Document:

EX-10.1

 Exhibit 10.1 
 ENSTAR GROUP LIMITED 
 EMPLOYEE SHARE PURCHASE PLAN 

(As Amended and Restated Effective September 1, 2014) 
 ARTICLE 1 - PURPOSE 
 The Enstar Group Limited Employee Share Purchase Plan
is intended to provide a method whereby Employees of Enstar Group Limited (the “Company”) will have an opportunity to acquire a proprietary interest in the Company through the purchase of ordinary shares of the Company
(“Shares”). It is the intention of the Company to have the Plan qualify as an “employee stock purchase plan” under Section 423 of the United States Internal Revenue Code of 1986, as amended (the “Code”) with
respect to Participants in the Plan who are United States taxpayers. The Plan was initially adopted by the Company’s Board of Directors on February 26, 2008, and approved by the Company’s shareholders on June 11, 2008.

 ARTICLE 2 - DEFINITIONS 
 2.1 “Administrator” shall mean the person or committee appointed by the Company to administer the Plan in accordance with Article 7. 

2.2 “Base Pay” shall mean regular straight-time earnings and shall exclude all other forms of compensation. 

2.3 “Employee” shall mean any regular employee of the Company or a subsidiary (within the meaning of Code
Section 424(f)) of the Company whose employees have been designated by the Administrator as eligible to participate in the Plan. 
 2.4 “Enrollment Period” shall mean the period prior to the beginning of an Offering Period during which an Employee may enroll in the Plan. The Administrator, in its discretion, may
establish one or more special Enrollment Periods during an Offering Period for newly-hired Employees. 
 2.5 “Fair
Market Value” shall mean, as of any date with respect to a Share, the closing price of a Share as reported on the NASDAQ Global Select Market or such other securities exchange on which such Shares may be primarily traded in the future.

 2.6 “Offering Period” shall mean the annual offering of the Company’s Shares which shall be the period
beginning each January 1 and ending the following December 31. 
 2.7 “Plan” shall mean the Enstar
Group Limited Employee Share Purchase Plan, as from time to time amended, as set forth herein and as amended from time to time. 

2.8 “Purchase Date” shall mean the last business day of each calendar month during each Offering Period. 

  
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 2.9 “Purchase Price” shall mean 85% of the Fair Market Value of a Share on
the Purchase Date. 
 ARTICLE 3 - ELIGIBILITY AND PARTICIPATION 
 3.1 Initial Eligibility. Any individual who becomes an Employee of the Company shall be eligible to participate in the Plan with respect to Offering Periods which commence after such
Employee’s hire date, provided the Employee makes an election to participate during the Enrollment Period for such Offering Period. The Administrator, in its sole discretion, may allow newly-hired Employees to participate in the Plan during the
Offering Period in which they are hired. Notwithstanding the foregoing, any highly compensated employee of the Company (within the meaning of Code Section 414(q)) who is subject to the reporting requirements of section 16(a) of the Securities
Exchange Act of 1934 with respect to the Company shall not be eligible to participate in the Plan. 
 3.2 Commencement of
Participation. An Employee may become a “Participant” in the Plan by authorizing the Company to make payroll deductions in the form and manner specified by the Administrator during the Enrollment Period for an Offering Period, in
accordance with Article 4. 
 3.3 Restrictions on Participation. Notwithstanding any provision of the Plan to the
contrary, no Employee shall be granted the right to participate in the Plan, if: 
  

	 	(a)	immediately after the such right is granted, such Employee would own stock, and/or hold outstanding options to purchase stock, possessing 5% or more of the total
combined voting power or value of all classes of stock of the Company (for purposes of this paragraph, the rules of Section 424(d) of the Code shall apply in determining stock ownership of any Employee); 

 

	 	(b)	such grant would permit his or her rights to purchase Shares in any calendar year under all employee stock purchase plans of the Company to accrue at a rate which
exceeds $25,000 in Fair Market Value of the Shares (determined at the time such right is granted); or 

  

	 	(c)	such grant would permit the Employee to purchase during an Offering Period a number of Shares that exceeds the number of Shares determined by dividing $25,000 by the
Fair Market Value of a Share on the first day of the Offering Period. 

 ARTICLE 4 - PAYROLL DEDUCTIONS 

4.1 Amount of Deduction. An Employee may participate in the Plan by authorizing up to 15%, or such other percentage determined by
the Administrator with respect to an Offering Period, to be deducted from his or her Base Pay during each payroll period in the Offering Period and used to purchase Shares under the Plan. Such payroll authorization shall be made in accordance with
rules established by the Administrator. All payroll authorizations shall be made in whole percentages, and deductions shall be rounded to the nearest dollar. 

  
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 4.2 Participant’s Account. All payroll deductions made on behalf of a
Participant shall be credited to an account established in the Participant’s name under the Plan. A Participant may not make any separate cash payment into such account or make any withdrawals from such account. 

4.3 Changes in Payroll Deductions. A Participant may discontinue participation in the Plan during any Offering Period by
withdrawing his or her payroll authorization, but no other change can be made during an Offering Period. A Participant may not alter the amount of his or her payroll deductions for an Offering Period, except to zero. 

ARTICLE 5 - PURCHASE OF SHARES 
 5.1 Monthly Purchase Dates. As of the last business day of each month during the Offering Period, the accumulated payroll deductions in the Participant’s account will be used to purchase
Shares. The number of Shares to be purchased will be equal to the dollar amount in the Participant’s account divided by the Purchase Price. No fractional Shares will be purchased. Any amount remaining in the Participant’s account after the
Purchase Date will be used to purchase Shares on the next Purchase Date in the Offering Period. Any amount remaining in the Participant’s account at the end of the Offering Period will be returned to the Participant. 

5.2 Effect of Termination of Employment. Upon termination of the Participant’s employment, the payroll deductions credited to
the Participant’s account will be applied to the purchase of Shares as of the next Purchase Date. Any amount remaining in the Participant’s account after such Purchase Date will be returned to the Participant (or his or her estate, in the
case of death). 
 5.3 Interest. No interest will be paid or allowed on any money paid into the Plan or credited to the
account of any Participant. 
 5.4 Currency Conversion. In the event a Participant’s Base Pay is not payable in
United States dollars, then the payroll deductions in the Participant’s account shall be converted to United States dollars at the spot exchange rate at the close of business on the Purchase Date, in accordance with procedures established by
the Administrator. 
 ARTICLE 6 - SHARES 
 6.1 Maximum Shares. The maximum number of Shares which shall be issued under the Plan shall be 200,000 Shares. Such Shares may be either authorized and unissued Shares or issued Shares reacquired
by the Company and held as Treasury Shares, as the Administrator may from time to time determine. In the event that there is an increase or decrease in the number of issued Shares by reason of any cause such as a stock split, reorganization,
recapitalization, combination or exchange of shares, merger, consolidation, or any other change in corporate structure without receipt or payment of consideration by the Company, the number of Shares then remaining for issue under the Plan shall in
each such event be adjusted by the Administrator in proportion to the change in issued Shares resulting from such cause. 
 6.2
Participant’s Interest in Shares. As promptly as practicable after each Purchase Date, the Company will transfer the acquired Shares to the Participant or will hold the Shares in 

  
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account in uncertified form, as appropriate. A Participant will have no ownership interest in Shares covered by his or her payroll deductions until such deductions are used to acquire Shares and
the Shares are registered in the Participant’s name. 
 ARTICLE 7 - ADMINISTRATION 

7.1 Appointment of Administrator. The Board of Directors may appoint an Administrator to administer the Plan, which may be an
individual or committee, as determined by the Board. In the event that an Administrator has not been appointed, the Board of Directors shall act as the Administrator. 
 7.2 Authority of Administrator. Subject to the express provisions of the Plan, the Administrator shall have the discretionary authority to interpret and construe any and all provisions of the Plan,
to adopt rules and regulations for administering the Plan, and to make all other determinations deemed necessary or advisable for administering the Plan. The Administrator’s determination on the foregoing matters shall be conclusive, final and
binding on all parties. 
 ARTICLE 8 - MISCELLANEOUS 
 8.1 Transferability. Neither payroll deductions credited to a Participant’s account nor any rights to acquire Shares under the Plan may be assigned, transferred, pledged, or otherwise disposed
of in any way by the Participant other than by will or the laws of descent and distribution. Any such attempted assignment, transfer, pledge or other disposition shall be without effect. 

8.2 Use of Funds. All payroll deductions received or held by the Company under this Plan may be used by the Company for any
corporate purpose and the Company shall not be obligated to segregate such payroll deductions. 
 8.3 Amendment and
Termination. The Board of Directors shall have complete power and authority to terminate or amend the Plan; provided, however, that the Board of Directors shall not, without the approval of the shareholders of the Company (i) increase the
maximum number of shares which may be issued under the Plan, except pursuant to Section 6.1, or (ii) amend the Plan to change the designation of corporations whose employees may participate in the Plan. 

8.4 No Employment Rights. The Plan does not, directly or indirectly, create in any Employee or class of Employees any right with
respect to continuation of employment by the Company, and it shall not be deemed to interfere in any way with the Company’s right to terminate, or otherwise modify, an Employee’s employment at any time. 

8.5 Effect of Plan. The provisions of the Plan shall, in accordance with its terms, be binding upon and inure to the benefit of
all successors of each Employee participating in the Plan, including, without limitations, such Employee’s estate and the executors, administrators or trustees thereof, heirs and legatees, and any receiver, trustee in bankruptcy or
representative of credits of such Employee. 

  
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 8.6 Governing Law. The law of the State of Delaware will govern all matters relating
to this Plan except to the extent it is superseded by the laws of the United States. 

  
 5EX-10.3

 Exhibit 10.3 
 Enstar Group Limited 
 P.O. HM Box 2267, Windsor Place,
3rd Floor 

22 Queen Street 

Hamilton, HM JX 

Bermuda 
 August 11, 2014

 Attn: Dominic F. Silvester, Chief Executive Officer 
 Re: Extension of Employment Agreement Term 
 Dear Dominic, 

In recognition of your continued valuable service to Enstar Group Limited, we wish to amend your Amended and Restated Employment
Agreement, originally dated May 1, 2007 (as amended), which is attached as Exhibit A, and further amended by way of letter agreement dated April 19, 2012, which is attached as Appendix 1 (collectively, your “Employment
Agreement”). We wish to extend the Term of the Employment Agreement (as defined in the Employment Agreement) for an additional term of one year. The modified Term shall be six years commencing on January 1, 2012, as further extended or
unless sooner terminated in accordance with the other provisions of the Employment Agreement. For purposes of Section A of Exhibit A to your Employment Agreement, “the fifth anniversary of the date hereof” shall now read “December 31,
2017”. 
 If you agree to this extension of the Term of your Employment Agreement, please sign the letter in the space
provided below and return it to me. 
  

	
	 Sincerely,

	
	Enstar Group Limited
	
	 /s/ Richard J. Harris

	 Richard J. Harris, Chief Financial Officer

 Accepted and agreed to 
 this 11th day of August 2014 
 /s/ Dominic F. Silvester 

Dominic F. Silvester 

 Appendix 1 – 2012 Letter Agreement 

 Enstar Group Limited 

P.O. HM Box 2267, Windsor Place, 3rd Floor 
 18 Queen Street 
 Hamilton, HM JX 

Bermuda 
 April 19, 2012

 Attn: Dominic F. Silvester, Chief Executive Officer 
 Re: Extension of Employment Agreement Term 
 Dear Dominic, 

In recognition of your valuable service to Enstar Group Limited over the past few years, we wish to amend your Amended and Restated
Employment Agreement, dated May 1, 2007, as amended, which is attached as Exhibit A, to extend its Term (as defined in the Employment Agreement) for an additional term of five years. The modified Term shall be five years commencing on
January 1, 2012, as further extended or unless sooner terminated in accordance with the other provisions of the Employment Agreement. For purposes of Section A of Exhibit A to your Employment Agreement, “the fifth anniversary of the date
hereof” shall now read “December 31, 2016”. 
 If you agree to this extension of the Term of your Employment
Agreement, please sign the letter in the space provided below and return it to me. 
  

	
	 Sincerely,

	
	Enstar Group Limited
	
	 /s/ Richard J. Harris

	 Richard J. Harris, Chief Financial Officer

 Accepted and agreed to 
 this 19th day
of April 2012 
 /s/ Dominic F. Silvester 
 Dominic F. Silvester 
  

 Exhibit A – Existing Employment Agreement 

 AMENDED AND RESTATED EMPLOYMENT AGREEMENT 

This AMENDED AND RESTATED EMPLOYMENT AGREEMENT (“Agreement”) is dated as of May 1, 2007, between Enstar Group Limited
(formerly known as Castlewood Holdings Limited), a Bermuda corporation (“Company”), and Dominic F. Silvester (“Executive”). 
 BACKGROUND 
 Company desires to employ Executive, and Executive
desires to be an employee of Company, on the terms and conditions contained in this Agreement. 
 NOW, THEREFORE, in
consideration of the premises and the mutual agreements contained herein and intending to be legally bound hereby, the parties hereto agree as follows: 
 TERMS 
 1. CAPACITY AND DUTIES 

1.1 Employment; Acceptance of Employment. Company hereby employs Executive and Executive hereby agrees to continue
employment by Company for the period and upon the terms and conditions hereinafter set forth. Effective on the date hereof, this Agreement amends and restates the Employment Agreement between Company and Executive, dated as of May 1, 2007 in
its entirety, and the rights and obligations of each party shall be governed by this Agreement. 
 1.2 Capacity and
Duties. 
 (a) Executive shall serve as Chief Executive Officer of Company. Executive shall perform such duties and
shall have such authority consistent with his position as may from time to time be specified by the Board of Directors of Company. Executive shall report directly to the Board of Directors of Company and his principal place of business shall be
Company’s office in Bermuda and his secondary places of business may be in continental Europe. It is recognised that extensive travel may be necessary or appropriate in connection with the performance of Executive’s duties hereunder.

 (b) Executive shall devote his full working time and energy, skill and best efforts to the performance of his duties
hereunder, in a manner that will comply with Company’s rules and policies and will faithfully and diligently further the business and interests of Company. Executive shall not be employed by or participate or engage in or in any manner be a
part of the management or operation of any business enterprise other than Company without the prior written consent of Company, which consent may be 

 
granted or withheld in the reasonable discretion of the Board of Directors of Company. Notwithstanding anything herein to the contrary, nothing shall preclude Executive from (i) serving on
the boards of directors of a reasonable number of other corporations or the boards of a reasonable number of trade associations and/or charitable organizations, (ii) engaging in charitable, community and other business affairs, and
(iii) managing his personal investments and affairs, provided that such activities do not materially interfere with the proper performance of his responsibilities and duties hereunder. 
 2. TERM OF EMPLOYMENT 
 2.1 Term. The term of Executive’s
employment hereunder shall be five years commencing on the date hereof, as further extended or unless sooner terminated in accordance with the other provisions hereof (the “Term”). Except as hereinafter provided, on the fifth anniversary
of the commencement date and on each subsequent anniversary thereof, the Term shall be automatically extended for one year unless either party shall have given to the other party written notice of termination of this Agreement at least 120 days
prior to such anniversary. If written notice of termination is given as provided above, Executive’s employment under this Agreement shall terminate on the last day of the Term. 

 

	3.	COMPENSATION 

 3.1 Basic
Compensation. As compensation for Executive’s services during the first twelve months of the Term, Company shall pay to Executive a salary at the annual rate of $600,000 payable in periodic installments in accordance with Company’s
regular payroll practices in effect from time to time. For each subsequent twelve-month period of Executive’s employment hereunder, Executive’s salary shall be in the amount of his initial annual salary with such increases, as may be
established by the Board of Directors of Company in consultation with Executive provided that the increase in base salary with respect to each subsequent twelve-month period shall not be less than the product of Executive’s base salary
multiplied by the annual percentage increase in the retail price index (expressed as a decimal) for the United States, as reported in the most recent report of the U.S. Department of Labor for the preceding twelve-month period. Once increased,
Executive’s annual salary cannot be decreased without the written consent of Executive. Executive’s annual salary, as determined in accordance with this Section 3.1, is hereinafter referred to as his “Base Salary.”

 3.2 Performance Bonus. Executive shall, following the completion of each fiscal year of Company during the
Term, be eligible for a performance bonus in accordance with Company’s performance bonus plan. Executive shall also be eligible for additional equity and other incentive awards, at a level commensurate with his position and in accordance with
the policies and practices of the Company. 
 3.3 Employee Benefits. During the Term, Executive shall be entitled
to participate in such of Company’s employee benefit plans and benefit programs, as may 

  
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from time to time be provided by Company. In addition, during the Term, Executive shall be entitled to the following: 
 (a) a housing allowance equal to $8,500 per month; 
 (b) a life insurance policy
in the amount of five times the Executive’s Base Salary, provided that Executive assists Company in the procurement of such policy (including, without limitation, submitting to any required physical examinations and completing accurately any
applicable applications and or questionnaires); 
 (c) fully comprehensive medical and dental coverage on a worldwide basis for
the Executive, his spouse and dependents and an annual medical examination for same; 
 (d) long term disability coverage,
including coverage for serious illness, and full compensation paid by Company during the period up to and until Executive begins receiving benefits under such long term disability plan. In the event that the generally applicable group long-term
disability plan contains a limitation on benefits that would result in Executive’s being entitled to benefit payments under such plan which are less than 50% of his salary, Company shall provide Executive with an individual disability policy
paying a benefit amount that, when coupled with the group policy benefit payable, would provide Executive with aggregate benefits in connection with his long-term disability equal to 50% of such salary (provided that, if an individual policy can not
be obtained for such amount on commercially reasonable rates and on commercially reasonable terms, Company shall provide Executive with a policy providing for the greatest amount of individual coverage that is available on such standard terms and
rates). Provision of any individual disability policy will also be contingent upon Executive being able to be insured at commercially reasonable rates and on commercially reasonable terms and upon Executive assisting Company in the procurement of
such policy (including, without limitation, submitting to any required physical examinations and completing accurately any applicable applications and or questionnaires); 
 (e) payment from the company of an amount equal to 10% of Executive’s Base Salary each year to Executive as contribution to his pension plans; and 

(f) During the Term, Executive will be reimbursed for one return trip for his family to/from Bermuda each calendar year. Executive’s
wife may travel business class and his children may travel premium economy class. 
 3.4 Vacation. During the
Term, Executive shall be entitled to a paid vacation of 30 days per year (including 30 days during 2007). 
 3.5 Expense
Reimbursement. Company shall reimburse Executive for all reasonable out-of-pocket expenses incurred by him in connection with the performance of his duties hereunder in accordance with its regular reimbursement policies as in effect from
time to time. 

  
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 4. TERMINATION OF EMPLOYMENT 
 4.1 Death of Executive. If Executive dies during the Term, and for the year in which Executive dies, Company achieves the performance goals established in accordance with any incentive plan
in which Executive participates, Company shall pay Executive’s estate an amount equal to the bonus that Executive would have received had he been employed by Company for the full year, multiplied by a fraction, the numerator of which is the
number of calendar days Executive was employed in such year and the denominator of which is 365. In addition, Executive’s spouse and dependents (if any) shall be entitled for a period of 36 months, to continue to receive medical benefits
coverage (as described in Section 3.3) at Company’s expense if and to the extent Company was paying for such benefits for Executive’s spouse and dependents at the time of Executive’s death. 

4.2 Disability. If Executive is or has been materially unable for any reason to perform his duties hereunder for 120 days
during any period of 150 consecutive days, Company shall have the right to terminate Executive’s employment upon 30 days’ prior written notice to Executive at any time during the continuation of such inability, in which event Company shall
thereafter be obligated to continue to pay Executive’s Base Salary for a period of 36 months, periodically in accordance with Company’s regular payroll practices and, within 30 days of such notice, shall pay any other amounts (including
salary, bonuses, expense reimbursement, etc.) that have been fully earned by, but not yet paid to, Executive under this Agreement as of the date of such termination. The amount of payments to Executive under disability insurance policies paid for by
Company shall be credited against and shall reduce the Base Salary otherwise payable by Company following termination of employment. If, for the year in which Executive’s employment is terminated pursuant to this Section, Company achieves the
performance goals established in accordance with any incentive plan in which Executive participates, Company shall pay Executive an amount equal to the bonus that Executive would have received had he been employed by Company for the full year,
multiplied by a fraction, the numerator of which is the number of calendar days Executive was employed in such year and the denominator of which is 365. Executive shall be entitled for a period of 36 months, to continue to receive at Company’s
expense medical benefits coverage (as described in Section 3.3) for Executive and Executive’s spouse and dependents (if any) if and to the extent Company was paying for such benefits to Executive and Executive’s spouse and dependents
at the time of such termination. 
 4.3 Termination for Cause. Executive’s employment hereunder shall
terminate immediately upon notice that the Board of Directors of Company is terminating Executive for Cause (as defined herein), in which event Company shall not thereafter be obligated to make any further payments hereunder other than amounts
(including salary, expense reimbursement, etc.) that have been fully earned by, but not yet paid to, Executive under this Agreement as of the date of such termination. “Cause” shall mean (a) fraud or dishonesty in connection with
Executive’s employment that results in a 

  
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material injury to Company, (b) conviction of any felony or crime involving fraud or misrepresentation or (c) after Executive has received written notice of the specific material and
continuing failure of Executive to perform his duties hereunder (other than death or disability) and has failed to cure such failure within 30 days of receipt of the notice, or (d) material and continuing failure to follow reasonable
instructions of the Board of Directors after Executive has received at least prior written notice of the specific material and continuing failure to follow instructions and has failed to cure such failure within 30 days of receipt of the notice.

 4.4 Termination without Cause or for Good Reason. 

(a) If (1) Executive’s employment is terminated by Company for any reason other than Cause or the death or disability of
Executive, or (2) Executive’s employment is terminated by Executive for Good Reason (as defined herein): 
 (i)
Company shall pay Executive any amounts (including salary, bonuses, expense reimbursement, etc.) that have been fully earned by, but not yet paid to, Executive under this Agreement as of the date of such termination; 

(ii) Company shall pay Executive a lump sum amount equal to three times the Base Salary payable to him; 

(iii) Executive shall be entitled to continue to receive medical benefits coverage (as described in Section 3.3) for Executive and
Executive’s spouse and dependents (if any) at Company’s expense for a period of 36 months; 
 (iv) Anything to the
contrary in any other agreement or document notwithstanding, each outstanding equity incentive award granted to Executive before, on or within three years after the date hereof shall become immediately vested and exercisable on the date of such
termination; and 
 (v) In addition, if, for the year in which Executive is terminated, Company achieves the performance goals
established in accordance with any incentive plan in which Executive participates, Company shall pay an amount equal to the bonus that Executive would have received had he been employed by Company for the full year. 

(b) Upon making the payments described in this Section 4.4, Company shall have no further obligation to Executive under this
Agreement. 
 (c) “Good Reason” shall mean the following: 

(i) material breach of Company’s obligations hereunder, provided that Executive shall have given written notice thereof to Company,
and Company shall have failed to remedy the circumstances within 30 days; 

  
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 (ii) the relocation of Executive’s principal business office outside of Bermuda
without the Executive’s prior agreement; or 
 (iii) any material reduction in Executive’s duties or authority.

 4.5 Change in Control. 
 (a) If, during the Term, there should be a Change of Control (as defined herein), and within 1 year thereafter either (i) Executive’s employment should be terminated for any reason other than
for Cause or (ii) Executive terminates his employment for Good Reason (as defined in Section 4.4): 
 (i) Company
shall pay Executive any amounts (including salary, bonuses, expense reimbursement, etc.) that have been fully earned by, but not yet paid to, Executive under this Agreement as of the date of such termination; 

(ii) Company shall pay Executive a lump sum amount equal to three times Executive’s then current Base Salary; 

(iii) Executive shall be entitled to continue to receive medical benefits coverage (as described in Section 3.3) for Executive and
Executive’s spouse and dependents (if any) at Company’s expense for a period of 36 months; 
 (iv) Anything to the
contrary in any other agreement or document notwithstanding, each outstanding equity incentive award granted to Executive before, on or after the date hereof shall become immediately vested and exercisable on the date of such termination; and

 (v) In addition, if, for the year in which Executive is terminated, Company achieves the performance goals established in
accordance with any incentive plan in which Executive participates, Company shall pay an amount equal to the bonus that Executive would have received had he been employed by Company for the full year. 

(b) Upon making the payments described in this Section 4.5, Company shall have no further obligation to Executive under this
Agreement. 
 (c) A “Change in Control” of Company shall mean: 

(i) the acquisition by any person, entity or “group” required to file a Schedule 13D or Schedule 14D-1 under the Securities
Exchange Act of 1934 (the “1934 Act”) (excluding, for this purpose, Company, its subsidiaries, any employee benefit plan of Company or its subsidiaries which acquires ownership of voting securities of Company, and any group that includes
Executive) of beneficial ownership (within the meaning of Rule 13d-3 under the 1934 Act) of 50% or more of either the then outstanding ordinary shares or the combined voting power of Company’s then outstanding voting securities entitled to vote
generally in the election of directors; 

  
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 (ii) the election or appointment to the Board of Directors of Company, or resignation of or
removal from the Board, of directors with the result that the individuals who as of the date hereof constituted the Board (the “Incumbent Board”) no longer constitute at least a majority of the Board, provided that any person who becomes a
director subsequent to the date hereof whose appointment, election, or nomination for election by Company’s shareholders, was approved by a vote of at least a majority of the Incumbent Board (other than an appointment, election or nomination of
an individual whose initial assumption of office is in connection with an actual or threatened election contest relating to the election of the directors of Company) shall be, for purposes of this Agreement, considered as though such person were a
member of the Incumbent Board; or 
 (iii) approval by the shareholders of Company of: (i) a reorganization, merger or
consolidation by reason of which persons who were the shareholders of Company immediately prior to such reorganization, merger or consolidation do not, immediately thereafter, own more than 50% of the combined voting power of the reorganized, merged
or consolidated company’s then outstanding voting securities entitled to vote generally in the election of directors, or (ii) a liquidation or dissolution of Company or the sale, transfer, lease or other disposition of all or substantially
all of the assets of Company (whether such assets are held directly or indirectly). 
 5. RESTRICTIVE COVENANTS 

5.1 Restrictive Covenants. 
 (a) Executive acknowledges that he is one of a small number of key executives and that in such capacity, he will have access to confidential information of the Company and will engage in key client
relationships on behalf of the Company and that it is fair and reasonable for protection of the legitimate interests of the Company and the other key executives of the Company that he should accept the restrictions described in Exhibit A hereto.

 (b) Promptly following Executive’s termination of employment, Executive shall return to the Company all property of the
Company, and all documents, accounts, letters and papers of every description relating to the affairs and business of the Company or any of its subsidiaries, and copies thereof in Executive’s possession or under his control. 

(c) Executive acknowledges and agrees that the covenants and obligations of Executive in Exhibit A and this Section 5.1 relate to
special, unique and extraordinary matters and that a violation of any of the terms of such covenants and obligations will cause the Company irreparable injury for which adequate remedies are not available at

  
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law. Therefore, Executive agrees that the Company shall be entitled to an injunction, restraining order or such other equitable relief (without the requirement to post bond) restraining Executive
from committing any violation of the covenants and obligations contained in Exhibit A and this Section 5.1. These injunctive remedies are cumulative and are in addition to any other rights and remedies the Company may have at law or in equity.

 (d) Executive agrees that if he applies for, or is offered employment by (or is to provide consultancy services to) any other
person, firm, company, business entity or other organization whatsoever (other than an affiliate of the Company) during the restriction periods set forth in Exhibit A, he shall promptly, and before entering into any contract with any such third
party, provide to such third party a full copy of Exhibit A and this Section 5.1 in order to ensure that such other party is fully aware of Executive’s obligations hereunder. 

5.2 Intellectual Property Rights. Executive recognizes and agrees that Executive’s duties for the Company may include
the preparation of materials, including written or graphic materials for the Company or its affiliate, and that any such materials conceived or written by Executive shall be done within the scope of his employment as a “work made for
hire.” Executive agrees that because any such work is a “work made for hire,” the Company (or the relevant affiliate of the Company) will solely retain and own all rights in said materials, including rights of copyright. Executive
agrees to disclose and assign to the Company his entire right, title and interest in and to all inventions and improvements related to the Company’s business or to the business of the Company’s affiliates (including, but not limited to,
all financial and sales information), whether patentable or not, whether made or conceived by him individually or jointly with others at any time during his employment by the Company hereunder. Such inventions and improvements are to become and
remain the property of the Company and Executive shall take such actions as are reasonably necessary to effectuate the foregoing. 
 6.
MISCELLANEOUS 
 6.1 Key Employee Insurance. Company shall have the right at its expense to purchase insurance on
the life of Executive, in such amounts as it shall from time to time determine, of which Company shall be the beneficiary. Executive shall submit to such physical examinations as may reasonably be required and shall otherwise cooperate with Company
in obtaining such insurance. 
 6.2 Indemnification/Litigation. Company shall indemnify and defend Executive
against all claims arising out of Executive’s activities as an officer or employee of Company or its affiliates to the fullest extent permitted by law and under Company’s organizational documents. At the request of Company, Executive shall
during and after the Term render reasonable assistance to Company in connection with any litigation or other proceeding involving Company or any of its affiliates. Company shall provide reasonable compensation to Executive for such assistance
rendered after the Term. 

  
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 6.3 No Mitigation. In no event shall Executive be required to seek other
employment or take any other action by way of mitigation of the amounts payable to Executive under this Agreement, and such amounts shall not be reduced whether or not Executive obtains other employment after termination of his employment hereunder.

 6.4 Severability. The invalidity or unenforceability of any particular provision or part of any provision of
this Agreement shall not affect the other provisions or parts hereof. 
 6.5 Assignment; Benefit. This Agreement
shall not be assignable by Executive, and shall be assignable by Company only with the Executive’s consent and only to any person or entity which may become a successor in interest (by purchase of assets or stock, or by merger, or otherwise) to
Company in the business or substantially all of the business presently operated by it. Any Change in Control is deemed an assignment. Subject to the foregoing, this Agreement and the rights and obligations set forth herein shall inure to the benefit
of, and be binding upon, the parties hereto and each of their respective permitted successors, assigns, heirs, executors and administrators. 
 6.6 Notices. All notices hereunder shall be in writing and shall be sufficiently given if hand-delivered, sent by documented overnight delivery service or registered or certified mail,
postage prepaid, return receipt requested or by facsimile, receipt acknowledged, addressed as set forth below or to such other person and/or at such other address as may be furnished in writing by any party hereto to the other. Any such notice shall
be deemed to have been given as of the date received, in the case of personal delivery, or on the date shown on the receipt or confirmation therefor, in all other cases. Any and all service of process and any other notice in any action, suit or
proceeding shall be effective against any party if given as provided in this Agreement; provided that nothing herein shall be deemed to affect the right of any party to serve process in any other manner permitted by law. 

 

			
	(a)	  	If to Company:
		
		  	 Enstar Group Limited
 P.O. Box
HM 2267
 Windsor Place, 3rd Floor
 18
Queen Street
 Hamilton HM JX

Bermuda

		
		  	 Attention: Paul O’Shea

Facsimile No.: 1 441 292 6603

  
 9 

			
	(b)	  	If to Executive:
		
		  	 Dominic F. Silvester
 Seaspray
5a
 Number 2 Palmetto Court
 Smiths FL
07
 Bermuda

 6.7 Entire Agreement; Modification; Advice of Counsel. 

(a) This Agreement constitutes the entire agreement between the parties hereto with respect to the matters contemplated herein and
supersedes all prior agreements and understandings with respect thereto. No addendum, amendment, modification, or waiver of this Agreement shall be effective unless in writing. Neither the failure nor any delay on the part of any party to exercise
any right or remedy hereunder shall operate as a waiver thereof, nor shall any single or partial exercise of any right or remedy preclude any other or further exercise of the same or of any other right or remedy with respect to such occurrence or
with respect to any other occurrence. 
 (b) Executive acknowledges that he has been afforded an opportunity to consult with his
counsel with respect to this Agreement. 
 6.8 Governing Law. This Agreement is made pursuant to, and shall be
construed and enforced in accordance with, the laws of Bermuda, to the extent applicable, without giving effect to otherwise applicable principles of conflicts of law. 
 6.9 Headings; Counterparts. The headings of paragraphs in this Agreement are for convenience only and shall not affect its interpretation. This Agreement may be executed in two or more
counterparts, each of which shall be deemed to be an original and all of which, when taken together, shall be deemed to constitute the same Agreement. 
 6.10 Further Assurances. Each of the parties hereto shall execute such further instruments and take such additional actions as the other party shall reasonably request in order to effectuate
the purposes of this Agreement. 
 [signature page follows] 

  
 10 

 IN WITNESS WHEREOF, the parties have executed this Agreement as of the date first above
written. 
  

			
	ENSTAR GROUP LIMITED
		
	 By:
	 	 /s/ RICHARD J. HARRIS

		 	 Name: Richard J. Harris

		 	 Title: Chief Financial Officer

	
	 /s/ DOMINIC SILVESTER

	     Dominic Silvester

  
 11 

 Exhibit A 

Restrictive Covenants 
  

	A.	Noncompetition. During the Term and, if Executive fails to remain employed through the fifth anniversary of the date hereof, for a period of eighteen
(18) months after Executive’s employment terminates (the “Restriction Period”), Executive shall not, without the prior written permission of the Board, directly or indirectly engage in any Competitive Activity. The term
“Competitive Activity” shall include (i) entering the employ of, or rendering services to, any person, firm or corporation engaged in the insurance and reinsurance run-off or any other business in which the Company or any of its
affiliates has been engaged at any time during the last twelve months of the Term and to which Executive has rendered services or about which Executive has acquired Confidential Information or by which Executive has been engaged at any time during
the last twelve months of his period of employment hereunder and in each case in any jurisdiction in which the Company or any of its affiliates has conducted substantial business (hereinafter defined as the “Business”); (ii) engaging
in the Business for Executive’s own account or (becoming interested in any such Business, directly or indirectly, as an individual, partner, shareholder, member, director, officer, principal, agent, employee, trustee, consultant, or in any
other similar capacity; provided, however, nothing in this Paragraph A shall prohibit Executive from owning, solely as a passive investment, 5% or less of the total outstanding securities of a publicly-held company, or any interest held by Executive
in a privately-held company as of the date of this Agreement; provided further that the provisions of this Paragraph A shall not apply in the event Executive’s employment with the Company is terminated without Cause or with Good Reason.

  

	B.	 Confidentiality. Without the prior written consent of the Company, except to the extent required by an order of a court having competent
jurisdiction or under subpoena from an appropriate regulatory authority, Executive shall not disclose and shall use his best endeavours to prevent the disclosure of any trade secrets, customer lists, market data, marketing plans, sales plans,
management organization information (including data and other information relating to members of the Board and management), operating policies or manuals, business plans or financial records, or other financial, commercial, business or technical
information relating to the Company or any of its subsidiaries or affiliates or information designated as confidential or proprietary that the Company or any of its subsidiaries or affiliates may receive belonging to clients or others who do
business with the Company or any of its subsidiaries or affiliates (collectively, “Confidential Information”) to any third person unless such Confidential Information has been previously disclosed to the public by the Company or any
of its subsidiaries or affiliates or is in the public domain (other than by reason of Executive’s breach of this Paragraph B). In the event that Executive is required to

  
 12 

	 	
disclose Confidential Information in a legal proceeding, Executive shall provide the Company with notice of such request as soon as reasonably practicable, so that the Company may timely seek an
appropriate protective order or waive compliance with this Paragraph B, except if such notice would be unlawful or would place Executive in breach of an undertaking he is required to give by law or regulation. 

 

	C.	Non-Solicitation of Employees. During the Restriction Period, Executive shall not, without the prior written permission of the Board, directly or indirectly
induce any Senior Employee of the Company or any of its affiliates to terminate employment with such entity, and shall not directly or indirectly, either individually or as owner, agent, employee, consultant or otherwise, offer employment to or
employ any Senior Employee unless such person shall have ceased to be employed by the Company or any affiliate for a period of at least six (6) months. For the purpose of this Paragraph C, “Senior Employee” shall mean a person
who, at any time during the last twelve months of Executive’s period of employment hereunder: 

 (i) is
engaged or employed (other than in a clerical, secretarial or administrative capacity) as an employee, director or consultant of the Company or its affiliates; and 
 (ii) is or was engaged in a capacity in which he obtained Confidential Information; and 
 (iii) had personal dealings with Executive. 
  

	D.	Non-Disparagement. Executive shall not do or say anything adverse or harmful to, or otherwise disparaging of, the Company or its subsidiaries and their
respective goodwill. The Company shall not, and shall use reasonable efforts to ensure that its officers, directors, employees and subsidiaries do not do or say anything adverse or harmful to, or otherwise disparaging of, Executive and his goodwill;
provided that no action by either party in connection with the enforcement of its rights hereunder shall be construed as a violation of this Paragraph D. 

 

	E.	Definition. In this Exhibit A, “directly or indirectly” (without prejudice to the generality of the expression) means whether as principal or agent
(either alone or jointly or in partnership with any other person, firm or company) or as a shareholder, member or holder of loan capital in any other company or being concerned or interested in any other person, firm or company and whether as a
director, partner, consultant, employee or otherwise. 

  

	F.	Severability. Each of the provisions contained in this Exhibit A is and shall be construed as separate and severable and if one or more of such provisions is
held to be against the public interest or unlawful or in any way an unreasonable restraint of trade or unenforceable in whole or in part for any reason, the remaining provisions of this Exhibit A or part thereof, as appropriate, shall continue to be
in full force and effect. 

  
 13 

 May 4, 2011 
 Enstar Group Limited 
 P.O. Box 2267, Windsor Place, 3rd Floor 
 18 Queen Street 
 Hamilton, HM JX 
 Bermuda 
 Attn: Richard J. Harris 

Re: Waiver of Housing Allowance under Employment Agreement 
 Dear Richard, 
 Effective January 1, 2011, I hereby waive my right to a
housing allowance under my Amended and Restated Employment Agreement with Enstar Group Limited, dated May 1, 2007, in consideration of the Compensation Committee’s decision to increase my annual base salary by an amount equal to the annual
amount of the housing allowance. 
  

	
	 Sincerely,

	
	 /s/ Dominic F. Silvester

	Dominic F. Silvester

 Accepted and agreed to 
 this 4th day of May, 2011 
  

			
	ENSTAR GROUP LIMITED
		
	 By:
	 	 /s/ Richard J. Harris

	 Name: Richard J. Harris

	 Title: Chief Financial Officer

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