Document:

EX-10.73

 Exhibit 10.73 
 2013 PROGRESSIVE CAPITAL 
 MANAGEMENT BONUS PLAN 

 

	1.	The Plan. The Progressive Corporation and its subsidiaries (collectively “Progressive” or the “Company”) have adopted the 2013
Progressive Capital Management Bonus Plan (the “Plan”) as part of their compensation program for the Company’s investment professionals for the Company’s 2013 fiscal year (the “Plan year”). The Plan is performance-based
and is administered under the direction of the Compensation Committee of the Board of Directors of The Progressive Corporation (the “Compensation Committee” or “Committee”). References in this Plan to the investment results of
the Company mean the applicable results achieved by the Company’s subsidiaries and affiliate in their respective investment portfolios on an aggregate basis. 

 The Company’s investment professionals invest the funds of the Company in accordance with investment guidelines approved from time to time by the Investment and Capital Committee of the Board of
Directors. Those guidelines address such matters as minimum average credit quality and the duration of the portfolio, as well as limitations on the extent to which the portfolio can be concentrated in individual issuers. Compliance with the
guidelines is routinely monitored and variations therefrom must be reported to, and approved by, the Investment and Capital Committee. 
  

	2.	Participants. Progressive employees who are assigned primarily to the Company’s capital management function, including the Company’s Chief
Investment Officer (“CIO”), are eligible to be selected for participation in the Plan. Eligible employees in addition to the CIO will be selected by the CIO in consultation with the Chief Executive Officer (“CEO”) and Chief Human
Resource Officer (“CHRO”) (the “Designated Executives”) to participate in the Plan. Participants may also participate in other Gainsharing, bonus or incentive compensation plans maintained by Progressive, if so determined by the
Designated Executives (or in the case of the CIO or any other executive officer, by the Compensation Committee). Other eligible employees of the Company may be selected for participation in the Plan for or at any time during the Plan year by the
Designated Executives. In such cases, the Designated Executives will determine the new participant’s Target Percentage (described below) and other terms of participation (except with respect to the CIO or any other executive officer, as to whom
all determinations must be made by the Committee). Throughout this Plan, references to “executive officers” refer to executive officers within the meaning of any Securities and Exchange Commission (“SEC”) or New York Stock
Exchange rule applicable to the Company. 

  

	3.	Annual Bonus Determination. 

  

	 	A.	Annual Bonus. Each participant may earn an annual cash bonus (the “Annual Bonus”), subject to the terms of this Plan. The amount of the Annual Bonus
earned by any participant will be determined by application of the following formula: 

 Annual Bonus = Paid
Eligible Earnings x Target Percentage x Performance Factor 
  

	 	B.	Paid Eligible Earnings. Paid Eligible Earnings for the Plan year shall mean and include the following: regular, Earned Time Benefit pay (excluding the payout of
unused Earned Time Benefit pay at termination), sick pay, holiday pay, funeral pay, military make-up pay, overtime pay, shift differential, and retroactive payments of any of the foregoing items, received by the participant during the Plan year for
work or services performed as an officer or employee of Progressive. 

  
 1 

 For purposes of the Plan, Paid Eligible Earnings shall exclude all other types of
compensation, including, without limitation, any short-term or long-term disability payments made to the participant, the earnings replacement component of any worker’s compensation award, any bonus, Gainsharing or other incentive compensation
or equity-based award, including, without limitation, payments from any discretionary cash fund, any dividend payments and any unused Earned Time Benefit. 
  

	 	C.	Target Percentage. The Target Percentages for participants in the Plan shall be determined by or under the direction of the Committee, but will not exceed 125%
for any participant. Target Percentages may vary among Plan participants and may be changed from year to year by or under the direction of the Designated Executives (or in the case of the CIO or any other executive officer, by the Compensation
Committee). 

  

	 	D.	Performance Factor. The Performance Factor will be determined by the Committee after the expiration of the Plan year based on the performance of the
Company’s fixed-income investment portfolio (the “Fixed-Income Portfolio” or “Portfolio”), and such other factors and information relating to the performance of the Company’s investment professionals as the Committee
shall determine. 

 First, an indicated performance factor will be determined based on the fully taxable equivalent
total return of the Fixed-Income Portfolio, in comparison to the total returns of the group of comparable investment firms identified by Rogers Casey (the “Investment Benchmark”), over the one- and three-year periods ending on
December 31 of the Plan year, as described below. After the end of the Plan year, Rogers Casey will determine the firms that are included in the Investment Benchmark in accordance with the criteria specified on Exhibit I hereto. Rogers
Casey will also provide to the Company the monthly total return data for each of the Investment Benchmark firms for the three-year period ending on December 31 of the Plan year. 

Investment results for the Fixed-Income Portfolio will be marked to market, including the benefit of any state premium tax abatements for
municipal securities held in the Portfolio that are realized by the Company during the Plan year, in order to calculate the Portfolio’s fully taxable equivalent total return for the one-year (2013) and three-year period (2011-2013)
periods, in each case compounded on a monthly basis. The investment performance achieved by the Fixed-Income Portfolio for the one- and three-year periods (each, a “comparison period”) will then be compared against the total returns of the
firms included in the Investment Benchmark for the same periods, also compounded on a monthly basis, as determined by the Company from the monthly performance data supplied by Rogers Casey for each firm in the Investment Benchmark, to determine, for
each comparison period, where the Fixed Income Portfolio’s performance falls on a percentile basis when compared to the firms in the Investment Benchmark, as further described on Exhibit II (“Performance Ranking”). 

The Portfolio’s Performance Ranking will be used to determine a performance score of between 0 and 2.0 for each comparison period,
based on the following schedule: 
  

							
	 Comparison
 Period
	 	 Score = 0

Rank at or below
	 	 Score = 1.0

Rank equal to
	 	 Score = 2.0

Rank at or above

	 One year
	 	15th Percentile	 	50th Percentile	 	85th Percentile
	 Three year
	 	25th Percentile	 	50th Percentile	 	75th Percentile

  
 2 

 A Performance Ranking between the values identified in the schedule will be interpolated on
a straight-line basis to generate the applicable performance score, as further described on Exhibit II. Once these performance scores are determined, an overall indicated performance factor will be determined by averaging the performance
scores for the one- and three-year comparison periods. 
 The overall indicated performance factor will be reported to the
Compensation Committee after the expiration of the Plan year, together with such supporting documentation as the Committee may require. The Committee may consider such additional information as it deems necessary or appropriate in its discretion.
Such information may include, without limitation: 
  

	 	•	 	 the primary investment factors that are responsible for favorable or unfavorable results relative to the peer group, such as the Company’s
duration and yield curve position and the extent of its exposure to sectors of the fixed-income markets, including corporate bonds, residential mortgage-backed securities, commercial mortgage-backed securities, other asset-backed securities,
government bonds, preferred stocks and non-investment-grade bonds; 

  

	 	•	 	 the Company’s holdings within each sector relative to the general market composition of each sector; 

 

	 	•	 	 the extent to which material investment decisions may have been driven by Company strategic or capital considerations; and

  

	 	•	 	 the impact on investment results of significant portfolio cash flows driven by Company operations, strategic decisions or capital transactions.

 In addition, the Committee may choose to consult with others, including, without limitation, management, the
Board’s Investment and Capital Committee, other Board members, and outside compensation and investment professionals, in evaluating the performance of the Company’s investment professionals for the year. The Committee will then determine
the Performance Factor, provided that under no circumstances may the Performance Factor exceed 2.0 for the year. 
  

	 	E.	In the event that Rogers Casey (or its successor or assigns) discontinues providing the data that is necessary to make the calculations required by this Plan, or
modifies the information in such a way as to render the comparisons required by this Plan to be not meaningful, in the Committee’s sole judgment, the determinations required above shall be made using investment return data for comparable firms
satisfying the criteria set forth on Exhibit I as may be available from another recognized provider of investment industry data as the Committee may approve in its sole discretion. 

 

	4.	Payment Procedures; Deferral. The Annual Bonuses will be determined and paid to Plan participants as soon as practicable after the Performance Factor has
been determined by the Committee, but no later than March 15th following the Plan year. 

 Any Plan
participant who is eligible to participate in The Progressive Corporation Executive Deferred Compensation Plan (“Deferral Plan”) may elect to defer all or any portion of his or her Annual Bonus otherwise payable under this Plan, subject to
and in accordance with the terms of the Deferral Plan. 
  

	5.	Qualification Date; Leave of Absence; Withholding. Unless otherwise determined by the Committee, and except as otherwise provided herein, in order to be
entitled to receive an Annual Bonus for the Plan year, the participant must be an active employee of Progressive on November 30 of the Plan year (“Qualification Date”). Any participant who is on a leave of absence covered by the

  
 3 

 Family and Medical Leave Act of 1993, personal leave approved by the Company, military leave
or short- or long-term disability (provided that, in the case of a long-term disability, the participant is still an employee of the Company) on the Qualification Date relating to the Plan year will be entitled to receive an Annual Bonus for the
Plan year based on the Paid Eligible Earnings received by the participant during the Plan year. Annual Bonus payments made to participants will be net of any legally required deductions for federal, state and local taxes and other items. 

 

	 	6.	Other Plans. Participants may be selected to participate in this Plan and in one or more other incentive plans offered by the Company. In the case of the
CIO or any other executive officer, all determinations with respect to such incentive plans and the executive’s participation therein shall be made by the Compensation Committee. In all other cases, the Designated Executives shall have full
authority to determine the incentive plan or plans in which any employee shall participate during the Plan year and the weighting factor (if any) that will apply to each such plan. 

 

	 	7.	Non-Transferability. The right to any Annual Bonuses hereunder may not be sold, transferred, assigned or encumbered by any participant. Nothing herein
shall prevent any participant’s interest hereunder from being subject to involuntary attachment, levy or other legal process. 

  

	 	8.	Administration. The Plan will be administered by or under the direction of the Committee. The Committee will have the authority to adopt, alter, amend,
modify and repeal such rules, guidelines, procedures and practices governing the Plan as it, from time to time, in its sole discretion deems advisable. 

 The Committee will have full authority to determine the manner in which the Plan will operate, to interpret the provisions of the Plan and to make all determinations thereunder. All such interpretations
and determinations will be final and binding on Progressive, all Plan participants and all other parties. No such interpretation or determination may be relied on as a precedent for any similar action or decision. 

Unless otherwise determined by the Committee and except as provided in the immediately succeeding paragraph, all of the authority of the
Committee hereunder (including, without limitation, the authority to administer the Plan, select the persons entitled to participate herein, interpret the provisions hereof, waive any of the requirements specified herein and make determinations
hereunder and to establish, approve, change or modify Investment Benchmarks, Performance Targets and Target Percentages) may be exercised by the Designated Officers. If one or more of said officers is unavailable or unable to participate, or if such
position is vacant, the Chief Financial Officer may act instead of such officer. 
 Notwithstanding anything in this Plan to the
contrary: (a) all determinations made under this Plan with respect to the CIO or any other individual deemed to be an executive officer of the Company must be made only by the Compensation Committee; and (b) only the Committee may make the
determination of the Performance Factor required by Section 3.D. above. 
  

	9.	Miscellaneous. 

  

	 	A.	Recoupment. Progressive shall have the right to recoup any Annual Bonus (or an appropriate portion thereof, as hereinafter provided) with respect to any Plan
year paid to a participant hereunder who was an executive officer of Progressive at any time during such Plan year, if: (i) the Annual Bonus payment was predicated upon the achievement during such Plan year of certain financial or operating
results (which includes, for purposes hereof, the performance of the Fixed-Income Portfolio); (ii) such financial or operating results were incorrect and were subsequently the subject of a restatement by Progressive within three (3) years
after the date on 

  
 4 

 which such Annual Bonus was paid to the participant; and (iii) a lower payment would
have been made to the participant if the restated financial or operating results had been known at the time the payment was made. Such recoupment right shall be available to Progressive whether or not the participant in question was at fault or
responsible in any way in causing such restatement. In such circumstances, Progressive will have the right to recover from each participant for such Plan year, and each such participant will refund to Progressive, the amount by which the Annual
Bonus paid to such participant for the Plan year in question exceeded the lower payment that would have been made based on the restated results, without interest; provided, however, that Progressive will not seek to recover such amounts unless the
amount due would exceed the lesser of five percent (5%) of the Annual Bonus previously paid or twenty-thousand dollars ($20,000). Such recovery, at the Committee’s discretion, may be made by lump sum payment, installment payments, credits
against future bonus payments, or other appropriate mechanism. 
  

	 	B.	Further Rights. Notwithstanding the foregoing subsection A., if any participant that was an executive officer at any time during such Plan year engaged in fraud
or other misconduct (as determined by the Committee or the Board, in their respective sole discretion) resulting, in whole or in part, in a restatement of the financial or operating results used hereunder to determine the Annual Bonuses for a
specific Plan year, Progressive will further have the right to recover from such participant, and the participant will refund to Progressive upon demand, an amount equal to the entire Annual Bonus paid to such participant for such Plan year plus
interest at the rate of eight percent (8%) per annum or, if lower, the highest rate permitted by law, calculated from the date that such bonus was paid to the participant. Progressive shall further have the right to recover from such
participant Progressive’s costs and expenses incurred in connection with recovering such Annual Bonus from the participant, including, without limitation, reasonable attorneys’ fees. There shall be no time limit on the Company’s right
to recover such amounts under this subsection B., except as otherwise provided by applicable law. 

  

	 	C.	Rights Not Exclusive. The rights contained in the foregoing subsections A. and B. shall be in addition to, and shall not limit, any other rights or remedies that
the Company may have under any applicable law or regulation. 

  

	 	D.	Compliance with Law. The Annual Bonuses determined and paid pursuant to the Plan shall be subject to all applicable laws and regulations. Without limiting the
foregoing, and notwithstanding anything to the contrary contained in this Plan, if the SEC promulgates rules under Section 954 of the Dodd-Frank Wall Street Reform and Consumer Protection Act that require, as a condition to the Company’s
continued listing on a national securities exchange, that the Company develop and implement a policy requiring the recovery of erroneously awarded compensation, and such regulations are applicable to the Annual Bonuses awarded pursuant to the Plan,
then the following shall apply: 

 In the event that the Company is required to prepare a restatement of one or
more of its financial statements due to the material noncompliance of the Company with any financial reporting requirement under the securities laws, the Company will be entitled to recover from each participant hereunder who was at the time of
grant or payment of an Annual Bonus an executive officer of the Company under applicable SEC rules (whether or not such participant remains an executive officer of the Company at the time of such restatement or thereafter), the amount of any Annual
Bonus that (i) was paid during the three year period preceding the date on which the Company is required to prepare such restatement and (ii) is in excess of what would have been paid to the participant under the restatement, or as may
otherwise be required by such rules to be promulgated by the SEC. 

  
 5 

	10.	Termination; Amendments. The Plan may be terminated, amended or revised, in whole or in part, at any time and from time to time by the Committee, in its
sole discretion. 

  

	11.	Unfunded Obligations. The Plan will be unfunded and all payments due under the Plan will be made from Progressive’s general assets.

  

	12.	No Employment Rights. Nothing in the Plan shall be construed as conferring upon any person the right to remain a participant in the Plan or to remain
employed by Progressive, nor shall the Plan limit Progressive’s right to discipline or discharge any of its officers or employees or change any of their job titles, duties or compensation. 

 

	13.	Set off Rights. Progressive shall have the unrestricted right to set off against or recover out of any bonuses or other sums owed to any participant under
the Plan any amounts owed by such participant to Progressive. 

  

	14.	Prior Plans. This Plan supersedes all prior plans, agreements, understandings and arrangements regarding bonuses or other cash incentive compensation
payable or due to any participant from Progressive with respect to the performance of Progressive’s investment portfolio. Without limiting the generality of the foregoing, this Plan supersedes and replaces the 2012 Progressive Capital
Management Bonus Plan (the “Prior Plan”), which is and shall be deemed to have terminated on the last day of the Company’s 2012 fiscal year (the “Prior Plan Termination Date”); provided, however, that any bonuses or other
sums earned and payable under the Prior Plan with respect to any Plan year ended on or prior to the Prior Plan Termination Date shall be unaffected by such termination and shall be paid to the appropriate participants when and as provided
thereunder. 

  

	15.	Effective Date. This Plan is adopted, and is effective, as of the first day of the Company’s 2013 fiscal year and will be effective for the 2013 Plan
year (which coincides with Progressive’s 2013 fiscal year, except that investment returns are calculated on a calendar year basis). 

  

	16.	Governing Law. This Plan shall be interpreted and construed in accordance with the laws of the State of Ohio. 

  
 6 

 EXHIBIT I 

INVESTMENT BENCHMARK CRITERIA 
 After the end of the Plan year, Rogers Casey will determine the firms comprising the Investment Benchmark for the Plan year from its records and will supply to the Company the monthly total returns and
any other relevant data for each of those firms for the three-year period ending on December 31 of the Plan year. 
 A firm will be
included in the Investment Benchmark if Rogers Casey is able to determine from its records that: 
  

	1.	The firm has provided monthly data regarding its holdings and investment return, as necessary to determine or calculate such firm’s monthly total return, and to
evaluate such firm’s compliance with each of the criteria set forth below, for the entire three-year period ending on December 31 of the Plan year; and 

 

	2.	At all times during the three-year period ending on December 31 of the Plan year, the information provided by the firm shows, or Rogers Casey is able to calculate,
that such firm’s investment portfolio satisfies each of the following criteria: 

  

			
	 Duration:
	  	Effective Duration between 1.5 years and 5.0 years
	 Credit Quality Average
	  	= A, or = AA, or = AAA, or = AAA+
	 Convexity (%)
	  	>= -1
	 Sector Allocation:
	  	U.S. High Yield Corporate Debt <= 10%
	 Sector Allocation:
	  	Mortgages <= 60%
	 Sector Allocation:
	  	U.S. Investment Grade Corporate Debt <= 60%
	 Sector Allocation:
	  	CMBS <= 60%
	 Sector Allocation:
	  	ABS <= 60%
	 Sector Allocation:
	  	Emerging Markets Debt <= 5%

  

	3.	The Company will have no discretion to alter the Investment Benchmark list after it is finalized by Rogers Casey. 

  
 7 

 EXHIBIT II 

DETERMINATION OF PERFORMANCE RANKING AND PERFORMANCE SCORES 
 Once all the total returns are calculated, the data is sorted in descending order from highest to lowest total return. From here, the process to compute the Performance Factor is as follows (this Exhibit
shows the procedures and related calculations for the 1-year comparison period required by the Plan; the calculations for the 3-year comparison period would follow the same procedures, except that necessary adjustments would be made to determine the
top and bottom 25% levels and the performance score variances between those levels): 
 INTERPOLATED VALUES FOR SETTING TOP AND BOTTOM 15%
LEVELS 
 The top 15% and bottom 15% total return rankings are computed based on the total number of firms in the Investment Benchmark, excluding
the PCM Fixed-Income Portfolio return. For example, if there were 279 participants, the return required to earn a 2.0 portfolio performance factor would be determined by interpolating between the forty-first and forty-second firm’s returns,
since 15% of 279 = 41.85. The same procedure would be used to determine the 0.0 portfolio performance factor. 
 The total returns, computed by
Investment Accounting, for the interpolated positions are calculated as follows (continuing to use an example of 279 survey firms): 
 Interpolated Value = Firm 41 return – ((Firm 41 Return – Firm 42 Return)*0.85) 
 Firm 41 = 18.35% 
 Firm 42 = 18.23% 

Firm 41.85 (Interpolated Value) = 18.35% – ((18.35% – 18.23%)*0.85) = 18.25%. 

In this case, the PCM Performance Factor will equal 2.0 if its total return equals the interpolated value for Firm 41.85 of 18.25%. A similar calculation
is then used to determine the bottom 15% group and interpolated value for a 0.0 performance score. 
 Once the two groups are computed, top and
bottom 15%, the remainder of the performance scores are calculated as follows: 
 Performance score variance =
(2.00) / Number of positions from first participant after the top 15% ranking to the 1st participant in the bottom 15% ranking. In the case of 279 participants, the number of positions to divide the 2.00 performance factors by would be 198. 

The calculation for the performance score variance from 2.00 – 0.00 would be: 

2.00 / 198 = .010101 per position for 279 firms 
 In the case of a tie in total returns between firms, each firm will have the same performance score, one step under the next higher position. The next lowest position would then be stepped down by a
factor based on the number of participants who tie. In the case of a tie between two firms, the step down will be twice the performance score variance to maintain the proper stepping to the 0.00 performance score level. 

Example: If firms 42 and 43 each had the same total return in the 279 firm example, then firms 42 and 43 would each have a Performance
Factor of 1.989899, which is 2.00 – .0010101. The number 44 position in this example would have a performance score of 1.969697, which is the required step down from 42 to 44. 

  
 8 

 In addition, if the returns are tied between the interpolated value set for the 2.00 performance score and
any position below the 2.00 level, those lower positions will also be set to a 2.00 performance score. The step down factor in the performance score will work similarly as noted in the example above. For the last 15% group, all firms with total
returns equaling the last interpolated total return value would have the same performance score as the last interpolated value (.0101012), and all others in the last 15% group would have a 0.00 Portfolio Performance Factor. 

Once all the performance scores have been created, from 2.00 to 0.00, PCM’s return is compared to the rankings to determine its Performance Factor.
If the PCM return is not in the top or bottom 15% and does not match the return of any participant, then PCM’s Performance Factor is an interpolated value between the firms with the next highest and next lowest returns. 

The interpolation computation for the Performance Factor based on PCM’s return is as follows: 

Performance score of firm below PCM return + (PCM’s Return – Return below PCM) / (Return above PCM – Return below PCM) *
(Performance score of firm above PCM – Performance score of firm below PCM) 
 Assuming the following data, using the 279 firm example:

  

									
	 Firm
	  	 Performance score
	 	  	 Total return
	 
	 Firm above PCM
	  	 	.90	  	  	 	13.61	  
	 PCM
	  				  	 	13.39	  
	 Firm below PCM
	  	 	.89	  	  	 	13.34	  

 The calculation of PCM’s Performance Factor is: 

0.89 + (13.39-13.34) / (13.61-13.34) * (0.90-0.89) = 0.89 
 The final performance score is rounded to the nearest one-hundredth, if necessary. 

  
 9Exhibit 10.6

 Exhibit 10.6 
 JULIAN MICHAEL CUSACK 
 AND 

ASPEN INSURANCE UK SERVICES LIMITED 
  

 
 AMENDED AND
RESTATED SERVICE AGREEMENT 
  
  

 TABLE OF CONTENTS 

 

							
	 Clause
	  	 	  	Page	 
			
	1.	  	 INTERPRETATION
	  	 	3	  
	2.	  	 AMENDMENT AND RESTATEMENT
	  	 	4	  
	3.	  	 POSITION
	  	 	4	  
	4.	  	 TERM
	  	 	4	  
	5.	  	 DUTIES
	  	 	4	  
	6.	  	 REMUNERATION AND COMMISSION
	  	 	5	  
	7.	  	 PENSION AND INSURANCE BENEFITS
	  	 	6	  
	8.	  	 EXPENSES
	  	 	7	  
	9.	  	 HOLIDAYS AND HOLIDAY PAY
	  	 	7	  
	10.	  	 DISABILITY OR DEATH
	  	 	7	  
	11.	  	 CONFIDENTIAL INFORMATION
	  	 	8	  
	12.	  	 COPYRIGHT AND DESIGNS
	  	 	9	  
	13.	  	 GRATUITIES AND CODES OF CONDUCT
	  	 	9	  
	14.	  	 RESTRICTIVE COVENANTS
	  	 	9	  
	15.	  	 TERMINATION BY RECONSTRUCTION OR AMALGAMATION; CHANGE IN CONTROL
	  	 	9	  
	16.	  	 TERMINATION OF EMPLOYMENT BY THE COMPANY FOR CAUSE
	  	 	12	  
	17.	  	 TERMINATION OF EMPLOYMENT BY THE COMPANY WITHOUT CAUSE
	  	 	12	  
	18.	  	 TERMINATION OF EMPLOYMENT BY THE EMPLOYEE
	  	 	13	  
	19.	  	 OBLIGATIONS UPON TERMINATION OF EMPLOYMENT; CERTAIN OTHER TERMINATIONS
	  	 	14	  
	20.	  	 EFFECT OF TERMINATION OF THIS AGREEMENT
	  	 	15	  
	21.	  	 GENERAL RELEASE
	  	 	15	  
	22.	  	 OTHER TERMS AND CONDITIONS
	  	 	16	  
	23.	  	 NOTICES
	  	 	16	  
	24.	  	 PREVIOUS AND OTHER AGREEMENTS
	  	 	16	  
	25.	  	 ENTIRE AGREEMENT/AMENDMENT
	  	 	17	  
	26.	  	 ASSIGNMENT
	  	 	17	  
	27.	  	 SEVERABILITY
	  	 	17	  
	28.	  	 SUCCESSORS/BINDING AGREEMENT
	  	 	17	  
	29.	  	 CO-OPERATION
	  	 	17	  
	30.	  	 GOVERNING LAW
	  	 	17	  
	31.	  	 COUNTERPARTS
	  	 	18	  

 . 

 AMENDED AND RESTATED SERVICE AGREEMENT 

 

			
	DATE:	 	25 February 2013

 PARTIES: 
  

	(1)	JULIAN MICHAEL CUSACK of [Address] (the “Employee”); and 

 

	(2)	ASPEN INSURANCE UK SERVICES LIMITED (Registered in England No. 1184193), 30 Fenchurch St, London, EC3M 3BD, England (the “Company”).

 OPERATIVE TERMS: 
  

	1.	INTERPRETATION 

  

	1.1	In this Agreement: 

  

			
	“Affiliate”	  	means any entity directly or indirectly controlling, controlled by, or under common control with the Company; or any other entity designated by the Board in which the Company or an
Affiliate has an interest;
		
	“Board”	  	means the Board of Directors of Holdings from time to time;
		
	“Group”	  	means the Company and its Affiliates (and “Group Company” means the Company or any one of its Affiliates);
		
	“Holdings”	  	means Aspen Insurance Holdings Limited, a Bermuda limited company, the ultimate holding company of the Company and its Affiliates;
		
	 “Manager”
	  	means the Chief Executive Officer of Holdings or such other person as the Company may nominate from time to time as the person to whom the Employee shall report.

  

	1.2	In this Agreement references to any statutory provision shall include such provision as from time to time amended, whether before on or (in the case of re-enactment or
consolidation only) after the date hereof, and shall be deemed to include provision of earlier legislation (as from time to time amended) which have been re-enacted (with or without modification) or replaced (directly or indirectly) by such
provision and shall further include all statutory instruments or orders from time to time made pursuant thereto. 

	

	2.	AMENDMENT AND RESTATEMENT 

This Agreement shall serve as a complete amendment and restatement of the Service Agreement entered into between the Employee and the
Company dated 27 October 2011 (which was itself an amendment and restatement of (i) the Service Agreement entered into between the Employee and Holdings, and (ii) the Service Agreement entered into between the Employee and the
Company, each dated 1 May 2008, and which were themselves an amendment and restatement of the Service Agreement entered into between Julian Cusack and Holdings dated 1 May 2007) (collectively the “Original Agreements”).
Except as otherwise provided herein, all terms of the Original Agreements shall be superseded by the terms of this Agreement and, upon execution of this Agreement, the Original Agreements shall be of no further force and effect. 

 

	3.	POSITION 

 The Company
shall employ the Employee as Strategic Projects Officer of the Group or such other duties as may be agreed between the Employee and the Manager from time to time. 
  

	4.	TERM 

  

	4.1	The Company shall employ the Employee, and the Employee shall serve the Company, on the terms and conditions set forth in this Agreement, beginning on the date hereof
(the “Effective Date”) and continuing unless and until terminated in accordance with the provisions contained in this Agreement. 

  

	4.2	Notwithstanding the provisions of Clause 3, it is anticipated that the Employee’s employment will terminate by mutual agreement when the Employee reaches the age
of 70 years. 

  

	5.	DUTIES 

  

	5.1	During his employment hereunder the Employee shall: 

  

	 	(a)	report to the Manager and perform the duties and exercise the powers and functions which from time to time may reasonably be assigned to or vested in him by the Board
in relation to Holdings and any other Group Company to the extent consistent with his job title set out in Clause 3 (without being entitled to any additional remuneration in respect of such duties for any Group Company); 

 

	 	(b)	for four business days per week (subject to any holiday time taken in accordance with clause 9 and all applicable statutory holidays) devote the whole of his working
time, attention and ability to his duties in relation to the Company and any other Group Company at such place or places as the Board shall determine. The Employee shall carry out his duties under this Agreement at the Company’s premises at 30
Fenchurch St, London EC3M 3BD, or such other place as the Company and the Employee shall mutually agree, provided that the Employee shall not be required to reside outside of the United Kingdom; 

 

	 	(c)	comply with all reasonable requests, instructions and regulations given or made by the Board (or by any one authorised by it) and promptly provide such explanations,
information and assistance as to the performance of his duties assigned to him under this Agreement as the Board may reasonably require; 

	 	(d)	faithfully and loyally serve Holdings and each other Group Company to the best of his ability and use his utmost endeavours to promote its interests in all respects;

  

	 	(e)	not engage in any activities which would detract from the proper performance of his duties hereunder, nor without the prior written consent of the Board in any capacity
including as director, shareholder, principal, consultant, agent, partner or employee of any other company, firm or person (save as the holder for investment of securities which do not exceed three percent (3%) in nominal value of the share
capital or stock of any class of any company quoted on a recognised stock exchange) engage or be concerned or interested directly or indirectly in any other trade, business or occupation whatsoever; and 

 

	 	(f)	comply (and shall use every reasonable endeavour to procure that his spouse and minor children will comply) with all applicable rules of law, stock exchange
regulations, individual registration requirements (at a cost to be borne by the Company) and codes of conduct of Holdings and any other Group Company in effect with respect to dealing in shares, debentures or other securities of Holdings or other
Group Company. 

  

	5.2	Nothing herein shall preclude the Employee from (a) serving on the boards of directors of a reasonable number of other corporations subject to the approval of the
Chief Executive Officer of the Company in each case, which approval shall not be unreasonably withheld, (b) serving on the boards of a reasonable number of trade associations subject to the approval of the Board, which approval shall not
unreasonably be withheld, and/or charitable organizations, (c) engaging in any charitable activities and community affairs, and (d) managing his personal investments and affairs, provided that such activities set forth in this Clause 5.2
do not significantly interfere with the performance of his duties and responsibilities to any Group Company. 

  

	6.	REMUNERATION AND COMMISSION 

  

	6.1	The Employee shall be paid by way of remuneration for his services during his employment hereunder a salary at the rate (the “Salary Rate”) of
£300,000 per annum (less necessary deductions for income tax and national insurance and any other authorised deductions), subject to increase pursuant to Clause 6.3, which shall be inclusive of any fees to which the Employee may be
entitled as a director of Holdings or of any other Group Company. This sum shall also be inclusive of a payment in lieu of pension contributions in accordance with clause 7.1. 

 

	6.2	The Employee shall be eligible for a cash bonus, based on a bonus potential of 60% of his annual salary, during his employment hereunder of such amounts (if any) at
such times and subject to such conditions as the Manager of may in its absolute discretion decide. 

  

	6.3	The Company shall review the Salary Rate for increase at least once each year, and any change in the Salary Rate resulting from such review will take effect from 1
April. 

	6.4	The Employee’s salary will be payable by equal monthly installments; each monthly installments will be in respect of a calendar month and will be paid on or before
the last day of such calendar month. Where the employment has begun or ended in a calendar month, salary in respect of that month will be the proportion of a normal month’s installments which the days of employment in that month bear to the
total days in the month. 

  

	6.5	The Company may withhold from amounts payable under this Agreement all applicable taxes that are required to be withheld by applicable laws or regulations.

  

	7.	PENSION AND INSURANCE BENEFITS 

  

	7.1	The Employee has advised the Company that he has reached the current UK pension lifetime allowance and, accordingly, does not wish to receive additional payments in to
the Company’s pension plan or other pension contributions under this Agreement. Accordingly, the Salary Rate set out at clause 6.1 (together with any revised Salary Rate set in accordance with clause 6.3) shall be deemed to be inclusive of a
payment in lieu of pension contributions. 

  

	7.2	Subject to the provisions of clause 7.1, during his employment hereunder, the Employee shall be entitled to participate in all other employee benefit plans and programs
made available to the Company’s employees generally, as such plans or programs may be in effect from time to time. 

  

	7.3	During his employment hereunder, the Company shall (subject to the relevant insurers’ terms and conditions) provide the Employee with: 

 

	 	7.3.1	medical insurance; 

  

	 	7.3.2	permanent health insurance; 

  

	 	7.3.3	personal accident insurance; and 

  

	 	7.3.4	Contract life insurance. 

 The
Board shall have the right to change the arrangements for the provision of such benefits as it sees fit or, if in the reasonable opinion of the Board, the Company is unable to secure any such insurance under the rules of any applicable scheme or
otherwise at reasonable rates to cease to provide any or all of the insurances unless in either case the Employee or a member of his family is at that time suffering from a medical condition which would entitle them to benefits under the policy in
question in which case the existing policy is to be maintained in force by the Company or an alternative policy provided which would provide the same benefit in relation to the medical condition in question. 

 

	8.	EXPENSES 

 The Company
shall reimburse to the Employee all traveling, hotel, entertainment and other expenses properly and reasonably incurred by him in the performance of his duties hereunder and properly claimed and vouched for in accordance with the Company’s
expense reporting procedure in force from time to time. 

	9.	HOLIDAYS AND HOLIDAY PAY 

  

	9.1	The Employee shall be entitled to an aggregate of 24 working days’ paid holiday per holiday year (in addition to public holidays) in relation to his employment by
the Company and, if applicable, such additional days as are set out in the Company’s standard terms and conditions of employment from time to time, during each holiday year to be taken at such time or times as may be agreed with the Manager.
Except as otherwise provided in the Company’s holiday policy, the Employee may not carry forward any unused part of his holiday entitlement to a subsequent holiday year and the Employee shall not be entitled to any salary in lieu of untaken
holiday. 

  

	9.2	For the holiday year during which the Employee’s employment hereunder commences or terminates he shall be entitled to such proportion of his annual holiday
entitlement as the period of his employment in each such holiday year bears to one holiday year as set out in the Company’s holiday policy. Upon termination of his employment for whatever reason, he shall, if appropriate, be entitled to salary
in lieu of any outstanding holiday entitlement. 

  

	10.	DISABILITY OR DEATH 

  

	10.1	The Company reserves the right at any time to require the Employee (at the expense of the Company) to be examined by a medical adviser nominated by the Company and the
Employee consents to the medical adviser disclosing the results of the examination to the Company and shall provide the Company with such formal consents as may be necessary for this purpose. 

 

	10.2	If the Employee shall be prevented by illness, accident or other incapacity from properly performing his duties hereunder he shall report this fact forthwith to the
Company Secretary’s office and if he is so prevented for seven or more consecutive days he shall if required by the Company provide an appropriate doctor’s certificate. 

 

	10.3	If the Employee shall be absent from his duties hereunder owing to illness, accident or other incapacity duly certified in accordance with the provisions of clause 10.2
he shall be paid his full remuneration for any period of absence of up to a maximum of 26 weeks in aggregate in any period of 52 consecutive weeks and thereafter, subject to the provisions of clause 17, to such remuneration (if any) as the Board
shall in its absolute discretion allow provided that the Company may not terminate the employment of the Employee under this clause without his consent at a time when he is unable to perform his duties through illness if the consequence of such
termination would be to deprive him of any benefits that would otherwise be payable to him under the provisions of any permanent health insurance policy taken out by the Company. 

 

	10.4	In the event that the Employee’s employment is terminated due to his death, his estate or his beneficiaries, as the case may be, shall be entitled to:
(a) salary at his Salary Rate up to and including the end of the month in which his death occurs, (b) the annual incentive award, if any, to which the Employee would have been entitled to pursuant to Clause 6.2 for the year in which the
Employee’s death occurs, multiplied by a fraction, the numerator of which is the number of days that the Employee was employed during the applicable year and the denominator of which is 365, and (c) the unpaid balance of all previously
earned cash bonus and other incentive awards with respect to performance periods which have been completed, all of which amounts shall be payable in a lump sum in cash within 30 days after his death, except that the pro-rated incentive award shall
be payable when such award would have otherwise been payable had the Employee not died. 

	11.	CONFIDENTIAL INFORMATION 

  

	11.1	Except as otherwise provided in this Section, the Employee shall not during his employment hereunder or at any time after his termination for any reason whatsoever
disclose to any person whatsoever or otherwise make use of any Confidential Information. 

  

	11.2	As used in this Section, the term “Confidential Information” shall mean any confidential or secret information which he has or may have acquired in the course
of his employment relating to Holdings or any other Group Company or any customers or clients of the Holdings or any other Group Company, including without limiting the generality of foregoing: 

 

	 	11.2.1	confidential or secret information relating to the past, current or future business, finances, activities and operations of Holdings or any other Group Company;

  

	 	11.2.2	confidential or secret information relating to the past, current or future business, finances, activities and operations of any third party to the extent that such
information was obtained by Holdings or any other Group Company pursuant to a confidentiality agreement; 

 but
shall not include information that is generally known to, or recognised as standard practice in, the industry in which the Company is engaged unless such information is known or recognised as a result of the Employee’s breach of this covenant.

  

	11.3	The Employee will only use Confidential Information for the benefit of Holdings or any other Group Company in the course of his employment and shall at all times
exercise all due care and diligence to prevent the unauthorised disclosure or use of Confidential Information. 

  

	11.4	In the event that the Employee becomes compelled by a court or administrative order to disclose any of the Confidential Information other than as permitted pursuant to
this Section, he will provide prompt notice to Holdings so that Holdings may seek a protective order or other appropriate remedy. In the event that Holdings fails to seek, or seeks and fails to obtain, such a protective order or other protective
remedy, the Employee will furnish only that portion of the Confidential Information that, in the opinion of his counsel, he is legally required to furnish. 

 

	12.	COPYRIGHT AND DESIGNS 

  

	12.1	The Employee hereby assigns to the Company all present and future copyright, design rights and other proprietary rights if any for the full term thereof throughout the
world in respect of all works originated by him at any time during the period of his employment by the Company or any other Group Company whether during the course of his normal duties or other duties specifically assigned to him (whether or not
during normal working hours) either alone or in conjunction with any other person and in which copyright or design rights may subsist except only those designs or other works written, originated, conceived or made by him wholly unconnected with his
service hereunder. 

	12.2	The Employee agrees and undertakes that he will execute such deeds or documents and do all such acts and things as may be necessary or desirable to substantiate the
rights of the Company in respect of the matters referred to in this Clause. To secure his obligation under this Agreement the Employee irrevocably appoints the Company to be his attorney in his name and on his behalf to execute such deeds or
documents and do all such acts and things as may be necessary or desirable to substantiate the rights of the Company in respect of the matters referred to in this Clause. 

 

	12.3	The Employee hereby irrevocably waives all moral rights that he had or may have in any of the works referred to in Clause 12.1, subject to the exception therein.

  

	13.	GRATUITIES AND CODES OF CONDUCT 

  

	13.1	The Employee shall comply with all codes of conduct from time to time adopted by the Board. 

 

	13.2	The Employee shall not, except in accordance with the Company’s Gift and Hospitality Policy and any other code of conduct adopted by the Board or with the prior
written consent of the Board, directly or indirectly accept any commission, rebate, discount, gratuity or gift, in cash or in kind from any person who has or is likely to have a business relationship with the Company or any other Group Company and
shall notify the Company upon acceptance by the Employee of any commission, rebate, discount, gratuity or gift in accordance with the Company’s Gift and Hospitality Policy or any such code of conduct from time to time. 

 

	14.	RESTRICTIVE COVENANTS 

  

	14.1	For the purpose of this Clause: 

“the Business” means the business of the Group or any Group Company at the date of termination of the Employee’s
employment with which the Employee has been concerned to a material extent at any time in the Relevant Period; 
 references to
the “Group” and “Group Companies” shall only be reference to the Group and Group Companies in respect of which the Employee has carried out material duties in the Relevant Period; 

“Relevant Period” shall mean the period of 24 months immediately preceding the date on which the Restricted Period
defined in clause 14.3 commences or the date on which the Company seeks to enforce the restriction in question; 

“Restricted Person” shall mean any person who or which has at any time during the Relevant Period done business with the
Company or any other Group Company as customer or client or consultant and whom or which the Employee shall have had personal dealings with, contact with or responsibility for (each, in a business or commercial capacity) during the Relevant Period;

 “Key Employee” shall mean any person who at the date of termination of the Employee’s employment is
employed or engaged by the Company or any other Group Company with whom the Employee has had material contact during the Relevant Period and (a) is employed or engaged in the capacity of Manager, Underwriter or otherwise in a

 
senior capacity or in any other capacity as may be agreed in writing between the Employee Committee and the Employee from time to time and/or (b) is in the possession of Confidential
Information and/or (c) is directly managed by or reports to the Employee. 

	14.2	The Employee covenants with the Company that he will not in connection with the carrying on of any business in competition with the Business during his employment or
any Restricted Period applicable upon the termination of the Employee’s employment (as defined in clause 14.3) without the prior written consent of the Board either alone or jointly with or on behalf of any person directly or indirectly:

  

	 	14.2.1	canvass, solicit or approach or cause to be canvassed or solicited or approached for orders in respect of any services provided and/or any products sold by the Company
or any other Group Company any Restricted Person; 

  

	 	14.2.2	solicit or entice away or endeavour to solicit or entice away from the Company or any other Group Company any Key Employee; 

 

	 	14.2.3	be employed, engaged, interested in or concerned with any business or undertaking which is engaged in or carries on business in the United Kingdom, Bermuda or the USA
which is or is about to be in competition with the Business; 

  

	14.3	The length of the Restricted Period depends upon the circumstances in which the Employee’s employment terminates as follows:- 

 

	 	14.3.1	if the Employee serves 6 months’ notice to terminate his employment without Good Reason under clause 18.2 the Restricted Period shall be a period of 6 months (or 9
months in respect of clause 14.2.2 only) from the date on which notice is served which period shall run concurrently with the 6 month notice period irrespective of whether the Employee is working his notice, on garden leave or his employment has
terminated prior to the expiry of the notice period as a result of the Company making a payment pursuant to clause 19.2 within the time period specified in that clause; 

 

	 	14.3.2	if the Company serves notice to terminate the Employee’s employment without Cause under clause 17 the Restricted Period shall be a period of 6 months from the date
on which notice is served by the Company which period shall run concurrently with the 6 month notice period irrespective of whether the Employee is working his notice, on garden leave or his employment has terminated prior to the expiry of the
notice period as a result of the Company making a payment pursuant to clause 19.2 within the time period specified in that clause; 

  

	 	14.3.3	if the Employee serves immediate notice to terminate his employment with Good Reason under clause 18.1 the Restricted Period shall be 6 months from the date of
termination provided the Employee is paid the payment due under clause 19.2 within the time period specified in that clause; 

  

	 	14.3.4	if the Company serves immediate notice to terminate the Employee’s employment with Cause under clause 16.1 the Restricted Period shall be 6 months from the date of
termination provided the Company complies with clause 16.1; 

  

	14.4	 The covenants contained in Clauses 14.2.1, 14.2.2 and 14.2.3 are intended to be separate and severable and enforceable as such. It is expressly
understood and agreed that although the Employee and the Company consider the restrictions contained in this 

	 	
Clause 14 to be reasonable, if a final judicial determination is made by a court of competent jurisdiction that the time or territory or any other restriction contained in this Agreement is an
unenforceable restriction against the Employee, the provisions of this Agreement shall not be rendered void but shall be deemed amended to apply as to such maximum time and territory and to such maximum extent as such court may judicially determine
to be enforceable. Alternatively, if any court of competent jurisdiction finds that any restriction contained in this Agreement is unenforceable, and such restriction cannot be amended so as to make it enforceable, such finding shall not affect the
enforceability of any of the other restrictions contained herein. 

  

	14.5	The Employee acknowledges and agrees that the Company’s remedies at law for a breach of any of the provisions of Clauses 11, 12 or 14 would be inadequate and the
Company would suffer irreparable damages as a result of such breach. In recognition of this fact, the Employee agrees that, in the event of such a breach, in addition to any remedies at law, the Company, without posting any bond, shall be entitled
to obtain equitable relief in the form of specific performance, temporary restraining order, temporary or permanent injunction or any other equitable remedy which may then be available. 

 

	15.	TERMINATION BY RECONSTRUCTION OR AMALGAMATION; CHANGE IN CONTROL 

  

	15.1	If the employment of the Employee hereunder shall be terminated solely by reason of the liquidation of any Group Company for the purposes of amalgamation or
reconstruction or as part of any arrangement for the amalgamation of the undertaking of such Group Company not involving liquidation (in each case, other than a “Change in Control”, as defined below) and the Employee shall be offered
employment with the amalgamated or reconstructed company on the same terms as the terms of this Agreement, the Employee shall have no claim against the Company or any Group Company in respect of the termination of his employment by the Company.

  

	15.2	If the employment of the Employee hereunder shall be terminated by the Company without Cause or by the Employee in connection with a Change in Control the provisions of
Clause 19.1 shall apply. 

  

	16.	TERMINATION OF EMPLOYMENT BY THE COMPANY FOR CAUSE 

  

	16.1	The Company, without prejudice to any remedy which it may have against the Employee for the breach or non-performance of any of the provisions of this Agreement, may by
notice in writing to the Employee forthwith terminate his employment for “Cause”. In the event the Company terminates the Employee’s employment for Cause, the Employee shall be entitled to salary at his Salary Rate through the date of
termination. 

 For purposes of this Agreement, “Cause” shall mean circumstances where the Employee:

  

	 	(a)	becomes bankrupt or becomes the subject of an interim order under the Insolvency Act 1986 or makes any arrangement or composition with his creditors; or

  

	 	(b)	is convicted of any criminal offence (other than an offence under road traffic legislation in the United Kingdom or elsewhere for which a penalty other than
imprisonment is imposed); or 

	 	(c)	is guilty of any serious misconduct, any conduct tending to bring the Company or any other Group Company or himself into disrepute, or any material breach or
non-observance of any of the provisions of this Agreement, or conducts himself in a way which is materially prejudicial or calculated to be materially prejudicial to the business of the Group; or 

 

	 	(d)	is disqualified from being a director of any company by reason of an order made by any competent court; or 

 

	 	(e)	is guilty of any repeated breach or non-observance of any code of conduct or fails or ceases to be registered (where such registration is, in the reasonable opinion of
the Board, required for the performance of his duties) by any regulatory body in the United Kingdom or elsewhere. 

  

	17.	TERMINATION OF EMPLOYMENT BY THE COMPANY WITHOUT CAUSE 

  

	17.1	The Company may terminate the employment of the Employee at any time during the employment hereunder without Cause by either (i) giving to the Employee 6
months’ prior notice in writing; or (ii) terminating the employment of the Employee immediately and paying the Employee in lieu of the notice to which he would have otherwise been entitled under (i) above (which payment in lieu shall
be deemed to be included within the Severance Payment referred to in Clause 19.2) provided that the Company may not terminate the employment of the Employee under this clause without his consent at a time when he is unable to perform his duties
through illness if the consequence of such termination would be to deprive him of any benefits that would otherwise be payable to him under the provisions of any permanent health insurance policy taken out by the Company. 

 

	18.	TERMINATION OF EMPLOYMENT BY THE EMPLOYEE 

  

	18.1	The Employee shall have the right to terminate his employment at any time for Good Reason by immediate notice if, following submission of the written notice by the
Employee to the Company detailing the events alleged to constitute Good Reason in accordance with this Clause, the Company shall have failed to cure such events within the 30 day period following submission of such notice. For purposes of this
Agreement, “Good Reason” shall mean (i) a reduction in the Employee’s annual base salary or annual bonus opportunity, or the failure to pay or provide the same when due, (ii) a material diminution in the Employee’s
duties, authority, responsibilities or title, or the assignment to the Employee of duties or responsibilities which are materially inconsistent with his positions, (iii) the removal of the Employee from the position described in Clause 3;
(iv) the Company’s requiring the Employee to be based at any office or location more than fifty (50) miles from the Employee’s office as of the date hereof; or (v) any other fundamental breach of this Agreement; provided,
however, that no such event(s) shall constitute “Good Reason” unless the Company shall have failed to cure such event(s) within 30 days after receipt by the Company from the Employee of written notice describing in detail such
event(s). 

  

	18.2	The Employee shall have the right to terminate his employment at any time without Good Reason upon giving 6 months’ prior written notice to the Company.

	18.3	If the Employee gives notice to terminate his employment without Good Reason under Clause 18.2 or if the Employee seeks to terminate his employment without Good Reason
and without the notice required by Clause 18.2 or the Company gives notice to terminate the Employee’s employment under Clause 17.1(i), then provided the Company continues to provide the Employee with the salary and contractual benefits in
accordance with this Agreement, the Company has, at its discretion, the right for the period (the “Garden Leave Period”) then outstanding until the date of the termination of the Employee’s employment: 

 

	 	(a)	to exclude the Employee from any premises of the Company or any Group Company and require the Employee not to attend at any premises of the Company or any Group
Company; and/or 

  

	 	(b)	to require the Employee to carry out no duties; and/or 

  

	 	(c)	to require the Employee not to communicate or deal with any employees, agents, consultants, clients or other representatives of the Company or any other Group Company;
and/or 

  

	 	(d)	to require the Employee to resign with immediate effect from any offices he holds with the Company or any other Group Company (and any related trusteeships); and/or

  

	 	(e)	to require the Employee to take any holiday which has accrued under clause 9 during the Garden Leave Period. 

The Employee shall continue to be bound by the duties set out in Clause 5 (insofar as they are compatible with being placed on garden
leave), the restrictions set out in Clause 14.2 and all duties of good faith and fidelity during the Garden Leave Period. 
  

	18.4	If the Employee is required to take garden leave under clause 18.3 the Company will during this time (where the Company has served notice to terminate his employment
Without Cause under clause 17.1(i) but not otherwise) pay to the Employee an annual incentive award equal to the lesser of (x) the target annual incentive award for the year in which notice was served and (y) the average annual incentive
awards received by the Employee in the prior three years (or if less the number of prior years in which the Employee was employed by the Company) multiplied by a fraction, the numerator of which is the number of days that the Employee was on garden
leave and the denominator of which is 365 such award to be paid on the completion of garden leave. 

  

	19.	OBLIGATIONS UPON TERMINATION OF EMPLOYMENT; CERTAIN OTHER TERMINATIONS 

 

	19.1	Upon the termination of his employment hereunder for whatever reason the Employee shall: 

 

	 	(a)	forthwith tender his resignation as a Director of any Group Company without compensation, but without prejudice to any other rights which he may have under this
Agreement. To secure his obligation under this Agreement the Employee irrevocably appoints the Company to be his attorney in his name and on his behalf to sign any documents and do any things necessary to give effect thereto, if the Employee shall
fail to sign or do the same himself; 

	 	(b)	deliver up to the Company all keys, credit cards, correspondence, documents, specifications, reports, papers and records (including any computer materials such as discs
or tapes) and all copies thereof and any other property (whether or not similar to the foregoing or any of them) belonging to the Company or any other Group Company which may be in his possession or under his control, and (unless prevented by the
owner thereof) any such property belonging to others which may be in his possession or under his control and which relates in any way to the business or affairs of the Company or any other Group Company or any supplier, agent, distributor or
customer of the Company or any other Group Company, and he shall not without written consent of the Board retain any copies thereof; 

  

	 	(c)	if so requested send to the Company Secretary a signed statement confirming that he has complied with Clause 19.1(b); and 

 

	 	(d)	not at any time make any untrue or misleading oral or written statement concerning the business and affairs of the Company or any other Group Company or represent
himself or permit himself to be held out as being in any way connected with or interested in the business of the Company or any other Group Company (except as a former employee for the purpose of communicating with prospective employers or complying
with any applicable statutory requirements). 

  

	19.2	 In the event of a termination of Employee’s employment hereunder by the Employee with Good Reason or by the Company without Cause (other than by
reason of death), the Employee shall be entitled to (a) salary at his Salary Rate through the date in which his termination occurs; (b) the lesser of (x) the target annual incentive award for the year in which the Employee’s
termination occurs, and (y) the average of the annual incentive awards received by the Employee in the prior three years (which in the case of annual incentive awards paid to the Employee under the Original Agreements in force before the date
of this Agreement shall be pro-rated to 80% of the amount paid to reflect the change in time commitment by the Employee from the date of this Agreement), multiplied by a fraction, the numerator of which is the number of days that the Employee was
employed during the applicable year and the denominator of which is 365; (c) subject to Clause 19.3 below, the sum of (x) half of the Employee’s highest Salary Rate during the term of this Agreement and (y) half of the average
bonus under the Company’s annual incentive plan actually earned by the Employee during the prior three years (which in the case of annual incentive awards paid to the Employee under the Original Agreements in force before the date of this
Agreement shall be pro-rated to 80% of the amount paid to reflect the change in time commitment by the Employee from the date of this Agreement)) (the sum of (x) and (y) hereafter referred to as the “Severance Payment”),
and (d) the unpaid balance of all previously earned cash bonus and other incentive awards with respect to performance periods which have been completed, but which have not yet been paid. In the event that the Company terminates the
Employee’s employment without Cause under the provisions of Clause 17.1(ii) the parties acknowledge that the Severance Payment will be inclusive of the Employee’s rights to be paid in lieu of the 6 months’ notice period to which he is
entitled under that Clause. In the event of a termination of the Employee’s employment hereunder by the Employee with Good Reason or by the Company without 

	 	
Cause in advance of March 2015, the Company will, at its election, either (i) subject to approval by the Aspen Group Compensation Committee, procure that any outstanding long term incentive
awards granted to the Employee in 2012 and prior years (the “Pre-2012 LTIP Awards”) will continue (subject to satisfaction of relevant performance tests) to be eligible for vesting on their due vesting date, or (ii) make an
additional cash payment to the Employee at current fair market value to reflect compensation for the loss of any Pre-2012 LTIP Awards forfeited in accordance with the rules of the Aspen Insurance Holdings 2003 Share Incentive Plan. All amounts
prescribed by this Clause 19.1 shall be payable in a lump sum in cash within 30 days after his termination 

  

	19.3	In the event that the Employee’s employment is terminated by the Company without Cause under the provisions of Clause 17.1 (i) and the Company exercises all
or any of its rights under Clause 18.3 during the 12 months’ notice period, the Severance Payment shall be reduced by a sum equal to the total salary and bonus payments received by the Employee during the Garden Leave Period.

  

	19.4	Upon any termination of employment, the Employee shall be entitled to (a) any expense reimbursement due to him and (b) other benefits (if any) in accordance
with the applicable plans and programs of the Company. 

  

	19.5	In the event of any termination of employment under this Agreement, the Employee shall be under no obligation to seek other employment and there shall be no offset
against amounts due the Employee under this Agreement on account of any remuneration attributable to any subsequent employment that he may obtain. 

  

	20.	EFFECT OF TERMINATION OF THIS AGREEMENT 

 The expiry or termination of this Agreement however arising shall not operate to affect any of the provisions hereof which are expressed to operate or have effect thereafter and shall not prejudice the
exercise of any right or remedy of either party accrued beforehand. 
  

	21.	GENERAL RELEASE 

Notwithstanding any provision herein to the contrary, prior to payment of any amount pursuant to Clauses 15.2 and 19.2, the Employee shall
execute a valid general release, in the form attached hereto (except to the extent that the Company considers that a change in law or any current practice existing at the date of termination requires a modification to such release), pursuant to
which the Employee shall release the Group and its shareholders, directors, officers, employees and agents, to the maximum extent permitted by law, from any and all claims the Employee may have against the Group that relate to or arise out of the
Employee’s employment or termination of employment, except such claims arising under this Agreement. 
  

	22.	OTHER TERMS AND CONDITIONS 

  

	22.1	The Employee’s period of continuous employment which began on 1st July 1989 shall be recognised by the Company. 

 

	22.2	 The Company shall maintain a directors’ and officers’ liability insurance policy covering the Employee which is no less favorable than the
policy covering other senior Employee officers of the Company. In addition, the Company expressly acknowledges that the 

	 	
Employee is in the class of individuals entitled to be an “Indemnified Person” (as such term is defined in the Amended and Restated Bye-Laws of the Company (the
“Bye-Laws”)). As such, the Employee shall be entitled to the greatest of any and all protections regarding indemnity, insurance and advancement and reimbursement of expenses provided under the Bye-Laws as in existence on the date
hereof, the directors’ and officers’ policy described above, or such greater protection as may be provided under applicable law, provided, however, that if the Bye-Laws are amended after the date hereof, and, as amended, they provide
greater benefits than the existing Bye-Laws, the Employee shall be entitled to such greater benefits. 

  

	22.3	In the event that a new Bermuda work permit is required to enable the Employee to take up his new position, and the Company is unable to obtain such a permit (other
than by reason of an action by the Employee) within 6 months after the Employee was scheduled to take on his new position, then the Company will use reasonable efforts to provide the Employee with alternative employment in Bermuda or the United
Kingdom with the Company or one of its Affiliates at a level commensurate with the proposed role of Chairman, AIL. If the Company is unable to do so, then the Employee’s employment with the Company will be terminated by mutual agreement, but
the Employee will receive the financial benefits of this contract on the same terms as if he had been terminated without Cause. 

  

	23.	NOTICES 

 Any notice to be
given hereunder shall be in writing. Notice to the Employee shall be sufficiently served by being delivered personally to him or be being sent by first class post addressed to him at his usual or last known place of residence, Notice to the Company
shall be sufficiently served by being delivered to the Company Secretary or by being sent by first class post to the registered office of the Company. Any notice if so posted shall be deemed served upon the third day following that on which it was
posted. 
  

	24.	PREVIOUS AND OTHER AGREEMENTS 

 This Agreement shall take effect in substitution for all previous agreements and arrangements (whether written, oral or implied) between the Company and the Employee (including, without limitation, the
Original Agreement) relating to his employment which shall be deemed to have been terminated by mutual consent with effect from the commencement of this Agreement. 
  

	25.	ENTIRE AGREEMENT/AMENDMENT 

This Agreement contains the entire understanding of the parties with respect to the employment of the Employee by the Company. There are
no restrictions, agreements, promises, warranties, covenants or undertakings between the parties with respect to the subject matter herein other than those expressly set forth herein. This Agreement may not be altered, modified, or amended except by
written instrument signed by the parties hereto. 
  

	26.	ASSIGNMENT 

 This
Agreement, and all of the Employee’s rights and duties hereunder, shall not be assignable or delegable by the Employee. Any purported assignment or delegation by the 

 
Employee in violation of the foregoing shall be null and void ab initio and of no force and effect. This Agreement may be assigned by the Company to a person or entity that is the successor in
interest to substantially all of the business operations of the Company. Upon such assignment, the rights and obligations of the Company hereunder shall become the rights and obligations of such successor person or entity. Failure by such successor
of the Company to expressly assume this Agreement shall constitute an event of “Good Reason”, entitling Employee to the Benefits set forth in Clause 15 or 19, as applicable. 

 

	27.	SEVERABILITY 

 In the
event that any one or more of the provisions of this Agreement shall be or become invalid, illegal or unenforceable in any respect, the validity, legality and enforceability of the remaining provisions of this Agreement shall not be affected
thereby. 
  

	28.	SUCCESSORS/BINDING AGREEMENT 

 This Agreement shall inure to the benefit of and be binding upon personal or legal representatives, executors, administrators, successors, heirs, distributees, devisees and legatees of the parties hereto.

  

	29.	CO-OPERATION 

 During
employment by the Company and thereafter, the Employee shall provide his reasonable co-operation in connection with any action or proceeding (or any appeal from any action or proceeding) that relates to events occurring during the Employee’s
employment; provided, however, that after the Employee’s employment by the Company has ended, (i) any request for such co-operation shall accommodate the demands of the Employee’s then existing schedule and (ii) if any such
request will involve more than a de minimis amount of the Employee’s time, the Employee shall be entitled to reasonable compensation therefor. 
  

	30.	GOVERNING LAW 

 English
law shall apply to this Agreement. 
  

	31.	COUNTERPARTS 

 This
Agreement may be signed in counterparts, each of which shall be an original, with the same effect as if the signatures thereto and hereto were upon the same instrument. 

 IN WITNESS whereof this Agreement has been duly executed and delivered as a deed the day and year first
before written. 
 SIGNED as a Deed 

and DELIVERED by 
 /s/ Julian Cusack 
 JULIAN MICHAEL CUSACK 
 in the presence of: 
  

			
	 Witness Signature:
	 	/s/ Amy Malley
	 Witness Name:
	 	Amy Malley
	 Witness Address:
	 	
	 Witness Occupation:
	 	

  

			
	  

	
	ASPEN INSURANCE UK SERVICES LIMITED
		
	By:	 	 /s/ Amy Malley

		 	Name: Amy Malley
		 	Title: HR Director

 DATED
                     
 ASPEN
INSURANCE UK SERVICES LIMITED 
 and 
 JULIAN MICHAEL CUSACK 
  

 
 SEVERANCE
AGREEMENT 
  
  

 THIS AGREEMENT is made as of the      day of
                     [20[  ]] 

BETWEEN: 
  

	(1)	ASPEN INSURANCE UK SERVICES LIMITED (Registered in England No. 1184193), 30 Fenchurch St, London, EC3M 3BD, England (the “Company”); and

  

	(2)	JULIAN MICHAEL CUSACK of Baywatch, 8 Williamsville Drive, Southampton, Bermuda (hereinafter referred to as the “Employee”).

 IT IS AGREED AS FOLLOWS: 
  

	1.	INTERPRETATION 

  

	1.1	In this Agreement: 

  

			
	“Affiliate”	  	means any entity directly or indirectly controlling, controlled by, or under common control with the Company; or any other entity designated by the Board in which the Company or an
Affiliate has an interest.
		
	“Board”	  	means the Board of Directors of the Company from time to time;
		
	“Group”	  	means the Company and its Affiliates (and “Group Company” means the Company or any one of its Affiliates).;
		
	“Holdings”	  	means Aspen Insurance Holdings Limited, a Bermuda limited company, the ultimate holding company of the Company and its Affiliates;
		
	“Option Agreement”	  	means the nonqualified share option agreement entered into by the Employee and the Company on 20 August 2003; and
		
	“Service Agreement”	  	shall mean the service agreement entered into between the Employee and the Company dated
[                    ], as subsequently amended.

  

	2.	TERMINATION DATE 

 The
Employee’s employment with the Company [will end][ended] on [date] (the “Termination Date”). 

	3.	PAYMENT OF SALARY ETC 

The Company will continue to provide the Employee with his salary and all other contractual benefits up to the Termination Date in the
normal way. Within 14 days of the Termination Date the Company will also pay the Employee in respect of his accrued but untaken holiday (less such deductions for income tax and national insurance as are required by law). 

 

	4.	TERMINATION SUMS 

 Subject
to the Employee agreeing to all of the conditions set out below, and receipt by the Company of a copy of this Agreement signed by the Employee and the attached certificate signed by the Employee’s legal adviser, the Company will pay the
Employee the following sums: 
  

	 	(i)	£[appropriate figure to be inserted] in respect of the Employee’s entitlement to an annual incentive award for the year in which the termination of
the Employee’s employment with the Company occurs, as calculated in accordance with Clause 19.2 (b) of the Service Agreement; 

  

	 	(ii)	the sum of £[appropriate figure to be inserted] in respect of the Employee’s entitlement to a Severance Payment, as calculated and defined in
accordance with Clauses 19.2(c) and 19.3 of the Service Agreement; and 

  

	 	(iii)	the sum of £[appropriate figure to be inserted] in respect of the Employee’s entitlement to the unpaid balance of all previously earned cash bonus and
other incentive awards with respect to performance periods which have been completed as at the Termination Date but not yet paid, as calculated in accordance with Clause 19.2(d) of the Service Agreement. 

The sums set out in (i) to (iii) above will be subject to such deductions for income tax and national insurance as are required
by law and will be paid to the Employee within [14] days of the date of signature by him of this Agreement and signature by his legal adviser of the attached certificate. Payment will be made by transfer to the Employee’s bank account.

  

	5.	SHARE OPTIONS 

 [The
Company confirms that: 
  

	 	(a)	with respect to share options issued under the Option Agreement; notwithstanding any provision in the Option Agreement to the contrary, the Shares underlying the Time
Option (as defined in the Option Agreement) vested and became exercisable on 31 December 2006; and it is agreed that the Shares underlying the Performance-Accelerated Option (as defined in the Option Agreement) that remain unvested at the date
of this Agreement shall continue to vest and become exercisable in accordance with the provisions of clause 2(b) of the Option Agreement notwithstanding the termination of the Employee’s employment; and 

 

	 	(b)	 with respect to other share options, the extent to which share options held by the Employee as at the Termination Date shall be exercisable following
the Termination Date will be determined solely in accordance with terms of the 

	 	
agreements under which such share options were granted.] or [Other than in relation to share options granted to the Employee in 2004 and 2005, the Company confirms that all share options granted
to the Employee have vested and will remain exercisable for the remainder of their terms.]1 

  

	6.	WAIVER OF CLAIMS 

 The
Employee accepts the terms set out in this Agreement in full and final settlement of all and any claims that he has or may have against the Company, the Board, Holdings or any other Group Company or any of its or their current or former
shareholders, directors, officers, employees or agents, whether contractual (whether known or unknown, existing now or in the future), statutory or otherwise, arising out of or in connection with his employment with the Company or the termination of
his employment and his directorship of the Company and any Group Company or his resignation therefrom. The Employee also agrees to waive irrevocably and release the Company, the Board and all Group Companies (and all of its or their current or
former shareholders, directors, officers, employees or agents) from and against any claims whether contractual (whether known or unknown, existing now or in the future), statutory or otherwise, arising out of or in connection with his employment
with the Company or the termination of his employment and his directorship of the Company and any Group Company or his resignation therefrom. This waiver shall not apply in relation to any claim relating to his pension rights that have accrued up to
the Termination Date. 
  

	7.	CONFIRMATION OF NO BREACHES 

 The Employee confirms and warrants to the Company that he has not at any time during his employment committed a fundamental breach of the terms of the Service Agreement. 

 

	8.	SATISFACTION OF STATUTORY CONDITIONS 

 The Employee is aware of his rights under the Employment Act 2000 and the Human Rights Amendment Act 1987 and has informed the Company of any and all claims that he might seek to bring arising from his
employment or termination of employment. This agreement relates to his claims under the Employment Act 2000 and the Human Rights Amendment Act 1987. 
 Second alternative to be used in the event of qualifying termination in connection with a Change of Control under Clause 15.2 of the Service Agreement. 

 

	9.	RESIGNATION OF DIRECTORSHIP 

 At the same time as executing this Agreement the Employee will resign with immediate effect from his directorship of the Company and from all directorships and offices held with other Group Companies (and
all related trusteeships) by signing and delivering the attached letters of resignation. 
  

	10.	POST-TERMINATION RESTRAINTS 

 The Employee acknowledges that the provisions of Clause 11 (Confidentiality) and Clause 14 (Restrictive Covenants) of the Service Agreement will (to the extent that they are applicable in the
circumstances of the termination of the Employee’s employment with the Company) remain in full force and effect notwithstanding the termination of his employment. 

	11.	RETURN OF COMPANY PROPERTY 

Before any payment under Clause 4 above is made, the Employee will, in accordance with Clause 19.1(b) of the Service Agreement, deliver up
to the Company all vehicles, keys, credit cards, correspondence, documents, specifications, reports, papers and records (including any computer materials such as discs or tapes) and all copies thereof and any other property (whether or not similar
to the foregoing or any of them) belonging to the Company or any other Group Company which may be in his possession or under his control, and (unless prevented by the owner thereof) any such property belonging to others which may be in his
possession or under his control and which relates in any way to the business or affairs of the Company or any other Group Company or any supplier, agent, distributor or customer of the Company or any other Group Company, and he confirms that he has
not retained any copies thereof. 
  

	12.	CONFIDENTIALITY 

 Save by
reason of any legal obligation or to enforce the terms of this letter, the parties will not: 
  

	 	(a)	disclose the existence or terms of this Agreement to anyone (other than to their professional advisers, the relevant tax authorities or any other competent authority or
in the case of the Employee, to his spouse); 

  

	 	(b)	directly or indirectly disseminate, publish or otherwise disclose (or allow to be disseminated, published or otherwise disclosed) by any means (whether oral, written or
otherwise) or medium (including without limitation electronic, paper, radio or television) any information directly or indirectly relating to the termination of the Employee’s employment; or 

 

	 	(c)	make any derogatory or disparaging comments about the other or in the case of the Employee in relation to the Company, any Group Company or any of its or their
shareholders, directors, officers, employees or agents. 

  

	13.	NO ADMISSION OF LIABILITY 

This agreement is made without any admission on the part of the Company or any Group Company that it has or they have in any way breached
any law or regulation or that the Employee has any claims against the Company or any Group Company. 
  

	14.	TAX INDEMNITY 

 The
Employee hereby agrees to be responsible for the payment of any tax and employee’s national insurance contributions imposed by any competent taxation authority in respect of any of the payments and benefits provided under this Agreement (other
than for the avoidance of doubt, any tax and/or employee’s national insurance contributions deducted or withheld by the Company in paying the sums to the Employee). The Employee further agrees to indemnify the Company and all Group Companies
and keep them indemnified on an ongoing basis against any claim or demand which is made by any competent 

 
taxation authority against the Company or any Group Company in respect of any liability of the Company or any Group Company to deduct an amount of tax or an amount in respect of tax or any
employee’s national insurance contributions from the payments made and benefits provided under this Agreement, including any related interest or penalties imposed by any competent taxation authority. 

 

	15.	ENTIRE AGREEMENT 

 This
letter sets out the entire agreement between the Employee and the Company and, save as set out in Clauses 5 and 10 above, supersedes all prior arrangements, proposals, representations, statements and/or understandings between the Employee, the
Company and any Group Company. 
  

	16.	APPLICABLE LAW 

 This
agreement is subject to English law and the exclusive jurisdiction of the Bermuda courts. 
  

	
	  

	Julian Michael Cusack
	
	  

	dated
	
	  

	For and on behalf of ASPEN INSURANCE UK SERVICES LIMITED
	
	  

	dated

 To the board of Directors 
 [Relevant Aspen company] 
 [date] 

Dear Sirs 
 [xxx] (the “Company”)

 I hereby irrevocably and unconditionally resign from the office of Director of the Company with immediate effect, and I acknowledge and
confirm that I have no claim of whatsoever kind outstanding for compensation or otherwise against the Company, its servants, officers, agents or employees in respect of the termination of my appointment. 

Yours faithfully 
  

			
	SIGNED as a DEED	 	)
	and DELIVERED	 	)
	by JULIAN MICHAEL CUSACK	 	)
	in the presence of:	 	)
		
	Witness signature:	 	
		
	Witness Name:	 	
		
	Witness address:

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