Document:

Restricted Stock Unit Matching Grant Agreement

 Exhibit 10.3 
 ALLEGHANY CORPORATION 
 Restricted Stock Unit Matching Grant Agreement

 Restricted Stock Unit Matching Grant Agreement (“Agreement”), dated as of March 6, 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 (with the defined term “Final Purchase Date” to refer to the date that is 180 days after the Effective Date and not 120 days after the Effective Date) 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. 

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

Section 9. 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 March 6, 2012. 
  

			
		
	By:	 	/s/ Weston M. Hicks
	Name:	 	 Weston M. Hicks

	Title:	 	 President and Chief Executive Officer

  

			
	PARTICIPANT
		
	By:	 	/s/ Joseph P. Brandon
		 	Joseph P. Brandon

  
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 Exhibit 10.4 
 ALLEGHANY CORPORATION 
 Success Shares Award Agreement 

This Success Shares Award Agreement (this “Agreement”), dated as of March 6, 2012, between Alleghany Corporation, a
Delaware corporation (“Alleghany”), and Joseph P. Brandon (the “Participant”). 
 R E C I T A L S :

 WHEREAS, pursuant to the terms of the letter agreement by and between Alleghany and the Participant, dated as of
November 20, 2011 (the “Letter Agreement”), the Participant is entitled to a grant of Success Shares (as defined in the Letter Agreement) on the Effective Date (as defined in the Letter Agreement) in recognition of the services he
provided as a consultant relating to the Merger prior to the Effective Date; and 
 WHEREAS, in connection with the closing of
the transactions contemplated by the Agreement and Plan of Merger by and among Alleghany, Shoreline Merger Sub, LLC (now Shoreline Merger Sub, Inc.) and Transatlantic Holdings, Inc. (the “Merger”), dated as of November 20, 2011, the
Company will grant Success Shares to the Participant on the Effective Date; 
 NOW, THEREFORE, to evidence the Success Shares to
be so granted to the Participant, the Company hereby agrees as follows: 
 Section 1. Success Shares Award.
On the Effective Date (the “Date of Grant”), Alleghany will grant to the Participant, on the terms and conditions hereinafter set forth, a grant of 11,137 fully vested and non-forfeitable shares of Alleghany common stock under the 2007
Long-Term Incentive 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. 
 Section 2.
Restrictions on Transfer. The Success Shares shall not be transferable by the Participant by means of sale, assignment, exchange, encumbrance, pledge, hedge, hypothecation or otherwise until the earliest to occur of (i) the third
anniversary of the Date of Grant, (ii) the termination of the Participant’s employment with Alleghany for any reason including death and Total Disability (as defined in the Letter Agreement), and (iii) 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 Common Stock. Once transferable, any disposition by the Participant shall be made in
compliance with all applicable securities laws and policies of Alleghany. The Participant hereby represents and warrants to Alleghany that the Success Shares are being acquired for investment and not with a view to the distribution thereof, and not
with any present intention of distributing the same. 
 Section 3. Custody and Delivery of Shares. Alleghany
shall hold the certificate or certificates representing the Success Shares subject to this Award until such Success Shares have become transferable pursuant to Section 2 hereof. Upon the Success Shares becoming transferable pursuant to
Section 2 hereof, Alleghany shall deliver or cause to be delivered the certificate or certificates representing such Success Shares to the Participant. 

 Section 4. Rights as a Stockholder. Subject to the otherwise applicable
provisions of the Plan and this Agreement, the Participant will have all rights of a stockholder of the shares of Common Stock in respect of which the Success Shares are granted to the Participant hereunder, including the right to vote the shares
and receive all dividends and other distributions paid in respect thereof. 
 Section 5. Tax Withholding. The
Participant is solely responsible for the payment of all Federal, state, local and foreign taxes that are required by applicable laws or regulations to be paid with respect to the receipt of Success Shares, and under no circumstances whatsoever,
including without limitation, for the purposes of the Federal Insurance Contributions Act, the Social Security Act, the Federal Unemployment Tax Act and Federal and state income tax withholding, will the Participant be deemed to be an employee of
the Company with respect to the grant of the Success Shares. 
 Section 6. Entire Agreement. This Agreement
contains the entire understanding of Alleghany and the Participant with respect to the subject matter hereof. Any amendment or modification of this Agreement shall not be binding unless in writing and signed by Alleghany and the Participant.

 Section 7. 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 March 6, 2012. 
  

			
	ALLEGHANY CORPORATION
		
	By:	 	/s/ Weston M. Hicks
		 	Weston M. Hicks
		 	President and Chief Executive Officer

  

			
	PARTICIPANT
		
		 	/s/ Joseph P. Brandon
		 	Joseph P. Brandon

  
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