Document:

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                                                                   Exhibit 10.10

                              ALLEGHANY CORPORATION

                     NON-EMPLOYEE DIRECTORS' RETIREMENT PLAN

1.   Purpose of the Plan.

     This plan, known as the Alleghany Corporation Non-Employee Directors'
Retirement Plan (the "Plan"), is maintained by Alleghany Corporation, a Delaware
corporation ("Alleghany"), for the purpose of providing additional compensation
in the form of retirement benefits for members of its board of directors (the
"Board") who were not employees of Alleghany or any of its subsidiaries and who
served as members of the Board prior to January 1, 2005.

2.   Participants.

     Every person who served as a non-employee director of Alleghany at any time
after the Effective Date and prior to January 1, 2005, shall be a participant (a
"Participant") under the Plan.

3.   Vesting.

     In order to be entitled to a benefit under the Plan, a Participant must:

          (a) have at least five years of Credited Service; and

          (b) have ceased to serve as a director of Alleghany either (i) at the
     time required by Alleghany's retirement policy for directors as then in
     effect or (ii) upon or after attaining age 70.

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Credited Service shall mean all years and fractions of a year, whether before or
after the Effective Date, during which the Participant served as a director of
Alleghany or of Alleghany Corporation, a Maryland corporation, while not an
employee of either such corporation or any of their subsidiaries; provided that
no period of service as a director after December 31, 2004, shall be recognized
as Credited Service for purposes of measuring the duration of a Participant's
benefit under the Plan.

4.   Benefit.

     The benefit payable to a Participant who is entitled to a benefit under the
Plan shall be an annual amount equal to (a) the basic annual retainer payable to
non-employee directors of Alleghany at the time such Participant ceased to be a
director of Alleghany, exclusive of additional fees and expenses paid for
attendance at or participation in meetings of the Board of Directors and service
on committees of the Board, and exclusive of benefits under the Alleghany
Corporation Directors' Stock Option Plan or the like, or (b), in the case of a
Participant who ceases to be a director of Alleghany after December 31, 2004,
the basic annual retainer for 2004 of $30,000.

5.   Duration of Benefit.

     A Participant who is entitled to receive a benefit under the Plan shall
receive such benefit commencing upon the termination for any reason of his
service as a director of Alleghany and continuing until the end of a period
equal to his Credited Service, or until his death, whichever occurs sooner.

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6.   Payment or Benefit.

     One-fourth of the annual benefit payable to a Participant hereunder shall
be paid at the end of each calendar quarter, beginning with the calendar quarter
following that in which his service as a director of Alleghany terminated. If
the Credited Service of a Participant includes a fraction of a calendar quarter,
his final payment shall consist of the same fraction of the amount otherwise
payable per calendar quarter. In the event of a Participant's death prior to
termination of his benefit payments, the final such payment shall be made at the
end of the calendar quarter in which his death has occurred.

7.   General Provisions.

          (a) Nothing in the Plan shall create, or be construed to create, a
     trust or fiduciary relationship of any kind between Alleghany and a
     Participant or any other person. All amounts payable under the Plan shall
     be paid from the general funds of Alleghany, and the right to receive
     payments from Alleghany under the Plan shall be no greater than the right
     of any unsecured general creditor. Alleghany may, but need not, purchase
     securities or instruments as a means of hedging its obligations to any
     participant under the Plan, but if it does, neither the Participant nor any
     other person shall have any interest therein or other right to any such
     property. All payments hereunder shall be made in cash.

          (b) The right of any Participant to receive benefits under the Plan
     shall not be assigned, transferred, pledged or encumbered in my manner, nor
     shall it be subject to

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     attachment or to interference or control, by the creditors or beneficiaries
     of any Participant.

          (c) Participation in the Plan shall not be construed as conferring
     upon any Participant the right to continue as a director of Alleghany or in
     any other capacity.

8.   Administration of the Plan.

     The Plan shall be administered by an officer or Alleghany (the "Plan
Administrator'") appointed by the Board to serve as administrator under the
direction of the Board. The Board shall have full power and authority at my time
to interpret, construe, administer, amend and terminate the Plan, and the
Board's interpretation and construction thereof and actions taken thereunder
shall be binding on all persons for all purposes; provided, that no amendment or
termination of the Plan shall reduce the benefits to which any Participant has
previously become entitled under the Plan.

9.   Governing Law.

     The Plan shall be governed by and construed under the laws of the State of
New York.

10.  Effective Date.

     The effective date of the Plan (the "Effective Date") is July 1, 1990.

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                                                                Exhibit 10.11(d)

                              ALLEGHANY CORPORATION

                        Restricted Stock Award Agreement

          Restricted Stock Award Agreement (this "Agreement"), dated as of
December 31, 2004, between Alleghany Corporation, a Delaware corporation
("Alleghany"), and Weston M. Hicks (the "Participant").

          Section 1. Restricted Stock Award.  Alleghany hereby grants to the
Participant, on the terms and conditions hereinafter set forth, a restricted
stock award of 26,010 shares of the common stock, par value $1.00 per share (the
"Common Stock") of Alleghany (the "Restricted Shares"). This grant has been made
by the Compensation Committee of the Board of Directors of Alleghany (the
"Committee") pursuant to the terms of the Alleghany Corporation 2002 Long-Term
Incentive Plan (the "Plan") and is intended to qualify as "performance-based
compensation" for purposes of Section 162(m) of the Internal Revenue Code of
1986, as amended. The applicable terms of the Plan are incorporated herein by
reference. Any terms used but not defined herein shall have the meanings
ascribed thereto in the Plan. Any ambiguity between any term used in this
Agreement and a term used in the Plan shall be resolved in favor of and in
accordance with the term used in the Plan. Any interpretation, determination or
decision made or taken by the Committee regarding the Plan or this Agreement
shall be final and binding upon Alleghany and the Participant.

          Section 2. Vesting of Restricted Shares.  Subject to Section 3 hereof,
the Restricted Shares shall vest and become nonforfeitable as follows:

          (a)  If Alleghany achieves average annual compound growth in
               Stockholders' Equity Per Share equal to 10% or more as measured
               over a calendar year period commencing January 1, 2005 and ending
               on December 31, 2008, 2009, 2010 or 2011, the Restricted Shares
               will vest and become nonforfeitable upon the certification by the
               Committee that such performance goal has been met.

          (b)  If the performance goal set forth in (a) above has not been
               achieved as of December 31, 2011, the Restricted Shares will vest
               and become nonforfeitable when Alleghany achieves average annual
               compound growth in Stockholders' Equity Per Share equal to 7% or
               more as measured over a calendar year period commencing January
               1, 2005 and ending on December 31, 2012, 2013 or 2014 and upon
               the certification by the Committee that such performance goal has
               been met.

          (c)  If the performance goals provided above are not achieved as of
               December 31, 2014, the Participant will forfeit all of the
               Restricted Shares.

          (d)  "Stockholders' Equity Per Share" shall mean the stockholders'
               equity per share of Common Stock of Alleghany, determined, except
               as otherwise herein provided, on the basis of the same accounting

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               principles used in the preparation of Alleghany's consolidated
               balance sheet for the calendar year in question which is included
               in Alleghany's Annual Report to Stockholders for such calendar
               year. Stockholders' Equity Per Share shall be determined and
               certified in writing by the Committee, with such adjustments as
               the Committee shall deem to be required to take account of the
               effects on Stockholders' Equity Per Share of any stock dividend,
               unusual cash distributions, spin-off, stock split,
               recapitalization, merger, consolidation or other similar event
               and will also be automatically adjusted to reflect reinvestment
               of the value of dividends and distributions other than stock
               dividends. The Committee's determination with respect to any such
               adjustments shall be final and binding.

          Section 3. Custody and Delivery of Shares.  Alleghany shall hold the
certificate or certificates representing the Restricted Shares subject to this
Award until such Restricted Shares have vested pursuant to Section 2 hereof.
Contemporaneous with the execution of this Agreement, the Participant shall
execute and deliver to Alleghany one or more irrevocable stock powers related
thereto to facilitate the transfer of the Restricted Shares subject to this
Award to Alleghany (or its assignee or nominee) if such Restricted Shares are
forfeited pursuant hereto. Upon the vesting of the Restricted Shares subject to
this Award pursuant to Section 2 hereof, Alleghany shall deliver or cause to be
delivered the certificate or certificates representing such Restricted Shares to
the Participant, shall destroy the related stock power or powers, and shall pay
all original issue or transfer taxes and all fees and expenses incident to such
delivery.

          Section 4. Termination of Employment.  If the Participant's employment
with Alleghany is terminated for any reason prior to the occurrence of any
otherwise applicable vesting date provided in Section 2 hereof, the Participant
shall (i) forfeit his interest in any Restricted Shares that have not yet become
vested, (ii) assign, transfer, and deliver any certificates evidencing ownership
of such Restricted Shares to Alleghany, and (iii) cease for all purposes to be a
stockholder with respect to such Restricted Shares; provided, however, that if,
subsequent to December 31, 2006, Alleghany terminates the Participant's
employment other than for Cause or other than in the case of Total Disability,
and, as of the calendar year end immediately preceding such termination, the
performance goal set forth in Section 2(b) has been satisfied in all respects
except for the passage of the required period of time, the following number of
Restricted Shares shall vest and become nonforfeitable upon written
certification by the Committee that such pro rated performance goal has been
achieved: 26,010 multiplied by a fraction the numerator of which is the number
of full calendar years beginning January 1, 2005 and ending on or before the
date of such termination, and the denominator of which is ten. For purposes
hereof, "Cause" shall mean conviction of a felony; willful failure to implement
reasonable directives of the President, Chairman or the Board of Directors of
Alleghany after written notice, which failure is not corrected within ten days
following notice thereof; or gross misconduct in connection with the performance
of any of Participant's duties; and "Total Disability" shall mean Participant's
inability to discharge his duties due to physical or

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mental illness or accident for one or more periods totaling six months during
any consecutive twelve-month period.

          Section 5. Rights as a Stockholder.  Subject to the otherwise
applicable provisions of the Plan and this Agreement, the Participant will have
all rights of a stockholder of the shares of Common Stock in respect of which
the Restricted Shares are granted to the Participant hereunder, including the
right to vote the shares and receive all dividends and other distributions paid
in respect thereof; provided, however, that Alleghany shall retain all cash
dividends or other cash distributions on the Restricted Shares until they vest,
using such cash to purchase shares of Common Stock at the Fair Market Value
thereof on the date paid, and the Participant shall deliver any stock dividends
or other non-cash distributions on the Restricted Shares until they vest
(including, without limitation, shares of any corporation distributed in a
spin-off), together with appropriate stock transfer or other assignment
documents, to Alleghany. The Common Stock acquired with the cash dividends or
other cash distributions on the Restricted Shares or distributed as a stock
dividend and any other non-cash distributions on the Restricted Shares (the
"Distribution Amounts") shall be held by Alleghany until the Restricted Shares
in respect of which such Distribution Amounts were paid vest and become
nonforfeitable, at which time such Distribution Amounts shall also vest and
become nonforfeitable, and the certificates or other evidence of the
Distribution Amounts shall be delivered, or caused to be delivered, by
Alleghany. Alleghany shall also destroy the related stock power or powers, and
shall pay all original issue or transfer taxes and all fees and expenses
incident to such delivery. To the extent that any Restricted Shares are
forfeited pursuant to the terms of this Agreement, the Distribution Amounts paid
in respect thereof shall also be forfeited.

          Section 6. Restrictions on Transfer.  Neither this Agreement nor any
Restricted Shares covered hereby or dividends or other distributions paid in
respect thereof may be sold, assigned, transferred, encumbered, hypothecated or
pledged by the Participant, other than to Alleghany as a result of forfeiture of
the Restricted Shares and dividends or other distributions as provided herein,
or unless such Restricted Shares and dividends or other distributions have
vested and become nonforfeitable in accordance herewith. Any such disposition by
the Participant shall be made in compliance with all applicable securities laws.
The Participant hereby represents and warrants to Alleghany that the Restricted
Shares are being acquired for investment and not with a view to the distribution
thereof, and not with any present intention of distributing the same.

          Section 7. Tax Withholding.  Alleghany's obligation to deliver the
Restricted Shares to the Participant pursuant to Section 3 hereof and any
Distribution Amount is subject to the Participant's making provision for the
payment or withholding of any taxes required to be paid or withheld pursuant to
any applicable law in respect of the receipt of, or lapse of forfeiture
restrictions with respect to, such Restricted Shares and the payment or delivery
of any Distribution Amounts. At the written election of Participant, and upon
the approval of the Committee, any such required withholding payments may be
made in Restricted Shares or Distribution Amounts, in each case valued at Fair
Market Value on the date of payment.

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          Section 8. No Right of Employment.  Nothing in this Agreement shall
confer upon the Participant any right to continue as an employee of Alleghany or
to interfere in any way with the right of Alleghany to terminate the
Participant's employment at any time.

          Section 9. Entire Agreement.  This Agreement, the letter agreement
dated as of October 7, 2002, the Restricted Stock Award Agreement dated as of
October 7, 2002, and the Restricted Stock Unit Matching Grant Agreement dated as
of October 7, 2002 contain the entire understanding of Alleghany and the
Participant with respect to the subject matter hereof and thereof and, except as
specifically provided herein or therein, cancel and supersede any and all other
agreements between Alleghany and the Participant with respect to the subject
matter hereof and thereof. Any amendment or modification of this Agreement shall
not be binding unless in writing and signed by Alleghany and the Participant.

          Section 10. Governing Law.  This Agreement shall be governed by and
enforceable in accordance with the laws of the State of New York, without giving
effect to the principles of conflict of laws thereof.

          IN WITNESS WHEREOF, the Participant has duly executed this Agreement
and Alleghany has duly caused this Agreement to be executed in its name and on
its behalf, all as of December 31, 2004.

                                      ALLEGHANY CORPORATION

                                      By: /s/ Dan R. Carmichael
                                          --------------------------------------
                                          Dan R. Carmichael
                                          Chairman of the Compensation Committee

                                      PARTICIPANT

                                          /s/ Weston M. Hicks
                                          --------------------------------------
                                          Weston M. Hicks

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