exv4w2






Exhibit 4.2




 





ALLEGHANY CORPORATION

as Issuer



AND



THE BANK OF NEW YORK MELLON

as Trustee



FIRST SUPPLEMENTAL INDENTURE



Dated as of September 20, 2010



Supplement to Indenture dated as of September 20, 2010



 










 









 








Table of Contents




	 	 	 	 	 
	 	 	Page
	 
	 	 	 	 
	Article 1

Creation Of The Notes
	 
	 	 	 	 
	Section 1.01. Designation of Series
	 	 	1	 
	Section 1.02. Form of Note; Denomination
	 	 	1	 
	Section 1.03. Limit on Amount of Series
	 	 	2	 
	Section 1.04. Interest
	 	 	2	 
	Section 1.05. Certificate of Authentication
	 	 	2	 
	Section 1.06. No Sinking Fund
	 	 	2	 
	Section 1.07. Issuance in Global Form
	 	 	2	 
	Section 1.08. Other Terms Of Notes
	 	 	3	 
	Section 1.09. Additional Definitions
	 	 	3	 
	 
	 	 	 	 
	Article 2

Redemption Of Notes
	 
	 	 	 	 
	Section 2.01. Optional Redemption by the Company
	 	 	4	 
	Section 2.02. Applicability of Article
	 	 	5	 
	 
	 	 	 	 
	Article 3

Covenants
	 
	 	 	 	 
	Section 3.01. Limitation on Liens; Disposition of Voting Stock
	 	 	5	 
	 
	 	 	 	 
	Article 4

Reports by the Company
	 
	 	 	 	 
	Section 4.01. Amendment
	 	 	6	 
	 
	 	 	 	 
	Article 5

Events of Default
	 
	 	 	 	 
	Section 5.01. Additional Events Of Default
	 	 	6	 
	Section 5.02. Amendment
	 	 	6	 
	 
	 	 	 	 
	Article 6

Amendments, Supplements and Waivers
	 
	 	 	 	 
	Section 6.01. With Consent of Holders
	 	 	7	 
	 
	 	 	 	 
	Article 7

Defeasance and Covenant Defeasance
	 
	 	 	 	 
	Section 7.01. Company’s Option to Effect Defeasance or Covenant Defeasance
	 	 	7	 






 









 






	 	 	 	 	 
	 	 	Page
	 
	 	 	 	 
	Section 7.02. Defeasance and Discharge
	 	 	7	 
	Section 7.03. Covenant Defeasance
	 	 	8	 
	Section 7.04. Conditions to Defeasance or Covenant Defeasance
	 	 	8	 
	Section 7.05. Deposited Money and U.S. Government Obligations to Be Held
in Trust; Miscellaneous Provisions
	 	 	10	 
	Section 7.06. Reinstatement
	 	 	10	 
	 
	 	 	 	 
	Article 8

Miscellaneous
	 
	 	 	 	 
	Section 8.01. Application of First Supplemental Indenture
	 	 	11	 
	Section 8.02. Effective Date
	 	 	11	 
	Section 8.03. Counterparts
	 	 	11	 
	Section 8.04. Liability of the Trustee
	 	 	11	 











 









 








FIRST SUPPLEMENTAL INDENTURE




     This FIRST SUPPLEMENTAL INDENTURE, dated as of September 20, 2010 is entered into by and
between ALLEGHANY CORPORATION, a Delaware corporation, as issuer (the “Company”), and THE BANK OF
NEW YORK MELLON, as Trustee under the Indenture (as hereinafter defined) (the “Trustee”).



RECITALS





	 	 	WHEREAS, the Company and the Trustee are parties to that certain Indenture dated as of
September 20, 2010 (the “Indenture,” all capitalized terms used and not otherwise defined herein
shall have the meanings set forth in the Indenture) providing for the issuance by the Company of
securities from time to time;





     WHEREAS, the Company desires to issue a new series of Securities under the Indenture, and has
duly authorized the creation and issuance of such Securities and the execution and delivery of this
First Supplemental Indenture to modify the Indenture and provide certain additional provisions as
hereinafter described;



     WHEREAS, the Company and the Trustee deem it advisable to enter into this First Supplemental
Indenture for the purposes of establishing the terms of such series of Securities;



     WHEREAS, the execution and delivery of this First Supplemental Indenture has been authorized
by a Board Resolution;



     WHEREAS, concurrent with the execution hereof, the Company has delivered an Officers’
Certificate and has caused its counsel to deliver to the Trustee an Opinion of Counsel; and



     WHEREAS, all things necessary to make this First Supplemental Indenture a valid agreement of
the Company in accordance with its terms have been done, and the execution and delivery thereof
have been in all respects duly authorized by the parties hereto.



     NOW, THEREFORE, for and in consideration of the premises and the purchase of the Securities by
the Holders thereof, it is mutually agreed, for the equal and proportionate benefit of all Holders
of the Notes (as hereinafter defined), as follows:



ARTICLE 1




Creation Of The Notes 




	 	 	Section 1.01. Designation of Series. Pursuant to the terms hereof and Section 301 of
the Indenture, the Company hereby creates a series of Securities designated as the “5.625% Senior
Notes due 2020” (the “Notes”), which Notes shall be deemed “Securities” for all purposes under the
Indenture.





     Section 1.02. Form of Note; Denomination. The Notes shall be substantially in the
form set forth in Exhibit A attached hereto, which is incorporated herein and made part
hereof. The



 









 







Stated Maturity of the principal amount of the Notes shall be September 15, 2020. The Company
will issue the Notes in denominations of $2,000 and integral multiples of $1,000 in excess thereof.



     Section 1.03. Limit on Amount of Series. The Notes shall not exceed U.S. $300,000,000
in aggregate principal amount, and may, upon the execution and delivery of this First Supplemental
Indenture or from time to time thereafter, be executed by the Company and delivered to the Trustee
for authentication, and the Trustee shall thereupon authenticate and deliver said Notes upon a
Company Order and delivery of an Officers’ Certificate and Opinion of Counsel as contemplated by
Section 303 of the Indenture.



     Section 1.04. Interest. The Company shall pay interest on the aggregate principal
amount of the Notes at 5.625% per annum until the principal amount of the Notes is paid or made
available for payment. The Company shall pay interest, semi-annually in arrears on March 15 and
September 15 of each year, or if any such day is not a Business Day, on the next succeeding
Business Day, commencing on March 15, 2011 (each an “Interest Payment Date”) and such interest
shall be paid to the Person in whose name the Note is registered at the close of business on the
Regular Record Date (whether or not a Business Day) immediately preceding the Interest Payment
Date. Interest on the Notes will accrue from the most recent date to which interest has been paid
or, if no interest has been paid, from September 20, 2010. The Company shall pay interest
(including post-petition interest in any proceeding under any bankruptcy law) on overdue
installments of interest (without regard to any applicable grace periods) from time to time on
demand at the same rate to the extent lawful. Interest will be computed on the basis of a 360-day
year of twelve 30-day months.



     Interest, including interest payable at Stated Maturity, shall be payable at the office of the
Company maintained by the Company for such purposes, which shall initially be the Corporate Trust
Office, and may, as the Company shall specify to the Paying Agent in writing by each Regular Record
Date, be paid either (i) by check mailed or delivered to the Holders of the Notes at their
respective addresses set forth in the Security Register or (ii) by wire transfer of immediately
available funds to an account previously specified in writing by the Holder to the Company and the
Trustee; provided, however, that payments to the Depositary will be made by wire transfer of
immediately available funds to the account of the Depositary or its nominee.



     Maturity or redemption of a Note will cause interest to cease to accrue on such Note. The
Company can not reissue a Note that has matured, redeemed or otherwise been cancelled, except for
registration of transfer, exchange or replacement of such Note.



     Section 1.05. Certificate of Authentication. The Trustee’s certificate of
authentication to be borne on the Notes shall be substantially as provided in the Form of Note
attached hereto as Exhibit A.



     Section 1.06. No Sinking Fund. No sinking fund will be provided with respect to the
Notes.



     Section 1.07. Issuance in Global Form. The Notes shall be issued as one or more
Global Notes, representing the aggregate principal amount of the Notes, and shall be deposited



 









 







with the Trustee as custodian for the Depositary. The Notes shall be registered in the name
of Cede & Co., or other nominee of the Depositary.



     Section 1.08. Other Terms of Notes. The other terms of the Notes shall be as
expressly set forth in Article 1, Article 2, Article 4 and Article 5 hereof and Exhibit A
hereto.



     The words “herein”, “hereof” and “hereunder” and other words of similar import refer to this
First Supplemental Indenture as a whole and not to any particular Article, Section or other
subdivision.



     Section 1.09. Additional Definitions. For purposes of this First Supplemental
Indenture, the following terms shall have the following definitions:



     “Calculation Date” means, with respect to any Redemption Date, the third Business Day
immediately preceding the Redemption Date.



     “Comparable Treasury Issue” means the U.S. Treasury security selected by the Independent
Investment Banker as having a maturity comparable to the remaining term (“Remaining Life”) of the
Notes to be redeemed that would be utilized, at the time of selection and in accordance with
customary financial practice, in pricing new issues of corporate debt securities of comparable
maturity to the Remaining Life.



     “Comparable Treasury Price” means, with respect to any Redemption Date, (1) the average of
five Reference Treasury Dealer Quotations for such Redemption Date, after excluding the highest and
lowest Reference Treasury Dealer Quotations, or (2) if fewer than four such Reference Treasury
Dealer Quotations are obtained, the average of all such Reference Treasury Dealer Quotations.



     “Depositary” means The Depository Trust Company, 55 Water Street, New York, New York.



     “Global Note” means a Security that evidences all or part of the Notes and bears the legend
set forth in the Form of Note attached hereto as Exhibit A.



     “Independent Investment Banker” means U.S. Bancorp Investments, Inc., J.P. Morgan Securities
LLC or Wells Fargo Securities, LLC, as specified by the Company, or, if these firms are unwilling
or unable to select the comparable treasury issue, an independent investment banking institution of
national standing appointed by the Company.



     “Interest Payment Date” has the meaning set forth in Section 1 of the Form of Note attached
hereto as Exhibit A.



     “Reference Treasury Dealer” means (1) J.P. Morgan Securities LLC and a primary U.S. government
securities dealer in New York City (a “Primary Treasury Dealer”) selected by each of (A) U.S.
Bancorp Investments, Inc. and (B) Wells Fargo Securities, LLC and their respective successors,
provided, however, that if any of the foregoing shall cease to be a Primary Treasury Dealer, the
Company will substitute therefor another Primary Treasury Dealer and (2) any three other Primary
Treasury Dealers selected by the Company.



 









 





     “Reference Treasury Dealer Quotations” means, with respect to each Reference Treasury Dealer
and any Redemption Date, the average of the bid and asked prices for the Comparable Treasury Issue
(expressed in each case as a percentage of its principal amount) quoted in writing to the Trustee
by such Reference Treasury Dealer at 5:00 p.m., New York City time, on the third Business Day
preceding such Redemption Date.



     “Regular Record Date” means the close of business on each of March 1 and September 1 of each
year whether or not such day is a Business Day.



     “Restricted Subsidiary” means each present or future Subsidiary of the Company, the
consolidated total assets of which constitute at least fifteen percent of the Company’s total
consolidated assets, together with each successor to any such Subsidiary; each such Subsidiary as
of the date hereof being listed in Schedule 1 to this First Supplemental Indenture.



     “Treasury Rate” means, with respect to any Redemption Date, (i) the yield, under the heading
which represents the average for the week immediately preceding the Calculation Date, appearing in
the most recently published statistical release designated “H.15(519)” or any successor publication
which is published weekly by the Board of Governors of the Federal Reserve System and which
establishes yields on actively traded U.S. Treasury securities adjusted to constant maturity under
the caption “Treasury Constant Maturities,” for the maturity corresponding to the Comparable
Treasury Issue (if no maturity is within three months before or after the Remaining Life, yields
for the two published maturities most closely corresponding to the Comparable Treasury Issue will
be determined and the Treasury Rate will be interpolated or extrapolated from such yields on a
straight line basis, rounding to the nearest month); or (ii) if such release (or any successor
release) is not published during the week immediately preceding the Calculation Date or does not
contain such yields, the rate per annum equal to the semiannual equivalent yield to maturity of the
Comparable Treasury Issue, calculated using a price for the Comparable Treasury Issue (expressed as
a percentage of its principal amount) equal to the Comparable Treasury Price for such
Redemption Date.



     “voting stock” has the meaning as that term is defined under the definition of “Subsidiary”
under Section 101 of the Indenture.



ARTICLE 2




Redemption Of Notes



     Pursuant to Section 301(8) of the Indenture, so long as any of the Notes are outstanding, the
following provisions shall be applicable to the Notes:



     Section 2.01. Optional Redemption by the Company.



     (a) At any time and from time to time, the Notes may be redeemed at the option of the Company
for cash, in whole or in part, upon notice as set forth in Section 1104 of the Indenture, at a
redemption price equal to the greater of (a) the principal amount of the Notes or (b) the sum of
the present values of the remaining scheduled payments of principal and interest on the Notes to be
redeemed (not including any portion of such payments of interest accrued to the date of redemption)
discounted to the date of redemption on a semiannual basis (assuming a



 









 







360-day year consisting of twelve 30-day months) at the applicable Treasury Rate plus 45 basis
points, plus, in each case (a) and (b), accrued and unpaid interest on the principal amount
of the Notes being redeemed to but excluding the date of redemption (the “Redemption Price”). The
date of any such redemption is known as the “Redemption Date”. The Treasury Rate will be
calculated on the third Business Day immediately preceding the Redemption Date.



     If the Company redeems fewer than all of the outstanding Notes, the Trustee will select the
Notes to be redeemed in accordance with the provisions of Section 1103 of the Indenture.



     The Notes will be redeemed in integral multiples of $1,000 principal amount.



     The Company may not give notice of any redemption if the Company has defaulted in payment of
interest and the default is continuing.



     (b) At or prior to the time of giving of any notice of redemption to the Holders of any Notes
to be redeemed, the Company shall deliver an Officers’ Certificate to the Trustee setting forth the
calculation of the Redemption Price applicable to such redemption. The Trustee shall be under no
duty to inquire into, may conclusively presume the correctness of, and shall be fully protected in
relying upon, the Redemption Price as so calculated and set forth in such Officers’ Certificate.



     Section 2.02. Applicability of Article. Redemption of the Notes at the election of
the Company, as permitted by any provision of the Notes or this First Supplemental Indenture, shall
be made in accordance with such provision, Article XI of the Indenture and this Article 2.



ARTICLE 3




Covenants



     Pursuant to Section 901(2) of the Indenture, so long as any of the Notes are outstanding, the
following provisions shall be applicable to the Notes:



     Section 3.01. Limitation on Liens; Disposition of Voting Stock.



     (a) Neither the Company nor any Restricted Subsidiaries may use any voting stock of a
Restricted Subsidiary as security for any debt of the Company or other obligations unless all of
the Notes are secured to the same extent as and for so long as that debt or other obligation is so
secured, provided, however that such restriction shall not apply to liens existing at the time a
corporation becomes a Restricted Subsidiary or any renewal or extension of any such liens.



     (b) Except in a transaction otherwise governed by the Indenture, neither the Company nor any
Restricted Subsidiary may issue, sell, assign, transfer or otherwise dispose of any of the voting
stock of a Restricted Subsidiary so long as any Note remains outstanding. Notwithstanding the
foregoing, this limitation shall not apply to any of the following:




     (i) any issuance, sale, assignment, transfer or other disposition made in compliance
with the order of a court or regulatory authority, unless the order was requested by the
Company or a Restricted Subsidiary;



 









 






     (ii) the disposition of any of the voting stock of a Restricted Subsidiary owned by the
Company or by a Restricted Subsidiary for cash or other property having a fair market value
that is at least equal to the fair market value of the disposed stock, as determined in good
faith by the Board of Directors of the Company; or




     (iii) the issuance, sale, assignment, transfer or other disposition of the voting stock
of a Restricted Subsidiary made to the Company or another Restricted Subsidiary.



ARTICLE 4




Reports by the Company



     Section 4.01. Amendment. Section 704 of the Indenture is hereby amended solely with
respect to the series of Securities that consists of the Notes, to read as follows:



     The Company shall file with the Trustee, within 15 days after it files such annual and
quarterly reports, information, documents and other reports with the SEC, copies of its annual and
quarterly report and of the information, documents and other reports (or copies of such portions of
any of the foregoing as the SEC may by rules and regulations prescribe) which the Company is
required to file with the SEC pursuant to Section 13 or 15(d) of the Exchange Act. The Company
also shall comply with the other provisions of TIA Section 314(a).



ARTICLE 5




Events of Default



     Section 5.01. Additional Events Of Default. Pursuant to Sections 301(16) and 501(7)
of the Indenture, so long as any of the Notes are outstanding, the following shall be an Event of
Default with respect to the Notes, in addition to the Events of Default contained in Section 501 of
the Indenture:



     (a) The Company defaults in the payment of the principal amount or Redemption Price with
respect to any Note when such becomes due and payable.



     (b) The Company defaults in payment of any accrued and unpaid interest which default continues
for 30 days.



     Section 5.02. Amendment. Section 501 of the Indenture is hereby amended solely with
respect to the series of Securities that consists of the Notes, as follows:



     (a) By amending paragraph (4) of Section 501 by deleting the number “90” appearing therein and
replacing it with number “60” and by adding the words “of that series” immediately after the words
“Outstanding Securities” appearing therein.



     (b) By deleting the period at the end of paragraph (7) of Section 501 and replacing it with “;
or”, and adding the following paragraph immediately after paragraph (7) in Section 501:



 









 






(8) if any event of default, as defined in any mortgage, senior
indenture or instrument under which there may be issued, or by
which there may be secured or evidenced, any indebtedness of the
Company for money borrowed, whether such indebtedness now exists or
shall hereafter be created, shall happen and shall result in such
indebtedness in principal amount in excess of $35,000,000 becoming
or being declared due and payable prior to the date on which it
would otherwise become due and payable, and such acceleration shall
not be rescinded or annulled within a period of 30 days after there
shall have been given, by registered or certified mail, to the
Company by the Trustee or to the Company and the Trustee by the
Holders of not less than 25% in principal amount of the Outstanding
Securities of that series, a written notice specifying such event
of default and requiring the Company to cause such acceleration to
be rescinded or annulled and stating that such notice is a “Notice
of Default” hereunder.



ARTICLE 6




Amendments, Supplements and Waivers



     Section 6.01. With Consent of Holders. Pursuant to Section 902 of the Indenture, so
long as any of the Notes are outstanding, without the consent of each Holder affected, an
amendment, supplement or waiver, including a waiver pursuant to Section 513 of the Indenture, may
not (in addition to the events described in paragraphs (1) through (3) of Section 902 of the
Indenture) make any change that impairs or adversely affects the right of a Holder to institute
suit for the enforcement of any payment with respect to the Notes.



ARTICLE 7




Defeasance and Covenant Defeasance



     Section 7.01. Company’s Option to Effect Defeasance or Covenant Defeasance. The
Company may elect, at its option at any time, to have Section 7.02 or Section 7.03 applied to the
Notes (as a whole and not in part) upon compliance with the conditions set forth below in this
Article. Any such election shall be evidenced by a Board Resolution.



     Section 7.02. Defeasance and Discharge. Upon the Company’s exercise of its option to
have this Section applied to the Notes (as a whole and not in part), the Company shall be deemed to
have been discharged from its obligations with respect to the Notes as provided in this Section on
and after the date the conditions set forth in Section 7.04 are satisfied (hereinafter called
“Defeasance”). For this purpose, such Defeasance means that the Company shall be deemed to have
paid and discharged the entire indebtedness represented by the Notes and to have satisfied all its
other obligations under the Notes, this First Supplemental Indenture and the Indenture insofar as
the Notes are concerned (and the Trustee, at the expense of the Company, shall execute proper
instruments (in form and substance reasonably acceptable to the Trustee) acknowledging the same),
subject to the following which shall survive until otherwise terminated



 









 







or discharged hereunder: (1) the rights of Holders of Notes to receive, solely from the trust
fund described in Section 7.04 and as more fully set forth in such Section, payments in respect of
the principal of, premium, if any, and interest on the Notes when payments are due, (2) the
Company’s obligations with respect to the Notes under Sections 304, 305, 306, 1002 and 1003 of the
Indenture, (3) the rights, powers, trusts, duties and immunities of the Trustee hereunder and
(4) this Article. Subject to compliance with this Article, the Company may exercise its option to
have this Section applied to the Notes (as a whole and not in part) notwithstanding the prior
exercise of its option to have Section 7.03 applied to the Notes.



     Section 7.03. Covenant Defeasance. Upon the Company’s exercise of its option to have
this Section applied to the Notes (as a whole and not in part), (i) the Company shall be released
from its obligations under Section 3.01 of this First Supplemental Indenture and any covenant
provided pursuant to Section 901(2) of the Indenture for the benefit of the Holders of the Notes
and (ii) the occurrence of any event specified in Section 501(4) of the Indenture (with respect to
Section 3.01 of this First Supplemental Indenture and any such covenants provided pursuant to
Section 901(2) of the Indenture for the benefit of the Holders of the Notes) or Section 501(8) of
the Indenture added by Section 5.02 of this First Supplemental Indenture, shall be deemed not to be
or result in an Event of Default, in each case with respect to the Notes as provided in this
Section on and after the date the conditions set forth in Section 7.04 are satisfied (hereinafter
called “Covenant Defeasance”). For this purpose, such Covenant Defeasance means that, with respect
to the Notes, the Company may omit to comply with and shall have no liability in respect of any
term, condition or limitation set forth in any such specified Section (to the extent so specified
in the case of Section 501(4) or 501(8) of the Indenture), whether directly or indirectly, by
reason of any reference elsewhere herein to any such Section or by reason of any reference in any
such Section to any other provision herein or in any other document, but the remainder of the
Indenture, this First Supplemental Indenture and the Notes shall be unaffected thereby.



     Section 7.04. Conditions to Defeasance or Covenant Defeasance. The following shall be
the conditions to the application of Section 7.02 or Section 7.03 to the Notes:



     (a) The Company shall irrevocably have deposited or caused to be deposited with the Trustee
(or another trustee which satisfies the requirements contemplated by Section 609 of the Indenture
and agrees to comply with the provisions of this Article applicable to it) as trust funds in trust
for the purpose of making the following payments, specifically pledged as security for, and
dedicated solely to, the benefits of the Holders of the Notes, (A) money in an amount, or
(B) U.S. Government Obligations which through the scheduled payment of principal and interest in
respect thereof in accordance with their terms will provide, not later than one day before the due
date of any payment, money in an amount, or (C) a combination thereof, in each case sufficient, in
the opinion of a nationally recognized firm of independent public accountants expressed in a
written certification thereof delivered to the Trustee, to pay and discharge, and which shall be
applied by the Trustee (or any such other qualifying trustee) to pay and discharge, the principal
of, premium, if any, and any installment of interest on the Notes on the respective Stated
Maturities, in accordance with the terms of the Indenture, this First Supplemental Indenture and
the Notes. As used herein, “U.S. Government Obligation” means (x) any security which is (i) a
direct obligation of the United States of America for the payment of which the full faith and
credit of the United States of America is pledged or (ii) an obligation of a Person controlled or
supervised by and acting as an agency or instrumentality of the United States of



 









 







America the payment of which is unconditionally guaranteed as a full faith and credit
obligation by the United States of America, which, in either case (i) or (ii), is not callable or
redeemable at the option of the issuer thereof, and (y) any depositary receipt issued by a bank (as
defined in Section 3(a) (2) of the Securities Act of 1933, as amended) as custodian with respect to
any U.S. Government Obligation which is specified in clause (x) above and held by such bank for the
account of the holder of such depositary receipt, or with respect to any specific payment of
principal of or interest on any U.S. Government Obligation which is so specified and held, provided
that (except as required by law) such custodian is not authorized to make any deduction from the
amount payable to the holder of such depositary receipt from any amount received by the custodian
in respect of the U.S. Government Obligation or the specific payment of principal or interest
evidenced by such depositary receipt.



     (b) In the event of an election to have Section 7.02 apply to the Notes, the Company shall
have delivered to the Trustee an Opinion of Counsel stating that (A) the Company has received from,
or there has been published by, the Internal Revenue Service a ruling or (B) since the date of this
instrument, there has been a change in the applicable federal income tax law, in either case to the
effect that, and based thereon such opinion shall confirm that, the Holders of the Notes will not
recognize gain or loss for federal income tax purposes as a result of the deposit, Defeasance and
discharge to be effected with respect to the Notes and will be subject to federal income tax on the
same amount, in the same manner and at the same times as would be the case if such deposit,
Defeasance and discharge were not to occur.



     (c) In the event of an election to have Section 7.03 apply to the Notes, the Company shall
have delivered to the Trustee an Opinion of Counsel to the effect that the Holders of the Notes
will not recognize gain or loss for federal income tax purposes as a result of the deposit and
Covenant Defeasance to be effected with respect to the Notes and will be subject to federal income
tax on the same amount, in the same manner and at the same times as would be the case if such
deposit and Covenant Defeasance were not to occur.



     (d) No event which is, or after notice or lapse of time or both would become, an Event of
Default with respect to the Notes shall have occurred and be continuing at the time of such deposit
or, with regard to any such event specified in Sections 501(5) and (6) of the Indenture, at any
time on or prior to the 90th day after the date of such deposit (it being understood that this
condition shall not be deemed satisfied until after such 90th day).



     (e) Such Defeasance or Covenant Defeasance shall not cause the Trustee to have a conflicting
interest within the meaning of the Trust Indenture Act with respect to any securities of the
Company.



     (f) Such Defeasance or Covenant Defeasance shall not result in a breach or violation of, or
constitute a default under, any other agreement or instrument to which the Company is a party or by
which it is bound.



     (g) The Company shall have delivered to the Trustee an Opinion of Counsel (which opinion may
be subject to customary assumptions and exceptions) to the effect that after the 91st day following
the deposit, the trust funds will not be subject to the effect of any applicable bankruptcy,
insolvency, reorganization or similar laws affecting creditors’ rights generally.



 









 





     (h) The Company shall have delivered to the Trustee an Officer’s Certificate stating that the
deposit was not made by the Company with the intent of preferring the Holders of the Notes over the
other creditors of the Company with the intent of defeating, hindering, delaying or defrauding
creditors of the Company or others.



     (i) No event or condition shall exist that would prevent the Company from making payments of
the principal of, premium, if any, and interest on the Notes on the date of such deposit or at any
time ending on the 91st day after the date of such deposit.



     (j) Such Defeasance or Covenant Defeasance shall not result in the trust arising from such
deposit constituting an investment company within the meaning of the Investment Company Act of
1940, as amended, unless such trust shall be registered under such Act or exempt from registration
thereunder.



     (k) The Company shall have delivered to the Trustee an Officer’s Certificate and an Opinion of
Counsel, each stating that all conditions precedent under this First Supplemental Indenture to
either Defeasance or Covenant Defeasance, as the case may be, have been complied with.



     Section 7.05. Deposited Money and U.S. Government Obligations to Be Held in Trust;
Miscellaneous Provisions. Subject to the provisions of the last paragraph of Section 1003 of
the Indenture, all money and U.S. Government Obligations (including the proceeds thereof) deposited
with the Trustee or other qualifying trustee (solely for purposes of this Section and Section 7.06,
the Trustee and any such other trustee are referred to collectively as the “Trustee”) pursuant to
Section 7.04 in respect of the Notes shall be held in trust and applied by the Trustee, in
accordance with the provisions of the Notes, this First Supplemental Indenture and the Indenture,
to the payment, either directly or through any such Paying Agent (including the Company acting as
its own Paying Agent) as the Trustee may determine, to the Holders of the Notes, of all sums due
and to become due thereon in respect of principal and any premium and interest, but money so held
in trust need not be segregated from other funds except to the extent required by law.



     The Company shall pay and indemnify the Trustee against any tax, fee or other charge imposed
on or assessed against the U.S. Government Obligations deposited pursuant to Section 7.04 or the
principal and interest received in respect thereof other than any such tax, fee or other charge
which by law is for the account of the Holders of Notes.



     Anything in this Article to the contrary notwithstanding, the Trustee shall deliver or pay to
the Company from time to time upon Company Request any money or U.S. Government Obligations held by
it as provided in Section 7.04 with respect to the Notes which, in the opinion of a nationally
recognized firm of independent public accountants expressed in a written certification thereof
delivered to the Trustee, are in excess of the amount thereof which would then be required to be
deposited to effect the Defeasance or Covenant Defeasance, as the case may be, with respect to the
Notes.



     Section 7.06. Reinstatement. If the Trustee or the Paying Agent is unable to apply
any money in accordance with this Article with respect to any Note by reason of any order or



 









 







judgment of any court or governmental authority enjoining, restraining or otherwise
prohibiting such application, then the obligations under the Indenture, this First Supplemental
Indenture and the Notes from which the Company has been discharged or released pursuant to
Section 7.02 or 7.03 shall be revived and reinstated as though no deposit had occurred pursuant to
this Article with respect to such Note, until such time as the Trustee or Paying Agent is permitted
to apply all money held in trust pursuant to Section 7.05 with respect to such Note in accordance
with this Article; provided, however, that if the Company makes any payment of principal of or any
premium or interest on any such Note following such reinstatement of its obligations, the Company
shall be subrogated to the rights (if any) of the Holders of such Note to receive such payment from
the money so held in trust.



ARTICLE 8




Miscellaneous



     Section 8.01. Application of First Supplemental Indenture. Each and every term and
condition contained in this First Supplemental Indenture that modifies, amends or supplements the
terms and conditions of the Indenture shall apply only to the Notes created hereby and not to any
future series of Securities established under the Indenture. Except as specifically amended and
supplemented by, or to the extent inconsistent with, this First Supplemental Indenture, the
Indenture shall remain in full force and effect and is hereby ratified and confirmed.



     Section 8.02. Effective Date. This First Supplemental Indenture shall be effective as
of the date first above written and upon the execution and delivery hereof by each of the parties
hereto.



     Section 8.03. Counterparts. This First Supplemental Indenture may be executed in any
number of counterparts, each of which so executed shall be deemed to be an original, but all such
counterparts shall together constitute but one and the same instrument.



     Section 8.04. Liability of the Trustee. The Trustee accepts the amendment of the
Indenture effected by this First Supplemental Indenture and agrees to execute the trust created by
the Indenture as hereby amended, but only upon the terms and conditions set forth in the Indenture,
including the terms and provisions defining and limiting the liabilities and responsibilities of
the Trustee, which terms and provisions shall in like manner define and limit its liabilities and
responsibilities in the performance of the trust created by the Indenture as hereby amended.
Without limiting the generality of the foregoing, the Trustee shall not be responsible in any
manner whatsoever for or with respect to any of the recitals or statements contained herein, all of
which recitals or statements are made solely by the Company, or for or with respect to (i) the
validity, efficacy, or sufficiency of this First Supplemental Indenture or any of the terms or
provisions hereof, (ii) the proper authorization hereof by the Company by corporate action or
otherwise, or (iii) the due execution hereof by the Company, and the Trustee makes no
representation with respect to any such matters.



[Signature page follows]






 









 








     IN WITNESS WHEREOF, the parties hereto have caused this First Supplemental Indenture to be
duly executed by their respective officers hereunto duly authorized, all as of the day and year
first above written.



	 	 	 	 	 
	 	ALLEGHANY CORPORATION

 	 
	 	By:  	/s/ Roger B. Gorham
 	 
	 	 	Name:  	Roger B. Gorham 	 
	 	 	Title:  	Senior Vice President – Finance and Chief
Financial Officer 	 
	 
	 	THE BANK OF NEW YORK MELLON, as Trustee

 	 
	 	By:  	/s/ Kimberly Agard
 	 
	 	 	Name:  	Kimberly Agard 	 
	 	 	Title:  	Vice President 	 
	 








 









 








EXHIBIT A




[Face of Security]

5.625% Senior Notes due 2020



     If the registered owner of this security is The Depository Trust Company or a nominee thereof,
the following legend is applicable: THIS SECURITY IS IN GLOBAL FORM WITHIN THE MEANING OF THE
INDENTURE HEREINAFTER REFERRED TO AND IS REGISTERED IN THE NAME OF THE DEPOSITARY (AS HEREINAFTER
DEFINED) OR A NOMINEE OF THE DEPOSITARY OR A SUCCESSOR DEPOSITARY. UNLESS AND UNTIL IT IS
EXCHANGED IN WHOLE OR IN PART FOR SECURITIES IN CERTIFICATED FORM, THIS SECURITY MAY NOT BE
TRANSFERRED EXCEPT AS A WHOLE BY THE DEPOSITARY TO A NOMINEE OF THE DEPOSITARY OR BY A NOMINEE OF
THE DEPOSITARY TO THE DEPOSITARY OR ANOTHER NOMINEE OF THE DEPOSITARY OR BY THE DEPOSITARY OR ANY
SUCH NOMINEE TO A SUCCESSOR DEPOSITARY OR A NOMINEE OF SUCH SUCCESSOR DEPOSITARY.



     UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY
TRUST COMPANY (55 WATER STREET, NEW YORK, NEW YORK) (THE “DEPOSITARY,” OR “DTC”) TO THE COMPANY OR
ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS
REGISTERED IN THE NAME OF CEDE & CO. OR SUCH OTHER NAME AS MAY BE REQUESTED BY AN AUTHORIZED
REPRESENTATIVE OF THE DEPOSITARY (AND ANY PAYMENT IS MADE TO CEDE & CO. OR SUCH OTHER ENTITY AS MAY
BE REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITARY), ANY TRANSFER, PLEDGE OR OTHER USE
HEREOF FOR VALUE OR OTHERWISE BY OR TO ANY PERSON IS WRONGFUL INASMUCH AS THE REGISTERED OWNER
HEREOF, CEDE & CO., HAS AN INTEREST HEREIN.



			
	 	 	 
	CUSIP No. 017175AB6
	 	$300,000,000






     ALLEGHANY CORPORATION, a Delaware corporation, promises to pay to Cede & Co. or registered
assigns, the principal amount of THREE HUNDRED MILLION and no/100 Dollars ($300,000,000) on
September 15, 2020.



     Interest Payment Dates: March 15 and September 15, commencing March 15, 2011.



     Record Dates: March 1 and September 1.



     Reference is hereby made to the further provisions of this Security set forth on the reverse
side of this Security, which further provisions shall for all purposes have the same effect as if
set forth at this place.



     IN WITNESS WHEREOF, the Company has caused this instrument to be duly executed under its
corporate seal.



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	 	ALLEGHANY CORPORATION

 	 
	 	By:  	 	 
	 	 	Name:  	 	 
	 	 	Title:  	 	 
	 



Dated:     , 2010







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TRUSTEE’S CERTIFICATE OF AUTHENTICATION



This is one of the Securities of the series designated therein referred to in the within-mentioned
Indenture:




	 	 	 	 	 	 	 

	 	 	THE BANK OF NEW YORK MELLON, as Trustee	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

	 	 
	 
	 	 	 	 	 	 
	 

	 	 	 	 

Name:
	 	 
	 

	 	 	 	Title:	 	 











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[Back of Security]

5.625% Senior Notes due 2020




     Capitalized terms used herein shall have the meanings assigned to them in the Indenture
referred to below unless otherwise indicated.



     1. INTEREST. Alleghany Corporation, a Delaware corporation (the “Company”) promises to pay
interest on the principal amount of the Notes at 5.625% per annum until the principal amount of the
Notes is paid or made available for payment. The Company shall pay interest, semi-annually in
arrears on March 15 and September 15 of each year, or if any such day is not a Business Day, on the
next succeeding Business Day (each an “Interest Payment Date”), commencing on March 15, 2011.
Interest on the Notes will accrue from the most recent date to which interest has been paid or, if
no interest has been paid, from September 20, 2010. The Company shall pay interest (including
post-petition interest in any proceeding under any bankruptcy law) on overdue principal from time
to time on demand at a rate equal to the per annum rate on the Notes then in effect; it shall pay
interest (including post-petition interest in any proceeding under any bankruptcy law) on overdue
installments of interest (without regard to any applicable grace periods) from time to time on
demand at the same rate to the extent lawful. Interest will be computed on the basis of a 360-day
year of twelve 30-day months.



     2. METHOD OF PAYMENT. Except as provided below, interest will be paid (i) on any Global Notes
to DTC by wire transfer of immediately available funds to the account of DTC or its nominee and
(ii) on any definitive Notes (A) by check mailed or delivered to the Holders of the Notes at their
respective addresses set forth in the Security Register or (B) by wire transfer of immediately
available funds to an account previous specified in writing by the Holder to the Company and the
Trustee.



     The Company may pay interest, including interest payable at Stated Maturity, on definitive
Notes at the Company’s office or agency, which initially will be the Corporate Trust Office of the
Trustee in The City of New York.



     Principal on definitive Notes will be payable, upon Stated Maturity or when due, at the office
or agency of the Company, maintained for such purpose, initially the Corporate Trust Office of the
Trustee in The City of New York.



     Subject to the terms and conditions of the Indenture, the Company will make payments in cash
in respect of Redemption Prices and at Stated Maturity to Holders who surrender Notes to a Paying
Agent to collect such payments in respect of the Notes. The Company will pay cash amounts in money
of the United States that at the time of payment is legal tender for payment of public and private
debts.



     3. PAYING AGENT AND SECURITY REGISTRAR. Initially, The Bank of New York Mellon will act as
Paying Agent and Security Registrar. The Company may appoint and change any Paying Agent, Security
Registrar or co-registrar without notice, other than notice to the Trustee. The Company or any of
its Subsidiaries or any of their Affiliates may act as Paying Agent, Conversion Agent, Security
Registrar or co-registrar.



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     4. INDENTURE. The Company issued the Notes under an Indenture, dated as of September 20, 2010
(the “Base Indenture”), as supplemented by the First Supplemental Indenture dated as of September
20, 2010 (the “First Supplemental Indenture” and, together with the Base Indenture, the
“Indenture”), between the Company and The Bank of New York Mellon, as trustee (the “Trustee”). The
terms of the Notes include those stated in the Indenture and those made part of the Indenture by
reference to the Trust Indenture Act. The Notes are subject to all such terms, and Holders are
referred to the Indenture and such Act for a statement of such terms. The Notes issued under the
Indenture are general unsecured obligations of the Company limited to $300,000,000 in aggregate
principal amount.



     5. OPTIONAL REDEMPTION. At any time and from time to time, the Company may redeem in cash any
portion of the Notes, in whole or in part, at a Redemption Price equal to the greater of (a) the
principal amount of the Notes or (b) the sum of the present values of the remaining scheduled
payments of principal and interest on the Notes to be redeemed (not including any portion of such
payments of interest accrued to the date of redemption) discounted to the date of redemption on a
semiannual basis (assuming a 360-day year consisting of twelve 30-day months) at the applicable
Treasury Rate plus 45 basis points, plus, in each case (a) and (b), accrued and unpaid
interest on the principal amount of the Notes being redeemed to but excluding the date of
redemption (the “Redemption Price”). The date of any such redemption is known as the
“Redemption Date”. The Treasury Rate will be calculated on the third Business Day immediately
preceding the Redemption Date.



     As used in this Note the following terms have the definitions set forth herein:



          “Calculation Date” means, with respect to any Redemption Date, the third Business Day
immediately preceding the Redemption Date.



          “Comparable Treasury Issue” means the U.S. Treasury security selected by the Independent
Investment Banker as having a maturity comparable to the remaining term (“Remaining Life”) of the
Notes to be redeemed that would be utilized, at the time of selection and in accordance with
customary financial practice, in pricing new issues of corporate debt securities of comparable
maturity to the Remaining Life.



          “Comparable Treasury Price” means, with respect to any Redemption Date, (1) the average of
five Reference Treasury Dealer Quotations for such Redemption Date, after excluding the highest and
lowest Reference Treasury Dealer Quotations, or (2) if fewer than four such Reference Treasury
Dealer Quotations are obtained, the average of all such Reference Treasury Dealer Quotations.



          “Independent Investment Banker” means U.S. Bancorp Investments, Inc., J.P. Morgan Securities
LLC or Wells Fargo Securities, LLC, as specified by the Company, or, if these firms are unwilling
or unable to select the comparable treasury issue, an independent investment banking institution of
national standing appointed by the Company.



          “Reference Treasury Dealer” means (1) J.P. Morgan Securities LLC and a primary U.S. government
securities dealer in New York City (a “Primary Treasury Dealer”) selected by each of (A) U.S.
Bancorp Investments, Inc. and (B) Wells Fargo Securities, LLC and



A-5









 







their respective successors, provided, however, that if any of the foregoing shall cease to be
a Primary Treasury Dealer, the Company will substitute therefor another Primary Treasury Dealer and
(2) any three other Primary Treasury Dealers selected by the Company.



          “Reference Treasury Dealer Quotations” means, with respect to each Reference Treasury Dealer
and any Redemption Date, the average of the bid and asked prices for the Comparable Treasury Issue
(expressed in each case as a percentage of its principal amount) quoted in writing to the Trustee
by such Reference Treasury Dealer at 5:00 p.m., New York City time, on the third Business Day
preceding such Redemption Date.



          “Treasury Rate” means, with respect to any Redemption Date, (i) the yield, under the heading
which represents the average for the week immediately preceding the Calculation Date, appearing in
the most recently published statistical release designated “H.15(519)” or any successor publication
which is published weekly by the Board of Governors of the Federal Reserve System and which
establishes yields on actively traded U.S. Treasury securities adjusted to constant maturity under
the caption “Treasury Constant Maturities,” for the maturity corresponding to the Comparable
Treasury Issue (if no maturity is within three months before or after the Remaining Life, yields
for the two published maturities most closely corresponding to the Comparable Treasury Issue will
be determined and the Treasury Rate will be interpolated or extrapolated from such yields on a
straight line basis, rounding to the nearest month); or (ii) if such release (or any successor
release) is not published during the week immediately preceding the Calculation Date or does not
contain such yields, the rate per annum equal to the semiannual equivalent yield to maturity of the
Comparable Treasury Issue, calculated using a price for the Comparable Treasury Issue (expressed as
a percentage of its principal amount) equal to the Comparable Treasury Price for such
Redemption Date.



     In the event the Company redeems less than all of the outstanding Notes, the Notes to be
redeemed shall be selected by the Trustee in accordance with Section 1103 of the Indenture. The
Company may not give notice of any redemption if the Company has defaulted in payment of interest
and the default is continuing.



     6. NOTICE OF REDEMPTION. Notice of redemption will be mailed at least 30 days but not more
than 60 days before the Redemption Date to each Holder of the Notes to be redeemed at such Holder’s
address of record. The Notes in denominations larger than $1,000 may be redeemed in part but only
in integral multiples of $1,000. On and after redemption of a Note pursuant to Section 5 and 6,
interest shall cease to accrue on such Note.



     7. NO MANDATORY REDEMPTION. The Company shall not be required to make mandatory redemption
payments with respect to the Notes. There are no sinking fund payments with respect to the Notes.



     8. DENOMINATIONS; TRANSFER; EXCHANGE. The Notes are in registered form without coupons in
minimum denominations of $2,000 and integral multiples of $1,000 in excess thereof. The transfer
of Notes may be registered and Notes may be exchanged as provided in the Indenture. The Security
Registrar may require a Holder, among other things, to furnish appropriate endorsements and
transfer documents and to pay any taxes and fees required by law or permitted by the Indenture.



A-6









 





     9. PERSONS DEEMED OWNERS. The registered Holder of this Note may be treated as its owner for
all purposes.



     10. AMENDMENT, SUPPLEMENT AND WAIVER. Subject to certain exceptions set forth in the
Indenture, (i) the First Supplemental Indenture or the Notes may be amended with the written
consent of the Holders of a majority in aggregate principal amount of the Notes at the time
outstanding and (ii) certain defaults under the First Supplemental Indenture or the Notes may be
waived with the written consent of the Holders of a majority in aggregate principal amount of the
Notes at the time outstanding. Without the consent of any Holder of the Notes, the First
Supplemental Indenture or the Notes may be amended or supplemented, in addition to other events
more fully described in the Indenture, to cure any ambiguity, defect or inconsistency, to establish
the form or terms of the Securities, to evidence the succession of another corporation to the
Company and the assumption by any such successor of the covenants of the Company contained in the
Indenture, to secure the Securities, and to make any change that does not materially adversely
affect the interests of any Holder under the Indenture.



     11. DEFAULTS AND REMEDIES. If any Event of Default with respect to the Notes shall occur and
be continuing, the principal of all the Notes may be declared due and payable in the manner and
with the effect provided in the Indenture.



     12. TRUSTEE DEALINGS WITH COMPANY. Subject to certain limitations imposed by the
Trust Indenture Act, the Trustee under the Indenture, in its individual or any other capacity, may
become the owner or pledgee of Notes and may otherwise deal with and collect obligations owed to it
by the Company or its Affiliates and may otherwise deal with the Company or its Affiliates with the
same rights it would have if it were not Trustee.



     13. NO RECOURSE AGAINST OTHERS. A director, officer, employee, incorporator or shareholder of
the Company, as such, shall not have any liability for any obligations of the Company under the
Notes or the Indenture or for any claim based on, in respect of, or by reason of, such obligations
or their creation. Each Holder by accepting a Note waives and releases all such liability
including any rights against any such person in its capacity relating to the Company. The waiver
and release are part of the consideration for the issuance of the Notes.



     14. AUTHENTICATION. This Security shall not be valid until authenticated by the manual
signature of the Trustee or an authenticating agent.



     15. ABBREVIATIONS. Customary abbreviations may be used in the name of a Holder or an
assignee, such as: TEN COM (= tenants in common), TEN ENT (= tenants by the entireties), JT TEN (=
joint tenants with right of survivorship and not as tenants in common), CUST (= Custodian), and
U/G/M/A (=Uniform Gifts to Minors Act).



     16. CUSIP NUMBERS. Pursuant to a recommendation promulgated by the Committee on Uniform
Security Identification Procedures, the Company has caused CUSIP numbers to be printed on the Notes
and the Trustee may use CUSIP numbers in notices of redemption as a convenience to Holders. No
representation is made as to the accuracy of such numbers either as printed on the Notes or as
contained in any notice of redemption and reliance may be placed only on the other identification
numbers placed thereon.



A-7









 





     17. UNCLAIMED MONEY OR SECURITIES. The Trustee and the Paying Agent shall return to the
Company upon written request any money or securities held by them for the payment of any amount
with respect to the Notes that remains unclaimed for three years, subject to applicable laws.
After return to the Company, Holders entitled to the money or securities must look to the Company
for payment as general creditors, subject to applicable laws.



     18. DEFEASANCE. Subject to certain conditions set forth in the Indenture, the Company at any
time may terminate some or all of its obligations under the Notes and the First Supplemental
Indenture if the Company deposits with the Trustee money or U.S. Government Obligations for payment
of principal and interest on the Notes to the Stated Maturity.



     19. GOVERNING LAW. THE INDENTURE AND THE NOTES WILL BE GOVERNED BY, AND CONSTRUED IN
ACCORDANCE WITH, THE LAWS OF THE STATE OF NEW YORK.



     The Company shall furnish to any Holder upon written request and without charge a copy of the
Indenture which has in it the text of this Security in larger type. Requests may be made to:



Alleghany Corporation

7 Times Square Tower

New York, NY 10036

Attn: Christopher K. Dalrymple






A-8









 








ASSIGNMENT FORM




To assign this Security, fill in the form below:


I or we assign and transfer this Security to




 





(Insert assignee’s soc. sec. or tax ID no.)



 





 





 





 





(Print or type assignee’s name, address and zip code)




	 	 	 

	and irrevocably appoint
	 	 
	 

	 	 





agent to transfer this Security on the books of the Company. The agent may substitute another to
act for him.




	 	 	 	 	 

	Date:                    

	 	Your Signature:	 	 
	 

	 	 	 	 
	 

	 	 	 	(Sign exactly as your name appears on

the other side of this Security)







A-9