EX-4.21






Exhibit 4.21




SECOND SUPPLEMENTAL INDENTURE




     This Second Supplemental Indenture, dated as of February 6, 2009 (this “Second
Supplemental Indenture”), is entered into by and among (i) Reynolds American Inc., a North
Carolina corporation (the “Company”), as Issuer; (ii) Santa Fe Natural Tobacco Company,
Inc., a New Mexico corporation (“Santa Fe”), Lane, Limited, a New York corporation
(“Lane”), R. J. Reynolds Tobacco Company, a North Carolina corporation (“RJRT”), R.
J. Reynolds Tobacco Co., a Delaware corporation (“RJR Tobacco”), Reynolds Innovations Inc.
(f/k/a GMB, Inc.), a North Carolina corporation (“Innovations”), Reynolds Finance Company
(f/ka FHS, Inc.), a Delaware corporation (“RFC”), Conwood Holdings, Inc., a Delaware
corporation (“Conwood”), Conwood Company, LLC, a Delaware limited liability company
(“Conwood Company”), Rosswil LLC, a Delaware limited liability company (“Rosswil”),
R.J. Reynolds Tobacco Holdings, Inc., a Delaware corporation (“RJR”), R. J. Reynolds Global
Products, Inc., a Delaware corporation (“GPI”), and RAI Services Company, a North Carolina
corporation (“Services”), each as a Guarantor; and (iii) The Bank of New York Mellon Trust
Company, N.A. (f/k/a The Bank of New York Trust Company, N.A.), as Trustee under the Indenture
referred to below (the “Trustee”).



WITNESSETH:




     WHEREAS, Santa Fe, Lane, RJRT, RJR Tobacco, Innovations, RFC, Conwood, Conwood Company,
Rosswil, RJR, GPI (collectively, the “Existing Guarantors”), the Company and the Trustee
have heretofore executed and delivered an Indenture, dated as of May 31, 2006, as supplemented by
the First Supplemental Indenture dated as of September 30, 2006 thereto (as amended, supplemented,
waived or otherwise modified, the “Indenture”), providing for the issuance thereunder from
time to time of the Company’s debentures, notes or other evidence of indebtedness to be issued in
one or more series (the “Securities”);



     WHEREAS, Section 10.5 of the Indenture provides that the Company is required to
execute and deliver, and to cause each Subsidiary other than RJR (whether previously existing or
created or acquired by the Company) which becomes a Bank Credit Agreement Guarantor to execute and
deliver, to the Trustee a supplemental indenture pursuant to which such Subsidiary will
unconditionally guarantee, on a joint and several basis with the other Guarantors, the full and
prompt payment of the principal of, premium, if any, and interest on the Securities on an unsecured
and unsubordinated basis and become a party to the Indenture as a Guarantor for all purposes of the
Indenture;



     WHEREAS, Services has become a Bank Credit Agreement Guarantor;



     WHEREAS, Services, a subsidiary of the Company, has determined that it is desirable and would
be a direct benefit to Services for it, along with the Company and the Existing Guarantors, to
execute and deliver to the Trustee a supplemental indenture pursuant to which Services will
unconditionally guarantee, on a joint and several basis with the Existing Guarantors, the full and
prompt payment when due, whether at maturity, by acceleration, by redemption, by repurchase, or
otherwise, of the principal of, premium, if any, and interest, on the Securities and all other



 









 




Obligations of the Company to the Trustee and to the Securityholders under the Indenture, and
become a party to the Indenture as a Guarantor;




     WHEREAS, pursuant to Section 9.1 of the Indenture, the Company, the Existing
Guarantors, Services and the Trustee are authorized or permitted to execute and deliver this Second
Supplemental Indenture to amend the Indenture, without the consent of any of the Securityholders;
and



     WHEREAS, the Company, the Existing Guarantors and Services have duly authorized the execution
and delivery of this Second Supplemental Indenture.



     NOW, THEREFORE, in consideration of the foregoing and for other good and valuable
consideration, the receipt and sufficiency of which is hereby acknowledged, the parties hereto
mutually covenant and agree for the equal and ratable benefit of the holders of the Securities as
follows:



ARTICLE I




Definitions




     SECTION 1.1 Defined Terms. Unless otherwise indicated, capitalized terms used herein
but not otherwise defined herein shall have the respective meanings set forth in the Indenture.



ARTICLE II




Agreement to be Bound; Guarantee




     SECTION 2.1 Agreement to be Bound. Services hereby becomes a party to the Indenture
as a Guarantor, and will have all of the rights and be subject to all of the obligations and
agreements of a Guarantor under the Indenture. Services agrees to be bound by all of the
provisions of the Indenture applicable to a Guarantor and to perform all of the obligations and
agreements of a Guarantor under the Indenture.



     SECTION 2.2 Guarantee. Services hereby fully, unconditionally and irrevocably
guarantees, as primary obligor and not merely as surety, jointly and severally with each other
Guarantor, to each Holder of the Securities and the Trustee, the full and punctual payment when
due, whether at maturity, by acceleration, by redemption, by repurchase or otherwise, of all of the
Obligations of the Company to the Trustee and to the Securityholders under the Indenture in
accordance with Article X of the Indenture.



ARTICLE III




Miscellaneous




     SECTION 3.1 Notices. All notices and other communications to a Guarantor or the
Company shall be given as provided in the Indenture to the Guarantor or the Company, as the case
may be, at its address set forth below, with a copy to the Company as provided in the Indenture for
notices to the Company.



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     SECTION 3.2 Parties. Nothing expressed or mentioned herein is intended or shall be
construed to give any Person, firm or corporation, other than the Holders and the Trustee, any
legal or equitable right, remedy or claim under or in respect of this Second Supplemental Indenture
or the Indenture or any provision herein or therein contained.



     SECTION 3.3 Governing Law. This Second Supplemental Indenture shall be governed by
the laws of the State of New York, without regard to conflicts of law principles.



     SECTION 3.4 Severability Clause. In case any provision in this Second 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 and such provision
shall be ineffective only to the extent of such invalidity, illegality or unenforceability.



     SECTION 3.5 Ratification of Indenture; Second Supplemental Indenture Part of
Indenture. Except as expressly amended hereby, the Indenture is in all respects ratified and
confirmed and all the terms, conditions and provisions thereof shall remain in full force and
effect. This Second Supplemental Indenture shall form a part of the Indenture for all purposes,
and every holder of Securities heretofore or hereafter authenticated and delivered shall be bound
hereby.



     SECTION 3.6 Counterparts. The parties hereto may sign one or more copies of this
Second Supplemental Indenture in counterparts, all of which together shall constitute one and the
same agreement.



     SECTION 3.7 Headings. The headings of the Articles and the sections in this Second
Supplemental Indenture are for convenience of reference only and shall not be deemed to alter or
affect the meaning or interpretation of any provisions hereof.



     SECTION 3.8 Trustee. The Trustee makes no representations as to the validity or
sufficiency of this Second Supplemental Indenture. The recitals and statements herein are deemed
to be those of the Company and the Guarantors and not of the Trustee.



[Remainder of this page intentionally left blank.]





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     IN WITNESS WHEREOF, the parties hereto have caused this Second Supplemental Indenture to be
duly executed as of the date first above written.



	 	 	 	 	 
	Address:

	 	REYNOLDS AMERICAN INC.,
	401 North Main Street
	 	 	 	 
	Winston-Salem, NC 27101
	 	 	 	 
	 

	 	By:
	 	/s/ Daniel Fawley
	 

	 	 	 	 
	 

	 	 	 	Name: Daniel A. Fawley

Title:   Senior Vice President and Treasurer
	 
	 	 	 	 
	 
	 	 	 	 
	Address:

	 	SANTA FE NATURAL TOBACCO COMPANY, INC.,

	1368 Cerrillos Road

	 	     as Guarantor
	Santa Fe, New Mexico 87505
	 	 	 	 
	 
	 	 	 	 
	 

	 	By:
	 	/s/ Daniel Fawley
	 

	 	 	 	 
	 

	 	 	 	Name: Daniel A. Fawley

Title:   Assistant Treasurer
	 
	 	 	 	 
	 
	 	 	 	 
	Address:

	 	LANE LIMITED,
	2280 Mountain Industrial Blvd.

	 	     as Guarantor
	Tucker, GA 30084
	 	 	 	 
	 
	 	 	 	 
	 

	 	By:
	 	/s/ Daniel Fawley
	 

	 	 	 	 
	 

	 	 	 	Name: Daniel A. Fawley

Title:   Assistant Treasurer
	 
	 	 	 	 
	 
	 	 	 	 
	Address:

	 	R. J. REYNOLDS TOBACCO COMPANY,
	401 North Main Street

	 	     as Guarantor
	Winston-Salem, NC 27101
	 	 	 	 
	 
	 	 	 	 
	 

	 	By:
	 	/s/ Daniel Fawley
	 

	 	 	 	 
	 

	 	 	 	Name: Daniel A. Fawley

Title:   Treasurer
	 
	 	 	 	 
	 
	 	 	 	 
	Address:

	 	R. J. REYNOLDS TOBACCO CO.,
	401 North Main Street

	 	     as Guarantor
	Winston-Salem, NC 27101
	 	 	 	 
	 
	 	 	 	 
	 

	 	By:
	 	/s/ Daniel Fawley
	 

	 	 	 	 
	 

	 	 	 	Name: Daniel A. Fawley

Title:   Vice President and Treasurer






SIGNATURE PAGE TO SECOND SUPPLEMENTAL INDENTURE





 









 








	 	 	 	 	 
	Address:

	 	REYNOLDS FINANCE COMPANY
	1201 Market Street

	 	     as Guarantor
	Suite 1702
	 	 	 	 
	Wilmington, DE 19801
	 	 	 	 
	 

	 	By:
	 	/s/ Kathryn A. Premo
	 

	 	 	 	 
	 

	 	 	 	Name: Kathryn A. Premo

Title:   Treasurer
	 
	 	 	 	 
	 
	 	 	 	 
	Address:

	 	REYNOLDS INNOVATIONS, INC.
	327 Hillsborough Street

	 	     as Guarantor
	Raleigh, NC 27603
	 	 	 	 
	 
	 	 	 	 
	 

	 	By:
	 	/s/ Daniel Fawley
	 

	 	 	 	 
	 

	 	 	 	Name: Daniel A. Fawley

Title:   Treasurer
	 
	 	 	 	 
	 
	 	 	 	 
	Address:

	 	CONWOOD HOLDINGS, INC.,
	813 Ridge Lake Boulevard

	 	     as Guarantor
	Suite 100
	 	 	 	 
	Memphis, TN 38119
	 	 	 	 
	 

	 	By:
	 	/s/ Daniel Fawley
	 

	 	 	 	 
	 

	 	 	 	Name: Daniel A. Fawley

Title:   Vice President and Treasurer
	 
	 	 	 	 
	 
	 	 	 	 
	Address:

	 	CONWOOD COMPANY, LLC,
	813 Ridge Lake Boulevard

	 	     as Guarantor
	Suite 100
	 	 	 	 
	Memphis, TN 38119
	 	 	 	 
	 

	 	By:
	 	/s/ Daniel Fawley
	 

	 	 	 	 
	 

	 	 	 	Name: Daniel A. Fawley

Title:   Vice President and Treasurer
	 
	 	 	 	 
	 
	 	 	 	 
	Address:

	 	ROSSWIL LLC,
	813 Ridge Lake Boulevard

	 	     as Guarantor
	Suite 100
	 	 	 	 
	Memphis, TN 38119
	 	 	 	 
	 

	 	By:
	 	/s/ Daniel Fawley
	 

	 	 	 	 
	 

	 	 	 	Name: Daniel A. Fawley

Title:   Vice President and Treasurer






SIGNATURE PAGE TO SECOND SUPPLEMENTAL INDENTURE






 









 








	 	 	 	 	 
	Address:

	 	R.J. REYNOLDS TOBACCO HOLDINGS, INC.,
	401 North Main Street

	 	     as Guarantor
	Winston-Salem, NC 27101
	 	 	 	 
	 
	 	 	 	 
	 

	 	By:
	 	/s/ Daniel Fawley
	 

	 	 	 	 
	 

	 	 	 	Name: Daniel A. Fawley

Title:   Senior Vice President and Treasurer
	 
	 	 	 	 
	 
	 	 	 	 
	Address:

	 	R. J. REYNOLDS GLOBAL PRODUCTS, INC.,
	401 North Main Street

	 	     as Guarantor
	Winston-Salem, NC 27101
	 	 	 	 
	 
	 	 	 	 
	 

	 	By:
	 	/s/ Daniel Fawley
	 

	 	 	 	 
	 

	 	 	 	Name: Daniel A. Fawley

Title:   Vice President and Treasurer
	 
	 	 	 	 
	 
	 	 	 	 
	Address:

	 	RAI SERVICES COMPANY,
	401 North Main Street

	 	     as Guarantor
	Winston-Salem, NC 27101
	 	 	 	 
	 
	 	 	 	 
	 

	 	By:
	 	/s/ Daniel Fawley
	 

	 	 	 	 
	 

	 	 	 	Name: Daniel A. Fawley

Title:   Treasurer






SIGNATURE PAGE TO SECOND SUPPLEMENTAL INDENTURE






 









 








	 	 	 	 	 
	THE BANK OF NEW YORK MELLON

TRUST COMPANY, N.A., as Trustee
	 
	 	 	 	 
	By:
	 	/s/ Christie Leppert
	 	 	 
	 	 	Name: Christie Leppert

Title:   Assistant Vice President






SIGNATURE PAGE TO SECOND SUPPLEMENTAL INDENTURE