glre-20260424

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934


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Filed by a Party other than the Registrant			o


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ý			Definitive Proxy Statement
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o			Soliciting Material Pursuant to Section 240.14a-12

GREENLIGHT CAPITAL RE, LTD.

(Name of Registrant As Specified in its Charter)

N/A

(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

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GREENLIGHT CAPITAL RE, LTD.

65 Market Street, Suite 1207
Jasmine Court, Camana Bay
P.O. Box 31110
Grand Cayman, KY1-1205
Cayman Islands

NOTICE OF ANNUAL GENERAL MEETING OF SHAREHOLDERS

JULY 28, 2026

Notice is hereby given that the Annual General Meeting of Shareholders, or the Meeting, of Greenlight Capital Re, Ltd., or the Company, will be held at the Company’s offices at 65 Market Street, Suite 1207, Jasmine Court, Camana Bay, Grand Cayman, Cayman Islands on July 28, 2026 at 9:00 a.m. (local time), for the following purposes:

1.To consider and vote upon a proposal to elect eleven (11) directors to serve on the Board of Directors of the Company until the Annual General Meeting of Shareholders of the Company in 2027, or the 2027 Meeting;

2.To consider and vote upon a proposal to ratify the appointment of Deloitte Ltd. as the independent auditors of the Company for the fiscal year ending December 31, 2026;

3.To consider and cast a non-binding advisory vote on a resolution approving the compensation of the Company’s named executive officers as disclosed pursuant to the compensation disclosure rules of the Securities and Exchange Commission; and

4.To transact any other business that may properly come before the Meeting or any adjournment or postponement thereof.

Information concerning the matters to be acted upon at the Meeting is set forth in the accompanying Proxy Statement.

Only shareholders of record, as shown by the transfer books of the Company, at the close of business on May 1, 2026 will be entitled to notice of, and to vote at, the Meeting or any adjournments or postponements thereof.

In accordance with rules adopted by the Securities and Exchange Commission, we are pleased to furnish these proxy materials to shareholders over the Internet rather than in paper form. We believe these rules allow us to provide our shareholders with expedited and convenient access to the information they need, while helping to conserve natural resources and lower the costs of printing and delivering proxy materials.

Whether or not you plan to attend the Meeting, we hope you will vote as soon as possible. Voting your proxy will ensure your representation at the Meeting. We urge you to carefully review the proxy materials and to vote FOR the election of each director nominee named in proposal 1 and FOR proposals 2 and 3.


						By Order of the Board of Directors,
						/s/ David Sigmon
						David Sigmon
						Corporate Secretary
April 24, 2026
Grand Cayman, Cayman Islands

MEETING INFORMATION



DATE	TIME	PLACE
July 28, 2026	9:00 a.m., Local Time	65 Market Street, Suite 1207, Jasmine Court, Camana Bay, Grand Cayman, Cayman Islands

HOW TO VOTE

Your vote is very important. Whether or not you plan to attend the Meeting, we encourage you to read this proxy statement and submit your proxy so that your shares can be voted at the Meeting and to help us ensure a quorum at the Meeting. You may nonetheless vote in person if you attend the Meeting.



IN PERSON	BY PHONE	BY INTERNET	BY MAIL
You may come to the Meeting and cast your vote in person	1-800-690-6903	www.proxyvote.com	Mark, sign and date your proxy card and return it in the postage-paid envelope


			IMPORTANT NOTICE REGARDING THE AVAILABILITY OF PROXY MATERIALS FOR THE SHAREHOLDERS MEETING TO BE HELD ON JULY 28, 2026: THE NOTICE OF ANNUAL MEETING OF SHAREHOLDERS, PROXY STATEMENT AND THE ANNUAL REPORT TO STOCKHOLDERS ARE AVAILABLE AT www.envisionreports.com/GLRE

TABLE OF CONTENTS


			Page
GENERAL INFORMATION			1
PROXY SUMMARY			2
THE COMPANY AT A GLANCE			3
VOTING			8
VOTING SECURITIES AND VOTE REQUIRED			9
SOLICITATION AND REVOCATION			9
PROPOSAL ONE: ELECTION OF DIRECTORS OF THE COMPANY			10
CORPORATE GOVERNANCE AND BOARD OF DIRECTORS AND COMMITTEES			19
DIRECTOR COMPENSATION			27
PROPOSAL TWO: RATIFICATION OF APPOINTMENT OF THE COMPANY’S AUDITORS			28
PROPOSAL THREE: ADVISORY VOTE ON EXECUTIVE COMPENSATION			28
COMPENSATION DISCUSSION AND ANALYSIS			31
SUMMARY COMPENSATION TABLE			43
GRANTS OF PLAN BASED AWARDS IN FISCAL YEAR 2025			44
OUTSTANDING EQUITY AWARDS AT FISCAL YEAR END 2025			48
POTENTIAL PAYMENTS UPON TERMINATION OR CHANGE IN CONTROL			50
PAY RATIO AND PAY VERSUS PERFORMANCE			55
AUDIT COMMITTEE REPORT			62
COMMON SHARE OWNERSHIP BY DIRECTORS AND EXECUTIVE OFFICERS			64
PRINCIPAL BENEFICIAL OWNERS OF COMMON SHARES			65
DELINQUENT SECTION 16(A) REPORTS			65
CERTAIN RELATIONSHIPS AND RELATED-PARTY TRANSACTIONS			66
OTHER MATTERS			68
ADDITIONAL INFORMATION			69
ANNEX 1 - NON-GAAP FINANCIAL MEASURES			72

GREENLIGHT RE

GREENLIGHT CAPITAL RE, LTD.

65 Market Street, Suite 1207, Jasmine Court, Camana Bay

P.O. Box 31110

Grand Cayman, KY1-1205

Cayman Islands

PROXY STATEMENT

ANNUAL GENERAL MEETING OF SHAREHOLDERS
JULY 28, 2026

GENERAL INFORMATION

This Proxy Statement is furnished in connection with the solicitation by the Board of Directors, or our Board, of Greenlight Capital Re, Ltd., or the Company, of proxies for use at the Annual General Meeting of Shareholders of the Company, or the Meeting, to be held at 65 Market Street, Suite 1207, Jasmine Court, Camana Bay, Grand Cayman, Cayman Islands on July 28, 2026 at 9:00 a.m. (local time), and at any and all adjournments or postponements thereof, for the purposes set forth in the accompanying Notice of Annual General Meeting of Shareholders. The Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2025, including consolidated financial statements, or the Annual Report, is included with this Proxy Statement for informational purposes and not as a means of soliciting your proxy. We will furnish any exhibit to our Annual Report at no charge to any shareholder who provides a written request to the Company’s Secretary at the address above. You can also access our filings with the Securities and Exchange Commission, including our Annual Reports and all amendments thereto, at www.sec.gov.

This Proxy Statement and the accompanying proxy card and Notice of Annual General Meeting of Shareholders are first being provided to shareholders on or about May 13, 2026.

Unless otherwise indicated or unless the context otherwise requires, all references in this Proxy Statement to “the Company,” “GLRE,” “we,” “us,” “our,” and similar expressions are references to Greenlight Capital Re, Ltd. (and/or applicable subsidiary). All references to “Greenlight Re” are references to Greenlight Reinsurance, Ltd., a Cayman Islands reinsurer and wholly-owned subsidiary of GLRE. All references to “GRIL” are references to Greenlight Reinsurance Ireland, Designated Activity Company, an Ireland reinsurer and wholly-owned subsidiary of GLRE.

2026 PROXY STATEMENT 1

GREENLIGHT RE

PROXY SUMMARY

This summary highlights certain information in this Proxy Statement and does not contain all the information you should consider in voting your shares. Please refer to the complete Proxy Statement and our Annual Report prior to voting at the Meeting.

Items of Business

The items of business to be addressed at the Meeting are as follows:

1.Elect each of the eleven (11) director nominees to serve on the Company’s Board of Directors until the Annual General Meeting of Shareholders of the Company in 2027, or the 2027 Meeting;

2.Ratify the appointment of Deloitte Ltd., an independent registered public accounting firm, as the Company’s independent auditors for the fiscal year ending December 31, 2026;

3.Conduct a non-binding advisory vote on executive compensation (“Say-on-Pay”); and

4.Transact any other business that may properly come before the Meeting or any adjournment or postponement thereof.

Recommendations of the Board

Our Board recommends that our shareholders take the following actions at the Meeting:


Proposal		Board Voting Recommendation	Page Reference

1	Election of the Company’s Board of Directors	FOR each nominee	10
2	Ratification of Company’s Auditors	FOR	28
3	Advisory Vote on Say-on-Pay	FOR	28

2 2026 PROXY STATEMENT

GREENLIGHT RE

THE COMPANY AT A GLANCE

Overview

The Company provides multiline property and casualty insurance and reinsurance through its licensed and regulated reinsurance entities in the Cayman Islands and Ireland, and its Lloyd's platform, Greenlight Innovation Syndicate 3456. The Company complements its underwriting activities with a non-traditional investment approach designed to achieve higher rates of return over the long term than reinsurance companies that exclusively employ more traditional investment strategies. In 2018, the Company launched its Greenlight Re Innovations unit, which supports technology innovators in the (re)insurance space by providing investment capital, risk capacity, and access to a broad insurance network.

Today, our lean, flexible operating platforms provide global market access from three strategic jurisdictions: the Cayman Islands, Ireland, and the United Kingdom.

The Company’s business is comprised of the following

Strategic Pillars:

Open Market Reinsurance Underwriting

Innovations Underwriting & Investments

Value Orientated Investment Strategy

Primarily follow business with line determined by expertise and market intelligence

Leverage investment to provide optionality to participate in (re)insurance business opportunities

Designed to achieve higher rates of return over the long term than more traditional fixed income investment strategies

Small scale allows consistent review of all risks and dynamic allocation of capacity to best opportunities

Benefit from potential capital appreciation on early stage investments

Low correlation to underwriting

Long-short strategy reduces market exposure

Focus on short- and medium-tail risks where we can compete on similar terms with larger peers

For each investment, we aim to have a high level of influence and option on future business

Liquid portfolio

2026 PROXY STATEMENT 3

GREENLIGHT RE

2025 Financial Highlights

The Company’s financial highlights for 2025 included net income of $74.8 million, compared to $42.8 million in 2024, and gross written premium of $773.3 million, representing a 10.7% increase in gross written premium compared to 2024. The Company’s combined ratio in 2025 was 94.6%, versus 101.4% in 2024, and return on average equity in 2025 was 11.1%, versus 6.9% in 2024.

Over the past five years,

Total Shareholders’ Equity

has steadily increased each year as follows:

(Dollars in Millions)

Compound Annual Growth Rate (CAGR) is calculated from December 31, 2020 ($464.9) through year-end 2025.

The foregoing growth in shareholders’ equity over the past five years demonstrate the strength of our go-forward strategy and dedication and hard work of our employees.1 We continue to prioritize long-term growth in diluted book value per share as a primary financial metric in measuring our Company’s performance, and believe our current strategy positions us for success under this metric. We are also proud that in 2025, international rating agency AM Best upgraded the financial strength rating for our principal operating subsidiaries from “A-” to “A” (Excellent).

1 As of year-end 2025, we had 84 employees across our offices in the Cayman Islands, Ireland and the United Kingdom.

4 2026 PROXY STATEMENT

GREENLIGHT RE

Corporate Governance Highlights

We are committed to good corporate governance, which promotes the long-term interests of shareholders, strengthens Board and management accountability and helps build public trust in the Company. The section entitled “Corporate Governance and Board of Directors and Committees” below describes our corporate governance framework, which includes the following highlights:

•Annual election of directors

•Eight of our eleven director nominees are independent

•Five of our eleven director nominees joined our Board since 2021, with one additional independent director nominee joining in 2026 subject to shareholder approval

•Comprehensive Code of Ethics and Business Conduct and Corporate Governance Guidelines

•Conflict of Interest and Related Party Transaction Policy

•One class of ordinary shares across all shareholders

•Frequent executive sessions of independent members of the Board and Committees

•Separation of the roles of Board Chair, CEO and Lead Independent Director

•Nominating, Governance and Corporate Responsibility Committee participates in executive succession planning

•Directors elected by majority vote

•Annual Board self-assessment process

•Board and Committee review of strategic, operational and compliance risks

•"Whistleblower” hotline

•Ordinary Share Ownership Guidelines for Directors and Named Executive Officers adopted in 2021

•Amended and Restated Insider Trading Policy (including prohibition on hedging and pledging)

•Pay for Performance alignment

•Coordinated investor outreach

•No poison pill

•Clawback Policy for incentive compensation (cash and equity)

Proxy Governance Shareholder Engagement

The Board values engaging regularly with the Company’s shareholders. The Company is committed to ongoing engagement with its stakeholders on all matters that are important to our shareholders, including executive compensation, governance, and board diversity, particularly in the months preceding each Annual General Meeting. We continue to conduct outreach with our top institutional shareholders as well as other shareholders that request engagement.

2026 PROXY STATEMENT 5

GREENLIGHT RE

Corporate Responsibility

Our Nominating, Governance and Corporate Responsibility Committee of our Board has ultimate oversight over our corporate responsibility strategy and practices and is responsible for reporting to the Board periodically on these issues.

Governance

We maintain our Code of Business Conduct and Ethics, or the Code of Ethics, that showcases our Company’s commitment to do the right thing. The Code of Ethics has important guidelines, expectations and information that our employees, officers and directors commit to, which guide their day-to-day business behavior. To further align the values of each company stakeholder, we also maintain an insider trading policy, share ownership and retention policy, conflict of interest and related party policies, clawback policy and corporate governance guidelines. See “Corporate Governance Highlights.”

Employee Engagement & Creation of Core Values

We are committed to employee engagement and enhancing the morale and well-being of our employees. In 2024, we conducted a comprehensive employee engagement survey, completed by over 88% of our employees in all of our offices to measure employee satisfaction, morale and engagement in a variety of areas. Through feedback in this survey, as well as input from our Board of Directors during multiple board meetings, in late 2024 we formalized the following set of five core values that reflect how our colleagues should strive to operate and behave across Greenlight, regardless of location, level, or function: Nimble, Innovative, Excellence, Accountable, and Collaborative. In 2025, we embedded these core values throughout our culture through such actions as incorporating the values into our talent acquisition and employee review processes as well as into our quarterly employee recognition and spotlight program.

Community

We aim to positively influence social, environmental and economic conditions for our employees, and by extension the communities where we live and work.

The Company and our Board value each of our employees and remain committed to ensuring that a safe and healthy workplace and environment is maintained. The Company is helping our employees and their families thrive by offering comprehensive benefit plans and personal and professional wellness tools, including premium healthcare benefits, life and disability insurance, generous vacation allowances irrespective of title and position, a health and wellness stipend, a flexible work policy and company-sponsored access to professional development and training seminars and programs. In addition to fostering an environment of workplace respect, we encourage employees to preserve and promote a clean, safe, and healthy local and global environment. In addition, the Company offers, among other activities, social events organized by the Company’s Social Committee, and a new peer nominated employee recognition program put in place in early 2024.

The Company has had a Charity Committee since 2006, which is composed of employees with oversight from a designated executive officer. The Charity Committee considers donation requests by employees that focus on areas of environment, youth and sports, arts and culture and benevolence. Additionally, at the discretion of the designated executive officer, the Company matches contributions made by our employees to non-profit organizations, including to environmental and social causes. During 2025, the Company supported the Cayman Islands Crisis Center (shelter for women), YMCA, Code Cayman (providing free programming courses to youth), and the Cayman Islands Ministry of Youth, Sports, Culture and Heritage’s “Proud of Them” campaign.

Since 2008, we have maintained a scholarship program that provides financial assistance to Caymanian students who wish to further their post-high school education, allowing them to obtain degrees or vocational training in the field of their choice. We are proud that during 2025, we continued to provide scholarship funds to select Caymanian students to assist with their post-secondary education, and we have provided scholarship funds to over 100 students since inception of the program.

6 2026 PROXY STATEMENT

GREENLIGHT RE

Environmental

Climate change is a clear and present threat to the long-term health of our planet. Accordingly, the Company understands its responsibility not only to provide solutions that help our clients manage their environmental and climate change risks, but also to monitor and control our carbon usage and ecological impact resulting from our operations. Our Company is headquartered in Camana Bay, Grand Cayman, which is a community that values sustainable practices and initiatives, including a solar energy program, a recycling program, a farmers market to encourage locally-sourced food, and electric vehicle charging stations.

Further, while our operations do not have a large physical footprint, we recognize that even the smallest measures contribute to minimizing our environmental impact and maximizing the sustainability of our business. As part of those small efforts, we have reduced our printing (including for instance a paperless claims processing system designed to eliminate the need for printing hard copies of claims files), maintain a recycling program in our Cayman headquarters, leverage cloud application services and third party hosting to reduce data center processing, and promote flex hours and a work-from-home policy to help reduce traffic congestion and commuting emissions.

In addition, by virtue of our business, the Company assesses and offers protection against weather-related risks such as hurricanes, storms, wildfires and floods, helping businesses and individuals proactively manage their exposure to such risks. As insured losses from natural catastrophes continue to increase due to such factors as human population growth, urbanization, economic development and a higher concentration of assets in exposed areas, as well as a trend of increasing large losses from secondary perils (such as hail, flood, storm or bushfire), we continue to offer solutions to our clients and customers to help mitigate the increased costs that climate change is exacerbating. We actively include environmental risks within our modelling and risk management practices, in order to inform our underwriting decisions. Our continuous efforts to update and refine our risk perception in alignment with evolving loss and hazard trends allow us to remain agile and often more responsive than traditional vendor models. Our strategy in this area integrates a broad spectrum of data sources, including modelled cedant data and claims to inform our pricing and underwriting strategies. In assessing climate and environmental-related risks, we also rely on a diverse set of external data, including from the Intergovernmental Panel on Climate Change and National Oceanic and Atmospheric Administration.

The Company also considers environmental causes with regard to its sponsorships and donations. For instance, the Company is a proud supporter and “diamond level” sponsor of the National Trust for the Cayman Islands and in 2025 provided donations to the National Trust in relation to wetlands and mangrove preservation. The National Trust is a nonprofit organization created to preserve the biodiversity of the Cayman Islands, working through education and conservation to protect environmentally sensitive areas across all three Cayman Islands.

2026 PROXY STATEMENT 7

GREENLIGHT RE

VOTING

Voting Procedures

As a shareholder of GLRE, you have a right to vote on certain business matters affecting GLRE. The proposals that will be presented at the Meeting and upon which you are being asked to vote are discussed below under the “Proposals” section. Each ordinary share of GLRE you own as of the record date, May 1, 2026, entitles you to one vote on each proposal presented at the Meeting, subject to certain provisions of our Articles, as described below under “Voting Securities and Vote Required.”

Electronic Availability of Proxy Materials for 2026 Annual Meeting

Under rules adopted by the Securities and Exchange Commission, or the SEC, we are furnishing proxy materials to our shareholders primarily via the Internet, instead of mailing printed copies of those materials to each shareholder. On or about May 13, 2026 we will mail to our shareholders (other than those who previously requested electronic or paper delivery of all proxy materials) a Notice of Internet Availability containing instructions on how to access our proxy materials, including our proxy statement and our annual report. The Notice of Internet Availability also instructs you on how to access your proxy card to vote over the Internet, by mail or telephone.

This process is designed to expedite shareholders’ receipt of proxy materials, help conserve natural resources and lower the cost of the Meeting. However, if you would prefer to receive printed proxy materials, please follow the instructions included in the Notice of Internet Availability. If you have previously elected to receive our proxy materials electronically, you will continue to receive these materials via e-mail unless you elect otherwise.

Requesting a Paper Copy of Proxy Materials

Any registered shareholder receiving a Notice of Internet Availability who would like to request a separate paper copy of these materials, should: (1) go to www.envisionreports.com/GLRE and follow the instructions provided; (2) send an e-mail message to investorvote@computershare.com with “Proxy Materials Greenlight Capital Re, Ltd.” in the subject line and provide your name, address and the control number that appears in the box on the Notice of Internet Availability, and state in the e-mail that you want a paper copy of current meeting materials; or (3) call our stock transfer agent (Toll Free) at 1 (866) 641-4276.

Householding

The SEC has adopted rules that permit companies to satisfy the delivery requirements for notices of annual meetings, proxy statements, proxy cards and annual reports with respect to two or more shareholders sharing the same address by delivering a single set of proxy materials to those shareholders. A single notice will be delivered to multiple shareholders sharing an address unless contrary instructions have been received. Shareholders sharing an address who are currently receiving multiple copies may also request delivery of a single copy by following the instructions above.

8 2026 PROXY STATEMENT

GREENLIGHT RE

VOTING SECURITIES AND VOTE REQUIRED

As of April 10, 2026, 33,510,609 ordinary shares, par value $0.10 per share are issued and outstanding. This is our only class of equity shares outstanding and entitled to vote at the Meeting.

Ordinary Shares

Each ordinary share is entitled to one vote per share. However, except upon unanimous consent of our Board, no holder is permitted to acquire an amount of shares which would cause any person to own (directly, indirectly or constructively under applicable United States tax attribution and constructive ownership rules) 9.9% or more of the total voting power of the total issued and outstanding ordinary shares, such person referred to hereinafter as a 9.9% Shareholder. In May 2023, in connection with the proposals that passed at our 2023 AGM eliminating our former dual-class share structure, our Board consented to our Chairman David Einhorn beneficially owning more than 9.9% of the total voting power of the total issued and outstanding ordinary shares, up to the amount of ordinary shares beneficially owned by David Einhorn at the time of the consent (i.e., 6,254,714 ordinary shares).

Quorum; Vote Required

The attendance of two or more persons representing, in person or by proxy, more than 50% of the issued and outstanding ordinary shares as of May 1, 2026, the record date for the determination of persons entitled to receive notice of, and to vote at, the Meeting, or the Record Date, is necessary to constitute a quorum at the Meeting. Assuming that a quorum is present, the affirmative vote of the holders of a simple majority of the votes cast by the holders of ordinary shares present in person or represented by proxy at a general meeting of the Company and entitled to vote will be required to elect each of the director nominees named in proposal 1 and to approve proposals 2 and 3, each set forth in the Notice of Annual General Meeting of Shareholders. Although the advisory votes in proposal 3 is non-binding as provided by law, our Board of Directors will review the result of the vote and take it into account in making future determinations concerning executive compensation.

With regard to any proposal or director nominee, votes may be cast in favor of or against such proposal or director nominee or a shareholder may abstain from voting on such proposal or director nominee. Abstentions will be excluded entirely from the vote and will have no effect except that abstentions and “broker non-votes” will be counted toward determining the presence of a quorum for the transaction of business. Generally, broker non-votes occur when ordinary shares held by a broker for a beneficial owner are not voted on a particular proposal because the broker has not received voting instructions from the beneficial owner, and the broker does not have discretionary authority to vote on a particular proposal.

SOLICITATION AND REVOCATION

Proxies must be received by us by 11:59 p.m. (local time) on July 27, 2026, the day prior to the Meeting day. A shareholder may revoke his or her proxy at any time up to one hour prior to the commencement of the Meeting.

To do this, you must:

•enter a new vote by telephone, over the Internet or by signing and returning another proxy card at a later date;

•file a written revocation with the Secretary of the Company at our address set forth above;

•file a duly executed proxy bearing a later date; or

•appear in person at the Meeting and vote in person.

The individuals designated as proxies in the proxy card are officers of the Company.

All ordinary shares represented by properly executed proxies that are returned, and not revoked, will be voted in accordance with the instructions, if any, given thereon. If no instructions are provided in an executed proxy, it will be voted FOR the election of each director nominee named in proposal 1, FOR each of proposals 2 and 3, each proposal as described herein as set forth on the accompanying form of proxy, and in accordance with the proxy holder’s best judgment as to any other business as may properly come before the Meeting. If a shareholder appoints a person other than the persons named in the enclosed form of proxy to represent him or her, such person should vote the shares in respect of which he or she is appointed proxy holder in accordance with the directions of the shareholder appointing him or her.

2026 PROXY STATEMENT 9

GREENLIGHT RE

PROPOSAL ONE: ELECTION OF DIRECTORS OF THE COMPANY

The Articles provide that members of our Board shall be appointed annually for a term of appointment that will end at the conclusion of the Annual General Meeting of Shareholders of the Company following the one at which they were appointed. Currently, we have ten directors serving on our Board. At the recommendation of our Nominating, Governance and Corporate Responsibility Committee, our Board has nominated current members of the board David Einhorn, Johnny Ferrari, Ursuline Foley, Leonard Goldberg, Victoria Guest, Ian Isaacs, Bryan Murphy, Joseph Platt, Daniel Roitman and Greg Richardson. At the recommendation of our Nominating, Governance and Corporate Responsibility Committee, our Board has also determined to increase the size of the Board from 10 to 11, and has nominated Ariel Warszawski to serve as a director of the Company. The Company anticipates eventually targeting a board size of between 8 and 10 directors through continued refreshment and/or retirements. All of the nominees will be voted on by all holders of record of ordinary shares as of the Record Date. Our Board has no reason to believe that any nominee will not continue to be a candidate or will not be able to serve as a director of the Company if elected. In the event that any nominee is unable to serve as a director, the proxy holders named in the accompanying proxy have advised that they will vote for the election of such substitute or additional nominee(s) as our Board may propose. Our Board unanimously recommends that you vote FOR the election of each of the nominees.

Director Nominees

Unless otherwise directed, the persons named in the proxy intend to vote all proxies FOR the election of each of the following director nominees.

Name

Age

Position

Since

Independent

Member of Audit Committee

Member of Compensation Committee

Member of Underwriting Committee

Member of Nominating, Governance and Corporate Responsibility Committee

Greg Richardson

Director, Chief Executive Officer

2024

•

David Einhorn

Director (Chair)

2004

•

Johnny Ferrari

Director

2021

•

Ursuline Foley

Director

2021

•

Leonard Goldberg

Director

2005

•

Victoria Guest

Director

2021

•

Ian Isaacs

Director

2008 and 2004-2007

•

Bryan Murphy

Director

2008

•

Joseph Platt

Director (Lead Independent)

2022 and 2004-2021

•

Daniel Roitman

Director

2023

Ariel Warszawski

Director

N/A

•

Chair

•

Member

If elected, the board will determine in the future which of the Company’s standing committees Mr. Warszawski will join.

There is no family relationship among any of the nominees, directors and/or any of the executive officers of the Company and no arrangements or understandings between any of the nominees and any other person pursuant to which he or she was selected as a nominee.

Each of the nominees have consented to serve as a director of the Company if elected.

10 2026 PROXY STATEMENT

GREENLIGHT RE

Director Nominee Skills and Qualifications

Our Board seeks directors with a broad range of skills, experience and perspectives in order to ensure effective oversight of the Company’s strategies and risks. The Board believes its members must be willing and able to devote adequate time and effort to Board responsibilities. In evaluating director candidates, the Nominating, Governance and Corporate Responsibility Committee evaluates attributes such as independence, integrity, expertise, breadth of experience, diversity, knowledge about the Company’s business and industry and ownership in the Company. The skills matrix below highlights our director nominees’ key skills and qualifications that are directly relevant to our business, strategy and operations.

Greg Richardson

David Einhorn

Johnny Ferrari

Ursuline Foley

Leonard Goldberg

Victoria Guest

Ian Isaacs

Bryan Murphy

Joseph Platt

Daniel Roitman

Ariel Warszawski

Financial Services Industry Experience

Senior Leadership Experience

Financial Reporting

Risk Assessment/Risk Management

Legal/Regulatory Expertise

Public Company Board Experience

Global/International experience

Cybersecurity/Technology Experience

2026 PROXY STATEMENT 11

GREENLIGHT RE

Current Board Snapshot

Director Independence

70%

Independent

Committee Leadership Diversity

50%

2 of our 4 committees are chaired by women

Director Diversity

30%

Diverse

Director Age

Average

4 directors: 55 to 60 years old

2 directors: 61 to 65 years old

4 directors: >65 years old

Director Refreshment

Of our current ten directors, three joined in 2021, one joined in 2023 and one joined in 2024. In addition, the Board has nominated one additional independent candidate to join the Board in 2026.

2021

2023

2024

THREE NEW DIRECTORS JOINED

ONE NEW DIRECTOR JOINED

Victoria Guest

Daniel Roitman

Greg Richardson

Johnny Ferrari

Ursuline Foley

12 2026 PROXY STATEMENT

GREENLIGHT RE

Director Nominee Biographical Information

Set forth below is biographical information concerning each nominee for election as a director of the Company, including a discussion of such nominee’s particular experience, qualifications, attributes or skills that lead our Nominating, Governance and Corporate Responsibility Committee and our Board to conclude that the nominee should serve as a director of the Company.

Greg Richardson

Age: 66

Director Since: 2024

Business Experience: Mr. Richardson has been our CEO and a director since January 1, 2024, and a director of Greenlight Re since March 2024 following regulatory approval. He previously served as Chief Risk and Strategy Officer at TransRe from 2014 to 2023. Prior to that, he held strategic planning and underwriting roles and served as Chief Underwriting Officer at Harbour Point Re (which merged with Max Re Capital to form Alterra Re) from 2006 to 2013.

Education: Mr. Richardson graduated with a Bachelor of Science Honors degree in Mathematics from Purdue University, was a Marshall Scholar at Oxford University and obtained his Master of Business Administration degree in Finance from the University of Chicago.

Qualifications: Mr. Richardson’s deep U.S. and international expertise in the industry and experience in a number of underwriting and strategic positions, makes him well suited for the Chief Executive Officer role. Mr. Richardson’s leadership experience also enables him to provide valuable contributions to the Board and help shape our go-forward strategy.

David Einhorn

Age: 57

Director Since: 2004

Business Experience: Mr. Einhorn has been Chair of our Board since our formation in 2004. Mr. Einhorn also has served as a director of Greenlight Re since 2004. Mr. Einhorn co-founded, and has served as the President of, DME Capital Management, LP d/b/a Greenlight Capital (together with its predecessor entity, Greenlight Capital, Inc., referred to herein as Greenlight Capital) since January 1996. Mr. Einhorn serves as President of DME Advisors, LP, or DME Advisors, the investment advisor of Solasglas Investments, LP in which the Company invests. Greenlight Capital and DME Advisors are affiliates of the Company.

Education: Mr. Einhorn graduated summa cum laude with distinction from Cornell University in 1991 where he earned a B.A. from the College of Arts and Sciences.

Directorships: Since April 2006, Mr. Einhorn has served as a director of Green Brick Partners, Inc. (Nasdaq: GRBK).

Qualifications: Mr. Einhorn’s business acumen, public company board experience, extensive investment experience and share ownership provides valuable strategic leadership to the Company.

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GREENLIGHT RE

Johnny Ferrari

Age: 58

Director Since: 2021

Business Experience: Mr. Ferrari has been a director of the Company and Greenlight Re since 2021, and is currently a consultant in the financial services industry after having retired from KPMG International, or KPMG, in June 2021. Prior to his retirement, Mr. Ferrari provided audit services to companies in the banking, insurance and asset management industries. Mr. Ferrari held multiple roles for KPMG, including serving as a member of the Global Monitoring Group for KPMG International from July 2017 to June 2021, Chief Operating Officer for Audit Quality for KPMG EMA Region from October 2019 to June 2021 and as an Audit Partner for KPMG Cayman Islands from October 2003 to September 2019, including serving as Partner in Charge of Risk Management from October 2012 to September 2019. Mr. Ferrari also served as a member of KPMG’s Executive Management Committee and participated on the Audit Quality Professional Practice Steering Committee from October 2012 to September 2019. Mr. Ferrari has experience in the preparation of financial statements in accordance with United States and International generally accepted accounting principles. Mr. Ferrari is also a director of North End Re (Cayman) SPC, a subsidiary of Brookfield Reinsurance Ltd., since July 2022.

Education: Mr. Ferrari holds a Bachelor’s degree from the University of Toronto. Mr. Ferrari is a member of the Chartered Professional Accountants of Ontario and Cayman Islands Institute of Professional Accountants.

Qualifications: Mr. Ferrari’s international audit, accounting, regulatory and operational experience, as well as his deep familiarity with the financial services industry, adds financial expertise, compliance risk oversight and leadership to the Board.

Ursuline Foley

Age: 65

Director Since: 2021

Business Experience: Ms. Foley has been a director of the Company and Greenlight Re since 2021. From April 2016 until her retirement in October 2018, Ms. Foley served as Chief Corporate Operations Officer and Managing Director of XL Group PLC, a global provider of commercial insurance and reinsurance, which became AXA XL in September 2018. From 2010 to April 2016, Ms. Foley served as Chief Information Officer, Chief Data Officer (Enterprise Enablement Strategy) for XL Group PLC. Ms. Foley has also served in other senior roles for XL Group PLC, including Senior Vice President, Chief Information Officer of Reinsurance for the Property and Casualty, Life and Financial Lines for XL Reinsurance.

Education: Ms. Foley graduated from University College Cork, where she earned a Bachelor’s degree in 1982 and a Teaching Diploma in 1983, and from Pace University, where she earned a Masters of Computer Science in 1991. Ms. Foley also holds certificates from Babson University in Technology Leadership, the NYC College of Finance and NYC College of Insurance.

Directorships: Ms. Foley currently serves on the board of directors of Provident Financial Services, Inc. (NYSE: PFS) and Provident Bank and is a member of the Risk, Finance and Technology committees. Ms. Foley also currently serves on several advisory and non-profit boards.

Qualifications: Ms. Foley possesses substantial executive leadership skills and valuable operational, cyber, risk and technology insights into global business strategy. Her other significant public and private company board experience enhances our governance structure and broadens the Board’s perspectives. Ms. Foley is a Qualified Risk Director (QRD) certified by the Directors Chief Risk Officer (DCRO) Institute since 2021, and also holds a Certified Cyber Risk for Boards Certification from the DCRO Institute since 2022.

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Leonard Goldberg

Age: 63

Director Since: 2005

Business Experience: Mr. Goldberg has been a director of the Company and Greenlight Re since 2005. He currently serves as President of Len Goldberg Inc., a consulting firm providing services to the insurance industry, and as an executive advisor to a private equity firm investing in the insurance industry. He served as our interim Chief Executive Officer from March 31, 2017 through June 30, 2017 and as our as Chief Executive Officer of our Company from August 2005 through August 2011. Mr. Goldberg has more than 30 years of insurance and reinsurance experience. He worked with the Alea Group, a reinsurance company, from August 2000 to August 2004, including serving as Chief Executive Officer of Alea North America Insurance Company and Alea North America Specialty Insurance Company from March 2002 to August 2004, where he was responsible for the insurance and reinsurance strategy for the North America region. Prior to working with the Alea Group, Mr. Goldberg served as Chief Actuary and Senior Vice President – Financial Products of Custom Risk Solutions, a managing general agency company, from April 1999 to August 2000. From May 1995 to December 1998, Mr. Goldberg provided various actuarial services to Zurich Group, a reinsurance company, including acting as chief actuary of Zurich Re London.

SEC Form DEF 14A filed by Greenlight Capital Re Ltd.