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Exhibit 4(b)    
  

        Unless
this certificate is presented by an authorized representative of The Depository Trust Company, a New York corporation ("DTC"), to the Trust (as defined below) or its agent for
registration of transfer, exchange, or payment, and any certificate issued is registered in the name of Cede & Co. or in such other name as is requested by an authorized representative of DTC
(and any payment is made to Cede & Co. or to such other entity as is requested by an authorized representative of DTC), 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. 

	REGISTERED

No.: 1	 	PRINCIPAL AMOUNT: $60,000,000
	

CUSIP NUMBER: 939653 AD 3	
 	

 

WASHINGTON REAL ESTATE INVESTMENT TRUST

51/8% SENIOR NOTE DUE MARCH 15, 2013 

        WASHINGTON
REAL ESTATE INVESTMENT TRUST, a Maryland real estate investment trust (hereinafter called the "Trust," which term shall include any successor trust or corporation under the
Indenture hereinafter referred to), for value received, hereby promises to pay to Cede & Co., or registered assigns, upon presentation, the principal sum of SIXTY MILLION DOLLARS ($60,000,000)
on March 15, 2013, and to pay interest on the outstanding principal amount thereon from March 17, 2003, or from the most recent Interest Payment Date to which interest has been paid or
duly provided for, semi-annually in arrears on March 15 and September 15 in each year, commencing September 15, 2003, at the rate of 51/8% per annum,
until the entire principal amount hereof is paid or made available for payment. The interest 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 Notes) is registered at the close of business on the Regular Record Date for such interest which shall be 15
calendar days (whether or not a Business Day) next preceding such Interest
Payment Date. Any such interest not so punctually paid or duly provided for shall forthwith cease to be payable to the Holder on such Regular Record Date, and may either be paid to the Person in whose
name this Note (or one or more Predecessor Notes) is registered at the close of business on a Special Record Date for the payment of such Defaulted Interest to be fixed by the Trustee, notice whereof
shall be given to Holders of Notes of this series not more than 15 days and not less than 10 days prior to such Special Record Date, or may 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. Payment of the principal of, Make Whole Amount, if any, on, and interest on this Note will be made at the office or agency of the Trust maintained for that purpose in the City of New York,
State of New York, or elsewhere as provided in the Indenture, in such coin or currency of the United States of America as at the time of payment is legal tender for payment of public and private
debts; provided, however, that at the option of the Trust payment of interest may be made by (i) check mailed to the address of the Person entitled thereto as such address shall appear in the
Security Register kept for the Notes pursuant to Section 305 of the Indenture (the "Note Register") or (ii) transfer to an account of the Person entitled thereto located inside the
United States. 

        This
Note is one of a duly authorized issue of securities of the Trust (herein called the "Notes"), issued and to be issued in one or more series under an Indenture, dated as of
August 1, 1996 (herein called the "Indenture"), between the Trust and Bank One Trust Company, N.A. (formerly The First National Bank of Chicago) (herein called the "Trustee," which term
includes any successor trustee under the Indenture with respect to the Notes), to which Indenture and all indentures supplemental thereto reference is hereby made for a statement of the respective
rights, limitations of rights, duties and immunities thereunder of the Trust, the Trustee and the Holders of the Notes and of the terms upon which the Notes are, and are to be, authenticated and
delivered. This Note is one of the series 

 

designated as the "51/8% Senior Notes due March 15, 2013", limited in aggregate principal amount to $60,000,000. 

        The
Notes may be redeemed at any time at the option of the Trust, in whole or in part, upon notice of not more than 60 nor less than 30 days prior to the Redemption Date, at a
redemption price equal to the sum of (i) the principal amount of the Notes being redeemed plus accrued interest thereon to the Redemption Date and (ii) the Make-Whole Amount,
if any, with respect to such Notes. 

        The
following definitions apply with respect to any redemption or accelerated payment of the Notes: 

        "Make-Whole
Amount" means, in connection with any optional redemption or accelerated payment of any Notes, the excess, if any, of (a) the aggregate present value as of
the date of such redemption or
accelerated payment of each dollar of principal being redeemed or paid and the amount of interest (exclusive of interest accrued to the date of redemption or accelerated payment) that would have been
payable in respect of each such dollar if such redemption or accelerated payment had not been made, determined by discounting, on a semi-annual basis, such principal and interest at the
Reinvestment Rate (determined on the third Business Day preceding the date such notice of redemption is given or declaration of acceleration is made) from the respective dates on which such principal
and interest would have been payable if such redemption or accelerated payment had not been made, over (b) the aggregate principal amount of the Notes being redeemed or paid. 

        "Reinvestment
Rate" means 0.25% plus the arithmetic mean of the yields under the heading "Week Ending" published in the most recent Statistical Release under the caption "Treasury
Constant Maturities" for the maturity (rounded to the nearest month) corresponding to the remaining life to maturity of the Note, as of the payment date of the principal of the Notes being redeemed or
paid. If no maturity exactly corresponds to such maturity, yields for the two published maturities most closely corresponding to such maturity shall be calculated pursuant to the immediately preceding
sentence and the Reinvestment Rate shall be interpolated or extrapolated from such yields on a straight-line basis, rounding in each of such relevant periods to the nearest month. For the
purposes of calculating the Reinvestment Rate, the most recent Statistical Release published prior to the date of determination of the Make-Whole Amount shall be used. 

        "Statistical
Release" means the statistical release designated "H.15(519)" or any successor publication which is published weekly by the Federal Reserve System and which establishes
yields on actively traded United States government securities adjusted to constant maturities, or, if such statistical release is not published at the time of any determination of the
Make-Whole Amount, then such other reasonably comparable index which shall be designated by the Trust. 

        The
Indenture contains provisions for defeasance at any time of (a) the entire indebtedness of the Trust on this Note and (b) certain restrictive covenants and the related
defaults and Events of Default applicable to the Trust, in each case, upon compliance by the Trust with certain conditions set forth in the Indenture, which provisions apply to this Note. 

        If
an Event of Default with respect to the Notes of this series shall occur and be continuing, the principal of, and the Make-Whole Amount, if any, on, the Notes of this
series may be declared due and payable in the manner and with the effect provided in the Indenture. 

        As
provided in and subject to the provisions of the Indenture, the Holder of this Note shall not have the right to institute any proceeding with respect to the Indenture or for the
appointment of a receiver or trustee or for any other remedy thereunder, unless such Holder shall have previously given the Trustee written notice of a continuing Event of Default with respect to the
Notes of this series, the Holders of not less than 25% in principal amount of the Notes of this series at the time Outstanding shall have made written request to the Trustee to institute proceedings
in respect of such Event of 

2

 

Default as Trustee and offered the Trustee reasonable indemnity and the Trustee shall not have received from the Holders of a majority in principal amount of the Notes of this series at the time
Outstanding a direction inconsistent with such request, and shall have failed to institute any such proceeding, for 60 days after receipt of such notice, request and offer of indemnity. The
foregoing shall not apply to any suit instituted by the Holder of this Note for the enforcement of any payment of principal hereof or any interest on or after the respective due dates expressed
herein. 

        The
Indenture permits, with certain exceptions as therein provided, the amendment thereof and the modification of the rights and obligations of the Trust and the rights of the Holders of
the Notes under the Indenture at any time by the Trust and the Trustee with the consent of the Holders of not less than a majority in principal amount of the Outstanding Notes. The Indenture also
contains provisions permitting the Holders of specified percentages in principal amount of the Notes at the time Outstanding, on behalf of the Holders of all Notes, to waive compliance by the Trust
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 shall alter or impair the obligation of the Trust, which is absolute and unconditional, to pay the
principal of, Make-Whole Amount, if any, on, and interest on this 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 Note Register, upon surrender of this Note for
registration of transfer at the office or agency of the Trust in any Place of Payment where the principal of, Make-Whole Amount, if any, on, and interest on this Note are payable, duly
endorsed by, or accompanied by a written instrument of transfer in form satisfactory to the Trust and the Security Registrar for the Notes (the "Note Registrar") duly executed by, the Holder hereof or
his attorney duly authorized in writing, and thereupon one or more new Notes of this series, of authorized denominations and for the same aggregate principal amount, will be issued to the designated
transferee or transferees. 

        The
Notes of this series 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 therein set forth, Notes of this series are exchangeable for a like aggregate principal amount of Notes of this series of a different authorized denomination, as requested by the
Holder surrendering the same. 

        No
service charge shall be made for any such registration of transfer or exchange, but the Trust may require payment of a sum sufficient to cover any tax or other governmental charge
payable in connection therewith. 

        Prior
to due presentment of this Note for registration of transfer, the Trust, the Trustee and any agent of the Trust 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 Trust, the Trustee nor any such agent shall be affected by notice to the contrary. 

        The
obligations of the Trust under the Indenture and this Note and all documents delivered in the name of the Trust in connection herewith and therewith do not and shall not constitute
personal obligations of the trustees, officers, employees, agents or shareholders of the Trust or any of them, and shall not involve any claim against or personal liability on the part of any of them,
and all persons including the Trustee shall look solely to the assets of the Trust for the payment of any claim thereunder or for the performance thereof and shall not seek recourse against such
trustees, officers, 

3

 

employees, agents or shareholders of the Trust or any of them or any of their personal assets for such satisfaction. The performance of the obligations of the Trust under the Indenture and this Note
and all documents delivered in the name of the Trust in connection therewith shall not be deemed a waiver of any rights or powers of the Trust, trustees or shareholders under the Trust's Declaration
of Trust. 

        All
terms used in this Note which are defined in the Indenture shall have the meanings assigned to them in the Indenture. 

        THE
INDENTURE AND THE NOTES, INCLUDING THIS NOTE, SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAW OF THE STATE OF NEW YORK. 

        Pursuant
to a recommendation promulgated by the Committee on Uniform Security Identification Procedures, the Trust has caused "CUSIP" numbers to be printed on the Notes as a convenience
to the Holders of the Notes. No representation is made as to the correctness or accuracy of such CUSIP numbers as printed on the Notes, and reliance may be placed only on the other identification
numbers printed hereon. 

        Unless
the certificate of authentication hereon has been executed by or on behalf of the Trustee by manual signature, this Note shall not be entitled to any benefit under the Indenture
or be valid or obligatory for any purpose. 

        IN
WITNESS WHEREOF, the Trust has caused this instrument to be duly executed this March 17, 2003. 

	 	WASHINGTON REAL ESTATE INVESTMENT TRUST
	

 	

By:	
 	

 
	 	 	 	

	 	Name:	 	Edmund B. Cronin, Jr.
	 	Title:	 	Chairman, President and Chief Executive Officer

	Attest:	 	 
	

By:	

 	
 	

 
	 	
	 	 
	Name:	Laura M. Franklin	 	 
	Title:	Corporate Secretary	 	 

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TRUSTEE'S
CERTIFICATE OF AUTHENTICATION: 

        This
is one of the Notes of the series designated "51/8% Senior Notes due March 15, 2013" pursuant to the within-mentioned Indenture. 

	BANK ONE TRUST COMPANY, N.A.

as Trustee	 	 
	

By:	

 	
 	

 
	 	
	 	 
	Authorized Signatory

	 	 

5

 

ASSIGNMENT FORM 

FOR
VALUE RECEIVED, the undersigned hereby

sells, assigns and transfers unto 

PLEASE
INSERT SOCIAL

SECURITY OR OTHER IDENTIFYING
                                         
                                   

NUMBER OF ASSIGNEE 

                                        
                                          
                                         
                                          
                 

(Please Print or Typewrite Name and Address, including Zip Code, of Assignee) 

the
within Note of Washington Real Investment Trust and                          hereby does irrevocably constitute and appoint

                                        
                                          
                                         
                                          
                 

Attorney to transfer said Note on the books of the within-named Trust with full power of substitution in the premises. 

Dated:
                                         
                                   

Signature:
                                         
                                          
             

NOTICE: The signature to this assignment must correspond with the name as it appears on the first page of the within Note in every particular, without alteration or enlargement or any change whatever. 

Signature
Guaranteed:
                                         
                                   

NOTICE: Signatures) must be guaranteed by an "eligible guarantor institution" that is a member or participant in a "signature
guarantee program" (e.g., the Securities Transfer Agents Medallion Program, the Stock Exchange Medallion Program or the New York Stock Exchange, Inc. Medallion Signature
Program). 

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EXHIBIT 4.01  

  LEHMAN BROTHERS HOLDINGS INC.  

 AND  

 JPMORGAN CHASE BANK,  

 as Trustee

  

 FOURTH SUPPLEMENTAL INDENTURE  

 Dated as of March 17, 2003

 

 

        THIS FOURTH SUPPLEMENTAL INDENTURE, dated as of March 17, 2003, is between LEHMAN BROTHERS HOLDINGS INC., a corporation duly organized and existing under the laws of the
State of Delaware (the "Company"), and JPMORGAN CHASE BANK (formerly known as The Chase Manhattan Bank and prior thereto as Chemical Bank), a banking corporation duly organized and existing under the
laws of the State of New York, acting as Trustee under the Indenture referred to below (the "Trustee"). 

W I T N E S S E T H 

        WHEREAS,
the Company has duly authorized the execution and delivery of an Indenture dated as of February 1, 1996 (the "Indenture"), as amended and supplemented, to provide for the
issuance from time to time of its unsecured notes or other evidences of indebtedness to be issued in one or more series (the "Securities"), as in the Indenture provided, up to such principal amount or
amounts as may from time to time be authorized in or pursuant to one or more resolutions of the Board of Directors; 

        WHEREAS,
the Company will issue to Lehman Brothers Holdings Capital Trust III, a Delaware statutory trust ("Trust III"), a series of Securities entitled the "6.375% Subordinated
Deferrable Interest Debentures due 2052" (the "Subordinated Debentures"); 

        WHEREAS,
the Company has duly authorized the execution and delivery of this Fourth Supplemental Indenture in order to provide for certain supplements to the Indenture which shall only be
applicable to the Subordinated Debentures; 

        WHEREAS,
all acts and things necessary to make this Fourth Supplemental Indenture a valid agreement of the Company according to its terms have been done and performed, and the execution
and delivery of this Fourth Supplemental Indenture have in all respects been duly authorized; 

        NOW,
THEREFORE, in consideration of the premises, of the purchase and acceptance of the Securities by the Holders thereof, and of the sum of one dollar duly paid to it by the Trustee at
the execution and delivery of these presents, the receipt whereof is hereby acknowledged, the Company covenants and agrees with the Trustee to supplement the Indenture, only for purposes of the
Subordinated Debentures, as follows: 

        SECTION
1.    AMENDMENTS TO THE INDENTURE    

        1.1    Amendment to Section 101 of the Indenture.    Section 101 of the Indenture is hereby amended
solely with respect to the Subordinated Indentures by adding the following new definitions thereto, in the appropriate alphabetical sequence: 

"Debentures"
means the Company's 6.375% Subordinated Deferrable Interest Debentures due 2052. 

"Declaration"
means the Amended and Restated Declaration of Trust, dated as of March 17, 2003 among the Company and the trustees named therein. 

 

"Trust
III" means Lehman Brothers Holdings Capital Trust III, a Delaware statutory trust. 

        1.2    Amendment to Section 501 of the Indenture.    Section 501 is amended by deleting the "or" at the
end of paragraph (6) and inserting "; or" at the end of paragraph (7) in place of the period and adding the following at the end thereof: 

"(8)
Trust III shall have voluntarily or involuntarily dissolved, wound-up its business or otherwise terminated its existence except in connection with (i) distribution of the
Securities held by Trust III to holders of its securities in liquidation of such holders' interests in Trust III, (ii) redemption of all of the securities issued by Trust III, or
(iii) mergers, consolidations or amalgamations, each as permitted by Section 3.15 of the Declaration." 

        1.3    Amendment to Section 902 of the Indenture.    Section 902 is amended to add the following at the
end thereof: 

"For
purposes of this Section 902, if the Debentures are held by Trust III, the consent of not less than 66 2/3% of the aggregate liquidation amount of the securities issued by
Trust III shall be required in order for such supplemental indenture to be effective." 

        1.4    Amendment to Section 1007 of the Indenture.    Section 1007 is amended to add the following at
the end thereof: 

"For
purposes of this Section 1007, if the Debentures are held by Trust III, the consent of not less than a majority of the aggregate liquidation amount of the securities issued by Trust III
shall be required in order to waive a covenant." 

        1.5    Amendment to Section 513 of the Indenture.    Section 513 is amended to add the following at the
end thereof: 

"For
purposes of this Section 513, if the Debentures are held by Trust III, the consent of not less than a majority of the aggregate liquidation amount of the securities issued by Trust III
shall be required in order to waive such default." 

        1.6    Amendment to Article Ten of the Indenture.    Article Ten of the Indenture is amended to add the following
covenant at the end of such Article: 

        "SECTION
1010.    Trust Covenants.    

The
Company shall, for so long as Trust III is in existence: (i) maintain directly or indirectly 100% ownership of the common securities of Trust III, (ii) cause Trust III to remain a
statutory trust and not to be voluntarily dissolved, wound-up, liquidated or terminated, except as provided for in the Declaration, (iii) use its commercially reasonable efforts to
assure that Trust III will not be an "investment company" for purposes of the Investment Company Act of 1940, (iv) take no action that would be reasonably likely to cause Trust III to be
classified as an 

2

 

association in a publicly traded partnership taxable as a corporation for United States federal income tax purposes, and (v) agree to pay all debts and obligations (other than with respect to
the securities issued by Trust III) and all costs and expenses of Trust III (including, but not limited to, all costs and expenses relating to the organization of Trust III, the fees and
expenses of the trustees and all costs and expenses relating to the operation of Trust III) and to pay any and all taxes, duties, assessments or governmental charges of whatever nature (other
than withholding taxes) imposed on Trust III by the United States, or any other taxing authority, so that the net amounts received and retained by Trust III
after paying such expenses will be equal to the amounts Trust III would have received had no such costs or expenses been incurred by or imposed on the Trust III. The foregoing obligations of the
Company are for the benefit of, and shall be enforceable by, any Person to whom any such debts, obligations, costs, expenses and taxes are owed (each, a "Creditor") whether or not such Creditor has
received notice thereof. Any such Creditor may enforce such obligations of the Company directly against the Company, and the Company irrevocable waives any right or remedy to require that any such
Creditor take any action against Trust III or any other Person before proceeding against the Company. 

        SECTION 2.    MISCELLANEOUS    

        2.1    Debentures.    Attached hereto as Exhibit A is a form of the Subordinated Debenture. 

        2.2    Separability.    In case any provision in this Fourth Supplemental Indenture shall be invalid, illegal or
unenforceable, the validity, legality and enforceability of the remaining provisions shall not in any way be affected or impaired thereby. 

        2.3    Continuance of Indenture.    This Fourth Supplemental Indenture supplements the Indenture and shall be a part
of and subject to all the terms thereof. The Indenture, as supplemented by this Fourth Supplemental Indenture, shall continue in full force and effect. 

        2.4    The Trustee.    The Trustee shall not be responsible in any manner for or in respect of the validity or
sufficiency of this Fourth Supplemental Indenture, or for or in respect of the recitals contained herein, all of which recitals are made by the Company solely. 

        2.5    Governing Law.    This Fourth Supplemental Indenture shall be governed by and construed in accordance with the
laws of the State of New York. 

        2.6    Defined Terms.    All capitalized terms used in this Fourth Supplemental Indenture which are defined in the
Indenture, but not otherwise defined herein, shall have the same meanings assigned to them in the Indenture. 

        2.7    Counterparts.    This Fourth 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. 

3

 

        JPMorgan
Chase Bank hereby accepts the trusts in this Fourth Supplemental Indenture declared and provided, upon the terms and conditions hereinabove set forth. 

4

 

        IN
WITNESS WHEREOF, Lehman Brothers Holdings Inc. has caused this Fourth Supplemental Indenture to be signed and acknowledged by its President, its Chairman of the Board, one of
its Vice Presidents, its Chief Executive Officer or its Treasurer, and JPMorgan Chase Bank, as Trustee, has caused this Fourth Supplemental Indenture to be signed and acknowledged by one its
authorized officers, and its corporate seal to be affixed hereunto, and the same to be attested by one of its authorized officers, as of the day and year first above written. 

	 	 	LEHMAN BROTHERS HOLDINGS INC.
	 	 	 	 
	 	 	 	 
	 	 	By:	/s/  OLIVER BUDDE      
 Name: Oliver Budde

Title: Vice President
	 	 	 	 
	 	 	 	 
	 	 	JPMORGAN CHASE BANK, as Trustee
	 	 	 	 
	 	 	 	 
	 	 	By:	/s/  ENRICO D. REYES      
 Authorized Officer

5

EXHIBIT A  

	No. D-            	 	$                        	 	 

 
 

LEHMAN BROTHERS HOLDINGS INC.    
    
    6.375% SUBORDINATED DEFERRABLE INTEREST DEBENTURE DUE 2052    
  

        Lehman Brothers Holdings Inc., a corporation duly organized and existing under the laws of the State of Delaware (herein referred to as the "Company"), for
value received, hereby promises to pay to JPMORGAN CHASE BANK, as Property Trustee (the "Property Trustee") for LEHMAN BROTHERS HOLDINGS CAPITAL TRUST III (the "Trust"), at the office or agency of the
Company in the Borough of Manhattan, the City of New York, the principal sum of                        dollars on March 15,
2052, in such coin or currency of the United States of America as at the
time of payment shall be legal tender for the payment of public and private debts, and to pay interest on said principal sum at said office or agency, in like coin or currency, at the rate per annum
specified in the title of this Debenture until the principal hereof becomes due and payable, and on any overdue principal and (to the extent that payment of such interest is enforceable under
applicable law) on any overdue installment of interest at the same rate per annum during the period in which such principal is overdue, compounded quarterly, to the registered holder of this
Debenture, until payment of said principal sum has been made or duly provided for. Interest on this Debenture, (computed as set forth herein) shall be payable quarterly (subject to deferral as set
forth herein) in arrears on March 15, June 15, September 15 and December 15 of each year (each an "Interest Payment Date"), commencing June 15, 2003, from the date
of this Debenture or the most recent Interest Payment Date to which interest has been paid or duly provided for, unless the date hereof is a date to which interest has been paid or duly provided for. 

        The
interest so payable on any Interest Payment Date will, subject to certain exceptions provided in the Indenture referred to on the reverse hereof, be paid to the person in whose name
this Debenture (or one or more Predecessor Securities, as defined in said Indenture) is registered at the close of business on the Business Day prior to the relevant Interest Payment Date (each a
"Regular Record Date"). Interest may, at the option of the Company, be paid by check mailed to the person entitled thereto at such person's address as it appears in the registry books of the Company. 

        REFERENCE
IS MADE TO THE FURTHER PROVISIONS OF THIS DEBENTURE SET FORTH ON THE REVERSE HEREOF. SUCH FURTHER PROVISIONS SHALL FOR ALL PURPOSES HAVE THE SAME EFFECT AS THOUGH FULLY SET
FORTH AT THIS PLACE. 

        This
Debenture shall not be valid or become obligatory for any purpose until the certificate of authentication hereon shall have been signed by the Trustee under the Indenture referred
to on the reverse hereof. 

 

        IN
WITNESS WHEREOF, LEHMAN BROTHERS HOLDINGS INC. has caused this instrument to be signed by its Chairman of the Board, its Vice Chairman, its President, its Chief Financial
Officer, one of its Vice Presidents or its Treasurer by manual or facsimile signature, attested by its Secretary or one of its Assistant Secretaries by manual or facsimile signature. 

	 	 	LEHMAN BROTHERS HOLDINGS INC.
	 	 	 	 
	 	 	 	 
	 	 	By:	 
	 	 	 	
 Name: Oliver Budde

Title: Vice President

	Attest:	 	 
	 	 	 	 	 
	 	 	 	 	 
	
 Name: Cindy Gregoire

Title: Assistant Secretary	 	 	 	 

2

 
 
 

TRUSTEE'S CERTIFICATE OF AUTHENTICATION    
  

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

	Dated                             , 200  ,	 	 	 
	 	 	 	 
	 	 	JPMORGAN CHASE BANK,

as Trustee
	 	 	 	 
	 	 	 	 
	 	 	By:	 
	 	 	 	
 Authorized Officer

3

(Reverse of Debenture) 

 
 

LEHMAN BROTHERS HOLDINGS INC.
  6.375% SUBORDINATED DEFERRABLE INTEREST DEBENTURE DUE 2052    
  

        This Debenture is one of a duly authorized series of Debentures of the Company designated as the 6.375% Subordinated Deferrable Interest Debentures due 2052 of
the Company (herein called the "Debentures"). The Debentures are one of an indefinite number of series of debt securities of the Company (herein collectively called the "Securities"), issued or
issuable under and pursuant to an indenture, dated as of February 1, 1996, as amended and supplemented (herein called the "Indenture"), between the Company and JPMorgan Chase Bank, formerly
known as The Chase Manhattan Bank and prior thereto as Chemical Bank, as Trustee (herein called the "Trustee"), to which Indenture and all indentures supplemental thereto reference is hereby made for
a description of rights, limitations of rights, obligations, duties and immunities thereunder of the Trustee, the Company and the holders of the Debentures. The separate series of Securities may be
issued in various aggregate principal amounts, may mature at different times, may bear interest (if any) at different rates, may be subject to different redemption provisions or repayment or
repurchase rights (if any), may be subject to different sinking, purchase or analogous funds (if any), may be subject to different covenants and Events of Default, as defined in the Indenture, and may
otherwise vary as provided in the Indenture. 

        Payment
of the principal of and interest on this Debenture is, to the extent provided in the Indenture, subordinated and subject in right of payment to the prior payment in full when due
of the principal of (and premium, if any) and interest, if any, on all Senior Debt, as defined in the Indenture, of the Company and this Debenture is issued subject to the provisions of the Indenture
with respect thereto. Each registered holder of this Debenture, by accepting the same, (a) agrees to and shall be bound by such provisions, (b) authorizes and expressly directs the
Trustee on his or her behalf to take such action as may be necessary or appropriate to effectuate the subordination so provided and (c) appoints the Trustee as his or her
attorney-in-fact for any and all such purposes. Each registered holder hereof, by his or her acceptance hereof, hereby waives all notice of the acceptance of the subordination
provisions contained herein and in the Indenture by each holder of Senior Debt, whether now outstanding or hereafter incurred, and waives reliance by each such holder upon said provisions. Each
registered holder thereof, by his or her acceptance hereof, agrees to treat the Debentures as indebtedness for all United States federal income tax purposes. 

        Subject
to Article Eleven of the Indenture, at any time on or after March 15, 2008 and prior to maturity, the Company shall have the right to redeem this Debenture at the option
of the Company, in whole or in part, at 100% of the principal amount of such Debentures, plus any accrued but unpaid interest, to the Redemption Date. 

        If
an Investment Company Event (as defined in the Amended and Restated Declaration of Trust of the Trust, dated March 17, 2003 among the Company, as Sponsor, the Trust, and the
trustees of the Trust named thereto (the "Declaration") shall occur and be continuing, the Company may, at any time within 90 days following the occurrence of such Investment 

 

Company Event, redeem the Debentures, in whole but not in part, at a Redemption Price equal to 100% of the principal amount thereof, plus accrued and unpaid interest thereon to the Redemption Date.
Subject to certain conditions described in the Indenture, in the event of the occurrence and continuation of a Tax Event (as defined in the Declaration), in certain circumstances the Company may
redeem the Debentures, in whole but not in part, at any time within 90 days following the occurrence of a Tax Event at a Redemption Price equal to 100% of the aggregate principal amount
thereof, plus accrued and unpaid interest thereon to the Redemption Date. Any redemption pursuant to this paragraph shall be made upon not less than 30 nor more than 60 days' notice to the
Trustee and Holders of the Debentures. If less than all the Debentures are to be redeemed by the Company, the Debentures to be redeemed will be selected by lot or by such other method as the Trustee
shall deem fair and appropriate. The Debentures are not subject to a sinking fund. 

        In
the event of redemption of this Debenture in part only, a new Debenture or Debentures of this series for the unredeemed portion hereof will be issued in the name of the registered
holder hereof upon the surrender hereof at a Place of Payment (as defined in the Indenture). 

        In
case an Event of Default with respect to the Debentures shall have occurred and be continuing, the principal hereof may be declared, and upon such declaration shall become, due and
payable, in the manner, with the effect and subject to the conditions provided in the Indenture. The omission by the Company to pay interest during an Extension Period (as defined below) as permitted
hereby shall not constitute an Event of Default under Section 501 of the Indenture. An "Event of Default" means any of those events set forth in Section 501 of the Indenture, and the
event that, when the Property Trustee is the Holder of the Debentures, the Trust shall have voluntarily or involuntarily dissolved, wound-up its business or otherwise terminated its
existence except in connection with the (i) distribution of Debentures to holders of Preferred Securities and Common Securities in liquidation of their interests in the Trust, (ii) the
redemption of all of the outstanding Preferred Securities and Common Securities, or (iii) certain mergers, consolidations or amalgamation, each as permitted by the Declaration. 

        If
the Debentures are held by the Trust, the Company, as borrower, hereby covenants to pay all debts and obligations (other than with respect to the Preferred Securities and Common
Securities of the Trust) and all costs and expenses of the Trust (including, but not limited to, all costs and expenses relating to the organization of the Trust, the fees and expenses of the trustees
of the Trust and all costs
and expenses relating to the operation of the Trust) and to pay any and all taxes, duties, assessments or governmental charges of whatever nature (other than United States withholding taxes) imposed
on the Trust by the United States, or any other taxing authority, so that the net amounts received and retained by the Trust and the Property Trustee after paying such debts, obligations, costs,
expenses, taxes, duties, assessments, or other governmental charges, will be equal to the amounts the Trust and the Property Trustee would have received had no such debts, obligations, costs,
expenses, taxes, duties, assessments, or other governmental charges been incurred by or imposed on the Trust. The foregoing obligations of the Company are for the benefit of, and shall be enforceable
by, any person to whom any such debts, obligations, costs, expenses and taxes are owed (each, a "Creditor") whether or not such Creditor has received notice thereof. Any such Creditor may enforce such
obligations of the Company directly against the Company, and the Company irrevocably waives any right or 

2

 

remedy to require that any such Creditor take any action against the Trust or any other person before proceeding against the Company. The Company shall execute such additional agreements as may be
necessary or desirable to give full effect to the foregoing. 

        The
Company hereby covenants that, so long as any Preferred Securities and Common Securities of the Trust remain outstanding, if (i) there shall have occurred any Event of Default
under the Indenture with respect to the Debentures, (ii) the Company shall be in default with respect to its payment of any obligations under its Guarantee (as defined in the Declaration) with
respect to the Trust or (iii) the Company shall have given notice of its election of an Extension Period as provided herein and shall not have rescinded such notice, or such Extension Period or
any extension thereof shall be continuing, then the Company will not, and will not permit any Subsidiary to, (x) declare or pay any dividends or distributions on, or redeem, purchase, acquire
or make a liquidation payment with respect to, any of the Company's capital stock or (y) make any payment of principal, interest or premium, if any, on or repay, repurchase or redeem any debt
securities of the Company that rank on a parity with or junior in interest to this Debenture or make any guarantee payments with respect to any guarantee by the Company of the debt securities of any
Subsidiary of the Company if such guarantee ranks on a parity with or junior in interest to this Debenture (other than (a) dividends or distributions in common stock of the Company,
(b) payments under the Guarantee made by the Company in respect of the Preferred Securities and Common Securities of the Trust, (c) any declaration of a dividend in connection with the
implementation of a shareholders' rights plan, or the issuance of stock under any such plan in the future, or the redemption or repurchase of any such rights pursuant thereto, and (d) purchases
of common stock related to the issuance of common stock or rights under any of the Company's benefit plans). 

        The
Indenture contains provisions permitting the Company and the Trustee, with the consent of the holders of not less than 662/3% in aggregate principal amount of each
series of the Securities at the time Outstanding to be affected (each series voting as a class), evidenced as provided in the Indenture, to execute supplemental indentures adding any provisions to, or
changing in any manner or eliminating any of the provisions of the Indenture or of any supplemental indenture or modifying in any manner the rights of the holders of the Securities of all such series;  provided,
however, that no such supplemental indenture shall, among other things, (i) change the fixed maturity of any Security, or reduce the
principal amount thereof, or reduce the rate or extend the time of payment of interest thereon or reduce any premium payable on redemption, or make the principal thereof, or premium, if any, or
interest thereon payable in any coin or currency other than that hereinabove provided, or amend the Indenture to modify its provisions relating to the subordination of each Security in a
manner adverse to the holder thereof, without the consent of the holder of each Security so affected, or (ii) change the place of payment on any Security, or impair the right to institute suit
for payment on any Security, or reduce the aforesaid percentage of Securities, the holders of which are required to consent to any such supplemental indenture, without the consent of the holders of
each Security so affected. It is also provided in the Indenture that, prior to any declaration accelerating the maturity of any series of Securities, the holders of a majority in aggregate principal
amount of the Securities of such series Outstanding may on behalf of the holders of all the Securities of such series waive any past default or Event of Default under the Indenture with respect to
such series and its consequences, except a default in the payment of interest, if any, on or the principal of, or 

3

 

premium, if any, on any of the Securities of such series. Any such consent or waiver by the holder of this Debenture shall be conclusive and binding upon such holder and upon all future holders and
owners of this Debenture and any Debentures which may be issued in exchange or substitution herefor, irrespective of whether or not any notation thereof is made upon this Debenture or such other
Debentures. 

        No
reference herein to the Indenture and no provisions of this Debenture or of the Indenture shall alter or impair the obligations of the Company, which is absolute and unconditional, to
pay the principal of this Debenture at the place, at the time and in the coin or currency herein prescribed. 

        The
amount of interest payable for any period will be computed (i) for any full 180-day semi-annual interest payment period, on the basis of a
360-day year of twelve 30-day months, (ii) for any period shorter than a full 180-day semi-annual interest payment period for which interest
payments are computed, on the basis of a 30-day month and (iii) for periods of less than a month, the actual number of days elapsed per 30-day month. In the event that
any date on which interest is payable on this Debenture is not a Business Day (as defined in the Indenture), then payment of the amount payable on such date will be made on the next succeeding day
which is a Business Day (and without any interest or other payment in respect of any such delay) except that, if such Business Day is in the next succeeding calendar year, such payment shall be made
on the immediately preceding Business Day, in each case with the same force and effect as if made on the original Interest Payment Date, subject to certain rights of deferral described below. 

        The
Company shall have the right at any time, on one or more occasions, so long as an Event of Default has not occurred and is not continuing under the Indenture, to extend any interest
payment period on this Debenture for a period (an "Extension Period") not to exceed twenty consecutive quarterly interest payment periods; provided that the date on which such Extension Period ends
must be on an Interest Payment Date and must be no later than March 15, 2052 or any date on which any Debentures are fixed for redemption, and, as a consequence, the quarterly interest payment
on the Debentures would be deferred (but would continue to accrue with interest thereon compounded quarterly at the rate of interest on the Debentures, except to the extent payment of such interest is
prohibited by law) during any such Extension Period. On the Interest Payment Date at the end of each Extension Period, the Company shall pay all interest then accrued and unpaid (compounded quarterly,
at the rate of interest on the Debentures, except to the extent payment of such interest is prohibited by law) to the date of payment, to the persons in whose name the Debentures are registered on the
Regular Record Date immediately preceding the Interest Payment Date at the end of such Extension
Period. The Company shall give written notice to the Regular Trustees (as defined in the Declaration), the Property Trustee and the Trustee of its election of such Extension Period one Business Day
before the earlier of (i) the next succeeding date on which distributions on the Preferred Securities of the Trust are payable or (ii) the date the Trust is required to give notice of
the record date or the date such distributions are payable to the New York Stock Exchange or other applicable self-regulatory organization or to holders of the Preferred Securities issued
by the Trust, but in any event at least one Business Day before such record date. During any Extension Period, the Company may continue to extend the interest payment period by extending the Extension
Period, on one or more occasions 

4

 

by giving notice as aforesaid; provided that such Extension Period, as extended, must end on an Interest Payment Date and in no event shall the aggregate Extension Period, as extended, exceed twenty
consecutive quarterly interest payment periods or extend beyond March 15, 2052 or any date on which any of the Debentures are fixed for redemption. No interest shall be due and payable on the
Debentures during an Extension Period except at the end thereof. 

        Notwithstanding
the provisions of Section 401(a)(B) of the Indenture, the Company may satisfy and discharge the entire indebtedness on all the Debentures as provided therein only
when the Debentures are by their terms due and payable within one year. 

        The
Debentures are issuable in registered form without coupons in denominations of $25 and any multiple of $25. At the option of the holders thereof, either at the office or agency to be
designated and maintained by the Company for such purpose in the Borough of Manhattan, The City of New York, pursuant to the provisions of the Indenture or at any of such other offices or agencies as
may be designated and maintained by the Company for such purpose pursuant to the provisions of the Indenture, and in the manner and subject to the limitations provided in the Indenture, but without
the payment of any service charge, except for any tax or other governmental charges imposed in connection therewith, Debentures may be exchanged for an equal aggregate principal amount of Debentures
of like tenor and of other authorized denominations. 

        The
Company, the Trustee, and any agent of the Company or of the Trustee may deem and treat the registered holder hereof as the absolute owner of this Debenture (whether or not this
Debenture shall be overdue and notwithstanding any notation of ownership or other writing hereon), for the purpose of receiving payment hereof, or on account hereof, and for all other purposes, and
neither the Company nor the Trustee nor any agent of the Company or of the Trustee shall be affected by any notice to the contrary. All such payments made to or upon the order of such registered
holder shall, to the extent of the sum or sums paid, effectually satisfy and discharge liability for moneys payable on this Debenture. 

        No
recourse for the payment of the principal of or the interest on this Debenture, or for any claim based hereon or otherwise in respect hereof, and no recourse under or upon any
obligation, covenant or agreement of the Company in the Indenture or any indenture supplemental thereto or in any Debenture, or because of the creation of any indebtedness represented thereby, shall
be had against any incorporator, stockholder, officer or director as such, past, present or future, of the Company or of any successor corporation, either directly or through the Company or any
successor corporation,
whether by virtue of any constitution, statute or rule of law or by the enforcement of any assessment or penalty or otherwise, all such liability being, by the acceptance hereof and as part of the
consideration for the issue hereof, expressly waived and released. 

        As
provided in the Indenture and subject to certain limitations therein set forth, the transfer of this Debenture is registrable in the Security Register, upon surrender of this
Debenture for registration of transfer at the office or agency of the Company in any place where the principal of this Debenture is payable, duly endorsed by, or accompanied by a written instrument of
transfer in form satisfactory to the Company and the Security Registrar duly 

5

 

executed by, the holder hereof or such holder's attorney duly authorized in writing, and thereupon one or more new Debentures of this series of like tenor and of authorized denominations and for the
same aggregate principal amount will be issued to the designated transferee or transferees. 

        The Indenture and the Debentures shall be governed by and construed in accordance with the laws of the State of New York.

        All
items used in this Debenture which are defined in the Indenture shall have the meanings assigned to them in the Indenture. 

6

 

        The
following abbreviations, when used in the inscription on the face of the within Debenture, shall be construed as though they were written out in full according to applicable laws or
regulations: 

TEN
COM—as tenants in common

TEN ENT—as tenants by their entireties

JT TEN—as joint tenants with right of survivorship and not as tenants in common 

UNIF
GIFT MIN ACT—                         Custodian
                         under Uniform Gifts to

                                         
       (Cut)                                (Minor)
 

Minors
Act                        

                        (State) 

Additional
abbreviations may also be used though not in the above list. 

7

 
 

ASSIGNMENT    
  

        FOR VALUE RECEIVED, the undersigned hereby sells, assigns and transfers unto 

	

  

	    

	    

	    

	    

	    
 (Please insert social security or other identifying number of Assignee)
	

    
	    

	    

	    

	    
 (Name and address of Assignee, including zip code, must be printed or typewritten.)
	

the within Debenture, and all rights thereunder, hereby irrevocably constituting and appointing
	

    
	    

	    
 to transfer the said Debenture on the books of the Company, with full power of substitution in the premises.

	Date:	 	 	 	 	 
	 	 	
	 	 	 
	

 	
 	

 	
 	

Signature:	

 
	 	 	 	 	 	

	 	 	 	 	NOTICE: The signature to this assignment must correspond with the name as it appears upon the face of the within Debenture in every particular, without alteration or enlargement or any change whatever.

	Signature(s) Guaranteed:	 	 
	 	
	 
	THE SIGNATURE(S) SHOULD BE GUARANTEED BY AN ELIGIBLE GUARANTOR INSTITUTION (BANKS, STOCKBROKERS, SAVINGS AND LOAN ASSOCIATIONS AND CREDIT UNIONS WITH MEMBERSHIP IN AN APPROVED MEDALLION SIGNATURE GUARANTEE
PROGRAM), PURSUANT TO S.E.C. RULE 17Ad-15.

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LEHMAN BROTHERS HOLDINGS INC. 6.375% SUBORDINATED DEFERRABLE INTEREST DEBENTURE DUE 2052

TRUSTEE'S CERTIFICATE OF AUTHENTICATION

LEHMAN BROTHERS HOLDINGS INC. 6.375% SUBORDINATED DEFERRABLE INTEREST DEBENTURE DUE 2052

ASSIGNMENT

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