<PAGE>
                                                                       EX- 10.37

                              SEPARATION AGREEMENT
                              --------------------

          THIS SEPARATION AGREEMENT, dated as of May 2, 2005 (the "Agreement"),
by and between ODYSSEY RE HOLDINGS CORP. (the "Company") and Charles Troiano
(the "Executive").

          WHEREAS, the Executive has decided to retire from his position as
Executive Vice President and Chief Financial Officer of the Company;

          WHEREAS, the parties intend that this Agreement shall set forth the
terms of the Executive's retirement and that this Agreement shall supersede all
prior agreements between the parties regarding the subject matter contained
herein.

          NOW, THEREFORE, in consideration of the covenants and agreements
hereinafter set forth in this Agreement, the parties hereto hereby agree as
follows:

          1.   Resignation. The Executive hereby resigns from his position as
Chief Financial Officer of the Company, effective as of March 31, 2005 (the
"Effective Date"). From the Effective Date up to and including May 15, 2005, the
Executive shall serve as an Executive Vice President of the Company and assist
in the transition of his duties as Chief Financial Officer of the Company.
Effective as of the close of business on May 15, 2005, the Executive shall
resign from his position as Executive Vice President of the Company and from all
other offices, positions and capacities.

          2.   Payments and Benefits. In consideration of the Executive's
continuing performance of services for the Company and the waiver and release of
claims set forth below, and provided that the Executive does not revoke this
Agreement during the Revocation Period (as defined below), the Company shall
provide the Executive with the following payments and benefits:

          (a)  Base Salary. The Company shall continue to pay the Executive his
base salary as in effect on the Effective Date up to and including May 15, 2005.

          (b)  Restricted Stock. In connection with the Executive's employment
with the Company, the Company granted the Executive shares of restricted common
stock pursuant to the Company's 2001 Restricted Share Plan (the "Plan"). 27,980
shares of such restricted common stock shall vest in two equal installments on
(i) May 15, 2005 and (ii) April 1, 2006 and shall otherwise be subject to the
terms of the Plan and any applicable award agreements. Except as provided in the
previous sentence, any other shares of restricted common stock of the Company
granted to the Executive shall be forfeited without any payment to the
Executive, effective as of the close of business on May 15, 2005.

          (c)  Options. The Executive may exercise 17,250 vested stock options
granted to him under the Odyssey Re Holdings Corp. 2002 Stock Incentive Plan
(the "Stock Plan") in accordance with the terms of the Stock Plan and any
applicable award agreements. All unvested stock options granted to the Executive
under the Stock Plan shall be forfeited without any payment to the Executive,
effective as of the close of business on May 15, 2005.



<PAGE>


          (d)  No Other Compensation or Benefits. Except as otherwise
specifically provided herein or as required by Section 4980B(f) of the Internal
Revenue Code of 1986, as amended (relating to "COBRA" coverage) or other
applicable law, the Executive shall not be entitled to any compensation or
benefits or to participate in any past, present or future employee benefit
programs or arrangements of the Company (including, without limitation, any
compensation or benefits under any severance plan, program or arrangement) on or
after May 15, 2005; provided, however, that nothing herein shall be construed to
affect the Executive's right to his vested accounts under the Odyssey America
Reinsurance Corporation Profit Sharing Plan and the Odyssey America Reinsurance
Corporation 401(k) Excess Plan, pursuant to the terms of such plans.

          3.   Return of Property. On or prior to May 15, 2005, the Executive
shall surrender to the Company all property of the Company or its subsidiaries
or affiliates (the "Company Group") in the Executive's possession and all
property made available to the Executive in connection with his employment by
the Company, including, without limitation, any and all Company credit cards,
keys, security access codes, records, manuals, customer lists, notebooks,
computers, computer programs and files, papers, electronically stored
information and documents kept or made by the Executive in connection with his
employment; provided, however, that the Executive may retain the Company's
facsimile machine that he currently uses from his home.

          4.   Cooperation. From and after the Effective Date, the Executive
shall cooperate in all reasonable respects with the Company Group and their
respective directors, officers, attorneys and experts in connection with the
conduct of any action, proceeding, investigation or litigation involving the
Company Group, including any such action, proceeding, investigation or
litigation in which the Executive is called to testify.

          5.   Confidentiality. The Executive agrees that all confidential and
proprietary information relating to the business of the Company Group shall be
kept and treated as confidential both during and after his employment with the
Company, except as may be permitted in writing by the Company's Board or as such
information is within the public domain or comes within the public domain
without any breach of this Agreement. The phrase "confidential and proprietary
information" shall not include information that (i) is or becomes generally
available to the public other than as a result of a disclosure by, or at the
direction of, the Executive or (ii) becomes available to the Executive on a
non-confidential basis from a source other than the Company or any of its
representatives, provided that such source is not known to the Executive to be
bound by a confidentiality agreement with or other contractual, legal or
fiduciary obligation of confidentiality to the Company with respect to such
information.

          6.   Exclusive Property. The Executive confirms that all confidential
information is and shall remain the exclusive property of the Company. All
business records, papers and documents kept or made by the Executive relating to
the business of the Company Group shall be and remain the property of the
Company.



                                       2
<PAGE>


          7.   Certain Remedies.

          (a)  Remedies. Without intending to limit the remedies available to
the Company Group, the Executive agrees that a breach of any of the covenants
contained in this Agreement may result in material and irreparable injury to the
Company Group for which there is no adequate remedy at law, that it will not be
possible to measure damages for such injuries precisely and that, in the event
of such a breach or threat thereof, any member of the Company Group shall be
entitled to seek a temporary restraining order or a preliminary or permanent
injunction, or both, without bond or other security, restraining the Executive
from engaging in activities prohibited by the covenants contained in this
Agreement or such other relief as may be required specifically to enforce any of
the covenants contained in this Agreement. Such injunctive relief in any court
shall be available to the Company Group in lieu of, or prior to or pending
determination in, any arbitration proceeding.

          8.   Release.

          (a)  General Release. In consideration of the payments and benefits
provided to the Executive under this Agreement and after consultation with
counsel, the Executive, and each of the Executive's respective heirs, executors,
administrators, representatives, agents, successors and assigns (collectively,
the "Releasors") hereby irrevocably and unconditionally release and forever
discharge the Company Group and each of their respective officers, employees,
directors, shareholders and agents from any and all claims, actions, causes of
action, rights, judgments, obligations, damages, demands, accountings or
liabilities of whatever kind or character (collectively, "Claims"), including,
without limitation, any Claims under any federal, state, local or foreign law,
that the Releasors may have, or in the future may possess, arising out of (i)
the Executive's employment relationship with and service as an employee or
officer of the Company Group, and the termination of such relationship or
service or (ii) any event, condition, circumstance or obligation that occurred,
existed or arose on or prior to the date hereof; provided, however, that the
release set forth in this Section 8(a) shall not apply to the obligations of the
Company under this Agreement. The Releasors further agree that the payments and
benefits described in this Agreement shall be in full satisfaction of any and
all Claims for payments or benefits, whether express or implied, that the
Releasors may have against the Company Group arising out of the Executive's
employment relationship or the Executive's service as an employee or officer of
the Company Group and the termination thereof.

          (b)  Specific Release of ADEA Claims. In further consideration of the
payments and benefits provided to the Executive under this Agreement, the
Releasors hereby unconditionally release and forever discharge the Company
Group, and each of their respective officers, employees, directors, shareholders
and agents from any and all Claims that the Releasors may have as of the date
the Executive signs this Agreement arising under the Federal Age Discrimination
in Employment Act of 1967, as amended, and the applicable rules and regulations
promulgated thereunder ("ADEA"). By signing this Agreement, the Executive hereby
acknowledges and confirms the following: (i) the Executive was advised by the
Company in connection with his termination to consult with an attorney of his
choice prior to signing this Agreement and to have such attorney explain to the
Executive the terms of this Agreement, including, without limitation, the terms
relating to the Executive release of claims arising under ADEA and, the
Executive has in fact consulted with an attorney; (ii) the Executive was given a
period of not fewer than 21 days to consider the terms of this Agreement and to
consult with an attorney of his choosing with respect thereto; (iii) the
Executive is providing the release and discharge set forth in this Section 8(b)
only in exchange for consideration in addition



                                       3
<PAGE>


to anything of value to which the Executive is already entitled; and (iv) that
the Executive knowingly and voluntarily accepts the terms of this Agreement.

          (c)  No Assignment. The Executive represents and warrants that he has
not assigned any of the Claims being released under this Section 8.

          (d)  Claims. The Executive agrees that he has not instituted, assisted
or otherwise participated in connection with, any action, complaint, claim,
charge, grievance, arbitration, lawsuit, or administrative agency proceeding, or
action at law or otherwise against any member of the Company Group or any of
their respective officers, employees, directors, shareholders or agents.

          (e)  Release by the Company. In consideration of the covenants
provided by the Executive under this Agreement, the Company hereby releases,
waives, discharges and gives up any and all rights which it may have against the
Executive arising out of (a) the Executive's employment with the Company or the
termination thereof or (b) any other matter, cause or thing whatsoever from the
first date of the Executive's employment to the Effective Date; provided,
however, notwithstanding the generality of the foregoing, nothing herein shall
be deemed to release the Executive from (A) any rights or claims of the Company
arising out of or attributable to (i) the Executive's actions or omissions
involving or arising from fraud, deceit, theft or intentional or gross negligent
conduct or violations of any law, rule statute or regulation while employed by
the Company and (ii) the Executive's actions or omissions taken or not taken in
bad faith with respect to the Company; and (B) the Executive's obligations under
this Agreement.


          9.   Miscellaneous.

          (a)  Entire Agreement. This Agreement sets forth the entire agreement
and understanding of the parties hereto with respect to the matters covered
hereby and supersedes and replaces any express or implied, written or oral,
prior agreement or plans or arrangement with respect to the terms of the
Executive's employment and the termination thereof which the Executive may have
had with the Company Group, including without limitation the Employment
Agreement. This Agreement may be amended only by a written document signed by
the parties hereto.

          (b)  Withholding Taxes. Any payments made or benefits provided to the
Executive under this Agreement shall be reduced by any applicable withholding
taxes.

          (c)  Indemnification. Notwithstanding any provision herein to the
contrary, the Indemnification Agreement between the Executive and the Company
dated as of October 1, 2001, which is attached as Exhibit A, is incorporated by
reference into this Agreement and shall continue in full force and effect in
accordance with its terms.

          (d)  Governing Law. This Agreement shall be governed by, and construed
in accordance with, the laws of the State of New York, without giving effect to
the conflicts of laws principles thereof.

          (e)  Waiver. The failure of any party to this Agreement to enforce any
of its terms, provisions or covenants shall not be construed as a waiver of the
same or of the right of


                                       4
<PAGE>

such party to enforce the same. Waiver by any party hereto of any breach or
default by another party of any term or provision of this Agreement shall not
operate as a waiver of any other breach or default.

          (f)  Severability. In the event that any one or more of the provisions
of this Agreement shall be held to be invalid, illegal or unenforceable, the
validity, legality and enforceability of the remainder of the Agreement shall
not in any way be affected or impaired thereby. Moreover, if any one or more of
the provisions contained in this Agreement shall be held to be excessively broad
as to duration, activity or subject, such provisions shall be construed by
limiting and reducing them so as to be enforceable to the maximum extent allowed
by applicable law.

          (g)  Notices. Any notices required or made pursuant to this Agreement
shall be in writing and shall be deemed to have been given when delivered or
mailed by United States certified mail, return receipt requested, postage
prepaid, as follows:

               IF TO THE EXECUTIVE:

               Mr. Charles Troiano
               30 Cortland Place
               Oxford, Connecticut  06478

               IF TO THE COMPANY:

               Odyssey Re Holdings Corp.
               300 First Stamford Place
               Stamford, CT  06902

               ATTN:  Donald L. Smith, Esq.

               WITH A COPY TO:

               John A. Morrison, Esq.
               Shearman & Sterling LLP
               599 Lexington Avenue
               New York, New York 10022

or to such other address as either party may furnish to the other in writing in
accordance with this Section 9(f). Notices of change of address shall be
effective only upon receipt.

          (h)  Descriptive Headings. The paragraph headings contained herein are
for reference purposes only and shall not in any way affect the meaning or
interpretation of this Agreement.

          (i)  Counterparts. This Agreement may be executed in one or more
counterparts, which, together, shall constitute one and the same agreement.



                                       5
<PAGE>


          (j)  Successors and Assigns. Except as otherwise provided herein, this
Agreement shall inure to the benefit of and be enforceable by the Executive and
the Company and their respective successors and assigns.

          (k)  Arbitration. Any dispute or controversy arising under or in
connection with this Agreement that cannot be mutually resolved by the parties
hereto shall be settled exclusively by arbitration in New York, New York under
the employment arbitration rules of the American Arbitration Association before
a single arbitrator of exemplary qualifications and stature, who shall be
selected jointly by the Company and the Executive, or, if the Company and the
Executive cannot agree on the selection of the arbitrator, shall be selected by
the American Arbitration Association. Judgment may be entered on the
arbitrator's award in any court having jurisdiction. The parties hereby agree
that the arbitrator shall be empowered to enter an equitable decree mandating
specific enforcement of the terms of this Agreement.

          10.  Revocation. This Agreement may be revoked by the Executive within
the seven (7)-day period commencing on the date the Executive signs this
Agreement (the "Revocation Period"). In the event of any such revocation by the
Executive, all obligations of the parties under this Agreement shall terminate
and be of no further force and effect as of the date of such revocation. No such
revocation by the Executive shall be effective unless it is in writing and
signed by the Executive and received by the Company prior to the expiration of
the Revocation Period.

          IN WITNESS WHEREOF, the Company has executed this Agreement as of the
date first set forth above and the Executive has executed this Agreement as of
the date set forth below.


                                       ODYSSEY RE HOLDINGS CORP.



                                       By: /s/ Donald L. Smith
                                           -------------------------------------
                                       Name:  Donald L. Smith
                                       Title: Senior Vice President


THE EXECUTIVE HEREBY ACKNOWLEDGES THAT THE EXECUTIVE HAS READ THIS AGREEMENT,
THAT THE EXECUTIVE FULLY KNOWS, UNDERSTANDS AND APPRECIATES ITS CONTENTS, AND
THAT THE EXECUTIVE HEREBY ENTERS INTO THIS AGREEMENT VOLUNTARILY AND OF HIS OWN
FREE WILL.



ACCEPTED AND AGREED:



/s/ Charles Troiano
----------------------------------------
Charles Troiano

Date:    May 2, 2005
     -----------------------------------



                                       6
<PAGE>


                            INDEMNIFICATION AGREEMENT

          This Indemnification Agreement ("Agreement") is entered into as of
October 1, 2001 by and between Odyssey Re Holdings Corp., a Delaware
corporation, (the "Company") and Charles D. Troiano ("Indemnitee").

                                    RECITALS

     (A)  The Company and Indemnitee recognize the continued difficulty in
obtaining liability insurance for its directors, officers, employees, agents and
fiduciaries, the significant increases in the cost of such insurance and the
general reductions in the coverage of such insurance.

     (B)  The Company and Indemnitee further recognize the substantial increase
in corporate litigation in general, subjecting directors, officers, employees,
agents and fiduciaries to expensive litigation risks at the same time as the
availability and coverage of liability insurance has been severely limited.

     (C)  Indemnitee does not regard the current protection available as
adequate under the present circumstances, and Indemnitee and other directors,
officers, employees, agents and fiduciaries of the Company may not be willing to
continue to serve in such capacities without additional protection.

     (D)  The Company desires to attract and retain the services of highly
qualified individuals, such as Indemnitee, to serve the Company and, in part, in
order to induce Indemnitee to continue to provide services to the Company,
wishes to provide for the indemnification and advancing of expenses to
Indemnitee to the maximum extent permitted by law.

     (E)  In view of the considerations set forth above, the Company desires
that Indemnitee be indemnified by the Company as set forth herein.

          NOW, THEREFORE, the Company and Indemnitee hereby agree as follows:

          1.   Indemnification.

          (a)  Indemnification of Expenses. The Company shall indemnify
Indemnitee to the fullest extent permitted by law if Indemnitee was or is or
becomes a party to or witness or other participant in, or is threatened to be
made a party to or witness or other participant in, any threatened, pending or
completed action, suit, proceeding or alternative dispute resolution mechanism,
or any hearing, inquiry or investigation that Indemnitee in good faith believes
might lead to the institution of any such action, suit, proceeding or
alternative dispute resolution mechanism, whether civil, criminal,
administrative, investigative or other (hereinafter a "Claim") by reason of (or
arising in part out of) any event or occurrence related to the fact that
Indemnitee is or was a director, officer, employee, agent or fiduciary of the
Company, or any subsidiary of the Company, or is or was serving at the request
of the Company as a director, officer, employee, agent or fiduciary of another
corporation, partnership, joint venture, trust or other enterprise, or by reason
of any action or inaction on the part of Indemnitee while serving in such
capacity



<PAGE>


(hereinafter an "Indemnifiable Event") against any and all expenses (including
attorneys' fees and all other costs, expenses and obligations incurred in
connection with investigating, defending, being a witness in or participating in
(including on appeal), or preparing to defend, be a witness in or participate
in, any such action, suit, proceeding, alternative dispute resolution mechanism,
hearing, inquiry or investigation), judgments, fines, penalties and amounts paid
in settlement (if such settlement is approved in advance by the Company, which
approval shall not be unreasonably withheld) of such Claim and any federal,
state, local or foreign taxes imposed on Indemnitee as a result of the actual or
deemed receipt of any payments under this Agreement (collectively, hereinafter
"Expenses"), including all interest, assessments and other charges paid or
payable in connection with or in respect of such Expenses. Such payment of
Expenses shall be made by the Company as soon as practicable but in any event no
later than five days after written demand by Indemnitee therefor is presented to
the Company.

          (b)  Reviewing Party. Notwithstanding the foregoing, (i) the
obligations of the Company under Section 1(a) shall be subject to the condition
that the Reviewing Party (as described in Section 10(e) hereof) shall not have
determined (in a written opinion, in any case in which the Independent Legal
Counsel referred to in Section 1(c) hereof is involved) that Indemnitee would
not be permitted to be indemnified under applicable law, and (ii) the obligation
of the Company to make an advance payment of Expenses to Indemnitee pursuant to
Section 2(a) (an "Expense Advance") shall be subject to the condition that, if,
when and to the extent that the Reviewing Party determines that Indemnitee would
not be permitted to be so indemnified under applicable law, the Company shall be
entitled to be reimbursed by Indemnitee (who hereby agrees to reimburse the
Company) for all such amounts theretofore paid; provided, however, that if
Indemnitee has commenced or thereafter commences legal proceedings in a court of
competent jurisdiction to secure a determination that Indemnitee should be
indemnified under applicable law, any determination made by the Reviewing Party
that Indemnitee would not be permitted to be indemnified under applicable law
shall not be binding and Indemnitee shall not be required to reimburse the
Company for any Expense Advance until a final judicial determination is made
with respect thereto (as to which all rights of appeal therefrom have been
exhausted or lapsed). Indemnitees' obligation to reimburse the Company for any
Expense Advance shall be unsecured and no interest shall be charged thereon. If
there has not been a Change in Control (as defined in Section 10(c) hereof), the
Reviewing Party shall be selected by the Board of Directors, and if there has
been such a Change in Control (other than a Change in Control which has been
approved by a majority of the Company's Board of Directors who were directors
immediately prior to such Change in Control), the Reviewing Party shall be the
Independent Legal Counsel referred to in Section 1(c) hereof. If there has been
no determination by the Reviewing Party or if the Reviewing Party determines
that Indemnitee substantively would not be permitted to be indemnified in whole
or in part under applicable law, Indemnitee shall have the right to commence
litigation seeking an initial determination by the court or challenging any such
determination by the Reviewing Party or any aspect thereof, including the legal
or factual bases therefor, and the Company hereby consents to service of process
and to appear in any such proceeding. Any determination by the Reviewing Party
otherwise shall be conclusive and binding on the Company and Indemnitee.

          (c)  Change in Control. The Company agrees that if there is a Change
in Control of the Company (other than a Change in Control which has been
approved by a majority of the Company's Board of Directors who were directors
immediately prior to such Change in



                                       2
<PAGE>


Control) then, with respect to all matters thereafter arising concerning the
rights of Indemnitees to payments of Expenses and Expense Advances under this
Agreement or any other agreement or under the Company's Certificate of
Incorporation or Bylaws as now or hereafter in effect, Independent Legal Counsel
(as defined in Section 10(d) hereof) shall be selected by Indemnitee and
approved by the Company (which approval shall not be unreasonably withheld).
Such counsel, among other things, shall render its written opinion to the
Company and Indemnitee as to whether and to what extent Indemnitee would be
permitted to be indemnified under applicable law and the Company agrees to abide
by such opinion. The Company agrees to pay the reasonable fees of the
Independent Legal Counsel referred to above and to fully indemnify such counsel
against any and all expenses (including attorneys' fees), claims, liabilities
and damages arising out of or relating to this Agreement or its engagement
pursuant hereto.

          (d)  Mandatory Payment of Expenses. Notwithstanding any other
provision of this Agreement other than Section 9 hereof, to the extent that
Indemnitee has been successful on the merits or otherwise, including, without
limitation, the dismissal of an action without prejudice, in defense of any
action, suit, proceeding, inquiry or investigation referred to in Section (1)(a)
hereof or in the defense of any claim, issue or matter therein, Indemnitee shall
be indemnified against all Expenses incurred by Indemnitee in connection
therewith.

          2.   Expenses; Indemnification Procedure.

          (a)  Advancement of Expenses. The Company shall advance all Expenses
incurred by Indemnitee. The advances to be made hereunder shall be paid by the
Company to Indemnitee as soon as practicable but in any event no later than five
days after written demand by Indemnitee therefor to the Company.

          (b)  Notice/Cooperation by Indemnitee. Indemnitee shall, as a
condition precedent to Indemnitees' right to be indemnified under this
Agreement, give the Company notice in writing as soon as practicable of any
Claim made against Indemnitee for which indemnification will or could be sought
under this Agreement. Notice to the Company shall be directed to the Chief
Executive Officer of the Company at the address shown on the signature page of
this Agreement (or such other address as the Company shall designate in writing
to Indemnitee). In addition, Indemnitee shall give the Company such information
and cooperation as it may reasonably require and as shall be within Indemnitees'
power.

          (c)  No Presumptions; Burden of Proof. For purposes of this Agreement,
the termination of any Claim by judgment, order, settlement (whether with or
without court approval) or conviction, or upon a plea of nolo contendere, or its
equivalent, shall not create a presumption that Indemnitee did not meet any
particular standard of conduct or have any particular belief or that a court has
determined that indemnification is not permitted by applicable law. In addition,
neither the failure of the Reviewing Party to have made a determination as to
whether Indemnitee has met any particular standard of conduct or had any
particular belief, nor an actual determination by the Reviewing Party that
Indemnitee has not met such standard of conduct or did not have such belief,
prior to the commencement of legal proceedings by Indemnitee to secure a
judicial determination that Indemnitee should be indemnified under applicable
law, shall be a defense to Indemnitee's claim or create a presumption that
Indemnitee has not met any particular standard of conduct or did not have any
particular belief. In



                                       3
<PAGE>

connection with any determination by the Reviewing Party or otherwise as to
whether Indemnitee is entitled to be indemnified hereunder, the burden of proof
shall be on the Company to establish that Indemnitee is not so entitled.

          (d)  Notice to Insurers. If, at the time of the receipt by the Company
of a notice of a Claim pursuant to Section 2(b) hereof, the Company has
liability insurance in effect which may cover such Claim, the Company shall give
prompt notice of the commencement of such Claim to the insurers in accordance
with the procedures set forth in the respective policies. The Company shall
thereafter take all necessary or desirable action to cause such insurers to pay,
on behalf of Indemnitee, all amounts payable as a result of such action, suit,
proceeding, inquiry or investigation in accordance with the terms of such
policies.

          (e)  Selection of Counsel. In the event the Company shall be obligated
hereunder to pay the Expenses of any Claim, the Company shall be entitled to
assume the defense of such Claim with counsel approved by Indemnitee, which
approval shall not be unreasonably withheld, upon the delivery to Indemnitee of
written notice of its election so to do. After delivery of such notice, approval
of such counsel by Indemnitee and the retention of such counsel by the Company,
the Company will not be liable to Indemnitee under this Agreement for any fees
of counsel subsequently incurred by Indemnitee with respect to the same Claim;
provided that, (i) Indemnitee shall have the right to employ Indemnitee's
counsel in any such Claim at Indemnitee's expense and (ii) if (A) the employment
of counsel by Indemnitee has been previously authorized by the Company, (B)
Indemnitee shall have reasonably concluded that there is a conflict of interest
between the Company and Indemnitee in the conduct of any such defense, or (C)
the Company shall not continue to retain such counsel to defend such Claim, then
the fees and expenses of Indemnitee's counsel shall be at the expense of the
Company. The Company shall have the right to conduct such defense as it sees fit
in its sole discretion, including the right to settle any claim against
Indemnitee without the consent of the Indemnitee.

          3.   Additional Indemnification Rights; Nonexclusivity.

          (a)  Scope. The Company hereby agrees to indemnify Indemnitee to the
fullest extent permitted by law, notwithstanding that such indemnification is
not specifically authorized by the other provisions of this Agreement, the
Company's Certificate of Incorporation, the Company's Bylaws or by statute. In
the event of any change after the date of this Agreement in any applicable law,
statute or rule (whether by statute or judicial decision) which expands the
right of a Delaware corporation to indemnify a member of its Board of Directors
or an officer, employee, agent or fiduciary, it is the intent of the parties
hereto that Indemnitee shall enjoy by this Agreement the greater benefits
afforded by such change. In the event of any change in any applicable law,
statute or rule (whether by statute or judicial decision) which narrows the
right of a Delaware corporation to indemnify a member of its Board of Directors
or an officer, employee, agent or fiduciary, such change, to the extent not
otherwise required by such law, statute or rule to be applied to this Agreement,
shall have no effect on this Agreement or the parties' rights and obligations
hereunder except as set forth in Section 8(a) hereof.

          (b)  Nonexclusivity. The indemnification provided by this Agreement
shall be in addition to any rights to which Indemnitee may be entitled under the
Company's Certificate of



                                       4
<PAGE>

Incorporation, its Bylaws, any agreement, any vote of stockholders or
disinterested directors, the General Corporation Law of the State of Delaware,
or otherwise. The indemnification provided under this Agreement shall continue
as to Indemnitee for any action Indemnitee took or did not take while serving in
an indemnified capacity even though Indemnitee may have ceased to serve in such
capacity.

          4.   No Duplication of Payments. The Company shall not be liable under
this Agreement to make any payment in connection with any Claim made against
Indemnitee to the extent Indemnitee has otherwise actually received payment
(under any insurance policy, Certificate of Incorporation, Bylaw or otherwise)
of the amounts otherwise indemnifiable hereunder.

          5.   Partial Indemnification. If Indemnitee is entitled under any
provision of this Agreement to indemnification by the Company for some or a
portion of Expenses incurred in connection with any Claim, but not, however, for
all of the total amount thereof, the Company shall nevertheless indemnify
Indemnitee for the portion of such Expenses to which Indemnitee are entitled.

          6.   Mutual Acknowledgement. Both the Company and Indemnitee
acknowledge that in certain instances, Federal law or applicable public policy
may prohibit the Company from indemnifying its directors, officers, employees,
agents or fiduciaries under this Agreement or otherwise. Indemnitee understands
and acknowledges that the Company has undertaken or may be required in the
future to undertake with the Securities and Exchange Commission to submit the
question of indemnification to a court in certain circumstances for a
determination of the Company's right under public policy to indemnify
Indemnitee.

          7.   Liability Insurance. To the extent the Company maintains
liability insurance applicable to directors, officers, employees, agents or
fiduciaries, Indemnitee shall be covered by such policies in such a manner as to
provide Indemnitee the same rights and benefits as are accorded to the most
favorably insured of the Company's directors, if Indemnitee is a director; or of
the Company's officers, if Indemnitee is not a director of the Company but is an
officer; or of the Company's key employees, agents or fiduciaries, if Indemnitee
is not an officer or director but is a key employee, agent or fiduciary.

          8.   Exceptions. Any other provision herein to the contrary
notwithstanding, the Company shall not be obligated pursuant to the terms of
this Agreement:

          (a)  Excluded Action or Omissions. (i) To indemnify Indemnitee for
Indemnitee's acts, omissions or transactions from which Indemnitee or the
Indemnitee may not be indemnified under applicable law; or (ii) to indemnify
Indemnity for Indemnity's intentional acts or transactions in violation of the
Company's policies;

          (b)  Claims Initiated by Indemnitee. To indemnify or advance expenses
to Indemnitee with respect to Claims initiated or brought voluntarily by
Indemnitee and not by way of defense, except (i) with respect to actions or
proceedings brought to establish or enforce a right to indemnification under
this Agreement or any other agreement or insurance policy or under the Company's
Certificate of Incorporation or Bylaws now or hereafter in effect relating to



                                       5
<PAGE>


Claims for Indemnifiable Events, (ii) in specific cases if the Board of
Directors has approved the initiation or bringing of such Claim, or (iii) as
otherwise required under Section 145 of the Delaware General Corporation Law,
regardless of whether Indemnitee ultimately is determined to be entitled to such
indemnification, advance expense payment or insurance recovery, as the case may
be;

          (c)  Lack of Good Faith. To indemnify Indemnitee for any expenses
incurred by Indemnitee with respect to any proceeding instituted by Indemnitee
to enforce or interpret this Agreement, if a court of competent jurisdiction
determines that each of the material assertions made by Indemnitee in such
proceeding was not made in good faith or was frivolous; or

          (d)  Claims Under Section 16(b). To indemnify Indemnitee for expenses
and the payment of profits arising from the purchase and sale by Indemnitee of
securities in violation of Section 16(b) of the Securities Exchange Act of 1934,
as amended, or any similar successor statute.

          9.   Period of Limitations. No legal action shall be brought and no
cause of action shall be asserted by or in the right of the Company against
Indemnitee, Indemnitee's estate, spouse, heirs, executors or personal or legal
representatives after the expiration of two years from the date of accrual of
such cause of action, and any claim or cause of action of the Company shall be
extinguished and deemed released unless asserted by the timely filing of a legal
action within such two-year period; provided, however, that if any shorter
period of limitations is otherwise applicable to any such cause of action, such
shorter period shall govern.

          10.  Construction of Certain Phrases.

          (a)  For purposes of this Agreement, references to the "Company" shall
include, in addition to the resulting corporation, any constituent corporation
(including any constituent of a constituent) absorbed in a consolidation or
merger which, if its separate existence had continued, would have had power and
authority to indemnify its directors, officers, employees, agents or
fiduciaries, so that if Indemnitee is or was a director, officer, employee,
agent or fiduciary of such constituent corporation, or is or was serving at the
request of such constituent corporation as a director, officer, employee, agent
or fiduciary of another corporation, partnership, joint venture, employee
benefit plan, trust or other enterprise, Indemnitee shall stand in the same
position under the provisions of this Agreement with respect to the resulting or
surviving corporation as Indemnitee would have with respect to such constituent
corporation if its separate existence had continued.

          (b)  For purposes of this Agreement, references to "other enterprises"
shall include employee benefit plans; references to "fines" shall include any
excise taxes assessed on Indemnitee with respect to an employee benefit plan;
and references to "serving at the request of the Company" shall include any
service as a director, officer, employee, agent or fiduciary of the Company
which imposes duties on, or involves services by, such director, officer,
employee, agent or fiduciary with respect to an employee benefit plan, its
participants or its beneficiaries; and if Indemnitee acted in good faith and in
a manner Indemnitee reasonably believed to be in the interest of the
participants and beneficiaries of an employee benefit plan, Indemnitee shall be



                                       6
<PAGE>


deemed to have acted in a manner "not opposed to the best interests of the
Company" as referred to in this Agreement.

          (c)  For purposes of this Agreement a "Change in Control" shall be
deemed to have occurred if (i) any "person" (as such term is used in Sections
13(d) and 14(d) of the Securities Exchange Act of 1934, as amended), other than
a trustee or other fiduciary holding securities under an employee benefit plan
of the Company or a corporation owned directly or indirectly by the stockholders
of the Company in substantially the same proportions as their ownership of stock
of the Company, (A) who is or becomes the beneficial owner, directly or
indirectly, of securities of the Company representing 10% or more of the
combined voting power of the Company's then outstanding Voting Securities,
increases his beneficial ownership of such securities by 5% or more over the
percentage so owned by such person, or (B) becomes the "beneficial owner" (as
defined in Rule 13d-3 under said Act), directly or indirectly, of securities of
the Company representing more than 20% of the total voting power represented by
the Company's then outstanding Voting Securities, (ii) during any period of two
consecutive years, individuals who at the beginning of such period constitute
the Board of Directors of the Company and any new director whose election by the
Board of Directors or nomination for election by the Company's stockholders was
approved by a vote of at least two-thirds of the directors then still in office
who either were directors at the beginning of the period or whose election or
nomination for election was previously so approved, cease for any reason to
constitute a majority thereof, or (iii) the stockholders of the Company approve
a merger or consolidation of the Company with any other corporation other than a
merger or consolidation which would result in the Voting Securities of the
Company outstanding immediately prior thereto continuing to represent (either by
remaining outstanding or by being converted into Voting Securities of the
surviving entity) at least 80% of the total voting power represented by the
Voting Securities of the Company or such surviving entity outstanding
immediately after such merger or consolidation, or the stockholders of the
Company approve a plan of complete liquidation of the Company or an agreement
for the sale or disposition by the Company of (in one transaction or a series of
transactions) all or substantially all of the Company's assets.

          (d)  For purposes of this Agreement, "Independent Legal Counsel" shall
mean an attorney or firm of attorneys, selected in accordance with the
provisions of Section 1(c) hereof, who shall not have otherwise performed
services for the Company or Indemnitee within the last three years (other than
with respect to matters concerning the rights of Indemnitee under this
Agreement, or of other indemnitees under similar indemnity agreements).

          (e)  For purposes of this Agreement, a "Reviewing Party" shall mean
any appropriate person or body consisting of a member or members of the
Company's Board of Directors or any other person or body appointed by the Board
of Directors who is not a party to the particular Claim for which Indemnitee are
seeking indemnification, or Independent Legal Counsel.

          (f)  For purposes of this Agreement, "Voting Securities" shall mean
any securities of the Company that vote generally in the election of directors.

          11.  Counterparts. This Agreement may be executed in one or more
counterparts, each of which shall constitute an original.



                                       7
<PAGE>


          12.  Binding Effect; Successors and Assigns. This Agreement shall be
binding upon and inure to the benefit of and be enforceable by the parties
hereto and their respective successors, assigns, including any direct or
indirect successor by purchase, merger, consolidation or otherwise to all or
substantially all of the business and/or assets of the Company, spouses, heirs,
and personal and legal representatives. The Company shall require and cause any
successor (whether direct or indirect by purchase, merger, consolidation or
otherwise) to all, substantially all, or a substantial part, of the business
and/or assets of the Company, by written agreement in form and substance
satisfactory to Indemnitee, expressly to assume and agree to perform this
Agreement in the same manner and to the same extent that the Company would be
required to perform if no such succession had taken place. This Agreement shall
continue in effect with respect to Claims relating to Indemnifiable Events
regardless of whether Indemnitee continues to serve as a director, officer,
employee, agent or fiduciary of the Company or of any other enterprise at the
Company's request.

          13.  Attorneys' Fees. In the event that any action is instituted by
Indemnitee under this Agreement or under any liability insurance policies
maintained by the Company to enforce or interpret any of the terms hereof or
thereof, Indemnitee shall be entitled to be paid all Expenses incurred by
Indemnitee with respect to such action, regardless of whether Indemnitee is
ultimately successful in such action, and shall be entitled to the advancement
of Expenses with respect to such action, unless, as a part of such action, a
court of competent jurisdiction over such action determines that each of the
material assertions made by Indemnitee as a basis for such action was not made
in good faith or was frivolous. In the event of an action instituted by or in
the name of the Company under this Agreement to enforce or interpret any of the
terms of this Agreement, Indemnitee shall be entitled to be paid all Expenses
incurred by Indemnitee in defense of such action (including costs and expenses
incurred with respect to Indemnitee counterclaims and cross-claims made in such
action), and shall be entitled to the advancement of Expenses with respect to
such action, unless, as a part of such action, a court having jurisdiction over
such action determines that each of Indemnitee material defenses to such action
was made in bad faith or was frivolous.

          14.  Notice. All notices and other communications required or
permitted hereunder shall be in writing, shall be effective when given, and
shall in any event be deemed to be given (a) five (5) days after deposit with
the U.S. Postal Service or other applicable postal service, if delivered by
first class mail, postage prepaid, (b) upon delivery, if delivered by hand, (c)
one business day after the business day of deposit with Federal Express or
similar overnight courier, freight prepaid, or (d) one day after the business
day of delivery by facsimile transmission, if delivered by facsimile
transmission, with copy by first class mail, postage prepaid, and shall be
addressed if to Indemnitee, at the Indemnitee address as set forth beneath
Indemnitee signatures to this Agreement and if to the Company at the address of
its principal corporate offices (attention: Secretary) or at such other address
as such party may designate by ten days' advance written notice to the other
party hereto.

          15.  Consent to Jurisdiction. The Company and Indemnitee each hereby
irrevocably consent to the jurisdiction of the courts of the State of New York
or (to the extent subject matter jurisdiction exists therefor) of the United
States District Court for the Southern District of New York for all purposes in
connection with any action or proceeding which arises out of or relates to this
Agreement.



                                       8
<PAGE>


          16.  Severability. The provisions of this Agreement shall be severable
in the event that any of the provisions hereof (including any provision within a
single section, paragraph or sentence) are held by a court of competent
jurisdiction to be invalid, void or otherwise unenforceable, and the remaining
provisions shall remain enforceable to the fullest extent permitted by law.
Furthermore, to the fullest extent possible, the provisions of this Agreement
(including, without limitations, each portion of this Agreement containing any
provision held to be invalid, void or otherwise unenforceable, that is not
itself invalid, void or unenforceable) shall be construed so as to give effect
to the intent manifested by the provision held invalid, illegal or
unenforceable.

          17.  Choice of Law. This Agreement shall be governed by and its
provisions construed and enforced in accordance with the laws of the State of
New York.

          18.  Subrogation. In the event of payment under this Agreement, the
Company shall be subrogated to the extent of such payment to all of the rights
of recovery of Indemnitee who shall execute all documents required and shall do
all acts that may be necessary to secure such rights and to enable the Company
effectively to bring suit to enforce such rights.

          19.  Amendment and Termination. No amendment, modification,
termination or cancellation of this Agreement shall be effective unless it is in
writing signed by both the parties hereto. No waiver of any of the provisions of
this Agreement shall be deemed or shall constitute a waiver of any other
provisions hereof (whether or not similar) nor shall such waiver constitute a
continuing waiver.

          20.  Integration and Entire Agreement. This Agreement sets forth the
entire understanding between the parties hereto and supersedes and merges all
previous written and oral negotiations, commitments, understandings and
agreements relating to the subject matter hereof between the parties hereto.

          21.  No Construction as Employment Agreement. Nothing contained in
this Agreement shall be construed as giving Indemnitee any right to be retained
in the employ of the Company or any of its subsidiaries.



                                       9
<PAGE>

          IN WITNESS WHEREOF, the parties hereto have executed this Agreement as
of the date first above written.


                                   ODSYSSEY RE HOLDINGS CORP.


                                   By: /s/ Donald L. Smith
                                       -----------------------------------------

                                       Name:     Donald L. Smith

                                       Title:    Senior Vice President, General
                                                 Counsel and Corporate Secretary

                                       Address:  140 Broadway, 39th Floor
                                                 New York, New York  10005




AGREED TO AND ACCEPTED BY:



Signature: /s/ Charles D. Troiano
           -------------------------------

Name: Charles D. Troiano
      ------------------------------------