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October 16, 2009

BY EDGAR

Julia E. Griffith

Special Counsel

Office of Mergers and Acquisitions

Securities and Exchange Commission

100 F Street, N.E.

Washington, D.C., 20549

    Re:

    Odyssey Re Holdings Corp.

Schedule TO-T and Schedule 13E-3

Filed by Fairfax Investments USA Corp. and

Fairfax Financial Holdings Limited

Filed September 23, 2009

File No. 5-61705

Dear Ms. Griffith:

On behalf of our clients, Fairfax Financial Holdings Limited (“Fairfax”) and Fairfax
Investments USA Corp. (“Purchaser” and, together with Fairfax, the “Filing
Parties”), we hereby acknowledge receipt of the comment letter dated October 14, 2009 (the
“Comment Letter”) from the staff (the “Staff”) of the Securities and Exchange
Commission (the “Commission”) concerning the above referenced Schedule TO-T and Schedule
13E-3 (the “Schedule TO”).

On behalf of the Filing Parties, we submit this letter in response to the Comment Letter. For ease
of reference, we have reproduced the text of the comments in bold-face type below, followed by the
Filing Parties’ responses. The Filing Parties are filing today, by way of EDGAR, an Amendment No.
3 to the Schedule TO-T together with this response letter. Capitalized terms
used in this letter not otherwise defined herein have the meanings ascribed to them in the Schedule
TO.

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RESPONSES TO STAFF COMMENTS

Offer to Purchase

Introduction, page 6

    1.

    Throughout your document, you refer to the board’s determination that the Offer and the
Merger are “fair to and in the best interests of Odyssey Re and the holders of Shares (other
than Fairfax and its subsidiaries).” Item 8 of Schedule 13E-3 and Item 1014 of Regulation M-A
require you to state whether the filer believes that the transaction is fair to the
unaffiliated shareholders of Odyssey. In addition to Fairfax and its subsidiaries, there
appear to be other affiliated shareholders of Odyssey Re. Please revise or advise throughout
your documents.

    Response: On behalf of the Filing Parties, we respectfully submit that the statements required
by Item 8 of Schedule 13E-3 and Item 1014 of Regulation M-A with respect to the Filing Parties’
belief that the transaction is fair to the unaffiliated shareholders of Odyssey Re are
approriately included in the Offer to Purchase. We respectfully direct the Staff’s attention to
page 2 of the Offer to Purchase, under the heading “Summary Term Sheet,” and page 14 of the
Offer to Purchase, under the heading “Special Factors—Section 4. Position of Fairfax and
Purchaser Regarding Fairness of the Offer and the Merger,” which include statements that the
Filing Parties believe that:

    •

    “[...] the transaction is fair to Odyssey Re’s stockholders who are not affiliated
with the Fairfax Group[...]”; and

    •

    “[...] the Offer Price to be received by Odyssey Re’s unaffiliated stockholders
pursuant to the Offer and the Merger is fair to such stockholders[...].”

Statements in the Offer to Purchase that the Offer and the Merger are “fair to and in the best
interests of Odyssey Re and the holders of Shares (other than Fairfax and its subsidiaries)” are
disclosures regarding resolutions of the board of directors of Odyssey Re and the special
committee thereof. Such statements are not disclosed to report the Filing Parties’ beliefs
regarding fairness.

Special Factors, page 9

    2.

    You disclose that on August 13, 2009, Fairfax launched an offering of senior notes which was
increased in size because of investor demand. As a result of the positive response to this
note offering, you state that Fairfax considered taking Odyssey Re private. Detail the events
leading up to Fairfax’s definitive decision to pursue that option, including how and when it
reached this decision and the alternatives that were considered. See Items 1013(b), (c) and
(d) of Regulation M-A. In addition, clarify why the oversubscribed note offering led Fairfax
to the going-private alternative for Odyssey Re.

    Response: We have been advised by the Filing Parties that:

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    •

    other than those events disclosed in the Offer to Purchase, there were no events
leading up to Fairfax’s definitive decision to pursue the going-private transaction;

    •

    Fairfax did not consider any alternatives to acquiring all of the outstanding shares
of common stock of Odyssey Re that the Fairfax Group did not already own.

In response to the Staff’s comment, the Filing Parties have revised the disclosure in the Offer
to Purchase, under the heading “Special Factors—Section 2. Purpose of and Reasons for the
Offer; Plans for Odyssey Re After the Offer and the Merger,” to include a statement that Fairfax
did not consider any alternatives to acquiring all of the outstanding shares of common stock of
Odyssey Re that the Fairfax Group did not already own.

As disclosed on page 9 of the Offer to Purchase, under the heading “Special Factors—Section 1.
Background,” the positive response to Fairfax’s senior notes offering was reflective of the
market’s overall assessment of Fairfax’s financial flexibility and strong financial position.
It indicated to the management of Fairfax that Fairfax would likely be able to complete an equity
offering on terms which would be satisfactory to Fairfax to fund a going-private transaction.
We are advised by the Filing Parties that these factors alone, and no others, caused Fairfax to
decide to explore the going-private transaction. In response to the Staff’s comment, the Filing
Parties have revised the disclosure in the Offer to Purchase, under the heading “Special
Factors—Section 1. Background,” to include this information.

    3.

    Expand the discussion to provide more specifics about the substance of any communications
between filing persons and their fairness advisors that are materially related to this
transaction. See Item 9 of Schedule 13E-3 and Item 1015 of Regulation M-A (these Items
encompass both oral and written “reports” prepared by financial advisors in connection with
this transactions). For example, provide more specifics about the discussions between BofA
and Fairfax on September 16-17th.

    Response: We are advised by the Filing Parties that the presentation filed as Exhibit (g) of
the Schedule TO summarizes all of the financial analyses that BofA Merrill Lynch provided orally
to management of Fairfax that are materially related to this transaction. This presentation is
summarized beginning on page 17 of the Offer to Purchase, under the heading “Special
Factors—Section 5. Presentation of BofA Merrill Lynch to Fairfax Management,” and includes the
financial analyses presented by BofA Merrill Lynch to Fairfax, and discussed between BofA
Merrill Lynch and Fairfax on September 16-17th.

    We are advised by the Filing Parties that on September 17, 2009, BofA Merrill Lynch and
management of Fairfax continued to discuss views on value and the amount that Fairfax might be
willing to pay in light of the Special Committee’s continued justification of a $66.00 per Share
offer price. In response to the Staff’s comment, the Filing Parties have revised the disclosure
in the Offer to Purchase, under the heading “Special Factors—Section 1. Background,” to
include this information.

    4.

    See our last comment above. We remind you that each presentation, discussion or report held
with or presented by an outside party that is materially related to the Rule 13e-3
transaction, whether oral or written, is a separate report that requires a

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    reasonably detailed description meeting the requirements of Item 1015 of Regulation M-A. This
requirement applies to both preliminary and final reports. Please confirm that you have
summarized all presentations or reports, both oral and written, provided by any outside party to
Fairfax, including any such reports received before August 2009, that are materially related to
an acquisition of Odyssey. This may include analyses or reports generated in contemplation of a
different transaction structure than the tender offer. In this regard, please confirm that you
have summarized all written presentations by BofA Merrill Lynch, beginning with your first
contemplation of any going private transaction. File any written materials, including board
books, as exhibits to Item 9 of Schedule 13E-3 and pursuant to Item 1016(c) of Regulation M-A,
or advise us as to why the reports are not material to the transaction.

    Response: On behalf of the Filing Parties, we confirm that:

    •

    the Offer to Purchase summarizes all presentations, discussions and reports, both
oral and written, held with or presented by any outside party, including any such
reports received before August 2009, that are materially related to the going-private
transaction;

    •

    subject to our response to Staff comment No. 12 below, the Offer to Purchase
summarizes all written presentations by BofA Merrill Lynch, beginning with the first
contemplation of any going-private transaction; and

    •

    all written materials, including board books, have been filed as exhibits to the
Schedule TO.

    5.

    All non-public information, including projections and forecasts, shared between Odyssey Re
and Fairfax, or by either party with BofA Merrill Lynch or Sandler O’Neill in connection with
this transaction, should be summarized in the offer materials. Any such information should be
accompanied by a discussion of the material assumptions which underlie it, as well as a
discussion of any relevant limitations. Please revise or advise.

    Response: On behalf of the Filing Parties, we confirm that all material non-public information,
including projections and forecasts, shared between Odyssey Re and Fairfax, or by either party
with BofA Merrill Lynch or Sandler O’Neill in connection with this transaction, as well as all
material assumptions and limitations underlying such information, have been summarized in the
offer materials.

    6.

    Provide more specifics about how you eventually determined the $65.00 per share offer price.

    Response: In response to the Staff’s comment, the Filing Parties have revised the disclosure in
the Offer to Purchase, under the heading “Special Factors—Section 1. Background,” to include a
statement that Fairfax decided to offer $65.00 per Share, representing the midpoint between its $64.00 per Share

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    offer and the Special Committee’s $66.00 per Share counter-proposal, with the objective of
reaching an agreement with the Special Committee.

Purpose of and Reasons for the Offer, page 13

    7.

    Your statement that the purpose of the Offer is for Fairfax to obtain all outstanding Shares
seems to describe the effect of the transaction rather than its purpose. Revise to
explain why Fairfax chose to pursue this result, including why it chose to do so at this time.

    Response: In response to the Staff’s comment, the Filing Parties have revised the Offer to
Purchase, under the heading “Special Factors—Section 2. Purpose of and Reasons for the Offer;
Plans for Odyssey Re After the Offer and the Merger,” to state that the purpose of the Offer is
for Fairfax to obtain ownership of all of the common equity of Odyssey Re and, accordingly, to
participate in 100% of the earnings and growth in book value of Odyssey Re.

    As disclosed on page 13 of the Offer to Purchase, under the heading “Special Factors—Section 2.
Purpose of and Reasons for the Offer; Plans for Odyssey Re After the Offer and the Merger,”
Fairfax intends not to make any changes in Odyssey Re’s strategic or operating philosophy
following completion of the proposed Offer and Fairfax expects that Odyssey Re will continue to
operate its business on an independent and decentralized basis.

    We respectfully direct the Staff’s attention to page 13 of the Offer to Purchase, under the
heading “Special Factors—Section 2. Purpose of and Reasons for the Offer; Plans for Odyssey Re
After the Offer and the Merger,” which states the reasons why Fairfax chose to pursue this
transaction, including why it chose to do so at such time.

    8.

    See our last comment above. Expand your explanation of alternatives considered, including
why each was rejected in favor of this transaction.

    Response: On behalf of the Filing Parties, we confirm that no alternatives were considered
other than the acquisition of all of the outstanding shares of common stock of Odyssey Re that
the Fairfax Group did not already own. As described in our response to Staff comment No. 2
above, the Filing Parties have revised the disclosure in the Offer to Purchase, under the
heading “Special Factors—Section 2. Purpose of and Reasons for the Offer; Plans for Odyssey Re
After the Offer and the Merger,” to include this information.

Position of Fairfax and Purchaser Regarding Fairness of the Offer and the Merger, page 14

    9.

    We note your statement at the bottom of page 16 that Fairfax and Purchaser did not consider
the liquidation value of Odyssey Re and why. However, if liquidation value would yield a
higher per share value than the offer price, please disclose.

    Response: On behalf of the Filing Parties, we confirm that the Filing Parties’ belief is that
the liquidation value would not yield a higher per share value than the Offer Price.

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    10.

    Explain why Fairfax and Purchaser did not consider the going concern value of Odyssey Re in
assessing the fairness of the transaction. If going concern value would yield a higher per
share value than the offer price, please disclose.

    Response: We respectfully direct the Staff’s attention to page 15 of the Offer to Purchase,
under the heading “Special Factors—Section 4. Position of Fairfax and Purchaser Regarding
Fairness of the Offer and the Merger,” in the Offer to Purchase, which states that the Filing
Parties considered the going concern value of Odyssey Re and believed that the going concern
value of Odyssey Re as a public company could be less than the Offer Price of $65.00 per Share
due to the negative impact of the following factors on Odyssey Re: general market conditions,
the increasingly competitive reinsurance environment, required financial flexibility and the
growing capital bases of Odyssey Re’s primary competitors.

    11.

    See the last two comments above. Provide the same disclosure with respect to the book value
per share. See Instruction 2 to Item 1015 of Regulation M-A.

    Response: On behalf of the Filing Parties, we confirm that based on book value per share as of
June 30, 2009 and estimated book value per share as of September 30, 2009 (in each case as
disclosed in the Offer to Purchase under the headings “The Offer—Section 7. Certain
Information Concerning Odyssey Re—Financial Information” and “Special Factors—Section 5.
Presentation of BofA Merrill Lynch to Fairfax Management”), book value per share is less than
the Offer Price. Analysis regarding book value per share was included in BofA Merrill Lynch’s
analyses presented to the management of Fairfax as described in the Offer to Purchase, beginning
on page 17 under the heading “Special Factors—Section 5. Presentation of BofA Merrill Lynch to
Fairfax Management.” The analyses contained in the BofA Merrill Lynch pres