EX-4.2



 Exhibit 4.2 

Execution Version 
  

 
  

W. R. BERKLEY CORPORATION 
 TO

 THE BANK OF NEW YORK MELLON, as Trustee 
  

 
 NINTH
SUPPLEMENTAL INDENTURE TO 
 INDENTURE DATED FEBRUARY 14, 2003 

(SENIOR DEBT SECURITIES) 
 Dated as
of as of August 6, 2014 
  
  

4.75% Senior Notes due 2044 
  

 
  







 TABLE OF CONTENTS 
  

							
	 	 	 	  	Page	 
	
	ARTICLE I	  
	
	Relation to Indenture; Definitions	  
			
	 Section 1.1.
	 	RELATION TO INDENTURE	  	 	1	  
	 Section 1.2.
	 	DEFINITIONS	  	 	1	  
	 Section 1.3.
	 	AMENDMENT OF INDENTURE	  	 	2	  
	
	ARTICLE II	  
	
	The Series of Securities	  
			
	 Section 2.1.
	 	TITLE OF THE SECURITIES	  	 	2	  
	 Section 2.2.
	 	LIMITATION ON AGGREGATE PRINCIPAL AMOUNT	  	 	2	  
	 Section 2.3.
	 	PRINCIPAL PAYMENT DATE	  	 	2	  
	 Section 2.4.
	 	INTEREST AND INTEREST RATES	  	 	2	  
	 Section 2.5.
	 	PLACE OF PAYMENT	  	 	3	  
	 Section 2.6.
	 	REDEMPTION	  	 	3	  
	 Section 2.7.
	 	DENOMINATION	  	 	4	  
	 Section 2.8.
	 	CURRENCY	  	 	4	  
	 Section 2.9.
	 	FORM OF NOTES	  	 	4	  
	 Section 2.10.
	 	REGISTRAR AND PAYING AGENT FOR THE NOTES	  	 	4	  
	 Section 2.11.
	 	SINKING FUND OBLIGATIONS	  	 	4	  
	 Section 2.12.
	 	DEFEASANCE AND COVENANT DEFEASANCE	  	 	4	  
	 Section 2.13.
	 	PAYMENT OF TAXES	  	 	5	  
	 Section 2.14.
	 	LIMITATION ON LIENS ON STOCK OF PRINCIPAL SUBSIDIARIES	  	 	5	  
	 Section 2.15.
	 	LIMITATIONS ON ISSUE OR DISPOSITION OF COMMON STOCK OF PRINCIPAL SUBSIDIARIES	  	 	5	  
	 Section 2.16.
	 	IMMEDIATELY AVAILABLE FUNDS	  	 	5	  
	
	ARTICLE III	  
	
	Miscellaneous Provisions	  
			
	 Section 3.1.
	 	TRUSTEE NOT RESPONSIBLE FOR RECITALS	  	 	6	  
	 Section 3.2.
	 	PAYMENT OF EXPENSES UPON RESIGNATION OR REMOVAL	  	 	6	  
	 Section 3.3.
	 	ADOPTION, RATIFICATION AND CONFIRMATION	  	 	6	  
	 Section 3.4.
	 	COUNTERPARTS	  	 	6	  
	 Section 3.5.
	 	GOVERNING LAW	  	 	6	  


  
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 W. R. BERKLEY CORPORATION 

NINTH SUPPLEMENTAL INDENTURE TO 

INDENTURE DATED FEBRUARY 14, 2003 

(SENIOR DEBT SECURITIES) 

$350,000,000 
 4.75% Senior Notes
due 2044 
 NINTH SUPPLEMENTAL INDENTURE, dated as of August 6, 2014, between W. R. BERKLEY CORPORATION, a Delaware corporation (the
“Company”), and THE BANK OF NEW YORK MELLON (formerly known as The Bank of New York), a banking corporation organized under the laws of the State of New York, as Trustee (the “Trustee”). 

RECITALS 
 The Company has
heretofore executed and delivered to the Trustee an indenture for senior debt securities, dated as of February 14, 2003 (the “Indenture”), providing for the issuance from time to time of series of the Company’s Securities. 

Section 3.1 of the Indenture provides for various matters with respect to any series of Securities issued under the Indenture to be
established in an indenture supplemental to the Indenture. 
 Section 9.1(4) of the Indenture provides for the Company and the Trustee
to enter into an indenture supplemental to the Indenture to establish the form or terms of Securities of any series as provided by Sections 2.1 and 3.1 of the Indenture. 

NOW, THEREFORE, THIS NINTH SUPPLEMENTAL INDENTURE WITNESSETH: 

For and in consideration of the premises and the issuance of the series of Securities provided for herein, it is mutually agreed, for the
equal and proportionate benefit of all Holders of the Securities of such series, as follows: 
 ARTICLE I 

RELATION TO INDENTURE; DEFINITIONS 

Section 1.1. RELATION TO INDENTURE. This Ninth Supplemental Indenture constitutes an integral part of the Indenture. 

Section 1.2. DEFINITIONS. For all purposes of this Ninth Supplemental Indenture: 

(a) Capitalized terms used herein without definition shall have the meanings specified in the Indenture; 

(b) All references herein to Articles and Sections, unless otherwise specified, refer to the corresponding Articles and Sections of this Ninth
Supplemental Indenture; and 
 (c) The terms “herein,” “hereof,” “hereunder” and other words of similar import
refer to this Ninth Supplemental Indenture. 
 (d) “Fair Value,” when used with respect to Common Stock, means the fair value
thereof as determined in good faith by the Board of Directors. 
  

  
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 Section 1.3. AMENDMENT OF INDENTURE. This Ninth Supplemental Indenture expressly amends the
Indenture solely with respect to the series of Securities established by this Ninth Supplemental Indenture as follows: 
 (a) The words
“If, but only if, Securities of a series are issuable as Bearer Securities, any” appearing at the beginning of the second sentence of Section 1.4(1) of the Indenture are hereby deleted and the word “Any” is inserted in the
place thereof. 
 (b) Clause (y) of Section 4.2(4)(a) of the Indenture is hereby amended and restated in its entirety to read as
follows: “(y) the principal of (and premium, if any), interest, if any, on, and Additional Amounts, if any, related to such Outstanding Securities and any Coupons appertaining thereto at the Stated Maturity of such principal or installment of
principal or premium, interest or Additional Amounts and”. 
 (c) Section 5.1(7) of the Indenture is amended such that: 

 

	 	1.	the words “, rehabilitation” are added after the words “(other than a reorganization under a foreign law that does not relate to insolvency)” appearing in subsection (a) thereof;


  

	 	2.	the words “, rehabilitation” are added after the words “arrangement, adjustment” appearing in subsection (b) thereof; and 


 

	 	3.	the words “, rehabilitator” are added after the words “custodian, receiver, liquidator, assignee, trustee” appearing in subsection (c) thereof. 


(d) Section 5.1(8) of the Indenture is amended such that: 
  

	 	1.	the words “, rehabilitation” are added after the words “(other than a reorganization under a foreign law that does not relate to insolvency)” appearing therein; 


 

	 	2.	the words “, rehabilitation” are added after the words “reorganization, arrangement, adjustment” appearing therein; 


 

	 	3.	the words “or any Principal Subsidiary” are added after the fourth occurrence of the word “Company” appearing therein; and 


 

	 	4.	the words “, rehabilitator” are added after the words “custodian, receiver, liquidator, assignee, trustee” appearing therein. 


ARTICLE II 
 THE SERIES OF
SECURITIES 
 Section 2.1. TITLE OF THE SECURITIES. There shall be a series of Securities designated the “4.75% Senior Notes due
2044” (the “Notes”). 
 Section 2.2. LIMITATION ON AGGREGATE PRINCIPAL AMOUNT. The aggregate principal amount of the
Notes shall initially be limited to $350,000,000. The Company may, without the consent of the Holders of the Notes, issue additional Securities having the same interest rate, maturity date and other terms as described in the related prospectus
supplement and prospectus; provided that such additional Securities shall be fungible for U.S. federal income tax purposes with the previously issued Notes. Any additional Securities, together with the Notes offered by the related prospectus
supplement, will constitute a single series of Securities under the Indenture. No additional Securities may be issued if an Event of Default under the Indenture has occurred and is continuing with respect to the Securities. 

Section 2.3. PRINCIPAL PAYMENT DATE. The principal amount of the Notes outstanding (together with any accrued and unpaid interest) shall
be payable in a single installment on August 1, 2044, which date shall be the Stated Maturity of the Notes Outstanding. 

Section 2.4. INTEREST AND INTEREST RATES. The rate of interest on each Note shall be 4.75% per annum, accruing from August 6,
2014, or from the most recent interest payment date (each such date, an “Interest Payment Date”) to which interest has been paid or duly provided for, payable semiannually in arrears on February 1 and August 1 of each year
commencing February 1, 2015 until the principal thereof shall have become due and 

  
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payable, and until the principal thereof is paid or duly provided for or made available for payment. The amount of interest payable on any Interest Payment Date shall be computed on the basis of
a 360-day year comprised of twelve 30-day months. The amount of interest payable for any partial period shall be computed on the basis of the actual number of days elapsed in a 360-day year of twelve 30-day months. In the event that any date on
which interest is payable on any Note is not a Business Day, then payment of interest payable on such date will be made on the next succeeding day that is a Business Day (and without any interest or other payment in respect of any such delay). The
interest installment so payable in respect of any Note, and punctually paid or duly provided for, on any Interest Payment Date will, as provided in the Indenture, be paid to the person in whose name such Note (or one or more Predecessor Securities)
is registered at the close of business on the January 15 or July 15 prior to such Interest Payment Date. Any such interest installment not punctually paid or duly provided for in respect of any Note shall forthwith cease to be payable to
the registered Holder on such Regular Record Date and may either be paid to the Person in whose name such Note (or one or more Predecessor Securities) is registered at the close of business on a Special Record Date to be fixed by the Company and the
Trustee for the payment of such Defaulted Interest, notice whereof shall be given to the Holders of the Notes not less than 10 days prior to such Special Record Date, or be paid at any time in any other lawful manner not inconsistent with the
requirements of any securities exchange on which the Notes may be listed, and upon such notice as may be required by such exchange, all as more fully provided in the Indenture. 

Section 2.5. PLACE OF PAYMENT. The Place of Payment where the Notes may be presented or surrendered for payment, where the Notes may be
surrendered for registration of transfer or exchange and where notices and demand to or upon the Company in respect of the Notes and the Indenture may be served shall be the Corporate Trust Office of the Trustee. 

Section 2.6. REDEMPTION. 

(a) The Company may redeem the Notes at its option, in whole or in part, at any time and from time to time at a Redemption Price equal to the
greater of (i) 100% of the principal amount of such Securities to be redeemed and (ii) an amount, as determined by an Independent Investment Banker, equal to the sum of the present values of the remaining scheduled payments of principal of
and interest on the securities to be redeemed (not including any portion of such payments of interest accrued as of the Redemption Date) discounted to the Redemption Date on a semiannual basis (assuming a 360-day year consisting of twelve 30-day
months) at the Adjusted Treasury Rate, plus 25 basis points, plus, in either of the above cases, accrued and unpaid interest thereon to, but not including, the Redemption Date. 

(b) For the purposes of this Section 2.6, 

“Adjusted Treasury Rate” means, with respect to any Redemption Date: 

 

	 	•	 	the yield, under the heading which represents the average for the immediately preceding week, appearing in the most recently published statistical release designated “H.15(519)” published by the Board of
Governors of the Federal Reserve System (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 United States 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 (as defined below), yields for
the two published maturities most closely corresponding to the Comparable Treasury Issue shall be determined and the Adjusted Treasury Rate shall be interpolated or extrapolated from such yields on a straight line basis, rounding to the nearest
month; or 

  

	 	•	 	if such release (or any successor release) is not published during the week preceding the calculation date or does not contain such yields, the rate per annum equal to the semi-annual 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. 


The Adjusted Treasury Rate shall be calculated on the third Business Day preceding the Redemption Date. 

  
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 “Comparable Treasury Issue” means, with respect to any Redemption Date, the United
States Treasury security selected by an Independent Investment Banker as having a maturity comparable to the remaining term 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 term of those securities (“Remaining Life”). 

“Comparable Treasury Price” means, with respect to any Redemption Date, (i) the average of three Reference Treasury Dealer
Quotations for such Redemption Date, after excluding the highest and lowest Reference Treasury Dealer Quotations, or (ii) if the Independent Investment Banker obtains fewer than three such Reference Treasury Dealer Quotations, the average of
all such quotations. 
 “Independent Investment Banker” means, with respect to any Redemption Date, one of the Reference Treasury
Dealers appointed by us. 
 “Reference Treasury Dealer” means, with respect to any Redemption Date: 

 

	 	•	 	each of J.P. Morgan Securities LLC, Morgan Stanley & Co. LLC, a Primary Treasury Dealer (as defined below) selected by Wells Fargo Securities, LLC (or any affiliate of any of the foregoing that is a Primary
Treasury Dealer), and their respective successors; provided that, if any of the foregoing ceases to be a primary U.S. Government securities dealer in the United States (a “Primary Treasury Dealer”), the Company shall substitute
another Primary Treasury Dealer; and 

  

	 	•	 	any other Primary Treasury Dealer selected by the Company. 

 “Reference Treasury Dealer
Quotations” means, with respect to each Reference Treasury Dealer and any Redemption Date, the average, as determined by the Independent Investment Banker, 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 Independent Investment Banker at 5:00 p.m., New York City Time, on the third Business Day preceding such Redemption Date. 

The Company will mail a notice of redemption at least 30 days but not more than 60 days before the Redemption Date to each
holder of notes to be redeemed. If less than all of the notes are to be redeemed, the trustee will select in a fair and appropriate manner, including pro rata or by lot, the notes to be redeemed in whole or in part; provided that if the
notes are represented by global notes and such global notes are held by The Depository Trust Company, beneficial interests in the notes will be selected for redemption by The Depository Trust Company in accordance with its standard procedures
therefor.  
 Unless the Company defaults in payment of the Redemption Price, on and after the Redemption Date, interest will cease
to accrue on the notes or portions thereof called for redemption. 
 Section 2.7. DENOMINATION. The Notes shall be issuable only in
registered form without coupons and in denominations of $1,000 and integral multiples thereof. 
 Section 2.8. CURRENCY. Principal and
interest on the Notes shall be payable in such coin or currency of the United States of America that at the time of payment is legal tender for payment of public and private debts. 

Section 2.9. FORM OF NOTES. The Notes shall be substantially in the form attached as EXHIBIT A hereto. 

Section 2.10. REGISTRAR AND PAYING AGENT FOR THE NOTES. The Trustee shall serve initially as Registrar and Paying Agent for the Notes.

 Section 2.11. SINKING FUND OBLIGATIONS. The Company has no obligation to redeem or purchase any Notes pursuant to any sinking fund
or analogous requirement or upon the happening of a specified event or at the option of a Holder thereof. 
 Section 2.12. DEFEASANCE
AND COVENANT DEFEASANCE. The Company has elected to have both Section 4.2(2) of the Indenture (relating to defeasance) and Section 4.2(3) (relating to covenant defeasance) applied to the Notes. 

  
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 Section 2.13. PAYMENT OF TAXES. The Company will pay or discharge or cause to be paid or
discharged, before the same shall become delinquent, all taxes, assessments and governmental charges levied or imposed upon the Company or any Subsidiary or upon the income, profits or property of the Company or any Subsidiary, and lawful claims for
labor, materials and supplies, which, if unpaid, might by law become a lien upon the property of the Company or any Subsidiary; provided, however, that the Company shall not be required to pay or discharge or cause to be paid or
discharged any such tax, assessment or governmental charge whose amount, applicability or validity is being contested in good faith by appropriate proceedings or where the failure to effect such payment is not adverse in any material respect to the
Holders of the Notes. 
 Section 2.14. LIMITATION ON LIENS ON STOCK OF PRINCIPAL SUBSIDIARIES. The Company will not, and it will not
permit any Subsidiary of the Company to, at any time directly or indirectly create, assume, incur or permit to exist any Indebtedness secured by a pledge, lien or other encumbrance (any pledge, lien or other encumbrance being hereinafter in this
Section referred to as a “lien”) on the voting securities of Principal Subsidiaries, or the voting securities of a Subsidiary that owns, directly or indirectly, the voting securities of any of the Principal Subsidiaries, or any subsidiary
succeeding to any substantial part of the business conducted by any Principal Subsidiary, without making effective provision whereby the Notes then Outstanding (and, if the Company so elects, any other Indebtedness of the Company that is not
subordinate to the Notes and with respect to which the governing instruments require, or pursuant to which the Company is otherwise obligated or required, to provide such security) shall be equally and ratably secured with such secured Indebtedness
so long as such other Indebtedness shall be secured. For purposes of this Section 2.14 only, “Indebtedness”, in addition to those items specified in Section 1.1 of the Indenture, shall include any obligation of, or any such
obligation guaranteed by, any Person for the payment of amounts due under a swap agreement or other similar instrument or agreement or foreign currency hedge exchange or similar instrument or agreement. 

If the Company shall hereafter be required to secure the Notes equally and ratably with any other Indebtedness pursuant to this Section,
(i) the Company will promptly deliver to the Trustee an Officer’s Certificate stating that the foregoing covenant has been complied with, and an Opinion of Counsel stating that in the opinion of such counsel the foregoing covenant has been
complied with and that any instruments executed by the Company or any Subsidiary of the Company in the performance of the foregoing covenant comply with the requirements of the foregoing covenant and (ii) the Trustee is hereby authorized to
enter into an indenture or agreement supplemental hereto and to take such action, if any, as it may deem advisable to enable it to enforce the rights of the holders of the Notes so secured. 

Section 2.15. LIMITATIONS ON ISSUE OR DISPOSITION OF COMMON STOCK OF PRINCIPAL SUBSIDIARIES. As long as any of the Notes remain
outstanding, the Company will not, and will not permit any Subsidiary to, issue, sell, assign, transfer or otherwise dispose of, directly or indirectly, any of the Common Stock of any Principal Subsidiary (except to the Company or to one or more
Subsidiaries or for the purpose of qualifying directors); provided, however, that this covenant shall not apply if (i) the issuance, sale, assignment, transfer or other disposition is required to comply with the order of a court
or regulatory authority of competent jurisdiction, other than an order issued at the request of the Company or of one of its Subsidiaries; (ii) the entire Common Stock of a Principal Subsidiary then owned by the Company or by its Subsidiaries
is disposed of in a single transaction or in a series of related transactions, for consideration consisting of cash or other property which is at least equal to the Fair Value of such Common Stock; or (iii) after giving effect to the issuance,
sale, assignment, transfer or other disposition, the Company and its Subsidiaries would own directly or indirectly at least 80% of the issued and outstanding Common Stock of such Principal Subsidiary and such issuance, sale, assignment, transfer or
other disposition is made for consideration consisting of cash or other property which is at least equal to the Fair Value of such Common Stock. 

Section 2.16. IMMEDIATELY AVAILABLE FUNDS. All payments of principal and interest shall be made in immediately available funds. 

  
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 ARTICLE III 

MISCELLANEOUS PROVISIONS 

Section 3.1. TRUSTEE NOT RESPONSIBLE FOR RECITALS. The recitals herein contained are made by the Company and not by the Trustee, and the
Trustee assumes no responsibility for the correctness thereof. The Trustee makes no representation as to the validity or sufficiency of this Ninth Supplemental Indenture. 

Section 3.2. PAYMENT OF EXPENSES UPON RESIGNATION OR REMOVAL. Upon termination of this Ninth Supplemental Indenture or the Indenture or
the removal or resignation of the Trustee, unless otherwise stated, the Company shall pay to the Trustee all amounts accrued to the date of such termination, removal or resignation. 

Section 3.3. ADOPTION, RATIFICATION AND CONFIRMATION. The Indenture, as supplemented and amended by this Ninth Supplemental Indenture, is
in all respects hereby adopted, ratified and confirmed. 
 Section 3.4. COUNTERPARTS. This Ninth Supplemental Indenture may be executed
in any number of counterparts, each of which shall be an original, but such counterparts shall together constitute but one and the same instrument. 

Section 3.5. GOVERNING LAW. THIS NINTH SUPPLEMENTAL INDENTURE AND EACH NOTE SHALL BE DEEMED TO BE A CONTRACT MADE UNDER THE LAWS OF THE
STATE OF NEW YORK AND SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAWS OF THE STATE OF NEW YORK WITHOUT REGARD TO CONFLICTS OF LAWS PRINCIPLES THEREOF. 

[SIGNATURE PAGE FOLLOWS] 

  
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 IN WITNESS WHEREOF, the parties hereto have caused this Ninth Supplemental Indenture to be duly
executed on the day and year first above written. 
  

			
	W. R. BERKLEY CORPORATION
		
	By:	 	/s/ Eugene G. Ballard
		 	Name: Eugene G. Ballard
		 	Title: Senior Vice President
	
	 THE BANK OF NEW YORK MELLON,
 as
Trustee

		
	By:	 	/s/ Francine Kincaid
		 	Name: Francine Kincaid
		 	Title: Vice President



  
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 EXHIBIT A 

(FORM OF FACE OF NOTE) 
 This
Note is a global Security within the meaning of the Indenture hereinafter referred to and is registered in the name of a Depository or a nominee of a Depository. This Note is exchangeable for Securities registered in the name of a person other than
the Depository or its nominee only in the limited circumstances described in the Indenture, and no transfer of this Note (other than a transfer of this Note as a whole by the Depository to a nominee of the Depository or by a nominee of the
Depository to the Depository or another nominee of the Depository) may be registered except in limited circumstances. 
 Unless this Note is
presented by an authorized representative of The Depository Trust Company (55 Water Street, New York, New York) to the issuer or its agent for registration of transfer, exchange or payment, and any Note issued is registered in the name of
Cede & Co. or such other name as requested by an authorized representative of The Depository Trust Company and any payment hereon is made to Cede & Co., ANY TRANSFER, PLEDGE OR OTHER USE HEREOF FOR VALUE OR OTHERWISE BY A PERSON IS
WRONGFUL since the registered owner hereof, Cede & Co., has an interest herein. 
  

			
	 Certificate No. —
	  	$—
	 Dated: August 6, 2014
	  	CUSIP No. 084423 AT9
		  	ISIN No. US084423AT91

 W. R. BERKLEY CORPORATION 

4.75% Senior Notes due 2044 
 W.
R. BERKLEY CORPORATION, a Delaware corporation (the “Company,” which term includes any successor corporation under the Indenture hereinafter referred to), for value received, hereby promises to pay to CEDE & CO. or registered
assigns, the principal sum of • DOLLARS AND NO CENTS ($•) on August 1, 2044. The Company further promises to pay interest on said principal sum outstanding from August 6, 2014, or from the most recent interest payment date
(each such date, an “Interest Payment Date”) to which interest has been paid or duly provided for, semiannually in arrears on February 1 and August 1 of each year commencing February 1, 2015 at the rate of 4.75% per
annum, until the principal hereof shall have become due and payable and, until the principal hereof is paid or duly provided for or made available for payment. The amount of interest payable on any Interest Payment Date shall be computed on the
basis of a 360-day year comprised of twelve 30-day months. The amount of interest payable for any partial period shall be computed on the basis of the number of actual days elapsed in a 360-day year of twelve 30-day months. In the event that any
date on which interest is payable on this Note is not a Business Day, then payment of interest payable on such date will be made on the next succeeding day that is a Business Day (and without any interest or other payment in respect of any such
delay). A “Business Day,” with respect to any Place of Payment or other location, shall mean any day other than a Saturday, Sunday or other day on which banking institutions in such Place of Payment or other location are authorized or
obligated by law, regulation or executive order to close. The interest installment so payable, and punctually paid or duly provided for, on any Interest Payment Date will, as provided in the Indenture, be paid to the Person in whose name this Note
(or one or more Predecessor Securities) is registered at the close of business on the January 15 or July 15 prior to such Interest Payment Date. Any such interest installment not punctually paid or duly provided for shall forthwith cease
to be payable to the registered Holder on such Regular Record Date and may either be paid to the Person in whose name this Note (or one or more Predecessor Securities) is registered at the close of business on a Special Record Date to be fixed by
the Trustee for the payment of such Defaulted Interest, notice whereof shall be given to the Holder of this Note not less than 10 days prior to such Special Record Date, or be paid at any time in any other lawful manner not inconsistent with
the requirements of any securities exchange on which this Note may be listed, and upon such notice as may be required by such exchange, all as more fully provided in the Indenture. 

The principal of (and premium, if any) and the interest on this Note shall be payable at the office or agency of the Company maintained
for that purpose in the United States in such coin or currency of the United States of America that at the time of payment is legal tender for payment of public and private debts; provided, however, that payment of interest may be made
at the option of the Company by check mailed to the registered Holder at such address as shall appear in the Security Register. Notwithstanding the foregoing, so long as the Holder of this Note is 


  
 A-1 








 
Cede & Co., the payment of the principal of (and premium, if any) and interest on this Note will be made at such place and to such account as may be designated by Cede & Co. All
payments of principal and interest hereunder shall be made in immediately available funds. 
 Reference is hereby made to the further
provisions of this Note set forth on the reverse hereof, which further provisions shall for all purposes have the same effect as if set forth at this place. 

Unless the certificate of authentication hereon has been executed by the Trustee referred to on the reverse hereof by manual signature, this
Note shall not be entitled to any benefit under the Indenture or be valid for any purpose. 
 IN WITNESS WHEREOF, the Company has caused
this instrument to be executed. 
  

			
	W. R. BERKLEY CORPORATION
		
	By:	 	 
		 	Name:
		 	Title:


 CERTIFICATE OF AUTHENTICATION 

This is one of the Securities of the series designated herein referred to in the within-mentioned Indenture. 

Dated: August 6, 2014 
  

			
	THE BANK OF NEW YORK MELLON,
	as Trustee
		
	By:	 	 
		 	Authorized Signatory


  
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 (FORM OF REVERSE OF NOTE) 

This Note is one of a duly authorized issue of securities of the Company, designated as its 4.75% Senior Notes due 2044 (herein referred to as
the “Securities”), issued under and pursuant to an Indenture, dated as of February 14, 2003, between the Company and The Bank of New York Mellon (formerly known as The Bank of New York), as Trustee (herein called the
“Trustee,” which term includes any successor trustee under the Indenture), as supplemented by the Ninth Supplemental Indenture dated as of August 6, 2014, between the Company and the Trustee (the Indenture as so supplemented, the
“Indenture”), to which Indenture and all indentures supplemental thereto reference is hereby made for a description of the rights, limitations of rights, obligations, duties and immunities thereunder of the Trustee, the Company and the
Holders of the Securities, and of the terms upon which the Securities are, and are to be, authenticated and delivered. 
 All terms used in
this Note that are defined in the Indenture shall have the meanings assigned to them in the Indenture. 
 The Company may redeem the
Securities at the Company’s option, in whole or in part, at any time and from time to time at a Redemption Price equal to the greater of (i) 100% of the principal amount of such Securities to be redeemed and (ii) an amount, as
determined by an Independent Investment Banker, equal to the sum of the present values of the remaining scheduled payments of principal of and interest thereon (not including any portion of such payments of interest accrued as of the Redemption
Date) discounted to the Redemption Date on a semiannual basis assuming a 360-day year consisting of twelve 30-day months) at the Adjusted Treasury Rate, plus 25 basis points, plus, in either of the above cases, accrued and unpaid interest thereon
to, but not including, the Redemption Date. 
 “Adjusted Treasury Rate” means, with respect to any Redemption Date: 

 

	 	•	 	the yield, under the heading which represents the average for the immediately preceding week, appearing in the most recently published statistical release designated “H.15(519)” published by the Board of
Governors of the Federal Reserve System (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 United States 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 (as defined below), yields for
the two published maturities most closely corresponding to the Comparable Treasury Issue shall be determined and the Adjusted Treasury Rate shall be interpolated or extrapolated from such yields on a straight line basis, rounding to the nearest
month; or 

  

	 	•	 	if such release (or any successor release) is not published during the week preceding the calculation date or does not contain such yields, the rate per annum equal to the semi-annual 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. 


The Adjusted Treasury Rate shall be calculated on the third Business Day preceding the Redemption Date. 

“Comparable Treasury Issue” means, with respect to any Redemption Date, the United States Treasury security selected by an
Independent Investment Banker as having a maturity comparable to the remaining term of the Securities 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 term of those Securities (“Remaining Life”). 
 “Comparable
Treasury Price” means, with respect to any Redemption Date, (i) the average of three Reference Treasury Dealer Quotations for such Redemption Date, after excluding the highest and lowest Reference Treasury Dealer Quotations, or
(ii) if the Independent Investment Banker obtains fewer than three such Reference Treasury Dealer Quotations, the average of all such quotations. 

“Independent Investment Banker” means, with respect to any Redemption Date, one of the Reference Treasury Dealers appointed by us.


  
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 “Reference Treasury Dealer” means, with respect to any Redemption Date: 

 

	 	•	 	each of J.P. Morgan Securities LLC, Morgan Stanley & Co. LLC, a Primary Treasury Dealer (as defined below) selected by Wells Fargo Securities, LLC (or any affiliate of any of the foregoing that is a Primary
Treasury Dealer), and their respective successors; provided that, if any of the foregoing ceases to be a primary U.S. Government securities dealer in the United States (a “Primary Treasury Dealer”), we will substitute another Primary
Treasury Dealer; and 

  

	 	•	 	any other Primary Treasury Dealer selected by the Company. 

 “Reference Treasury Dealer
Quotations” means, with respect to each Reference Treasury Dealer and any Redemption Date, the average, as determined by the Independent Investment Banker, 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 Independent Investment Banker at 5:00 p.m., New York City Time, on the third Business Day preceding such Redemption Date. 

The Company will mail a notice of redemption at least 30 days but not more than 60 days before the Redemption Date to each
holder of the Securities to be redeemed. If less than all of the Securities are to be redeemed, the Trustee will select in a fair and appropriate manner, including pro rata or by lot, the Securities to be redeemed in whole or in part;
provided that if the notes are represented by global notes and such global notes are held by The Depository Trust Company, beneficial interests in the notes will be selected for redemption by The Depository Trust Company in accordance with its
standard procedures therefor.  
 Unless the Company defaults in payment of the Redemption Price, on and after the Redemption Date,
interest will cease to accrue on the Securities or portions thereof called for redemption. 
 If an Event of Default with respect to
Securities of this series shall occur and be continuing, the principal of the Securities of this series may be declared due and payable in the manner, with the effect and subject to the conditions provided in the Indenture. 

The Indenture contains provisions for satisfaction, discharge and defeasance at any time of the entire indebtedness of this Note upon
compliance by the Company with certain conditions set forth in the Indenture. 
 The Indenture permits, with certain exceptions as therein
provided, the amendment thereof and the modification of the rights and obligations of the Company and the rights of the Holders of the Securities of each series to be affected under the Indenture at any time by the Company and the Trustee with the
consent of the Holders of a majority in principal amount of the Securities of each series at the time Outstanding of each series to be affected. The Indenture also contains provisions permitting Holders of specified percentages in principal amount
of the Securities of each series at the time Outstanding, on behalf of the Holders of all Securities of such series, to waive compliance by the Company with certain provisions of the Indenture and certain past defaults under the Indenture and their
consequences. Any such consent or waiver by the Holder of this Note shall be conclusive and binding upon such Holder and upon all future Holders of this Note and of any Note issued upon the registration of transfer hereof or in exchange herefor or
in lieu hereof, whether or not notation of such consent or waiver is made upon this Note. No reference herein to the Indenture and no provision of this Note or of the Indenture (other than Section 4.2 of the Indenture) shall alter or impair the
obligation of the Company to pay the principal and interest on the Note at the times, place and rate, and in the coin or currency, herein prescribed. 

As provided in the Indenture and subject to certain limitations therein set forth, the transfer of this Note is registrable in the Security
Register, upon surrender of this Note for registration of transfer at the office or agency of the Company maintained under Section 10.2 of the Indenture duly endorsed by, or accompanied by a written instrument of transfer, in form satisfactory
to the Company and the Security Registrar, duly executed by the Holder hereof or his or her attorney duly authorized in writing, and thereupon one or more new Securities of this series, of authorized denominations and for the same aggregate
principal amount, will be issued to the designated transferee or transferees. No service charge shall be made for any such registration of transfer or exchange, but the Company may require payment of a sum sufficient to cover any tax or other
governmental charge payable in connection therewith. 

  
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 Prior to due presentment of this Note for registration of transfer, the Company, the Trustee and
any agent of the Company or the Trustee may treat the Person in whose name this Note is registered as the owner hereof for all purposes, whether or not this Note be overdue, and neither the Company, the Trustee nor any such agent shall be affected
by notice to the contrary. 
 This global Note is exchangeable for Securities in definitive form only under certain limited circumstances
set forth in the Indenture. Securities of this series so issued are issuable only in registered form without coupons in denominations of $1,000 and any integral multiple thereof. As provided in the Indenture and subject to certain limitations herein
and therein set forth, Securities of this series so issued are exchangeable for a like aggregate principal amount of Securities of this series of a different authorized denomination, as requested by the Holder surrendering the same. 

The Company and, by its acceptance of this Note or a beneficial interest therein, the Holder of, and any Person that acquires a beneficial
interest in, this Note agree that for United States federal, state and local tax purposes it is intended that this Note constitute indebtedness. 

THE INTERNAL LAWS OF THE STATE OF NEW YORK SHALL GOVERN THE INDENTURE AND THE SECURITIES WITHOUT REGARD TO CONFLICT OF LAW PROVISIONS THEREOF.


  
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