Exhibit 4.02


 


	
   No. D-1

   	
   $231,958,765

   



 


 


LEHMAN BROTHERS HOLDINGS INC.


6.24% SUBORDINATED DEFERRABLE INTEREST DEBENTURE DUE 2054


 


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, N.A., as
Property Trustee (the “Property Trustee”) for LEHMAN BROTHERS HOLDINGS CAPITAL
TRUST VI (the “Trust”), at the office or agency of the Company in the Borough of
Manhattan, the City of New York, the principal sum of TWO HUNDRED THIRTY ONE
MILLION NINE HUNDRED FIFTY EIGHT THOUSAND SEVEN HUNDRED SIXTY FIVE dollars on
January 18, 2054, 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 January 18, April 18, July 18 and October 18 of each year
(each an “Interest Payment Date”), commencing April 18, 2005, 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:

  	
  /s/ Barrett S. DiPaolo

  	
   

  
	
   

  	
   

  	
  Name:

  	
  Barrett S. DiPaolo

  
	
   

  	
   

  	
  Title:

  	
  Vice President

  
	
   

  	
   

  
	
   

  	
   

  
	
  Attest:

  	
   

  
	
   

  	
   

  
	
   

  	
   

  
	
  /s/ Anna Walters

  	
   

  	
   

  
	
  Name:

  	
  Anna Walters

  	
   

  
	
  Title:

  	
  Assistant Secretary

  	
   

  
							



 


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TRUSTEE’S CERTIFICATE OF AUTHENTICATION


 


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


 


	
  Dated January 18, 2005,

  	
   

  
	
   

  	
   

  
	
   

  	
  JPMORGAN CHASE BANK, N.A.,

  as Trustee

  
	
   

  	
   

  
	
   

  	
   

  
	
   

  	
  By:

  	
  /s/ Tai B. Lee

  	
   

  
	
   

  	
   

  	
  Authorized Officer

  



 


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(Reverse of Debenture)


 


LEHMAN BROTHERS HOLDINGS INC.


6.24% SUBORDINATED DEFERRABLE INTEREST DEBENTURE DUE 2054


 


This Debenture
is one of a duly authorized series of Debentures of the Company designated as
the 6.24% Subordinated Deferrable Interest Debentures due 2054 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, N.A. (as successor to The Chase Manhattan Bank (formerly known 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
January 18, 2010 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 January 18, 2005 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 


 


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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 66-2/3% 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 


 


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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 90-day quarterly interest payment period, on the basis of a 360-day
year of twelve 30-day months, (ii) for any period shorter than a full 90-day
quarterly 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 January 18,
2054 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 by giving
notice as aforesaid; provided that such 


 


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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 January 18, 2054 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 Company may omit to comply with any term, provision or condition
set forth in Section 801 of the Indenture, and any such omission with respect
to such Section shall not be an Event of Default, in each case with respect to
the Debentures, provided that the conditions of Section 1009 of the Indenture
have been satisfied.


 


The covenant set forth in Section 1005 of the Indenture shall not apply
to the Debentures.


 


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 


 


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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
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.


 


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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.


 


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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.