Deed of Settlement and Release, effective as of September 4, 2020, by and among Brendan Barry, Greenlight Capital Re, Ltd. and Greenlight Reinsurance, Ltd

This Deed of Settlement and Release is made the 4^th day of September 2020

(1)BRENDAN BARRY of 27 Crystal Drive, Crystal Harbour, Seven Mile Beach (the "Employee");

(2)GREENLIGHT REINSURANCE, LTD of 65 Market Street, Suite 1207, Jasmine Court, Camana Bay, Grand Cayman, KY1-1205, Cayman Islands;

(3)GREENLIGHT CAPITAL RE, LTD of 65 Market Street, Suite 1207, Jasmine Court, Camana Bay, Grand Cayman, KY1-1205, Cayman Islands (together with Greenlight Reinsurance Ltd, the "Employers")

(Each a "Party" and together "the Parties") 

(A)The Employee was employed as Chief Underwriting Officer (the "Employment") pursuant to a contract of employment dated August 15, 2006 (the “Contract”), as subsequently amended by written notification on February 27, 2009, March 11, 2011, August 15, 2011, and October 27, 2014, and as further amended as of March 15, 2018;

(B)The Parties have agreed to terminate the Employment by mutual consent effective 4 September 2020 (the "Termination Date");

(C)The Parties now wish to settle all matters between them and have agreed to a full and final settlement on the terms and conditions contained in this Deed and have agreed to enter into this Deed in consideration of the mutual covenants and other valuable consideration set out below

1.1In this Deed, unless otherwise indicated, the following expressions shall bear the following meanings:

(a)"Associated Entities" means the Employers and each and all of their respective current, previous, and future parent companies, direct or indirect subsidiaries, and affiliates;

(b)"Claims" means all causes of action, matters, and disputes arising from or related to the Employment or the termination thereof, or otherwise arising between the Parties, whether known or unknown, that exist (or may exist) as at the date of execution of this Deed including but not limited to:

(i)Any and all actions, causes of action, claims, covenants, contracts and/or controversies in any jurisdiction of whatsoever character howsoever arising whether in law, equity or otherwise;

(ii)Unfair dismissal pursuant to part VII of the Labour Law (2011 Revision) (the "Labour Law") or any successor legislation;

(iii)Severance pay pursuant to part V of the Labour Law or any successor legislation;

(iv)Wrongful or constructive dismissal in respect of the Employment howsoever arising;

(v)Contractual entitlement in respect of salary, commission, holiday pay (except as provided in Section 3.2, below), overtime, notice, severance, other benefits or otherwise arising out of or in connection with the Contract (as amended) or Employment, including for the avoidance of doubt any discretionary bonus; and

(vi)Discrimination howsoever arising or of any nature.

(c)References to recitals and clauses are references to the recitals to and clauses of this Deed;

(d)Headings to clauses and the use of bold type are for convenience only and shall not affect the interpretation or construction of this Deed; and

(e)Words in the singular include the plural and vice versa.

1.2Should any provision of this Deed require interpretation it is agreed by the Parties that such interpretation shall not be subject to a presumption that the Deed is to be construed more strictly against the party who prepared the Deed.

2.1.The Parties hereby agree that the Employment shall terminate by mutual consent and without further notice as of the Termination Date, at which time the Employee shall cease to be employed by the Employers.

2.2.The Employee agrees and undertakes to resign as of the Termination Date from all officer, board, committee, and other appointments or positions held in respect of the Employers and their Associated Entities. In the event that the Employee fails to resign in accordance with this clause he hereby irrevocably grants a power of attorney to the Employers empowering them to execute the necessary instruments of resignation on his behalf.

2.3.The Employee agrees that other than as set forth in Section 3, below, Employee hereby:

(a)Releases each and all of the Employers and their Associated Entities (collectively, the “Companies”), and each and all of the Companies’ respective servants, agents, directors, officers, employees, partners, equityholders, investors, and representatives (collectively, with the Companies, the “Releasees”) from all and any Claims howsoever arising, whether under Cayman Islands, United States, New York, or other law, whether under any statute, regulation, ordinance, constitution, treaty, contract, common law, or otherwise, and whether such Claims are accrued or contingent;

(b)Undertakes and covenants not to assert any Claims or commence legal proceedings in respect of such claims against any of the Releasees at any time in any forum or any jurisdiction (including without limitation the Director of Labour, the Department of Employment Relations or a Labour Tribunal in the Cayman Islands or the Grand Court of the Cayman Islands); and

(c)Undertakes and covenants to comply with the terms of Section 9 of the Contract (as modified below), which he agrees survives his termination, and acknowledges that such terms are enforceable in their entirety (as modified);

(d)Undertakes and covenants that before and after the Termination Date, he will reasonably cooperate with the Employers and their Associated Entities, in connection with (i) the smooth transition of his role and responsibilities, as directed by the Employers, including by promptly responding to requests for information, (ii) any actual or threatened investigation, administrative proceeding, or litigation relating to any matter that occurred during the Employment in which he was involved or of which he has knowledge, and (iii) any other internal or external review of the Companies, including by any regulator or agency, or any actual or threatened arbitration; provided that the Companies will attempt to schedule Employee’s cooperation for mutually agreeable times and locations in a manner that does not unduly interfere with Employee’s personal or professional pursuits and will reimburse Employee for any reasonable pre-approved out-of-pocket expenses Employee incurs in connection with such cooperation. Employee will render his cooperation under this paragraph without requiring a subpoena, and will do so honestly, truthfully, forthrightly, and completely, including supplying relevant documents and information in his possession, custody, or control;

(e)By September 4, 2020, Employee agrees to provide the documents and information set forth in Paragraph 9 of the affidavit provided to Employee on this date (the “Affidavit”).

(f)Agrees and confirms that the none of the Releasees owes him any wages, bonuses, pro-rated bonuses (for 2020 or any other year), equity compensation, stock options, restricted shares, sick pay, vacation pay (except as provided in

Section 3.2, below), severance pay, notice pay, pension contribution, equity award (including but not limited to any Option (as defined in the Contract, as amended)), or any other compensation, payment, amount, benefit, or interest whatsoever; and

(g)Confirms and acknowledges that he has not suffered any known workplace injury or occupational disease and that he has not been victimised in consequence of reporting any wrongdoing relating in any way to the Employment.

2.4.Without prejudice to the generality of clause 2.3 above, the Employee expressly agrees and acknowledges that:

(a)Other than basic salary accrued to the Termination Date, he shall not be entitled to receive any further sum whether by way of notice pay, severance pay, or otherwise, including but not limited to under Section 8 of the Contract;

(b)He shall not be entitled to receive any Retention Bonus pursuant to the Retention Bonus Agreement between the Employee and Greenlight Reinsurance Ltd dated 4 May 2020;

(c)All of his unvested Awards under the Greenlight Capital Re Ltd. Amended and Restated 2004 Stock Incentive Plan, as amended (the “LTIP”), are hereby cancelled, and all of Employee’s rights to restricted shares are hereby terminated; and

(d)He shall repay to the Employers within 7 days of the Termination Date the pro-rated portion of his annual Permanent Residency fee attributable to the period after the Termination Date.

2.5.In the event that the Employee breaches any material provision of this Deed or pursues or encourages any Claim against any of the Releasees, he agrees to indemnify without limitation such parties for any losses suffered as a result thereof, including but not limited to advancing all of their legal and professional fees with respect to such matter(s). For avoidance of doubt, Employee’s indemnification obligations under this Section 2.5 shall not be triggered in the event of litigation brought against the Company by an employee other than Employee, so long as Employee is not a party to such litigation and does not

encourage or assist such other employee or the employee’s counsel in connection with such litigation (other than via a subpoena or by providing truthful sworn testimony in accordance with applicable law).

2.6.In signing this Deed the Employee acknowledges that he has read and understood this Deed and has obtained or had the opportunity to obtain independent legal advice in relation thereto. The Employee further acknowledges that he signs this Deed voluntarily and understands that the Deed contains a full and final release of all claims that he has or may have against any of the Releasees.

2.7.The Employee shall not commence or maintain, or procure, assist, encourage, support or otherwise participate in the commencement or continuance of, any proceedings in respect of the Claims, except, for the avoidance of doubt, for the purpose of enforcing this Deed.

3.1Conditional upon the Employee executing this Deed on the date hereof and complying with all of the terms hereof and with the Surviving Provisions (as defined below), the Employers:

(a)Agree that health insurance for the Employee and his dependants shall be maintained for a period of 3 months after the Termination Date or until the Employee secures alternative employment, whichever is the sooner, subject to the Employee paying the premium in respect of the said insurance coverage.

(b)Irrevocably and unconditionally release and discharge Employee with respect to any and all Claims howsoever arising, whether under Cayman Islands, United States, New York, or other law, whether under any statute, regulation, ordinance, constitution, treaty, contract, common law, or otherwise, and whether such Claims are accrued or contingent; provided that, for avoidance of doubt, nothing herein releases or discharges any claims (i) based on Employee’s wilful misconduct or gross negligence in the performance of his duties for the Companies, or the misuse of the Companies’ Confidential Information (as defined in the Contract), (ii) that arise under this Deed or under any of the Surviving Provisions, or the breach of Sections 2, 3, 9, 10, or 11 hereof, (iii) that arise after

the Termination Date, or (iv) for the repayment of Permanent Residency Fees advanced by the Employers on Employee’s behalf for the period from September 30, 2020 through August 31, 2021, in the total amount of CI$16,250 (which Employee shall repay to the Employers within ten (10) days hereof).

(c)Will issue an instruction to their current directors and senior officers not to make or publish any disparaging, derogatory, or defamatory comments or statements about Employee in any forum, whether oral or written.

3.2The Employers shall pay the Employee for any accrued but unused vacation (if any), in accordance with the Employers’ vacation policy, to be paid within ten (10) days hereof.

3.3The Employers shall reimburse the Employee for any as-yet unreimbursed business expenses that were properly accrued prior to the Termination Date, in accordance with the terms and conditions of the Employers’ expense reimbursement policy.

3.4The Employee will remain eligible to receive payments in connection with any quantitative bonuses previously awarded to the Employee in accordance with Greenlight Capital Re, Ltd.’s Compensation Plan, subject to the terms and conditions of that Plan (provided that, for avoidance of doubt, the Employee is not entitled to any such bonus with respect to 2020 or any later year, and is not entitled to any other bonuses or benefits under that Plan, including any discretionary bonuses or pro rata bonuses, and also is not eligible for any payments, rights, or benefits under any other plan, award, or agreement, including but not limited to the LTIP).

3.5Nothing in this Deed shall be construed to waive or release any right to indemnification Employee otherwise would have under any applicable by-law, duly-executed agreement, or insurance policy with respect to claims threatened or brought against Employee by any third parties.

4.1Entry into this Deed and performance of the obligations hereunder shall not constitute an admission of liability howsoever arising by any Party.

5.1This Deed may be pleaded and tendered by any Party as an absolute bar and defence to any proceeding brought in breach of the terms of this Deed.

6.1.The Parties shall (at their own cost) do and execute or procure to be done and executed all necessary acts, agreements, instruments, deeds, documents and things reasonably within their power to give effect to and carry out this Deed and its intents and purposes, and the Parties shall co-operate to the fullest extent practicable to that end.

7.1Each Party hereby separately represents and warrants to the other Party that:-

(a)it has taken all necessary actions to authorize and approve its entry into this Deed and the execution of the same;

(b)all necessary authorizations and approvals for the performance of its obligations hereunder have been obtained and remain in force;

(c)its entry and the performance of its obligations under this Deed will not violate any provision of its constitutive documents or any provision of any law applicable to it, nor conflict with or breach or require any consent under any agreement or instrument to which it is party or by which it is or any of its assets or properties is bound; and

(d)this Deed has been duly executed by it and constitutes a valid and legally binding obligation which is enforceable against it in accordance with its terms.

8.1 Each Party hereby separately represents and warrants to the other Party that:-

(a)it is the sole and lawful owner of all right, title, and interest in and to each and every Claim which such Party settles herein and in respect of which a waiver, release and discharge is given under this Deed; and

(b)it has not assigned, transferred or conveyed, or purported to assign, transfer or convey, any Claim or any rights in respect of a Claim to any person who is not a party to this Deed.

9.1 It is understood by the Parties that this Deed will be publicly filed by Greenlight Capital Re Ltd in a Form 8-K with the United States Securities and Exchange Commission. Employee agrees to treat this Deed, and the terms and conditions hereof, as strictly confidential prior to such securities filing, and Employee will not discuss this Deed, or the negotiations, correspondence, or discussions which led to this Deed, with the media, any of the Companies’ clients or employees, or any business counterparties, either before or after this Deed is publicly filed.

10.1 Section 9 of the Contract is explicitly incorporated into this Deed by reference, including but not limited to the provision regarding Acknowledgments (Sections 9(a) and 9(j)), the Confidentiality provision (Section 9(b)), the Non-Compete provision (Section 9(c), as modified below), the provision regarding Non-Solicitation of Employees (Section 9(d)(provided that subject to Employee’s execution and compliance with this Deed, the Employers will not seek to prevent Employee from soliciting or working with Tim Courtis, the provision regarding Non-Solicitation of Customers (Section 9(e)), the provision regarding Post-Employment Property (Section 9(f)), the Non-Disparagement provision (Section 9(g)), the Enforcement provision (Section 9(h)), and the Blue-Pencil provision (Section 9(i))(collectively, the “Surviving Provisions”). The Employee hereby acknowledges and agrees that the foregoing provisions are enforceable in full and waives any objections thereto.

10.2 Notwithstanding the foregoing, it shall not be deemed a breach of Section 9(c) of the Contract, or of this Deed, for Employee to form, become employed by, render services for, or own an interest in any of the entities listed in Paragraph 9 of the Affidavit (the “Designated Entities”), provided that Employee does not otherwise violate any of the Surviving Provisions or the provisions of this Deed.

11.1The Parties agree that any work of authorship, invention, design, discovery, development, technique, improvement, source code, hardware, device, data, apparatus, practice, process, method or other work product whatsoever (whether or not patentable or subject to copyright) related to the business of the Employers (“Employer related works”) that the Employee either solely or in collaboration with others has made or may make, discover, invent, develop, perfect or reduce to practice during the course of the Employment whether or not during business hours and created, conceived or prepared on the Employers' premises or otherwise shall be the sole property of the Employers. For the avoidance of doubt, Employer Related Works shall not include any materials owned by the Designated Entities (so long as such materials do not contain any of the Companies’ trade secrets or Confidential Information (as defined in the Contract)).

11.2Without prejudice to the generality of the foregoing, the Employee agrees that all of the foregoing and any (i) inventions (whether patentable or not and without regard to whether any patent therefor is ever sought), (ii) marks, names or logos (whether or not registrable as trade or service marks and without regard to whether registration therefor is ever sought), (iii) works of authorship (without regard to whether any claim of copyright therein is ever registered) and (iv) trade secrets, ideas and concepts (collectively "Intellectual Property Products") created, conceived or prepared on the Employers' premises or otherwise, whether or not during normal business hours, shall perpetually and throughout the world be the exclusive property of the Employers as shall all tangible media (including but not limited to papers, electronic media of all types, and models) in which such Intellectual Property Products are recorded or otherwise fixed. For the avoidance of doubt, Intellectual Property Products shall not include any materials owned by Designated Entities (so long as such materials do not contain any of the Companies’ trade secrets or Confidential Information (as defined in the Contract)).

11.3The Employee further agrees to promptly (and in no event later than the Termination Date) disclose in writing and deliver to the Employers all Intellectual Property Products created during the Employment. The Employee agrees that all works of authorship created by him during the Employment shall be works made for hire of which the Employers are the authors and owners of copyright.

11.4To the extent that any competent authority may determine that any work or authorship created by the Employee during the Employment is not a work made for hire, the Employee hereby assigns all right, title and interest in the copyright therein, in perpetuity and throughout the world, to the Employers. To the extent this Deed does not otherwise serve to grant or otherwise vest in the Employers all rights in any Intellectual Property Product created by the Employee during the Employment, the Employee hereby assigns all right, title and interest therein, in perpetuity and throughout the world, to the Employer.

11.5The Employee agrees to execute immediately upon the Employers' reasonable request and without charge any further assignments, applications, conveyances or other instruments, at any time after execution of this Deed in order to permit the Employers or their respective assigns to protect, perfect, register, record, maintain or enhance their rights in any Intellectual Property Product, provided that the Employers shall bear the cost of any such assignments, applications or consequences.

11.6The Employee agrees and undertakes to

(a) immediately deliver to the custody of the Employers all originals and copies of any documents and other property of the Employers which are in the Employee's possession, under his control or to which he may have access;

(b)immediately delete permanently and irretrievably any electronic material (howsoever stored) within the Employee's possession, control or to which he may have access belonging to the Employers or relating in any way to the Employers’ business;

(c)duly execute the Affidavit, which shall be part of this Deed, and provide it to Employers, with inaccuracy or breach thereof being deemed a material breach of this Deed; and

(d)comply with Section 2.3(e), above.

12.1This Deed, together with Section 9 of the Contract (as modified herein) and the Affidavit, forms the entire agreement and understanding between the Parties relating to the

subject matter of this Deed and supersedes and extinguishes any previous agreement or understanding between the Parties in relation to all or any such matters.

12.2Each Party acknowledges that in entering into this Deed (and any documents referred to in it) it does not rely on, and shall have no remedy in respect of, any representation, warranty or undertaking in writing or otherwise made or given by any person whatsoever which is not expressly set out in this Deed.

13.1 No provision of this Deed shall be deemed varied, waived, amended or modified by either Party, unless such variation, waiver, amendment or modification is made in writing and signed by each Party.

14.1This Deed may be executed in any number of counterparts, each of which shall be an original, and any one of which shall be deemed to be validly executed if evidenced by a facsimile or electronic copy of the executing Party’s signature which shall operate with the same effect as if the signatures thereto were on the same instrument. For the avoidance of doubt, each Party shall be required to sign only one copy of this Deed.

14.2This Deed will become effective upon its execution by all of the Parties hereto; provided that in the event Employee fails to provide the Employers with all of the documents listed in Paragraph 9(a) of the Affidavit on or before 4 September 2020, then the Employers shall be entitled to rescind their execution of this Deed, by written notice to Employee, thus rendering the Deed and Employee’s resignation null and void ab initio, and of no force or effect. Should Employer not rescind this Deed by 5 September, 2020, this Deed shall become final, effective, and irrevocable as of 11:59 PM on that date.

15.1 This Deed shall inure to the benefit of and be binding upon the successors of each Party to this Deed.

15.2 This Deed is personal to the Parties and shall not be capable of assignment save as provided by clause 16.1 above.

16.1 If any of the provisions of this Deed is found by a court of competent jurisdiction to be void or unenforceable, it shall be deemed to be deleted from this Deed and the remaining provisions shall continue to apply, unless the severed portion is essential to the intended purpose of this Deed, in which case the party who was to receive the benefit of the severed portion has the option to void the Deed insofar as it relates to them.

17.1 This Deed shall be governed by and construed in accordance with the laws of the Cayman Islands.

17.2 The Parties hereby agree that the Grand Court of the Cayman Islands shall have exclusive jurisdiction to hear and determine any claim, suit, action or proceeding whatsoever and to settle any dispute which may arise out of any provision of this Deed or out of any action taken or omitted to be taken under this Deed or in connection with the administration of this Deed. The Parties to this Deed irrevocably submit to the exclusive jurisdiction of the Cayman Islands Court.

IN WITNESS WHEREOF the Parties hereto have executed this Deed on the date and year first above written.

/s/ Derek Stenson