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.

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     (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.

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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

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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

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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.

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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    

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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  

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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.

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