Document:

exv10w15

Exhibit 10.15

ODYSSEY RE HOLDINGS CORP.

(NON-QUALIFIED)

2010 EMPLOYEE SHARE PURCHASE PLAN

     1. Purpose. The purpose of the Odyssey Re Holdings Corp. (Non-Qualified) 2010
Employee Share Purchase Plan, as may be amended from time to time (the “Plan”), is to provide
eligible Employees with an opportunity to purchase Shares (as such terms are defined below) through
payroll deductions and employer contributions. Participation in the Plan shall provide eligible
Employees who wish to acquire an interest in the long-term performance and success of Fairfax
Financial Holdings Limited with a method of doing so that is both convenient and, by virtue of
employer contributions, favorable to the Employees. The Plan is not intended to qualify as an
“Employee Stock Purchase Plan” under Section 423 of the Code (as such term is defined below).

     2. Definitions and Rules of Construction.

          (a) Definitions. For purposes of the Plan, the following capitalized words shall have the
meanings set forth below:

          “Account” means a separate account that the Administrator maintains for each Participant
under the Plan.

          “Administrator” means the Board, or such other person(s), committee or entity as may be
designated from time to time by the Board to administer the Plan in accordance with the terms
herein.

          “Board” means the Board of Directors of the Company or any committee of the Board of
Directors as the Board of Directors may determine from time to time.

          “Code” means the U.S. Internal Revenue Code of 1986, as amended from time to time, and
the regulations promulgated thereunder.

          “Company” means Odyssey Re Holdings Corp., a Delaware corporation, and its successors
and assigns, and includes, except in these definitions, if and to the extent applicable, a
Participating Company.

          “Company Contributions” means the contributions of the Company to the Plan provided for
in Section 6.

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          “Custodian” means an independent custodian designated by the Administrator, in its sole
discretion.

          “Earnings” means a Participant’s base salary or wages for each payroll period before
giving effect to any salary reduction agreement pursuant to a qualified cash or deferred
arrangement within the meaning of Section 401(k) of the Code or to any similar reduction
agreement pursuant to any cafeteria plan (within the meaning of Section 125 of the Code).

          “Earnings Percentage” means the percentage (which may be any whole number from 1 to 10
inclusive) of a Participant’s Earnings that the Company will deduct as Participant
Contributions; provided, however, that the Administrator may determine and
specify, from time to time, in its sole discretion, (i) the range of permissible percentages
of a Participant’s Earnings that may be deducted as Participant Contributions and (ii) the
maximum amount, if any, of Earnings that may be deducted for a Participant in any Plan Year.

          “Effective Date” means January 1, 2010.

          “Employee” means any individual who is employed on a full-time basis by a Participating
Company, as determined by the Administrator, in its sole discretion, and any other individual
designated by the Administrator who is employed on a regular basis by a Participating
Company.

          “Participant” means an Employee who has (i) elected to participate in the Plan pursuant
to the provisions of Section 4, (ii) completed the Probationary Period and (iii) not
withdrawn from the Plan.

          “Participant Contributions” means the contributions of a Participant to the Plan
pursuant to the provisions of Section 5.

          “Participating Company” means and includes the Company and any Subsidiary, and any
affiliate of the Company and any Subsidiary that has elected to participate in the Plan with
the consent of the Company.

          “Probationary Period” means, with respect to an Employee, and unless determined
otherwise by the Administrator, in its sole discretion, the period commencing on such
Employee’s date of hire and ending on the six (6)-month anniversary of such Employee’s date
of hire.

          “Purchase Period” means, unless otherwise determined by the Administrator, in its sole
discretion, the period beginning on the first day of each payroll period applicable to a
Participant and continuing through the last day of the applicable payroll period.

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          “Restricted Period” means, with respect to any Shares, the period of time during which a
Share is subject to restrictions on transfer as set forth in Section 10.

          “Shares” means the Subordinate Voting Shares, no par value, of Fairfax Financial
Holdings Limited.

          “Subsidiary” means any (i) corporation if fifty percent (50%) or more of the total
combined voting power of all classes of stock is owned, either directly or indirectly, by the
Company or another Subsidiary or (ii) limited liability company if fifty percent (50%) or
more of the membership interests is owned, either directly or indirectly, by the Company or
another Subsidiary.

          “Transfer” means to sell, assign, transfer, pledge or otherwise dispose of, or encumber,
any Share.

          “Year” or “Plan Year” means the calendar year.

          (b) Rules of Construction. The masculine pronoun shall be deemed to include the feminine
pronoun and the singular form of a word shall be deemed to include the plural form, unless the
context requires otherwise. Unless the text indicates otherwise, references to “Sections” are to
sections of the Plan.

     3. Eligibility. Each Employee who remains an Employee following the expiration of the
Probationary Period shall be eligible to participate in the Plan. Subject to the satisfaction of
Section 4, an Employee shall be eligible to participate in the Plan commencing in the first payroll
period that falls entirely outside the Probationary Period. An Employee who has met the
requirements of this Section 3 and who subsequently ceases to be an Employee shall again be
eligible to participate in the Plan when he again becomes eligible under this Section 3.

     4. Participation.

          (a) An Employee may elect to participate in the Plan by satisfying all requirements of a
Company-specified enrollment procedure, which shall include indicating the Employee’s desired
Earnings Percentage. Such election shall not be effective with respect to any payroll period
unless the Administrator determines, in its sole discretion, that the Company-specified enrollment
procedure has been completed. Any such election shall remain in effect until it is changed or
revoked by the Participant, or the Participant ceases to be eligible to participate in the Plan in
accordance with the procedures as may be established from time to time by the Administrator, in its
sole discretion.

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          (b) Unless otherwise determined by the Administrator, in its sole discretion, upon a
Participant’s termination of employment with a Participating Company for any reason (the date of a
Participant’s termination of employment shall be determined by the Administrator, in its sole
discretion), such Participant shall be deemed to have withdrawn from the Plan.

     5. Contributions by Participants.

          (a) Participants shall make Participant Contributions by means of regular payroll deductions
in an amount, as regards each Participant, equal to that Participant’s then elected Earnings
Percentage. Such payroll deductions shall be made during each payroll period. No interest shall
accrue or be paid on Participant Contributions credited to a Participant’s Account.

          (b) A Participant may, at any time and for any reason, elect to adjust the Participant’s
Earnings Percentage, terminate the Participant’s Participant Contributions or withdraw from the
Plan by satisfying all requirements of a Company-specified enrollment procedure; provided, however,
that, unless otherwise determined by the Administrator, in its sole discretion, such Participant
may elect such procedure only once in any thirty (30)-day period. Such request shall be effective
as of the first day of the payroll period commencing after the date of providing such notice to
which it may be practically applied.

          (c) Unless otherwise determined by the Administrator, in its sole discretion, if a Participant
terminates Participant Contributions or withdraws from the Plan, such Participant shall not be
permitted to recommence Participant Contributions or re-enroll in the Plan for ninety (90) days
following such termination or withdrawal.

Contributions by the Company.

          (d) Unless otherwise determined by the Administrator, in its sole discretion, the Company
shall, as soon as practicable, following the completion of each Purchase Period, allocate a Company
Contribution to the Account of each Participant in an amount equal to thirty percent (30%) of the
aggregate amount of Participant Contributions made by the Participant during such Purchase Period.
No interest shall accrue or be paid on Company Contributions credited to a Participant’s Account.

          (e) The Company shall, within ninety (90) days after the end of each Plan Year in which the
total shareholders’ equity of the Company attributable to the common equity as adjusted for
dividends, capital contributions or other extraordinary events (the “Book Value”) (in each case, as
determined by the Administrator, in its sole discretion, in accordance with generally accepted
accounting principles) as of the last day of such Plan Year (the “Measurement Plan Year”) has
increased by at least fifteen percent (15%) over the Book Value as of the last day of the
immediately preceding Plan Year, allocate an additional Company Contribution to

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the Account of each Participant on the date of the allocation in an amount equal to twenty
percent (20%) of the aggregate amount of Participant Contributions made by the Participant during
the Measurement Plan Year.

     6. Accounts and Allocations to Participants.

          (a) The Administrator shall establish and maintain a separate Account in respect of each
Participant showing all Participant Contributions and Company Contributions, the total number of
whole Shares (and fractional Shares), and the amount of cash dividends, if any, allocated to a
Participant’s Account.

          (b) All Participant Contributions and Company Contributions shall be forwarded by the
Administrator to the Custodian in a timely manner, consistent with the terms herein.

     7. Vesting. All Participant Contributions and Company Contributions allocated to a
Participant’s Account shall be fully and immediately vested upon being allocated to the
Participant’s Account.

     8. Purchase of Shares.

          (a) The Administrator shall designate a Custodian that shall acquire Shares as the agent for
the Participants. The Custodian shall use the Participant Contributions and the Company
Contributions (and cash dividends, if any) forwarded to it to purchase on the open market in a
timely manner as many Shares as may be acquired with such contributions at the market price of a
Share at the time of such purchase. All cash dividends paid with respect to Shares held in a
Participant’s Account shall be invested automatically in Shares in a timely manner. No interest
shall accrue or be paid on dividends credited to a Participant’s Account.

          (b) Upon any such purchase of Shares, the Custodian shall allocate to each Participant’s
Account the number of whole or fractional Shares to which such Participant is entitled. All Shares
purchased pursuant to the provisions of this Section 9 shall be subject to a Restricted Period and
such Shares shall be held by the Custodian in escrow on behalf of the applicable Participant until
the expiration of the Restricted Period.

          (c) During the Restricted Period, all shareholder rights with respect to Shares allocated to a
Participant’s Account (including the right to vote) shall be exercisable by the Participant, except
as expressly provided otherwise herein.

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     9. Restricted Period.

          (a) A Participant may not Transfer any Share allocated to the Participant’s Account in any
Plan Year during the period commencing on the date such Share is so allocated and expiring on the
last day of February of the immediately following Plan Year (the “Restricted Period”).

          (b) Subject to the terms of this Plan, until the expiration of the Restricted Period, a
Participant shall not be entitled to delivery of any Share that is subject to the restrictions on
transferability set forth in Section 10(a).

          (c) Any cash dividends and stock dividends with respect to Shares subject to a Restricted
Period shall be subject to the same restrictions as the underlying Shares.

     10. Distributions from the Plan.

          (a) Upon the expiration of the Restricted Period with respect to any Share, the restrictions
set forth in Section 10 shall be of no further force or effect with respect to such Share. A
Participant may, at any time, elect to complete a Company-specified procedure notifying the Company
that the Participant wishes to withdraw some or all of the Shares allocated to the Participant’s
Account for which the applicable Restricted Period has expired, in which event the Custodian shall
promptly issue and deliver to the Participant, without charge, the number of whole Shares
requested, subject to the terms herein, together with a cash payment in lieu of fractional Shares,
if any. Any such distribution shall reduce accordingly the number of Shares allocated to such
Participant’s Account.

          (b) A Participant whose employment with a Participating Company has terminated for any reason
shall receive a refund of the uninvested balance of his Participant Contributions, Company
Contributions and cash dividends, if any, as soon as practicable following the date of such
termination of employment. Within a reasonable time after the termination of a Participant’s
employment with a Participating Company for any reason, the Custodian and/or the Administrator
shall issue and deliver to the Participant, without charge, the whole Shares credited to the
Participant’s Account, together with a cash payment in lieu of fractional Shares (if any) credited
to the Participant’s Account, in the amount determined by the Administrator, and with any other
assets then credited to the Participant’s Account.

          (c) Subject to the terms of the Plan, a Participant may, at any time and from time to
time, request receipt of an immediate distribution of part or all of the Shares or other assets
credited to the Participant’s Account, or to otherwise reduce any Restricted Period. The decision upon any such application
shall be at the sole discretion of the Administrator, and no such decision, or any other

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determination permitted on a discretionary basis hereunder to the Administrator or the
Company, shall have any precedent value. Any such distribution shall reduce accordingly the number
of Shares allocated to such Participant’s Account.

     11. Administration.

          (a) The Administrator may make, amend and repeal at any time and from time to time such
procedures not inconsistent herewith as it may deem necessary or advisable for the proper
administration and operation of the Plan. In connection herewith, the Board may delegate to any
committee, person(s), or entity, such administrative duties and powers as it may see fit. Any such
delegation shall be subject to the restrictions and limitations that the Board specifies at the
time of such delegation.

          (b) Notwithstanding the foregoing, the Administrator shall have full power and authority,
subject to the express provisions hereof, to (i) make any legal or factual determinations, (ii)
construe and interpret the provisions of the Plan, (iii) formulate administrative rules and
procedures, (iv) make such changes in the administration of the Plan and in the administrative
rules and procedures and (v) make all other determinations as the Administrator, from time to time,
deems necessary or appropriate. All decisions and interpretations of the Administrator respecting
the Plan and all rules and procedures made from time to time pursuant hereto shall be final,
binding and conclusive for all purposes and upon all persons interested.

     12. Participant’s Eligibility and Interests Not Transferable. Except as otherwise
provided herein, and except for transfers by will or under the laws of descent and distribution, no
Participant shall have the right to Transfer either the Participant’s eligibility to participate in
the Plan or the Participant’s interest in the Shares or other assets credited to the Participant’s
Account, and no such attempted Transfer shall be effective.

     13. Liability. No member of the Board or any of its committees or the Administrator
shall have any liability or responsibility to any Employee, Participant or otherwise with respect
to the Plan, and the Company or a Participating Company (if applicable) shall indemnify and hold
harmless each such person from any liability arising from or in connection with the Plan, except
with respect to fraud, bad faith or willful misconduct. In the performance of their functions with
respect to the Plan, the Board and the Administrator shall be entitled to rely upon information and
advice furnished by the Company’s officers, accountants, legal counsel and any other party that the
Board or the Administrator deems necessary or appropriate, and no member of the Board or the
Administrator shall be liable for any action taken or not taken in reliance upon any such advice.

     14. Amendment; Termination. Notwithstanding anything herein to the contrary, the
Board may, at any time, amend, modify, terminate or suspend the Plan; provided,
however, that no amendment or modification that otherwise must be approved by

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shareholders, pursuant to applicable rules of a stock exchange or any requirements under the
Code, shall be effective without shareholder approval; and, provided, further,
that, except as otherwise expressly provided herein, no such action shall, without the express
written consent of a Participant, impair or adversely affect a Participant’s rights existing at
such time with respect to any Shares or other assets credited to a Participant’s Account.

     15. Distribution upon Termination of Plan. Upon termination of the Plan, all assets
credited to all Accounts shall, within a reasonable time after such termination, be distributed to
the respective Participants in a manner similar to the distributions provided for in Section 11(b).

     16. Costs. The Company shall pay all costs of administering the Plan, including
brokerage fees with respect to the purchase of Shares pursuant to the Plan.

     17. No Right to Continued Employment. Participation in the Plan shall be entirely
voluntary and shall not be construed to give any Participant the right to be employed or to
continue to be employed by the Company or any Subsidiary.

     18. Issuance and Delivery of Shares. Shares shall not be issued to a Participant
unless the issuance and delivery of the Shares comply with all applicable provisions of law,
domestic or foreign, including, without limitation, applicable securities laws, and the rules of
any other stock exchange or market upon which the Shares are then listed or traded and any rules
and regulations promulgated under any of the foregoing, and shall be further subject to the
approval of counsel for the Company with respect to such compliance.

     19. Awards to Individuals Subject to Laws of a Jurisdiction Outside of the United
States. To the extent the Administrator, in its sole discretion, deems it necessary,
appropriate or desirable to comply with the laws of any relevant jurisdiction or practice and to
further the purposes of the Plan and the interests of the Company, the Administrator may, without
amending the Plan, adopt, on behalf of the Company or any Participating Company, one or more
sub-plans applicable to separate classes of Employees who are subject to laws of jurisdictions
outside of the United States, including, without limitation, establishing a trust in connection
with the Plan.

     20. Offsets. To the extent permitted by applicable law, the Company shall have the
absolute right to withhold any amounts payable to any Participant under the terms of the Plan to
the extent of any amount owed for any reason by such Participant to the Company or any Subsidiary
and to set off and apply the amounts so withheld to payment of any such amount owed to the Company
or any Subsidiary, whether or not such amount shall then be immediately due and payable and in such
order or priority as among such amounts owed as the Company, in its sole discretion, shall
determine.

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     21. Wage and Tax Withholding. A Participating Company is authorized to withhold from
any Shares or any compensation or other payment to a Participant amounts of income and employment
tax withholding and other tax withholdings due in connection with any Shares or with any Company
Contributions (or with dividends, if any), and to take such other action as the Administrator, in
its sole discretion, may deem necessary or advisable to enable the Company and the Participants to
satisfy obligations for the payment of withholding taxes and other tax obligations relating
thereto. This authority shall include authority for the Company to withhold or receive Shares or
other property and to make cash payments in respect thereof in satisfaction of a Participant’s tax
obligations, either on a mandatory or elective basis, in the sole discretion of the Company.

     22. Effective Date. The Plan shall become effective on the Effective Date, and shall
remain in effect until it has been terminated pursuant to Section 15.

     23. Applicable Law. The Plan shall be subject to and construed in accordance with the
laws of the State of Delaware (without giving effect to principles of conflicts of laws)

[THE BALANCE OF THIS PAGE IS INTENTIONALLY LEFT BLANK]

9exv10w23

Exhibit 10.23

SECOND AMENDMENT AGREEMENT

     THIS
SECOND AMENDMENT AGREEMENT, dated as of the
24th day of February, 2010 (this “Second
Amendment”), is entered into among ODYSSEY RE HOLDINGS CORP., a Delaware corporation (the
“Borrower”), various Subsidiary Credit Parties (as defined in the hereinafter defined
Credit Agreement) party hereto, the Lenders (as defined in the hereinafter defined Credit
Agreement) party hereto, and WACHOVIA BANK, NATIONAL ASSOCIATION, as administrative agent for the
Lenders (the “Administrative Agent”).

RECITALS

     A. The Borrower, the Subsidiary Credit Parties, the Lenders and the Administrative Agent are
parties to that certain Credit Agreement dated as of July 13, 2007, as amended by the First
Amendment Agreement, dated as of June 17, 2009 (as further amended, restated, supplemented or
otherwise modified from time to time, the “Credit Agreement”). Capitalized terms used
herein without definition shall have the meanings given to them in the Credit Agreement as they may
be amended pursuant to this Second Amendment.

     B. The Borrower, the Administrative Agent and the Required Lenders have agreed to make certain
amendments to the Credit Documents on the terms and conditions set forth herein.

STATEMENT OF AGREEMENT

     NOW, THEREFORE, in consideration of the foregoing and other good and valuable consideration,
the receipt and sufficiency of which are hereby acknowledged, the parties hereto agree as follows:

ARTICLE I

AMENDMENTS TO CREDIT AGREEMENT

     1.1 Amendments to Section 1.1 Consisting of New Definitions. The following
definitions are hereby added to Section 1.1 of the Credit Agreement in appropriate alphabetical
order:

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     “‘Second Amendment’ shall mean the Second Amendment Agreement, dated as
of February 24, 2010, among the Borrower, the Subsidiary Credit Parties party thereto,
the Lenders party thereto, and the Administrative Agent.”

     “‘Second Amendment Effective Date’ has the meaning given to such term in
Article III to the Second Amendment.”

     “‘Watsa Controlled Affiliates” means V. Prem Watsa, trusts established by
or for the benefit of V. Prem Watsa, and other Persons Controlled by V. Prem Watsa.”

     1.2 Amendments to Section 1.1 Consisting of Modifying Existing Definitions. The
following definition in Section 1.1 of the Credit Agreement is hereby amended and restated in its
entirety as follows:

               “Change of Control” means an event or series of events by which:

     (a) Watsa Controlled Affiliates shall collectively cease to be the “beneficial
owner” (as defined in Rules 13d-3 and 13d-5 under the Securities Exchange Act of 1934,
except that a person or group shall be deemed to have “beneficial ownership” of all
Equity Interests that such person or group has the right to acquire (such right, an
“option right”), whether such right is exercisable immediately or only after
the passage of time), directly or indirectly, of 35% or more of the Equity Interests
of Fairfax entitled to vote for members of the board of directors or equivalent
governing body of Fairfax on a fully-diluted basis (and taking into account all such
securities that such person or group has the right to acquire pursuant to any option
right); or

     (b) both (i) any “person” or “group” (as such terms are used in Sections 13(d)
and 14(d) of the Securities Exchange Act of 1934, but excluding any employee benefit
plan of such person or its subsidiaries, any person or entity acting in its capacity
as trustee, agent or other fiduciary or administrator of any such plan and any Watsa
Controlled Affiliate) becomes the beneficial owner (as defined in clause (a) above),
directly or indirectly, of 35% or more of the Equity Interests of Fairfax entitled to
vote for members of the board of directors or equivalent governing body of Fairfax on
a fully-diluted basis (and taking into account all such securities that such person or
group has the right to acquire pursuant to any option right) and (ii) Watsa Controlled
Affiliates shall collectively cease to be the “beneficial owner” (as defined in clause
(a) above), directly or indirectly, of Equity Interests of Fairfax entitled to vote
for members of the board of directors or equivalent governing body of Fairfax on a
fully-diluted basis (and

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taking into account all such securities that such person or group has the right
to acquire pursuant to any option right) in an amount greater than such person or
group described in clause (i) above; or

     (c) Fairfax shall fail to own 75% or more of the Equity Interests of the
Borrower; or

     (d) any Change of Control (as defined in any other Indebtedness of the Borrower
or any of its Subsidiaries) shall occur.

     1.3 Amendments to Section 2.9 (Fees). Sections 2.9(e) and (f) of the Credit Agreement
are hereby amended and restated in their entirety as follows:

     “(e) To the Administrative Agent, for the account of each Tranche 2 Lender, a
commitment fee (the “Tranche 2 Commitment Fee”) for each calendar quarter (or
portion thereof) at a per annum rate of 0.10% on such Lender’s Tranche 2 Ratable Share
of the average daily aggregate Unutilized Tranche 2 Commitments, payable in arrears
(i) on the last Business Day of each calendar quarter, beginning with the first such
day to occur after the Second Amendment Effective Date through the Tranche 2
Termination Date, and (ii) on the Tranche 2 Termination Date;

     (f) To the Administrative Agent, for the account of each Tranche 2 Lender, a
letter of credit fee (the “Tranche 2 Letter of Credit Fee”) for each calendar
quarter (or portion thereof) in respect of all Tranche 2 Letters of Credit outstanding
during such quarter, at a per annum rate equal to 0.55% on such Tranche 2 Lender’s
Tranche 2 Ratable Share of the average daily aggregate Stated Amount of such Tranche 2
Letters of Credit. The Tranche 2 Letter of Credit Fee shall be due and payable
quarterly in arrears (i) on the last Business Day of each calendar quarter, commencing
with the first such date to occur after the Second Amendment Effective Date through
the Final Maturity Date and (ii) on the Final Maturity Date; and”

     1.4 Amendments to Section 2.19 (Increase in Commitments). Section 2.19 of the Credit
Agreement is hereby amended and restated in its entirety as follows:

               “Section 2.19 Increase in Commitments.

     (a) The Borrower shall have the right, at any time prior to the date 6 months
prior to the Tranche 2 Termination Date by written notice to and in consultation with
the Administrative Agent, to request an increase in the Tranche 2 Commitments (each
such requested increase, a “Commitment Increase”), by having one or more

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existing Tranche 2 Lenders increase their respective Tranche 2 Commitments then
in effect (each, an “Increasing Lender”), by adding as a Tranche 2 Lender with
a new Tranche 2 Commitment hereunder one or more Persons that are not already Tranche
2 Lenders (each, an “Additional Lender”), or a combination thereof;
provided that (i) any such request for a Commitment Increase shall be in a
minimum amount of $10,000,000 or an integral multiple of $5,000,000 in excess thereof,
(ii) immediately after giving effect to any Commitment Increase, (y) the aggregate
Tranche 2 Commitments shall not exceed $150,000,000 and (z) the aggregate of all
Commitment Increases effected after the Effective Date shall not exceed $50,000,000,
and (iii) no existing Tranche 2 Lender shall be obligated to increase its Tranche 2
Commitment as a result of any request for a Commitment Increase by the Borrower unless
it agrees in its sole discretion to do so.

     (b) Each Additional Lender must qualify as an Eligible Assignee (the approval
of which by the Administrative Agent and the Fronting Bank shall not be unreasonably
withheld or delayed) and the Borrower and each Additional Lender shall execute a
joinder agreement together with all such other documentation as the Administrative
Agent and the Borrower may reasonably require, all in form and substance reasonably
satisfactory to the Administrative Agent and the Borrower, to evidence the Tranche 2
Commitment of such Additional Lender and its status as a Tranche 2 Lender hereunder.

     (c) If the aggregate Tranche 2 Commitments are increased in accordance with
this Section, the Administrative Agent and the Borrower shall determine the effective
date (the “Commitment Increase Date,” which shall be a Business Day not less
than thirty (30) days prior to the Commitment Termination Date) and the final
allocation of such increase. The Administrative Agent shall promptly notify the
Borrower and the Lenders of the final allocation of such increase and the Commitment
Increase Date. The Administrative Agent is hereby authorized, on behalf of the
Lenders, to enter into any amendments to this Agreement and the other Credit Documents
as the Administrative Agent shall reasonably deem appropriate to effect such
Commitment Increase.

     (d) Notwithstanding anything set forth in this Section 2.19 to the contrary, no
increase in the Tranche 2 Commitments pursuant to this Section 2.19 shall be effective
unless:

     (i) The Administrative Agent shall have received the following, each
dated the Commitment Increase Date and in form and substance reasonably
satisfactory to the Administrative Agent:

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     (A) as to each Increasing Lender, evidence of its agreement to
provide a portion of the Commitment Increase, and as to each Additional
Lender, a duly executed joinder agreement together with all other
documentation required by the Administrative Agent pursuant to Section
2.19(b);

     (B) an instrument, duly executed by each Credit Party,
acknowledging and reaffirming its obligations under this Agreement, the
Security Documents and the other Credit Documents to which it is a
party and the validity and continued effect of the Liens granted in
favor of the Administrative Agent thereunder;

     (C) a certificate of the secretary or an assistant secretary of
each Credit Party, certifying to and attaching the resolutions adopted
by the board of directors (or similar governing body) of such Credit
Party approving or consenting to such Commitment Increase;

     (D) a certificate of a Financial Officer of the Borrower,
certifying that (y) as of the Commitment Increase Date, all
representations and warranties of the Credit Parties contained in this
Agreement and the other Credit Documents qualified as to materiality
are true and correct and those not so qualified are true and correct in
all material respects, both immediately before and after giving effect
to the Commitment Increase and any Letters of Credit issued in
connection therewith (except to the extent any such representation or
warranty is expressly stated to have been made as of a specific date,
in which case such representation or warranty is true and correct (if
qualified as to materiality) or true and correct in all material
respects (if not so qualified), in each case as of such date), and (z)
no Default or Event of Default has occurred and is continuing, both
immediately before and after giving effect to such Commitment Increase
(including any Letters of Credit issued in connection therewith and the
application of the proceeds thereof); and

     (ii) Each outstanding Syndicated Letter of Credit shall have been amended
giving effect to the Commitment Increase or, if required, returned by each
respective beneficiary to the Administrative Agent and cancelled and/or
exchanged for a new or amended Syndicated Letter of Credit giving effect to
the Commitment Increase; and

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(iii) In the case of any Credit Extension in connection with such
Commitment Increase, the conditions precedent set forth in Section 4.2 shall
have been satisfied.”

     1.5 Amendments to Section 7.2 (Investments). Section 7.2 of the Credit Agreement is
hereby amended and restated in its entirety as follows:

     Section 7.2 Investments. Make any Investments in (a) Fairfax, Crum &
Forster, Northbridge Financial, TIG Insurance Group, TIG Insurance Company, ORH
Holdings, Inc., Fairfax Financial (US) LLC, United States Fire Insurance Company or
Fairfax Inc. or their respective Affiliates and Subsidiaries (other than the Borrower
and its Subsidiaries) or (b) debt and equity securities of Fairfax, Crum & Forster,
Northbridge Financial, TIG Insurance Group, TIG Insurance Company, ORH Holdings, Inc.,
Fairfax Financial (US) LLC, United States Fire Insurance Company or Fairfax Inc. or
their respective Affiliates and Subsidiaries (other than the Borrower and its
Subsidiaries), other than in each case Investments made from Cash on Hand (as defined
in Section 7.6(b)) and the proceeds of Restricted Payments received by the Borrower
pursuant to Restricted Payments permitted to be made (and made) to the Borrower after
the Second Amendment Effective Date in accordance with Section 7.6(a);
provided, however, (A) each such Investment shall be permitted by the
applicable Investment Guidelines, (B) each such Investment shall not violate any
Requirement of Law and (C) no Default or Event of Default shall have occurred and be
continuing (or result therefrom).”

     1.6 Amendments to Section 7.6 (Restricted Payments). Sections 7.6(b) and (c) of the
Credit Agreement are hereby amended and restated in their entirety as follows:

     “(b) the Borrower may make Restricted Payments (i) in an aggregate amount
equal to the amount of cash, cash equivalents and marketable securities on hand
(“Cash on Hand”) as of the Second Amendment Effective Date, such amount not to
exceed $100,000,000, and (ii) in an aggregate amount (excluding any Restricted
Payments permitted under clause (i) hereof) equal to 100% of the Restricted Payments
received by the Borrower pursuant to Restricted Payments permitted to be made (and
made) to the Borrower after the Second Amendment Effective Date in accordance with
Section 7.6(a); provided, however, that, in the case of any Restricted
Payment to be made pursuant to clause (i) or (ii) above, both at the time of
declaration and of payment of each such Restricted Payment, no Default or Event of
Default shall have occurred and be continuing (or result therefrom);”

6

 

“(c) the Borrower may purchase, redeem, retire or otherwise acquire shares of
its common stock from the proceeds of Restricted Payments received by the Borrower
pursuant to Restricted Payments permitted to be made (and made) to the Borrower after
the Second Amendment Effective Date in accordance with Section 7.6(a);
provided, however, (A) each such Restricted Payment shall be permitted
by the applicable Investment Guidelines, (B) each such Restricted Payment shall not
violate any Requirement of Law and (C) no Default or Event of Default shall have
occurred and be continuing (or result therefrom);”

     1.7 Amendments to Section 7.13(b)(Minimum Statutory Surplus). Section 7.13(b) of the
Credit Agreement is hereby amended and restated in its entirety as follows:

               (b) “Minimum Statutory Surplus. Permit the Statutory Surplus of OARC
to be less than $2,000,000,000.”

     1.8 Amendments to Section 7.13(c)(Minimum Risk-Based Capital). Section 7.13(c) of the
Credit Agreement is hereby amended and restated in its entirety as follows:

     “(c) Minimum Risk-Based Capital. Permit the ratio of (i) “total
adjusted capital” (within the meaning of the Risk-Based Capital for Insurers Model Act
as promulgated by the NAIC as of the date hereof (the “Model Act”)) of OARC to
(ii) 2 times the “Authorized Control Level Risk-Based Capital” (within the meaning of
the Model Act) of OARC to be less than one hundred seventy five percent (175%), as of
the last day of any fiscal quarter, beginning with the fiscal quarter ending December
31, 2009.”

     1.9 Amendments to Section 8.1(m)(Events of Default-Ratings Downgrade). Section 8.1(m)
of the Credit Agreement is hereby amended and restated in its entirety as follows:

               “(m) Ratings Downgrade. The Financial Strength Rating for OARC falls below
A-; or”

ARTICLE II

TERMINATION OF TRANCHE 1 COMMITMENTS

     Effective as of the Second Amendment Effective Date, the aggregate Tranche 1 Commitments shall
be permanently terminated in whole, and by the execution hereof by the Required Lenders, the
requirement in Section 2.5(b) of the Credit Agreement to provide 3 Business Days prior written
notice to the Administrative Agent is hereby waived.

7

 

ARTICLE III

CONDITIONS OF EFFECTIVENESS

     This Second Amendment shall become effective as of the first date (such date being referred to
as the “Second Amendment Effective Date”) on which each of the following conditions shall have been
satisfied:

     (a) The Administrative Agent shall have received, dated as of the Second Amendment Effective
Date, an executed counterpart hereof from each of the Credit Parties and the Required Lenders;

     (b) On the Second Amendment Effective Date, the representations and warranties set forth in
Article IV hereof shall be true and correct in all material respects;

     (c) Since December 31, 2008, there has been no event or circumstance, either individually or
in the aggregate, that has had or could reasonably be expected to have a Material Adverse Effect;

     (d) The Borrower shall have paid to the Administrative Agent, for the benefit of each Lender
who approves this Second Amendment a nonrefundable amendment fee in the amount of 0.10% of such
approving Lender’s Tranche 2 Commitment, which fee shall be deemed fully earned as of the Second
Amendment Effective Date;

     (e) The Borrower shall have paid all principal, interest and other amounts outstanding under
the Credit Agreement with respect to the Tranche 1 Commitments and there shall be no Tranche 1
Credit Extensions outstanding;

     (f) The Borrower shall have paid to Wells Fargo Securities, LLC (“Wells Fargo Securities”) the
other fees required under the engagement letter from Wells Fargo Securities to the Borrower, dated
as of February 17, 2010; and

     (g) The Borrower shall have paid all reasonable out-of-pocket costs and expenses of the
Administrative Agent in connection with the preparation, negotiation, execution and delivery of
this Second Amendment (including, without limitation, the reasonable and documented fees and
out-of-pocket expenses of counsel for the Administrative Agent with respect thereto).

8

 

ARTICLE IV

REPRESENTATIONS AND WARRANTIES

     Each of the Credit Parties (solely as to itself and its Subsidiaries) represents and warrants
to the Administrative Agent, the Issuing Banks and the Lenders that (i) the representations and
warranties contained in the Credit Agreement and the other Credit Documents are true and correct in
all material respects on and as of the Second Amendment Effective Date, both immediately before and
after giving effect to this Second Amendment (except to the extent any such representation or
warranty is expressly stated to have been made as of a specific date, in which case such
representation or warranty shall be true and correct in all material respects as of such date),
(ii) this Second Amendment has been duly authorized, executed and delivered by such Credit Party
and constitutes the legal, valid and binding obligation of such Credit Party enforceable against it
in accordance with its terms, and (iii) no Default or Event of Default shall have occurred and be
continuing on the Second Amendment Effective Date, both immediately before and after giving effect
to this Second Amendment.

ARTICLE V

ACKNOWLEDGEMENT AND CONFIRMATION OF THE CREDIT PARTIES

     Each Credit Party hereby confirms and agrees that, after giving effect to this Second
Amendment, the Credit Agreement and the other Credit Documents to which it is a party remain in
full force and effect and enforceable against such Credit Party in accordance with their respective
terms and shall not be discharged, diminished, limited or otherwise affected in any respect, and
the amendments contained herein shall not, in any manner, be construed to constitute payment of, or
impair, limit, cancel or extinguish, or constitute a novation in respect of, the Obligations of the
Credit Parties evidenced by or arising under the Credit Agreement, the other Credit Documents, and
the liens and security interests in the Collateral, which shall not in any manner be impaired,
limited, terminated, waived or released, but shall continue in full force and effect. Each Credit
Party represents and warrants to the Lenders that it has no knowledge of any claims, counterclaims,
offsets, or defenses to or with respect to its obligations under the Credit Documents, or if such
Credit Party has any such claims, counterclaims, offsets, or defenses to the Credit Documents or
any transaction related to the Credit Documents, the same are hereby waived, relinquished, and
released in consideration of the execution of this Second Amendment. This acknowledgement and
confirmation by the Credit Parties is made and delivered to induce the Administrative Agent and the
Lenders to enter into this Second Amendment, and the Credit Parties acknowledge that the
Administrative Agent and the Lenders would not enter into this Second Amendment in the absence of
the acknowledgement and confirmation contained herein.

9

 

ARTICLE VI

MISCELLANEOUS

     6.1 Governing Law. This Second Amendment shall be governed by and construed and
enforced in accordance with the laws of the State of New York.

     6.2 Full Force and Effect. Except as expressly amended hereby, the Credit Agreement
shall continue in full force and effect in accordance with the provisions thereof on the date
hereof. As used in the Credit Agreement, “hereinafter,” “hereto,” “hereof,” and words of similar
import shall, unless the context otherwise requires, mean the Credit Agreement after amendment by
this Second Amendment. Any reference to the Credit Agreement or any of the other Credit Documents
herein or in any such documents shall refer to the Credit Agreement and Credit Documents as amended
hereby. This Second Amendment is limited as specified and shall not constitute or be deemed to
constitute an amendment, modification or waiver of any provision of the Credit Agreement except as
expressly set forth herein. This Second Amendment shall constitute a Credit Document under the
terms of the Credit Agreement.

     6.3 Expenses. The Borrower agrees on demand (i) to pay all reasonable fees and
expenses of counsel to the Administrative Agent, and (ii) to reimburse the Administrative Agent for
all reasonable out-of-pocket costs and expenses, in each case, in connection with the preparation,
negotiation, execution and delivery of this Second Amendment and the other Credit Documents
delivered in connection herewith.

     6.4 Severability. To the extent any provision of this Second Amendment is prohibited
by or invalid under the applicable law of any jurisdiction, such provision shall be ineffective
only to the extent of such prohibition or invalidity and only in any such jurisdiction, without
prohibiting or invalidating such provision in any other jurisdiction
or the remaining
provisions of this Second Amendment in any jurisdiction.

     6.5 Successors and Assigns. This Second Amendment shall be binding upon, inure to the
benefit of and be enforceable by the respective successors and permitted assigns of the parties
hereto.

     6.6 Construction. The headings of the various sections and subsections of this Second
Amendment have been inserted for convenience only and shall not in any way affect the meaning or
construction of any of the provisions hereof.

10

 

     6.7 Counterparts. This Second Amendment may be executed in any number of counterparts
and by different parties hereto on separate counterparts, each of which when so executed and
delivered shall be an original, but all of which shall together constitute one and the same
instrument. Delivery of an executed counterpart of a signature page of this Second Amendment by
telecopy or by electronic mail in a .pdf or similar file shall be effective as delivery of a
manually executed counterpart of this Second Amendment. A complete set of counterparts shall be
lodged with the Borrower and the Administrative Agent.

[THE BALANCE OF THIS PAGE IS INTENTIONALLY LEFT BLANK]

11

 

IN WITNESS WHEREOF, the parties hereto have caused this Second Amendment to be executed by
their duly authorized officers as of the date first above written.

	 	 	 	 	 
	 	ODYSSEY RE HOLDINGS CORP.

 	 
	 	By:  	
/s/ R. Scott Donovan 	 
	 	 	Name:  	R. Scott Donovan	 
	 	 	Title:  	Executive
Vice
President & Chief Financial Officer	 
	 
	 	ODYSSEY AMERICA REINSURANCE CORPORATION

 	 
	 	By:  	/s/ R. Scott Donovan 	 
	 	 	Name:  	R. Scott Donovan 	 
	 	 	Title:  	Executive
Vice
President 	 
	 
	 	CLEARWATER INSURANCE COMPANY

 	 
	 	By:  	/s/ R. Scott Donovan 	 
	 	 	Name:  	R. Scott Donovan 	 
	 	 	Title:  	President 	 
	 
	 	CLEARWATER SELECT INSURANCE COMPANY

 	 
	 	By:  	/s/ R. Scott Donovan 	 
	 	 	Name:  	R. Scott Donovan 	 
	 	 	Title:  	President 	 
	 
	 	HUDSON INSURANCE COMPANY

 	 
	 	By:  	/s/
Peter H. Lovell 	 
	 	 	Name:  	Peter H. Lovell 	 
	 	 	Title:  	SVP 	 
	 

 

 

	 	 	 	 	 
	 	HUDSON SPECIALTY INSURANCE COMPANY

 	 
	 	By:  	/s/
Peter H. Lovell 	 
	 	 	Name:  	Peter H. Lovell 	 
	 	 	Title:  	SVP 	 

 

 

	 	 	 	 	 

	 	 	 	 	 
	 	WACHOVIA BANK, NATIONAL

ASSOCIATION, as Administrative Agent, Fronting Bank and as a Lender

 	 
	 	By:  	/s/ Mark B.
Felker 	 
	 	 	Name:  	Mark B.
Felker 	 
	 	 	Title:  	Managing
Director
 Wachovia Bank, National Association
 	 

 

 

	 	 	 	 	 

	 	 	 	 	 
	 	KeyBank National Association

 	 
	 	By:  	/s/
Mary K. Young 	 
	 	 	Name:  	Mary K. Young 	 
	 	 	Title:  	Senior
Vice President 	 

 

 

	 	 	 	 	 

	 	 	 	 	 
	 	CITIBANK, N.A.

 	 
	 	By:  	/s/
Cynthia W. Priest	 
	 	 	Name:  	Cynthia W. Priest 	 
	 	 	Title:  	Vice
President 	 

 

 

	 	 	 	 	 
	 	The Bank of New York Mellon

 	 
	 	By:  	/s/
Paulette Truman 	 
	 	 	Name:  	Paulette Truman 	 
	 	 	Title:  	Vice
President 	 
	 

 

 

	 	 	 	 	 

	 	 	 	 	 
	 	 PNC BANK, NATIONAL
ASSOCIATION,
as a Lender

 	 
	 	By:  	/s/
Daniel R. Raynor 	 
	 	 	Name:  	Daniel R. Raynor 	 
	 	 	Title:  	Senior
Vice President 	 
	 

 

 

	 	 	 	 	 

	 	 	 	 	 
	 	 Webster Bank, National
Association
          

 	 
	 	By:  	/s/
Lawrence Davis 	 
	 	 	Name:  	Lawrence
Davis 	 
	 	 	Title:  	
Vice President

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