Section 1.

Retention of the Service Provider.

Section 2.

Term.

Section 3.

Management Consulting Services.

Section 4.

Compensation.

Section 5.

Indemnification; Limitation on Damages

Section 6.

Notices.

Section 7.

Benefits of Agreement.

Section 8.

Governing Law; Jurisdiction.

Section 9.

Headings.

Section 10.

Entire Agreement; Amendments.

Section 11.

Counterparts.

Section 12.

Waivers.

Section 13.

Severability.

Section 14.

Definitions.

Section 15.

UK Carbon Reduction Commitment (“ CRC ”) Paying Agent Authorization

By:

/s/ Mark Cloutier
Name: Mark Cloutier
Title: Group Chief Executive Officer and

By:

/s/ William Kuesel
Name: William Kuesel
Title: Vice President

(1)

ASPEN INSURANCE UK SERVICES LIMITED incorporated and registered in England and Wales with company number 04270446 whose registered office is at 30 Fenchurch Street, London, EC3M 3BD (" Company ")

(2)

ASPEN INSURANCE HOLDINGS LIMITED incorporated in the Islands of Bermuda whose registered office is at Cedar Avenue, Hamilton, Bermuda (" Aspen Holdings ");

(3)

CHARLES CHRISTOPHER O'KANE of [Address intentionally omitted] (" Executive ")

(A)

The Executive has been employed by the Company from 21 June 2002, most recently as the Chief Executive Officer under an amended and restated service agreement between the parties dated 24 September 2004 as amended on 28 October 2014.

(B)

The parties also entered into a change in control employment agreement dated 23 February 2015 setting out enhanced employment and severance terms that would come into effect for the Executive in the event that Aspen Holdings was the subject of a change in control . The proposed merger of Aspen Holdings with an affiliate of certain investment funds managed by affiliates of Apollo Global Management, LLC will amount to a change in control for the purposes of the change in control employment agreement dated 23 February 2015.

(C)

The Executive's employment with the Company terminated on 15 February 2019 by reason of mutual agreement.

(D)

The parties have entered into this agreement to record and implement the terms on which they have agreed to settle any claims that the Executive has or may have in connection with his employment or its termination or otherwise against any Group Company (as defined below) or their officers or employees whether or not those claims are, or could be, in the contemplation of the parties at the time of signing this agreement, and including, in particular, the statutory complaints that the Executive raises in this agreement.

(E)

The parties intend this agreement to be an effective waiver of any such claims and to satisfy the conditions relating to settlement agreements in the relevant legislation.

(F)

The Company and Aspen Holdings enter into this agreement for themselves and as agents and trustees for all Group Companies and they are authorised to do so. It is the parties' intention that each Group Company should be able to enforce any rights it has under this agreement, subject to and in accordance with the Contracts (Rights of Third Parties) Act 1999.

1.

INTERPRETATION

1.1

Definitions

1.2

The headings in this agreement are inserted for convenience only and shall not affect its construction.

1.3

A reference to a particular law is a reference to it as it is in force for the time being taking account of any amendment, extension, or re-enactment and includes any subordinate legislation for the time being in force made under it.

1.4

Unless the context otherwise requires, a reference to one gender shall include a reference to the other genders.

1.5

Unless the context otherwise requires, words in the singular shall include the plural and in the plural shall include the singular.

1.6

The Schedules shall form part of this agreement and shall have effect as if set out in full in the body of this agreement. Any reference to this agreement includes the Schedules.

1.7

A reference to a holding company or a subsidiary means a holding company or a subsidiary (as the case may be) as defined in section 1159 of the Companies Act 2006.

2.

ARRANGEMENTS ON TERMINATION

2.1

The Executive's employment with the Company terminated on 15 February 2019 (the " Termination Date ").

2.2

The Company has paid the Executive his salary up to the Termination Date in the usual way.

2.3

The Company has provided benefits to the Executive in the usual way up to the Termination Date.

2.4

The Company will meet the cost of professional fees, including any fees accrued at the Termination Date, for tax compliance guidance relating to company withholding and reporting obligations as a consequence of the Executive’s assignment in Bermuda and the termination of his employment. The Executive will be responsible for the cost of professional fees in relation to personal tax planning, advice and guidance together with the actual costs of UK and US tax return preparation.

2.5

The Company shall make a payment to the Executive in respect of eight (8) days' outstanding holiday, up to and including the Termination Date.

2.6

The payments and benefits in this clause 2 shall be subject to any income taxes and National Insurance contributions or equivalent that the Company is obliged by law to pay or deduct.

2.7

The Executive has submitted his expenses claims in the usual way and the Company shall reimburse the Executive for any expenses properly incurred before the Termination Date in the usual way.

2.8

The Company shall deduct from the sums due under this agreement any outstanding sums due from the Executive to any Group Company, including an overpayment of remuneration and benefits with respect to 9 working days from 18 February to 28 February 2019 (with a value of approximately USD 31,994 ).

3.

TERMINATION PAYMENTS

3.1

Subject to and conditional on the Executive complying with the terms of this agreement, the Company shall within 21 days of the Termination Date or receipt by the Company of a copy of this agreement signed by the Executive and a letter from the Adviser in the form as set out in Schedule 3, whichever is later, pay to the Executive:

(a)

the amount of USD 3,519,156 as a severance payment in accordance with the terms of the Change in Control Employment Agreement (the " Severance Payment "), such payment to include a payment in lieu of the Executive's notice period in accordance with clause 6(a)(i)(B) of the Change in Control Employment Agreement;

(b)

the amount of USD 38,590 as a pro-rated bonus for performance year 2019 in accordance with clause 6(i)(A)(5) of the Change in Control Employment Agreement;

(c)

the amount of USD 164,245 as the equivalent of the pension contributions the Executive would have received for the 12 month period following the Termination Date in accordance with clause 6(a)(iii) of the Change in Control Employment Agreement;

(d)

the amount of USD 62,690 as the equivalent cost of the private medical insurance premiums the Executive would have received for the 12 month period following the Termination Date in accordance with clause 6(iv) of the Change in Control Employment Agreement;

(e)

the amount of USD 34,275 as the equivalent cost of providing assistance to the Executive with respect to his US tax returns for tax years 2018 and 2019 and his UK tax return for tax year 2018-2019 in accordance with the terms of the International Assignment Letter;

(f)

the amount of USD 47,706 as the equivalent cost of paying for the Executive's relocation costs in accordance with the terms of the International Assignment Letter; and

(g)

the amount of USD 10,000,000 as a bonus in recognition of the Executive's contributions towards the Transaction (the " Transaction Bonus ").

3.2

The Executive acknowledges that the Executive shall be liable for any income taxes and/or National Insurance contributions or other employee social security charges arising in

3.3

Consistent with the terms of the International Assignment Letter, the Executive agrees that Aspen Holdings is entitled to ownership of all Tax Credits arising in respect of the Executive's employment with the Company, and accordingly the Executive agrees that:

(a)

the Executive shall promptly upon becoming aware that the Executive has obtained any Tax Credit in respect of the Executive's employment with the Company notify Aspen Holdings accordingly; and

(b)

the Executive shall pay an amount equal to such Tax Credit to Aspen Holdings,

4.

TREATMENT OF AWARDS

4.1

The Executive acknowledges and agrees that all share options and other equity-based awards, including restricted stock units and performance stock units, held by the Executive vested on the completion of the Transaction, with satisfaction of performance conditions determined based on either (i) the actual level of performance achieved, with respect to any performance period that had been completed or (ii) the target performance level, with respect to any performance period that had not yet been completed, and that the Executive received at the same time as other similarly situated employees of the Company received payment for their respective equity awards, a lump-sum amount in cash, without interest, equal to $42.75 for each share subject to such vested share option or equity-based award (plus any amounts in respect of accrued dividend equivalents related thereto, to the extent applicable), less any applicable tax and/or National Insurance Contributions or other social security withholdings that the Company are required by law to withhold.. The Executive acknowledges and agrees that on receipt of such cash amount, all vested and unvested awards held by him under the Aspen Insurance Holdings Limited 2013 Share Incentive Plan or any other equity plan maintained by the Group Company (collectively, the “ Omnibus Plan ”) are fully satisfied and discharged and that he has no further rights, including any right to any further grant, payment, vesting, or compensation, under any plan or award agreement.

4.2

The parties understand that the number of shares in respect of which the Executive shall receive a payment under clause 4.1 is:

5.

PENSION

6.

OUTPLACEMENT AND REPATRIATION FLIGHTS

6.1

The Company shall bear the costs (up to $40,000 plus any value added tax or equivalent) in relation to the provision of outplacement counselling to the Executive by a provider

6.2

The Company will also pay the cost of flights for the Executive and his family to return from Bermuda to either London or a city in the US. Such flights must be booked through the Company's travel agency and comply with the Company's Travel and Expense Policy.

7.

280G

7.1

Notwithstanding anything to the contrary in this agreement, the Executive acknowledges and agrees that in the event that any payment under this agreement, including any portion of the Transaction Bonus, when added to all other payments or benefits provided by any Group Company to the Executive or for his benefit (the “ Covered Payments ”), would constitute a “parachute payment” within the meaning of Section 280G(b)(2) of the US Internal Revenue Code of 1986, as amended (the “ Code ”), and would, but for this paragraph, be subject to the excise tax imposed under Section 4999 of the Code or any similar tax imposed by state or local law or any interest or penalties with respect to such taxes (collectively, the “ Excise Tax ”), then such Covered Payments shall be either:

(a)

reduced to the minimum extent necessary so that the present value of the Covered Payments will be one dollar ($1.00) less than three times the Executive's “base amount” (within the meaning of Section 280G(b)(3) of the Code) to ensure that no portion of the Covered Payments is subject to the Excise Tax (that amount, the “ Reduced Amount ”); or

(b)

payable in full if the Executive's receipt on an after-tax basis of the full amount of payments and benefits (after taking into account the applicable federal, state, local and foreign income, employment and excise taxes (including the Excise Tax)) would result in the Executive receiving an amount that is at least one dollar greater than the Reduced Amount.

7.2

If the Covered Payments are to be reduced pursuant to clause 7.1(a), the reduction shall be made reducing first any Covered Payments that are exempt from Section 409A of the Code, and then reducing any Covered Payments subject to Section 409A of the Code in the reverse order in which such Covered Payments would be paid or provided (beginning with such payment or benefit that would be made last in time and continuing, to the extent necessary, through to such payment or benefit that would be made first in time). Where two Covered Payments subject to reduction are payable at the same time, such amounts shall be reduced on a pro rata basis but not below zero. The determination as to whether any such reduction in the Covered Payments is necessary shall be made by the compensation committee of the Board in good faith. If a reduced Covered Payment is made or provided and, through error or otherwise, that Covered Payment, when aggregated with other payments and benefits from any Group Company used in determining if a “parachute payment” exists, exceeds one dollar ($1.00) less than three times the Executive's “base amount,” then the Executive shall immediately repay such excess to the applicable Group Company.

8.

LEGAL FEES

9.

WAIVER OF CLAIMS

9.1

The Executive agrees that the terms of this agreement are offered by the Company and Aspen Holdings without any admission of liability on the part of the Company or Aspen Holdings and are in full and final settlement of all and any claims or rights of action that the Executive has or may have against any Group Company or their officers or Executives whether arising out of his employment with the Company or its termination or from events occurring after this agreement has been entered into, whether under common law, contract, statute or otherwise, whether such claims are, or could be, known to the parties or in their contemplation at the date of this agreement in any jurisdiction and including, but not limited to, the claims specified in Schedule 2 (each of which is waived by this clause).

9.2

The waiver in clause 9.1 shall not apply to the following:

(a)

any claims by the Executive to enforce this agreement;

(b)

any claims as a shareholder of the Company;

(c)

any claims for indemnification or coverage under any directors’ and officers’ liability insurance policy of any Group Company;

(d)

claims in respect of personal injury of which the Executive is not aware and could not reasonably be expected to be aware at the date of this agreement (other than claims under discrimination legislation); and

(e)

any claims in relation to accrued entitlements under the Pension Scheme.

9.3

The Executive warrants that:

(a)

before entering into this agreement he received independent advice from the Adviser as to the terms and effect of this agreement and, in particular, on its effect on his ability to pursue any complaint before an employment tribunal or other court;

(b)

the Adviser has confirmed to the Executive that they are a solicitor holding a current practising certificate and that there is in force a policy of insurance covering the risk of a claim by the Executive in respect of any loss arising in consequence of their advice;

(c)

the Adviser shall sign and deliver to the Company a letter in the form attached as Schedule 3 to this agreement;

(d)

before receiving the advice the Executive disclosed to the Adviser all facts and circumstances that may give rise to a claim by the Executive against any Group Company or their officers or employees;

(e)

the only claims that the Executive has or may have against any Group Company or its officers or Executives (whether at the time of entering into this agreement or in the future) relating to his employment with the Company or its termination are specified in clause 9.1; and.

(f)

the Executive is not aware of any facts or circumstances that may give rise to any claim against any Group Company or their officers or employees other than those claims specified in clause 9.1.

9.4

The Executive acknowledges that the conditions relating to settlement agreements under section 147(3) of the Equality Act 2010, section 288(2B) of the Trade Union and Labour Relations (Consolidation) Act 1992, section 203(3) of the Employment Rights Act 1996, regulation 35(3) of the Working Time Regulations 1998, section 49(4) of the National Minimum Wage Act 1998, regulation 41(4) of the Transnational Information and Consultation etc. Regulations 1999, regulation 9 of the Part-Time Workers (Prevention of Less Favourable Treatment) Regulations 2000, regulation 10 of the Fixed-Term Executives (Prevention of Less Favourable Treatment) Regulations 2002, regulation 40(4) of the Information and Consultation of Executives Regulations 2004, paragraph 13 of the Schedule to the Occupational and Personal Pension Schemes (Consultation by Employers and Miscellaneous Amendment) Regulations 2006, regulation 62 of the Companies (Cross Border Mergers) Regulations 2007 and section 58 of the Pensions Act 2008 have been satisfied.

9.5

The waiver in clause 9.1 shall have effect irrespective of whether or not, at the date of this agreement, the Executive is or could be aware of such claims or have such claims in his express contemplation (including such claims of which the Executive becomes aware after the date of this agreement in whole or in part as a result of new legislation or the development of common law or equity).

9.6

The Executive agrees that, except for the payments and benefits provided for in this agreement, and subject to the waiver in clause 9.1, he shall not be eligible for any further payment from any Group Company relating directly or indirectly to his employment or its termination and he expressly waives any right or claim that he has or may have to payment of bonuses, any benefit or award programme, under any share plan operated by any Group Company or any stand-alone share incentive arrangement, or to any other benefit, payment or award he may have received had his employment not terminated, including without limitation any such benefit, payment or award under the Change in Control Employment Agreement or the Omnibus Plan.

11.

COMPANY PROPERTY AND INFORMATION

11.1

The Executive warrants as at the date of this agreement, that he has returned to the Company and/or Aspen Holdings:

(a)

all Confidential Information and Copies;

(b)

subject to clause 11.2 below, all property belonging to the Company and/or Aspen Holdings in satisfactory condition including (but not limited to) any car (together with the keys and all documentation relating to the car), fuel card, company credit card, keys, security pass, identity badge, pager, lap-top computer or fax machine; and

(c)

all documents and copies (whether written, printed, electronic, recorded or otherwise and wherever located) made, compiled or acquired by him during his employment with the Company or relating to the business or affairs of any Group Company or their business contacts,

(a)

use any Confidential Information; or

(b)

make or use any Copies; or

(c)

disclose any Confidential Information to any person, company or other organisation whatsoever.

17.

VARIATION

18.

THIRD PARTY RIGHTS

19.

GOVERNING LAW

20.

JURISDICTION

21.

SUBJECT TO CONTRACT AND WITHOUT PREJUDICE

22.

COUNTERPARTS

1.

I hereby resign with effect from the date of this letter (the " Termination Date ") from my office as a director of each of the Companies, any position of office of the Companies, and any trusteeship, any committee membership and any fiduciary position of the Companies and any of its benefit plans (the " Officer Positions ").

2.

I acknowledge that:

2.1

I have no claims or rights of action arising from arising from the holding of the Officer Positions or their termination, whether under common law, contract, statute or otherwise, whether or not such claims are, or could be, known to the me or in my contemplation at the Termination Date in any jurisdiction; and

2.2

there is no agreement or arrangement outstanding under which the Companies have or could have any actual or contingent obligation to me or to any person connected with me; and

2.3

to the extent that any such claim, obligation or sum exists or may exist as at the date of this letter, I irrevocably and unconditionally waive such claim, obligation or sum and all rights of action I may have against the Companies so far as is possible under the applicable law of each Company.

3.

For the purposes of this letter a person shall be deemed to be connected with me if that person is so connected within the meaning of section 1122 of the Corporation Tax Act 2010 (or any equivalent legislation outside the UK).

4.

This letter and any disputes or claims (including non-contractual disputes or claims) arising out of or in connection with it or its subject matter or formation shall be governed by and construed in accordance with the law of England and Wales. The courts of England and Wales shall have exclusive jurisdiction to settle any dispute or claim (including non-contractual disputes or claims) arising out of or in connection with this letter or its subject matter or formation.

5.

This document has been executed as a deed and is delivered and takes effect on the date stated at the beginning of it.

1.

Claims:

(a)

for breach of contract or wrongful dismissal;

(b)

for unfair dismissal, under section 111 of the Employment Rights Act 1996;

(c)

in relation to the right to a written statement of reasons for dismissal, under section 93 of the Employment Rights Act 1996;

(d)

for a statutory redundancy payment, under section 163 of the Employment Rights Act 1996;

(e)

in relation to an unlawful deduction from wages or unlawful payment, under section 23 of the Employment Rights Act 1996;

(f)

for unlawful detriment, under section 48 of the Employment Rights Act 1996 or section 56 of the Pensions Act 2008;

(g)

in relation to written employment particulars and itemised pay statements, under section 11 of the Employment Rights Act 1996;

(h)

in relation to guarantee payments, under section 34 of the Employment Rights Act 1996;

(i)

in relation to suspension from work, under section 70 of the Employment Rights Act 1996;

(j)

in relation to working time or holiday pay, under regulation 30 of the Working Time Regulations 1998;

(k)

for direct or indirect discrimination, harassment or victimisation related to age, under section 120 of the Equality Act 2010 [and/or under regulation 36 of the Employment Equality (Age) Regulations 2006];

(l)

in relation to the right to be accompanied under section 11 of the Employment Relations Act 1999;

(m)

in relation to personal injury, of which the Employee is or ought reasonably to be aware at the date of this agreement;

(n)

for harassment under the Protection from Harassment Act 1997;

(o)

for failure to comply with obligations under the Human Rights Act 1998;

(p)

for failure to comply with obligations under the Data Protection Act 1998; and

(q)

arising as a consequence of the United Kingdom's membership of the European Union.

1.

I, [NAME] of [FIRM], whose address is [ADDRESS], am [a Solicitor of the Senior Courts of England and Wales who holds a current practising certificate OR AMEND AS APPLICABLE].

2.

I have given Mr. O’Kane legal advice on the terms and effect of the Agreement and, in particular, its effect on his ability to pursue the claims specified in Schedule 2 of the Agreement.

3.

I gave the advice to Mr. O’Kane as a relevant independent adviser within the meaning of the above acts and regulations referred to at clause 9.4.

4.

There is now in force (and was in force at the time I gave the advice referred to above) a policy of insurance or an indemnity provided for members of a profession or professional body covering the risk of claim by Mr. O’Kane in respect of loss arising in consequence of the advice I have given him.

1.

POST-TERMINATION OBLIGATIONS

1.1

Fo r the purpose of this Clause:

1.2

The Executive covenants with the Company that he will not in connection with the carrying on of any business in competition with the Business for the period of 12 months after the Termination Date without the prior written consent of the Board either alone or jointly with or on behalf of any person directly or indirectly:

(a)

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 Re s tricted Person ;

(b)

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

1.3

T he E xecutive further covenants that he will not in connection with the carrying on of any busines s in competition with the Business for the further period of 12 months following the first anniversary of the Termination Date , without the prio r written consent of the Board, either a lo ne or jointly with or on behalf of any person directly or indirectly (a) canvass, solicit or approach or cause to be canvass ed 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; or (b) solicit or entice away or endeavour to solicit or entice away from the Company or any other Group Company any Key Employee.

1.4

The Executive further covenants with the Company that he will not, for the period of 1 2 months after the Termination Date , be employed , engaged, interested in or concern e d 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 competit io n with the Business;

1.5

T he covenants contained in Clauses 1.2, 1.3 and 1.4 are intended to be separate and severable and enforceable as such. It is expressly understood and agreed that although the Executive and the Company consider the restrictions contained in this clause 1 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 Agreem e nt is an unenforceable restriction against the Executive, the provisions of this Agreem e nt shall not be rendered void but shall be deemed amended to apply as to such maximum t ime 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 r estriction 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.

1.6

T he Executive acknowledges and agrees that the Company's remedies at law for a breach of any of the provisions of this clause 1 would be inadequate and the Company would suffer irreparable damages as a result of such breach. In recognition of this fact , the Executive agrees that, in the event of suc h a breach, in addition to any remedies at law, the Company, without posting any bond, shall be entitled to obtain equitabl e relief in the form of specific performance, temporary restra ining order, temporary or permanent injunction or any other equitable remedy which may then be available.