EMPLOYMENT AGREEMENT

Exhibit 10.31

EMPLOYMENT AGREEMENT

(As amended and restated effective as of May 1, 2009)

     This Amended and Restated Employment Agreement (“Agreement”) is effective as of May 1, 2009, by and between Odyssey Re Holdings Corp., a Delaware Corporation (“Employer”), and Andrew Barnard (“Executive”).

WITNESSETH

     WHEREAS, Executive is the Chief Executive Officer of the group of reinsurance and insurance companies constituted by Odyssey America Reinsurance Corporation and its subsidiaries; and

     WHEREAS, Executive entered into the Agreement effective as of June 30, 2005;

     WHEREAS, the parties desire to amend and restate the Agreement as of the date hereof so as to contain the terms and conditions set forth below and to govern the employment of Executive in the capacity described in the first recital above.

NOW THEREFORE, IT IS AGREED AS FOLLOWS:

ARTICLE I

EMPLOYMENT AND DUTIES; COMPENSATION

Section 1:     Duties

     During the term of this Agreement, Executive shall be employed by and shall serve Employer in the capacity of President and Chief Executive Officer and/or such other positions as may be mutually agreed upon between Executive and the Board of Directors of Employer during the term hereof, and shall be employed by and/or shall serve such subsidiaries of Employer in such capacities as Employer shall from time to time designate and as are consistent with Executive’s position as President and Chief Executive Officer of Employer. Executive shall devote substantially all of his business time to the business and affairs of Employer and shall use his best efforts, skills, and energy to promote Employer’s interests.

Section 2:     Term of Employment

      The term of employment of Executive by Employer under the Agreement commenced as of June 30, 2005 (the “Commencement Date”) and shall continue until May 1, 2016 (the “Term”). At any time prior to the expiration of the Term, Employer and Executive may, by mutual written agreement, extend Executive’s employment under the terms of this Agreement for such additional periods as they may agree.

Section 3:     Salary, Benefits and Additional Compensation

     As compensation and consideration for the performance by Executive of his duties and responsibilities pursuant to this Agreement, Employer agrees to pay, and/or to cause one or more of its subsidiaries to pay Executive, and Executive agrees to accept the following amounts and benefits (all Dollar amounts referred to herein are in United States Dollars):

(a)   Base Salary :  An Annual Base Salary of One Million Dollars ($1,000,000), pro rated for any calendar year within the Term for which employment does not extend for the entire calendar year. The Annual Base Salary shall be paid to Executive in equal bi-weekly installments.

(b)   Bonus Pool :  Executive shall participate to the extent of the percentage determined by the Board of Directors of Employer in the bonus pool (the “Bonus Pool”) created with respect to each accident underwriting year, consisting of that portion of the underwriting profit for such year designated by the Board of Directors of Employer.

(c)   Restricted Stock Grant :

     (i)  Executive shall receive as of the execution date hereof an award of that number of restricted shares (the “Restricted Shares”) of Employer, consisting of its Common Stock, par value $.01 per share, which when multiplied by the simple average of the closing prices of such common stock on the New York Stock Exchange on the twenty (20) business days next preceding May 1, 2009, yields the aggregate sum of Five Million Dollars ($5,000,000). Subject to subparagraphs (ii) and (iii) below, the foregoing grant shall be subject to the terms of Employer’s Restricted Share Plan. Executive shall become fully vested in the shares granted pursuant to the foregoing sentence, and all restrictions shall lapse, on May 1, 2016.

     (ii)  An award document evidencing the foregoing Restricted Share grant (the “Award Document”) shall be provided to Executive by Employer within 30 days of the date of execution hereof. The Award Document shall provide that (1) upon Employee’s Termination of Employment as a result of death, disability, reaching retirement age, Change in Control (as defined in Article II, Section 6 below) or termination by Employer for reasons other than For Cause (as defined in Article II, Section 3 below) the restricted period applicable to any Restricted Shares granted to Executive shall terminate and Executive shall become fully vested in the Award; and (2) if the stock of Employer at any time during the restricted period ceases to be publicly traded, then Employee shall have the option to receive a cash payment, payable by Employer within ten (10) days following written notice from Executive no later than thirty (30) days following the delisting of Employer stock from the exchange, equal to the number of shares of Restricted Stock of Employer held by Executive as of the delisting of the stock, times the greater of (a) the share price of Employer stock as of the close of business forty-five (45) trading days prior to its delisting and (b) the average share price of Employer stock (based on end of business day values) over the forty-five (45) trading day period prior to delisting. To the extent the cash payment exceeds the fair market value of the stock at the time of payment and Executive is a “specified employee” as defined in Section 409A of the Internal Revenue Code of 1986, as amended (the “Code”), the excess amount shall be paid the earlier of (A) six (6) months following termination of employment or (B) death. The foregoing subparagraph (2) shall not apply if the stock of Employer ceases to be publicly traded as a result of Employer having made a general assignment for the benefit of creditors, been adjudicated as bankrupt or insolvent, or having filed a voluntary petition in bankruptcy, a petition or answer seeking an arrangement with

creditors or to take advantage of any insolvency law or having filed an answer admitting the material allegations of a petition filed against Employer in bankruptcy.

     (iii)  Employer will take whatever action necessary, including, without limitation, amendment of the Odyssey Re Holdings Corp. Restricted Share Plan, to ensure that the issuance of Restricted Shares by Employer to Executive does not exceed the maximum number of shares available for such purpose.

(d)   Previously Awarded Restricted Stock :

     (i)  On June 14, 2001, Executive was granted 27,778 Restricted Shares (the “IPO Award”) of Employer’s common stock in connection with Employer’s initial public offering. Pursuant to the terms of the grant, the IPO Award was scheduled to become fully vested on June 14, 2011, at which time all restrictions would have lapsed on the 27,778 Employer Restricted Shares.

     (ii)  On August 11, 2001, Executive was granted 62,432 Restricted Shares (the “2001 Award”) of Employer’s common stock pursuant to Employer’s Restricted Share Plan in consideration for cancelling all rights to 6,500 Restricted Shares of the 13,000 Restricted Shares of Financial Holdings Limited (“Fairfax”) common stock that were originally granted to Executive on September 1, 1996 in connection with his employment by Fairfax (the “1996 Award”). Executive retained his rights to the remaining 6,500 Fairfax Restricted Shares granted under the 1996 Award. Executive was originally scheduled to become fully vested with respect to both the 1996 Award and the 2001 Award on September 1, 2006, at which time all restrictions would have lapsed on the remaining 6,500 Fairfax Restricted Shares and the 62,432 Employer Restricted Shares.

     Pursuant to the terms of Executive’s employment agreement with Employer, effective as of June 30, 2005 (the “2005 Employment Agreement”), (A) the vesting period applicable to the remaining 6,500 Fairfax Restricted Shares granted under the 1996 Award was extended from September 1, 2006 until June 30, 2010 and (B) the vesting period applicable to the 62,432 Employer Restricted Shares was extended from September 1, 2006 until June 30, 2010.

     (iii)  As consideration for entering into the 2005 Employment Agreement, Executive was granted 202,135 Restricted Shares (the “2005 Award”) of Employer’s common stock pursuant to Employer’s Restricted Share Plan. Pursuant to the terms of the grant, the 2005 Award was originally scheduled to vest with respect to twenty percent (20%) of the Restricted Shares on June 30, 2006, and on each anniversary thereafter with respect to an additional twenty percent (20%), such that on June 30, 2010 all restrictions would have lapsed on the 202,135 Employer Restricted Shares.

     (iv)  Upon the execution of this Agreement, each of the (A) 27,778 outstanding and unvested Employer Restricted Shares under the IPO Award, (B) remaining 6,500 outstanding and unvested Fairfax Restricted Shares under the 1996 Award, (C) 62,432 outstanding and unvested Employer Restricted Shares under the 2001 Award, and (D) remaining 80,854 outstanding and unvested Employer Restricted Shares under the 2005 Award shall fully vest and all restrictions shall lapse.

(e)   Additional Benefits :

     During the term of this Agreement, Executive shall be entitled to the following fringe benefits:

     (i)  Executive Benefits.  Executive shall be eligible to participate in such benefits and perquisites as are now generally available or later made generally available to executive officers of Employer or its subsidiaries.

     (ii)  Vacation.  Executive shall be entitled to vacation time consistent with his position as President and Chief Executive Officer of Employer.

     (iii)  Life Insurance.  Executive shall be eligible to participate in any life insurance program available to executive officers of Employer or its subsidiaries on terms at least as favorable as those generally made available to such executive officers.

     (iv)  Disability Insurance.  Executive shall be eligible to participate in any disability insurance program available to executive officers of Employer or its subsidiaries on terms at least as favorable as those generally made available to such executive officers.

     (v)  Automobile.  Executive shall be provided with the exclusive use of an automobile appropriate to his position as President and Chief Executive Officer of Employer (with all operating costs, such as insurance, maintenance and fuel, paid for by Employer).

     (vi)  Membership Fees.  Employer shall pay Executive’s membership and usage fees of the St. Andrews Golf Club (or of a comparable country club of Executive’s choosing).

     (vii)  Reimbursement for Expenses.  Employer shall reimburse Executive for reasonable and properly documented out-of-pocket business and/or entertainment expenses incurred by Executive in connection with his duties under this Agreement.

     (viii)  Reimbursement of Attorney’s Fees.  Employer shall pay all reasonable attorney’s fees and disbursements incurred by Executive in drafting and negotiating this Agreement;

payment shall be made either to Executive upon submission of paid invoices for such legal work or directly to the attorney chosen by Executive.

     (ix)  Tax Reimbursement.  Employer shall reimburse Executive for all federal, state and local income taxes incurred by Executive as a result of the inclusion in income of any of the benefits provided by Employer to Executive pursuant to this paragraph (e)(v) and (e)(vi). The determination of such taxes shall be based upon all applicable state, local and federal taxes (computed at the highest marginal income tax rate) including any taxes payable pursuant to Section 4999 of the Internal Revenue Code of 1986, as amended. Employer shall remit to Executive the amount of such taxes no later than April 15 ^th of the year following inclusion in income of any of the benefits for which tax reimbursement is provided herein.

ARTICLE II

TERMINATION OF EMPLOYMENT

Section 1:     Termination Due to Death

     The employment of Executive under this Agreement shall terminate upon Executive’s death. In the event of Executive’s death during Executive’s employment hereunder, the estate or other legal representative of Executive shall be entitled to receive the following:

(a)   Base Salary .  Employer shall pay to Executive’s estate or other legal representative of Executive, his Base Salary for the period ending three months following the month in which Executive dies. Such an amount and all other amounts payable under this Section 1 of Article II

shall be paid by Employer in a lump sum within thirty (30) days of the date of death, provided however, that the amounts due with respect to the Bonus Pool shall be paid when such amounts would ordinarily be paid.

(b)   Payment from Bonus Pool .  Employer shall pay to the estate or other legal representative of Executive, (i) all amounts accrued in the Bonus Pool by Executive with respect to years preceding the year in which the death of Executive occurs and (ii) the pro-rated bonus payable with respect to the year in which the death of Executive occurs.

(c)   Restricted Stock .  Upon the death of Executive, the restricted period with respect to all Restricted Stock previously awarded to Executive including, without limitation, Restricted Stock of Employer awarded pursuant to this Agreement, shall terminate and Executive’s estate or other legal representative shall become fully vested in all Restricted Stock previously awarded to Executive.

Section 2:     Termination by Reason of Disability

     If, during the term of this Agreement, Executive, in the judgment of the Board of Directors of Employer, has failed to perform his duties under this Agreement on account of illness or physical or mental incapacity, and such illness or incapacity continues for a period of more than (i) six (6) consecutive months or (ii) one hundred eighty three (183) days in any consecutive three hundred sixty-five (365) day period, Employer shall have the right to commence process to terminate Executive’s employment under this Agreement on account of

disability. Employer shall send written notice to Executive of (i) its intention to commence such process, (ii) a medical doctor chosen by Employer to make the determination referred to in the next sentence, and (iii) Executive’s right within ten (10) days of receipt of the notice to choose a second medical doctor to make such determination. The purpose of the process shall be to determine whether Executive is unable on account of illness or physical or mental incapacity to perform his duties under this Agreement. Executive shall fully cooperate in this process, including by making himself available for and consenting to all examinations and tests required by any doctor making the aforesaid determination. The aforesaid determination shall be made by the medical doctor chosen by Executive, if he exercises his foregoing right to choose a doctor, and the medical doctor chosen by Employer. If the determination is being made by two medical doctors and they cannot agree within fifteen (15) days of their both being chosen, they shall as soon as reasonably possible select a third medical doctor to make the determination, who shall make the determination within fifteen (15) days of being chosen. The determination made by the foregoing process shall be conclusive. In the event Executive’s employment is terminated on account of disability, Executive’s rights to compensation and benefits shall be as follows:

(a)   Base Salary .  Executive shall be paid his Base Salary, less any benefits paid to him under disability insurance policies maintained by Employer, until his termination on account of disability.

(b)   Payment from Bonus Pool .  Employer shall pay to Executive, when the same would ordinarily be paid, (i) all amounts accrued in the Bonus Pool by Executive with respect to years

preceding the year in which termination due to disability of Executive occurs and (ii) the pro-rated bonus payable with respect to the year in which termination due to the disability of Executive occurs.

(c)   Restricted Stock .  The restricted period with respect to all restricted stock previously awarded to Executive shall terminate and Executive shall become fully vested in all Restricted Stock previously awarded to Executive, including, without limitation, Restricted Stock awarded pursuant to this Agreement.

Section 3:     Termination for Cause

     “Termination for Cause” shall mean termination by Employer of Executive’s employment by Employer by reason of:

     (i)  a willful failure by Executive in bad faith to substantially perform his duties with Employer resulting in material harm to Employer; or

     (ii)  Executive’s conviction of a felony involving moral turpitude.

     Executive must be given written notice that Employer intends to terminate his employment for Cause. Such written notice shall specify the particular act