DATED OCTOBER 20, 2014 ASPEN BERMUDA LIMITED (1) and JAMES RICHARD FEW (2) ____________________________________________________ SEVERANCE AGREEMENT ____________________________________________________ Willkie Farr & Gallagher (UK) LLP City Point 1 Ropemaker Street London EC2Y 9AW Tel: +44 (0)20 3580 4700 Fax: +44 (0)20 3580 4800 www.willkie.com

ASPEN BERMUDA LIMITED (formerly ASPEN INSURANCE LIMITED), incorporated in the Islands of Bermuda whose registered office is at Canon’s Court, 2^nd Floor, 22 Victoria Street, Hamilton HM12, Bermuda (the “Company”); and

JAMES RICHARD FEW of Winslow, 34 Harbour Road, Paget PG02, Bermuda (hereinafter referred to as the “Executive”).

INTERPRETATION

In this Agreement:

TERMINATION DATE

PAYMENT OF SALARY ETC

TERMINATION SUMS

an amount equal to the formulaic annual incentive award derived from the Company’s annual incentive award funding formula for the Executive’s role in respect of the fiscal year ending on December 31, 2014, applied in the same manner as applied to active executive employees of the Company and calculated 50% by reference to Group Return on Equity versus 2014 plan performance and 50% by reference to the average Return on Equity versus 2014 plan performance of Other Property, Property Catastrophe (including Aspen Capital Markets), Casualty Re and Specialty Re, in each case without the application of any negative discretion, such amount payable at the same time as annual incentive awards for the fiscal year ending on December 31, 2014, are paid to executives of the Company, such date to be no later than the March 15, 2015 monthly payroll date;

$600,000 in respect of the Executive’s entitlement to the severance payment calculated and defined in accordance with Clauses 19.2(c)(x) and 19.3 of the Service Agreement, such amount payable by no later than the March 15, 2015 monthly payroll date; and

an amount equal to the severance payment calculated and defined in accordance with Clauses 19.2(c)(y) and 19.3 of the Service Agreement, except that the three-year period used to calculate the average annual incentive award will be based on the fiscal years ending on December 31, 2012, 2013 and 2014, with the annual incentive award for the fiscal year ending on December 31, 2014, calculated in accordance with subclause (i) above, such amount payable at the same time as annual incentive awards for the fiscal year ending on December 31, 2014, are paid to executives of the Company, such date to be no later than the March 15, 2015 monthly payroll date (the amounts set forth in subclauses (i), (ii) and (iii) of this Clause 4 are collectively referred to herein as the “Severance Payments”).

GARDEN LEAVE

not to attend at the offices of the Company or any other Group Company;

not to carry out any duties;

(other than as qualified in the paragraph immediately following subclause (iv) below to allow for reasonable social interaction) not to communicate or deal with any employees, agents, consultants or customers of the Company or any other Group Company, including not dealing with brokers or other intermediaries with whom the Company does business and not attending at any industry events, whether formal or social in nature; and

to maintain total confidentiality as to the terms of or the circumstances surrounding his departure from the Company, except to his immediate family and attorney, provided each such person agrees to keep this fully confidential.

EQUITY AWARDS

the 11,846 outstanding time-based restricted share units scheduled to vest on the next applicable vesting date will vest on their regularly scheduled vesting dates as follows: 4,249 restricted share units will vest on February 8, 2015; 3,310 restricted share units will vest on February 11, 2015; and 4,287 restricted share units will vest on April 25, 2015;

of the 37,194 performance shares granted to the Executive in 2012 (the “2012 Performance Shares”), the 12,076 performance shares which are “banked” as of the date hereof will vest on their regularly scheduled vesting date following the filing by Aspen Insurance Holdings Limited of its Annual Report on Form 10-K

of the remaining 2012 Performance Shares, 12,398 performance shares, forming the last tranche of the 2012 Performance Shares, will continue to be eligible for vesting on the 2015 Vesting Date, subject to the application of the 2014 testing conditions of such performance shares;

of the 29,669 performance shares granted to the Executive in 2013 (the “2013 Performance Shares”), the 3,126 performance shares which are “banked” as of the date hereof will vest on their regularly scheduled vesting date following the filing by Aspen Insurance Holdings Limited of its Annual Report on Form 10-K for the fiscal year ended December 31, 2015 (such filing date, the “2016 Vesting Date”); and

of the 2013 Performance Shares, 9,889 performance shares, forming the second tranche of the 2013 Performance Shares, will continue to be eligible for vesting on the 2016 Vesting Date, subject to the application of the 2014 testing conditions of such performance shares.

WAIVER OF CLAIMS

The Executive 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 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. The Executive 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

As a condition to his receipt of the payments and benefits described in Clauses 4 and 6 above, the Executive agrees to execute and deliver to the Company the Supplemental Release Agreement attached as Exhibit A hereto promptly following the Termination Date, but in no event later than five (5) days following the Termination Date.

The Company (acting for itself and as agent for all other Group Companies) confirms to the Executive that neither it nor any other Group Company has any claim or right of action against the Executive (whether known or unknown, existing now or in the future) arising out of or in connection with his holding office with (as director or otherwise), or being employed by, any Group Company or the termination of any such office or employment. To the extent that any such claim or right of action exists or may exist, the Company (acting for itself and as agent for all other Group Companies) irrevocably: (a) waives any such claim or right of action; and (b) releases the Executive from any such liability; provided, that the claims released pursuant to this Clause 7(iii) shall not include: (1) claims with respect to (x) the right to enforce this Agreement or (y) the memorandum and articles of association, certificate of incorporation or by-laws of the Company or any other Group Company, (2) claims that are based upon any of the Executive’s acts or omissions that involve fraud, deceit, misappropriation, embezzlement, theft, breach of fiduciary duty, gross negligence or intentional misconduct, or arising out of facts that constitute a violation of law, (3) cross-claims in any shareholder derivative lawsuit, (4) any rights of the Company Group arising under the Sarbanes-Oxley Act of 2002 or any written policy in effect on the Termination Date that requires the disgorgement of incentive compensation as the result of an accounting restatement due to noncompliance with financial reporting requirements, or (5) any claims that cannot be waived by law. The Company warrants and represents to the Executive that he has resigned validly from all directorships and offices he held with any Group Company.

During the six (6) year period following the Termination Date, the Company will maintain directors’ and officers’ liability insurance for the benefit of the Executive, to the same extent as maintained for other senior executives of the

CONFIRMATION OF NO BREACHES

SATISFACTION OF STATUTORY CONDITIONS

POST-TERMINATION RESTRAINTS

CLAWBACK

LEGAL ADVICE AND EXPENSES

RETURN OF COMPANY PROPERTY

CONFIDENTIALITY

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

make any derogatory or disparaging comments about the Company, any Group Company or any of its or their shareholders, directors, officers, employees or agents.

those senior Group and/or Company employees with knowledge of this Agreement (including, without limitation, Aspen’s current Chief Executive Officer and Group General Counsel) will not: (x) disclose its terms or existence to others within or outside the Company (except as required by law; in particular, but without limitation, in the circumstances provided for in the paragraph immediately following subclause (b) below); (y) 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 Executive’s employment, other than in a manner consistent with the Company’s press release, dated September 5, 2014; or (z) make any derogatory or disparaging comments about the Executive; and

Aspen’s Group General Counsel (or his successor) will respond to any requests for an oral reference.

NO ADMISSION OF LIABILITY

TAX INDEMNITY

TAX RESIDENCY

ENTIRE AGREEMENT

APPLICABLE LAW

On or about October 20, 2014, I entered into a Severance Agreement (the “Agreement”) with Aspen Bermuda Limited (the “Company”);

Pursuant to Clause 7(ii) of the Agreement, I am required to execute this Supplemental Release Agreement (this “Release”) as a condition of receiving the payments and benefits described in Clauses 4 and 6 of the Agreement;

By signing this Release, I acknowledge and agree that the payment(s) and other benefits provided (or to be provided) pursuant to the Agreement are in full discharge of any and all liabilities and obligations of the Company or any other Group Company to me, monetarily or with respect to employee benefits or otherwise;

By signing this Release, I, on behalf of myself, my duly appointed legal representatives in the event of my legal incapacity (for the avoidance of doubt, excluding Covington & Burling LLP), executors, heirs and assigns, reaffirm each and every provision of the Agreement as of the date below and specifically acknowledge that I am waiving any and all claims of any nature or kind that I may have against the Company (whether known or unknown to me) that accrued or could have accrued between the time that I signed the Agreement and the date set forth below.

I acknowledge and reaffirm my continuing obligations under Clause 10 of the Agreement.

Clause 19 of the Agreement shall apply to this Release.