SUBSCRIPTION AGREEMENT

Exhibit 99.14

EXECUTION VERSION

SUBSCRIPTION AGREEMENT

This SUBSCRIPTION AGREEMENT (this “Agreement”), dated as of July 23, 2018, is made and entered into by and among Evergreen Parent, L.P., a Delaware limited partnership (“Parent” or the “Partnership”), Enstar Group Limited, an exempted company formed under the laws of Bermuda (“Investor”), K-Z Evergreen, LLC, a Delaware limited liability company (solely for purposes of Sections 2.1(f), 2.2, 7 and 9) (“KZ”) and Trident Pine Acquisition LP, a Delaware limited partnership (solely for purposes of Sections 2.1(f), 2.2, 7 and 9) (“Trident”, together with KZ, the “Initial Investors” and, the Initial Investors together with Parent and Investor, the “Parties”).

WHEREAS, Parent, Evergreen Merger Sub, Inc., a Delaware corporation (“Merger Sub”), and AmTrust Financial Services, Inc., a Delaware corporation (the “Company”), entered into the Agreement and Plan of Merger, dated as of March 1, 2018 (as amended by that certain Amendment No 1., dated as of June 6, 2018 and as further amended from time to time in accordance with the terms thereof, the “Merger Agreement”), pursuant to which, among other things, Merger Sub will be merged with and into the Company, with the Company surviving the merger as the surviving corporation and as a wholly-owned subsidiary of Parent (the “Merger”);

WHEREAS, Trident, K-Z, Parent, Merger Sub and the other individual parties thereto, entered into the Interim Investors Agreement, dated as of March 1, 2018 (as amended by that certain Amendment No 1., dated as of June 6, 2018 and as further amended from time to time in accordance with the terms thereof, the “Interim Investors Agreement”), pursuant to which the parties thereto have agreed to govern their relationship between the date of the Merger Agreement and the Closing; and

WHEREAS, Parent wishes to issue and sell, and Investor wishes to purchase, subject to the substantially contemporaneous consummation of the Merger and the other transactions contemplated by the Merger Agreement and the other conditions set forth herein, an aggregate of $200 million of limited partnership interests of Parent (the “LP Interests”), consisting of Class A Units (as defined in the Interim Investors Agreement), Class B Units (as defined in the Interim Investors Agreement) and Class C Units (as defined in the Interim Investors Agreement), upon the terms and conditions set forth herein.

NOW, THEREFORE, in consideration of the premises and covenants contained herein, the Parties agree as follows:

1. Definitions. Capitalized terms used but not herein defined shall have the respective meanings ascribed to them in the Merger Agreement.

2. Purchase and Sale of Partnership Interests.

2.1 Parent agrees to issue and sell to Investor, and Investor agrees to purchase from Parent, immediately prior to the Closing but conditioned thereon, the LP Interests, for an aggregate purchase price of $200 million in cash, which amount shall be payable immediately prior to the Closing but

conditioned thereon by wire transfer of immediately available funds to an account designated in writing by Parent not less than three (3) Business Days prior to the Closing, subject to the substantially contemporaneous consummation of the transactions contemplated by the Merger Agreement, the Equity Documents and the following conditions as of the closing of the transactions contemplated hereby (the “Investment Closing”):

(a) The LP Interests shall consist of Class A Units, Class B Units and Class C Units. The number of limited partnership interests of each class (i.e. Class A Units, Class B Units and Class C Units) shall be issued to Investor in the same proportion (as between the different classes of limited partnership interests in Parent), and the purchase price per LP Interest shall be the same, in each case, as the limited partnership interests of Parent purchased by Trident and any Affiliate thereof in connection with the Closing;

(b) Each of the conditions to the Closing set forth in Article VI of the Merger Agreement shall have been satisfied or waived (other than conditions that by their nature are to be satisfied at the Closing, provided that such conditions are satisfied or waived at the Closing);

(c) Parent shall have given Investor at least three (3) Business Days’ prior written notice of the proposed date of the Closing;

(d) At the Closing, the Initial Investors shall have contributed or caused to be contributed a cash equity investment to Parent immediately prior to the consummation of the Merger under the Merger Agreement in the amount set forth in their respective Commitment Letters (as reduced by the amount of the Investor’s investment hereunder and other co-investments by other Persons);

(e) Evergreen Parent GP, LLC, the general partner of Parent (the “General Partner”), shall have amended and restated its limited liability company agreement (the “LLC Agreement”) to reflect the applicable terms set forth in to the Interim Investors Agreement;

(f) The limited partnership agreement of Parent (the “LP Agreement” and together with the LLC Agreement, the “Equity Documents”) shall have been amended and restated to reflect the applicable terms set forth in the Interim Investors Agreement and shall be in a form reasonably acceptable to Investor; provided, that: (i) any term set forth in the Interim Investors Agreement that is reproduced in the Equity Documents shall be deemed to be reasonably acceptable to Investor; and (ii) any term not set forth in the Interim Investors Agreement but included in the Equity Documents, which term is not disproportionately adverse to Investor relative to the other

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holders of LP Interests, shall be deemed to be reasonably acceptable to Investor; provided, further, that Parent, the General Partner and the Initial Investors shall negotiate the Equity Documents in good faith and reasonably consider any comments to the Equity Documents suggested by Investor.

(g) The Equity Documents shall be in full force and effect as of the Closing and shall not have been amended or modified other than as contemplated hereby;

(h) None of the Parties hereto (other than the Investor) shall have breached any of its representations, warranties, covenants or agreements set forth herein in any material respect; and

(i) No court or other Governmental Entity of competent jurisdiction shall have enacted, issued, promulgated, enforced or entered any Law (whether temporary, preliminary or permanent) that is in effect and restrains, enjoins or otherwise prohibits consummation of the Investment Closing.

2.2 This Agreement and the transactions contemplated hereby shall constitute a Permitted Equity Syndication (as such term is defined in the Interim Investors Agreement). This Agreement shall constitute a Commitment Letter (as defined in the Interim Investors Agreement). Investor’s Commitment (as defined in the Interim Investors Agreement) may not be increased without the prior written consent of Investor.

2.3 Investor agrees to execute and deliver counterparts to the Equity Documents at the Investment Closing and thereby to be bound by the Equity Documents subject to the terms and conditions thereof.

2.4 Parent agrees to cause Investor to be admitted as a limited partner of Parent at the Investment Closing.

2.5 The purchase and sale of the LP Interests contemplated by this Section 2 shall be evidenced by appropriate instruments or acknowledgements of transfer and recorded in the books and records of Parent. Investor will be issued certificates representing the LP Interests which shall be endorsed with the following legend:

THE LIMITED PARTNERSHIP INTERESTS REPRESENTED BY THIS CERTIFICATE HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”), OR STATE SECURITIES LAWS AND CANNOT BE OFFERED, SOLD, OR TRANSFERRED IN THE ABSENCE OF REGISTRATION OR EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT AND APPLICABLE STATE SECURITIES LAWS AND REGULATIONS PROMULGATED THEREUNDER. THE

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LIMITED PARTNERSHIP INTERESTS REPRESENTED BY THIS CERTIFICATE HAVE BEEN ACQUIRED BY THE REGISTERED OWNER HEREOF FOR INVESTMENT AND NOT WITH A VIEW TO OR FOR SALE IN CONNECTION WITH ANY DISTRIBUTION THEREOF IN VIOLATION OF THE SECURITIES ACT. THE LIMITED PARTNERSHIP INTERESTS MAY NOT BE SOLD, PLEDGED, TRANSFERRED OR ASSIGNED EXCEPT IN A TRANSACTION WHICH IS EXEMPT FROM REGISTRATION UNDER THE PROVISIONS OF THE SECURITIES ACT OR ANY APPLICABLE STATE SECURITIES LAWS, OR PURSUANT TO AN EFFECTIVE REGISTRATION STATEMENT OR IN A TRANSACTION OTHERWISE IN COMPLIANCE WITH APPLICABLE FEDERAL AND STATE SECURITIES LAWS. THE LIMITED PARTNERSHIP INTERESTS REPRESENTED BY THIS CERTIFICATE MAY BE TRANSFERRED ONLY IN ACCORDANCE WITH THE TERMS OF A LIMITED PARTNERSHIP AGREEMENT BETWEEN THE LIMITED PARTNERSHIP AND THE HOLDER.

3. Further Actions; Cooperation. Each Party hereby agrees to execute and deliver such further instruments and take such other action as may be necessary to make effective the transactions contemplated by this Agreement, provided that nothing herein shall obligate Parent to consummate the transactions contemplated by the Merger Agreement or to take any other action with respect to the Merger in circumstances where Parent is not obligated to take such action under the terms and conditions of the Merger Agreement. Investor agrees that it shall, and shall cause its Affiliates to, use its reasonable best efforts to provide information, take reasonable actions similar to those taken by Trident and otherwise cooperate with Parent, in each case solely to the extent reasonably requested by Parent (including by filing disclaimers of control and executing other documents and instruments required by Governmental Entities), with respect to the obtaining of all consents, approvals, authorizations or waivers of Governmental Entities necessary, proper or advisable to consummate the transactions contemplated by this Agreement and the Merger Agreement. Investor agrees to use reasonable best efforts to promptly provide to Parent any information about Investor or its Affiliates that Parent or the Company reasonably determines upon the advice of counsel is required to be included in the Proxy Statement, Schedule 13E-3 or any other filing or notification with any Governmental Authorities in connection with the transactions contemplated by this Agreement and the Merger Agreement.

4. Confidentiality; Public Statements.

4.1 Investor acknowledges that it has had or may have access to certain information provided by or on behalf of Parent concerning or relating to the Merger and the other transactions contemplated hereby or by the Merger Agreement which is either confidential or proprietary in nature (collectively, the “Confidential Information”). Investor agrees that it shall, and shall direct its directors, officers, employees, Affiliates and

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representatives to, maintain the confidentiality of the Confidential Information and refrain from disclosing any Confidential Information to any third person or entity, except (A) as required by law, regulation or legal or regulatory process, (B) to its directors, officers, employees, Affiliates, representatives and third-party advisors who need to know such Confidential Information in connection with advising such Party with respect to the Merger and the other transactions contemplated by this Agreement and by the Merger Agreement, (C) as disclosed in the ordinary course to partners in funds affiliated with Investor and its Affiliates and related co-investors (provided, that such partners and co-investors shall be subject to this Section 4.1 to the same extent as Investor and Investor shall be responsible for any breaches of this Section 4.1 by such partners and co-investors), (D) as authorized by writing by the Parent, or (E) as required in any proceeding arising from a dispute between the Parties alleging a breach of the terms of this Agreement. In the event that Investor receives a request to disclose all or any part of the Confidential Information from a court or governmental or regulatory authority or agency or is obligated to disclose any portion of the Confidential Information as described in clause (A) of the preceding sentence, it shall, to the extent practicable and permitted by law, (x) notify as promptly as possible Parent of the existence, terms and circumstances surrounding such obligation, (y) consult with Parent on the advisability of taking legally available steps to resist or defend against such obligation or to protect the confidentiality of such Confidential Information following such disclosure (which such actions would be at the expense of Parent), and (z) if disclosure of such Confidential Information shall be required, furnish only that portion of the Confidential Information that such Party is requested or legally compelled to disclose. For purposes of this Agreement, “Confidential Information” shall not include information that is or becomes available to the public generally (including if disclosed by the Company), other than as a result of disclosure by Investor or its directors, officers, employees, Affiliates or representatives in breach of the terms of this Agreement.

4.2 Except as expressly contemplated by this Agreement, Investor shall not issue any press release or otherwise make any public statement with respect to the Merger or the other transactions contemplated by this Agreement or by the Merger Agreement without the prior consent of Parent, unless such press release or public statement is required by law, regulation, or legal or regulatory process. In the event that Investor becomes obligated to issue a press release or otherwise make a public statement as described in the preceding sentence, it shall, to the extent permitted by law, (A) notify Parent in writing as promptly as possible of the existence, terms and circumstances surrounding such obligation and (B) consult with Parent on the content of such press release or other public statement.

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5. Representations and Warranties of Investor. Investor hereby represents and warrants to Parent, as of the date hereof and as of the Investment Closing, as follows:

5.1 Investor is a corporation duly organized, validly existing and in good standing under the laws of Bermuda;

5.2 Investor has all requisite power and authority and has received all consents and approvals and taken all action necessary in order to execute and deliver, and perform its obligations under, this Agreement, and to consummate the transactions contemplated by this Agreement;

5.3 This Agreement has been duly and validly executed by Investor, and assuming the due authorization, execution and delivery of this Agreement by the other Parties, constitutes the valid and binding obligation of Investor, enforceable against it in accordance with its terms, except as may be subject to any bankruptcy, insolvency, reorganization, moratorium, fraudulent transfer or other laws, now or hereafter in effect, relating to or limiting creditors’ rights generally, or by general equitable principles;

5.4 To the knowledge of Investor, no consent, approval, qualification, order or authorization of, or filing with, any Governmental Entity is required or triggered with respect to Investor as a result of the valid execution, delivery or performance of this Agreement by Investor;

5.5 The execution, delivery and performance by Investor of this Agreement does not and will not (i) violate the organizational documents of Investor, (ii) subject to the receipt of consents and approvals of Governmental Entities related to the transactions contemplated by the Merger Agreement and the Equity Documents, violate any applicable law or order to which Investor or any of its assets are subject, or (iii) require any consent of any Person under, constitute a default (or an event that with notice or lapse of time or both would become a default) under, result in any breach of or give rise to any right of termination, cancellation, amendment or acceleration of, any right or obligation under any Contract of Investor;

5.6 Investor has the financial capacity to pay and perform its obligations under this Agreement (subject to the terms and conditions hereof) and all funds necessary for Investor to fulfill its obligations under this Agreement shall be available to Investor between the date of this Agreement and the Investment Closing;

5.7 Investor (a) understands and has taken cognizance of all the risk factors related to the investment in Parent, (b) has been granted the opportunity to ask questions and receive answers concerning the terms and conditions of the investment in Parent and to obtain any additional information which Parent possesses or can acquire without unreasonable effort or expense that is necessary to verify the accuracy of information furnished, and (c)

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has relied solely upon (i) the representations set forth in this Agreement and the Merger Agreement, and (ii) its own independent investigations or investigations conducted by its own independent advisers in connection with the accuracy or sufficiency of such information or its investment decision. Investor acknowledges that the investment in Parent is intended to be exempt from registration by virtue of Section 4(a)(2) of the Securities Act. Investor has the financial ability to afford a complete loss of its investment in the LP Interests;

5.8 Investor is acquiring the LP Interests solely for its own account or the accounts of its Affiliates, for investment and not with a view toward resale or other distribution in violation of the Act, and Investor understands that the LP Interests may not be disposed of in contravention of the Securities Act, or any applicable state securities laws;

5.9 Investor is an “accredited investor,” as such term is defined in Regulation D under the Securities Act, with such knowledge and experience in financial and business matters as are necessary in order to evaluate the merits and risks of an investment in the LP Interests;

5.10 Investor understands that the LP Interests are being issued without registration under the Securities Act, under the securities laws of any U.S. state (the “State Acts”) or under the securities laws or laws of similar import of any other country or jurisdiction, in reliance upon exemptions provided by the Securities Act, the State Acts and such other securities laws or laws of similar import, and the regulations promulgated thereunder;

5.11 There are no conditions to Investor’s obligations set forth in this Agreement, except as expressly set forth herein; and

5.12 None of the information, if any, to be supplied by or on behalf of Investor for inclusion in the Proxy Statement or the Schedule 13E-3 will (i) in the case of the Schedule 13E-3 (or any amendment thereof or supplement thereto), as of the date of filing and as of the date of the Company Stockholders’ Meeting, and (ii) in the case of the Proxy Statement (or any amendment thereof or supplement thereto), as of the date of filing or mailing to the Company’s stockholders and as of the date of the Company Stockholders’ Meeting, contain any untrue statement of a material fact or omit to state any material fact required to be stated therein or necessary in order to make the statements therein, in light of the circumstances under which they are made, not misleading.

6. Representations and Warranties of Parent. Parent hereby represents and warrants to Investor, as of the date hereof and as of the Investment Closing, as follows:

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6.1 Parent is limited partnership duly organized, validly existing and in good standing under Delaware Law;

6.2 Parent has all requisite limited partnership power and authority and has received all consents and approvals and taken all action necessary in order to execute and deliver, and perform its obligations under, this Agreement, and to consummate the transactions contemplated by this Agreement;

6.3 This Agreement has been duly executed and delivered by Parent and, assuming the due authorization, execution and delivery of this Agreement by the other Parties, constitutes the valid and binding obligation of Parent, enforceable by Investor against Parent in accordance with its terms, except as may be subject to any bankruptcy, insolvency, reorganization, moratorium, fraudulent transfer or other laws, now or hereafter in effect, relating to or limiting creditor’s generally or by general equitable principles;

6.4 The LP Interests, when issued pursuant to the terms of this Agreement, will be duly authorized, validly issued and outstanding, fully paid, nonassessable and free and clear of all Liens, other than as applicable to the LP Interests or the holders thereof under applicable federal and state securities laws;

6.5 Except for waiver or consents that have been obtained or are in full force an effect, the execution and delivery of this Agreement by Parent and the issuance of the LP Interests contemplated herein will not conflict with, or result in any violation of, or default (with or without notice or lapse of time, or both) under (i) the certificate of formation, limited partner agreement or other organizational documents of Parent or (ii) any law, order or material agreement applicable to Parent or by which any property or asset of Parent is bound or affected or (iii) require any consent or other action by any Person under, constitute a default (or an event that with notice or lapse of time or both would become a default) under, result in any breach of or give rise to any right of termination, cancellation, amendment or acceleration of, any right or obligation under any Contract or otherwise of Parent; and

6.6 At the Investment Closing, Investor will acquire LP Interests pursuant to this Agreement for the same price per LP Interest as Trident is acquiring LP Interests in connection with the Merger.

7. Representations and Warranties of the Initial Investors. Each Initial Investor hereby represents and warrants to Investor, as of the date hereof and as of the Investment Closing, solely with respect to itself, as follows:

7.1 Such Initial Investor is a limited liability company or limited partnership duly organized, validly existing and in good standing under Delaware Law;

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7.2 Such Initial Investor has all requisite limited partnership or limited liability company, as applicable, power and authority and has received all consents and approvals and taken all action necessary in order to execute and deliver, and perform its obligations under, this Agreement, and to consummate the transactions contemplated by this Agreement;

7.3 This Agreement has been duly executed and delivered by such Initial Investor and, assuming the due authorization, execution and delivery of this Agreement by the other Parties, constitutes the valid and binding obligation of such Initial Investor, enforceable by Investor against such Initial Investor in accordance with its terms, except as may be subject to any bankruptcy, insolvency, reorganization, moratorium, fraudulent transfer or other laws, now or hereafter in effect, relating to or limiting creditor’s generally or by general equitable principles;

7.4 Except for waiver or consents that have been obtained or are in full force an effect, the execution and delivery of this Agreement by such Initial Investor will not conflict with, or result in any violation of, or default (with or without notice or lapse of time, or both) under (i) the certificate of formation, limited partner agreement or other organizational documents of such Initial Investor or (ii) any law, order or material agreement applicable to such Initial Investor or by which any property or asset of such Initial Investor is bound or affected or (iii) require any consent or other action by any Person under, constitute a default (or an event that with notice or lapse of time or both would become a default) under, result in any breach of or give rise to any right of termination, cancellation, amendment or acceleration of, any right or obligation under any Contract or otherwise of such Initial Investor; and

7.5 Other than this Agreement and the Interim Investors Agreement (as of the date hereof and made available to Investor), there are no other Contracts between any of the Parent, the Company, either Initial Investor or any of their Affiliates related to the Merger, the terms of either Initial Investor’s investments in Parent or any of the other transactions contemplated by the Merger Agreement, the Interim Investors Agreement or the Equity Documents that have not been made available to Investor (other than in connection with any Permitted Equity Syndication or deemed Permitted Equity Syndication).

8. Pre-Closing Information Rights. Parent agrees from the date hereof until the earlier to occur of the Closing or the valid termination of this Agreement it shall promptly provide to Investor all material information related to the Company or the Merger that has been made available to Parent.

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9. Interim Investors Agreement and LP Agreement

9.1 Provisions Relating to the LP Agreement. In addition to reflecting the terms set forth in the Term Sheet attached as Exhibit A to the Interim Investors Agreement, either the LP Agreement or a side letter issued by Parent to Investor at Closing shall provide:

(a) for the right of Investor to designate a non-voting observer reasonably acceptable to Parent to the board of managers of the General Partner;

(b) for Class A Units held by Investor to participate in the Reserve Development Conversion Adjustment described in the Interim Investors Agreement on the same basis as Trident and other holders of Class A Units;

(c) that Parent shall promptly provide Investor with such information as is reasonably necessary to allow Investor to comply with any tax or regulatory requirements to which it is subject; and

(d) that Investor has the right to transfer the LP Interests to a controlled, majority-owned Affiliate without the consent of Parent’s general partner or any other Person, provided, that such controlled, majority-owned Affiliate transferee executes a joinder to the Equity Documents as required by the Equity Documents.

9.2 Permitted Equity Syndication. Without the prior written consent of Investor, the Initial Investors will not consent to any Permitted Equity Syndication pursuant to the Interim Investors Agreement unless the transferee of equity commitments in such Permitted Equity Syndication receives limited partnership interests of each class in the same proportion as between the different classes of limited partnership interests in Parent and the purchase price per limited partnership interest is the same, in each case, as the limited partnership interests of Parent purchased by Trident and any Affiliate thereof in connection with the closing. Further, without the prior written consent of Investor, Trident shall not agree to amend any of the sections of the Interim Investors Agreement titled “Limited Partnership Units” or “Distributions.”

10. Termination.

10.1 This Agreement will terminate automatically and immediately upon the valid termination of the Merger Agreement in accordance with its terms or upon Trident’s valid termination of its Commitment Letter (as defined in the Interim Investors Agreement), which has not been replaced by a similar commitment by Trident.

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10.2 This Agreement may be terminated (a) at any time prior to the Investment Closing by the mutual written consent of Parent and Investor, (b) by Investor by written notice to the Parent, if (i) a material breach, inaccuracy or failure to be true of any representation or warranty or failure to perform any covenant or agreement on the part of any other Party hereto set forth in this Agreement shall have occurred that would cause any of the conditions set forth in Section 2.1 to be unable to be satisfied or (ii) Parent or the Initial Investors or any of their respective Affiliates amend, restate, modify, waive or take any actions under or with respect to the Merger Agreement or the Interim Investors Agreement, or any of the transaction contemplated thereby, including entering into any side letters or similar Contracts, that would reasonably be expected to have an actual disproportionate adverse effect on Investor as compared to Trident, including such actions that bestow a benefit on Trident that is not proportionally shared by Investor (provided that, any action that affects Parent directly and its investors only indirectly and proportionately shall not give rise to a termination right pursuant to this Section 10.2(b)(ii)) or (c) by Parent by written notice to Investor, if Investor has materially breached any of its representations, warranties, covenants or agreements hereunder.

10.3 If this Agreement is terminated as provided in this Section 10, this Agreement will become null and void and of no further force or effect whatsoever without liability on the part of any Party hereto, and all rights and obligations of any Party hereto shall cease (except that the provisions of this Section 10 and Section 11 will survive any termination of this Agreement); provided, that nothing in this Section 10 will relieve any Party from any liability resulting from its Willful Breach of this Agreement.

11. Miscellaneous.

11.1 Entire Agreement; Amendments, Waivers, Etc. This Agreement embodies the entire agreement and understanding between the Parties relating to the subject matter hereof and supersedes all prior agreements and understandings relating to such subject matter. There are no representations, warranties or covenants by the Parties hereto relating to such subject matter other than those expressly set forth in this Agreement and any writings expressly contemplated or required hereby. This Agreement may not be amended, changed, supplemented, waived or otherwise modified except by an instrument in writing signed by all the Parties hereto.

11.2 Expenses. Each party shall bear its own costs and expenses incurred in connection with the transactions contemplated hereby.

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11.3 Applicable Law; Jurisdiction. This Agreement will be governed by the Delaware Law without regard to the conflicts of law principles thereof. All actions and proceedings arising out of or relating to this Agreement shall be heard and determined in the Court of Chancery of the State of Delaware, and the Parties hereby irrevocably submit to the exclusive jurisdiction of such court (and, in the case of appeals, appropriate appellate courts therefrom) in any such action or proceeding and irrevocably waive the defense of an inconvenient forum to the maintenance of any such action or proceeding. EACH PARTY HERETO ACKNOWLEDGES AND AGREES THAT ANY ACTION ARISING OUT OF OR RELATING TO THIS AGREEMENT IS LIKELY TO INVOLVE COMPLICATED AND DIFFICULT ISSUES, AND THEREFORE EACH SUCH PARTY HEREBY IRREVOCABLY AND UNCONDITIONALLY WAIVES ANY RIGHT SUCH PARTY MAY HAVE TO A TRIAL BY JURY WITH RESPECT TO ANY SUCH ACTION DIRECTLY OR INDIRECTLY ARISING OUT OF OR RELATING TO THIS AGREEMENT OR ANY OF THE TRANSACTIONS CONTEMPLATED HEREBY. EACH OF THE PARTIES HERETO CERTIFIES AND ACKNOWLEDGES THAT (A) NO REPRESENTATIVE, AGENT OR ATTORNEY OF ANY OTHER PARTY HAS REPRESENTED, EXPRESSLY OR OTHERWISE, THAT SUCH OTHER PARTY WOULD NOT, IN THE EVENT OF LITIGATION, SEEK TO ENFORCE EITHER OF SUCH WAIVERS, (B) IT UNDERSTANDS AND HAS CONSIDERED THE IMPLICATIONS OF SUCH WAIVERS, (C) IT MAKES SUCH WAIVERS VOLUNTARILY, AND (D) IT HAS BEEN INDUCED TO ENTER INTO THIS AGREEMENT BY, AMONG OTHER THINGS, THE MUTUAL WAIVERS AND CERTIFICATIONS IN THIS SECTION 11.3.

11.4 Specific Performance. The Parties agree that irreparable damage would occur in the event that any of the provisions of this Agreement were not performed in accordance with their specific terms or were otherwise breached. It is accordingly agreed that each Party shall be entitled to an injunction or injunctions to prevent breaches of this Agreement and to enforce specifically the terms and provisions of this Agreement in the Court of Chancery of the State of Delaware, this being in addition to any other remedy to which such Party is entitled at law or in equity.

11.5 Notices. All notices and other communications under this Agreement must be in writing and will be deemed to have been duly given or made as follows: (a) if delivered in person, on the day of such delivery; (b) if by facsimile, on the day on which such facsimile was sent; provided, that receipt is personally confirmed by telephone; (c) if by electronic mail, on the day on which such electronic mail was sent; (d) if by certified or registered mail (return receipt requested), on the fifth Business Day after the mailing thereof; or (e) if by reputable overnight delivery service, on the second Business Day after the sending thereof:

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If to Parent:

Evergreen Parent, L.P.

c/o AmTrust Financial Services, Inc.

00 Xxxxxx Xxxx, 00xx Xxxxx

Xxx Xxxx, XX 00000

Attention:    Xxxxx Xxxxxxx

Email:          xxxxx.xxxxxxx@xxxxxxxxxxxx.xxx

with a copy (which shall not constitute notice) to:

Trident Pine Acquisition LP

c/o Stone Point GP Ltd.

00 Xxxxxxxxx Xxxx

Xxxxxxxxx, XX 00000

Attention:    Xxxxx Xxxxxxx

Facsimile:    (000) 000-0000

Email:          xxxxxxxx@xxxxxxxxxx.xxx

and

Skadden, Arps, Slate, Xxxxxxx & Xxxx LLP

Xxxx Xxxxx Xxxxxx

Xxx Xxxx, Xxx Xxxx 00000

Attention:    Xxxx X. Xxxxx

    Xxx X. Xxxxxxx

Facsimile:    (000) 000-0000

Email:          xxxx.xxxxx@xxxxxxx.xxx

     xxx.xxxxxxx@xxxxxxx.xxx

and

Xxxx, Weiss, Rifkind, Xxxxxxx & Xxxxxxxx LLP

0000 Xxxxxx xx xxx Xxxxxxxx

Xxx Xxxx, Xxx Xxxx 00000

Facsimile:    (000) 000-0000

Attention:    Xxxx X. Fieldston

    Xxxx X. Xxxxxxx

If to Investor:

Enstar Group Limited

Xxxxxxx Xxxxx, 0xx Xxxxx, 22 Queen Street

Xxxxxxxx XX JX Bermuda

Attention:    Xxxxxx Xxxxxxx

Email:          xxxxxx.xxxxxxx@xxxxxxxxxxx.xxx

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with a copy (which shall not constitute notice) to:

Drinker Xxxxxx & Xxxxx LLP

Xxx Xxxxx Xxxxxx, Xxxxx 0000

Xxxxxxxxxxxx, XX 00000

Attention:    Xxxxxx X. Xxxxxx

Facsimile:    (000) 000-0000

Email:          xxxxxx.xxxxxx@xxx.xxx

11.6 Counterparts. This Agreement may be executed in any number of counterparts, each of which shall be deemed to be an original, but all of which together shall constitute one instrument.

11.7 Successors and Assigns; Assignment. This Agreement and the rights and benefits hereof shall inure to the benefit of each of the Parties hereto and their respective successors and permitted assigns. The rights of Investor hereunder may not be assigned, except that Investor may assign its rights hereunder to a controlled, majority-owned Affiliate of Investor, provided that no such assignment shall relieve Investor of its obligations hereunder. The rights of Parent hereunder may not be assigned without Investor’s prior written consent. Any purported transfer or assignment of any portion of a party’s rights or obligations hereunder in contravention of this Section 11.7 shall be null and void ab initio.

11.8 No Third Party Beneficiaries. Except as expressly set forth in this Agreement, this Agreement is not intended to, and does not, confer any legal or equitable rights or remedies hereunder upon any person other than the parties hereto and their respective successors and permitted assigns.

[SIGNATURE PAGE FOLLOWS]

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IN WITNESS WHEREOF, each of the Parties hereto have caused this Agreement to be executed as of the date first above written.

ENSTAR GROUP LIMITED
By:		/s/ Xxx Xxxxxx
Name: Xxx Xxxxxx
Title:   CFO

Accepted and Agreed as of the date first written above:
EVERGREEN PARENT, L.P.
By: Evergreen GP, LLC, its general partner
By:		/s/ Xxxxx X. Xxxxxxx
		Name:  Xxxxx X. Xxxxxxx
		Title:    Manager

K-Z EVERGREEN, LLC (solely for purposes of Sections 2.1(f), 2.2, 7 and 9)

By:		/s/ Xxxxx X. Xxxxxxx
		Name:  Xxxxx X. Xxxxxxx
		Title:    Manager

TRIDENT PINE ACQUISITION LP (solely for purposes of Sections 2.1(f), 2.2, 7 and 9)

By: Trident Pine GP, LLC, its general partner
By:		/s/ Xxxxx Xxxxxxx
		Name:  Xxxxx Xxxxxxx
		Title:    Manager

Signature Page to Subscription Agreement

Each of the undersigned hereby consents to the terms and conditions of this Agreement and agrees that for purposes of Section 8(c) and Section 16(a) of the Interim Investor’s Agreement, dated as of March 1, 2018, among the undersigned, Trident, Parent, Merger Sub, and the other parties thereto (the “Interim Investors Agreement”), this Agreement shall constitute a Permitted Equity Syndication (as such term is defined in the Interim Investors Agreement).

K-Z EVERGREEN, LLC
By:		/s/ Xxxxx X. Xxxxxxx
		Name: Xxxxx X. Xxxxxxx
		Title:   Manager
TRIDENT PINE ACQUISITION LP
By: Trident Pine GP, LLC, its general partner
By:		/s/ Xxxxx Xxxxxxx
		Name: Xxxxx Xxxxxxx
		Title:   Manager

Signature Page to Subscription Agreement