled and encouraged to attend the ~~virtual Special Meeting. Due to the change~~Annual General Meeting in ~~format, only the formal business of the Special Meeting will be conducted.~~person.

All expenses in connection with this solicitation of proxies will be paid by us. Proxies will be solicited principally by mail, but directors, officers and certain other individuals authorized by us may personally solicit proxies. We will reimburse custodians, nominees or other persons for their out-of-pocket expenses in sending proxy material to beneficial owners.

This Proxy Statement, together with the accompanying proxy card, was first mailed to shareholders entitled to vote at the ~~Special~~Annual General Meeting on or about ~~November 6, 2020.~~March 30, 2023.

As of ~~November 2, 2020,~~March 15, 2023, the only business we expect to be presented at the ~~Special~~Annual General Meeting ~~is the~~is:

The Board has fixed the close of business on ~~November 2, 2020~~March 15, 2023 as the record date for determining the holders of ~~Preference~~Common Shares entitled to notice of and to vote on the applicable matters to be voted upon by such holders of ~~Preference~~Common Shares ~~as applicable,~~ for the ~~Special~~Annual General Meeting. Voting closes at 5:00 p.m. (Eastern Daylight Time) on ~~December 14, 2020.~~May 2, 2023.

As of the record date, there were ~~18,600,000~~142,971,499 outstanding ~~Preference~~Common Shares entitled to one vote per share on the ~~one item~~three items referenced ~~above under "Matters~~above. The voting power of Maiden Reinsurance Ltd., a wholly owned subsidiary of the Company, with respect to ~~Be Voted Upon -~~ ~~Preference~~its investment in Maiden Holdings Common Shares,". will be capped at 9.5% pursuant to the bye-laws of the Company.

Only holders of record of ~~Preference~~Common Shares at the close of business on ~~November 2, 2020~~March 15, 2023 are entitled to vote at the ~~Special~~Annual General Meeting or at any adjournment or postponement of the Meeting. Each ~~Preference~~Common Share that you own entitles you to one vote on the ~~matter of the election of two directors~~matters which are to be voted upon ~~only~~ by holders of ~~Preference~~Common Shares.

If you are a shareholder of record, you may vote by mailing a completed proxy card. To vote by mailing a proxy card, please sign and return the enclosed proxy card in the enclosed prepaid and self-addressed envelope and your shares will be voted at the ~~Special~~Annual General Meeting in the manner you directed.

If ~~your Preference~~you are the beneficial owner of Common Shares ~~are~~ held in street name, ~~and~~ you ~~wish to cast your vote yourself at the Special Meeting, you must obtain a proxy issued in your name~~will receive instructions from your bank or broker that must be followed for such bank or broker to vote your shares per your instructions. Your bank or broker will not have discretion to vote uninstructed shares on Proposals 1, 2, 3 and ~~submit~~4. Thus, if you hold your shares in street name and do not instruct your bank or broker how to vote ~~prior~~on Proposals 1, 2, 3 and 4, no votes will be cast on your behalf with respect to such matter (a “broker non-vote”). Your bank or broker will, however, have discretion to vote uninstructed shares on the ~~Meeting.~~appointment of Ernst & Young LLP as the Company’s independent registered public accounting firm for the 2023 fiscal year. Please ensure that you complete the voting instruction card sent by your bank or broker.

All proxies delivered pursuant to this solicitation are revocable at any time before they are exercised at the option of the persons submitting them by giving written notice to the Corporate Secretary, Maiden Holdings, Ltd., Ideation House, ~~2nd~~1st Floor, 94 Pitts Bay Road, Pembroke HM 08, Bermuda, by submitting a later-dated proxy by mail. If your shares are held in a brokerage account, you must make arrangements with your broker or bank to revoke your proxy.

Two or more persons present by proxy in excess of 50% of the total issued voting ~~Preference~~Common Shares of the Company will constitute a quorum for the transaction of business at the ~~Special~~Annual General Meeting. Shareholder abstentions and broker non-votes will be included in the number of shareholders present at the ~~Special~~Annual General Meeting for the purpose of determining the presence of a quorum.

If within 30 minutes from the time appointed for the Meeting a quorum of ~~Preference~~Common Shares is not present, the Meeting shall stand adjourned to the same day one week later, at the same time and place or to such other day, time or place as the Corporate Secretary may determine. Unless the Meeting is adjourned to a specific date, place and time announced at the Meeting being adjourned, fresh notice of the date, place and time for the resumption of the adjourned Meeting shall be given to each shareholder entitled to attend and vote thereat.

Under our bye-laws, any question proposed for the consideration of the shareholders at any general meeting shall be decided by the affirmative votes of a majority of the votes cast “For” or “Against” the proposal by the holders of ~~Preference~~Common Shares of the Company for ~~the matter~~matters to be voted upon by holders of record of ~~Preference~~Common Shares.

All ~~Preference~~Common Shares represented by properly executed proxies received pursuant to this solicitation will be voted in accordance with the shareholder’s directions specified on the proxy:

In voting by proxy with regard to the election of directors, ~~holders of Preference Shares~~shareholders may vote in favor of each nominee or withhold their votes as to each nominee. Should any nominee become unable to accept nomination or election, the proxy holders named in the proxy card will vote for the election of such other person as a director as the present directors may recommend in the place of such nominee. Abstentions and broker non-votes will have no effect on the election of directors.

You may vote to approve, on an advisory basis, the frequency of the advisory vote on the compensation of our named executive officers every one, two or three years, or you may abstain from voting. The frequency of holding the advisory vote on the compensation of our named executive officers will be decided by a plurality of the votes validly cast, although such vote will not be binding on us. Abstentions and broker non-votes will have no effect on this proposal.

In connection with any other business that may properly come before the ~~Special~~Annual General Meeting, all properly executed proxies delivered pursuant to this solicitation and not revoked will be voted for you in the discretion of the proxy holders named in the proxy card.

A shareholder signing and returning the accompanying proxy has the power to revoke it at any time prior to its exercise by giving written notice of revocation to our Corporate Secretary by submitting a proxy bearing a later date. If your shares are held in a brokerage account, you must make arrangements with your broker or bank to revoke your proxy.

A list of registered ~~preference~~common shareholders as of the close of business on ~~November 2, 2020~~March 15, 2023 will be available for examination by any ~~Preference Shareholder~~common shareholder during normal business hours through ~~December 14, 2020,~~May 2, 2023, at the principal executive offices of the Company, at Ideation House, ~~2nd~~1st Floor, 94 Pitts Bay Road, Pembroke HM 08, Bermuda.

Our Board of Directors currently consists of nine directors; these nine directors will be elected at the Annual General Meeting, each to serve until the 2024 Annual General Meeting of Shareholders and until the election or appointment and qualification of his or her successor, or until his or her earlier death, resignation or removal.

Upon unanimous recommendation of the Nominating and Corporate Governance Committee, the Board of Directors has unanimously nominated as directors: Mr. Barry D. Zyskind, Ms. Holly L. Blanchard and Messrs. Patrick J. Haveron, Simcha G. Lyons, Lawrence F. Metz, Raymond M. Neff, Yehuda L. Neuberger, Steven H. Nigro and Keith A. Thomas for election at the Annual General Meeting. Proxies for holders of Common Shares cannot be voted for more than nine director nominees.

In selecting Mr. Zyskind as a director nominee, our Nominating and Corporate Governance Committee and Board of Directors considered Mr. Zyskind's outside board service and business activities, including his significant executive experience in international business operations, his finance, strategic planning and information technology expertise and his knowledge of the insurance industry.

In selecting Ms. Blanchard as a director nominee, our Nominating and Corporate Governance Committee and Board of Directors considered Ms. Blanchard's extensive insurance regulatory experience and expertise as well as her outside board service and business activities.

In selecting Mr. Haveron as a director nominee, our Nominating and Corporate Governance Committee and Board of Directors considered Mr. Haveron’s leadership role as the Company’s co-chief executive officer and chief financial officer, his being a significant stakeholder developing and implementing the forward strategy and success of the Company, and his past directorship experience in both public and private companies in our industry.

In selecting Mr. Lyons as a director nominee, our Nominating and Corporate Governance Committee and Board of Directors considered Mr. Lyons' outside business activities, including his extensive understanding of governmental and legal affairs and significant executive and finance experience.

In selecting Mr. Metz as a director nominee, our Nominating and Corporate Governance Committee and Board of Directors considered Mr. Metz’s leadership role as the Company’s president and co-chief executive officer, his being a significant stakeholder developing and implementing the forward strategy and success of the Company, and his almost twenty years of experience in executive management at public companies.

In selecting Mr. Neff as a director nominee, our Nominating and Corporate Governance Committee and Board of Directors considered Mr. Neff's deep understanding of the insurance industry, as well as his business activities and significant executive and finance experience.

In selecting Mr. Neuberger as a director nominee, our Nominating and Corporate Governance Committee and Board of Directors considered Mr. Neuberger's business activities and significant executive and finance knowledge. In addition, our Nominating and Corporate Governance Committee and Board of ~~Syncora Holdings Ltd.~~Directors values Mr. Neuberger's extensive experience as a lawyer and ~~led~~as a director of other companies.

In selecting Mr. Nigro as a director nominee, our Nominating and Corporate Governance Committee and Board of Directors considered Mr. Nigro's extensive experience in the finance sector and his deep understanding of the insurance industry. Mr. Nigro's experience as a certified public accountant and an investment banker specializing in the insurance industry is valuable to our Nominating and Corporate Governance Committee and Board of Directors.

In selecting Mr. Thomas as a director nominee, our Nominating and Corporate Governance Committee and Board of Directors considered Mr. Thomas' significant experience in capital markets, financing, investments and marketing.

Ms. Blanchard and Messrs. Lyons, Neff, Nigro and Thomas are “independent directors” under the rules of the NASDAQ Capital Market ("NASDAQ") and the New York Stock Exchange ("NYSE"). The NASDAQ and the NYSE rules require that a majority of the Board of Directors be independent, and we are in compliance with these requirements. The independent directors held separate executive sessions without senior management on at least four occasions in 2022, and neither the chairman, co-chief executive officers nor any member of management, at any level, attended any of the executive sessions of the independent directors.

The Board of Directors held ~~six~~four meetings in ~~2019.~~2022. Each director attended at least 75% of the aggregate of the total number of meetings held in ~~2019~~2022 of the Board and any committee on which he or she served. All directors are expected to make every effort to attend the Annual General Meeting, and each director attended the ~~2020~~2022 Annual General ~~Meeting.~~Meeting of Shareholders.

Our Board of Directors has established an Audit Committee, a Compensation Committee and a Nominating and Corporate Governance Committee, each comprised entirely of independent directors within the meaning of the rules of the NASDAQ ~~Capital Market ("NASDAQ")~~ and the ~~New York Stock Exchange.~~

We have adopted a policy that requires that all related party transactions be approved by our Audit Committee. At each quarterly meeting, each member of the Board is requested to disclose if any related party relationship may have commenced, ceased or changed since the prior meeting. In response to an annual questionnaire, we require directors, director nominees and executive officers to submit a description of any current or proposed related party transaction and provides updates at least quarterly during the year. In addition, we will provide the Audit Committee any similar available information with respect to any known transactions with beneficial owners of 5% or more of our voting securities. If management becomes aware of any potential transactions, management presents such transactions for approval by the Audit Committee. In the event management becomes aware of any transaction that was not approved under the policy, management will present the transaction to the Audit Committee for its action as soon as reasonably practicable, which may include termination, amendment or ratification of the transaction. The Audit Committee will approve only those transactions that are in, or are not inconsistent with, the best interests of the Company and our shareholders, as is determined in good faith in accordance with its business judgment. Each of these related party transactions was approved by our Audit Committee.

Mr. Nigro is the chair of our Audit Committee and the other members are Ms. Blanchard and Messrs. Lyons and Neff. All the members of the Audit Committee are financially literate as well as independent both under SEC rules and as that term is

During 2022, the Audit Committee met five times.

Shareholders and ~~Securities Corp. and is on the Leadership Counsel for the National Small Business Association. Ms. Blanchard also is active in multiple committees and sub-committees~~other interested parties may communicate with members of ~~the National Association of Insurance Commissioners and she presents at National Trade Organization conferences frequently as a subject matter expert in varied insurance topics.~~

Section 16(a) of ~~governmental~~the Exchange Act requires officers, directors and ~~legal affairs~~persons who own more than ten (10) percent of a class of equity securities registered pursuant to Section 12 of the Exchange Act to file reports of ownership and ~~significant executive~~changes in ownership with both the SEC and ~~finance experience.~~the principal exchange upon which such securities are traded or quoted. Officers, directors and persons holding greater than ten (10) percent of the outstanding shares of a class of Section 12-registered equity securities (“Reporting Persons”) are also required to furnish copies of any such reports filed pursuant to Section 16(a) of the Exchange Act with the Company. Based solely on a review of the copies of such forms furnished to the Company and written representations that no other reports were required, the Company believes that from January 1, 2022 to December 31, 2022 all Section 16(a) filing requirements applicable to its Reporting Persons except for once were complied with in a timely manner.

The Board of Directors ~~since December 2019,~~has the ultimate oversight responsibility for the risk management function of the Company. The Company has implemented an enterprise-wide approach to risk management and has ~~served as President~~established an Enterprise Risk Management Committee (the “ERMC”) which consists of members of the Company's senior management. The ERMC oversees the Company's framework for the identification, assessment, measurement, and ~~Co-Chief Executive~~reporting of and management of exposure to the Company's risk on an enterprise-wide basis. Our Audit Committee receives at least quarterly enterprise risk management overview from executive management, and detailed reports from our Chief Risk Officer, which includes updates on areas including insurance risk, operational/strategic risk, financial risk (including investment and liquidity risks), legal/compliance risk, and emerging risks.

The Company has separated the positions of Co-Chief Executive Officers and ~~is also chairman~~Chairman of the Board. This separation enhances Board administration and communication, allows for consistent Board leadership and allows the Co-Chief Executive Officers to focus on managing the Company.

Our Compensation Committee has reviewed our material compensation policies and practices applicable to our employees, including our named executive officers, and concluded that these policies and practices do not create risks that are reasonably likely to have a material adverse effect on us. Our Compensation Committee assessed the Company's compensation and benefits programs to determine if the programs' provisions and operations create undesired or a director of several of our wholly owned subsidiaries. From 2007 to 2009, Mr. Metz served as Vice President, General Counsel - US Operations and Assistant Secretary of AmTrust. From 2004 to 2007, Mr. Metz served as Vice President, General Counsel and Secretaryunintentional risk of a ~~publicly-traded provider~~material nature. We do not have any programs where the ability of ~~information management~~a participant may directly affect variability of payout. Rather, we support the use of base salary, performance-based compensation, and ~~business process optimization solutions. Mr. Metz holds a B.S. from the University of Wisconsin - Madison~~retirement plans that are generally uniform in design and a J.D. from Fordham University School of Law. Mr. Metz serves on the Board of Overseers of the RAND Institute for Civil Justice, and formerly served as the Chair and Vice Chair of the Legal Subcommittee of the Legal and Government Affairs Committee of the Property Casualty Insurers Association of America, and also formerly served on the Board of Advisors of the RAND Center for Corporate Ethics and Governance.

~~Raymond M. Neff~~, 79, has been a member of our Board of Directors since June 2007, and he currently serves as Chairman of the Audit Committee and as a member of the Compensation Committee. He is also chairman of Sabal Palm Bank since 2007, chairman and CEO of Beacon Aviation Insurance Services since 2010, andBased on the ~~board of directors of the not-for-profit Sarasota Gulf Coast CEO Forum. Since 1999, Mr. Neff has served as President of Neff & Associates, Inc.~~foregoing, we believe that our compensation policies and ~~Insurance Home Office Services, LLC. He previously worked at the FCCI Insurance Group from 1986~~practices do not create inappropriate or unintended significant risk to 1999, most recently as President and Chief Executive Officer from 1987 to 1999. He was previously Chairman of the Board of the Florida Workers' Compensation Joint Underwriting Association. Mr. Neff has held various positions at the Department of Labor and Employment Security and the Department of Insurance for the State of Florida. Mr. Neff previously worked at an insurance consulting group, a multi-line insurance agency and the Department of Insurance for the State of Michigan. Mr. Neff holds a B.S. in Mathematics and Accounting from Central Michigan University and an M.A. in Actuarial Science from the University of Michigan. Mr. Neff is a Member of the American Academy of Actuaries and an Associate of the Society of Actuaries.

We do not maintain change in control agreements with any of our named executive officers and none of our equity awards vest upon a change in control of the Company. We do not provide for severance benefits for any of our named executive officers.

In ~~2019,~~2022, we paid an annual retainer of $100,000 to each non-employee director of the Company. We also reimbursed our directors for reasonable expenses they incur in attending meetings of the Board of Directors or any of its committees. Directors may also be eligible in the future for awards under the Plan. Employee directors received no compensation for service on the Board of Directors or any board committee. For his service as Lead Independent Director, Mr. Nigro received an additional annual cash retainer of $20,000.

Starting in fiscal year 2019, the Company ~~has~~ changed its practice of awarding a fixed number of restricted share units to the non-employee directors and ~~instead intends to grant~~currently grants such directors $65,000 worth of compensation in the form of either restricted shares, ~~stock~~share options or cash. For ~~2019 ,~~2022, the compensation was granted in the form of ~~cash~~restricted shares issued to each ~~director.~~director except for Mr. Neuberger as discussed below. It is the Company's intention that annually, on or around June 1, each non-employee director will receive a grant of $65,000 worth of compensation which, if non-cash compensation, will vest on the first anniversary of the ~~grant.~~grant date. For his service as Lead Independent Director, Mr. Nigro will receive (in addition to the $20,000 additional annual cash retainer mentioned above) an additional $10,000 worth of compensation, on or around June 1, in the form of either restricted shares, ~~stock~~share options or cash.

On March 18, 2021, the Compensation Committee approved the disposition of Mr. Neuberger's restricted shares and share options in order to comply with restrictions on investments imposed in connection with his spouse's government service. His compensation continues to be paid in cash for annual retainer and board fees due to him in respect of his services to the Board.

Mr. Zyskind has never accepted a retainer, any Board of Directors or committee fees or any options or other equity-based awards for his service as non-executive Chairman of our Board of Directors.

Conflicts of interest could arise with respect to business opportunities that could be advantageous to any or all of AmTrust or its subsidiaries and the Company or our subsidiaries. In addition, potential conflicts of interest may arise should the interests of AmTrust and/or the Company diverge. From time to time, AmTrust and/or the Company may be presented with opportunities to insure, reinsure or acquire the same book of business. Because of the overlaps between our and AmTrust's shareholders, the Company and AmTrust have agreed that in such cases, the opportunities will be referred to a committee of independent directors of each company to decide whether that company wishes to pursue the opportunity. Pursuant to its charter, our independent Audit Committee must review and approve in advance or ratify any transaction or relationship of any size in which we and any related party have a direct or indirect material interest. The Audit Committee will consider all of the relevant facts and circumstances including (if applicable), but not limited to, (i) the benefits to us; (ii) the impact on a director's independence in the event the related person is a director, a director's immediate family member or an entity in which a director is a partner, shareholder or executive officer; (iii) the availability of other sources for comparable products or services; (iv) the terms of the transaction; and (v) the terms available to unrelated third parties or to employees generally. When considering these factors, the Audit ~~Committee’s review, approval or ratification of transactions~~Committee members will apply their business judgment based upon all relevant facts and circumstances known at that time, in accordance with ~~related persons.~~their fiduciary duties to our shareholders.

The approval of the Increase in Authorized requires the affirmative vote of a majority of the shares of the votes cast of the voting shares present in person or represented by proxy at the Meeting.

The Board of Directors has approved the Increase in Authorized pursuant to which the authorized shares of the Company from US$1,500,000 divided into 150,000,000 shares of par value US$0.01 each, to US$2,000,000 divided into 200,000,000 shares of par value US$0.01 each.

The Board of Directors believes that the Increased in Authorized is desirable to make available shares for future issuance by allowing us greater flexibility with respect to general corporate purposes and in considering potential future actions involving the issuance of common shares, including, without limitation, raising capital, acquisitions of companies or assets, for strategic transactions, sales of shares or securities convertible into common shares, share dividends or splits, and potentially providing equity incentives to employees, officers and directors. The Board of Directors also believes that the Increase in Authorized would be desirable to make additional unreserved common shares available for issuance or reservation without further shareholder authorization, except as may be required by law or by the rules of NASDAQ. For example, the NASDAQ Marketplace Rules requires shareholder approval as a prerequisite to approval of applications to list additional common shares to be issued where the present or potential issuance of common shares (or securities convertible into common shares) could result in an increase in outstanding common shares of 20% or more.

Authorizing the Company to issue more shares than currently authorized will not affect materially any substantive rights, powers or privileges of the holders of shares of common shares. Holders of common shares are entitled to one vote per share on all matters submitted to the shareholders and do not have cumulative voting rights or pre-emptive rights for the purchase of additional shares of any class of share capital. The additional common shares for which authorization is sought are identical to the common shares now authorized. However, the issuance of additional common shares may, among other things, have a dilutive effect on the earnings per share and on equity and voting power of existing shareholders and adversely affect the market price for common shares. Although the Board of Directors has no present intention of issuing any additional common shares, the proposed increase in the number of authorized common shares could enable the Board of Directors to render more difficult or discourage an attempt by another person or entity to obtain control of the Company. However, we do not view the Increase in Authorized as part of an “anti-takeover” strategy. The Increase in Authorized is not being advanced because of any known effort by any party to accumulate common shares or to obtain control of the Company. The Board of Directors also could, although it has no present intention of so doing, authorize the issuance of common shares to a holder who might thereby obtain sufficient voting power to assure that any proposal to effect certain business combinations or amendment to the Memorandum of Association or Bye-laws would not receive the required shareholder approval.

The Company believes that the availability of the additional common shares will provide us with the flexibility to meet business needs as they arise, to take advantage of favorable opportunities and to respond to a changing corporate environment. If we issue additional shares, the ownership interests of holders of the common shares will be diluted.

Under Bermuda law, the appointment of our auditors is a decision to be made by the shareholders. Deloitte Ltd. (“Deloitte”) served as the Company's independent registered public accounting firm for each of our 2019 and 2018 fiscal years. On May 18, 2020, Deloitte resigned as the Company’s independent registered public accounting firm.

(i) the application of accounting principles to a specified transaction, either completed or proposed, or the type of audit opinion that might be rendered on the Company’s consolidated financial statements, and neither a written report was provided to the Company nor oral advice was provided to the Company that Ernst & Young LLP ~~concluded~~ was ~~an important factor considered by the Company in reaching a decision as to the accounting, auditing or financial reporting issue; or~~

The following table presents the aggregate fees billed for professional services rendered to us by ~~Deloitte Ltd. and BDO USA, LLP~~our independent registered public accounting firms for our fiscal years ended December 31, ~~2019~~2022 and ~~2018:~~2021:

We and our Audit Committee are committed to ensuring the independence of our auditors, both in fact and in appearance.

The Audit Committee may form and delegate to a subcommittee consisting of one or more members (provided that such person(s) are independent directors) its authority to grant pre-approvals of audit, permitted non-audit services and internal control-related services, provided that decisions of such subcommittee to grant pre-approvals shall be presented to the full Audit Committee at its next scheduled meeting.

The Audit Committee pre-approved all fees in the period from January 1, ~~2019~~2022 through December 31, ~~2019.~~2022.

A proposal by a shareholder intended for inclusion in our proxy materials for the ~~2021~~2024 Annual General Meeting of Shareholders pursuant to Rule 14a-8 of the Exchange Act must be received by our Corporate Secretary, Ideation House, ~~2nd~~1st Floor, 94 Pitts Bay Road, Pembroke HM 08, Bermuda on or before ~~December 7, 2020~~November 30, 2023 in order to be considered for such inclusion. Shareholder proposals intended to be submitted at the ~~2021~~2024 Annual General Meeting of Shareholders outside the framework of Rule 14a-8 must be received on or before February ~~26, 2021~~13, 2024 to be considered timely under Rule 14a-4(c)(1). If we do not receive notice of the matter by the applicable date, the proxy holders will vote on the matter, if properly presented at the Meeting, in their discretion.


Name and Address of Beneficial Owner	Amount and Nature of Beneficial Ownership		Percent of Class
Barry D. Zyskind, c/o Maiden Holdings, Ltd. Ideation House, 2nd Floor, 94 Pitts Bay Road, Pembroke HM08, Bermuda	6,374,292	(1)	7.4	%
Leah Karfunkel c/o Maiden Holdings, Ltd. Ideation House, 2nd Floor, 94 Pitts Bay Road, Pembroke HM08, Bermuda	6,792,600	(2)	7.9	%
683 Capital Partners, LP 3 Columbus Circle, Suite 2205, New York, NY 10019	7,876,964	(3)	9.1	%
Dimensional Fund Advisors LP Building One, 6300 Bee Cave Road, Austin, TX 78746	5,412,423	(4)	6.3	%
Talkot Capital, LLC 30 Liberty Ship Way, Suite 3110, Sausalito, CA 94965	7,715,816	(5)	8.9	%
Phillips Ray Capital Management, Inc. (“PRCM”), 3707 Camp Bowie Blvd., Suite 250, Fort Worth, TX 76107	6,006,044	(6)	7.0	%


Name and Address of Beneficial Owner	Amount and Nature of Beneficial Ownership		Percent of Class




Maiden Reinsurance Ltd. 159 Bank Street, 4th Floor, Burlington, VT 05401	41,439,348	(1)	29.0	%
Talkot Capital, LLC 30 Liberty Ship Way, Suite 3110, Sausalito, CA 94965	12,892,842	(2)	9.0	%
Phillips Ray Capital Management, Inc. 2727 W 7th Street, Suite 220, Fort Worth, TX 76107	8,198,599	(3)	5.7	%


Name of Beneficial Owner**	Name of Beneficial Owner**	Amount & Nature of Beneficial Ownership		Percent of Class(1)	Name of Beneficial Owner**	Amount & Nature of Beneficial Ownership		Percent of Class(1)
Barry D. Zyskind	Barry D. Zyskind	6,374,292	(2)	7.4%	Barry D. Zyskind	6,374,292	(2)	4.5%
Holly L. Blanchard	Holly L. Blanchard	54,166	(3)	*	Holly L. Blanchard	99,270	(3)	*

Patrick J. Haveron					Patrick J. Haveron	2,084,774	(4)	1.5
William T. Jarman					William T. Jarman	209,505	(5)	*

Simcha G. Lyons	Simcha G. Lyons	156,336	(4)	*	Simcha G. Lyons	215,525	(6)	*
Lawrence F. Metz					Lawrence F. Metz	1,556,699	(7)	1.1
Raymond M. Neff	Raymond M. Neff	568,666	(5)	*	Raymond M. Neff	636,210	(8)	*
Yehuda L. Neuberger	Yehuda L. Neuberger	367,166	(6)	*	Yehuda L. Neuberger	277,000	(9)	*
Steven H. Nigro	Steven H. Nigro	139,000	(7)	*	Steven H. Nigro	206,043	(10)	*
Keith A. Thomas	Keith A. Thomas	100,000	(8)	*	Keith A. Thomas	100,104	(11)	*
Lawrence F. Metz		1,199,416	(9)	1.4%
Patrick J. Haveron		1,584,798	(10)	1.8%
William T. Jarman		156,175	(11)	*
All executive officers and directors as a group (10 persons)	All executive officers and directors as a group (10 persons)	10,700,015		12.4%	All executive officers and directors as a group (10 persons)	11,759,422		8.2%


Board Diversity Matrix	Female	Male
Total Number of Directors	9
Part I. Gender Identity
Directors	1	8
Part II. Demographic Background
African American or Black	—	1
White	1	7


Name and Principal Position	Year	Salary		Bonus			Stock Awards			Option Awards		Non-Equity Incentive Plan Compensation		All Other Compensation			Total
Lawrence F. Metz President and Co-Chief Executive Officer, Maiden Holdings, Ltd.	2019	$	725,000	$	100,000	(1)	$	500,000	(3)	$	—	$	—	$	126,661	(5)	$	1,451,661
	2018	$	547,913	$	250,000	(2)	$	1,230,950	(4)	$	—	$	—	$	22,158	(5)	$	2,051,021
Patrick J. Haveron Co-Chief Executive Officer and Chief Financial Officer, Maiden Holdings, Ltd.	2019	$	697,917	$	100,000	(1)	$	750,000	(6)	$	—	$	—	$	334,413	(8)	$	1,882,330
	2018	$	543,600	$	250,000	(2)	$	665,965	(7)	$	—	$	—	$	284,101	(8)	$	1,743,666
William T. Jarman Senior Vice President, Chief Actuary and Chief Risk Officer, Maiden Global Servicing Company, LLC	2019	$	423,500	$	100,000	(1)	$	—		$	—	$	—	$	118,215	(9)	$	641,715
	2018	$	417,133	$	150,000	(2)	$	169,400	(10)	$	—	$	—	$	247,044	(9)	$	983,577


						By Order of the Board of Directors,

						Lawrence F. Metz President and Co-Chief Executive Officer


(1)			Amount shown reflects discretionary cash awards for Executive's performance during that year granted in the ~~second~~first quarter of the following year.
(2)			~~Amount shown reflects~~Represents the aggregate grant date fair market value of discretionary ~~cash~~performance-based restricted share awards granted to the named executive officer as determined in accordance with Accounting Standards Codification Topic No. 718, "Compensation Stock Discussion," using the assumptions described in Note 14 to the Financial Statements included in our Annual Report on Form 10-K filed with the SEC on March 15, 2023. At the discretion of the Compensation Committee on March 15, 2022, Messrs. Metz and Haveron were each granted 362,351 restricted shares with immediate vesting. The value of the restricted shares at grant date fair market value for ~~Executive's~~Messrs. Metz and Haveron were $923,995 each. (112,745 of those 362,351 shares awarded were based on certain quantitative and qualitative performance ~~during that year granted~~measures in the ~~first quarter~~sole discretion of the ~~following year.~~Compensation Committee).
(3)			Represents the aggregate grant date fair market value of discretionary performance-based restricted share awards granted to the named executive officer as determined in accordance with Accounting Standards Codification Topic No. 718, "Compensation Stock Discussion," using the assumptions described in Note 14 to the Financial Statements included in our Annual Report on Form 10-K filed with the SEC on March 14, 2022. At the discretion of the Compensation Committee on March 3, 2021, Messrs. Metz and Haveron were each granted 661,205 restricted shares with immediate vesting. The value of the restricted shares at grant date fair market value for Messrs. Metz and Haveron were $1,811,702 each. (136,681 of those 661,205 shares awarded were based on certain quantitative and qualitative performance measures in the sole discretion of the Compensation Committee).
(4)			All other compensation amounts disclosed reflect costs related to supplemental allowance and executive life insurance for all three named executive officers. For Mr. Haveron, these amounts also include tax equalization and Bermuda Social Insurance. For Mr. Metz, these amounts also include executive physical, tax equalization and Bermuda Social Insurance. For Mr. Jarman, these amounts also include a work from home allowance and executive physical.
(5)			Represents the aggregate grant date fair market value of non-performance based restricted share awards granted to the named executive officer as determined in accordance with Accounting Standards Codification Topic No. 718, "Compensation Stock Discussion," using the assumptions described in Note 14 to the Financial Statements included in our Annual Report on Form 10-K filed with the SEC on March ~~18, 2020.~~15, 2023. At the discretion of the Compensation Committee on March ~~20, 2019,~~15, 2022, Mr. ~~Metz~~Jarman was granted ~~645,161~~78,431 restricted shares subject to a ~~two year~~two-year vesting ~~with one half vested on the first anniversary of the grant date and one half on the second anniversary of the grant date.~~period. The restricted shares were awarded with voting and dividend rights. The value of the restricted shares at grant date fair market value for Mr. ~~Metz~~Jarman was ~~$500,000.~~
~~(4)~~			Represents the aggregate grant date fair market value of performance based restricted share unit awards granted to the named executive officer as determined in accordance with Accounting Standards Codification Topic No. 718, "Compensation Stock Discussion," using the assumptions described in Note 15 to the Financial Statements included in our Annual Report on Form 10-K filed with the SEC on March 15, 2019. The value of the performance based restricted shares at grant date fair market value in February 2018 was $230,950, but this grant was partially paid out in March 2019 and was retired. At the discretion of the Compensation Committee in August 2018, Mr. Metz was granted 135,135 restricted shares subject to a three year vesting with one third vested on the first anniversary of the grant date, one third on the second anniversary of the grant date and the remaining on the third anniversary of the grant date. The restricted shares were awarded with voting and dividend rights. The value of the restricted shares at grant date fair market value for Mr. Metz was $1,000,000.
~~(5)~~			Amount shown reflects costs related to commuting to our office in Bermuda and related lodging expenses, executive life insurance, car allowance, executive physical, paid dividends for unvested restricted shares and Bermuda Social Insurance.$200,000.
(6)			Represents the aggregate grant date fair market value of non-performance based restricted share awards granted to the named executive officer as determined in accordance with Accounting Standards Codification Topic No. 718, "Compensation Stock Discussion," using the assumptions described in Note 14 to the Financial Statements included in our Annual Report on Form 10-K filed with the SEC on March ~~18, 2020.~~14, 2022. At the discretion of the Compensation Committee on ~~March 20, 2019,~~April 23, 2021, Mr. ~~Haveron~~Jarman was granted ~~967,742~~43,859 restricted shares subject to a ~~two year~~two-year vesting ~~with one half vested on the first anniversary of the grant date and one half on the second anniversary of the grant date.~~period. The restricted shares were awarded with voting and dividend rights. The value of the restricted shares at grant date fair market value for Mr. ~~Haveron was $750,000.~~
~~(7)~~			Represents the aggregate grant date fair market value of performance based restricted share unit awards granted to the named executive officer as determined in accordance with Accounting Standards Codification Topic No. 718, "Compensation Stock Discussion," using the assumptions described in Note 15 to the Financial Statements included in our Annual Report on Form 10-K filed with the SEC on March 15, 2019. The fair market value of the performance based restricted shares at grant date in February 2018 was $260,000, but this grant was partially paid out in March 2019 and was retired. At the discretion of the Compensation Committee in November 2018, Mr. Haveron was granted 111,836 restricted shares subject to a three year vesting with one third vested on the first anniversary of the grant date, one third on the second anniversary of the grant date and the remaining on the third anniversary of the grant date. The restricted shares were awarded with voting and dividend rights. The value of the restricted shares at grant date fair market value for Mr. Haveron was $405,965.
~~(8)~~			Amount shown reflects the costs related to commuting to our office in Bermuda and related lodging expenses, car allowance, tax equalization, executive life insurance, Bermuda Social Insurance and paid dividends for unvested restricted shares.
~~(9)~~			~~Amount shown reflects the costs related to commuting to our office in Bermuda and related lodging expenses, car allowance, executive physical, tax equalization, and executive life insurance.~~
~~(10)~~			Represents the aggregate grant date fair market value of performance based restricted share unit awards granted to the named executive officer as determined in accordance with Accounting Standards Codification Topic No. 718, "Compensation Stock Discussion," using the assumptions described in Note 15 to the Financial Statements included in our Annual Report on Form 10-K filed with the SEC on March 15, 2019. The fair market value of the performance based restricted shares at grant date for Mr. Jarman was $169,400. At the discretion of the Board, Mr. Jarman was granted 2,500 restricted shares subject to a two year vesting with 50% on the first anniversary of the grant date and 50% on the second anniversary of the grant date. The restricted shares were awarded with voting and dividend rights. The fair market value of the restricted shares at grant date for Mr. Jarman was $32,900.$150,000.


		Option Awards				Share Awards								Option Awards				Share Awards
Name	Name	Number of Securities Underlying Unexercised Options Exercisable (1)	Option Exercise Price		Option Expiration Date	Number of Shares or Units of Stock That Have Not Vested Unexercised	Market Value of Shares or Units of Stock That Have Not Vested			Equity Incentive Plan Awards: Number of Unearned Shares, Units or Other Rights That Have Not Vested (5)	Equity Incentive Plan Awards: Market or Payout Value of Unearned Shares, Units or Other Rights That Have Not Vested (4)		Name	Number of Securities Underlying Outstanding Options Exercisable (1)	Option Exercise Price		Option Expiration Date	Number of Shares That Have Not Vested	Market Value of Shares That Have Not Vested			Equity Incentive Plan Awards: Number of Unearned Shares, Units or Other Rights That Have Not Vested	Equity Incentive Plan Awards: Market or Payout Value of Unearned Shares, Units or Other Rights That Have Not Vested
Patrick J. Haveron													Patrick J. Haveron					225,490	$	475,784	(2)	—	$	—
																		225,490	$	475,784	(3)
Lawrence F. Metz	Lawrence F. Metz	50,000	$	7.25	3/4/2020	90,090	$	666,667	(2)	21,484	$	16,113	Lawrence F. Metz		$	—	0	225,490	$	475,784	(2)	—	$	—
						645,161	$	500,000	(3)									225,490	$	475,784	(3)
Patrick J. Haveron		30,000	$	7.25	3/4/2020	74,558	$	270,643	(2)	23,560	$	17,670
						967,742	$	750,000	(3)
William T. Jarman	William T. Jarman	7,500	$	9.42	2/22/2022					14,077	$	10,558	William T. Jarman					43,859	$	92,542	(4)	—	$	—
																		78,431	$	165,489	(5)


(a)	(b)		(b)		(c)		(c)		(d)		(e)		(f)		(g)
Fiscal Year (1)	Summary Compensation Table Total for PEO Mr. Haveron(2)		Summary Compensation Table Total for PEO Mr. Metz(2)		Compensation Actually Paid to PEO Mr. Haveron(3)		Compensation Actually Paid to PEO Mr. Metz(3)		Summary Compensation Table for Non-PEO Named Executive Officer(2)		Compensation Actually Paid to Non-PEO Named Executive Officer(3)		Value of Initial Fixed $100 Investment Based on Total Shareholder Return(4)		Net Income available to Maiden common shareholders (in thousands)
2022	$	2,260,510	$	2,256,139	$	2,177,900	$	2,173,529	$	825,016	$	717,434	$	84.80	$	55,432
2021	$	3,144,062	$	3,143,404	$	2,429,695	$	2,393,403	$	790,700	$	976,975	$	122.90	$	117,643


				Less:		Plus:		Plus (less):
Name	Fiscal Year	SCT Total (a)		SCT Share Awards (b)		Fair Value of Share Awards Granted in the Covered Year (c)		Change in Fair Value of Unvested Share Awards from Covered Years (d)		Fair Value of Share Awards Granted and Vested in the Covered Year (e)		Change in Fair Value of Share Awards from Prior Years that Vested in the Covered Year (f)		Change in Fair Value of Unvested Share Awards from Prior Years (g)		Compensation Actually Paid
PEO Patrick J. Haveron	2022	$	2,260,510	$	(923,995)	$	475,784	$	—	$	575,000	$	(209,399)	$	—	$	2,177,900
	2021	$	3,144,062	$	(1,811,702)	$	558,395	$	—	$	500,000	$	38,940	$	—	$	2,429,695
PEO Lawrence F. Metz	2022	$	2,256,139	$	(923,995)	$	475,784	$	—	$	575,000	$	(209,399)	$	—	$	2,173,529
	2021	$	3,143,404	$	(1,811,702)	$	558,395	$	—	$	500,000	$	3,306	$	—	$	2,393,403
NEO William T. Jarman	2022	$	825,016	$	(200,000)	$	46,209	$	165,257	$	—	$	(77,381)	$	(41,667)	$	717,434
	2021	$	790,700	$	(150,000)	$	202,066	$	—	$	—	$	—	$	134,209	$	976,975


Name	Name	Fees Earned or Paid in Cash (1)		Restricted Shares (2)		Total		Name	Fees Earned or Paid in Cash (1)		Restricted Shares (2)		Total
Barry D. Zyskind	Barry D. Zyskind	$	—	$	—	$	—	Barry D. Zyskind	$	—	$	—	$	—
Holly L. Blanchard	Holly L. Blanchard	5,753		—		5,753		Holly L. Blanchard	100,000		65,000		165,000
Simcha G. Lyons	Simcha G. Lyons	165,000		—		165,000		Simcha G. Lyons	100,000		65,000		165,000
Raymond M. Neff	Raymond M. Neff	165,000		—		165,000		Raymond M. Neff	100,000		65,000		165,000
Yehuda L. Neuberger	Yehuda L. Neuberger	165,000		—		165,000		Yehuda L. Neuberger	165,000		—		165,000
Steven H. Nigro	Steven H. Nigro	195,000		—		195,000		Steven H. Nigro	120,000		75,000		195,000
Keith A. Thomas	Keith A. Thomas	5,753		—		5,753		Keith A. Thomas	100,000		65,000		165,000


Name	Grant Date Fair Value		Stock Awards (1)	Options Outstanding at December 31, 2022
Barry D. Zyskind	$	—	—	—
Holly L. Blanchard	65,000		26,639	—
Simcha G. Lyons	65,000		26,639	24,000
Raymond M. Neff	65,000		26,639	24,000
Yehuda L. Neuberger	—		—	—
Steven H. Nigro	75,000		30,737	18,000
Keith A. Thomas	65,000		26,639	—


	(a)	(b)		(c)
Plan category	Number of securities to be issued upon exercise of outstanding options, warrants and rights	Weighted-average exercise price of outstanding options, warrants and rights		Number of securities remaining available for future issuance under equity compensation plans (excluding securities reflected in column (a))
Equity compensation plans approved by security holders	144,000	$	9.72	7,687,727
Equity compensation plans not approved by security holders	—	—		—
Total	144,000	$	9.72	7,687,727


Filed by the Registrant:			x


Filed by a Party other than the Registrant:			¨