<PAGE>
                                                                   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.

<PAGE>

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.


                                      -2-

<PAGE>

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


                                      -3-

<PAGE>

     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.


                                      -4-