Document:

EX-10.2

 Exhibit 10.2 
 INVESTORS AGREEMENT 
 THIS INVESTORS AGREEMENT (this
“Agreement”) is made as of July 3, 2013, by and among KENMARE HOLDINGS LTD (together with its controlled Affiliates, “Kenmare”) and TRIDENT V, L.P., TRIDENT V PARALLEL FUND, L.P. and TRIDENT V PROFESSIONALS
FUND, L.P. (collectively, “Trident”). 
 RECITALS 

WHEREAS, ARDEN HOLDINGS LIMITED (company registration number 37470) whose registered office is at Clarendon House, 2 Church Street,
Hamilton, Bermuda (“Arden Holdings”), ALOPUC LIMITED (company registration number 8538477) whose registered office is at Avaya House, 2 Cathedral Hill, Guildford, Surrey, GU2 7YL, UK (“Alopuc”), and Kenmare (company
registration number 30917) whose registered office is at Clarendon House, 2 Church Street, Hamilton, Bermuda, are parties to that certain Agreement for the sale and purchase of the entire issued share capital of Atrium Underwriting Group Limited
(“Atrium”), dated as of June 5, 2013 (the “Atrium Purchase Agreement”); 
 WHEREAS, Arden
Holdings, Kenmare and NORTHSHORE HOLDINGS LIMITED (company registration number 43474) whose registered office is at Clarendon House, 2 Church Street, Hamilton, Bermuda (“Northshore”), are parties to that certain Agreement for the
sale and purchase of the entire issued share capital of Arden Reinsurance Company Limited (“Arden Re”), dated as of June 5, 2013 (the “Arden Re Purchase Agreement”; 

WHEREAS, Northshore is an indirect wholly owned subsidiary of Kenmare that has had no specific operations to date and Alopuc is a newly
formed, wholly owned subsidiary of Northshore; 
 WHEREAS, Kenmare desires to sell to Trident a forty percent
(40%) interest in Northshore such that sixty percent (60%) of Northshore shall be owned by Kenmare and forty percent (40%) of Northshore shall be owned by Trident; 

WHEREAS, on the date hereof, each of Kenmare and Trident has executed a letter agreement in favor of Northshore, in which each party has
agreed, subject to the terms and conditions set forth therein, to make an equity investment in Northshore at the closing of the acquisition of each of Atrium and Arden Re, through a cash equity investment (each, a “Subscription
Letter”), the proceeds of which will be used to fund, in part, the purchase price set forth in each of the Atrium Purchase Agreement and the Arden Re Purchase Agreement, on the terms and subject to the conditions set forth in each such
agreement (such agreements collectively referred to herein as the “Purchase Agreements”); and 
 WHEREAS,
Kenmare and Trident wish to agree to certain terms and conditions that will govern the actions of such parties with respect to the Purchase Agreements and the Subscription Letters and the transactions contemplated thereby. 

 AGREEMENT 
 NOW, THEREFORE, in consideration of the premises, the representations, warranties, covenants and agreements contained herein, the parties hereto agree as follows: 

I. EFFECTIVENESS. 
 Section 1.1 Effectiveness. This Agreement shall become effective on the date hereof and shall terminate (except with respect to this Section 1.1 and Article 3 (other than
Section 3.1), which shall survive termination) upon written agreement of Kenmare and Trident; provided that any liability for failure to comply with the terms of this Agreement prior to the date of termination shall survive the
termination of this Agreement. 
 II. AGREEMENTS AMONG THE INVESTORS. 

Section 2.1 Amendments to the Purchase Agreements. Kenmare and Trident agree that the approval of each of Kenmare and Trident
shall be required in order for Northshore or Alopuc (together, the “Purchasers”) to amend, modify, waive, supplement, terminate or agree to an amendment, modification, waiver or supplement to, or termination of, either of the
Purchase Agreements, and, for the avoidance of doubt, the approval of each of Kenmare and Trident shall be required in order for either Purchaser to waive any condition to closing specified in either of the Purchase Agreements. Any determination by
Kenmare that the closing conditions have been satisfied shall be based on Kenmare’s reasonable determination after consultation with Trident. Kenmare and Trident shall not permit either Purchaser to, without the prior consent of both Kenmare
and Trident, amend, or agree to any amendment of, either of the Purchase Agreements in a manner that would require an amendment to either party’s Subscription Letter. 
 Section 2.2 Debt Financing. Each of Kenmare and Trident shall use its respective reasonable best efforts to assist the Purchasers in obtaining debt financing on terms that are agreeable to
each of Kenmare and Trident. The approval of each of Kenmare and Trident shall be required in order for either of the Purchasers to (i) amend, modify, waive, supplement, terminate or agree to an amendment, modification, waiver, supplement to or
termination of, any agreed-upon terms of the debt financing, or (ii) enter into the definitive documentation providing for such debt financing. 
 Section 2.3 Organizational Documents; Equity Incentive Plans. 
 (a)
Each of Kenmare and Trident agrees to negotiate in good faith with the other party to enter into a final form of Shareholders’ Agreement for the equityholders of Northshore (the “Shareholders’ Agreement”), which agreement
shall be in substantially the form of the Shareholders’ Agreement attached hereto as Exhibit A, and to cause Northshore to create and file with the Bermuda Registrar of Companies an amended and restated Memorandum of Association, if
necessary, and create Amended and Restated Bye-Laws and, as appropriate, other organizational documents, which shall contain standard terms and otherwise be consistent with those set forth in the Shareholders’ Agreement. 

  
 2 

 (b) At the direction of both Kenmare and Trident, Northshore may negotiate and enter into
definitive agreements with members of Atrium’s management team with respect to the terms of equity incentives and/or adopt policies or plans affecting the management of Atrium and Arden Re. 

Section 2.4 Subscription Commitments. Each of Kenmare and Trident hereby affirms and agrees that (i) it is bound by the
provisions set forth in its Subscription Letter, (ii) that Northshore shall be entitled to specifically enforce the provisions of such Subscription Letters and (iii) that Kenmare and Trident shall each have the right to directly enforce
the Subscription Letter of the other party. 
 Section 2.5 Expense Sharing. Each of Kenmare and Trident agrees to
bear its Pro Rata Share (as defined below) of all costs, fees and expenses incurred on or after May 1, 2013 relating to the formation of Northshore and the negotiation and drafting of any amendments to Northshore’s organizational
documents, as well as the costs, fees and expenses incurred by Kenmare and Trident related to due diligence of Atrium and Arden Re, the negotiation of the Purchase Agreements and any ancillary agreements and the consummation of the transactions
contemplated thereby, including all costs, fees and expenses incurred in connection with obtaining any regulatory approvals and debt financing. In addition, Kenmare and Trident shall bear the respective portion of all other costs, fees and expenses
as more specifically set forth on Exhibit B. For purposes of this Section 2.5, “Pro Rata Share” means, with respect to Kenmare, sixty percent (60%), and, with respect to Trident, forty percent (40%). Northshore shall pay
all such costs and expenses as they are funded by Kenmare and Trident through drawdowns hereunder. 
 Section 2.6
Regulatory Filings. Each of Kenmare and Trident hereby represents, warrants and covenants that (i) it will use its respective reasonable best efforts to, and cause Northshore and Alopuc to, timely file all requests for consent, approval
or other authorization of, or any filings with or notifications to, regulatory authorities, as may be required by such regulatory authorities to consummate the transactions contemplated by the Purchase Agreements, and provide any information that is
required of such party in such filings or notifications, and (ii) the information to be supplied by such party in writing in connection with any such requests for consent, approval or other authorization of, or any filings with or notifications
to, regulatory authorities shall be, to its knowledge, accurate and complete in all material respects, and each of Kenmare and Trident agrees that it will promptly notify the other party in writing if at any time or times prior to the termination of
this Agreement such information is, to its knowledge, no longer accurate and complete in all material respects and will promptly update such information so that it is, to its knowledge, accurate and complete in all material respects. If any
regulatory authority asserts any objections related to any consent, approval or authorization required pursuant to any Purchase Agreement, and such objections relate to the activities or investments of such party or such party’s Affiliates,
such party will use its reasonable best efforts to resolve such objections. 

  
 3 

 Section 2.7 Cooperation. Kenmare and Trident shall, and shall cause Northshore
and Alopuc to, use their reasonable best efforts to consummate the transactions contemplated by the Arden Re Purchase Agreement and the Atrium Re Purchase Agreement. 
 Section 2.8 Sale of Northshore Interest. Kenmare agrees to sell, and Trident agrees to purchase, forty percent (40%) of Kenmare’s interest in Northshore (the “Transferred
Interest”) as of the date hereof for a total purchase price of US$40,000. Kenmare represents and warrants to Trident that, prior to the sale, Kenmare was the sole beneficial owner of the Transferred Interest, that the Transferred Interest
was validly issued and fully paid and that there were no encumbrances on the Transferred Interest. Notwithstanding the foregoing, Trident agrees to promptly sell the Transferred Interest back to Kenmare for a total purchase price of US$40,000 if
Trident does not fund any Drawdown required of Trident in accordance with the terms of its Subscription Letter. 
 III.
MISCELLANEOUS. 
 Section 3.1 Representations and Warranties. Each of Kenmare and Trident hereby represents and
warrants to the other party that (a) it has the requisite power and authority to execute, deliver and perform this Agreement and its Subscription Letter, (b) the execution, delivery and performance by it of this Agreement and its
Subscription Letter have been duly authorized by all necessary action and no additional proceedings are necessary to approve such agreements, (c) this Agreement and its Subscription Letter each have been duly executed and delivered by it and
constitute valid and binding agreements of it enforceable against it in accordance with the terms hereof or thereof, and (d) all of the representations and warranties made by it in its Subscription Letter are complete and accurate in all
material respects. Each of Kenmare and Trident further represents and warrants to the other party that its execution, delivery and performance of this Agreement will not (i) conflict with, require a consent, waiver or approval under, or result
in a breach of or default under, any of the terms of any material contract to which such party is a party or by which such party is bound or any of such party’s organizational documents; (ii) violate any order, writ, injunction, decree or
statute, or any rule or regulation, applicable to such party or any of the properties or assets of such party; or (iii) result in the creation of, or impose any obligation on such party to create, any lien, charge or other encumbrance of any
nature whatsoever upon such party’s properties or assets. 
 Section 3.2 Press Release; Communication;
Confidentiality. 
 (a) No press release or other public announcement in respect of this Agreement, the Subscription Letters
or the transactions contemplated by the Purchase Agreements shall be issued or made by either Kenmare or Trident without the prior consent of the other party, except, in each case, for any such press release or other public announcement as Kenmare
may determine in good faith is required to be issued or made by it or any of its Affiliates by applicable law, in which case, Kenmare shall use its commercially reasonable efforts to allow Trident reasonable time to comment on such press release or
other public announcement in advance of such issuance or making. 

  
 4 

 (b) Each of Kenmare and Trident hereby agrees to, and shall cause its representatives to,
keep any information supplied by or on behalf of the other party in connection with the transactions contemplated by this Agreement and the Purchase Agreements confidential (“Confidential Information”) and to use and to cause its
representatives to use the Confidential Information only in connection with the transactions contemplated hereby, including pursuant to the Purchase Agreements; provided that the term Confidential Information shall not include information
that (i) is already in such party’s possession, provided that such information is not subject to another obligation of confidentiality or secrecy, (ii) is or becomes generally available to the public other than as a result of a breach
of this Agreement by such party or its representatives, or (iii) is or becomes available to such party on a non-confidential basis from a source not bound by another obligation of confidentiality or
secrecy; provided, further, that nothing herein shall prevent either party from disclosing Confidential Information to the extent required by applicable law (it being understood that such party shall notify the other party of such
disclosure and use reasonable best efforts to limit such disclosure and to ensure that any information so disclosed is accorded confidential treatment, to the extent available). 

Section 3.3 Amendment. This Agreement may be amended or modified and the provisions hereof may be waived, only by an
agreement in writing signed by each of Kenmare and Trident. 
 Section 3.4 Assignments. The rights and obligations
of the parties hereunder shall not be assigned by either party without the prior written consent of the other party; provided that, a party may assign its rights and obligations under this Agreement and its Subscription Letter to one or more
of its Affiliates if such assignment will not disrupt, interfere with or otherwise delay the receipt of any governmental approval required to be obtained in connection with the consummation of the transactions contemplated by the Arden Re Purchase
Agreement or the Atrium Purchase Agreement; provided, further, that no such assignment shall relieve the assigning party of its obligations hereunder. “Affiliates” shall mean with respect to any party, any other Person
that directly or indirectly, through one or more intermediaries, controls, is controlled by or is under common control with, such party, and “Person” shall include a natural person, corporate or unincorporated body (whether or not
having separate legal personality) and that Person’s personal representatives, successors or permitted assigns. 

Section 3.5 Severability. The provisions of this Agreement are severable and the invalidity or unenforceability of any
provision will not affect the validity or enforceability of the other provisions of this Agreement. If any provision of this Agreement, or the application of that provision to any Person or any circumstance, is invalid or unenforceable, (a) a
suitable and equitable provision will be substituted for that provision in order to carry out, so far as may be valid and enforceable, the intent and purpose of the invalid or unenforceable provision and (b) the remainder of this Agreement and
the application of that provision to any Person or circumstance will not be affected by such invalidity or unenforceability, nor will such invalidity or unenforceability affect the validity or enforceability of that provision, or the application of
that provision, in any other jurisdiction. 

  
 5 

 Section 3.6 Remedies. Any and all remedies expressly conferred upon a party to
this Agreement will be cumulative with, and not exclusive of, any other remedy contained in this Agreement, at law or in equity. The exercise by a party to this Agreement of any one remedy will not preclude the exercise by it of any other remedy.
The parties hereto agree that this Agreement will be enforceable by all available remedies at law or in equity, subject to the limitations expressly set forth herein. No party shall be liable under this Agreement for any consequential, punitive,
special, incidental or indirect damages, except to the extent awarded by a court of competent jurisdiction in connection with a third-party claim. 
 Section 3.7 No Recourse. Notwithstanding anything that may be expressed or implied in this Agreement, each party hereto, by its acceptance of the benefits provided herein, covenants, agrees
and acknowledges that, notwithstanding that any such party or any of its permitted assigns may be a partnership or limited liability company, no rights of recovery, and no recourse hereunder or under any documents or instruments delivered in
connection herewith or in respect of any oral representations made or alleged to be made in connection herewith or therewith, shall be had against any former, current or future direct or indirect equityholders, controlling persons, stockholders,
directors, officers, employees, agents, Affiliates, members, managers, general or limited partners, attorneys or other representatives of any party, or any of its successors or assigns, or any former, current or future direct or indirect
equityholders, controlling persons, stockholders, directors, officers, employees, agents, Affiliates, members, managers, general or limited partners, attorneys or other representatives or successors or assignees of any of the foregoing (but not
including the parties hereto or their respective permitted assigns hereunder, each, an “Investor Related Party” and collectively, the “Investor Related Parties”), through Northshore or otherwise, whether by or
through attempted piercing of the corporate veil, by or through a claim (whether at law or equity or in tort, contract or otherwise) by or on behalf of Northshore against any Investor Related Party, by the enforcement of any assessment or by any
legal or equitable proceeding, by virtue of any applicable law, or otherwise, it being agreed and acknowledged that no personal liability whatsoever shall attach to, be imposed on or otherwise be incurred by any Investor Related Party for any
obligations of such party or any of its successors or permitted assigns under this Agreement or any documents or instrument delivered in connection herewith or in respect of any oral representations made or alleged to be made in connection herewith
or therewith or for any claim (whether at law or equity or in tort, contract or otherwise) based on, in respect of, or by reason of such obligations or their creation. 
 Section 3.8 Third Party Beneficiaries. This Agreement shall be binding upon and inure solely to the benefit of the parties hereto and their respective successors and permitted assigns and
nothing herein, express or implied, is intended to or shall confer upon any Person other than Kenmare and Trident and their respective successors and permitted assigns, any legal or equitable right, benefit or remedy of any nature whatsoever under
or by reason of this Agreement. 

  
 6 

 Section 3.9 Governing Law; Waiver of Jury Trial. 

(a) THIS AGREEMENT AND ALL CLAIMS OR CAUSES OF ACTION (WHETHER AT LAW, IN CONTRACT, IN TORT OR OTHERWISE) THAT MAY BE BASED UPON, ARISING
OUT OF OR RELATING TO THIS AGREEMENT OR ANY OF THE TRANSACTIONS CONTEMPLATED BY THIS AGREEMENT, OR THE NEGOTIATION, EXECUTION OR PERFORMANCE HEREOF, SHALL BE DEEMED TO BE MADE IN AND IN ALL RESPECTS SHALL BE INTERPRETED, CONSTRUED AND GOVERNED BY
AND IN ACCORDANCE WITH THE LAW OF THE STATE OF NEW YORK WITHOUT REGARD TO THE CONFLICTS OF LAW PRINCIPLES THEREOF. The parties hereby irrevocably submit to the personal jurisdiction of the courts of the State of New York and the United States
District Court for the Southern District of New York (the “Chosen Courts”) solely in respect of the interpretation and enforcement of the provisions of this Agreement and of the documents referred to in this Agreement, and in
respect of the transactions contemplated hereby, or the negotiation, execution or performance hereof, and hereby waive, and agree not to assert, as a defense in any action, suit or proceeding for the interpretation or enforcement hereof or of any
such document, that it is not subject thereto or that such action, suit or proceeding may not be brought or is not maintainable in the Chosen Courts or that the Chosen Courts are an inconvenient forum or that the venue thereof may not be
appropriate, or that this Agreement or any such document may not be enforced in or by such Chosen Courts, and the parties hereto irrevocably agree that all claims, actions, suits and proceedings or other causes of action (whether at law, in
contract, in tort or otherwise) that may be based upon, arising out of or relating to this Agreement or any of the transactions contemplated by this Agreement, or the negotiation, execution or performance hereof shall be heard and determined
exclusively in the Chosen Courts. The parties hereby consent to and grant any such Chosen Court jurisdiction over the person of such parties and, to the extent permitted by law, over the subject matter of such dispute and agree that mailing of
process or other papers in connection with any such action, suit or proceeding to the address set forth in Section 3.14 shall be valid, effective and sufficient service thereof. 

(b) EACH PARTY ACKNOWLEDGES AND AGREES THAT ANY CONTROVERSY THAT MAY ARISE UNDER 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 IN RESPECT OF ANY ACTION, SUIT OR PROCEEDING DIRECTLY OR INDIRECTLY ARISING OUT OF OR RELATING TO THIS
AGREEMENT, OR THE TRANSACTIONS CONTEMPLATED BY THIS AGREEMENT. EACH PARTY CERTIFIES AND ACKNOWLEDGES THAT (i) NO REPRESENTATIVE, AGENT OR ATTORNEY OF ANY OTHER PARTY HAS REPRESENTED, EXPRESSLY OR OTHERWISE, THAT SUCH OTHER PARTY WOULD NOT, IN
THE EVENT OF SUCH ACTION, SUIT OR PROCEEDING, SEEK TO ENFORCE THE FOREGOING WAIVER, (ii) EACH PARTY UNDERSTANDS AND HAS CONSIDERED THE IMPLICATIONS OF THIS WAIVER, (iii) EACH PARTY MAKES THIS WAIVER VOLUNTARILY, AND (iv) EACH PARTY
HAS BEEN INDUCED TO ENTER INTO THIS AGREEMENT BY, AMONG OTHER THINGS, THE MUTUAL WAIVERS AND CERTIFICATIONS IN THIS SECTION 3.9(b). 

  
 7 

 Section 3.10 Exercise of Rights and Remedies. No delay of or omission in the
exercise of any right, power or remedy accruing to any party as a result of any breach or default by any other party under this Agreement shall impair any such right, power or remedy, nor shall it be construed as a waiver of or acquiescence in any
such breach or default, or of any similar breach or default occurring later; nor shall any such delay, omission nor waiver of any single breach or default be deemed a waiver of any other breach or default occurring before or after that waiver.

 Section 3.11 Entire Agreement. This Agreement, together with the Shareholders’ Agreement, the Subscription
Letters and the other Exhibits hereto, constitutes the entire agreement, and supersedes all prior agreements, understandings and statements, both written and oral, among the parties or any of their Affiliates with respect to the subject matter
contained herein. 
 Section 3.12 Headings; Counterparts. The section headings contained in this Agreement are for
reference purposes only and shall not be deemed a part of this Agreement or affect in any way the meaning or interpretation of this Agreement. This Agreement may be executed in any number of counterparts, all of which will be one and the same
agreement. 
 Section 3.13 Exclusivity. Each of Kenmare and Trident agrees that for so long as this Agreement shall
remain in effect, without the prior written approval of the other party, it shall not become affiliated with, enter into discussions with, or make any equity investment with, any other Person in relation to any transaction involving an acquisition
of Atrium or Arden Re that could reasonably be expected to be competitive to, or interfere with, the negotiation or consummation of the transactions contemplated by the Purchase Agreements. 

Section 3.14 Notice. All notices or other communications required or permitted to be given hereunder shall be in writing and
shall be delivered by hand or sent by facsimile or other electronic delivery or sent, postage prepaid, by registered, certified or express mail or overnight courier service, as follows: 

if to Kenmare: 

c/o Enstar Group Limited 
 Windsor Place, 3rd Floor 
 22 Queen Street 

Hamilton, Bermuda HM JX 
 Attn: Richard J. Harris 
 Facsimile: 441-296-7319 

  
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 if to Trident: 
 c/o Stone Point Capital LLC 
 20 Horseneck Lane 

Greenwich, CT 06830 
 United States of America 
 Attn: Stephen Levey 

Facsimile: 203-862-2929 
 All
such notices, requests and other communications shall be deemed received on the date of receipt by the recipient thereof if received prior to 5:00 p.m. in the place of receipt and such day is a Business Day. Otherwise, any such notice, request or
communication shall be deemed not to have been received until the next succeeding Business Day. “Business Day” shall mean any day other than a Saturday, Sunday or any day that is a federal holiday in the United States or Bermuda or
a day on which banks in New York City are closed generally. 
 [Signature pages follow] 

  
 9 

 IN WITNESS WHEREOF, each of the undersigned has duly executed this Agreement (or caused this
Agreement to be executed on its behalf by its officer or representative thereunto duly authorized) under seal as of the date first above written. 
  

			
	KENMARE HOLDINGS LTD.
		
	By:	 	/s/ Richard J. Harris
		 	Name: Richard J. Harris
		 	Title: Director

 
			
	TRIDENT V, L.P.
	
	 By: SPC MANAGEMENT HOLDINGS LLC,
         its manager

	
	     By: STONE POINT CAPITAL LLC,
             its managing member

		
	        By:	 	/s/ James D. Carey
		 	Name: James D. Carey
		 	Title: Senior Principal

  

			
	TRIDENT V PARALLEL FUND, L.P.
	
	 By: SPC MANAGEMENT HOLDINGS LLC,
         its manager

	
	         By: STONE POINT CAPITAL LLC,

                its managing member

		
	        By:	 	/s/ James D. Carey
		 	Name: James D. Carey
		 	Title: Senior Principal

  

			
	TRIDENT V PROFESSIONALS FUND, L.P.
	
	 By: SPC MANAGEMENT HOLDINGS LLC,
         its manager

	
	         By: STONE POINT CAPITAL LLC,

                its managing member

		
	        By:	 	/s/ James D. Carey
		 	Name: James D. Carey
		 	Title: Senior Principal

 Exhibit A 
 Shareholders’ Agreement 

 SHAREHOLDERS’ AGREEMENT 

between 

NORTHSHORE HOLDINGS LIMITED 

and 

THE SHAREHOLDERS NAMED HEREIN 

dated as of 

[•], 2013 

 TABLE OF CONTENTS 

 

					
	 Article I Definitions
	  	 	1	  
	 Article II Management and Operation of the Company
	  	 	7	  
	 Section 2.01 Board of Directors.
	  	 	7	  
	 Section 2.02 Voting Arrangements.
	  	 	8	  
	 Section 2.03 Consultation on CEO Matters.
	  	 	10	  
	 Section 2.04 Atrium Underwriting Group Limited.
	  	 	10	  
	 Article III Transfer of Interests
	  	 	10	  
	 Section 3.01 General Restrictions on Transfer.
	  	 	10	  
	 Section 3.02 Right of First Offer.
	  	 	11	  
	 Section 3.03 Drag-along Rights.
	  	 	13	  
	 Section 3.04 Tag-along Rights.
	  	 	15	  
	 Section 3.05 Enstar Call Right and Trident Put Right.
	  	 	18	  
	 Article IV Pre-emptive Rights and Other Agreements
	  	 	20	  
	 Section 4.01 Pre-emptive Right.
	  	 	20	  
	 Section 4.02 Corporate Opportunities.
	  	 	22	  
	 Section 4.03 Confidentiality.
	  	 	22	  
	 Section 4.04 Registration Rights.
	  	 	23	  
	 Article V Information Rights
	  	 	24	  
	 Section 5.01 Financial Statements and Reports.
	  	 	24	  
	 Section 5.02 Inspection Rights.
	  	 	24	  
	 Article VI Representations and Warranties
	  	 	25	  
	 Section 6.01 Representations and Warranties.
	  	 	25	  
	 Article VII Term and Termination
	  	 	26	  
	 Section 7.01 Termination.
	  	 	26	  
	 Section 7.02 Effect of Termination.
	  	 	26	  
	 Article VIII Miscellaneous
	  	 	26	  
	 Section 8.01 Expenses.
	  	 	26	  
	 Section 8.02 Release of Liability.
	  	 	27	  
	 Section 8.03 Notices.
	  	 	27	  
	 Section 8.04 Interpretation.
	  	 	28	  
	 Section 8.05 Headings.
	  	 	28	  
	 Section 8.06 Severability.
	  	 	28	  
	 Section 8.07 Entire Agreement.
	  	 	29	  
	 Section 8.08 Successors and Assigns.
	  	 	29	  
	 Section 8.09 No Third-Party Beneficiaries.
	  	 	29	  
	 Section 8.10 Amendment and Modification; Waiver.
	  	 	29	  
	 Section 8.11 Governing Law.
	  	 	29	  
	 Section 8.12 Submission to Jurisdiction; Waiver of Jury Trial.
	  	 	29	  
	 Section 8.13 Equitable Remedies.
	  	 	30	  
	 Section 8.14 Counterparts.
	  	 	31	  

  
 i 

 SHAREHOLDERS’ AGREEMENT 

This Shareholders’ Agreement (this “Agreement”), dated as of [•], 2013, is entered into among Northshore
Holdings Limited, a Bermuda exempted company (the “Company”), Kenmare Holdings Ltd (the “Enstar Shareholder”), Trident V, L.P., Trident V Parallel Fund, L.P. and Trident V Professionals Fund, L.P. (each, a
“Trident Shareholder” and, collectively, the “Trident Shareholders” and, together with the Enstar Shareholder, the “Initial Shareholders”), each other Person who after the date hereof acquires
Common Shares of the Company and becomes a party to this Agreement by executing a Joinder Agreement (such Persons, collectively with the Initial Shareholders, the “Shareholders”) and, solely for purposes of Section 3.05
hereof, Enstar Group Limited (“Enstar”). 
 RECITALS 

WHEREAS, as of the date hereof, the Enstar Shareholder owns 60% of the issued and outstanding Common Shares of the Company and the Trident
Shareholders collectively own 40% of the issued and outstanding Common Shares of the Company; and 
 WHEREAS, the Initial
Shareholders and the other parties hereto deem it in their best interests and in the best interests of the Company to set forth in this Agreement their respective rights and obligations in connection with their investment in the Company. 

NOW, THEREFORE, in consideration of the mutual covenants and agreements hereinafter set forth and for other good and valuable
consideration, the receipt and sufficiency of which are hereby acknowledged, the parties hereto agree as follows: 
 ARTICLE I

 Definitions 
 Capitalized terms used herein and not otherwise defined shall have the meanings set forth in this Article I. 
 “Affiliate” means with respect to any Person, any other Person who, directly or indirectly (including through one or more intermediaries), controls, is controlled by, or is under
common control with, such Person. For purposes of this definition, “control,” when used with respect to any specified Person, shall mean the power, direct or indirect, to direct or cause the direction of the management and policies of such
Person, whether through ownership of voting securities or partnership or other ownership interests, by contract or otherwise; and the terms “controlling” and “controlled” shall have correlative meanings. 

“Agreement” has the meaning set forth in the preamble. 

 “Applicable Law” means all applicable provisions of
(a) constitutions, treaties, statutes, laws (including the common law), rules, regulations, decrees, ordinances, codes, proclamations, declarations or orders of any Governmental Authority, (b) any consents or approvals of any Governmental
Authority and (c) any orders, decisions, advisory or interpretative opinions, injunctions, judgments, awards, decrees of, or agreements with, any Governmental Authority. 
 “Arden Re” means Arden Reinsurance Company Limited. 

“Atrium” means Atrium Underwriting Group Limited. 

“Board” has the meaning set forth in Section 2.01(a). 

“Business Day” means a day other than a Saturday, Sunday or other day on which commercial banks in Bermuda are
authorized or required to close. 
 “Bye-laws” means the bye-laws of the Company, as amended, modified,
supplemented or restated from time to time in accordance with the terms of this Agreement. 
 “Call
Right” has the meaning set forth in Section 3.05(a). 
 “Change of
Control” means any transaction or series of related transactions (as a result of a tender offer, merger, consolidation or otherwise) that results in, or that is in connection with, (a) any Third Party Purchaser or
“group” (within the meaning of Section 13(d)(3) of the Exchange Act) of Third Party Purchasers acquiring beneficial ownership, directly or indirectly, of all or substantially all of the then issued and outstanding Common Shares or
(b) the sale, lease, exchange, conveyance, transfer or other disposition (for cash, shares of stock, securities or other consideration) of all or substantially all of the property and assets of the Company and its Subsidiaries, on a
consolidated basis, to any Third Party Purchaser or “group” (within the meaning of Section 13(d)(3) of the Exchange Act) of Third Party Purchasers (including any liquidation, dissolution or winding up of the affairs of the Company, or
any other distribution made, in connection therewith). 
 “Commitment Letters” has the meaning set forth in
Section 6.01(e). 
 “Common Shares” means the common shares, par value $1.00 per share, of the
Company and any securities issued in respect thereof, or in substitution therefor, in connection with any stock split, dividend or combination, or any reclassification, recapitalization, merger, consolidation, exchange or similar reorganization.

 “Company” has the meaning set forth in the preamble. 

“Director” has the meaning set forth in Section 2.01(a). 

  
 2 

 “Drag-along Notice” has the meaning set forth in
Section 3.03(b). 
 “Drag-along Sale” has the meaning set forth in
Section 3.03(a). 
 “Drag-along Shareholder” has the meaning set forth in
Section 3.03(a). 
 “Enstar” has the meaning set forth in the preamble. 

“Enstar Director” has the meaning set forth in Section 2.01(a). 

“Enstar Shareholder” has the meaning set forth in the preamble. 

“Exchange Act” means the United States Securities Exchange Act of 1934, as amended, or any successor federal
statute, and the rules and regulations thereunder, which shall be in effect at the time. 
 “Excluded
Securities” means any Common Shares or other equity securities issued in connection with (a) a grant to any existing or prospective consultants, employees, officers or Directors pursuant to any stock option, employee stock
purchase or similar equity-based plans or other compensation agreement; (b) the exercise or conversion of options to purchase Common Shares, or Common Shares issued to any existing or prospective consultants, employees, officers or Directors
pursuant to any stock option, employee stock purchase or similar equity-based plans or any other compensation agreement; (c) any acquisition by the Company of the stock, assets, properties or business of any Person; (d) any merger,
consolidation or other business combination involving the Company; (e) the commencement of any Initial Public Offering or any transaction or series of related transactions involving a Change of Control; (f) a stock split, stock dividend or
any similar recapitalization; or (g) any issuance of Financing Equity. 
 “Exercise Period” has the
meaning set forth in Section 4.01(c). 
 “Exercising Shareholder” has the meaning set forth in
Section 4.01(d). 
 “Fair Market Value” has the meaning set forth in Section 3.05(c).

 “Financing Equity” means any Common Shares, warrants or other similar rights to purchase Common Shares
issued to lenders or other institutional investors (excluding the Shareholders) in any arm’s length transaction providing debt financing to the Company. 
 “Fiscal Year” means for financial accounting purposes, January 1 to December 31. 
 “GAAP” means United States generally accepted accounting principles in effect from time to time. 

  
 3 

 “Government Approval” means any authorization, consent, approval,
waiver, exception, variance, order, exemption, publication, filing, declaration, concession, grant, franchise, agreement, permission, permit, or license of, from or with any Governmental Authority, the giving notice to, or registration with, any
Governmental Authority or any other action in respect of any Governmental Authority. 
 “Governmental
Authority” means any federal, state, local or foreign government or political subdivision thereof, or any agency or instrumentality of such government or political subdivision, or any self-regulated organization or other
non-governmental regulatory authority or quasi-governmental authority (to the extent that the rules, regulations or orders of such organization or authority have the force of Law), or any arbitrator, court or tribunal of competent jurisdiction.

 “Independent Appraiser” has the meaning set forth in Section 3.05(c)(i). 

“Information” has the meaning set forth in Section 4.03(b). 

“Initial Public Offering” means any offering of Common Shares pursuant to a registration statement filed in
accordance with the Securities Act. 
 “Initial Shareholders” has the meaning set forth in the preamble
and shall also include any Permitted Transferees of the Enstar Shareholder and the Trident Shareholders that become Shareholders. 
 “Investors Agreement” has the meaning set forth in Section 6.01(e). 
 “Issuance Notice” has the meaning set forth in Section 4.01(b). 
 “Joinder Agreement” means the joinder agreement in form and substance of Exhibit A attached hereto. 
 “Lien” means any lien, claim, charge, mortgage, pledge, security interest, option, preferential arrangement, right of first offer, encumbrance or other restriction or limitation of
any nature whatsoever. 
 “Lock-up Period” has the meaning set forth in Section 3.01(a).

 “Material Subsidiary” means Arden Re, Atrium and any other material direct or indirect Subsidiary of the
Company. 
 “Memorandum of Association” means the memorandum of association of the Company, as filed on
August 14, 2009 with the Registrar of Companies of Bermuda and as amended, modified, supplemented or restated from time to time in accordance with the terms of this Agreement. 

“New Securities” has the meaning set forth in Section 4.01(a). 

  
 4 

 “Non-exercising Shareholder” has the meaning set forth in Section
4.01(d). 
 “Offered Shares” has the meaning set forth in Section 3.02(a). 

“Offering Shareholder” has the meaning set forth in Section 3.02(a). 

“Offering Shareholder Notice” has the meaning set forth in Section 3.02(b). 

“Organizational Documents” means the Bye-laws and the Memorandum of Association. 

“Over-allotment Exercise Period” has the meaning set forth in Section 4.01(d). 

“Over-allotment New Securities” has the meaning set forth in Section 4.01(d). 

“Over-allotment Notice” has the meaning set forth in Section 4.01(d). 

“Permitted Transferee” means with respect to any Shareholder, any Affiliate of such Shareholder. 

“Person” means an individual, corporation, company, partnership, joint venture, limited liability company,
Governmental Authority, unincorporated organization, trust, association or other entity. 
 “Pre-emptive Pro Rata
Portion” has the meaning set forth in Section 4.01(c). 
 “Pre-emptive Shareholder” has
the meaning set forth in Section 4.01(a). 
 “Proposed Transferee” has the meaning set forth
in Section 3.04(a). 
 “Purchasing Shareholder” has the meaning set forth in
Section 3.02(d). 
 “Put Right” has the meaning set forth in Section 3.05(a).

 “Related Party Agreement” means any agreement, arrangement or understanding between
(a) (i) the Company and (ii) any Shareholder or any Affiliate of a Shareholder or any Director, officer or employee of the Company, as such agreement may be amended, modified, supplemented or restated in accordance with the terms of
this Agreement, and (b) (i) Arden Re, Atrium or any other direct or indirect Subsidiary of the Company and (ii) the Company, any Shareholder or any Affiliate of Arden Re, Atrium, the Company, a Shareholder or any Director, officer or
employee of Arden Re, Atrium or any direct or indirect Subsidiary of the Company, as such agreement may be amended, modified, supplemented or restated in accordance with the terms of this Agreement. 

“Representative” means, with respect to any Person, any and all directors, officers, employees, consultants,
financial advisors, counsel, accountants and other agents of such Person and its Affiliates (provided, that portfolio companies of the Trident Shareholders shall not be Representatives). 

  
 5 

 “ROFO Notice” has the meaning set forth in
Section 3.02(d). 
 “ROFO Notice Period” has the meaning set forth in
Section 3.02(b). 
 “Sale Notice” has the meaning set forth in Section 3.04(b).

 “Securities Act” means the United States Securities Act of 1933, as amended, or any successor federal
statute, and the rules and regulations thereunder, which shall be in effect at the time. 
 “Selling
Shareholder” has the meaning set forth in Section 3.04(a). 
 “Shareholders” has
the meaning set forth in the preamble. 
 “Subsidiary” means with respect to any Person, any other Person
of which a majority of the outstanding shares or other equity interests having the power to vote for directors or comparable managers are owned, directly or indirectly, by the first Person. 

“Tag-along Notice” has the meaning set forth in Section 3.04(c). 

“Tag-along Period” has the meaning set forth in Section 3.04(c). 

“Tag-along Sale” has the meaning set forth in Section 3.04(a). 

“Tag-along Shareholder” has the meaning set forth in Section 3.04(a). 

“Third Party Purchaser” means any Person who, immediately prior to the contemplated transaction, (a) does not
directly or indirectly own or have the right to acquire any outstanding Common Shares or (b) is not a Permitted Transferee of any Person who directly or indirectly owns or has the right to acquire any Common Shares. 

“Transfer” means to, directly or indirectly, sell, transfer, assign, pledge, encumber, hypothecate or similarly
dispose of, either voluntarily or involuntarily, or to enter into any contract, option or other arrangement or understanding with respect to the sale, transfer, assignment, pledge, encumbrance, hypothecation or similar disposition of, any Common
Shares owned by a Person or any interest (including a beneficial interest) in any Common Shares owned by a Person. 

“Trident Director” has the meaning set forth in Section 2.01(a). 

“Trident Shareholder” has the meaning set forth in the preamble. 

“Waived ROFO Transfer Period” has the meaning set forth in Section 3.02(f). 

  
 6 

 ARTICLE II 
 Management and Operation of the Company 
 Section 2.01 Board of
Directors. 
 (a) The Shareholders agree that the business and affairs of the Company shall be managed through a board of
directors (the “Board”) consisting of five members (each, a “Director”). The Directors shall be elected to the Board in accordance with the following procedures: 

(i) The Enstar Shareholder shall have the right to designate three Directors, who shall initially be Paul O’Shea, Nick Packer and
Richard Harris (the “Enstar Directors”); and 
 (ii) The Trident Shareholders shall have the right to designate
two Directors, who shall initially be Darran A. Baird and James D. Carey (the “Trident Directors”). 

Notwithstanding the foregoing, the Enstar Director(s) present at any meeting of the Board or committee thereof shall collectively
exercise voting power equal to the Enstar Shareholder’s percentage ownership of the Company divided by the aggregate percentage ownership of the Company held by the Enstar Shareholder and the Trident Shareholders, and the Trident Director(s)
present at any meeting of the Board or committee thereof shall collectively exercise voting power equal to the Trident Shareholders’ percentage ownership of the Company divided by the aggregate percentage ownership of the Company held by the
Enstar Shareholder and the Trident Shareholders. 
 (b) Each Shareholder shall vote all Common Shares over which such
Shareholder has voting control and shall take all other necessary or desirable actions within such Shareholder’s control (including in its capacity as shareholder, director, member of a board committee or officer of the Company or otherwise,
and whether at a regular or special meeting of the Shareholders or by written consent in lieu of a meeting) to elect to the Board any individual designated by an Initial Shareholder pursuant to Section 2.01(a). 

(c) Each Initial Shareholder shall have the right at any time to remove (with or without cause) any Director designated by such Initial
Shareholder for election to the Board and each other Shareholder shall vote all Common Shares over which such Shareholder has voting control and shall take all other necessary or desirable actions within such Shareholder’s control (including in
its capacity as shareholder, director, member of a board committee or officer of the Company or otherwise, and whether at a regular or special meeting of the Shareholders or by written consent in lieu of a meeting) to remove from the Board any
individual designated by such Initial Shareholder that such Initial Shareholder desires to remove pursuant to this Section 2.01(c). Except as provided in the preceding sentence, unless an Initial Shareholder shall otherwise consent in
writing, no other Shareholder shall take any action to cause the removal of any Director(s) designated by an Initial Shareholder. 

  
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 (d) In the event a vacancy is created on the Board at any time and for any reason (whether
as a result of death, disability, retirement, resignation or removal pursuant to Section 2.01(c)), the Initial Shareholder who designated such individual shall have the right to designate a different individual to replace such Director
and each other Shareholder shall vote all Common Shares over which such Shareholder has voting control and shall take all other necessary or desirable actions within such Shareholder’s control (including in its capacity as shareholder,
director, member of a board committee or officer of the Company or otherwise, and whether at a regular or special meeting of the Shareholders or by written consent in lieu of a meeting) to elect to the Board any individual designated by such Initial
Shareholder. 
 (e) The Board shall have the right to establish any committee of Directors as the Board shall deem appropriate
from time to time. Subject to this Agreement, the Organizational Documents and Applicable Law, committees of the Board shall have the rights, powers and privileges granted to such committee by the Board from time to time. Any delegation of authority
to a committee of Directors to take any action must be approved in the same manner as would be required for the Board to approve such action directly. Any committee of Directors shall be composed of the same proportion of Enstar Directors and
Trident Directors as the Initial Shareholders shall then be entitled to appoint to the Board pursuant to this Section 2.01. 
 (f) The presence of a majority of Directors then in office shall constitute a quorum; provided, that at least one Trident Director is present at such meeting. If a quorum is not achieved at any
duly called meeting, such meeting may be postponed to a time no earlier than 48 hours after written notice of such postponement has been given to the Directors. If no Trident Director is present for three consecutive meetings, then the presence, in
person or by proxy, of Directors designated by Shareholders holding at least 51% of the Common Shares shall constitute a quorum for the next meeting. 
 Section 2.02 Voting Arrangements. In addition to any vote or consent of the Board or the Shareholders of the Company required by Applicable Law, without the consent of the Trident Shareholders
the Company shall not take any action or enter into any commitment to take any action to (and shall cause its Material Subsidiaries to not take any action or enter into any commitment to take any action to): 

(a) amend, modify or waive the Organizational Documents or the charter, bye-laws or other organizational documents of any Material
Subsidiary; 
 (b) make any material changes in the tax or accounting methods or policies or the tax elections of the Company or
any Material Subsidiary (other than as required by Applicable Law or GAAP) that would have a materially adverse impact on the Trident Shareholders; 

  
 8 

 (c) enter into, amend in any material respect, waive or terminate any Related Party
Agreement other than (i) the entry into a Related Party Agreement that is on an arm’s length basis and on terms no less favorable to the Company or the applicable Material Subsidiary than those that could be obtained from an unaffiliated
third party and (ii) any reinsurance or other risk transfer arrangement with any Affiliate of the Enstar Shareholder in which all or substantially all of the underlying insurance risk is borne by the Affiliate of the Enstar Shareholder,
provided, however, that any such reinsurance or other risk transfer transaction provides the Company a market rate fronting fee; 
 (d) enter into or effect any material transaction or series of related transactions outside of the ordinary course of business involving the purchase, lease, license, exchange or other acquisition
(including by merger, consolidation, acquisition of stock or acquisition of assets) by the Company or any Material Subsidiary of any assets and/or equity interests of any Person that are material in amount to the Company and its Subsidiaries taken
as a whole, other than the acquisition by the Company of Arden Re and Atrium; 
 (e) except for a Change of Control effected in
accordance with Section 3.03 which will not require the consent of the Trident Shareholders, enter into or effect any material transaction or series of related transactions outside of the ordinary course of business involving the sale,
lease, license, exchange or other disposition (including by merger, consolidation, sale of stock or sale of assets) by the Company or any Material Subsidiary of any stock or assets that are material in amount to the Company and its Subsidiaries
taken as a whole; 
 (f) grant or authorize the grant of Common Shares or other equity securities of the Company or any
Subsidiary of the Company in an amount greater than 10% of the value of the then-outstanding Common Shares to any existing or prospective officers, directors, employees or consultants of the Company or any Subsidiary of the Company pursuant to any
stock option, employee stock purchase or similar equity-based plans or other compensation agreements; 
 (g) initiate or
consummate an Initial Public Offering or make a public offering and sale of Common Shares or any other securities; or 
 (h)
dissolve, wind-up or liquidate the Company or any Material Subsidiary or initiate a bankruptcy proceeding involving the Company or any Material Subsidiary. 
 For purposes of this Section 2.02, the “ordinary course of business” of the Company and its Subsidiaries shall include the acquisition of insurance and reinsurance companies in
run-off and portfolios of insurance and reinsurance business in run-off. 

  
 9 

 Section 2.03 Consultation on CEO Matters. The Company shall consult with, but
need not obtain the consent of, the Trident Shareholder prior to taking any action or entering into any commitment to take any action to appoint or remove (with or without cause) the Company’s or any Material Subsidiary’s chief executive
officer or enter into or amend any material term of any employment agreement or arrangement with the Company’s or any Material Subsidiary’s chief executive officer. 
 Section 2.04 Atrium Underwriting Group Limited. The Trident Shareholder shall have the right to designate one member of the board of directors of Atrium Underwriting Group Limited. The Initial
Shareholders shall, and shall cause their Director designees to, take all such actions as may be necessary or desirable to give effect to this provision. 
 ARTICLE III 
 Transfer of Interests 

Section 3.01 General Restrictions on Transfer. 
 (a) Except as permitted pursuant to Section 3.01(b), each Shareholder agrees that such Shareholder will not, directly or indirectly, voluntarily or involuntarily Transfer any of its Common
Shares prior to the fifth anniversary of the earlier of the closing of the Company’s acquisition of Arden Re and the closing of the Company’s acquisition of Atrium (the “Lock-up Period”). 

(b) The provisions of Section 3.01(a), Section 3.02, Section 3.03 and Section 3.04 shall
not apply to any of the following Transfers by any Shareholder of any of its Common Shares (i) to a Permitted Transferee or (ii) pursuant to a merger, consolidation or other business combination of the Company with a Third Party Purchaser
that has been approved in compliance with Section 2.02(e). 
 (c) In addition to any legends required by Applicable
Law, each certificate (if any) representing the Common Shares of the Company shall bear a legend substantially in the following form (and if the Common Shares are not certificated, the Company’s ledger shall include a notation substantially in
the following form omitting the reference to a certificate): 
 “THE SECURITIES REPRESENTED BY THIS CERTIFICATE ARE SUBJECT TO A
SHAREHOLDERS’ AGREEMENT (A COPY OF WHICH IS ON FILE WITH THE SECRETARY OF THE COMPANY). NO TRANSFER, SALE, ASSIGNMENT, PLEDGE, HYPOTHECATION OR OTHER DISPOSITION OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE MAY BE MADE EXCEPT IN ACCORDANCE
WITH THE PROVISIONS OF SUCH SHAREHOLDERS’ AGREEMENT AND (A) PURSUANT TO A REGISTRATION STATEMENT EFFECTIVE UNDER THE UNITED STATES SECURITIES ACT OF 1933, AS AMENDED, OR (B) PURSUANT TO AN EXEMPTION FROM REGISTRATION THEREUNDER. THE
HOLDER OF THIS CERTIFICATE, BY ACCEPTANCE OF THIS CERTIFICATE, AGREES TO BE BOUND BY ALL OF THE PROVISIONS OF SUCH SHAREHOLDERS’ AGREEMENT.” 

  
 10 

 (d) Prior notice shall be given to the Company by the transferor of any Transfer (whether or
not to a Permitted Transferee) of any Common Shares. Prior to consummation of any Transfer by any Shareholder of any of its Common Shares, such party shall cause the transferee thereof to execute and deliver to the Company a Joinder Agreement and
agree to be bound by the terms and conditions of this Agreement. Upon any Transfer by any Shareholder of any of its Common Shares, in accordance with the terms of this Agreement, the transferee thereof shall be substituted for, and shall assume all
the rights and obligations under this Agreement of, the transferor thereof. 
 (e) Notwithstanding any other provision of this
Agreement, each Shareholder agrees that it will not, directly or indirectly, Transfer any of its Common Shares (i) except as permitted under the Securities Act and other applicable federal, state or foreign securities laws, and then, if
requested by the Company, only upon delivery to the Company of an opinion of counsel in form and substance satisfactory to the Company to the effect that such Transfer may be effected without registration under the Securities Act or any applicable
foreign securities laws, (ii) if it would cause the Company or any of its Subsidiaries to be required to register as an investment company under the United States Investment Company Act of 1940, as amended, or any comparable foreign law, or
(iii) if it would cause the assets of the Company or any of its Subsidiaries to be deemed plan assets as defined under the United States Employee Retirement Income Security Act of 1974 or its accompanying regulations or any comparable foreign
law or result in any “prohibited transaction” thereunder involving the Company. In any event, the Board may refuse the Transfer to any Person if (i) such Transfer would have a material adverse effect on the Company as a result of any
regulatory or other restrictions imposed by any Governmental Authority or (ii) any non-de minimis adverse tax consequence to the Company, any Subsidiary of the Company, or any Shareholder or any of their Affiliates would result from such
Transfer. 
 (f) Any Transfer or attempted Transfer of any Common Shares in violation of this Agreement shall be null and void,
no such Transfer shall be recorded on the Company’s books and the purported transferee in any such Transfer shall not be treated (and the purported transferor shall continue be treated) as the owner of such Common Shares for all purposes of
this Agreement. 
 Section 3.02 Right of First Offer. 

(a) At any time following the Lock-up Period, and subject to the terms and conditions specified in this Section 3.02, each
Shareholder shall have a right of first offer if any other Shareholder (such Shareholder, an “Offering Shareholder”) proposes to Transfer any Common Shares (the “Offered Shares”) owned by it to any Third Party

  
 11 

 
Purchaser. Following the Lock-up Period, each time the Offering Shareholder proposes to Transfer any Offered Shares (other than Transfers permitted pursuant to Section 3.01 and
Transfers made pursuant to Section 3.03), the Offering Shareholder shall first make an offering of the Offered Shares to the other Shareholders in accordance with the following provisions of this Section 3.02. 

(b) The Offering Shareholder shall give written notice (the “Offering Shareholder Notice”) to the Company and the other
Shareholders stating its bona fide intention to Transfer the Offered Shares and specifying the number of Offered Shares and the material terms and conditions, including the price, pursuant to which the Offering Shareholder proposes to Transfer the
Offered Shares. The Offering Shareholder Notice shall constitute the Offering Shareholder’s offer to Transfer the Offered Shares to the other Shareholders, which offer shall be irrevocable for a period of 20 Business Days (the “ROFO
Notice Period”). 
 (c) By delivering the Offering Shareholder Notice, the Offering Shareholder represents and warrants
to the Company and to each other Shareholder that: (i) the Offering Shareholder has full right, title and interest in and to the Offered Shares; (ii) the Offering Shareholder has all the necessary power and authority and has taken all
necessary action to Transfer such Offered Shares as contemplated by this Section 3.02; and (iii) the Offered Shares are free and clear of any and all Liens other than those arising as a result of or under the terms of this
Agreement. 
 (d) Upon receipt of the Offering Shareholder Notice, each Shareholder receiving such notice shall have until the
end of the ROFO Notice Period to elect to purchase any amount of the Offered Shares by delivering a written notice (a “ROFO Notice”) to the Offering Shareholder and the Company stating that it agrees to purchase such specified
amount of Offered Shares on the terms specified in the Offering Shareholder Notice. Any ROFO Notice shall be binding upon delivery and irrevocable by the applicable Shareholder. Each Shareholder that delivers a ROFO Notice shall be a
“Purchasing Shareholder.” If the Shareholders do not, in the aggregate, elect to purchase all of the Offered Shares by the end of the ROFO Notice Period, each Purchasing Shareholder shall then have the right to purchase all or any
portion of the remaining Offered Shares not elected to be purchased by the Shareholders. As promptly as practicable following the ROFO Notice Period, the Offering Shareholder shall deliver a written notice to each Purchasing Shareholder stating the
number of remaining Offered Shares available for purchase. For a period of 10 Business Days following the receipt of such notice, each Purchasing Shareholder shall have the right to elect to purchase all or any portion of the remaining Offered
Shares by delivering a subsequent ROFO Notice specifying the number of additional Offered Shares it desires to purchase. Notwithstanding the foregoing, the Shareholders may only exercise their rights under this Section 3.02 to purchase
the Offered Shares if, after giving effect to all elections made under this Section 3.02(d), no less than all of the Offered Shares will be purchased by the Purchasing Shareholders. 

  
 12 

 (e) Each Shareholder that does not deliver a ROFO Notice during the ROFO Notice Period shall
be deemed to have waived all of such Shareholder’s rights to purchase the Offered Shares under this Section 3.02. 
 (f) If no Shareholder delivers a ROFO Notice or if the Purchasing Shareholders elect to purchase less than all of the Offered Shares in accordance with Section 3.02(d), the Offering
Shareholder may, during the 180-day period immediately following the expiration of the ROFO Notice Period, which period may be extended for a reasonable time not to exceed 270 days to the extent reasonably necessary to obtain any Government
Approvals (the “Waived ROFO Transfer Period”), and subject to the provisions of Section 3.04, Transfer all of the Offered Shares to a Third Party Purchaser on terms and conditions no more favorable to the Third Party
Purchaser than those set forth in the Offering Shareholder Notice. If the Offering Shareholder does not consummate the Transfer of the Offered Shares within the Waived ROFO Transfer Period, the rights provided hereunder shall be deemed to be revived
and the Offered Shares shall not be offered to any Person unless first re-offered to the Shareholders in accordance with this Section 3.02. 
 (g) Each Shareholder shall take all actions as may be reasonably necessary to consummate any Transfer contemplated by this Section 3.02, including entering into agreements and delivering
certificates and instruments and consents as may be deemed necessary or appropriate. 
 (h) At the closing of any Transfer
pursuant to this Section 3.02, the Offering Shareholder shall deliver to the Purchasing Shareholders the certificate or certificates representing the Offered Shares to be sold (if any), accompanied by stock powers and all necessary stock
transfer taxes paid and stamps affixed, if necessary, against receipt of the purchase price therefor from such Purchasing Shareholders by certified or official bank check or by wire transfer of immediately available funds. 

Section 3.03 Drag-along Rights. 
 (a) If at any time following the Lock-up Period the Enstar Shareholder (together with its Permitted Transferees) holds no less than 55% of the outstanding Common Shares of the Company and receives a bona
fide offer from a Third Party Purchaser to consummate, in one transaction, or a series of related transactions, a Change of Control (a “Drag-along Sale”), the Enstar Shareholder shall have the right to require that each other
Shareholder (each, a “Drag-along Shareholder”) participate in such Transfer in the manner set forth in this Section 3.03, provided, however, that no Drag-along Shareholder shall be required to participate
in the Drag-along Sale if the consideration for the Drag-along Sale is other than cash or registered securities listed on an established U.S. or foreign securities exchange. Notwithstanding anything to the contrary in this Agreement, each Drag-along
Shareholder shall vote in favor of the transaction and take all actions to waive any dissenters, appraisal or other similar rights. 

  
 13 

 (b) The Enstar Shareholder shall exercise its rights pursuant to this
Section 3.03 by delivering a written notice (the “Drag-along Notice”) to the Company and each Drag-along Shareholder no later than 20 days prior to the closing date of such Drag-along Sale. The Drag-along Notice shall
make reference to the Enstar Shareholder’s rights and obligations hereunder and shall describe in reasonable detail: 
 (i)
the number of Common Shares to be sold by the Enstar Shareholder, if the Drag-along Sale is structured as a Transfer of Common Shares; 
 (ii) the identity of the Third Party Purchaser; 
 (iii) the proposed date, time
and location of the closing of the Drag-along Sale; 
 (iv) the per share purchase price and the other material terms and
conditions of the Transfer, including a description of any non-cash consideration in sufficient detail to permit the valuation thereof; and 
 (v) a copy of any form of agreement proposed to be executed in connection therewith. 
 (c) If the Drag-along Sale is structured as a Transfer of Common Shares, then, subject to Section 3.03(d), each Drag-along Shareholder shall Transfer the number of shares equal to the product
of (x) the number of Common Shares held by such Drag-along Shareholder and (y) a fraction (A) the numerator of which is equal to the number of Common Shares the Enstar Shareholder proposes to sell or transfer in the Drag-along Sale
and (B) the denominator of which is equal to the number of Common Shares then held by the Enstar Shareholder. 
 (d) The
consideration to be received by a Drag-along Shareholder shall be the same form and amount of consideration per share of Common Shares to be received by the Enstar Shareholder (or, if the Enstar Shareholder is given an option as to the form and
amount of consideration to be received, the same option shall be given) and the terms and conditions of such Transfer shall, except as otherwise provided in the immediately succeeding sentence, be the same as those upon which the Enstar Shareholder
Transfers its Common Shares. Each Drag-along Shareholder shall make or provide the same representations, warranties, covenants, indemnities and agreements as the Enstar Shareholder makes or provides in connection with the Drag-along Sale (except
that in the case of representations, warranties, covenants, indemnities and agreements pertaining specifically to the Enstar Shareholder, the Drag-along Shareholder shall make the comparable representations, warranties, covenants, indemnities and
agreements 

  
 14 

 
pertaining specifically to itself); provided, that all representations, warranties, covenants and indemnities shall be made by the Enstar Shareholder and each Drag-along Shareholder
severally and not jointly and any indemnification obligation shall be pro rata based on the consideration received by the Enstar Shareholder and each Drag-along Shareholder, in each case in an amount not to exceed the aggregate proceeds received by
the Enstar Shareholder and each such Drag-along Shareholder in connection with the Drag-along Sale. 
 (e) The fees and expenses
of the Enstar Shareholder incurred in connection with a Drag-along Sale and for the benefit of all Shareholders (it being understood that costs incurred by or on behalf of a Enstar Shareholder for its sole benefit will not be considered to be for
the benefit of all Shareholders), to the extent not paid or reimbursed by the Company or the Third Party Purchaser, shall be shared by all the Shareholders on a pro rata basis, based on the aggregate consideration received by each Shareholder;
provided, that no Shareholder shall be obligated to make or reimburse any out-of-pocket expenditure prior to the consummation of the Drag-along Sale. 
 (f) Each Shareholder shall take all actions as may be reasonably necessary to consummate the Drag-along Sale, including entering into agreements and delivering certificates and instruments, in each case
consistent with the agreements being entered into and the certificates being delivered by the Enstar Shareholder. 
 (g) The
Enstar Shareholder shall have 180 days following the date of the Drag-along Notice in which to consummate the Drag-along Sale, on the terms set forth in the Drag-along Notice (which such 180-day period may be extended for a reasonable time not to
exceed 270 days to the extent reasonably necessary to obtain any Government Approvals). If at the end of such period, the Enstar Shareholder has not completed the Drag-along Sale, the Enstar Shareholder may not then effect a transaction subject to
this Section 3.03 without again fully complying with the provisions of this Section 3.03. 

Section 3.04 Tag-along Rights. 
 (a) If at any time following the Lock-up Period a Shareholder (the “Selling Shareholder”) proposes to Transfer any shares of its Common Shares to a Third Party Purchaser (the
“Proposed Transferee”) (and if the Selling Shareholder is the Enstar Shareholder and it cannot or has not elected to exercise its drag-along rights set forth in Section 3.03), each other Shareholder (each, a
“Tag-along Shareholder”) shall be permitted to participate in such Transfer (a “Tag-along Sale”) on the terms and conditions set forth in this Section 3.04. 

(b) Prior to the consummation of any such Transfer of Common Shares described in Section 3.04(a), and after satisfying its
obligations pursuant to Section 3.02, the Selling Shareholder shall deliver to the Company and each other Shareholder a written notice (a “Sale Notice”) of the proposed Tag-along Sale subject to this
Section 3.04 

  
 15 

 
no later than 20 Business Days prior to the closing date of the Tag-along Sale. The Sale Notice shall make reference to the Tag-along Shareholders’ rights hereunder and shall describe in
reasonable detail: 
 (i) the aggregate number of Common Shares the Proposed Transferee has offered to purchase. 

(ii) the identity of the Proposed Transferee; 
 (iii) the proposed date, time and location of the closing of the Tag-along Sale; 

(iv) the per share purchase price and the other material terms and conditions of the Transfer, including a description of any non-cash
consideration in sufficient detail to permit the valuation thereof; and 
 (v) a copy of any form of agreement proposed to be
executed in connection therewith. 
 (c) Each Tag-along Shareholder shall exercise its right to participate in a Transfer of
Common Shares by the Selling Shareholder subject to this Section 3.04 by delivering to the Selling Shareholder a written notice (a “Tag-along Notice”) stating its election to do so and specifying the number of Common
Shares to be Transferred by it no later than five Business Days after receipt of the Sale Notice (the “Tag-along Period”). The offer of each Tag-along Shareholder set forth in a Tag-along Notice shall be irrevocable, and, to the
extent such offer is accepted, such Tag-along Shareholder shall be bound and obligated to Transfer in the proposed Transfer on the terms and conditions set forth in this Section 3.04. The Selling Shareholder and each Tag-along
Shareholder shall have the right to Transfer in a Transfer subject to this Section 3.04 the number of Common Shares equal to the product of (x) the aggregate number of Common Shares the Proposed Transferee proposes to buy as stated
in the Sale Notice and (y) a fraction (A) the numerator of which is equal to the number of Common Shares then held by the Selling Shareholder or such Tag-along Shareholder, as the case may be, and (B) the denominator of which is equal
to the number of shares then held by the Selling Shareholder and each Tag-along Shareholder. 
 (d) Each Tag-along Shareholder
who does not deliver a Tag-along Notice in compliance with Section 3.04(c) above shall be deemed to have waived all of such Tag-along Shareholder’s rights to participate in such Transfer, and the Selling Shareholder shall (subject
to the rights of any participating Tag-along Shareholder) thereafter be free to Transfer to the Proposed Transferee its Common Shares at a per share price that is no greater than the per share price set forth in the Sale Notice and on other terms
and conditions which are not materially more favorable to the Selling Shareholder than those set forth in the Sale Notice without any further obligation to the non-accepting Tag-along Shareholders. 

  
 16 

 (e) Each Tag-along Shareholder participating in a Transfer pursuant to this
Section 3.04 shall receive the same consideration per share as the Selling Shareholder after deduction of such Tag-along Shareholder’s proportionate share of the related expenses in accordance with Section 3.04(g) below.

 (f) Each Tag-along Shareholder shall make or provide the same representations, warranties, covenants, indemnities and
agreements as the Selling Shareholder makes or provides in connection with the Tag-along Sale (except that in the case of representations, warranties, covenants, indemnities and agreements pertaining specifically to the Selling Shareholder, the
Tag-along Shareholder shall make the comparable representations, warranties, covenants, indemnities and agreements pertaining specifically to itself); provided, that all representations, warranties, covenants and indemnities shall be made by
the Selling Shareholder and each Tag-along Shareholder severally and not jointly and any indemnification obligation in respect of breaches of representations and warranties shall be pro rata based on the consideration received by the Selling
Shareholder and each Tag-along Shareholder, in each case in an amount not to exceed the aggregate proceeds received by the Selling Shareholder and each such Tag-along Shareholder in connection with any Tag-along Sale. 

(g) The fees and expenses of the Selling Shareholder incurred in connection with a Tag-along Sale and for the benefit of all Shareholders
(it being understood that costs incurred by or on behalf of the Selling Shareholder for its sole benefit will not be considered to be for the benefit of all Shareholders), to the extent not paid or reimbursed by the Company or the Proposed
Transferee, shall be shared by all the Shareholders participating in the Tag-along Sale on a pro rata basis, based on the aggregate consideration received by each such Shareholder; provided, that no Shareholder shall be obligated to make or
reimburse any out-of-pocket expenditure prior to the consummation of the Tag-along Sale. 
 (h) Each Tag-along Shareholder shall
take all actions as may be reasonably necessary to consummate the Tag-along Sale, including entering into agreements and delivering certificates and instruments, in each case consistent with the agreements being entered into and the certificates
being delivered by the Selling Shareholder. 
 (i) The Selling Shareholder shall have 180 days following the expiration of the
Tag-along Period in which to Transfer the Common Shares described in the Sale Notice, on the terms set forth in the Sale Notice (which such 180-day period may be extended for a reasonable time not to exceed 270 days to the extent reasonably
necessary to obtain any Government Approvals). If at the end of such period, the Selling Shareholder has not completed such Transfer, the Selling Shareholder may not then effect a Transfer of Common Shares subject to this Section 3.04
without again fully complying with the provisions of this Section 3.04. 

  
 17 

 (j) If the Selling Shareholder Transfers to the Proposed Transferee any of its Common Shares
in breach of this Section 3.04, then each Tag-along Shareholder shall have the right to Transfer to the Selling Shareholder, and the Selling Shareholder undertakes to purchase from each Tag-along Shareholder, the number of Common Shares
that such Tag-along Shareholder would have had the right to Transfer to the Proposed Transferee pursuant to this Section 3.04, for a per share amount and form of consideration and upon the terms and conditions on which the Proposed
Transferee bought such Common Shares from the Selling Shareholder, but without indemnity being granted by any Tag-along Shareholder to the Selling Shareholder; provided, that, nothing contained in this Section 3.04 shall preclude
any Shareholder from seeking alternative remedies against such Selling Shareholder as a result of its breach of this Section 3.04. 
 Section 3.05 Enstar Call Right and Trident Put Right. 
 (a) At any
time during the 90-day period following the fifth anniversary of the earlier of the closing of the Company’s acquisition of Arden Re and the closing of the Company’s acquisition of Atrium or at any time following the seventh anniversary of
the earlier of the closing of the Company’s acquisition of Arden Re and the closing of the Company’s acquisition of Atrium, the Enstar Shareholder shall have the right (a “Call Right”) by written notice to the Trident
Shareholders to purchase all, but not less than all, of the Common Shares owned by the Trident Shareholders and their Permitted Transferees. 
 (b) At any time after the seventh anniversary of the earlier of the closing of the Company’s acquisition of Arden Re and the closing of the Company’s acquisition of Atrium, the Trident
Shareholders, acting collectively, shall have the right (the “Put Right”) to require the Enstar Shareholder to purchase all, but not less than all, of the Common Shares held by the Trident Shareholders and their Permitted
Transferees collectively. 
 (c) The purchase price payable by the Enstar Shareholder upon the exercise of the Call Right or the
Put Right, as the case may be, shall be equal to fair market value of the Common Shares held by the Trident Shareholders and their Permitted Transferees calculated based on the overall fair market value of the Company determined on a going concern
basis as between a willing buyer and willing seller with no discount for illiquidity or a minority interest, as such value may be mutually agreed upon by the Enstar Shareholder and the Trident Shareholders or, if no such agreement is reached,
determined in accordance with the procedures set forth below (the “Fair Market Value”): 
 (i) Promptly after
determining that the Enstar Shareholder and the Trident Shareholders are unable to agree upon a Fair Market Value but, in any event, no later than 30 Business Days after the exercise of the Call Right or the Put Right, as the case may be, the
Initial Shareholders shall appoint a mutually acceptable independent 

  
 18 

 
appraiser (the “Independent Appraiser”) to determine the Fair Market Value (determined on a going concern basis as between a willing buyer and a willing seller with no discount
for illiquidity or a minority interest) of the Common Shares held by the Trident Shareholders and their Permitted Transferees. Each of the Enstar Shareholder and the Trident Shareholders (acting together) shall provide the Independent Appraiser with
its respective determination of Fair Market Value, together with the supporting calculations and analyses prepared by such Initial Shareholder with respect thereto. The Initial Shareholders shall instruct the Independent Appraiser to determine, in
writing within 30 days of such Independent Appraiser’s appointment, which of the Initial Shareholders’ determination of Fair Market Value is the more reasonable, and such determination shall be final for all purposes of this
Section 3.05. The costs and expenses of the Independent Appraiser shall be borne equally by the Initial Shareholders. 
 (ii) To enable the Independent Appraiser to conduct the valuation, the Initial Shareholders and the Company shall furnish to the Independent Appraiser such information as the Independent Appraiser may
request, including information regarding the business of the Company and its Subsidiaries and the Company’s assets, properties, financial condition, earnings and prospects. 

(d) Within 90 days after the date of the final determination of the Fair Market Value pursuant to this Section 3.05 (which
period shall be extended solely to the extent needed to obtain any required Government Approvals, provided, that the Shareholders shall, and shall cause their Permitted Transferees to, have used their reasonable best efforts to obtain such
approvals in a timely manner, and provided, further, that in no event shall the Enstar Shareholder be obligated to pay the purchase price for a sale and purchase pursuant to the Put Right in cash due to any failure to obtain any Government
Approvals that are required to permit the Trident Shareholders to acquire or hold any unrestricted ordinary shares of Enstar), the Trident Shareholders shall, and shall cause their Permitted Transferees to, sell to the Enstar Shareholder, free and
clear of any Liens, all of the Common Shares held by them. 
 (e) Each Shareholder shall take all actions as may be reasonably
necessary to consummate the sale contemplated by this Section 3.05, including entering into agreements and delivering certificates and instruments and consents as may be deemed necessary or appropriate. 

(f) At the closing of any sale and purchase pursuant to this Section 3.05, the Trident Shareholders shall, and shall cause
their Permitted Transferees to, deliver to the Enstar Shareholder the certificate or certificates representing their Common Shares (if any), accompanied by stock powers and all necessary stock transfer taxes paid and stamps affixed, if necessary,
against receipt of the purchase price therefor from the Enstar Shareholder by, (i) in the case of a sale and purchase pursuant to the Call Right, wire transfer of immediately available funds, or (ii) in the case of a sale and purchase
pursuant to the Put Right, at the option of the Enstar Shareholder, either (A) wire transfer of 

  
 19 

 
immediately available funds, (B) unrestricted ordinary shares of Enstar (provided that such ordinary shares are then listed or admitted to trading on the NASDAQ Stock Market, the New York
Stock Exchange or another national securities exchange), or (C) a combination of (A) and (B). If the purchase price at the closing of any sale and purchase pursuant to this Section 3.05 consists of unrestricted ordinary shares
of Enstar, the value of such ordinary shares will be deemed to equal the average of the last reported sale price of the ordinary shares over the 10 trading day period ending on, and including, the trading day immediately preceding the effective date
of any such closing. 
 (g) Enstar hereby absolutely, unconditionally and irrevocably guarantees to the Trident Shareholders and
their Permitted Transferees, on the terms and conditions set forth herein, the due and punctual payment, observance, performance and discharge of the Enstar Shareholder’s obligations under this Section 3.05. The Trident Shareholders
hereby agree that in no event shall Enstar be required to pay any amount to the Trident Shareholders or their Permitted Transferees under, in respect of, or in connection with this Agreement other than as expressly set forth herein. 

ARTICLE IV 

Pre-emptive Rights and Other Agreements 
 Section 4.01 Pre-emptive Right. 
 (a) The Company hereby grants
to each Initial Shareholder (each, a “Pre-emptive Shareholder”) the right to purchase its pro rata portion of any new Common Shares (other than any Excluded Securities) (the “New Securities”) that the Company may
from time to time propose to issue or sell to any Person. 
 (b) The Company shall give written notice (an
“Issuance Notice”) of any proposed issuance described in subsection (a) above to the Pre-emptive Shareholders within five Business Days following any meeting of the Board at which any such issuance or sale is approved. The
Issuance Notice shall set forth the material terms and conditions of the proposed issuance, including: 
 (i) the number
of New Securities proposed to be issued and the percentage of the Company’s outstanding Common Shares, on a fully diluted basis, that such issuance would represent; 
 (ii) the proposed issuance date, which shall be at least 20 Business Days from the date of the Issuance Notice; and 
 (iii) the proposed purchase price per share. 
 (c) Each Pre-emptive Shareholder
shall for a period of 15 Business Days following the receipt of an Issuance Notice (the “Exercise Period”) have the right to elect irrevocably to purchase, at the purchase price set forth in the Issuance Notice, up to

  
 20 

 
the amount of New Securities equal to the product of (x) the total number of New Securities to be issued by the Company on the issuance date and (y) a fraction determined by dividing
(A) the number of Common Shares owned by such Pre-emptive Shareholder immediately prior to such issuance by (B) the total number of Common Shares owned by all Initial Shareholders on such date immediately prior to such issuance (the
“Pre-emptive Pro Rata Portion”) by delivering a written notice to the Company. Such Pre-emptive Shareholder’s election to purchase New Securities shall be binding and irrevocable. 

(d) No later than five Business Days following the expiration of the Exercise Period, the Company shall notify each Pre-emptive
Shareholder in writing of the number of New Securities that each Pre-emptive Shareholder has agreed to purchase (including, for the avoidance of doubt, where such number is zero) (the “Over-allotment Notice”). Each Pre-emptive
Shareholder exercising its right to purchase its Pre-emptive Pro Rata Portion of the New Securities in full (an “Exercising Shareholder”) shall have a right of over-allotment such that if any other Pre-emptive Shareholder fails to
exercise its right under this Section 4.01 to purchase its Pre-emptive Pro Rata Portion of the New Securities (each, a “Non-Exercising Shareholder”), such Exercising Shareholder may purchase all or any portion of such
Non-Exercising Shareholder’s allotment (the “Over-allotment New Securities”) by giving written notice to the Company (within five Business Days of receipt of the Over-allotment Notice) setting forth the number of Over-allotment
New Securities that such Exercising Shareholder is willing to purchase (the “Over-allotment Exercise Period”). Such Exercising Shareholder’s election to purchase Over-allotment New Securities shall be binding and irrevocable.
If more than one Exercising Shareholder elects to exercise its right of over-allotment, each Exercising Shareholder shall have the right to purchase the number of Over-allotment New Securities it elected to purchase in its written notice;
provided, that if the over-allotment New Securities are over-subscribed, each Exercising Shareholder shall purchase its pro rata portion of the available Over-allotment New Securities based upon the relative Pre-emptive Pro Rata
Portions of the Exercising Shareholders. 
 (e) The Company shall be free to complete the proposed issuance or
sale of New Securities described in the Issuance Notice with respect to any New Securities not elected to be purchased pursuant to Section 4.01(c) and Section 4.01(d) above in accordance with the terms and conditions set
forth in the Issuance Notice (except that the amount of New Securities to be issued or sold by the Company may be reduced) so long as such issuance or sale is closed within 180 days after the expiration of the Over-allotment Exercise Period (subject
to the extension of such 180-day period for a reasonable time not to exceed 270 days to the extent reasonably necessary to obtain any Government Approvals). In the event the Company has not sold such New Securities within such time period, the
Company shall not thereafter issue or sell any New Securities without first again offering such securities to the Shareholders in accordance with the procedures set forth in this Section 4.01. 

  
 21 

 (f) Upon the consummation of the issuance of any New Securities in accordance with this
Section 4.01, the Company shall deliver to each Exercising Shareholder certificates (if any) evidencing the New Securities, which New Securities shall be issued free and clear of any Liens (other than those arising hereunder or under
Applicable Law and those attributable to the actions of the purchasers thereof), and the Company shall so represent and warrant to the purchasers thereof, and further represent and warrant to such purchasers that such New Securities shall be, upon
issuance thereof to the Exercising Shareholders and after payment therefor, duly authorized and validly issued. Each Exercising Shareholder shall deliver to the Company the purchase price for the New Securities purchased by it by wire transfer of
immediately available funds. Each party to the purchase and sale of New Securities shall take all such other actions as may be reasonably necessary to consummate the purchase and sale including entering into such additional agreements as may be
necessary or appropriate. 
 Section 4.02 Corporate Opportunities. Notwithstanding anything contained in this
Agreement or under Applicable Law to the contrary (to the full extent permitted by Applicable Law), (i) the Initial Shareholders and their respective Affiliates (A) may engage in or possess an interest in other business ventures of any
nature and description (whether similar or dissimilar to the business of the Company or any of its Subsidiaries), independently or with others, and none of the Company, any Subsidiary, any other Shareholder, and each of their respective Affiliates
shall have any right by virtue of this Agreement in or to any such investment or interest of the Enstar Shareholder, the Trident Shareholders, any Enstar Director or any Trident Director and any of its or their respective Affiliates to any income or
profits derived therefrom, and the pursuit of any such venture shall not be deemed wrongful or improper, and (B) shall not be obligated to present any investment opportunity to the Company or any Subsidiary even if such opportunity is of a
character that, if presented to the Company or any Subsidiary, could be taken by the Company or such Subsidiary, and (ii) the parties hereby waive (and the Company shall cause the Subsidiaries to waive) to the fullest extent permitted by law
any fiduciary or other duty of the Initial Shareholders and the Enstar Directors and Trident Directors not expressly set forth in this Agreement, including fiduciary or other duties that may be related to or associated with self-dealing, corporate
opportunities or otherwise, in each case so long as such Person acts in a manner consistent with this Agreement. 

Section 4.03 Confidentiality. 
 (a) Each Shareholder shall and shall cause its Representatives to, keep confidential and not divulge any information (including all budgets, business plans and analyses) concerning the Company, including
its assets, business, operations, financial condition or prospects (“Information”), and to use, and cause its Representatives to use, such Information only in connection with the operation of the Company; provided, that
nothing herein shall prevent any Shareholder from disclosing such Information (i) upon 

  
 22 

 
the order of any court or administrative agency, (ii) upon the request or demand of any regulatory agency or authority having jurisdiction over such Shareholder, (iii) to the extent
compelled by legal process or required or requested pursuant to subpoena, interrogatories or other discovery requests, (iv) to the extent necessary in connection with the exercise of any remedy hereunder, (v) to other Shareholders,
(vi) to such Shareholder’s Representatives that in the reasonable judgment of such Shareholder need to know such Information or (vii) to any potential Permitted Transferee in connection with a proposed Transfer of Common Shares from
such Shareholder as long as such transferee agrees to be bound by the provisions of this Section 4.03 as if a Shareholder, provided, further, that in the case of clause (i), (ii) or (iii), such Shareholder shall notify the
other Shareholders of the proposed disclosure as far in advance of such disclosure as practicable and use reasonable efforts to ensure that any Information so disclosed is accorded confidential treatment, when and if available. 

(b) The restrictions of Section 4.03(a) shall not apply to information that (i) is or becomes generally available to the
public other than as a result of a disclosure by a Shareholder or any of its Representatives in violation of this Agreement; (ii) is or becomes available to a Shareholder or any of its Representatives on a non-confidential basis prior to its
disclosure to the receiving Shareholder and any of its Representatives, (iii) is or has been independently developed or conceived by such Shareholder without use of the Company’s Information or (iv) becomes available to the receiving
Shareholder or any of its Representatives on a non-confidential basis from a source other than the Company, any other Shareholder or any of their respective Representatives, provided, that such source is not known by the recipient of the
information to be bound by a confidentiality agreement with the disclosing Shareholder or any of its Representatives. Furthermore, Section 4.03(a) shall not restrict the Enstar Shareholder and its Affiliates from disclosing any
Information required to be disclosed under applicable securities laws or the rules of any stock exchange upon which their securities are traded. 
 Section 4.04 Registration Rights. Upon the request of any Initial Shareholder in connection with a contemplated public offering of the equity of the Company or any of its Subsidiaries that is
approved in accordance with Section 2.02(g), the Company shall enter into a registration rights agreement with the Initial Shareholders containing customary provisions for a transaction of that type, including demand registration rights
and piggyback registration rights with ratable cutbacks, if necessary, regardless of the demanding party or piggyback party. 

  
 23 

 ARTICLE V 
 Information Rights 
 Section 5.01 Financial Statements and
Reports. In addition to, and without limiting any rights that a Shareholder may have with respect to inspection of the books and records of the Company under Applicable Laws, the Company shall furnish to each Shareholder: 

(a) Within 45 days after the end of each quarterly accounting period, an unaudited consolidated balance sheet as of the end of such
quarterly accounting period and an unaudited related consolidated income statement, consolidated statement of shareholders’ equity and consolidated statement of cash flows for such quarterly accounting period including any footnotes thereto (if
any) prepared in accordance with GAAP, consistently applied, together with comparable year-to-date figures; 
 (b) Within 90
days after the end of each Fiscal Year (or such longer period of time as is approved by the Board), an unaudited consolidated balance sheet as of the end of such Fiscal Year and the related consolidated income statement, consolidated statement of
shareholders’ equity, and consolidated statement of cash flows including all footnotes thereto for such Fiscal Year prepared in accordance with GAAP, consistently applied; and 

(c) Such other financial, accounting or other information relating to the Company and its Subsidiaries or their respective operations as
any Initial Shareholder may reasonably request from time to time in form and substance reasonably acceptable to such requesting Shareholder. 
 Section 5.02 Inspection Rights. 
 (a) The Company shall, and shall
cause its officers, Directors and employees to, (i) afford each Shareholder that, together with any Affiliates and/or Permitted Transferees, owns at least 5% of the Company’s outstanding Common Shares and the Representatives of each such
Shareholder, during normal business hours and upon reasonable notice, reasonable access at all reasonable times to its officers, employees, auditors, properties, offices, plants and other facilities and to all books and records, and (ii) afford
such Shareholder the opportunity to consult with its officers from time to time regarding the Company’s affairs, finances and accounts as each such Shareholder may reasonably request upon reasonable notice. 

(b) The right set forth in Section 5.02(a) above shall not and is not intended to limit any rights which the Shareholders may
have with respect to the books and records of the Company, or to inspect its properties or discuss its affairs, finances and accounts under the laws of the jurisdiction in which the Company is incorporated. 

  
 24 

 ARTICLE VI 
 Representations and Warranties 
 Section 6.01 Representations and
Warranties. Each Shareholder, severally and not jointly, represents and warrants to the Company and each other Shareholder that: 
 (a) Such Shareholder (if an entity) is a corporation, company, partnership or limited liability company duly organized or formed, validly existing and in good standing under the laws of its jurisdiction
of organization. 
 (b) Such Shareholder (if an entity) has full corporate, company or partnership power and authority to
execute and deliver this Agreement, to perform its obligations hereunder and to consummate the transactions contemplated hereby. The execution and delivery of this Agreement, the performance of its obligations hereunder and the consummation of the
transactions contemplated hereby have been duly authorized (if such Shareholder is an entity) by all requisite corporate or company action of such Shareholder. Such Shareholder has duly executed and delivered this Agreement. 

(c) This Agreement constitutes the legal, valid and binding obligation of such Shareholder, enforceable against such Shareholder in
accordance with its terms except as enforceability may be limited by applicable bankruptcy, insolvency, reorganization, moratorium or similar laws affecting the enforcement of creditors’ rights generally and by general equitable principles
(whether enforcement is sought by proceedings in equity or at law). The execution, delivery and performance of this Agreement and the consummation of the transactions contemplated hereby, require no action by or in respect of, or filing with, any
Governmental Authority. 
 (d) The execution, delivery and performance by such Shareholder of this Agreement and the
consummation of the transactions contemplated hereby do not (i) conflict with or result in any violation or breach of any provision of any of the organizational documents of such Shareholder (if an entity), (ii) conflict with or result in
any violation or breach of any provision of any Applicable Law or (iii) require any consent or other action by any Person under any provision of any material agreement or other instrument to which the Shareholder is a party. 

(e) Except for this Agreement, the Investors Agreement by and among the Initial Shareholders, dated as of June 27, 2013 (the
“Investors Agreement”), and the Commitment Letter of each Initial Shareholder to purchase Common Shares, each dated as of June 27, 2013 (the “Commitment Letters”), such Shareholder has not entered into or
agreed to be bound by any other agreements or arrangements of any kind with any other party with respect to the Common Shares, including agreements or arrangements with respect to the acquisition or disposition of the Common Shares or any interest
therein or the voting of the Common Shares (whether or not such agreements and arrangements are with the Company or any other Person). 

  
 25 

 ARTICLE VII 
 Term and Termination 
 Section 7.01 Termination. This Agreement
shall terminate upon the earliest of: 
 (a) the consummation of an Initial Public Offering; 

(b) the consummation of a merger or other business combination involving the Company whereby the Common Shares becomes a security that is
listed or admitted to trading on the NASDAQ Stock Market, the New York Stock Exchange or another national securities exchange; 

(c) the date on which no more than one Shareholder holds any Common Shares; 

(d) the dissolution, liquidation or winding up of the Company; or 

(e) upon the unanimous agreement of the Shareholders. 
 Section 7.02 Effect of Termination. 
 (a) The termination of this
Agreement shall terminate all further rights and obligations of the Shareholders under this Agreement except that such termination shall not effect: 
 (i) the existence of the Company; 
 (ii) the obligation of any Party to pay any
amounts arising on or prior to the date of termination, or as a result of or in connection with such termination; 
 (iii) the
rights which any Shareholder may have by operation of law as a shareholder of the Company; or 
 (iv) the rights contained
herein which by their terms are intended to survive termination of this Agreement. 
 (b) The following provisions shall survive
the termination of this Agreement: this Section 7.02 and Section 4.03, Section 8.03, Section 8.11, Section 8.12 and Section 8.13. 

ARTICLE VIII 
 Miscellaneous 
 Section 8.01 Expenses. Except as otherwise
expressly provided herein or in the Investors Agreement, all costs and expenses, including fees and disbursements of counsel, financial advisors and accountants, incurred in connection with this Agreement and the transactions contemplated hereby
shall be paid by the party incurring such costs and expenses. 

  
 26 

 Section 8.02 Release of Liability. In the event any Shareholder shall Transfer
all of the Common Shares held by such Shareholder in compliance with the provisions of this Agreement without retaining any interest therein, then such Shareholder shall cease to be a party to this Agreement and shall be relieved and have no further
liability arising hereunder for events occurring from and after the date of such Transfer. 
 Section 8.03 Notices.
All notices, requests, consents, claims, demands, waivers and other communications hereunder shall be in writing and shall be deemed to have been given (a) when delivered by hand (with written confirmation of receipt), (b) when received by
the addressee if sent by an internationally recognized overnight courier (receipt requested), (c) on the date sent by facsimile or email of a PDF document (with confirmation of transmission) if sent during normal business hours of the
recipient, and on the next Business Day if sent after normal business hours of the recipient or (d) on the third day after the date mailed, by certified or registered mail, return receipt requested, postage prepaid. Such communications must be
sent to the respective parties at the following addresses (or at such other address for a party as shall be specified in a notice given in accordance with this Section 8.03): 

 

			
	If to the Company:	  	 c/o Enstar Group Limited
 PO
Box 2267
 Windsor Place, 3rd Floor, 22 Queen Street
 Hamilton HM JX Bermuda
 Facsimile: (441) 296-7319

Email: richard.harris@enstargroup.bm
 Attention:
Richard J. Harris, Chief Financial Officer

		
	If to the Enstar Shareholder:	  	 c/o Enstar Group Limited
 PO
Box 2267
 Windsor Place, 3rd Floor, 22 Queen Street
 Hamilton HM JX Bermuda
 Facsimile: (441) 296-7319

Email: richard.harris@enstargroup.bm
 Attention:
Richard J. Harris, Chief Financial Officer

		
	with a copy to (which shall not constitute notice):	  	 Drinker Biddle & Reath LLP
 One Logan Square, Suite 2000
 Philadelphia, PA 19103

Facsimile: (215) 988-2757
 Email:
robert.juelke@dbr.com
 Attention: Robert C. Juelke

  
 27 

			
	If to the Trident Shareholders:	  	 c/o Stone Point Capital LLC

20 Horseneck Lane
 Greenwich, CT 06830

Facsimile: (203) 862-2929
 Email:
slevey@stonepoint.com
 Attention: Stephen Levey

		
	with a copy to (which shall not constitute notice):	  	 c/o Stone Point Capital LLC

20 Horseneck Lane
 Greenwich, CT 06830

Facsimile: (203) 625-8357
 Email:
contracts@stonepoint.com
 Attention: General Counsel

 Section 8.04 Interpretation. For purposes of this Agreement, (a) the words
“include,” “includes” and “including” shall be deemed to be followed by the words “without limitation;” (b) the word “or” is not exclusive; and (c) the words “herein,”
“hereof,” “hereby,” “hereto” and “hereunder” refer to this Agreement as a whole. The definitions given for any defined terms in this Agreement shall apply equally to both the singular and plural forms of the
terms defined. Whenever the context may require, any pronoun shall include the corresponding masculine, feminine and neuter forms. Unless the context otherwise requires, references herein: (x) to Articles, Sections, and Exhibits mean the
Articles and Sections of, and Exhibits attached to, this Agreement; (y) to an agreement, instrument or other document means such agreement, instrument or other document as amended, supplemented and modified from time to time to the extent
permitted by the provisions thereof and (z) to a statute means such statute as amended from time to time and includes any successor legislation thereto and any regulations promulgated thereunder. This Agreement shall be construed without regard
to any presumption or rule requiring construction or interpretation against the party drafting an instrument or causing any instrument to be drafted. The Exhibits referred to herein shall be construed with, and as an integral part of, this Agreement
to the same extent as if they were set forth verbatim herein. 
 Section 8.05 Headings. The headings in this
Agreement are for reference only and shall not affect the interpretation of this Agreement. 
 Section 8.06
Severability. If any term or provision of this Agreement is invalid, illegal or unenforceable in any jurisdiction, such invalidity, illegality or unenforceability shall not affect any other term or provision of this Agreement or invalidate or
render unenforceable such term or provision in any other jurisdiction. Upon such determination that any term or other provision is invalid, illegal or unenforceable, the parties hereto shall negotiate in good faith to modify this Agreement so as to
effect the original intent of the parties as closely as possible in a mutually acceptable manner in order that the transactions contemplated hereby be consummated as originally contemplated to the greatest extent possible. 

  
 28 

 Section 8.07 Entire Agreement. This Agreement, the Organizational Documents, the
Investors Agreement and the Commitment Letters constitute the sole and entire agreement of the parties with respect to the subject matter contained herein and therein, and supersede all prior and contemporaneous understandings and agreements, both
written and oral, with respect to such subject matter. In the event of any inconsistency or conflict between this Agreement and any Organizational Document, the Shareholders and the Company shall, to the extent permitted by Applicable Law, amend
such Organizational Document to comply with the terms of this Agreement. 
 Section 8.08 Successors and Assigns.
This Agreement shall be binding upon and shall inure to the benefit of the parties hereto and their respective successors and permitted assigns. 
 Section 8.09 No Third-Party Beneficiaries. This Agreement is for the sole benefit of the parties hereto and their permitted assigns and nothing herein, express or implied, is intended to or
shall confer upon any other Person or entity any legal or equitable right, benefit or remedy of any nature whatsoever under or by reason of this Agreement. 
 Section 8.10 Amendment and Modification; Waiver. This Agreement may only be amended, modified or supplemented by an agreement in writing signed by each Initial Shareholder; provided,
that any amendment that would materially and adversely affect the rights or duties of a Shareholder shall require the consent of such Shareholder. No waiver by any party of any of the provisions hereof shall be effective unless explicitly set
forth in writing and signed by the party so waiving. No waiver by any party shall operate or be construed as a waiver in respect of any failure, breach or default not expressly identified by such written waiver, whether of a similar or different
character, and whether occurring before or after that waiver. No failure to exercise, or delay in exercising, any right, remedy, power or privilege arising from this Agreement shall operate or be construed as a waiver thereof; nor shall any single
or partial exercise of any right, remedy, power or privilege hereunder preclude any other or further exercise thereof or the exercise of any other right, remedy, power or privilege. 

Section 8.11 Governing Law. This Agreement shall be governed by and construed in accordance with the laws of the State of New
York without giving effect to any choice or conflict of law provision or rule (whether of New York or any other jurisdiction) that would cause the application of the laws of any jurisdiction other than those of New York. 

Section 8.12 Submission to Jurisdiction; Waiver of Jury Trial. 

(a) ANY LEGAL SUIT, ACTION OR PROCEEDING ARISING OUT OF OR BASED UPON THIS AGREEMENT OR THE TRANSACTIONS CONTEMPLATED HEREBY MAY BE
INSTITUTED IN THE FEDERAL COURTS OF THE UNITED STATES OF AMERICA OR 

  
 29 

 
THE COURTS OF THE STATE OF NEW YORK IN EACH CASE LOCATED IN THE CITY OF NEW YORK AND COUNTY OF NEW YORK, AND EACH PARTY IRREVOCABLY SUBMITS TO THE EXCLUSIVE JURISDICTION OF SUCH COURTS IN ANY
SUCH SUIT, ACTION OR PROCEEDING. SERVICE OF PROCESS, SUMMONS, NOTICE OR OTHER DOCUMENT BY MAIL TO SUCH PARTY’S ADDRESS SET FORTH HEREIN SHALL BE EFFECTIVE SERVICE OF PROCESS FOR ANY SUIT, ACTION OR OTHER PROCEEDING BROUGHT IN ANY SUCH COURT.
THE PARTIES IRREVOCABLY AND UNCONDITIONALLY WAIVE ANY OBJECTION TO THE LAYING OF VENUE OF ANY SUIT, ACTION OR ANY PROCEEDING IN SUCH COURTS AND IRREVOCABLY WAIVE AND AGREE NOT TO PLEAD OR CLAIM IN ANY SUCH COURT THAT ANY SUCH SUIT, ACTION OR
PROCEEDING BROUGHT IN ANY SUCH COURT HAS BEEN BROUGHT IN AN INCONVENIENT FORUM. 
 (b) EACH PARTY ACKNOWLEDGES AND AGREES THAT
ANY CONTROVERSY WHICH MAY ARISE UNDER THIS AGREEMENT IS LIKELY TO INVOLVE COMPLICATED AND DIFFICULT ISSUES AND, THEREFORE, EACH SUCH PARTY IRREVOCABLY AND UNCONDITIONALLY WAIVES ANY RIGHT IT MAY HAVE TO A TRIAL BY JURY IN RESPECT OF ANY LEGAL ACTION
ARISING OUT OF OR RELATING TO THIS AGREEMENT OR THE TRANSACTIONS CONTEMPLATED HEREBY. EACH PARTY TO THIS AGREEMENT CERTIFIES AND ACKNOWLEDGES THAT (I) NO REPRESENTATIVE OF ANY OTHER PARTY HAS REPRESENTED, EXPRESSLY OR OTHERWISE, THAT SUCH OTHER
PARTY WOULD NOT SEEK TO ENFORCE THE FOREGOING WAIVER IN THE EVENT OF A LEGAL ACTION, (II) SUCH PARTY HAS CONSIDERED THE IMPLICATIONS OF THIS WAIVER, (III) SUCH PARTY MAKES THIS WAIVER VOLUNTARILY, AND (IV) SUCH PARTY HAS BEEN INDUCED TO ENTER INTO
THIS AGREEMENT BY, AMONG OTHER THINGS, THE MUTUAL WAIVERS AND CERTIFICATIONS IN THIS SECTION 8.12(b). 
 Section 8.13
Equitable Remedies. Each party hereto acknowledges that the other parties hereto would be irreparably damaged in the event of a breach or threatened breach by such party of any of its obligations under this Agreement and hereby agrees that in
the event of a breach or a threatened breach by such party of any such obligations, each of the other parties hereto shall, in addition to any and all other rights and remedies that may be available to them in respect of such breach, be entitled to
an injunction from a court of competent jurisdiction (without any requirement to post bond) granting such parties specific performance by such party of its obligations under this Agreement. 

  
 30 

 Section 8.14 Counterparts. This Agreement may be executed in counterparts, each
of which shall be deemed an original, but all of which together shall be deemed to be one and the same agreement. A signed copy of this Agreement delivered by facsimile, email or other means of electronic transmission shall be deemed to have the
same legal effect as delivery of an original signed copy of this Agreement. 
 [SIGNATURE PAGE FOLLOWS] 

  
 31 

 IN WITNESS WHEREOF, the parties hereto have caused this Agreement to be executed as of the
date first written above by their respective officers thereunto duly authorized. 
  

			
	Northshore Holdings Limited
		
	By:	 	 
	Name:	 	
	Title:	 	

  

			
	Kenmare Holdings Ltd
		
	By:	 	 
	Name:	 	
	Title:	 	

  

			
	Enstar Group Limited (solely for purposes of Section 3.05)
		
	By:	 	 
	Name:	 	
	Title:	 	

 
			
	 Trident V, L.P.
  

By: SPC Management Holdings, its manager
 By:
Stone Point Capital LLC, its managing member

		
	By:	 	 
	Name:	 	James D. Carey
	Title:	 	Senior Principal

  

			
	 Trident V Parallel Fund, L.P.
  

By: SPC Management Holdings, its manager
 By:
Stone Point Capital LLC, its managing member

		
	By:	 	 
	Name:	 	James D. Carey
	Title:	 	Senior Principal

  

			
	 Trident V Professionals Fund, L.P.
  

By: SPC Management Holdings, its manager
 By:
Stone Point Capital LLC, its managing member

		
	By:	 	 
	Name:	 	James D. Carey
	Title:	 	Senior Principal

 EXHIBIT A 
 Joinder Agreement 
 Reference is hereby made to the Shareholders’
Agreement, dated as June [•], 2013 (as amended from time to time, the “Shareholders’ Agreement”), by and among Kenmare Holdings Ltd, Trident V, L.P., Trident V Parallel Fund, L.P. and Trident V Professionals Fund, L.P.,
Northshore Holdings Limited, a Bermuda exempted company (the “Company”), and, solely for purposes of Section 3.05 thereof, Enstar Group Limited. Pursuant to and in accordance with Section 3.01(d) of the Shareholders’
Agreement, the undersigned hereby agrees that upon the execution of this Joinder Agreement, it shall become a party to the Shareholders’ Agreement and shall be fully bound by, and subject to, all of the covenants, terms and conditions of the
Shareholders’ Agreement as though an original party thereto and shall be deemed to be a Shareholder of the Company for all purposes thereof. 
 Capitalized terms used herein without definition shall have the meanings ascribed thereto in the Shareholders’ Agreement. 
 IN WITNESS WHEREOF, the parties hereto have executed this Agreement as of [DATE]. 
  

			
	Northshore Holdings Limited
		
	By:	 	 
	Name:	 	
	Title:	 	

  

			
	[Transferee Shareholder]
		
	By:	 	 
	Name:	 	
	Title:EX-10.3

 Exhibit 10.3 
 July 3, 2013 
 Northshore Holdings Limited 

c/o Enstar Group Limited 
 Windsor Place, 3rd
Floor 
 22 Queen Street 
 Hamilton,
Bermuda HM JX 
 Re:     Commitment to Purchase Common Shares 

Ladies and Gentlemen: 

Reference is made to the Investors Agreement (the “Investors Agreement”), dated as of July 3, 2013, by and among
KENMARE HOLDINGS LTD (“Kenmare”), TRIDENT V, L.P., TRIDENT V PARALLEL FUND, L.P. and TRIDENT V PROFESSIONALS FUND, L.P. (collectively, “Trident”) and the Purchase Agreements (as defined in the Investors Agreement).
Capitalized terms used and not defined herein but defined in the Investors Agreement shall have the meanings ascribed to them in the Investors Agreement. 
 This letter agreement (this “Agreement”) sets forth the commitment of Kenmare with respect to the proposed issuance and sale by Northshore Holdings Limited (company registration number
43474) whose registered office is at Clarendon House, 2 Church Street, Hamilton, Bermuda (“Northshore”), and the proposed purchase by Kenmare (and/or one or more of its Permitted Assigns) of common shares in the capital of
Northshore designated as Common Shares (the “Common Shares”) at such times as set forth herein. Contemporaneously herewith, Trident is delivering to Northshore a letter agreement in substantially the form of this Agreement (the
“Trident Subscription Letter”), pursuant to which Trident is committing to purchase Common Shares concurrent with purchases of Common Shares by Kenmare. 
 1. Commitment. Kenmare hereby commits, subject to the terms and conditions set forth herein, including (without limitation) those set forth in Paragraph 2(c) and Paragraph 3 hereof, that it shall
purchase, or shall cause its Permitted Assigns to purchase, Common Shares for an aggregate amount equal to Kenmare’s Total Subscription Commitment set forth on Schedule A hereto (the “Total Subscription Commitment”), for the
purposes of funding a portion of the purchase price pursuant to and in accordance with the Purchase Agreements, together with related expenses. Kenmare shall promptly use its reasonable best efforts to obtain, or cause to be obtained, all consents,
authorizations, orders and approvals from all governmental authorities that may be or become necessary for the performance of its obligations pursuant to this Agreement or the consummation of the transactions contemplated by the Purchase Agreements.
Kenmare shall cooperate fully with Trident and Northshore and their Affiliates in promptly seeking to obtain all such consents, authorizations, orders and approvals. Kenmare shall not willfully take any action that will have the effect of delaying,
impairing or impeding the receipt of any required consents, authorizations, orders and approvals. 

  
 1 

 2. Drawdowns. 

(a) At any time and from time to time following the date hereof and subject to the terms and conditions set forth herein, including
(without limitation) those set forth in Paragraph 2(c) and Paragraph 3 hereof, Northshore may require Kenmare to purchase Common Shares (each such purchase, a “Drawdown”), at a purchase price of US$1,000 per share (as such price may
be adjusted for any stock splits, subdivisions, combinations, recapitalizations and the like, including any of the foregoing effected by means of a merger or similar transaction) in satisfaction of part or all of the unpaid portion of Kenmare’s
Total Subscription Commitment. With respect to any Drawdown, Northshore shall cause the amount of Trident’s and Kenmare’s portion of the Drawdown to be an amount equal to Trident’s or Kenmare’s Pro Rata Percentage (as set forth
on Schedule A attached hereto) multiplied by the aggregate amount of the Drawdown. Northshore shall exercise its rights pursuant to this Paragraph 2 by delivering to Kenmare a written notice (a “Drawdown Notice”) no later
than five (5) Business Days (as defined below) preceding the closing date of the Drawdown (the “Drawdown Date”). The Drawdown Notice shall make reference to Kenmare’s obligations hereunder and shall set forth: (i) the
number of Common Shares required to be purchased by Kenmare; (ii) the terms and conditions of the purchase (which shall not alter the terms and conditions set forth in this Agreement), including the aggregate number of Common Shares to be
purchased by Trident and Kenmare; (iii) wire transfer instructions; and (iv) the Drawdown Date. The Drawdown Notice shall be delivered to Kenmare in the manner provided in Paragraph 14 hereof. 

(b) After receipt of a Drawdown Notice pursuant to Paragraph 2(a), Kenmare shall purchase on the Drawdown Date, at a purchase price of
US$1,000 per share (as such price may be adjusted for any stock splits, subdivisions, combinations, recapitalizations and the like, including any of the foregoing effected by means of a merger or similar transaction), that number of Common Shares as
is stated in the Drawdown Notice delivered to Kenmare. Subject to the terms and conditions of this Agreement, and in reliance upon the representations and warranties contained herein, Kenmare shall deliver to Northshore consideration for such
Drawdown no later than 11:00 a.m. Eastern time on the Drawdown Date by wire transfer of immediately available funds to the account designated by Northshore in accordance with the wire transfer instructions set forth in the Drawdown Notice relating
to such Drawdown. On the Drawdown Date, upon the receipt by Northshore of Kenmare’s full consideration for such Drawdown, Northshore shall issue and deliver (or, if the Common Shares are uncertificated, record on the books of Northshore) a new,
duly executed certificate or duly executed certificates to Kenmare evidencing that number of Common Shares issued to Kenmare pursuant to such Drawdown. 
 (c) Northshore may require a Drawdown only in connection with the consummation of the transactions contemplated by the Purchase Agreements. In no event shall the sum of the portion of all Drawdowns funded
by Kenmare in accordance with this Agreement exceed Kenmare’s Total Subscription Commitment. 

  
 2 

 (d) Kenmare’s obligation to purchase Common Shares and its obligation to fund all or
any portion of its unfunded Total Subscription Commitment shall expire on the earliest of (i) the written agreement of each of Kenmare and Trident; and (ii) the valid termination of each of the Purchase Agreements in accordance with its
terms. Upon expiration of Kenmare’s obligations, this Agreement shall terminate and Kenmare shall not have any further obligations or liabilities hereunder. 
 (e) The closing of the issuance, sale and purchase by Kenmare of the Common Shares in each Drawdown shall take place at the offices of Northshore, or remotely via the electronic or other exchange of
documents and signature pages, contemporaneously with the closing of the issuance, sale and purchase by Trident of the Common Shares in each Drawdown, or at such other place or such other date as agreed to by the parties hereto. 

3. Conditions to the Purchase of Common Shares. The obligation of Kenmare to fund its Pro Rata Percentage of any Drawdown is
subject to the satisfaction or waiver (if permitted by applicable law, rule, regulation or order) on or prior to the applicable Drawdown Date of the following conditions: 
 (a) Northshore shall be in good standing. 
 (b) If the Drawdown relates to the
acquisition of Atrium, each of the closing conditions set forth in the Atrium Purchase Agreement shall have been satisfied or waived in accordance with the terms of the Atrium Purchase Agreement and Section 2.1 of the Investors Agreement.

 (c) If the Drawdown relates to the acquisition of Arden Re, each of the closing conditions set forth in the Arden Re
Purchase Agreement shall have been satisfied or waived in accordance with the terms of the Arden Re Purchase Agreement and Section 2.1 of the Investors Agreement. 
 (d) The representations and warranties of Northshore made in Paragraph 6 hereof shall be true and correct in all material respects as of the applicable Drawdown Date, except where the failure to be true
and correct arises from the identity or the legal or regulatory status of Kenmare. 
 (e) None of Northshore or any material
subsidiary of Northshore shall have: (i) commenced a voluntary case or other proceeding or filed any petition seeking liquidation, reorganization or other similar relief under any bankruptcy, reorganization, insolvency, dissolution, liquidation
or other similar law now or hereafter in effect or sought the appointment of a custodian, trustee, receiver, liquidator or other similar official of Northshore or any material subsidiary or any substantial part of Northshore’s or any material
subsidiary’s property; (ii) consented to the institution of, or failed to contest in a prompt manner, any proceeding or petition described in clause (i) above; (iii) applied for or consented to the appointment of a custodian,
trustee, receiver, conservator, liquidator or other similar official for Northshore or for any material subsidiary or for a substantial part of Northshore’s or any material 

  
 3 

 
subsidiary’s assets; (iv) filed an answer admitting the material allegations of a petition filed against Northshore or any material subsidiary in any such proceeding; (v) made a
general assignment for the benefit of Northshore’s or any material subsidiary’s creditors as a result of a bankruptcy, reorganization, insolvency, dissolution, liquidation or similar event; (vi) adopted any resolution of the Board of
Directors of Northshore or any resolution of the board of directors (or comparable governing body) of any material subsidiary for the primary purpose of effecting any of the foregoing; or (vii) admitted in writing generally its inability to pay
its debts as they come due. No involuntary proceeding (which remains undismissed) shall have been commenced and no involuntary petition (which remains undismissed) shall have been filed seeking or resulting in: (y) liquidation, reorganization
or other similar relief in respect of Northshore or any material subsidiary of Northshore or any of Northshore’s or any material subsidiary’s debts, or any substantial part of Northshore’s or any subsidiary’s assets, under any
bankruptcy, reorganization, insolvency, dissolution, liquidation or other similar law now or hereafter in effect; or (z) the appointment of a custodian, trustee, receiver, conservator, liquidator or other similar official for Northshore or for
any material subsidiary or a substantial part of Northshore’s or any material subsidiary’s assets, and in each such case, such proceeding or appointment shall remain undismissed as of the applicable Drawdown Date. No order, judgment or
decree adjudicating Northshore or any subsidiary of Northshore bankrupt or insolvent shall have been entered and no order for relief under any bankruptcy, reorganization, insolvency, dissolution, liquidation or other similar law now or hereafter in
effect shall have been entered against Northshore or any material subsidiary and shall be in effect and not dismissed as of the applicable Drawdown Date. 
 (f) The purchase, sale and issuance of Common Shares to Kenmare on the applicable Drawdown Date (i) shall not be prohibited by any applicable law, rule, regulation or order, and (ii) Kenmare
shall have obtained all necessary regulatory approvals applicable to it to permit the purchase of the Common Shares and Kenmare’s direct or indirect ownership of equity interests of each of Northshore and, as applicable, Arden Re and Atrium,
and all applicable waiting periods with respect thereto shall have expired or been terminated. 
 (g) Northshore and Trident
shall be in compliance with all of their respective covenants and agreements under the Trident Subscription Letter, and Kenmare shall be in compliance with its covenants and agreements under the Investors Agreement, in each case, in all material
respects. 
 4. Assignment. The rights and obligations of the parties hereunder shall not be assigned by Northshore or
Kenmare without the prior written consent of Kenmare and Trident; provided that, Kenmare may assign its rights and obligations under this Agreement to one or more of its Affiliates if such assignment will not disrupt, interfere with or
otherwise delay the receipt of any governmental approval required to be obtained in connection with the consummation of the transactions contemplated by the Purchase Agreements (“Permitted Assigns”); provided, further,
that no such assignment shall relieve the assigning party of its obligations hereunder. 

  
 4 

 5. Limited Recourse; Enforcement. 

(a) Notwithstanding anything that may be expressed or implied in this Agreement, each party hereto, by its acceptance of the benefits
hereof, covenants, agrees and acknowledges that, notwithstanding that any such party may be a partnership, no recourse hereunder or any documents or instruments delivered in connection herewith shall be had against any former, current or future
officer, agent or employee of any such party or any director, officer, employee, partner, Affiliate or assignee thereof, whether by or through piercing of the corporate veil, whether by the enforcement of any assessment or by any legal or equitable
proceedings, or by virtue of any statute, regulation or other applicable law, it being expressly agreed and acknowledged that no personal liability whatsoever shall attach to, be imposed on, or otherwise be incurred by any such affiliated Person, as
such for any obligations of a party under this Agreement or the transactions contemplated hereby, under any documents or instruments delivered in connection herewith, in respect of any oral representation made or alleged to be made in connection
herewith or therewith, or for any claim based on, in respect of, or by reason of, such obligations or their creation. 
 (b)
Notwithstanding anything that may be expressed or implied in this Agreement or any document or instrument delivered contemporaneously herewith, Northshore, by its acceptance of the benefits of the commitment provided herein, covenants, agrees and
acknowledges that no Person other than Kenmare and its respective permitted assigns hereunder shall have any obligation hereunder or in connection with the transactions contemplated hereby and that, notwithstanding that Kenmare or any of its
respective permitted assigns may be a partnership or limited liability company, Northshore has no rights of recovery against, and no recourse hereunder or under any documents or instruments delivered in connection herewith or in respect of any oral
representations made or alleged to be made in connection herewith or therewith shall be had against, any former, current or future direct or indirect equityholders, controlling persons, stockholders, directors, officers, employees, agents,
Affiliates, members, managers, general or limited partners, attorneys or other representatives of Kenmare, or any of their successors or assigns, or any former, current or future direct or indirect equityholders, controlling persons, stockholders,
directors, officers, employees, agents, Affiliates, members, managers, general or limited partners, attorneys or other representatives or successors or assignees of any of the foregoing (but not including Kenmare and its permitted assigns hereunder,
each, an “Investor Related Party” and collectively, the “Investor Related Parties”), through Northshore or otherwise, whether by or through attempted piercing of the corporate veil, by or through a claim (whether at
law or equity or in tort, contract or otherwise) by or on behalf of Northshore against any Investor Related Party, by the enforcement of any assessment or by any legal or equitable proceeding, by virtue of any applicable law, or otherwise, it being
agreed and acknowledged that no personal liability whatsoever shall attach to, be imposed on or otherwise be incurred by any Investor Related Party for any obligations of Kenmare or any of its successors or permitted assigns under this Agreement or
any documents or instrument delivered in connection herewith or in respect of any oral representations made or alleged to be made in connection herewith or therewith or for any claim (whether at law or equity or in tort, contract or otherwise) based
on, in respect of, or by reason of such obligations or their creation. 

  
 5 

 (c) This Agreement may only be enforced by Northshore and Trident. Without limiting the
foregoing, none of Northshore’s equityholders (other than Trident), creditors or counterparties or any creditors or counterparties of any subsidiary of Northshore shall have any right to enforce this Agreement or to cause Northshore to enforce
this Agreement. 
 6. Representations and Warranties of Northshore. Northshore hereby represents and warrants to Kenmare
as of the date hereof and as of each Drawdown Date, that: 
 (a) (i) Northshore is duly organized, validly existing and in good
standing under the laws of Bermuda. As of the date hereof and prior to funding pursuant to the initial Drawdown, Northshore’s net assets are US$100,000 in cash. (ii) Northshore has the requisite company power to execute, deliver and
perform its obligations under this Agreement, the Trident Subscription Letter and the Shareholders’ Agreement and has taken all necessary action to authorize such execution, delivery and performance. This Agreement, the Trident Subscription
Letter and the Shareholders’ Agreement have been duly executed and delivered by Northshore and, assuming due authorization, execution and delivery of each such agreement by Trident and Kenmare (as appropriate), each such agreement constitutes a
valid and binding agreement of Northshore enforceable against Northshore in accordance with its terms, except to the extent that such enforcement may be subject to (x) applicable bankruptcy, insolvency, fraudulent conveyance, reorganization,
moratorium and other similar laws relating to or affecting creditors’ rights generally and (y) general equitable principles (whether considered in a proceeding in equity or at law). (iii) Except as have already been made or obtained
or as may be required prior to the closing for the applicable Drawdown Date, no notices, reports or other filings are required to be made by Northshore with, nor are any consents, registrations, approvals, permits, orders, licenses or authorizations
required to be obtained by it from, any governmental authority or any other Person in connection with the execution, delivery and performance by it of this Agreement, the Trident Subscription Letter and the Shareholders’ Agreement and the
consummation by it of the transactions contemplated hereby and thereby. (iv) The execution, delivery and performance by Northshore of this Agreement, the Trident Subscription Letter and the Shareholders’ Agreement do not and will not, and
the consummation by Northshore of the transactions contemplated by this Agreement, the Trident Subscription Letter and the Shareholders’ Agreement will not, with or without the giving of notice, the lapse of time, or both, (x) violate or
conflict with Northshore’s organizational documents; (y) violate or conflict in any material respects with any applicable law with respect to Northshore; or (z) breach or result in a default under, permit the termination of, or permit
the acceleration of the performance required by, any contract of Northshore, except, in the case of this clause (z), such instances as would not have a material adverse effect on Northshore’s assets, financial condition, results from operations
or business. 

  
 6 

 (b) Once issued to Kenmare as provided in this Agreement, the Common Shares (i) will
have been duly authorized and validly issued; (ii) will be fully paid and nonassessable; and (iii) in reliance upon Kenmare’s representations, warranties and acknowledgments set forth in Paragraph 7 hereof, will have been issued in
compliance with all applicable laws concerning the issuance of securities or exemptions thereunder; provided, however, that the Common Shares may be subject to restrictions on transfer as set forth in the Shareholders’ Agreement
or as otherwise required by applicable law at the time such transfer is proposed. 
 (c) As of the date hereof, except for the
commitments to sell Common Shares pursuant to the Trident Subscription Letter, or as described in the Shareholders’ Agreement, no shares of capital stock of Northshore are subject to any preemptive rights, resale rights, rights of first refusal
or similar rights. 
 (d) As of the date hereof, (i) Northshore is party to no contracts or side letters, other than the
Arden Re Purchase Agreement, the Trident Subscription Letter and the Shareholders’ Agreement and any ancillary agreements referred to therein and (ii) each of this Agreement and the Trident Subscription Letter is identical, except that the
Pro Rata Percentages and the Total Subscription Commitments shall vary by investor and with other changes necessary to reflect the identities of the applicable investor. 
 (e) As of the date hereof and the date of the initial Drawdown, Northshore has not engaged in any business activities or conducted any operations other than in connection with the transactions
contemplated hereby and under the Investors Agreement, the Trident Subscription Letter, the Shareholders’ Agreement, the Arden Re Purchase Agreement and the Atrium Purchase Agreement. As of the date hereof, Northshore has no subsidiaries other
than Alopuc and no obligations other than the obligations set forth in the Arden Re Purchase Agreement (and indirectly through its ownership of Alopuc under the Atrium Purchase Agreement), this Agreement, the Investors Agreement, the Trident
Subscription Letter and the Shareholders’ Agreement. 
 (f) The foregoing representations and warranties (i) are,
with the exception of clause (a)(iii) of this Paragraph 6 to the extent that any required notices, reports or other filings or any required consents, registrations, approvals, permits, orders, licenses or authorizations remain to be made or obtained
prior to the closing of a Drawdown, true and accurate as of the date hereof; (ii) shall be true and accurate as of the date of the closing for the initial Drawdown as if made at and as of such date; and (iii) shall be true and accurate in
all material respects as of each other Drawdown Date as if made at and as of such date (except to the extent that any such representation and warranty speaks expressly as of an earlier date, in which case such representation and warranty shall be
true and accurate as of such earlier date). If any such representation or warranty shall not be so true and accurate in any respect or in any material respect, as applicable, prior to or as of the applicable Drawdown Date, Northshore shall give
written notice of such fact to Kenmare, specifying which representations and warranties are not so true and accurate and the reasons therefor. 

  
 7 

 7. Representations and Warranties of Kenmare. Kenmare hereby represents and warrants
to Northshore as of the date hereof and as of each Drawdown Date, that: 
 (a) (i) It is duly organized, validly existing and in
good standing under the laws of its jurisdiction of organization or incorporation. (ii) It has the requisite corporate, limited liability company, partnership or other power and authority to enter into this Agreement and the Shareholders’
Agreement and to perform its obligations hereunder and thereunder. The execution and delivery of each of this Agreement and the Shareholders’ Agreement and the performance and consummation of the transactions to which Kenmare is a party
contemplated hereby and thereby have been duly authorized by all requisite corporate, limited liability company, partnership or other action on the part of Kenmare and no other corporate, limited liability company or other proceedings on the part of
Kenmare are necessary to authorize the execution and delivery of this Agreement and the Shareholders’ Agreement or to consummate and perform the transactions to which Kenmare is a party contemplated hereby and thereby. Each of this Agreement
and the Shareholders’ Agreement has been duly executed and delivered by Kenmare and, assuming due authorization, execution and delivery of each such agreement by Northshore and Trident (as appropriate), constitutes a valid and binding agreement
of Kenmare enforceable against Kenmare in accordance with its terms, except to the extent that such enforcement may be subject to (x) applicable bankruptcy, insolvency, fraudulent conveyance, reorganization, moratorium and other similar laws
relating to or affecting creditors’ rights generally and (y) general equitable principles (whether considered in a proceeding in equity or at law). (iii) The execution and delivery by Kenmare of this Agreement and the
Shareholders’ Agreement does not, and the consummation by Kenmare of the transactions to which it is a party contemplated hereby and thereby and compliance by Kenmare with any of the provisions hereof and thereof will not conflict with or
result in any violation or breach of, or default (with or without notice or lapse of time, or both) under, (x) its organizational documents; (y) any material agreement to which Kenmare or any of its subsidiaries is a party or any of its or
their respective properties or assets is subject; or (z) any law, rule, regulation or order applicable to Kenmare or any of its subsidiaries, in any manner that would prevent Kenmare from entering into this Agreement or the Shareholders’
Agreement or from consummating the transactions contemplated hereby and thereby. (iv) No material consent, approval, order or authorization of, or registration, qualification, designation, declaration or filing with any governmental authority
on the part of Kenmare is required in connection with the performance and consummation of the transactions contemplated by this Agreement, except any consent, approval, order or authorization of, or registration, qualification, designation,
declaration or filing that has been previously obtained or made and is in effect or that may be properly obtained or made after the date hereof. 
 (b) Kenmare has, or its Affiliates have, such knowledge, sophistication and experience in financial and business matters that Kenmare is capable of evaluating the nature and merits of, and risks
attending, investments in Common Shares, and has, to the extent Kenmare believes such discussion necessary, discussed with professional legal, tax and financial advisers the suitability of an investment in Common Shares, and has determined that an
investment in Common Shares is consistent with Kenmare’s investment objectives. Kenmare 

  
 8 

 
understands and acknowledges that Northshore has a very limited financial and operating history. Kenmare is aware that an investment in Northshore is highly speculative and subject to substantial
risks. Kenmare is capable of bearing the high degree of economic risk and burdens of this investment, including, but not limited to, the possibility of a complete loss of Kenmare’s investment in Common Shares and the lack of a public market and
limited transferability of Common Shares, which may make the liquidation of this investment impossible for an indefinite period of time. 
 (c) Kenmare is not acquiring, or committing to acquire, Common Shares based upon any representation, oral or written, by any Person with respect to Northshore, other than those contained in this
Agreement, the Investors Agreement and the Shareholders’ Agreement, but rather upon an independent examination and judgment as to the prospects of Northshore. The Common Shares are being acquired solely for Kenmare’s own account, for
investment, and are not being purchased with a view to or for the resale, distribution, subdivision or fractionalization thereof; Kenmare has not entered into, and has no plans to enter into, any such contract, undertaking, agreement or arrangement;
and, except as may be set forth in the Shareholders’ Agreement, Kenmare has not entered into, and has no plans to enter into, any agreement to compel disposition of Common Shares. 

8. Headings; Counterparts. The Paragraph headings contained in this Agreement are for reference purposes only and shall not be
deemed a part of this Agreement or affect in any way the meaning or interpretation of this Agreement. This Agreement may be executed in any number of counterparts, all of which will be one and the same agreement. 

9. Entire Agreement. This Agreement, together with the Investors Agreement and the Exhibits thereto, constitutes the entire
agreement, and supersedes all prior agreements, understandings and statements, both written and oral, among the parties or any of their Affiliates with respect to the subject matter contained herein. 

10. Severability. The provisions of this Agreement are severable and the invalidity or unenforceability of any provision will not
affect the validity or enforceability of the other provisions of this Agreement. If any provision of this Agreement, or the application of that provision to any Person or any circumstance, is invalid or unenforceable, (a) a suitable and
equitable provision will be substituted for that provision in order to carry out, so far as may be valid and enforceable, the intent and purpose of the invalid or unenforceable provision and (b) the remainder of this Agreement and the
application of that provision to any Person or circumstance will not be affected by such invalidity or unenforceability, nor will such invalidity or unenforceability affect the validity or enforceability of that provision, or the application of that
provision, in any other jurisdiction. 

  
 9 

 11. Governing Law; Waiver of Jury Trial. 

(a) THIS AGREEMENT AND ALL CLAIMS OR CAUSES OF ACTION (WHETHER AT LAW, IN CONTRACT, IN TORT OR OTHERWISE) THAT MAY BE BASED UPON,
ARISING OUT OF OR RELATING TO THIS AGREEMENT OR ANY OF THE TRANSACTIONS CONTEMPLATED BY THIS AGREEMENT, OR THE NEGOTIATION, EXECUTION OR PERFORMANCE HEREOF, SHALL BE DEEMED TO BE MADE IN AND IN ALL RESPECTS SHALL BE INTERPRETED, CONSTRUED AND
GOVERNED BY AND IN ACCORDANCE WITH THE LAW OF THE STATE OF NEW YORK WITHOUT REGARD TO THE CONFLICTS OF LAW PRINCIPLES THEREOF. The parties hereby irrevocably submit to the personal jurisdiction of the courts of the State of New York and the United
States District Court for the Southern District of New York (the “Chosen Courts”) solely in respect of the interpretation and enforcement of the provisions of this Agreement and of the documents referred to in this Agreement, and in
respect of the transactions contemplated hereby, or the negotiation, execution or performance hereof, and hereby waive, and agree not to assert, as a defense in any action, suit or proceeding for the interpretation or enforcement hereof or of any
such document, that it is not subject thereto or that such action, suit or proceeding may not be brought or is not maintainable in the Chosen Courts or that the Chosen Courts are an inconvenient forum or that the venue thereof may not be
appropriate, or that this Agreement or any such document may not be enforced in or by such Chosen Courts, and the parties hereto irrevocably agree that all claims, actions, suits and proceedings or other causes of action (whether at law, in
contract, in tort or otherwise) that may be based upon, arising out of or relating to this Agreement or any of the transactions contemplated by this Agreement, or the negotiation, execution or performance hereof shall be heard and determined
exclusively in the Chosen Courts. The parties hereby consent to and grant any such Chosen Court jurisdiction over the person of such parties and, to the extent permitted by law, over the subject matter of such dispute and agree that mailing of
process or other papers in connection with any such action, suit or proceeding to the address set forth in Paragraph 14 shall be valid, effective and sufficient service thereof. 

(b) EACH PARTY ACKNOWLEDGES AND AGREES THAT ANY CONTROVERSY THAT MAY ARISE UNDER 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 IN RESPECT OF ANY ACTION, SUIT OR PROCEEDING DIRECTLY OR INDIRECTLY ARISING OUT OF OR RELATING TO THIS
AGREEMENT, OR THE TRANSACTIONS CONTEMPLATED BY THIS AGREEMENT. EACH PARTY CERTIFIES AND ACKNOWLEDGES THAT (i) NO REPRESENTATIVE, AGENT OR ATTORNEY OF ANY OTHER PARTY HAS REPRESENTED, EXPRESSLY OR OTHERWISE, THAT SUCH OTHER PARTY WOULD NOT, IN
THE EVENT OF SUCH ACTION, SUIT OR PROCEEDING, SEEK TO ENFORCE THE FOREGOING WAIVER, (ii) EACH PARTY UNDERSTANDS AND HAS CONSIDERED THE IMPLICATIONS OF THIS WAIVER, (iii) EACH PARTY MAKES THIS WAIVER VOLUNTARILY, AND (iv) EACH PARTY
HAS BEEN INDUCED TO ENTER INTO THIS AGREEMENT BY, AMONG OTHER THINGS, THE MUTUAL WAIVERS AND CERTIFICATIONS IN THIS PARAGRAPH 11. 

  
 10 

 12. No Third Party Beneficiaries. This Agreement shall be binding upon and inure
solely to the benefit of the parties hereto, Trident and their respective successors and permitted assigns and nothing herein, express or implied, is intended to or shall confer upon any Person other than Northshore, Kenmare, Trident and their
respective successors and permitted assigns, any legal or equitable right, benefit or remedy of any nature whatsoever under or by reason of this Agreement. 
 13. Amendments and Waivers. This Agreement may be amended or modified and the provisions hereof may be waived, only by an agreement in writing signed by each of Northshore and Kenmare and with the
prior written consent of Trident. No waiver by any of the parties of any default, misrepresentation or breach of warranty or covenant hereunder, whether intentional or not, shall be deemed to extend to any prior or subsequent default,
misrepresentation or breach of warranty or covenant hereunder or affect in any way any rights arising by virtue of any prior or subsequent such occurrence. No waiver by any of the parties of any of the provisions hereof shall be effective unless
explicitly set forth in writing and executed by the party sought to be charged with such waiver. 
 14. Notice. All
notices or other communications required or permitted to be given hereunder shall be in writing and shall be delivered by hand or sent by facsimile or other electronic delivery or sent, postage prepaid, by registered, certified or express mail or
overnight courier service, as follows: 
 if to Northshore: 

c/o Enstar Group Limited 
 Windsor Place, 3rd Floor 
 22 Queen Street 

Hamilton, Bermuda HM JX 
 Attn: Richard J. Harris 
 Facsimile: 441-296-7319 

if to Kenmare: 

c/o Enstar Group Limited 
 Windsor Place, 3rd Floor 
 22 Queen Street 

Hamilton, Bermuda HM JX 
 Attn: Richard J. Harris 
 Facsimile: 441-296-7319 

  
 11 

 All such notices, requests and other communications shall be deemed received on the date of receipt by the
recipient thereof if received prior to 5:00 p.m. in the place of receipt and such day is a Business Day. Otherwise, any such notice, request or communication shall be deemed not to have been received until the next succeeding Business Day.

 [Signature page follows] 

  
 12 

			
	Very truly yours,
	  
 KENMARE HOLDINGS LTD.

		
	By:	 	/s/ Richard J. Harris
		 	Name: Richard J. Harris
		 	Title:   Director

  

			
	Accepted and acknowledged:
	  
 NORTHSHORE HOLDINGS
LIMITED

		
	By:	 	/s/ Richard J. Harris
		 	Name: Richard J. Harris
		 	Title:   Director

 Schedule A 

 

									
	 Trident
	  	 Pro Rata Percentage
	 	  	 Total Subscription

Commitment1

	 
	 Trident V, L.P.
	  	 	22.92017%	  	  	 	$61,105,175.35	  
	 Trident V Parallel Fund, L.P.
	  	 	16.07422%	  	  	 	$42,853,869.45	  
	 Trident V Professionals Fund, L.P.
	  	 	1.00561%	  	  	 	$2,680,955.19	  
	 TOTAL
	  	 	40.00000%	  	  	 	$106,640,000.00	  
		  	  
	  
	 	  	  
	  
	 
			
	 
Kenmare
	  	 
Pro Rata Percentage
	 	  	 Total Subscription
Commitment
	 
	 Kenmare Holdings Ltd
	  	 	60.00000%	  	  	 	$159,960,000.00	  

  

	1 	The Total Subscription Amount will equal the pro rata percentage of the aggregate of the Atrium ($183.0 million) and Arden Re ($79.9 million) purchase prices, with no
reduction for debt, plus transaction expenses (estimated at $4.0 million).

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