Document:

Voting Agreement

 Exhibit 10.1 
 VOTING AGREEMENT 
 THIS VOTING AGREEMENT (this “Agreement”) is made and
entered into as of February 27, 2012, by and between Alleghany Corporation, a Delaware corporation (the “Company”), Davis Selected Advisers, L.P. a Colorado limited partnership (“Stockholder”), and, solely with respect to
Section 5 hereof, Transatlantic Holdings, Inc., a Delaware corporation (“TRH”). 
 RECITALS 

WHEREAS, Stockholder is party to a Voting Agreement, dated as of June 2009 (the “TRH Voting Agreement”), with TRH, relating to
shares of common stock, par value $1.00 per share, of TRH (the “TRH Shares”); 
 WHEREAS, the Company, Shoreline
Merger Sub, LLC, a Delaware limited liability company (now Shoreline Merger Sub, Inc., a Delaware corporation (“Merger Sub”)), and TRH have entered into an Agreement and Plan of Merger, dated as of November 20, 2011 (the “Merger
Agreement”), under which TRH will merge with and into Merger Sub (the “Merger”); 
 WHEREAS, as a result of the
Merger, Stockholder’s TRH Shares will be exchanged for cash and/or shares of common stock, par value $1.00 per share, of the Company (the “Shares”); and 
 WHEREAS, each of Stockholder and the Company desires, for its mutual benefit and protection, to enter into this Agreement with respect to certain matters relating to the voting of the Shares and certain
other matters set forth herein. 
 AGREEMENT 
 NOW, THEREFORE, in consideration of the foregoing recitals and the mutual covenants and agreements herein contained and other good and valuable consideration, the receipt and sufficiency of which are
acknowledged, the parties hereto hereby agree as follows: 
 1. Agreement to Vote. 

(a) The Stockholder hereby agrees to vote all Shares that Stockholder has power to vote in excess of 9.9% of the outstanding Shares (such
number of Shares, the “Excess Shares”) on each matter on which the Excess Shares shall be entitled to vote at every duly called annual or special meeting of stockholders of the Company, and at every postponement or adjournment thereof, or
with respect to any action by written consent in lieu of any meeting of the stockholders of the Company, in a manner proportionate to the vote of the holders of the Shares (other than Stockholder, stockholders of the Company Beneficially Owning more
than 10% of the outstanding Shares and directors and officers of the Company) voting on (and entitled to vote on) such matter. For the purposes of this 

 
Agreement, “Beneficial Ownership”, “Beneficial Owner” and “Beneficially Own” refer to ownership by any person who, directly or indirectly, through any contract,
arrangement, understanding, relationship or otherwise, has or shares (a) voting power which includes the power to vote, or to direct the voting of, such security; and/or (b) investment power which includes the power to dispose, or to
direct the disposition of, such security; and shall otherwise be interpreted in accordance with the term “beneficial ownership” as defined in Rule 13d-3 adopted by the Securities and Exchange Commission under the Securities Exchange Act of
1934, as amended. 
 (b) In the context of a consent solicitation or other action by written consent in lieu of a meeting,
Shares that affirmatively consent will be treated as voting “in favor” of the consent solicitation or other action by written consent in lieu of a meeting, while Shares that do not consent, abstain or do not submit a consent will be
treated as voting “against” the consent solicitation or other action by written consent in lieu of a meeting. 
 2.
Grant of Proxy. 
 (a) Stockholder hereby constitutes and appoints the Company, with full power of substitution, its true
and lawful proxy and attorney-in-fact to vote at any meeting (and any adjournment or postponement thereof) of the Company’s stockholders called for any purpose, or to execute a written consent of stockholders in lieu of any such meeting, all
Excess Shares that are entitled to vote as of the relevant record date in the manner specified in Section 1 hereto. 
 (b)
The proxy and power of attorney granted herein shall be irrevocable during the term of this Agreement, shall be deemed to be coupled with an interest sufficient in law to support an irrevocable proxy and shall revoke all prior proxies granted by
Stockholder. Stockholder shall not grant any proxy to any person which conflicts with the proxy granted herein, and any attempt to do so shall be void. 
 (c) If Stockholder fails for any reason to vote its Excess Shares as required by Section 1 hereof, then the Company shall have the right to vote the Excess Shares at any meeting of the Company’s
stockholders and in any action by written consent of the Company’s stockholders in accordance with Section 1. The vote of the Company shall control in any conflict between a vote of such Excess Shares by the Company and a vote of such
Excess Shares by Stockholder. 
 3. Representations and Warranties of the Stockholder. The Stockholder represents and
warrants to the Company as follows: 
 (a) Organization and Authority. Upon consummation of the Merger, Stockholder will
be the Beneficial Owner of more than 10% of the outstanding Shares. Stockholder is a limited partnership duly formed, validly existing and in good standing under the Laws of the State of Colorado. Stockholder has full legal power and authority, and
has taken all required legal action necessary, to execute and deliver this Agreement and all other agreements, instruments, certificates, notices and other documents as are necessary to 

  
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consummate the transactions contemplated hereby and otherwise to carry out the terms of this Agreement. Stockholder has duly and validly authorized the execution and delivery of this Agreement,
and the consummation of the transactions contemplated hereby has been duly and validly authorized by it and no other proceedings on its part are necessary to authorize the execution and delivery of this Agreement or the consummation of the
transactions contemplated hereby. 
 (b) Enforceability. This Agreement has been duly and validly executed by Stockholder
and, assuming due authorization, execution and delivery by the Company constitutes, the legal, valid and binding agreement of Stockholder, enforceable against Stockholder in accordance with the terms hereof. 

(c) Consents and Approvals. No consent, approval, waiver, authorization, notice or filing is required to be obtained by
Stockholder from, or to be given by it to, or made by it with, any domestic or foreign governmental, legislative, judicial, administrative or regulatory authority, agency, commission, body, court, association or entity (a “Governmental
Entity”) or any other person, in connection with the execution, delivery and performance by Stockholder of this Agreement. 

(d) Non-Contravention. The execution, delivery and performance by Stockholder of this Agreement, and the consummation of the
transactions contemplated hereby, do not and will not (i) violate any provision of its organizational documents; (ii) conflict with, or result in the breach of, or constitute a default under, or result in the termination, cancellation,
modification or acceleration (whether after the filing of notice or the lapse of time or both) of any right or obligation of it under, or result in a loss of any benefit to which it is entitled under, any contract or agreement, or result in the
creation of any liens, claims, encumbrances, mortgages, security interests and charges of any nature whatsoever (“Liens”) (other than as created by this Agreement) upon its assets and properties; or (iii) violate, or result in a
breach of, or constitute a default under any law or order, writ, judgment, injunction, decree or award entered by or with any Governmental Entity to which it is subject, other than, in the cases of clauses (ii) and (iii), conflicts, breaches,
terminations, defaults, cancellations, accelerations, losses, violations or Liens that would not materially impair or delay its ability to perform its obligations hereunder. 
 4. Shares. This Agreement shall govern all Shares now or hereafter Beneficially Owned by Stockholder. 
 5. Entire Agreement. This Agreement constitutes the entire agreement between the parties with respect to the subject matter hereof and supersedes all other prior agreements and understandings, both
written and oral, among the parties with respect to the subject matter hereof. Upon consummation of the Merger, the TRH Voting Agreement shall be deemed null and void without the need for further action by any party thereto. In the event that the
Merger Agreement is terminated prior to consummation of the Merger, this Agreement shall be deemed null and void without the need for further action by any party hereto. 

  
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 6. Notices. All notices, requests, claims, demands and other communications hereunder
shall be in writing and shall be given by delivery in person, by e-mail, by registered or certified mail (postage prepaid, return receipt requested) or sent by nationally-recognized overnight courier to each other party as set forth below or to such
other address as the party to whom notice is to be given may have furnished to the other parties hereto in writing in accordance herewith. Any such notice or communication shall be deemed to have been delivered and received (a) in the case of
personal delivery, on the date of such delivery, (b) in the case of e-mail, on the date sent if confirmation of receipt is received and such notice is also promptly mailed by registered or certified mail (return receipt requested), (c) in
the case of a nationally-recognized overnight courier in circumstances under which such courier guarantees next business day delivery, on the next business day after the date when sent and (d) in the case of mailing, on the fifth business day
following that on which the piece of mail containing such communication is posted: 
  

			
	if to the Company:	 	 Alleghany Corporation
 7
Times Square Tower, 17th Floor

New York, NY 10036
 Attention: Christopher K.
Dalrymple, Esq.
 E-mail: cdalrymple@alleghany.com

		
	with a copy to:	 	 Dewey & LeBoeuf LLP

1301 Avenue of the Americas
 New York, NY
10019
 Attention: Allison Tam, Esq.

E-mail: atam@dl.com

		
	if to Stockholder:	 	 Davis Selected Advisers, L.P.

2949 East Elvira Road, Suite 101
 Tucson, AZ
85756
 Attention: Thomas Tays, Esq.

E-mail: ttays@dsaco.com

		
	with a copy to:	 	 Davis Selected Advisers, L.P.

620 Fifth Avenue
 New York, NY 10020

Attention: Anthony Frazia, CCO
 E-mail:
afrazia@dsaco.com

 7. Severability. Whenever possible, each provision of this Agreement will be interpreted in such
manner as to be effective and valid under applicable law but if any provision of this Agreement is held to be invalid, illegal or unenforceable in any respect under any applicable law or rule in any jurisdiction, such invalidity, illegality or
unenforceability will not affect any other provision or portion of any provision in such jurisdiction, and this Agreement will be reformed, construed and enforced in such jurisdiction as if such invalid, illegal or unenforceable provision or portion
of any provision had never been contained herein. 

  
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 8. Amendments; Waivers; Etc. This Agreement may not be amended, changed,
supplemented, waived or otherwise modified or terminated, except upon the execution and delivery of a written agreement executed by the parties hereto. The failure of any party hereto to exercise any right, power or remedy provided under this
Agreement or otherwise available in respect hereof at law or in equity, or to insist upon compliance by any other party hereto with its obligations hereunder, and any custom or practice of the parties at variance with the terms hereof, shall not
constitute a waiver by such party of its right to exercise any such or other right, power or remedy or to demand such compliance. 
 9. Governing Law; Venue; Specific Performance; Waiver of Jury Trial. THIS AGREEMENT SHALL BE DEEMED TO BE MADE IN AND IN ALL RESPECTS SHALL BE INTERPRETED, CONSTRUED AND GOVERNED BY AND IN
ACCORDANCE WITH THE LAWS OF THE STATE OF DELAWARE WITHOUT REGARD TO THE CONFLICT OF LAW PRINCIPLES THEREOF. The parties hereby irrevocably submit to the exclusive jurisdiction of the courts of the State of Delaware and the Federal courts of the
United States of America located in the State of Delaware solely in respect of the interpretation and enforcement of the provisions of this Agreement and of the documents referred to in this Agreement, and in respect of the transactions contemplated
hereby, and hereby waive, and agree not to assert, as a defense in any action, suit or proceeding for the interpretation or enforcement hereof or of any such document, that it is not subject thereto or that such action, suit or proceeding may not be
brought or is not maintainable in said courts or that the venue thereof may not be appropriate or that this Agreement or any such document may not be enforced in or by such courts, and the parties hereto irrevocably agree that all claims with
respect to such action or proceeding shall be heard and determined in such a Delaware State or Federal court. The parties hereby consent to and grant any such court jurisdiction over the person of such parties and over the subject matter of such
dispute and agree that mailing of process or other papers in connection with any such action or proceeding in the manner provided in Section 6 hereof or in such other manner as may be permitted by applicable law, shall be valid and sufficient
service thereof. 
 The parties agree that irreparable damage would occur and that the parties would not have any adequate
remedy at law in the event that any of the provisions of this Agreement were not performed in accordance with their specific terms or were otherwise breached. It is accordingly agreed that the parties shall be entitled to an injunction or
injunctions to prevent breaches of this Agreement and to enforce specifically the terms and provisions of this Agreement in any Federal court or in Delaware state court, this being in addition to any other remedy to which they are entitled at law or
in equity. 
 EACH PARTY ACKNOWLEDGES AND AGREES THAT ANY CONTROVERSY WHICH MAY ARISE UNDER THIS AGREEMENT IS LIKELY TO INVOLVE
COMPLICATED AND DIFFICULT ISSUES, AND THEREFORE EACH SUCH PARTY HEREBY IRREVOCABLY AND UNCONDITIONALLY WAIVES 

  
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ANY RIGHT SUCH PARTY MAY HAVE TO A TRIAL BY JURY IN RESPECT OF ANY LITIGATION DIRECTLY OR INDIRECTLY ARISING OUT OF OR RELATING TO THIS AGREEMENT OR THE TRANSACTIONS CONTEMPLATED BY THIS
AGREEMENT. EACH PARTY CERTIFIES AND ACKNOWLEDGES THAT (i) NO REPRESENTATIVE, AGENT OR ATTORNEY OF ANY OTHER PARTY HAS REPRESENTED, EXPRESSLY OR OTHERWISE, THAT SUCH OTHER PARTY WOULD NOT, IN THE EVENT OF LITIGATION, SEEK TO ENFORCE THE
FOREGOING WAIVER, (ii) EACH SUCH PARTY UNDERSTANDS AND HAS CONSIDERED THE IMPLICATIONS OF THIS WAIVER, (iii) EACH SUCH PARTY MAKES THIS WAIVER VOLUNTARILY, AND (iv) EACH SUCH PARTY HAS BEEN INDUCED TO ENTER INTO THIS AGREEMENT BY,
AMONG OTHER THINGS, THE WAIVERS AND CERTIFICATIONS IN THIS SECTION 9. 
 10. Counterparts. This Agreement may be executed
in one or more counterparts, each of which shall be deemed to be an original but all of which shall constitute one and the same agreement. 
 11. Further Assurances. At the request of any party to another party or parties to this Agreement, such other party or parties shall execute and deliver such commercially reasonable instruments or
documents to evidence or further effectuate (but not to enlarge) the respective rights and obligations of the parties and to evidence and effectuate any termination of this Agreement in accordance with its terms. 

[Signature page follows.] 

  
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 IN WITNESS WHEREOF, the parties have caused this Agreement to be duly executed as of the day
and year first above written. 
  

			
	DAVIS SELECTED ADVISERS, L.P.
		
	By:	 	 /s/ Anthony Frazia

		 	Name: Anthony Frazia, JD, CRCP
		 	 Title:   Co-Chief Compliance Officer,
             Director of Institutional Operations,
             Compliance & Risk Management

	
	ALLEGHANY CORPORATION
		
	By:	 	 /s/ Christopher K. Dalrymple

		 	Name: Christopher K. Dalrymple
		 	 Title:   Senior Vice President,
             General Counsel and Secretary

 Solely with respect to the provisions of Section 5 hereof: 

 

			
	TRANSATLANTIC HOLDINGS, INC.
		
	By:	 	 /s/ Gary Schwartz

		 	Name: Gary Schwartz
		 	Title:   EVP & General CounselLetter Agreement

 Exhibit 10.2 
 ALLEGHANY CORPORATION 
 7 Times Square Tower 

New York, New York 10036 
 November 20, 2011 
 Joseph P. Brandon 

Dear Joe: 
 This letter
agreement will confirm the terms of your employment with Alleghany Corporation, a Delaware corporation (“Alleghany”), commencing upon the closing of the transactions contemplated by the Agreement and Plan of Merger by and among the
Corporation, Shoreline Merger Sub, LLC and Transatlantic Holdings, Inc. (the “Merger”), dated as of November 20, 2011, as it may be amended from time to time (the “Merger Agreement”). 

Effectiveness: This letter agreement will become effective as of the date on which the Effective Time (as defined in the
Merger Agreement) of the Merger occurs (the “Effective Date”). In the event that the Effective Time does not occur (or the Merger Agreement is terminated pursuant to Section 8 thereof), this letter agreement shall be null and
void ab initio. Further, consistent with the terms of Alleghany’s policy, all obligations of Alleghany and its affiliates hereunder are subject to your completion of a background check and Alleghany’s satisfaction with the findings
thereof, which will be undertaken as soon as practicable following the date hereof. 
 Position: Commencing upon
the Effective Date, you will serve as Executive Vice President of Alleghany, President and Chief Executive Officer of Alleghany Insurance Holdings, LLC, a wholly-owned subsidiary of Alleghany, and Chairman of Transatlantic Holdings, Inc., which as
of the Effective Time shall become, a wholly-owned subsidiary of Alleghany, and will report directly to the Chief Executive Officer of Alleghany (currently, Weston Hicks). In such capacities, you will have primary responsibility for the oversight of
Transatlantic Reinsurance Company, RSUI Group, Inc., Capitol Transamerica Corporation and Pacific Compensation Insurance Company and their respective operating subsidiaries. In addition, you will partner with the Chief Executive Officer of Alleghany
in the strategic development of Alleghany’s insurance and reinsurance businesses. Further, you will perform the duties and exercise the powers usually incident to such offices and/or such other duties and powers as may be reasonably assigned to
you from time to time by the Chief Executive Officer of Alleghany. 
 Base Salary: During your employment with
Alleghany from and after the Effective Date, Alleghany will pay you an initial base salary at an annual rate of $1,000,000, payable pursuant to Alleghany’s usual payroll practices for senior executives. Your base salary will be reviewed
annually for increases but shall not be decreased. 
 Short-Term Incentive: For the 2012 fiscal year of Alleghany
and any fiscal years thereafter, you will participate in Alleghany’s Management Incentive Plan, with a target bonus opportunity of at least 80% of your annualized base salary and a maximum bonus opportunity of 120% of your annualized base
salary. In the event of your termination of employment on or after December 31 of a fiscal year of Alleghany, you shall be eligible to receive an annual bonus in 

 
respect of such completed fiscal year as determined under the terms of the Management Incentive Plan, including the requirement that performance goals be achieved, on the same basis as other
senior executive officers of Alleghany, without regard to the fact that you are not employed on the payment date, provided that, following your termination date and prior to any such payment date, you are not employed by (including prospective
employment pursuant to an offer) or providing services to a business that is competitive with a material business of Alleghany or its affiliated entities. 
 Long Term Incentive: 2012-2015 Award Period. As soon as practicable and in any event within thirty (30) days following the Effective Date, you will receive a grant of performance
shares under the Alleghany Corporation 2007 Long-Term Incentive Plan or any successor equity incentive plan of Alleghany (the “Plan”) for the four-year award period ending December 31, 2015, which will have a fair market value,
as of the date such grant is approved by the Compensation Committee of the Board of Directors of Alleghany (the “Committee”) equal to 160% of your annualized base salary for 2012. These performance shares will have the same terms,
including with respect to share performance conditions, as those granted to other similarly situated executive officers of Alleghany for the four-year award period ending on December 31, 2015. 

Grants for Open Award Periods. As soon as practicable and in any event within thirty (30) days following the Effective Date,
you will receive additional grants of performance shares under the Plan for the performance share award periods ending on December 31 of 2012, 2013 and 2014, respectively, as follows: (i) performance shares for the award period ending
December 31, 2012 with a grant date fair market value of $400,000 (25% of the total opportunity); (ii) performance shares for the award period ending December 31, 2013 with a grant date fair market value of $800,000 (50% of the total
opportunity); and (iii) performance shares for the award period ending December 31, 2014 with a grant date fair market value of $1,200,000 (75% of the total opportunity), in each case subject to the applicable growth in Alleghany’s
stockholder book value performance criteria applicable to the awards in respect of the comparable performance period that were granted to other senior executive officers of Alleghany and, otherwise, subject to such other substantially similar award
terms as awards that were granted to such senior executive officers for such periods. 
 Success Grant: On the
Effective Date, you will receive (i) a grant of 11,137 fully vested and non-forfeitable shares of Alleghany common stock (the “Success Shares”) under the Plan (or, if there are insufficient shares available under the Plan, such
grant will be made pursuant to the inducement grant exception of the New York Stock Exchange, but shall in any event have terms consistent with the Plan), with such number of shares to be equitably adjusted as appropriate to reflect extraordinary
cash and stock dividends, stock splits, major corporate events, and other similar events which may, from time to time, occur with respect to Alleghany between the date hereof and the Effective Date, which shares will be nontransferable by you by
means of sale, assignment, exchange, encumbrance, pledge, hedge or otherwise until the third anniversary of the Effective Date (and in any event, subject to the policies of Alleghany and its affiliates regarding the holding and trading of securities
with respect to Alleghany common stock), and (ii) a lump sum cash payment in the amount of $3,500,000. Notwithstanding the foregoing transfer restriction, the Success Shares will be transferable upon your termination of employment for any
reason, including your death and Total Disability (as defined below), and in 

  
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connection with a merger approved by the Board of Directors of Alleghany effectuated by a tender offer or other major corporate transaction approved by the Board of Directors of Alleghany with
respect to Alleghany common stock. For the avoidance of doubt, in no event shall you be entitled to both the payment hereunder and the similar lump sum payments (other than the Services Fees) under Sections 2 and 4 of the Consultant Engagement
Letter between you and Alleghany of even date herewith. 
 Matching Grant: If following the date hereof and prior
to the date that is 120 days after the Effective Date (the “Final Purchase Date”), you purchase shares of Alleghany common stock, you shall be entitled to be granted a matching restricted stock unit for each share purchased for the
first $5,000,000 worth of Alleghany common stock that you purchase. As soon as reasonably practicable after the first to occur of (i) the date following the Effective Date by which you have purchased the maximum number of shares of Alleghany
common stock eligible for the matching grant, (ii) the date following the Effective Date by which you have delivered written notice to Alleghany that you have purchased all of the shares of Alleghany common stock that you intend to purchase on
or prior to the Final Purchase Date, and (iii) the Final Purchase Date (the earliest of such dates, the “Determination Date”), the Committee will award you a restricted stock unit matching grant under the Plan pursuant to a
restricted stock unit matching grant agreement in the form of Exhibit A hereto. 
 Severance Protection: If
your employment is terminated by Alleghany other than for Cause or other than in the case of your Total Disability, Alleghany will continue to pay your base salary after such termination until such payments aggregate $1,000,000 on a gross basis.
Such payments will be subject to normal withholding and other taxes, and will be paid in accordance with Alleghany’s normal payroll practices applicable to senior executives of Alleghany. For purposes of this letter agreement,
“Cause” shall mean (i) your conviction of a felony (other than a traffic violation), (ii) your willful material failure to implement reasonable directives of the Chief Executive Officer of Alleghany after written notice is
delivered to you, which failure is not corrected within ten days following notice thereof, or (iii) willful gross misconduct in connection with the performance of any of your duties; and “Total Disability” shall mean your
inability to discharge your duties hereunder due to physical or mental illness or accident for one or more periods totaling six months during any consecutive twelve-month period. For purposes of clauses (ii) and (iii) of the definition of
Cause, your action or inaction shall not be considered “willful” unless done or omitted by you (A) intentionally or not in good faith and (B) without reasonable belief that your action or inaction was in the best interest of
Alleghany or any of its affiliates, and shall not include failure to act by reason of physical or mental incapacity. 

Other Benefits: Effective as of the Effective Date, you will be eligible to participate in Alleghany’s Executive
Retirement Plan and Deferred Compensation Plan, as well as all other employee benefit plans, programs, practices or other arrangements in which other senior executives of Alleghany are generally eligible to participate from time to time. In
addition, you will be entitled to all fringe benefits and perquisites which are generally made available by Alleghany to its senior executives. 
 Reimbursements: Alleghany will promptly reimburse you for all reasonable business expenses incurred by you in connection with your duties as an employee, pursuant to Alleghany’s
reimbursement policies for similarly situated executive officers. In the event of 

  
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business travel, you shall be permitted to travel and have hotel accommodations at the same level as other senior executives of Alleghany, including reasonable travel to and from Connecticut and
reasonable overnight accommodations in Manhattan, in each case in connection with the performance of your obligations hereunder. 
 Administrative Support: Following the Effective Date, while you are employed by Alleghany, Alleghany will provide you with reasonable administrative support at your office in Connecticut, at
Alleghany’s expense, which office will be your principal place of employment, subject to any required travel on Alleghany’s business and to performing your services from Alleghany’s offices in Manhattan, in each case, as is necessary
to fulfill your obligations hereunder. 
 Meaning of Termination: The date of your “separation from
service”, as defined in section 409A of the Internal Revenue Code of 1986, as amended (which together with the regulations issued thereunder and other rulings, notices and other guidance issued by the Internal Revenue Service interpreting same
is herein referred to as “Section 409A”) and as determined by applying the default presumptions in Treas. Reg. § 1.409A-l(h)(1)(ii)), shall be treated as the date of your termination of employment for purposes of determining
the time of payment of any amount that becomes payable to you hereunder upon your termination of employment and that is properly treated as a deferral of compensation subject to Section 409A after taking into account all exclusions applicable
to such payment under Section 409A. 
 Section 409A: The payments under this letter agreement are
intended to comply with the provisions of Section 409A or an exception to Section 409A. Any payments that qualify for the “short-term deferral” exception under Treasury Regulations Sections 1.409A-1(b)(4), the “separation
pay” exception under Treasury Regulations 1.409A-l(b)(9)(iii) or any other exception under Section 409A will be paid under the applicable exceptions to the greatest extent possible. Each payment of compensation under this letter agreement
will be treated as a separate payment, and in no event may you, directly or indirectly, designate the calendar year of any compensatory payment under this letter agreement. If on the date your employment is terminated you are a “specified
employee,” then any payments that are required to be made to you pursuant to this Agreement as a result of your employment being terminated that constitute the deferral of compensation (within the meaning of Treasury Regulation
Section 1.409A-l(b)) and that would in the absence of this paragraph have been paid to you within six months and one day of the date your employment is terminated (the “Deferred Compensation Payments”) shall not be paid to you
at the time herein provided, but shall instead be accumulated and paid to you in a lump sum with interest thereon at a rate equal to the yield per annum on the six-month Treasury bills (secondary market) on the date your employment is terminated (as
reported by the Federal Reserve Board) from the date payment would have been made to you hereunder until the date paid, such payment to be made on the earlier of (i) the day after the date that is six months from the date your employment
terminated and (ii) if you shall die prior to the expiration of such six-month period, as soon as practicable, but no later than thirty (30) days, following the date of your death (with payment being made to your estate). For these
purposes, you will be a “specified employee” if, on the date your employment is terminated you are an individual who is, under the method of determination adopted by the Committee designated as, or within the category of employees deemed
to be, a “specified employee” within the meaning and in accordance with Treasury Regulation Section 1.409A-l(i). The Committee shall determine in its 

  
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sole discretion all matters relating to who is a “specified employee” and the application and effect of the change in such determination. All reimbursements provided under this letter
agreement will be provided in accordance with and in compliance with the requirements of Section 409A, including, where applicable, the requirement that (i) the amount of expenses eligible for reimbursement during one calendar year will
not affect the amount of expenses eligible for reimbursement in any other calendar year; (ii) the reimbursement of an eligible expense will be made no later than the last day of the calendar year following the calendar year in which the expense
is incurred; and (iii) the right to any reimbursement will not be subject to liquidation or exchange for another benefit. 

Withholding: Alleghany may withhold from any amounts payable under this letter agreement, or any other benefits received
pursuant hereto, any Federal, state and/or local taxes as shall be required to be withheld under any applicable law or regulation. 
 Entire Agreement; Amendment: This letter agreement and any exhibits hereto contain the entire understanding of you and Alleghany with respect to the subject matter hereof and thereof and,
except as specifically provided herein or therein, cancel and supersede any and all other agreements between you and Alleghany with respect to the subject matter hereof and thereof. Any amendment or modification of this letter agreement shall not be
binding unless in writing and signed by you and Alleghany. This letter agreement may be executed in one or more counterparts, each of which will be deemed an original but all of which together will constitute one and the same instrument. 

Governing Law: This letter agreement shall be governed by and enforceable in accordance with the laws of the State of New
York, without giving effect to the principles of conflict of laws thereof. 
 Miscellaneous. This letter will be
binding upon, inure to the benefit of and be enforceable by, as applicable, each of the Corporation and you and each party’s respective personal or legal representatives, executors, administrators, successors, assigns, heirs, distributees and
legatees. This letter is personal in nature to you and you will not, without the written consent of Alleghany, assign, transfer or delegate any rights or obligations hereunder. Alleghany shall not assign, transfer or delegate any rights or
obligations hereunder, other than as a result of a corporate transaction in which the assignee, transferee or delegate agrees to assume all of Alleghany’s obligations hereunder. 

Indemnification. Alleghany will defend, indemnify, advance expenses and hold you harmless in accordance with its
certificate of incorporation and bylaws now or hereafter in force and provide you with directors’ and officers’ liability insurance at the same level as it provides to its other similarly situated senior executive officers. Your rights and
Alleghany’s obligations under this paragraph will survive the termination or expiration of this letter and of your services to the Alleghany hereunder. 

  
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 If the foregoing accurately expresses our mutual understanding, please execute the enclosed
copy of this letter agreement in the space provided below, and return it to me. 
  

			
	Sincerely yours,
	
	ALLEGHANY CORPORATION
		
	By:	 	/s/ Christopher K. Dalrymple
	Name:	 	Christopher K. Dalrymple
	Title:	 	 Vice President, General Counsel
 and Secretary

  

			
	AGREED AND ACCEPTED:
		
		 	/s/ Joseph P. Brandon
		 	Joseph P. Brandon

  
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 EXHIBIT A 
 ALLEGHANY CORPORATION 
 Restricted Stock Unit Matching Grant Agreement

 Restricted Stock Unit Matching Grant Agreement (“Agreement”), dated as of [•], 2012, between
Alleghany Corporation, a Delaware corporation (“Alleghany”), and Joseph P. Brandon (the “Participant”). 
 Section 1. Restricted Stock Matching Grant. Alleghany hereby grants to the Participant, on the terms and conditions hereinafter set forth and subject thereto, a restricted stock unit matching
grant, as specified in the “Matching Grant” paragraph of the Participant’s employment letter with Alleghany, dated November 20, 2011 (the “Employment Letter”), of one restricted stock unit (a “Restricted
Stock Unit”) for each share of common stock, par value $1.00 per share, of Alleghany (the “Common Stock”) purchased by the Participant (each an “Owned Share”) on or prior to the Determination Date (as
defined in the Employment Letter). This grant has been made by the Compensation Committee of the Board of Directors of Alleghany (the “Committee”) pursuant to the terms of the Alleghany Corporation 2007 Long-Term Incentive Plan (the
“Plan”). The applicable terms of the Plan are incorporated herein by reference. Any terms used but not defined herein shall have the meanings ascribed thereto in the Plan. Any ambiguity between any term used in this Agreement and a
term used in the Plan shall be resolved in favor of and in accordance with the term used in the Plan. Any interpretation, determination or decision made or taken by the Committee regarding the Plan or this Agreement shall be final and binding upon
Alleghany and the Participant. 
 Section 2. Restricted Stock Units. The Restricted Stock Units are notional units
of measurement denominated in shares of Common Stock and, subject to the terms and conditions of this Agreement and the Plan, Alleghany shall pay or provide to the Participant in accordance with Section 5 (x) a payment in cash in respect
of such Restricted Stock Units (as adjusted hereunder) in an amount equal to the Fair Market Value on the applicable Vesting Date (as defined below) of the number of shares of Common Stock equal to the number of Restricted Stock Units (as adjusted
hereunder) to which the Participant is entitled to payment as of the applicable Vesting Date, or (y) a share of Common Stock with respect to each Restricted Stock Unit (as adjusted hereunder) to which the Participant is entitled to payment as
of the applicable Vesting Date, with the form of such payment to be determined in the discretion of the Committee as set forth in Section 5 below. Alleghany shall establish on its books a Restricted Stock Unit Account for the Participant and
shall credit the hereby-granted Restricted Stock Units thereto. The Restricted Stock Unit Account shall be debited in respect of any disposition of Owned Shares as provided in Section 3 hereof. The Restricted Stock Unit Account shall reflect
the investment experience which the account would have had if such account held whole or fractional shares of Common Stock equal to the number of credited Restricted Stock Units. The Restricted Stock Unit Account shall be equitably adjusted as
appropriate to reflect cash and stock dividends, stock splits, and other similar distributions and/or major corporate events which may, from time to time, occur with respect to Alleghany and/or Common Stock prior to the Vesting Date. Dividends and
other distributions shall be automatically credited to the Restricted Stock Unit Account at their cash value or the fair market value of any non-cash dividend or other distribution and shall be deemed to purchase Restricted Stock Units at a price
equal to the Fair Market Value of Common Stock on the date of payment thereof. 

 Section 3. Owned Shares. It is a condition to payment in respect of the
Restricted Stock Units that the Participant shall have maintained unencumbered beneficial ownership of the Owned Shares in respect of which such Restricted Stock Units were credited, and any stock dividends or stock splits paid in respect thereof,
continuously throughout the period commencing with the initial purchase of Owned Shares and ending on the seventh anniversary of the date of grant (the “Ownership Period”), and that the Participant shall not (i) have sold,
assigned, transferred, pledged, or hypothecated the Owned Shares, including any stock dividends paid in respect thereof, or (ii) have engaged in any short sale or other transaction that would have the effect of decreasing his economic risk with
regard to the Owned Shares, including any stock dividends paid in respect thereof, at any time during the Ownership Period (any such action in subsection (i) or (ii) being hereinafter referred to as a “disposition”). In
the event of a disposition of any of the Owned Shares, or related stock dividend shares, during the Ownership Period, the Participant’s Restricted Stock Unit Account shall be debited in an amount equal to one Restricted Stock Unit for each
Owned Share so disposed (the “Disposed Owned Share”), together with the investment experience and dividends and distributions theretofore credited from the date of purchase of the Disposed Owned Share. The Participant shall provide
such evidence and certification of continued satisfaction of such continuous ownership requirement (including certification that he has not effected a disposition of any Owned Shares) from time to time as requested by Alleghany. Evidence of
continued satisfaction of the continuous ownership requirement requested by Alleghany may include certification of ownership by a brokerage or other financial institution. Notwithstanding the requirements set forth in this Section 3, the Owned
Shares, and related stock dividend shares, shall at all times throughout the Ownership Period remain the property of the Participant and be subject to his exclusive control and, with respect thereto, the Participant shall have all rights of a
stockholder of Alleghany. Notwithstanding the foregoing, in the event of your termination of employment for any reason, including your death and Total Disability (as defined in the Employment Letter), and in connection with a merger approved by the
Board of Directors of Alleghany effectuated by a tender offer, or other major corporate transaction approved by the Board of Directors of Alleghany with respect to Alleghany Common Stock, the Ownership Period applicable to the Owned Shares and
related stock dividend shares shall terminate and such Owned Shares shall become freely transferable. 
 Section 4.
Vesting of Restricted Stock Units. The Restricted Stock Units shall vest and become nonforfeitable and be paid, as follows: 
 (a) Subject to the terms of this Section 4, (i) 15% of the Restricted Stock Units included in the Restricted Stock Unit Account as of the date of grant (subject to adjustment in accordance with
the terms of the Plan and Section 2 hereof) shall vest and become nonforfeitable on each of the first six anniversaries of the date of grant, and (ii) 10% of the Restricted Stock Units included in the Restricted Stock Unit Account as of
the date of grant (subject to adjustment in accordance with the terms of the Plan and Section 2 hereof) shall vest and become nonforfeitable on the seventh anniversary of the date of grant (each of the first seven anniversaries of the date of
grant and the date of the Participant’s termination of employment (if applicable), a “Vesting Date”). 

  
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 (b) If the Participant’s employment terminates prior to the seventh
anniversary of the date of grant due to the Participant’s death or Total Disability or by the Company other than for Cause (as defined in the Employment Letter), the number of Restricted Stock Units equal to the product of (i) the number
of Restricted Stock Units that are eligible to vest on the first Vesting Date (as per Section 4(a) above) that would occur immediately following the date of termination and (ii) a fraction, the numerator of which shall be the number of
days elapsed from the Vesting Date immediately preceding the date of termination (as per Section 4(a) above) through the date of termination, and the denominator of which shall be 365, shall vest immediately as of such date of termination and
be paid out as provided hereunder. Except as provided in the prior sentence, upon the Participant’s termination of employment, all of the Restricted Stock Units then remaining in the Participant’s Restricted Stock Unit Account as of the
date of termination shall be forfeited and the Participant shall be entitled to no payments or shares of Common Stock in respect thereof. 
 Section 5. Payment; Tax Withholding. Payment in cash or delivery of shares of Common Stock in respect of Restricted Stock Units which have vested and become nonforfeitable pursuant hereto
shall be made as soon as reasonably practicable after (but in no event more than ten (10) business days after) the applicable Vesting Date, in such combination of cash and shares of Common Stock (valued at Fair Market Value on the Vesting Date)
or all in cash or all in Common Stock, as the Committee may determine. Shares of Common Stock delivered on payment of Restricted Stock Units may be treasury shares, authorized but unissued shares, or both. Payments in respect of, or upon the vesting
of, Restricted Stock Units shall be subject to applicable tax withholding as provided in the Plan. 
 Section 6.
Restrictions on Transfer; Beneficiaries. Neither this Agreement nor any Restricted Stock Units covered hereby may be sold, assigned, transferred, encumbered, hypothecated or pledged by the Participant. The Participant shall be entitled to
select (and change) a beneficiary or beneficiaries to receive any payment in respect of Restricted Stock Units which have vested and become non-forfeitable pursuant hereto following the Participant’s death by giving Alleghany written notice
thereof. In the event of the Participant’s death all references in the Agreement to the Participant shall be deemed, where appropriate, to refer to his beneficiary or estate. Any shares of Common Stock received by the Participant in payment of
Restricted Stock Units may only be disposed of in compliance with all applicable securities laws. 
 Section 7.
Treatment of Restricted Stock Units; No Rights as a Stockholder. Until paid, the amounts credited to the Restricted Stock Unit Account shall be a part of the general assets of Alleghany, and the Participant’s right to receive payment in
respect thereof shall be no greater than the right of any other unsecured general creditor. The Restricted Stock Units, whether or not vested, will not confer upon the Participant any voting or other rights of a stockholder. 

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

  
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 Section 9. Miscellaneous. This Agreement and the Employment Letter contain the
entire understanding of Alleghany and the Participant with respect to the subject matter hereof and thereof and, except as specifically provided herein or therein, cancel and supersede any and all other agreements between Alleghany and the
Participant with respect to the subject matter hereof and thereof. This letter will be binding upon, inure to the benefit of and be enforceable by, as applicable, each of the Alleghany and the Participant and each party’s respective personal or
legal representatives, executors, administrators, successors, assigns, heirs, distributees and legatees. Alleghany shall not assign, transfer or delegate any rights or obligations hereunder, other than as a result of a corporate transaction in which
the assignee, transferee or delegate agrees to assume all of Alleghany’s obligations hereunder. Any amendment or modification of this Agreement shall not be binding unless in writing and signed by Alleghany and the Participant. This Agreement
may be executed in one or more counterparts, each of which will be deemed an original but all of which together will constitute one and the same instrument. 
 Section 10. Governing Law. This Agreement shall be governed by and enforceable in accordance with the laws of the State of New York, without giving effect to the principles of conflict of laws
thereof. 

  
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 IN WITNESS WHEREOF, the Participant has duly executed this Agreement and Alleghany has duly
caused this Agreement to be executed in its name and on its behalf, all as of [•], 2012. 
  

			
	ALLEGHANY CORPORATION
		
	By:	 	 
	Name:	 	
	Title:	 	

  

			
	PARTICIPANT
		
	By:	 	 
		 	Joseph P. Brandon

  
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