Document:

EX-10.1

 

Exhibit 10.1

ALLEGHANY CORPORATION RETIREMENT PLAN

(As Amended Through April 17, 2007)

     This document sets forth the Alleghany Corporation Retirement Plan, as amended and restated
effective as of December 31, 2006 and as thereafter amended to comply with the requirements of
Section 409A of the Code.

     The Plan, as so amended and restated, is intended to be a plan which is unfunded and is
maintained by Alleghany Corporation primarily for the purpose of providing deferred compensation
for a select group of management or highly compensated employees both within the meaning, and for
the purposes, of Sections 201(2), 301(a)(3) and 401(a)(1) of the Employee Retirement Income
Security Act of 1974, as amended.

     The rights under the Plan of any person who retired or otherwise terminated employment with
Alleghany Corporation before the effective date of a particular amendment shall be determined
solely under the terms of the Plan as in effect on the date of such retirement or other termination
of employment, without regard to such amendment, except that such person’s benefit under the Plan
may be paid at such time, and in such form, as may be permitted under the terms of the Plan as in
effect on the date as of which the payment of such person’s benefit commences.

ARTICLE I.

DEFINITIONS

     1.01 “Actuarial Equivalent” means with respect to a retirement benefit, an equivalent
amount or amounts computed using (i) the mortality table prescribed in Section 417(e)(3)(A)(ii)(I)
of the Code and (ii) the interest rate prescribed by the Internal Revenue Service under Section
417(e)(3)(A)(ii)(II) of the Code for the month immediately preceding the month in which such
Actuarial Equivalent is being determined.

     For purpose of this Section 1.01, all references to Section 417(e)(3) of the Code shall be
administered without regard to the effects enacted under the Pension Protection Act of 2006. In
addition, at such time as the Internal Revenue Service ceases to publish the relevant interest
rate, the determination of an Actuarial Equivalent shall instead be computed using the U.S. 30-year
Treasury rate in effect at the close of the first business day of the month in which such Actuarial
Equivalent is being determined.

     1.02 “Alleghany” means Alleghany Corporation and, solely for purposes of determining
the date of a Participant’s Termination of Employment (other than by reason of his ceasing to be an
officer), includes any corporation or other person treated as a single employer with Alleghany
Corporation under Section 414(b) or (c) of the Code.

     1.03 “Annuity Starting Date” means the first day on which an amount is payable to the
Participant in accordance with this Plan.

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     1.04 “Average Compensation” means, with respect to any Participant, the annual average
of his Base Compensation and his Short-Term Incentive Compensation for the three consecutive
calendar years in the period of ten calendar years ending with the calendar year in which he has a
Termination of Employment, which results in the highest such average.

     1.05 “Base Compensation” means the base salary earned by an Employee for the relevant
period (whether or not such compensation is currently payable or deferred) for his services as
such, which base salary shall not include (by way of illustration and not limitation) any non cash
compensation, any savings benefit amounts, (any Short-Term Incentive Compensation), long term
incentive bonuses, restricted stock or other extraordinary compensation, payments, allowances or
reimbursements.

     In the case of a Participant who becomes Totally Disabled, the Participant shall be treated as
earning Base Compensation, for the period which begins on the date on which he becomes Totally
Disabled and which ends on his Normal Retirement Date, at an annual rate which is equal to his
annual rate of base salary immediately prior to the date on which he becomes Totally Disabled.
Such amount shall be adjusted on the first day of each Plan Year included in such period to take
into account the percentage increase, if any, in the CPIU over the previous Plan Year. The “CPIU”
is the U.S. City Average All Items Consumer Price Index for all Urban Consumers, published by the
U.S. Department of Labor, Bureau of Labor Statistics, or any successor index designated by the
Department of Labor.

     1.06 “Beneficiary” means the person or persons last designated by a Participant, on a
form provided by, and filed with, the Plan Administrator, to receive benefits under Article V
following the Participant’s death. If all the persons so designated are individuals and if there
is no such individual living at the death of the Participant, or if no such person has been
designated, then the Participant’s Beneficiary shall be his estate, and if such Participant and his
Beneficiaries all die before all the specified monthly payments have been made under a period
certain option elected by the Participant, the commuted value of the balance shall be paid in a
lump sum to the estate of the last to survive of the Participant and his Beneficiaries.

     1.07 “Board” means the Board of Directors of Alleghany or the Executive Committee
thereof.

     1.08 “Code” means the Internal Revenue Code of 1986, as amended.

     1.09 “Early Retirement Date” means, with respect to any Participant, the first day of
the calendar month coinciding with or next following the latest of (a) the date on which he incurs
a Termination of Employment, (b) the date on which he attains age 55, (c) the date (not later than
his Normal Retirement Date) elected by him (where such election is made in accordance with Section
5.07), or (d) completion of 5 years of service.

     1.10 “Employee” means any individual in the employ of Alleghany. No person who is
engaged by, or performs services for, Alleghany pursuant to any agreement or arrangement
designating such engagement or services as that of a “consultant,” “independent contractor” or

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other words of similar meaning shall be deemed an Employee.

     1.11 “Employment Commencement Date” means the first day on which an Employee is
employed as a common-law employee by Alleghany.

     1.12 “ERISA” means the Employee Retirement Income Security Act of 1974 and the
regulations thereunder, as from time to time amended and in effect.

     1.13 “Late Retirement Date” means the first day of the calendar month coinciding with
or next following the date on which a Participant incurs a Termination of Employment after his
Normal Retirement Date.

     1.14 “Normal Retirement Date” means the first day of the calendar month coinciding
with or next following the first date on which a Participant has attained at least age 65 and has
completed at least 5 Years of Service.

     1.15 “Participant” means an Employee who has been selected to participate in the Plan
as provided in Article II or who has any accrued retirement benefits under the Plan which have not
been distributed in full to him (or his Beneficiary).

     1.16 “Plan” means the plan set forth herein as modified or amended from time to time.

     1.17 “Plan Administrator” means the person serving from time to time as the Treasurer
of Alleghany, or if no person is so serving at the time of reference, then Alleghany.

     1.18 “Plan Year” means a calendar year.

     1.19 “Short-Term Incentive Compensation” means the amount of the cash bonus accrued by
an Employee in respect of the relevant period (whether or not such amount is currently paid or
deferred) under the Alleghany Management Incentive Plan (or any plan adopted by the Board in
replacement of such plan).

     In the case of a Participant who becomes Totally Disabled, the Participant shall be treated as
accruing Short-Term Incentive Compensation for the period which begins on the date on which he
becomes Totally Disabled and which ends on his Normal Retirement Date (the “Disability Period”), at
an annual rate which is equal to his average annual rate of Short-Term Incentive Compensation. For
this purpose, a Participant’s average annual rate of Short-Term Incentive Compensation shall mean
the average of his Short-Term Incentive Compensation for the three consecutive calendar years in
the period of the ten calendar years which immediately precedes the date he becomes Totally
Disabled and which results in the highest such average, or if he had not been employed by the
Alleghany for at least 3 complete, consecutive calendar years, then the annual average of his
Short-Term Incentive Compensation for all full calendar years during which he was so employed.
Such average annual rate of Short-Term Incentive Compensation shall be adjusted, for each calendar
year in the Disability Period, to take into account the percentage increase, if any, in the CPIU
(as defined in Section 1.04) over the

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previous calendar year.

     1.20 “Spouse” shall mean the person to whom the Participant is lawfully married under
applicable law at the time of reference.

     1.21 “Termination of Employment” means, and an Employee shall be treated as having
incurred, a termination of employment as of the first date on which he ceases for any reason to be
an officer of Alleghany, as provided in the By Laws of Alleghany. A Participant who becomes
Totally Disabled shall not be treated as having incurred a Termination of Employment for any
purpose of the Plan until the earliest of the date on which he ceases to be Totally Disabled
(assuming he does not resume his employment with Alleghany on such date), his Normal Retirement
Date or the date of his death. Solely for purposes of determining the date of the commencement of
any Participant’s benefits, the date of a Participant’s Termination of Employment shall not be
earlier than the date of the Participant’s “termination of employment” within the meaning of
Treasury Regulation Section 1.409A-1(h)(1).

     1.22 “Totally Disabled” means a physical and/or mental incapacity of such condition
that it qualifies an individual (after the waiting period required thereunder) for benefits under
the Alleghany Corporation Group Long Term Disability Plan, as in effect from time to time.

     1.23 “Year of Service” shall mean as to any Participant, the number of whole or
fractional periods of 12 consecutive months (such fraction being computed on the basis of complete
months) which are included in the period which begins on the date on which he first became a
Participant and which ends on the date of his final Termination of Employment (which, for the
avoidance of doubt, shall include the period while he is Totally Disabled). The Board may, by
resolution, grant additional Years of Service to a Participant for such period prior to the date he
first became a Participant as the Board shall determine, which grant shall be set forth opposite
the Participant’s name on Exhibit II attached hereto. Further, a Participant employed prior to the
effective date of the Plan, January 1, 1989, shall be credited with that additional number of Years
of Service which is set forth opposite his name on Exhibit I attached hereto.

ARTICLE II.

PARTICIPATION

     2.01 Participation. Each Employee who has been elected by the Board to the position
of an officer of Alleghany, as provided in the By Laws of Alleghany, and who is designated by the
Board to participate in the Plan shall become a Participant effective on the later of his
Employment Commencement Date or the date specified by the Board.

     2.02 Re Employment of Former Participant. If a Participant or former Participant who
incurred a Termination of Employment shall again become an Employee and he is again designated by
the Board to participate in the Plan, such Employee shall again become a Participant or resume his
active participation in the Plan, as applicable, effective on the later of the date of his
re-employment or the date specified by the Board. A Participant or former Participant who again
becomes an Employee, but is not designated by the Board to participate in

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the Plan, shall not again become (or resume being) a Participant and his Years of Service and Base
Salary and Short-Term Incentive Compensation during his subsequent period of employment shall be
disregarded in calculating his benefits under this Plan.

ARTICLE III.

VESTING AND BENEFIT ENTITLEMENT

     3.01 Vesting and Entitlement. A Participant shall have a nonforfeitable right to 100
percent of, and shall be entitled to receive, his retirement benefit as determined pursuant to
Article IV if he has completed at least 5 Years of Service.

     3.02 Termination before Vesting. A Participant who terminates his employment with
Alleghany before he has completed at least 5 Years of Service shall not be entitled to any
retirement benefit under this Plan unless he is thereafter re employed by Alleghany and completes
at least 5 Years of Service.

ARTICLE IV.

RETIREMENT BENEFITS

     4.01 Retirement Benefit at Normal Retirement Date. The annual retirement benefit of a
Participant, calculated as a monthly annuity which starts on the Participant’s Normal Retirement
Date, is payable to the Participant for his life, and after the Participant’s death continues to
the Participant’s Spouse, if any, for her life in the same monthly amount as was being received by
the Participant, shall equal the product of (i) 66.67% of the Participant’s Average Compensation,
(ii) a fraction, not greater than one, the numerator of which is the number of his whole and
fractional Years of Service and the denominator of which is 15 and (iii) an Actuarial Equivalent
factor, not greater than 1, to reflect the additional value of the Spouse’s benefit on account of
the number of years and months, if any, by which the Spouse is younger than the Participant.

     4.02 Reduction for Prior Distributions. In the case of any Participant identified on
Exhibit III who received a prior distribution of retirement benefits, the Participant’s annual
retirement benefit otherwise payable under Article IV shall be offset by the Actuarial Equivalent
of amounts shown in Exhibit III.

     4.03 Retirement Benefit at Late Retirement Date.

     If a Participant terminates employment with Alleghany after his Normal Retirement Date, then
such Participant shall be entitled to receive the greater of:

     (a) the annual retirement benefit determined in accordance with the formula in Section
4.01, reduced (if applicable) as set forth in Section 4.02, based on the Participant’s Years
of Service and Average Compensation calculated as of his Normal Retirement Date, then
increased from the Participant’s Normal Retirement Date until his Annuity Starting Date
using the rate of interest in effect at the close of the first business

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day of each such calendar year for U.S. Treasury obligations with a then maturity date
of one year; or

     (b) the annual retirement benefit determined in accordance with the formula in Section
4.01, reduced (if applicable) as set forth in Section 4.02, based on the Participant’s Years
of Service and Average Compensation calculated as of his Late Retirement Date.

     4.04 Retirement Benefit at Early Retirement Date. The annual retirement benefit
payable to a Participant whose retirement benefits commence prior to his Normal Retirement Date
shall equal the annual retirement benefit determined in accordance with the formula in Section
4.01, reduced (if applicable) as set forth in Section 4.02, further adjusted as follows:

     (a) if the Participant terminated his employment with Alleghany either (i) on or after
attaining age 55 and completing at least 20 Years of Service or (ii) on or after attaining
age 60 and completing at least 10 Years of Service, then his annual retirement benefit shall
be reduced by 3% for each year (interpolated for fractional years) by which his Annuity
Starting Date is prior to the date he would attain his Normal Retirement Date; and

     (b) in all other cases, his annual retirement benefit shall be reduced by 6% for each
year (interpolated for fractional years) by which his Annuity Starting Date is prior to the
date he would attain his Normal Retirement Date.

ARTICLE V.

FORMS OF RETIREMENT BENEFITS

     5.01 Calculation of Amount of Benefit Payments. The actual amount of a Participant’s
retirement benefit distribution under this Article V in the form elected shall be the Actuarial
Equivalent of the annual retirement benefit payable to the Participant pursuant to Section 4.01,
4.03 or 4.04, as applicable to the Participant, including taking account of the actual age of the
Participant’s Spouse, if any.

     5.02 Automatic Form of Benefit.

     (a) Unless he shall elect to the contrary, a Participant who is married on his Annuity
Starting Date shall receive a retirement benefit for his life payable monthly beginning on
his Annuity Starting Date, with such monthly annuity continued to the Participant’s Spouse
(if she has survived him) for the remainder of her life in the same monthly amount as the
Participant was receiving prior to his death. For purposes of this Plan, an individual will
not be treated as the Participant’s Spouse unless she was lawfully married to the
Participant on his Annuity Starting Date (or, in the case of a Participant’s death prior to
his Annuity Starting Date, on his date of death).

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     (b) Unless he shall elect to the contrary, a Participant who is not married on his
Annuity Starting Date shall receive his retirement benefits as monthly payments which shall
continue for as long as the Participant lives after payments begin.

     5.03 Optional Forms. In lieu of the form of benefit provided for by Section 5.02, a
Participant may elect to receive his retirement benefits in any of the following optional forms:

     (a) a single life option, under which the Participant’s retirement benefit shall
consist of monthly payments which shall continue for as long as the Participant lives after
payments begin;

     (b) a period certain option, under which the Participant shall receive a retirement
benefit payable in equal monthly installments during his lifetime and ending with the
payment due on the first day of the month in which the Participant’s death occurs, but with
the provision that not less than 120 monthly installments shall be made to him and his
Beneficiaries;

     (c) a joint and survivor option, under which a Participant shall receive a monthly
retirement benefit for his life with a survivor annuity for the life of his Beneficiary
which is equal to 50% or 100%, as he shall have elected, of the monthly benefit for the
Participant’s life; or

     (d) a lump sum option, under which the Participant shall receive a single lump sum
payment equal to the retirement benefit to which he is then entitled.

     5.04 Death Benefit for Spouse.

     (a) If a Participant has completed at least 5 Years of Service, dies before his Annuity
Starting Date and is survived by a Spouse (a “Surviving Spouse”), then his Surviving Spouse
shall receive an annuity for the life of the Surviving Spouse which shall be the same as the
amount of the benefit that would have been paid to such Surviving Spouse under Section
5.02(a) if (i) in the case of a Participant who dies after attaining age 55, the Participant
had retired on the day before his death; or (ii) in the case of a Participant who dies on or
before attaining age 55, the Participant had separated from service on the date of his
death, survived until age 55, and retired at that time.

     (b) In the case of a Participant who dies after attaining age 55, such benefit to the
Surviving Spouse shall commence as of the first day of the month coinciding with or next
following the date of the Participant’s death, or, in the case of a Participant who dies on
or before attaining age 55, such benefit to the Surviving Spouse shall commence on the first
day of the month coinciding with or next following the date the Participant would have
attained age 55.

     5.05 Commencement of Benefits; Payments to Specified Employees.

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     (a) Payment of a Participant’s retirement benefit to the Participant shall be made or
commence on (and in no event shall be paid or commence later than thirty (30) days after)
the first day of the calendar month coinciding with or next following the date elected by
the Participant or at such other time as provided in the Plan, but in no event may the date
for payment or commencement of any Participant’s retirement benefits under the Plan precede
the later of the date of the Participant’s Termination of Employment or his Early Retirement
Date.

     (b) In the absence of a Participant’s effective election, payment of a Participant’s
retirement benefit shall be made in the form provided under Section 5.02, and payment of
such retirement benefit shall commence on the later of (x) the first day of the calendar
month coinciding with or next following the date the Participant has a Termination of
Employment or (y) the date the Participant attains his Normal Retirement Date.

     (c) Notwithstanding any other provision of the Plan to the contrary, if on the date of
a Participant’s Termination of Employment the Participant was a “specified employee” within
the meaning of Treasury Regulation Section 1.409A-1(i) then (i) payment of the Participant’s
retirement benefits under this Plan shall not commence before the first day of the month
that is more than six months after his Termination of Employment, and (ii) the aggregate
amount of any retirement benefit payments that would have been made to the Participant
because of his Termination of Employment in the absence of clause (i) shall be paid to the
Participant in a lump sum on the date the payment of his retirement benefits commences under
clause (i) with interest on each such retirement benefit payment deferred from the date the
payment was otherwise due until it is actually paid at the interest rate used to determine
Actuarial Equivalences on the date such payment is actually made. The “identification date”
for determining whether an Employee is a “specified employee” within the meaning of Treasury
Regulation Section 1.409A-1(i) shall be December 31st of each year.

     5.07 Time of Elections.

     (a) At any time within 30 days after an Employee is first designated as a Participant,
the Participant may affirmatively elect (an “Election”): (i) the form in which the
Participant’s retirement benefit shall be paid, and (ii) the date or dates and/or event or
events for payment of his retirement benefit under the Plan (each such date or dates and/or
event or events being referred to herein as a “Payment Date”); provided, however, that no
Election shall be given effect (and such Election shall be deemed void) if the Payment Date
is, or results in, an Annuity Starting Date that is earlier than the date of the
Participant’s Termination of Employment. Each Payment Date must be objectively
determinable, and while an Employee may amended or revise the Employee’s Election at any
time within the 30 day period after an Employee is first designated as a Participant, such
Election in effect on the close of business on such 30th day shall be irrevocable
(except as specifically provided herein). If within 30 days after an Employee is first

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designated as a Participant, the Participant has not made an effective Election, then for
purposes of the Plan, payment of a Participant’s retirement benefit shall be made in the
form provided under Section 5.02, and payment of such retirement benefit shall commence on
the later of (x) the first day of the calendar month coinciding with or next following the
date the Participant has a Termination of Employment or (y) the date the Participant attains
his Normal Retirement Date.

     (b) At least twelve months prior to the date any amount would have been paid to the
Participant on a specified Payment Date (the actual date of payment pursuant to Section
5.07(a) hereof or, in the absence of such an election, the date such amount would have been
payable pursuant to Section 5.05(b) hereof being the “Original Payment Date”), a Participant
may elect (an “Amended Election”) to defer distribution of the amount payable on, or
beginning as of, that Original Payment Date to a date after that Original Payment Date or to
change the form in which the Participant’s retirement benefit shall be paid (any such later
date shall then becomes the Payment Date); provided, however, that (a) such Amended Election
will not take effect for (and so shall be null and void until) at least 12 months after the
date on which it is made, and (b) the distribution of the amount to which the Amended
Election applies cannot be made until at least 5 years from that Original Payment Date.
Except as set forth herein, a Participant’s Amended Election may otherwise provide for
distribution at any time or in any form as could have been elected in an original Election.
There shall be no limit on the number of Amended Elections that a Participant may make.

     (c) Each election shall be in writing on a form provided by and filed with the Plan
Administrator, and shall specify the form of benefit the Participant elects and the Payment
Date or Dates of the payment of such retirement benefit. Any election, once made, shall be
irrevocable, except as provided in Section 5.07(b).

     5.08 Special 409A Provisions.

     (a) The Plan is intended to be operated in compliance with Section 409A of the Code.
If any provision of the Plan is subject to more than one interpretation, then the Plan shall
be interpreted in a manner that is consistent with Section 409A of the Code.

     (b) Unless a Participant elects otherwise, entitlement to any benefit payable as an
annuity will be treated as a single payment, made on the first day on which a payment is to
be made under the annuity, for purposes of applying Section 5.07(b) hereof with respect to
Amended Elections. In addition, actuarial equivalent forms of annuitites shall be

     (e) Notwithstanding any other provision of this Section 5.07 to the contrary, each
Participant in this Plan as of December 31, 2007, may on or before December 31, 2007, make,
modify or revoke any election as to the time or form of payment of all or any of his
retirement benefit permitted to be made under this Plan, and all such elections in effect at
the close of business on December 31, 2007, shall be irrevocable, except as

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otherwise provided herein.

     5.08 Termination of Benefit. If the period of any retirement benefit is measured by
the life of an individual, the last payment to such individual shall be the last payment due on, or
immediately prior to, the date of the individual’s death. No benefit shall be payable under the
Plan with respect to any Participant after such Participant’s death unless specifically provided
for in the Plan.

     5.09 Withholding. Alleghany shall have the right to deduct from all payments made
hereunder any federal, state, local or foreign income or employment taxes required, in the sole
judgment of Alleghany, to be withheld with respect to such payments. Notwithstanding any provision
of this Plan to the contrary, each Participant, as a condition to the entitlement to any retirement
benefits accruing under this Plan shall pay, or have made arrangements satisfactory to Alleghany
for the payment of, any employment taxes on retirement benefits accruing under this Plan.

     5.06 Automatic Payments. Notwithstanding any Participant’s election pursuant to this
Plan as to the time or form of his benefits, the following shall apply:

     (a) If any monthly payment that would otherwise be made to any person under the Plan is
less than $1,000, then, if the Plan Administrator shall so direct, the aggregate of the
amounts which shall be paid to such person in any year shall be paid in quarterly,
semiannual or annual installments; and

     (b) If the Actuarial Equivalent value of the Participant’s nonforfeitable retirement
benefit as of the date of his Termination of Employment or the retirement benefit payable to
the Participant’s Surviving Spouse as of the date of the Participant’s death, in either
case, does not exceed $100,000 if paid as a lump sum, then an amount equal to such Actuarial
Equivalent value of such retirement benefits shall be paid to the Participant or the
Participant’s Spouse in a lump sum in lieu of any retirement benefits to which he or she may
be entitled to under this Plan.

ARTICLE VI.

PLAN ADMINISTRATION

     6.01 Plan Administrator Records. The Plan Administrator shall keep or cause to be
kept all data, records and documents relating to the administration of the Plan.

     6.02 Employment of Experts. The Plan Administrator may employ or engage such
independent actuaries, accountants, counsel, and other experts or persons as the Plan Administrator
may deem necessary in connection with discharging its duties under the Plan.

     6.03 Payment of Expenses. All expenses incurred in connection with the

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administration of the Plan, including, but not limited to, the compensation of any actuary,
accountant, counsel, and other experts or persons who shall be employed by the Plan Administrator
in connection with the administration of the Plan shall be paid by Alleghany.

     6.04 Indemnification of Plan Administrator. Alleghany shall indemnify and hold
harmless to the fullest extent permitted by law the Plan Administrator and any Employee of
Alleghany to whom Plan responsibilities are delegated by the Plan Administrator from and against
any liabilities, damages, costs and expenses (including attorneys’ fees and amounts paid in
settlement of any claims approved by Alleghany) incurred by or asserted against the Plan
Administrator or such Employee by reason of the occupying or having occupied positions in
connection with the Plan, except that no indemnification shall be provided if the Plan
Administrator or such Employee personally profited from any act or transaction in respect of which
indemnification is sought.

     6.05 Binding Action. To the fullest extent permitted by law, all actions taken and
decisions made by the Plan Administrator shall be final, conclusive and binding on all persons
having any interest in the Plan or in any benefits payable thereunder.

ARTICLE VII.

POWERS AND DUTIES OF PLAN ADMINISTRATOR

     7.01 Administration Powers. The Plan Administrator shall have the power to take all
action and to make all decisions necessary or proper in order to carry out its duties and
responsibilities under the provisions of the Plan, including without limitation, the following:

     (a) To make and enforce such rules and regulations as the Plan Administrator shall deem
necessary or proper for the efficient administration of the Plan;

     (b) To interpret the Plan and its rules and regulations; and

     (c) To delegate to one or more persons the authority to administer the Plan, with such
duties, powers and authority relative to the administration of the Plan as the Plan
Administrator shall determine, and in so doing to limit its own duties and responsibilities
to the extent specified in such appointment.

     The Plan Administrator shall report to the Compensation Committee of the Board each year
concerning the administration and operation of the Plan.

     7.02 Plan Administrator Claims Review Authority and Procedures. Any claim for
benefits or other payments under the Plan shall be determined in accordance with the procedure set
forth below. A claim for benefits or other payments may be filed by a Participant, the surviving
Spouse of a Participant, a Beneficiary of a Participant or the authorized representative of such
Participant, Surviving Spouse or Beneficiary (the “claimant”).

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     (a) Initial Claim Determination. Any claim for benefits or other payments
under the Plan shall be made by filing a written statement of such claim with the person or
persons designated by the Plan Administrator to process and make initial determinations as
to such claims. In the event such claim is denied in whole or in part, such person or
persons shall notify the claimant of the denial within 90 days after the date on which the
claim was filed. However, if the Plan Administrator determines that special circumstances
require an extension of time for deciding the claim, the Plan Administrator shall furnish
written notice of the extension to the claimant prior to the expiration of such 90 day
period. This notice shall indicate the special circumstances requiring the extension, and
the date by which the Plan expects to render the determination on the claim. If an
extension is taken, and if the claim is denied in whole or in part, the person or persons
who processed and denied the claim shall notify the claimant of the denial within 180 days
after the date on which the claim was filed.

     (b) Initial Notification of Claim Denial. Any notification of a whole or
partial denial of a claim shall be in writing. Such notification shall set forth, in a
manner calculated to be understood by the claimant:

     (i) the specific reason or reasons for the denial;

     (ii) reference to the specific provisions of the Plan on which the denial was
based;

     (iii) a description of any additional material or information necessary for the
claimant to perfect the claim, and an explanation of why such material or
information is necessary; and

     (iv) an explanation of the review procedure under subsection (c), including a
description of the time limits applicable to such procedure and a statement of the
claimant’s right to bring a civil action under Section 502(a) of ERISA following an
adverse determination of the claim on review.

     (c) Review Procedure. A claimant whose claim is denied in whole or in part
under subsection (a) shall be entitled to have such denial reviewed by the Plan
Administrator, by filing a written request for such review with the Plan Administrator
within 60 days after its receipt of the notification of the claim denial under subsection
(b). The claimant may request and shall be provided, free of charge, reasonable access to,
and copies of, all documents, records and other information which is relevant to the claim,
and which is in the possession of the Plan Administrator or Alleghany. The claimant may
provide comments, documents, records and other information relating to the claim to the
Plan Administrator to consider when reviewing the claim. Upon receipt of a request for a
review of a denied claim, the Plan Administrator shall make a full and fair review of the
claim. Such review shall take into account all comments, documents, records and other
information submitted by the claimant relating to the claim, without regard to whether the
same was submitted or considered in the initial claim determination.

- 12 -

 

     (d) Decision on Review. The Plan Administrator shall make a decision with
respect to such claim, and shall notify the claimant of its decision, within 60 days after
its receipt of the claimant’s written request for review. However, if the Plan
Administrator determines that special circumstances, such as the need to hold a hearing,
require an extension of time for deciding the claim, the Plan Administrator shall provide a
written notice of the extension to the claimant prior to the expiration of such 60 day
period. This notice shall indicate the special circumstances requiring the extension, and
the date by which the Plan expects to render the determination on review. If an extension
is taken, the Plan Administrator shall notify the claimant of its decision on the claim
within 120 days after the date on which the request to review the denial of the claim was
filed. However, if the Plan Administrator determines that an extension is needed because
the claimant must submit additional information in order for the Plan Administrator to make
its determination on the claim, and the Plan Administrator requests such additional
information from the claimant in the notification of extension, then the 120 day period for
making the determination on review shall be tolled for the period which starts on the date
on which such notification is sent to the claimant, and which ends on the date on which the
claimant provides such additional information to the Plan Administrator.

     (e) Notification of Decision on Review. The notification of the Plan
Administrator’s decision on review shall be in writing. If the claim is denied, the
notification shall set forth, in a manner calculated to be understood by the claimant:

     (i) the specific reason or reasons for the claim denial;

     (ii) reference to the specific Plan provisions on which the claim denial was
based;

     (iii) a statement that the claimant is entitled to receive, upon request and
free of charge, reasonable access to, and copies of, all documents, records and
other information which is relevant to the claim, and which is in the possession of
the Plan Administrator or Alleghany; and

     (iv) a statement of the claimant’s right to bring an action with respect to the
matter raised in the claim under Section 502(a) of ERISA.

     The Plan Administrator shall provide the claimant with reasonable access to, and copies of,
any documents, records and other information which the claimant is entitled to receive, as
indicated in the notification.

     7.03 Conflicts of Interest. The Plan Administrator shall not participate in the
resolution of any question which relates directly or indirectly to him and which, if applied to
him, would significantly vary his eligibility for, or the amount of, any benefit payable to him.
In cases involving the disqualification under this Section 7.03 of the Plan Administrator, the
questions at issue shall be certified to the Compensation Committee of the Board for resolution.

- 13 -

 

ARTICLE VIII.

LIMITATION OF RIGHTS AND OBLIGATIONS

     8.01 Plan is Voluntary. Although it is the intention of Alleghany that the Plan shall
be continued, the Plan is entirely voluntary on the part of Alleghany and the Plan’s continuance is
not a contractual obligation of Alleghany. Notwithstanding any termination of the Plan by
Alleghany, Alleghany agrees as a contractual obligation with the Participants to pay all amounts as
shall be necessary to provide the retirement benefits accrued by them under the Plan as of the date
of any such termination of the Plan.

     8.02 Creation of Certain Employment Rights. The Plan shall be deemed to constitute a
contract between Alleghany and each Participant and is consideration or inducement for the
employment of the Participant by Alleghany. Notwithstanding the foregoing, nothing contained in
the Plan shall be deemed (a) to give any person the right to be retained in the service of
Alleghany or to be continued as an officer of Alleghany or (b) to interfere with the right of
Alleghany to discharge any person at any time without regard to the effect which such discharge
shall have upon his rights or potential rights, if any, under the Plan.

     8.03 Distributions Only from Alleghany. Each Participant and any other person who
shall claim any retirement benefit or other rights under the Plan shall be entitled to look only to
Alleghany for any payment or benefit, and no member of the Board, officer or employee of Alleghany
shall be liable in any manner if Alleghany shall fail to meet its obligations hereunder. Each
Participant shall be only an unsecured general creditor of Alleghany with respect to the retirement
benefits to which he is entitled under this Plan.

ARTICLE IX.

AMENDMENT AND TERMINATION

     9.01 Amendment. The Plan may be amended, whether prospectively or retroactively, in
whole or in part, at any time, or from time to time, whether upon termination or otherwise, as to
any or all of its provisions, by, or pursuant to authorization contained in, a resolution adopted
by the Board; provided, however, that no amendment may reduce the accrued benefit of any
Participant (calculated as if the Plan then terminated).

     9.02 Termination. The Board may at any time terminate the Plan, in whole or part.

     9.03 Payment of Benefits upon Termination. Upon termination of the Plan, benefits may
be paid directly by Alleghany or by means of insurance and/or annuity contracts purchased from one
or more insurance companies either (a) by payment of the benefits when and as called for under the
Plan until such time as all benefits are paid, or (b) by distribution of the Actuarial Equivalent
of the accrued retirement benefits of each Participant, in cash in one lump sum or (c) by the
purchase of annuity contracts of such type as the Board shall determine; provided, however, that no
payment shall be made in a form or at a time which shall violate Section 409A of the Code. For
this and all other purposes of the Plan, the accrued benefit of any Participant shall equal the
retirement benefit (or the lump sum Actuarial Equivalent thereof) the Participant

- 14 -

 

would have been entitled to receive at the time of reference if his Termination of Employment were
the date of the Plan termination or the time of reference, as the case may be, and the
Participant’s retirement benefits were payable as of the date, and in the form, then elected by the
Participant pursuant to Section 5.07 or as otherwise provided in the Plan.

ARTICLE X.

LIMITATION ON ASSIGNMENT

     10.01 Spendthrift Provision. In order that the benefits hereunder shall be fully
protected against claims of all sorts, direct or otherwise, none of the benefits provided hereunder
to any person shall be assignable or transferable voluntarily, nor shall they be subject to the
claims of any beneficiary or creditor whatsoever, nor subject to attachment, garnishment or other
legal process by any creditor or to the jurisdiction of any bankruptcy court or any insolvency
proceedings by operation of law, or otherwise. No person shall have any right to alienate,
anticipate, pledge, sell, transfer, assign, commute, or encumber any of such benefits voluntarily
or involuntarily.

     10.02 Incompetence of Participant or Beneficiary. If the Plan Administrator receives
evidence satisfactory to him that a person entitled to receive any payment under the Plan is
legally incompetent to receive such payment and to give valid release therefor, such payment may be
made to the guardian, committee, or other representative of such person duly appointed by a court
of competent jurisdiction. If a person or institution other than a guardian, committee, or other
representative of such person who has been duly appointed by a court of competent jurisdiction is
then maintaining or has custody of such incompetent person, the payment may be made to such other
person or institution and the release of such other person or institution shall be valid and
complete discharge for the payment.

ARTICLE XI.

MISCELLANEOUS

     11.01 Governing Laws. This Plan and all provisions thereof shall be construed and
administered according to the laws of the State of New York without giving effect to the principle
of conflicts of law thereof.

11.02 Name. The name of this Plan is the “Alleghany Corporation Retirement Plan.”

     11.03 Titles and Heading not to Control. The titles to the Articles and the headings
of Sections in the Plan are placed herein for convenience of reference only, and in case of any
conflict, the text of this instrument, rather that such titles or headings, shall control.

     11.04 Gender and Person. The masculine pronoun shall include the feminine, the
feminine pronoun shall include the masculine and the singular shall include the plural wherever the
context so requires.

11.05 Preservation of Pre-Amendment Accrued Benefits. Notwithstanding any

- 15 -

 

provision of the Plan to the contrary, each Participant who was employed by Alleghany on December
31, 2006, shall always be entitled to receive no less than the amount of the retirement benefits
(and any related tax distributions) which such Participant had accrued as of December 31, 2006,
payable in such amounts, subject to such adjustments and utilizing such factors and methods
pursuant to the terms and provisions of the Plan as in effect prior to its amendment effective as
of December 31, 2006; provided that the foregoing shall not entitle any Participant to payment of
his retirement benefits prior to the time provided in this Plan as in effect at the time such
retirement benefits commence. The amount of the retirement benefits (and any tax distributions)
that a Participant may be entitled to receive pursuant to the provisions of this Section 11.05 are
in lieu of, and not in addition to, the retirement benefits and entitlements to which such
Participant is then entitled to under this Plan as so amended effective as of December 31, 2006.

     11.06 Alleghany Capital Partners LLC. The Board may designate officers of Alleghany
Capital Partners LLC (“ACP”) to participate in the Plan and accrue benefits hereunder as if each
such designated officer were an officer of Alleghany (each an “ACP Participant”). During the
period such ACP Participant is an officer of ACP, such ACP Participant shall be treated as employed
by, and an officer of, Alleghany for purposes of applying the provisions of the Plan relating to
participation, vesting and the entitlement to, and amount of, retirement benefits.

- 16 -

 

ALLEGHANY CORPORATION RETIREMENT PLAN

EXHIBIT I

Pre-Effective Date Years of Service

					
	 
	 	Years of	 	 
	Name 

Sismondo, Peter
	 	Service at 12/31/88

 

1.0
	 	 

EXHIBIT II

Special Grants of Additional Years of Service

					
	Name
	 	Additional Years of Service

 

	 	 
	Hart, Robert M.
	 	5	 	 

- 17 -

 

EXHIBIT III

Benson Chapman

	 	 	 	 	 
	 	 	Accumulation of
	Retirement	 	Secular Lump Sum
	Age	 	Payment
	63
	 	 	1,851,387	 
	64
	 	 	1,917,111	 
	65
	 	 	1,985,169	 
	66
	 	 	2,055,643	 
	67
	 	 	2,128,618	 
	68
	 	 	2,204,185	 
	69
	 	 	2,282,433	 
	70
	 	 	2,363,459	 
	71
	 	 	2,447,362	 
	72
	 	 	2,534,243	 
	73
	 	 	2,624,209	 
	74
	 	 	2,717,368	 
	75
	 	 	2,813,834	 

Robert Hart

	 	 	 	 	 
	 	 	Accumulation of
	Retirement	 	Secular Lump Sum
	Age	 	Payment
	60
	 	 	5,718,868	 
	61
	 	 	5,921,889	 
	62
	 	 	6,132,116	 
	63
	 	 	6,349,806	 
	64
	 	 	6,575,224	 
	65
	 	 	6,808,644	 
	66
	 	 	7,050,350	 
	67
	 	 	7,300,638	 
	68
	 	 	7,559,810	 
	69
	 	 	7,828,183	 
	70
	 	 	8,106,084	 
	71
	 	 	8,393,850	 
	72
	 	 	8,691,832	 
	73
	 	 	9,000,393	 
	74
	 	 	9,319,906	 
	75
	 	 	9,650,763	 

- 18 -

 

EXHIBIT III (con’t)

Peter Sismondo

	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	Accumulation of	 	Ongoing Single	 	Ongoing Single	 	Accumulation of
	 	 	Retirement	 	Secular Annuity	 	Life Secular	 	Life Tax-Qualified	 	Tax-Qualified
	 	 	Age	 	Payments	 	Annuity Payments	 	Annuity Payments	 	Annuity Payments
	 
	 	 	55	 	 	 	0	 	 	 	140,252	 	 	 	1,473.44	 	 	 	0	 
	 
	 	 	56	 	 	 	143,397	 	 	 	140,252	 	 	 	1,536.59	 	 	 	0	 
	 
	 	 	57	 	 	 	292,731	 	 	 	140,252	 	 	 	1,599.74	 	 	 	0	 
	 
	 	 	58	 	 	 	448,248	 	 	 	140,252	 	 	 	1,662.89	 	 	 	0	 
	 
	 	 	59	 	 	 	610,203	 	 	 	140,252	 	 	 	1,726.03	 	 	 	0	 
	 
	 	 	60	 	 	 	778,862	 	 	 	140,252	 	 	 	1,789.18	 	 	 	0	 
	 
	 	 	61	 	 	 	954,505	 	 	 	140,252	 	 	 	1,852.33	 	 	 	0	 
	 
	 	 	62	 	 	 	1,137,418	 	 	 	140,252	 	 	 	1,915.48	 	 	 	0	 
	 
	 	 	63	 	 	 	1,327,905	 	 	 	140,252	 	 	 	1,978.62	 	 	 	0	 
	 
	 	 	64	 	 	 	1,526,278	 	 	 	140,252	 	 	 	2,041.77	 	 	 	0	 
	 
	 	 	65	 	 	 	1,732,863	 	 	 	140,252	 	 	 	2,104.92	 	 	 	0	 
	 
	 	 	66	 	 	 	1,948,001	 	 	 	140,252	 	 	 	2,104.92	 	 	 	2,152	 
	 
	 	 	67	 	 	 	2,172,045	 	 	 	140,252	 	 	 	2,104.92	 	 	 	4,393	 
	 
	 	 	68	 	 	 	2,405,365	 	 	 	140,252	 	 	 	2,104.92	 	 	 	6,727	 
	 
	 	 	69	 	 	 	2,648,345	 	 	 	140,252	 	 	 	2,104.92	 	 	 	9,158	 
	 
	 	 	70	 	 	 	2,901,384	 	 	 	140,252	 	 	 	2,104.92	 	 	 	11,689	 
	 
	 	 	71	 	 	 	3,164,898	 	 	 	140,252	 	 	 	2,104.92	 	 	 	14,325	 
	 
	 	 	72	 	 	 	3,439,322	 	 	 	140,252	 	 	 	2,104.92	 	 	 	17,070	 
	 
	 	 	73	 	 	 	3,725,108	 	 	 	140,252	 	 	 	2,104.92	 	 	 	19,929	 
	 
	 	 	74	 	 	 	4,022,724	 	 	 	140,252	 	 	 	2,104.92	 	 	 	22,907	 
	 
	 	 	75	 	 	 	4,332,663	 	 	 	140,252	 	 	 	2,104.92	 	 	 	26,007	 

Note: In applying the reduction in Section 4.02, the amounts shown above in this Exhibit III: (i)
as “Accumulations of Secular Annuity Payments” and “Accumulation of Tax-Qualified Annuity Payments”
are converted from a lump sum to the form provided in Article IV on an Actuarial Equivalent basis,
and (ii) as “Annuity Payments” are converted from an annual amount payable monthly of the annuity
form so specified to the form provided in Article IV on an Actuarial Equivalent basis. In each
case, such Actuarial Equivalent basis shall be determined as of the date the Participant’s
retirement benefits commence, and if the date the Participant’s retirement benefits commence is
other than the first day of the month coinciding with or next following the retirement age
indicated, the amount utilized will be based upon the amounts shown above interpolated for
completed months between the retirement ages indicated and the date such retirement benefits
commence.

- 19 -EX-10.2

 

Exhibit 10.2

ALLEGHANY CORPORATION OFFICERS, HIGHLY

COMPENSATED EMPLOYEES AND DIRECTORS

DEFERRED COMPENSATION PLAN

     Alleghany Corporation Officers, Highly Compensated Employees and Directors Deferred
Compensation Plan (the “Plan”), effective as of January 1, 2002, provides for unfunded deferred
compensation arrangements for officers, certain highly compensated employees and directors of
Alleghany Corporation, a Delaware corporation (“Alleghany”), as well as a savings benefit for
officers and certain highly compensated employees of Alleghany.

1. Purposes of the Plan.

     The purposes of the Plan are (i) to provide a means to defer a portion of the compensation of
the officers of Alleghany, highly compensated employees of Alleghany designated by the Board of
Directors of Alleghany (the “Board”) and directors of Alleghany and (ii) to provide a savings
benefit for officers of Alleghany and highly compensated employees of Alleghany designated by the
Board.

2. Administration of the Plan.

     The Plan shall be administered by an officer of Alleghany (the “Plan Administrator”) appointed
by the Board to serve as administrator under the direction of the Board (the “Plan Administrator”).
The Board shall have full power and authority to interpret, construe, administer, and amend the
Plan, provided, however, that no amendment to the Plan shall reduce the benefits to which any
Participant (as defined below) may be entitled hereunder, and the Board’s interpretation and
construction thereof and actions taken thereunder shall be binding on all persons for all purposes.

     3. Participation.

 

 

     All officers who have completed one year of full-time service and other officers and highly
compensated employees of Alleghany designated by the Board (“Savings Benefit Participants”) shall
participate in the Plan in respect of the savings benefit described in section 4(b) hereof, and
directors (“Director Participants”) and officers and certain highly compensated employees of
Alleghany designated by the Board (“Officer Participants”) of Alleghany shall be eligible to
participate in the Plan by deferring amounts described in section 4(c) hereof. The term
“Participants” as used in the Plan shall include Savings Benefit Participants, Director
Participants and Officer Participants collectively.

4. Deferred Compensation.

     (a) Prime Rate Accounts. Alleghany shall establish in respect of each Savings Benefit
Participant a separate book reserve account (“Savings Benefit Prime Rate Account”), and shall
credit to such Savings Benefit Prime Rate Account (or if section 4(e) shall apply, to the Savings
Benefit Common Stock Account described thereunder), for eventual payment on the basis set forth in
section 4(f) hereof, the savings benefit described in section 4(b) below.

     Subject to the limitations set forth in section 4(g) hereof and to such administrative rules
as may be established by the Plan Administrator, each Participant may from time to time enter into
one or more agreements with Alleghany (“Deferred Compensation Agreements”) which in the aggregate
may provide for the establishment of one or more separate book reserve accounts “Deferred
Compensation Prime Rate Accounts” and for the crediting to such Deferred Compensation Prime Rate
Accounts or if section 4(e) shall apply, to the Deferred Compensation Common Stock Accounts of
Officer Participants described thereunder for eventual payment on the basis set forth in section
4(g) below, of the items described in section 4(c) below. Savings

2

 

Benefit Prime Rate Accounts and Deferred Compensation Prime Rate Accounts are together
referred to herein as “Prime Rate Accounts.”

     (b) Savings Benefit. On the 30th days of March, June, September and December of each
year, Alleghany will credit each Savings Benefit Prime Rate Account (or if section 4(e) shall
apply, the Savings Benefit Common Stock Account described thereunder) with an amount equal to 3.75%
of the base annual salary (excluding bonuses, commissions, severance pay, amounts deferred under
this section 4(b) and contributions to employee benefit plans maintained by Alleghany, but
including base annual salary deferred under section 4(c)(1) below) payable to the Savings Benefit
Participant by Alleghany during the quarter then ended.

     (c) Optional Deferral. Deferred Compensation Agreements entered into by Officer
Participants and Director Participants of Alleghany may provide for the deferral of all or any part
of the following (as applicable):

          (1) The base annual salary (determined as provided in section 4(b) above) payable to such
person by Alleghany;

          (2) Directors’ fees payable to such person by Alleghany;

          (3) Entitlements of such person under the Alleghany Corporation Management Incentive Plan or
any similar bonus plan of Alleghany;

          (4) Entitlements of such person under the Alleghany Corporation 2002 Long-Term Incentive Plan,
the Alleghany Corporation 1993 Long-Term Incentive Plan or any successor long-term incentive plan
(collectively, “Long-Term Incentive Plans”); and

3

 

          (5) Any cash bonus to which such person may become entitled other than pursuant to a plan
referred to in section 4(c)(3) or section 4(c)(4).

Amounts described in sections 4(c)(1) through 4(c)(5) shall be credited to the specified Deferred
Compensation Prime Rate Account (or if section 4(e) shall apply, to the Deferred Compensation
Common Stock Account described thereunder) in lieu of payment in the ordinary course and as of the
times when they would have been payable in the ordinary course. Entitlements in Common Stock of
Alleghany shall be valued at the mean between the high and low prices thereof on the New York Stock
Exchange Consolidated Tape on the date of crediting.

     (d) Interest. Amounts credited to a Prime Rate Account shall, while held in such
Prime Rate Account, be deemed to earn interest at the prime rate compounded on an annual basis and
credited to the Prime Rate Account on December 31st of each year or, if earlier, on the date of
transfer or payment of amounts out of such Prime Rate Account. The “prime rate” for purposes
hereof shall mean the rate of interest announced by JP Morgan Chase Bank, N.A. as its prime rate at
the close of the last business day of each month, which rate shall be deemed to remain in effect
through the last business day of the next month.

     (e) Common Stock Accounts. Upon the request of an Officer Participant made by written
notice given to the Plan Administrator, Alleghany shall establish in respect of such Officer
Participant a common stock account (“Savings Benefit Common Stock Account”) to which all or a
portion of the amounts described in section 4(b) shall be credited. A Deferred Compensation
Agreement entered into between an Officer Participant and Alleghany may provide for the
establishment of a common stock account (“Deferred Compensation Common Stock Account”) to which all
or a portion of the amounts deferred thereunder shall be credited;

4

 

provided, however, that the sum of the amounts credited to an Officer
Participant’s Savings Benefit Common Stock Account and Deferred Compensation Common Stock Account
(including amounts credited thereto in respect of dividend income) may at no time exceed an amount
equal to (x) 30% of the cumulative base annual salary (determined as provided in section 4(b)
above) of such Officer Participant during the period in respect of which the savings benefit
referred to in section 4(b) has been credited for such Officer Participant less (y) the sum of the
original credits actually paid out to such Officer Participant in accordance with the provisions of
section 4(f) hereof. Savings Benefit Common Stock Accounts and Deferred Compensation Common Stock
Accounts are together referred to herein as “Common Stock Accounts.”

     Amounts credited to a Common Stock Account shall, while held in such Common Stock Account,
reflect the investment experience which the account would have had if the amount so designated had
been invested (without commissions or other transaction expenses) and held in whole or fractional
shares of common stock of Alleghany (“Alleghany Common Stock”) during such period. Common Stock
Accounts shall be adjusted as appropriate to reflect cash and stock dividends, stock splits, and
other similar distributions or transactions which, from time to time, occur with respect to
Alleghany Common Stock during the appropriate period. Dividends and other distributions shall be
automatically credited to the Common Stock Account at their cash value or the fair market value of
any non-cash dividend or other distribution and shall be deemed to purchase Alleghany Common Stock
on the date of payment thereof. Alleghany Common Stock shall be deemed acquired, and shall be
valued for purposes of payout or transfer, at a price per share equal to the mean between the high
and low prices thereof on the applicable date on the New York Stock Exchange Consolidated Tape.

5

 

     Subject to rules which may be established by the Plan Administrator or by the Board, the
designation of the account to which the amounts described in section 4(b) shall be credited, or the
allocation of such amounts between accounts, may from time to time be changed. Subject to the
provisions of section 5(h) hereof and to rules which may be established by the Plan Administrator
or by the Board, an Officer Participant may direct that amounts credited to a Prime Rate Account be
transferred to a Common Stock Account, or that amounts credited to a Common Stock Account be
transferred to a Prime Rate Account, by written notice given to the Plan Administrator. Except as
may otherwise be agreed to by the Plan Administrator, amounts transferred as set forth above shall
be paid according to the same payout schedule in effect with respect to such amounts prior to the
transfer.

     (f) Payout of Section 4(b) Amounts. All amounts theretofore credited to a Savings
Benefit Prime Rate Account and/or to an Officer Participant’s Savings Benefit Common Stock Account
shall be paid to the Participant in a lump sum (or in such installments as approved by the chief
executive officer of Alleghany in his sole discretion) at the conclusion of the then current
five-year savings benefit deferral period or, if earlier, upon the date of the Participant’s
termination of employment with Alleghany or such date or dates after such termination as approved
by the chief executive officer of Alleghany in his sole discretion. The Board may, at its sole
option, cause any savings benefit deferral period to terminate at such earlier time as the Board
may, in its sole discretion, determine, in which event the next succeeding five-year savings
benefit deferral period shall commence on the day following the date the preceding period
terminated. The first five-year savings benefit deferral period commenced on January 2, 1984 and
terminated on December 15, 1988.

6

 

     Subject to rules which may be established by the Plan Administrator or by the Board, a
Participant may defer payment of all or a portion of the amounts otherwise payable to him
(including as a result of successive deferrals) at the conclusion of each savings benefit deferral
period until completion of the next succeeding savings benefit deferral period or, if earlier,
until the date of the Participant’s termination with Alleghany (or such date or dates after such
termination as approved by the chief executive officer of Alleghany in his sole discretion), by
giving written notice to the Plan Administrator not later than six months prior to the date on
which such amount would otherwise be paid.

     (g) Payout of Section 4(c) Amounts. Each Deferred Compensation Agreement entered into
between Alleghany and a Participant shall set forth the terms for payment in cash of amounts
attributable to compensation deferred thereunder (a “Payout Schedule”) subject to the following:

          (1) A Payout Schedule may provide for a lump sum payment or for payment in annual
installments.

     (2) Payments shall not extend beyond the year in which the Participant attains age 90.

     (3) All payments shall be made in the month of January.

     (4) The amount of each annual installment payment shall be computed by dividing the
then balance of such Deferred Compensation Prime Rate Account and/or Deferred Compensation
Common Stock Account by the number of installments remaining, including the current
installment; provided, however, that a different method of computation may be specified if
agreed to by Alleghany.

7

 

     (5) In addition to the normal payout schedule specified with respect to such Deferred
Compensation Prime Rate Account and/or Deferred Compensation Common Stock Account, special
payout schedules may be specified with respect to such account to apply, respectively, in
the event of (i) the Participant’s disability, (ii) his death or (iii) the termination of
his employment or his ceasing to be a director of Alleghany.

     (6) Notwithstanding the foregoing or any provision of any Deferred Compensation
Agreement, whether in effect as of the date hereof or subsequently entered into, the Board
may at its sole option direct that payment to a Participant of amounts described in section
4(c) shall occur at such earlier time as the Board may, in its sole discretion, designate.

     Deferred Compensation Agreements entered into between a Director Participant and Alleghany may
provide in aggregate for payment in accordance with no more than two Payout Schedules. Deferred
Compensation Agreements entered between an Officer Participant and Alleghany may provide in the
aggregate for payment in accordance with no more than two Payout Schedules applicable to Deferred
Compensation Prime Rate Accounts and two Payout Schedules applicable to Deferred Compensation
Common Stock Accounts.

     (h) Beneficiaries. A Savings Benefit Participant may designate a beneficiary to
receive payment of the value of amounts credited to his Savings Benefit Prime Rate Account and/or
to his Savings Benefit Common Stock Account following the Participant’s death by filing a written
notice with the Plan Administrator. In the case of deferral by a Director Participant of amounts
described in section 4(c), a beneficiary for each Deferred Compensation Prime Rate Account
following a different Payout Schedule may be designated in the Deferred Compensation

8

 

Agreement or Agreements providing for such deferral. In the case of deferral by an Officer
Participant of amounts described in section 4(c), a beneficiary for each Deferred Compensation
Prime Rate Account or Deferred Compensation Common Stock Account following a different Payout
Schedule may be designated in the Deferred Compensation Agreement or Agreements providing for such
deferral. A Participant may at any time, and from time to time, change beneficiaries by filing a
written notice with the Plan Administrator.

     (i) Hardship. Notwithstanding anything herein contained to the contrary, upon the
request of a Participant and based on a showing of financial hardship caused by accident or
illness, or by an event beyond the control of the Participant, the Board may, in its sole
discretion, vary the manner and time of making the payments under section 4(g) from those provided
for in the Participant’s Deferred Compensation Agreement.

     (j) Deferred Compensation Agreements. Deferred Compensation Agreements shall be
entered into by the parties:

          (1) No later than June 15th and December 15th with respect to amounts described in sections
4(c)(1) and 4(c)(2) which would otherwise be payable during the next six calendar months;

          (2) With respect to entitlements under the Alleghany Corporation Management Incentive Plan or
any similar bonus plan, no later than December 15th of the year prior to the year during which the
bonus is earned;

          (3) With respect to entitlements under the Long-Term Incentive Plans, (i) in the case of
awards of performance shares, no later than September 1 of the calendar year preceding the year in
which the Participant would otherwise be entitled to payment with respect

9

 

to such performance shares, and (ii) in the case of other forms of awards, as the Plan
Administrator may designate;

          (4) With respect to any bonus referred to in section 4(c)(5), no less than two weeks prior to
the authorization of such bonus by Alleghany.

The Plan Administrator may prescribe forms of Deferred Compensation Agreement. Deferred
Compensation Agreements shall be executed on behalf of Alleghany either by the Chairman of
the Board or by the President of Alleghany, except that in the case of a Deferred
Compensation Agreement with the Chairman of the Board such Deferred Compensation Agreement
shall be executed on behalf of Alleghany by the President of Alleghany and in the case of a
Deferred Compensation Agreement with the President such Deferred Compensation Agreement
shall be executed on behalf of Alleghany by the Chairman of the Board of Alleghany. Subject
to the provisions of section 5(h) hereof, Deferred Compensation Agreements may be amended or
modified by agreement of the Participant and Alleghany, including amendments or
modifications to extend or accelerate scheduled payments.

5. General Provisions.

     (a) This Plan is intended to constitute a plan which is unfunded and is maintained by
Alleghany primarily for the purpose of providing deferred compensation for the directors, officers
and certain highly compensated employees of Alleghany, representing a select group of management or
highly compensated employees of Alleghany within the meaning of Sections 201(2), 301(a)(3) and
401(a)(1) of the Employee Retirement Income Security Act of 1974, as amended. Nothing in the Plan
shall create, or be construed to create, a trust or fiduciary relationship of any kind between
Alleghany and a Participant, his designated beneficiary, or any

10

 

other person. Any amounts deferred under the Plan shall be construed for all purposes as a
part of the general funds of Alleghany, and any 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 any securities or instruments as a means of hedging its obligations to any
Participant under the Plan, but if it does, neither the Participant, his beneficiary nor any other
person shall have any interest therein or other right to such property. All payments hereunder
shall be made in cash and no Participant shall be entitled hereunder to any shares of Alleghany
Common Stock.

     (b) The right of any Participant to any amount payable pursuant to this Plan shall not be
assigned, transferred, pledged or encumbered except by the laws of descent and distribution.

     (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 the employ of Alleghany as an executive or in
any other capacity.

     (d) The Board may at any time, in its sole discretion, suspend the availability of the Common
Stock Account or impose limitations upon the frequency and amount of transfers to and from the
Common Stock Account.

     (e) No employee benefits to which a Participant would be entitled under any other employee
benefit plan or arrangement maintained by Alleghany for its employees shall be decreased or
modified because of the deferral of salary under the Plan.

     (f) Payment by Alleghany to a Participant or to a Participant’s beneficiary or beneficiaries,
as designated or otherwise determined pursuant to the provisions of the Plan, shall be binding on
all interested parties and on such Participant’s heirs, executors, administrators and

11

 

assigns, and shall discharge Alleghany and its directors, officers and employees from all
claims, demands, actions or causes of action of every kind arising out of or on account of such
Participant’s participation in the Plan, known or unknown, for himself, his heirs, executors,
administrators and assigns.

     (g) Notwithstanding the provisions of sections 4(f) and 4(g) hereof, but subject to section
5(h) hereof, all amounts described in sections 4(b) and 4(c) hereof and credited to a Participant’s
Prime Rate Account and/or an Officer Participant’s Common Stock Account, together with interest
and/or dividend income accrued thereon, shall become immediately due and payable to such
Participant in the event of the liquidation of Alleghany or in the event that a petition shall be
filed or a case commenced in respect of Alleghany (by Alleghany or by any other person) under Title
11 of the United States Code or any other applicable Federal or state bankruptcy, insolvency or
other similar law, or that any court shall appoint a receiver, liquidator, trustee (or similar
official of Alleghany) or order the winding-up or liquidation of the affairs of Alleghany, and such
case or order shall continue unstayed and in effect for a period of sixty consecutive days.

     (h) Notwithstanding any other provision hereof, the Plan Administrator shall give effect to a
transfer of amounts between a Common Stock Account and a Prime Rate Account only if an Officer
Participant directs such transfer by written notice given to the Plan Administrator during the
period beginning on the third business day and ending on the twelfth business day following the
issuance by Alleghany of a press release setting forth its quarterly or annual summary statement of
sales and earnings (“Common Stock Account Transfer Period”). An amendment or modification of a
Payout Schedule set forth in a Deferred Compensation Agreement providing for deferral of amounts
described in section 4(c) hereof and crediting of

12

 

such amounts to a Common Stock Account shall be entered into by Alleghany and an Officer
Participant only during a Common Stock Account Transfer Period. The Plan Administrator may
establish other rules in respect of transfers of amounts to and from Common Stock Accounts and
execution of amendments to Deferred Compensation Agreements providing for crediting of amounts to
Common Stock Accounts.

     (i) All amounts deferred under the Plan shall be subject to employment taxes, and all payments
shall be subject to income tax withholding, if applicable. Each Participant shall make
arrangements satisfactory to Alleghany with respect to the collection of such taxes with respect to
all amounts deferred or payable hereunder.

     (j) The Plan is the successor plan to the Alleghany Corporation Deferred Compensation Plan
(the “Old Plan”). Accordingly, effective as of January 1, 2002, each separate book reserve account
maintained by Alleghany pursuant to the Old Plan as of the close of business on December 31, 2001,
for each person who is or was an officer or director (“Old Plan Participants”) shall be transferred
to, and shall become, a separate book reserve account for such Participant under this Plan, and all
amounts to which any such Old Plan Participant was therefore entitled to under the Old Plan shall
instead be paid pursuant to this Plan. Further, each election and beneficiary designation of an
Old Plan Participant in effect under the Old Plan shall be given effect as if made pursuant to this
Plan. Finally, each reference to the Old Plan in any Deferred Compensation Agreement of an Old
Plan Participant shall be deemed to refer to this Plan.

     (k) The Board may designate officers of Alleghany Capital Partners LLC (“ACP”) to participate
in the Plan and accrue benefits hereunder as if such officer were an officer of Alleghany (each an
“ACP Participant”). During the period an ACP Participant is an officer of

13

 

ACP, such ACP Participant shall be treated as employee of Alleghany and a Savings Benefit
Participant and an Officer Participant for purposes of the Plan.

14

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