EX-4.19






Exhibit 4.19




FORM OF GUARANTEE AGREEMENT




     This GUARANTEE AGREEMENT, dated as of [       ], is executed and delivered by Odyssey Re
Holdings Corp., a Delaware corporation (the “Guarantor”), and The Bank of New York Mellon, as the
Guarantee Trustee (as defined herein) for the benefit of the Holders (as defined herein) from time
to time of the Preferred Securities (as defined herein) of OdysseyRe Capital Trust I, a Delaware
statutory business trust (the “Issuer”).



     WHEREAS, pursuant to an Amended and Restated Declaration of Trust (the “Declaration”), dated
as of [     ], among the trustees of the Issuer named therein, the Guarantor, as Sponsor, and the
Holders from time to time of undivided beneficial interests in the assets of the Issuer, the Issuer
is issuing as of the date hereof up to $[     ] aggregate liquidation amount of its preferred
securities designated the [     ]% Preferred Securities (the “Preferred Securities”) representing
undivided beneficial interests in the assets of the Issuer and having the terms set forth in
Exhibit B to the Declaration;



     WHEREAS, the Preferred Securities will be issued by the Issuer upon deposit of the Guarantor’s
Notes (as defined herein) with the Issuer as trust assets; and



     WHEREAS, as incentive for the Holders to purchase the Preferred Securities, the Guarantor
desires to irrevocably and unconditionally agree, to the extent set forth herein, to pay to the
Holders of the Preferred Securities the Guarantee Payments (as defined herein) and to make certain
other payments on the terms and conditions set forth herein.



     NOW, THEREFORE, in consideration of the purchase by each Holder of Preferred Securities, which
purchase the Guarantor hereby agrees shall benefit the Guarantor, the Guarantor executes and
delivers this Guarantee Agreement for the benefit of the Holders from time to time of the Preferred
Securities.



ARTICLE I




SECTION 1.1 Definitions.




     In this Guarantee Agreement, unless the context otherwise requires:



     (a) capitalized terms used in this Guarantee Agreement but not defined in the preamble above
have the respective meanings assigned to them in this Section 1.1 or as otherwise defined herein;



     (b) a term defined anywhere in this Guarantee Agreement has the same meaning throughout;



     (c) all references to “the Guarantee Agreement” or “this Guarantee Agreement” are to this
Guarantee Agreement as modified, supplemented or amended from time to time;



     (d) all references in this Guarantee Agreement to Articles and Sections are to Articles and
Sections of this Guarantee Agreement unless otherwise specified;



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     (e) a term defined in the Trust Indenture Act has the same meaning when used in this Guarantee
Agreement unless otherwise defined in this Guarantee Agreement or unless the context otherwise
requires; and



     (f) a reference to the singular includes the plural and vice versa.



     “Affiliate” has the same meaning as given to that term in Rule 405 of the Securities
Act of 1933, as amended, or any successor rule thereunder.



     “Commission” means the United States Securities and Exchange Commission.



     “Common Securities” means the securities representing undivided beneficial interests
in the assets of the Issuer, having the terms set forth in Exhibit A to the Declaration.



     “Corporation” means corporations, associations, companies (including limited liability
companies) and business trusts or any similar entity.



     “Covered Person” means any Holder or beneficial owner of Preferred Securities.



     “Distributions” means the periodic distributions and other payments payable to Holders
of Preferred Securities in accordance with the terms of the Preferred Securities set forth in
Exhibit B to the Declaration.



     “Event of Default” means a default by the Guarantor on any of its payment or other
obligations under this Guarantee Agreement.



     “Guarantee Payments” shall mean the following payments or distributions, without
duplication, with respect to the Preferred Securities, to the extent not paid or made by the
Issuer: (i) any accrued and unpaid Distributions and the redemption price, including all accrued
and unpaid Distributions to the date of redemption (the “Redemption Price”), with respect to the
Preferred Securities called for redemption by the Issuer but if and only to the extent that in each
case the Guarantor has made a payment to the Trust of interest or principal on the Notes and (ii)
upon a voluntary or involuntary dissolution, winding-up or liquidation of the Issuer (other than in
connection with the distribution of Notes to Holders or the redemption of all the Preferred
Securities upon the maturity or redemption of the Notes as provided in the Declaration), the lesser
of (a) the aggregate of the liquidation amount and all accrued and unpaid Distributions on the
Preferred Securities to the date of payment, to the extent the Issuer has funds available therefor,
and (b) the amount of assets of the Issuer remaining available for distribution to Holders in
liquidation of the Issuer (in either case, the “Liquidation Distribution”).



     “Guarantee Trustee” means The Bank of New York Mellon until a Successor Guarantee
Trustee has been appointed and accepted such appointment pursuant to the terms of this Guarantee
Agreement, and thereafter means each such Successor Guarantee Trustee.



     “Holder” shall mean any holder, as registered on the books and records of the Issuer,
of any Preferred Securities; provided, however, that in determining whether the
holders of the requisite percentage of Preferred Securities have given any request, notice, consent
or waiver hereunder, “Holder” shall not include the Guarantor or any entity directly or indirectly



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controlling or controlled by or under direct or indirect common control with the Guarantor;
provided further, that in determining whether the Holders of the requisite
liquidation amount of Preferred Securities have voted on any matter provided for in this Guarantee
Agreement, then for purposes of such determination only (and not for any other purposes hereunder),
if the Preferred Securities remain in the form of one or more Global Certificates (as defined in
the Declaration), the term “Holders” shall mean the holder of the Global Certificates acting at the
direction of the Preferred Security Beneficial Owners (as defined in the Declaration).



     “Indemnified Person” means the Guarantee Trustee, any Affiliate of the Guarantee
Trustee, and any officers, directors, shareholders, members, partners, employees, representatives
or agents of the Guarantee Trustee.



     “Indenture” means the Indenture dated as of [     ] between the Guarantor and The Bank
of New York Mellon, as trustee, and any supplemental indenture thereto, pursuant to which the Notes
are to be issued.



     “Majority in liquidation amount of the Preferred Securities” means, except as
otherwise required by the Trust Indenture Act, Holder(s) of outstanding Preferred Securities voting
together as a single class, who are the record owners of Preferred Securities whose liquidation
amount (including the stated amount that would be paid on redemption, liquidation or otherwise,
plus accrued and unpaid Distributions to the date upon which the voting percentages are determined)
represents more than 50% of the liquidation amount of all outstanding Preferred Securities. In
determining whether the Holders of the requisite amount of Preferred Securities have voted,
Preferred Securities which are owned by the Guarantor or any entity directly or indirectly
controlling or controlled by or under direct or indirect common control with the Guarantor or any
other obligor on the Preferred Securities shall be disregarded (to the extent known to be so owned
by the Guarantee Trustee) for the purpose of such determination.



     “Notes” means the series of subordinated notes issued by the Guarantor designated the
“[     ]% Subordinated Notes due [     ]”.



     “Offer” means the offer by the Issuer to sell Preferred Securities in consideration
for the deposit by the Guarantor of Notes as trust assets of the Issuer, all as described in a
Prospectus dated [     ], and a Prospectus Supplement dated [     ].



     “Person” means a legal person, including any individual, corporation, estate,
partnership, joint venture, association, joint stock company, limited liability company, trust,
unincorporated association, or government or any agency or political subdivision thereof, or any
other entity of whatever nature.



     “Preferred Securities” has the meaning set forth in the first WHEREAS clause above.



     “Redemption Price” means the amount payable on redemption of the Preferred Securities
in accordance with the terms of the Preferred Securities.



     “Responsible Officer” means, with respect to the Guarantee Trustee, the chairman of
the board of directors, the president, any vice-president, any assistant vice-president, the
secretary, any assistant secretary, the treasurer, any assistant treasurer, any trust officer or
assistant trust



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officer or any other officer of the Guarantee Trustee customarily performing
functions similar to those performed by any of the above designated officers and also means, with
respect to a particular corporate trust matter, any other officer to whom such matter is referred
because of that officer’s knowledge of and familiarity with the particular subject.



     “Successor Guarantee Trustee” means a successor Guarantee Trustee possessing the
qualifications to act as a Guarantee Trustee under Section 4.1.



     “Trust Indenture Act” means the Trust Indenture Act of 1939, as amended.



ARTICLE II




TRUST INDENTURE ACT




SECTION 2.1 Trust Indenture Act; Application.




     (a) This Guarantee Agreement is subject to the provisions of the Trust Indenture Act that are
required to be part of this Guarantee Agreement and shall, to the extent applicable, be governed by
such provisions.



     (b) If and to the extent that any provision of this Guarantee Agreement limits, qualifies or
conflicts with the duties imposed by Sec. 310 to 317, inclusive, of the Trust Indenture Act, such
imposed duties shall control.



     (c) The application of the Trust Indenture Act to this Guarantee Agreement shall not affect
the nature of the Preferred Securities as equity securities representing undivided beneficial
interests in the assets of the Issuer.



SECTION 2.2 Lists of Holders of Preferred Securities.




     (a) The Guarantor shall provide the Guarantee Trustee with such information as is required
under Sec. 312(a) of the Trust Indenture Act at the times and in the manner provided in Sec.
312(a).



     (b) the Guarantee Trustee shall comply with its obligations under Sec. 310(b), 311 and 312(b)
of the Trust Indenture Act.



SECTION 2.3 Reports by the Guarantee Trustee.




     Within 60 days after [       ] of each year (commencing with the year of the first anniversary
of the issuance of the Preferred Securities), the Guarantee Trustee shall provide to the Holders of
the Preferred Securities such reports as are required by Sec. 313 of the Trust Indenture Act, if
any, in the form, in the manner and at the times provided by Sec. 313 of the Trust Indenture Act.
The Guarantee Trustee shall also comply with the requirements of Sec. 313(d) of the Trust Indenture
Act.



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SECTION 2.4 Periodic Reports to Guarantee Trustee.




     The Guarantor shall provide to the Guarantee Trustee, the Commission and the Holders of the
Preferred Securities, as applicable, such documents, reports and information as required by Sec.
314(a)(l)-(3) (if any) of the Trust Indenture Act and the compliance certificates required by Sec.
314(a)(4) and (c) of the Trust Indenture Act, any such certificates to be provided in the form, in
the manner and at the times required by Sec. 314(a)(4) and (c) of the Trust Indenture Act (provided
that any certificate to be provided pursuant to Sec. 314(a)(4) of the Trust Indenture Act shall be
provided within 120 days of the end of each fiscal year of the Issuer).



SECTION 2.5 Evidence of Compliance with Conditions Precedent.




     The Guarantor shall provide to the Guarantee Trustee such evidence of compliance with any
conditions precedent, if any, provided for in this Guarantee Agreement which relate to any of the
matters set forth in Sec. 314(c) of the Trust Indenture Act. Any certificate or opinion required
to be given pursuant to Sec. 314(c) shall comply with Sec. 314(e) of the Trust Indenture Act.



SECTION 2.6 Events of Default; Waiver.




     (a) Subject to Section 2.6(b), Holders of Preferred Securities may by vote of at least a
Majority in liquidation amount of the Preferred Securities, (A) direct the time, method and place
of conducting any proceeding for any remedy available to the Guarantee Trustee, or exercising any
trust or power conferred upon by the Guarantee Trustee or (B) on behalf of the Holders of all
Preferred Securities waive any past Event of Default and its consequences. Upon such waiver, any
such default shall cease to exist, and any Event of Default arising therefrom shall be deemed to
have been cured, for every purpose of this Guarantee Agreement, but no such waiver shall extend to
any subsequent or other default or Event of Default or impair any right consequent thereon.



     (b) The right of any Holder of Preferred Securities to receive payment of the Guarantee
Payments in accordance with this Guarantee Agreement, or to institute suit for the enforcement of
any such payment, shall not be impaired without the consent of each such Holder.



SECTION 2.7 Disclosure of Information.




     The disclosure of information as to the names and addresses of the Holders of the Preferred
Securities in accordance with Sec. 312 of the Trust Indenture Act, regardless of the source from
which such information was derived, shall not be deemed to be a violation of any existing law, or
any law hereafter enacted which does not specifically refer to Sec. 312 of the Trust Indenture Act,
nor shall the Guarantee Trustee be held accountable by reason of mailing any material pursuant to a
request made under Sec. 312(b) of the Trust Indenture Act.



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SECTION 2.8 Conflicting Interest.




     The Declaration shall be deemed to be specifically described in this Guarantee Agreement for
the purposes of clause (i) of the first provision contained in Section 310(b) of the Trust
Indenture Act.



ARTICLE III




POWERS, DUTIES AND RIGHTS OF GUARANTEE TRUSTEE




SECTION 3.1 Powers and Duties of the Guarantee Trustee.




     (a) This Guarantee Agreement shall be held by the Guarantee Trustee on behalf of the Issuer
for the benefit of the Holders of the Preferred Securities. The Guarantee Trustee shall not
transfer its right, title and interest in the Guarantee Agreement to any Person except a Successor
Guarantee Trustee on acceptance by such Successor Guarantee Trustee of its appointment to act as
Guarantee Trustee or to a Holder of Preferred Securities exercising his or her rights pursuant to
Section 5.4. The right, title and interest of the Guarantee Trustee to the Guarantee Agreement
shall vest automatically in each Person who may hereafter be appointed as Guarantee Trustee in
accordance with Article IV. Such vesting and cessation of title shall be effective whether or not
conveyancing documents have been executed and delivered.



     (b) If an Event of Default occurs and is continuing, the Guarantee Trustee shall enforce this
Guarantee Agreement for the benefit of the Holders of the Preferred Securities.



     (c) This Guarantee Agreement and all moneys received by the Trust hereunder in respect of the
Guarantee Payments will not be subject to any right, charge, security interest, lien or claim of
any kind in favor of, or for the benefit of that Guarantee Trustee or its agents or their
creditors.



     (d) The Guarantee Trustee shall after the occurrence of an Event of Default, transmit by mail,
first class postage prepaid, to the holders of the Preferred Securities, as their names and
addresses appear upon the register, notice of all Events of Default known to the Guarantee
Trustee, unless such defaults shall have been cured before the giving of such notice; provided
that the Guarantee Trustee shall be protected in withholding such notice if and so long as the
board of directors, the executive committee, or a trust committee of directors and/or Responsible
Officers, of the Guarantee Trustee in good faith determine that the withholding of such notice is
in the interests of the Holders of the Preferred Securities. The Guarantee Trustee shall not be
deemed to have knowledge of any default except any default as to which the Guarantee Trustee shall
have received written notice or a Responsible Officer charged with the administration of this
Guarantee Agreement shall have obtained written notice.



     (e) The Guarantee Trustee shall not resign as a Trustee unless a Successor Guarantee Trustee
has been appointed and accepted that appointment in accordance with Article IV.



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SECTION 3.2 Certain Rights and Duties of the Guarantee Trustee.




     (a) The Guarantee Trustee, before the occurrence of an Event of Default and after the curing
of all Events of Default that may have occurred, shall undertake to perform only such duties as are
specifically set forth in this Guarantee Agreement, and no implied covenants shall be read into
this Guarantee Agreement against the Guarantee Trustee. In case an Event of Default has occurred
(that has not been cured or waived pursuant to Section 2.6(a)), the Guarantee Trustee shall
exercise such of the rights and powers vested in it by this Guarantee Agreement, and use the same
degree of care and skill in their exercise, as a prudent person would exercise or use under the
circumstances in the conduct of his or her own affairs.



     (b) No provision of this Guarantee Agreement shall be construed to relieve the Guarantee
Trustee from liability for its own negligent action, its own negligent failure to act or its own
willful misconduct, except that:




     (i) prior to the occurrence of an Event of Default and after the curing or waiving of
all such Events of Default that may have occurred:




     (A) the duties and obligations of the Guarantee Trustee shall be determined
solely by the express provisions of this Guarantee Agreement, and the Guarantee
Trustee shall not be liable except for the performance of such duties and
obligations as are specifically set forth in this Guarantee Agreement, and no
implied covenants or obligations shall be read into this Guarantee Agreement against
the Guarantee Trustee; and




     (B) in the absence of bad faith on the part of the Guarantee Trustee, the
Guarantee Trustee may conclusively rely, as to the truth of the statements and the
correctness of the opinions expressed therein, upon any certificates or opinions
furnished to the Guarantee Trustee and conforming to the requirements of this
Guarantee Agreement; but in the case of any such certificates or opinions that by
any provision hereof are specifically required to be furnished to the Guarantee
Trustee, the Guarantee Trustee shall be under a duty to examine the same to
determine whether or not they conform to the requirements of this Guarantee
Agreement;




     (ii) the Guarantee Trustee shall not be liable for any error of judgment made in good
faith by a Responsible Officer of the Guarantee Trustee, unless it shall have proved that
the Guarantee Trustee was negligent in ascertaining the pertinent facts;




     (iii) the Guarantee Trustee shall not be liable with respect to any action taken or
omitted to be taken by it in good faith in accordance with the direction of the Holders of
Preferred Securities as provided herein relating to the time, method and place of conducting
any proceeding for any remedy available to the Guarantee Trustee, or exercising any trust or
power conferred upon the Guarantee Trustee under this Guarantee Agreement; and




     (iv) no provision of this Guarantee Agreement shall require the Guarantee Trustee to
expend or risk its own funds or otherwise incur personal financial liability in



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the performance of any of its duties or in the exercise of any of its rights or powers, if it
shall have reasonable ground for believing that the repayment of such funds or liability is
not reasonably assured to it under the terms of this Guarantee Agreement or adequate
indemnity against such risk or liability is not reasonably assured to it.



     (c) Subject to the provisions of Section 3.2(a) and (b):




     (i) Whenever in the administration of this Guarantee Agreement, the Guarantee Trustee
shall deem it desirable that a matter be proved or established prior to taking, suffering or
omitting any action hereunder, the Guarantee Trustee (unless other evidence is herein
specifically prescribed) may, in the absence of bad faith on its part, request and rely upon
a certificate, which shall comply with the provisions of Sec. 314(e) of the Trust Indenture
Act, signed by any authorized officer of the Guarantor;




     (ii) The Guarantee Trustee (A) may consult with counsel (which may be counsel to the
Guarantor or any of its Affiliates and may include any of their respective employees)
selected by it in good faith and with due care and the written advice or opinion of such
counsel with respect to legal matters shall be full and complete authorization and
protection in respect of any action taken, suffered or omitted by it hereunder in good faith
and in reliance thereon and in accordance with such advice and opinion and (B) shall have
the right at any time to seek instructions concerning the administration of this Guarantee
Agreement from any court of competent jurisdiction;




     (iii) The Guarantee Trustee may execute any of the trusts or powers hereunder or
perform any duties hereunder either directly or by or through agents or attorneys and the
Guarantee Trustee shall not be responsible for any misconduct or negligence on the part of
any agent or attorney appointed by it in good faith and with due
care;



     (iv) The Guarantee Trustee shall be under no obligation to exercise any of the rights
or powers vested in it by this Guarantee Agreement at the request or direction of any
Holders of Preferred Securities, unless such Holders shall have offered to the Guarantee
Trustee reasonable security and indemnity against the costs, expenses (including attorneys’
fees and expenses) and liabilities that might be incurred by it in complying with such
request or direction; provided that nothing contained in this clause (iv) shall relieve the Guarantee Trustee of the obligation, upon the occurrence of an
Event of Default (which has not been cured or waived) to exercise such of the rights and
powers vested in it by this Guarantee Agreement, and to use the same degree of care and
skill in this exercise, as a prudent person would exercise or use under the circumstances in
the conduct of his or her own affairs; and




     (v) Any action taken by the Guarantee Trustee or its agents hereunder shall bind the
Holders of the Preferred Securities and the signature of the Guarantee Trustee or its agents
alone shall be sufficient and effective to perform any such action; and no third party shall
be required to inquire as to the authority of the Guarantee Trustee to so act, or as to its
compliance with any of the terms and provisions of this Guarantee Agreement, both of which
shall be conclusively evidenced by the Guarantee Trustee’s or its agent’s taking such
action.



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SECTION 3.3 Not Responsible for Recitals or Issuance of Guarantee.




     The recitals contained in this Guarantee Agreement shall be taken as the statements of the
Guarantor and the Guarantee Trustee does not assume any responsibility for their correctness. The
Guarantee Trustee makes no representations as to the validity or sufficiency of this Guarantee
Agreement.



ARTICLE IV




GUARANTEE TRUSTEE




SECTION 4.1 Qualifications.




     (a) There shall at all times be a Guarantee Trustee which shall:




     (i) not be an Affiliate of the Guarantor; and




     (ii) be a corporation organized and doing business under the laws of the United States
of America or any State or Territory thereof or of the District of Columbia, or a
corporation or Person permitted by the Commission to act as an institutional trustee under
the Trust Indenture Act, authorized under such laws to exercise corporate trust powers,
having a combined capital and surplus of at least $50,000,000, and subject to supervision or
examination by Federal, State, Territorial or District of Columbia authority. If such
corporation publishes reports of condition at least annually, pursuant to law or to the
requirements of the supervising or examining authority referred to above, then for the
purposes of this Section 4.1(a)(ii), the combined capital and surplus of such corporation
shall be deemed to be its combined capital and surplus as set forth in its most recent
report of condition so published.



     If at any time the Guarantee Trustee shall cease to satisfy the requirements of clauses
(i)-(ii) above, the Guarantee Trustee shall immediately resign in the manner and with the effect
set out in Section 4.2. If the Guarantee Trustee has or shall acquire any “conflicting interest”
within the meaning of Sec. 310(b) of the Trust Indenture Act, the Guarantee Trustee and the
Guarantor shall in all respects comply with the provisions of Sec. 310(b) of the Trust Indenture
Act.



     Any corporation into which the Guarantee Trustee may be merged or converted or with which it
may be consolidated, or any corporation resulting from any merger, conversion or consolidation to
which the Guarantee Trustee shall be a party, or any corporation succeeding to all or substantially
all the corporate trust business of the Guarantee Trustee, shall be a Successor Guarantee Trustee
hereunder, provided such corporation shall be otherwise qualified and eligible under this Article
without the execution or filing of any paper or any further act on the part of any of the parties
hereto.



SECTION 4.2 Appointment, Removal and Resignation of Guarantee Trustee.




     (a) Subject to Section 4.2(b), the Guarantee Trustee may be appointed or removed without cause
at any time by the Guarantor.



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     (b) The Guarantee Trustee shall not be removed in accordance with Section 4.2(a) until a
Successor Guarantee Trustee possessing the qualifications to act as Guarantee Trustee under Section
4.1(a) has been appointed and has accepted such appointment by written instrument executed by such
Successor Guarantee Trustee and delivered to the Guarantor.



     (c) The Guarantee Trustee appointed to office shall hold office until his successor shall have
been appointed or until its removal or resignation.



     (d) The Guarantee Trustee may resign from office (without need for prior or subsequent
accounting) by an instrument (a “Resignation Request”) in writing signed by the Guarantee Trustee
and delivered to the Guarantor, which resignation shall take effect upon such delivery or upon such
later date as is specified therein; provided, however, that no such resignation of
the Guarantee Trustee shall be effective until a Successor Guarantee Trustee possessing the
qualifications to act as Guarantee Trustee under Section 4.1(a) has been appointed and has accepted
such appointment by instrument executed by such Successor Guarantee Trustee and delivered to
Guarantor and the resigning Guarantee Trustee.



     (e) If no Successor Guarantee Trustee shall have been appointed and accepted appointment as
provided in this Section 4.2 within 60 days after delivery to the Guarantor of a Resignation
Request, the resigning Guarantee Trustee may petition any court of competent jurisdiction for
appointment of a Successor Guarantee Trustee. Such court may thereupon after such notice, if any,
as it may deem proper and prescribe, appoint a Successor Guarantee Trustee.



ARTICLE V




GUARANTEE




SECTION 5.1 Guarantee.




     The Guarantor irrevocably and unconditionally agrees to pay in full to the Holders the
Guarantee Payments (without duplication of amounts theretofore paid by the Issuer) as and when due,
to the Holders of record as of the date upon which such Guarantee Payments are due, regardless of
any defense, right of set-off or counterclaim which the Issuer may have or assert. The Guarantor’s
obligation to make a Guarantee Payment may be satisfied by direct payment of the required amounts
by the Guarantor to the Holders or by causing the Issuer to pay such amounts to the Holders.



SECTION 5.2 Waiver of Notice.




     The Guarantor hereby waives notice of acceptance of this Guarantee Agreement and of any
liability to which it applies or may apply, presentment, demand for payment, any right to require a
proceeding first against the Issuer or any other Person before proceeding against the Guarantor,
protest, notice of nonpayment, notice of dishonor, notice of redemption and all other notices and
demands. Notwithstanding anything to the contrary herein, the Guarantor retains all of its rights
to (i) extend the interest payment period on the Notes and the Guarantor shall not be obligated
hereunder to make any Guarantee Payments during any extended interest payment period with respect
to the Distributions (as defined in the Declaration) on the Preferred Securities



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and (ii) redeem or
change the maturity date of the Notes, in each case to the extent permitted by the Indenture.



SECTION 5.3 Obligations Not Affected.




     The obligations, covenants, agreements and duties of the Guarantor under this Guarantee
Agreement shall in no way be affected or impaired by reason of the happening from time to time of
any of the following:



     (a) the release or waiver, by operation of law or otherwise, of the performance or observance
by the Issuer of any express or implied agreement, covenant, term or condition relating to the
Preferred Securities to be performed or observed by the Issuer;



     (b) the extension of time for the payment by the Issuer of all or any portion of the
Distributions (other than an extension of time for payment of Distributions that results from the
extension of any interest payment period on the Notes), Redemption Price, Liquidation Distribution
or any other sums payable under the terms of the Preferred Securities or the
extension of time for the performance of any other obligation under, arising out of, or in
connection with, the Preferred Securities;



     (c) any failure, omission, delay or lack of diligence on the part of the Holders to enforce,
assert or exercise any right, privilege, power or remedy conferred on the Holders pursuant to the
terms of the Preferred Securities, or any action on the part of the Issuer granting indulgence or
extension of any kind;



     (d) the voluntary or involuntary liquidation, dissolution, sale of any collateral,
receivership, insolvency, bankruptcy, assignment for the benefit of creditors, reorganization,
arrangement, composition or readjustment of debt of, or other similar proceedings affecting, the
Issuer or any of the assets of the Issuer;



     (e) any invalidity of, or defect or deficiency in, the Preferred Securities;



     (f) the settlement or compromise of any obligation guaranteed hereby or hereby incurred; or



     (g) any other circumstance whatsoever that might otherwise constitute a legal or equitable
discharge or defense of a guarantor, it being the intent of this Section 5.3 that the obligations
of the Guarantor hereunder shall be absolute and unconditional under any and all circumstances.
There shall be no obligation of the Holders to give notice to, or obtain consent of, the Guarantor
with respect to the happening of any of the foregoing.



SECTION 5.4 Enforcement of Guarantee.




     The Guarantor and the Guarantee Trustee expressly acknowledge that (i) this Guarantee
Agreement will be deposited with the Guarantee Trustee to be held for the benefit of the Holders;
(ii) the Guarantee Trustee has the right to enforce this Guarantee Agreement on behalf of the
Holders; (iii) Holders representing not less than a Majority in liquidation amount of the Preferred
Securities have the right to direct the time, method and place of conducting any proceeding for



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any remedy available in respect of this Guarantee Agreement including the giving of directions to the
Guarantee Trustee, or exercising any trust or other power conferred upon the Guarantee Trustee
under this Guarantee Agreement; and (iv) any Holder may institute a legal proceeding directly
against the Guarantor to enforce such Holder’s rights under this Guarantee Agreement, without first
instituting a legal proceeding against the Issuer, the Guarantee Trustee, or any other Person.



SECTION 5.5 Guarantee of Payment.




     This Guarantee Agreement creates a guarantee of payment and not merely of collection. This
Guarantee Agreement will not be discharged except by payment of the Guarantee Payments in full
(without duplication of amounts theretofore paid by the Issuer).



SECTION 5.6 Subrogation.




     The Guarantor shall be subrogated to all (if any) rights of the Holders against the Issuer in
respect of any amounts paid to the Holders by the Guarantor under this Guarantee Agreement;
provided, however, that the Guarantor shall not (except to the extent required by
mandatory provisions of law) be entitled to enforce or exercise any rights which it may acquire by
way of subrogation or any indemnity, reimbursement or other agreement, in all cases as a result of
payment under this Guarantee Agreement, if, at the time of any such payment, any amounts are due
and unpaid under this Guarantee Agreement. If any amount shall be paid to the Guarantor in
violation of the preceding sentence, the Guarantor agrees to hold such amount in trust for the
Holders and to pay over such amount to the Holders.



SECTION 5.7 Independent Obligations.




     The Guarantor acknowledges that its obligations hereunder are independent of the obligations
of the Issuer with respect to the Preferred Securities and that the Guarantor shall be liable as
principal and as debtor hereunder to make Guarantee Payments pursuant to the terms of this
Guarantee Agreement notwithstanding the occurrence of any event referred to in subsections (a)
through (g), inclusive, of Section 5.3 hereof.



ARTICLE VI




LIMITATION OF TRANSACTIONS; SUBORDINATION




SECTION 6.1 Limitation of Transactions.




     So long as any Preferred Securities remain outstanding, the Guarantor will not declare or pay
any dividend on, or redeem, purchase, acquire or make a distribution or liquidation payment with
respect to, any of its common stock or preferred stock, or any other securities similar to the
Preferred Securities or the Notes, or make any guarantee payments with respect thereto, if at such
time (i) the Guarantor shall be in default with respect to its Guarantee Payments or other payment
obligations hereunder, (ii) there shall have occurred and be continuing any event of default under
the Indenture or (iii) the Guarantor shall have given notice of its selection of an Extension
Period (as defined in the Indenture) and such period, or any extension thereof, is continuing;
provided that the Guarantor will be permitted to pay dividends (and cash in lieu of



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fractional shares) upon the mandatory conversion of any of its preferred stock in accordance with the terms of
such stock. In addition, so long as any Preferred Securities remain outstanding, the Guarantor (i)
will remain the sole direct or indirect owner of all of the outstanding Common Securities and shall
not cause or permit the Common Securities to be transferred except to the extent such transfer is
permitted under Section 5.10 of the Declaration; provided that any permitted successor of the
Guarantor under the Indenture may succeed to the Guarantor’s ownership of the Common Securities and
(ii) will not take any action which would cause the Issuer to cease to be treated as a grantor trust for United States federal income tax purposes
except in connection with a distribution of Notes as provided in the Declaration.



SECTION 6.2 Subordination.




     This Guarantee Agreement will constitute an unsecured obligation of the Guarantor and will
rank (i) subordinate and junior in right of payment to all other liabilities of the Guarantor,
including the Notes, except those made pari passu or subordinate by their terms, and (ii) senior to
all capital stock now or hereafter issued by the Guarantor and to any guarantee now or hereafter
entered into by the Guarantor in respect of any of its capital stock.



ARTICLE VII




TERMINATION




SECTION 7.1 Termination.




     This Guarantee Agreement shall terminate and be of no further force and effect upon full
payment of the Redemption Price of all Preferred Securities, upon the distribution of Notes to
Holders of Preferred Securities and Common Securities in exchange for all of the Preferred
Securities and Common Securities or upon full payment of the amounts payable in accordance with the
Declaration upon liquidation of the Issuer. Notwithstanding the foregoing, this Guarantee
Agreement will continue to be effective or will be reinstated, as the case may be, if at any time
any Holder must restore payment of any sums paid with respect to the Preferred Securities or this
Guarantee Agreement.



ARTICLE VIII




LIMITATION OF LIABILITY; INDEMNIFICATION




SECTION 8.1 Exculpation.




     (a) No Indemnified Person shall be liable, responsible or accountable in damages or otherwise
to the Guarantor or any Covered Person for any loss, damage or claim incurred by reason of any act
or omission performed or omitted by such Indemnified Person in good faith and in a manner such
Indemnified Person reasonably believed to be within the scope of the authority conferred on such
Indemnified Person by this Guarantee Agreement or by law, except that an Indemnified Person shall
be liable for any such loss, damage or claim incurred by reason of such Indemnified Person’s
negligence or willful misconduct with respect to such acts or omissions.



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     (b) An Indemnified Person shall be fully protected in relying in good faith upon the records
of the Guarantor and upon such information, opinions, reports or statements presented to the
Guarantor by any Person as to matters the Indemnified Person reasonably believes are within such
other Person’s professional or expert competence and who has been selected with reasonable care by
or on behalf of the Guarantor, including information, opinions, reports or statements as to the
value and amount of the assets, liabilities, profits, losses, or any other facts pertinent to the
existence and amount of assets from which Distributions to Holders of Preferred Securities might
properly be paid.



SECTION 8.2 Indemnification.




     (a) To the fullest extent permitted by applicable law, the Guarantor shall indemnify and hold
harmless each Indemnified Person from and against any loss, damage or claim incurred by such
Indemnified Person by reason of any act or omission performed or omitted by such Indemnified Person
in good faith and in a manner such Indemnified Person reasonably believed to be within the scope of
authority conferred on such Indemnified Person by this Guarantee Agreement, except that no
Indemnified Person shall be entitled to be indemnified in respect of any loss, damage or claim
incurred by such Indemnified Person by reason of negligence or willful misconduct with respect to
such acts or omissions.



     (b) To the fullest extent permitted by applicable law, expenses (including legal fees)
incurred by an Indemnified Person in defending any claim, demand, action, suit or proceeding shall,
from time to time, be advanced by the Guarantor prior to the final disposition of such claim,
demand, action, suit or proceeding upon receipt by the Guarantor of an undertaking by or on behalf
of the Indemnified Person to repay such amount if it shall be determined that the Indemnified
Person is not entitled to be indemnified as authorized in Section 8.2(a).



ARTICLE IX




MISCELLANEOUS




SECTION 9.1 Successors and Assigns.




     All guarantees and agreements contained in this Guarantee Agreement shall bind the successors,
assigns, receivers, trustees and representatives of the Guarantor and shall inure to the benefit of
the Holders of the Preferred Securities then outstanding. Except in connection with a
consolidation, merger or sale involving the Guarantor that is permitted under Article Eight of the
Indenture, the Guarantor shall not assign its obligations hereunder.



SECTION 9.2 Amendments.




     Except with respect to any changes which do not adversely affect the rights of Holders (in
which case no consent of Holders will be required), this Guarantee Agreement may only be amended
with the prior approval of the Holders of not less than a Majority in liquidation amount of the
Preferred Securities. The provisions of Article 6 of the Declaration concerning meetings of
Holders shall apply to the giving of such approval.



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SECTION 9.3 Notices.




     Any notice, request or other communication required or permitted to be given hereunder shall
be in writing, duly signed by the party giving such notice, and delivered, telecopied or mailed by
first class mail as follows:



     (a) if given to the Guarantor, to the address set forth below or such other address as the
Guarantor may give notice to the Holders:


Odyssey Re Holdings Corp.

300 First Stamford Place

Stamford, Connecticut 06902

Facsimile No.: (203) 965-7960

Attention: Donald L. Smith, Senior Vice President, General Counsel

and Corporate Secretary




     (b) if given to the Guarantee Trustee, to the address set forth below or such other address as
the Guarantee Trustee may give notice to the Holders:


The Bank of New York Mellon

101 Barclay Street, Floor 21W

New York, New York 10286

Attention: Corporate Trust Trustee Administration




     (c) if given to any Holder of Preferred Securities, at the address set forth on the books and
records of the Issuer.



     All notices hereunder shall be deemed to have been given when received in person, telecopied
with receipt confirmed, or mailed by first class mail, postage prepaid except that if a notice or
other document is refused delivery or cannot be delivered because of a changed address of which no
notice was given, such notice or other document shall be deemed to have been delivered on the date
of such refusal or inability to deliver.



SECTION 9.4 Genders.




     The masculine, feminine and neuter genders used herein shall include the masculine, feminine
and neuter genders.



SECTION 9.5 Benefit.




     This Guarantee Agreement is solely for the benefit of the Holders and subject to Section
3.1(a) is not separately transferable from the Preferred Securities.



SECTION 9.6 Governing Law.




     THIS GUARANTEE AGREEMENT SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAWS OF THE
STATE OF NEW YORK.



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SECTION 9.7 Counterparts.




     This Guarantee Agreement may be executed in counterparts, each of which shall be an original;
but such counterparts shall together constitute one and the same instrument.



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     THIS GUARANTEE AGREEMENT is executed as of the day and year first above written.



	 	 	 	 	 	 	 
	 	 	ODYSSEY RE HOLDINGS CORP.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	Name:
	 	 

	 	 
	 

	 	Title:	 	 	 	 
	 
	 	 	 	 	 	 
	 	 	THE BANK OF NEW YORK MELLON,	 	 
	 	 	as Guarantee Trustee	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	Name:
	 	 

	 	 
	 

	 	Title:	 	 	 	 







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