Document:

EX-4.1 Supplemental Indenture

Exhibit 4.1

SUPPLEMENTAL INDENTURE

     This SUPPLEMENTAL INDENTURE (this “Supplemental Indenture”), dated as of October 6, 2008,
among Waste Services, Inc. (or its permitted successor), a Delaware corporation (the “Company”),
the Guarantors (as defined in the Indenture referred to herein), and Wells Fargo Bank, National
Association, as trustee under the Indenture referred to below (the “Trustee”).

W I T N
E S S E T H

     WHEREAS, the Company has heretofore executed and delivered to the Trustee an indenture, dated
as of April 30, 2004 (as supplemented to the date hereof, the “Indenture”), providing for the
issuance of 91/2% Senior Subordinated Notes due 2014 (the “Notes”);

     WHEREAS, Section 9.02 of the Indenture provides that the Company and the Trustee may amend or
supplement the Indenture, the Notes and the Note Guarantees with the written consent of the holders
(the “Holders”) of a majority in aggregate principal amount of the then outstanding Notes, except
for certain specific events which require the unanimous written consent vote of the Holders of the
Notes;

     WHEREAS, the Company undertook a consent solicitation (the “Consent Solicitation”) pursuant to
a Consent Solicitation Statement dated September 26, 2008 (the “Consent Solicitation Statement”),
seeking the written consent of Holders to implement the amendments set forth in Sections 2 and 3 of
this Supplemental Indenture (the “Amendments”);

     WHEREAS, in connection with the Consent Solicitation, the Company desires to refinance (the
“Refinancing”) all existing indebtedness under the existing senior secured credit facilities of the
Company and Waste Services (CA) Inc., whereby the Company and its subsidiaries would (i) receive
proceeds of at least $240,000,000 from new senior secured credit facilities and (ii) repay all
outstanding amounts under the Company’s existing senior secured credit facilities (the “Refinancing
Condition”);

     WHEREAS, the Company has received pursuant to the Consent Solicitation Statement the valid
written consents of the Holders of at least a majority in aggregate principal amount outstanding of
the Notes consenting to the substance of the Amendments set forth in this Supplemental Indenture;

     WHEREAS, subject to the satisfaction or waiver of all conditions to the Consent Solicitation
set forth in the Consent Solicitation Statement, including the condition that Holders of at least a
majority in aggregate principal amount outstanding of the Notes consent to the substance of the
Amendments set forth in this Supplemental Indenture, the Company is obligated to pay to each Holder
a consent fee (the “Consent Payment”) equal to 0.75% of the outstanding principal amount of the
Notes for which such Holder provided its consent prior to the Expiration Time (as such term is
defined in the Consent Solicitation Statement) and did not revoke such consent prior to the
Expiration Time;

     WHEREAS, all conditions and requirements necessary to make this Supplemental Indenture a
valid, binding and legal instrument in accordance with the terms of the Indenture

 

 

have been performed and fulfilled and the execution and delivery hereof have been in all
respects duly authorized; and

     WHEREAS, in accordance with the terms of the Indenture, the Company has requested that the
Trustee execute and deliver this Supplemental Indenture and has delivered to the Trustee a copy of
the resolutions of the Board of Directors authorizing the execution of this Supplemental Indenture.

     NOW, THEREFORE, in consideration of the foregoing and for other good and valuable
consideration, the receipt of which is hereby acknowledged, the Company, the Guarantors and the
Trustee mutually covenant and agree for the equal and ratable benefit of the Holders of the Notes
as follows:

     1. Capitalized Terms. Capitalized terms used herein without definition shall have the
meanings assigned to them in the Indenture.

     2. Amendment to Definition of Senior Debt in Section 1.01 of the Indenture. The
definition of Senior Debt in Section 1.01 of the Indenture is hereby amended and restated in its
entirety to read as follows:

“Senior Debt” means:

     (1) all Indebtedness of the Company, any Guarantor, Capital or any Foreign
Subsidiary of Capital outstanding under Credit Facilities and all Hedging
Obligations with respect thereto whether outstanding on the date of this Indenture
or incurred thereafter;

     (2) any other Indebtedness of the Company or any Guarantor permitted to be
incurred under the terms of this Indenture, unless the instrument under which such
Indebtedness is incurred expressly provides that it is on a parity with or
subordinated in right of payment to the Notes or any Note Guarantee; and

     (3) all Obligations with respect to the items listed in the preceding clauses
(1) and (2).

Notwithstanding anything to the contrary in the preceding, Senior Debt shall not
include:

     (1) any liability for federal, state, local or other taxes owed or owing by the
Company, any Guarantor, Capital or any Foreign Subsidiary of Capital;

     (2) any intercompany Indebtedness of the Company or any of its Subsidiaries to
the Company or any of its Affiliates;

     (3) any trade payables;

     (4) the portion of any Indebtedness that is incurred in violation of this
Indenture; provided that Indebtedness under a Credit Facility shall not cease to be

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Senior Debt under this clause (4) if the lenders obtained a certificate from an
officer of the Company as of the date of the incurrence of such Indebtedness to the
effect that such Indebtedness was permitted to be incurred under this Indenture; or

     (5) Indebtedness which is classified as non-recourse in accordance with GAAP or
any unsecured claim arising in respect thereof by reason of the application of
Section 1111(b)(1) of the United States Bankruptcy Code.

     3. Amendment to Section 4.09(a) of the Indenture. Section 4.09(a) of the Indenture is
hereby amended and restated in its entirety to read as follows:

     (a) The Company shall not, and shall not permit any of its Restricted
Subsidiaries to, directly or indirectly, create, incur, issue, assume, guarantee or
otherwise become directly or indirectly liable, contingently or otherwise, with
respect to (collectively, “incur”) any Indebtedness (including Acquired Debt), and
the Company shall not issue any Disqualified Stock and shall not permit any of its
Restricted Subsidiaries to issue any shares of preferred stock; provided, however,
that the Company may incur Indebtedness (including Acquired Debt) or issue
Disqualified Stock, and the Guarantors may incur Indebtedness (including Acquired
Debt) or issue preferred stock, if the Fixed Charge Coverage Ratio for the most
recently ended four full fiscal quarters of the Company, for which internal
consolidated financial statements are available immediately preceding the date on
which such additional Indebtedness is incurred or such Disqualified Stock or such
preferred stock is issued, as the case may be, would have been at least 2.0 to 1.0,
determined on a pro forma basis (including a pro forma application of the net
proceeds therefrom), as if the additional Indebtedness had been incurred or the
Disqualified Stock or the preferred stock had been issued, as the case may be, at
the beginning of such four-quarter period.

     4. Effectiveness of Amendments.

          (a) This Supplemental Indenture shall become effective, and shall bind the parties hereto,
upon its execution by the Company, the Guarantors and the Trustee.

          (b) Notwithstanding the foregoing, the Amendments shall not become operative, and shall not be
binding on the Company, the Guarantors or the Trustee, until delivery by the Company to the Trustee
of written notice that (i) the Refinancing Condition has been satisfied or waived by the Company
and (ii) the General Condition has been satisfied or waived by the Company. In the event that
(A) the Refinancing Condition has not been satisfied or waived by the Company or (B) the General
Condition has not been satisfied or waived by the Company, the Amendments shall not become
operative and shall not bind the Company, any Guarantors or the Trustee and this Supplemental
Indenture shall lapse automatically and be of no further force or effect. Satisfaction of the
“General Condition” means the absence of any existing or proposed law or regulation that would, and
the absence of any injunction or action or other proceeding that (in the case of any action or
proceeding, if adversely determined) would, make unlawful or invalid or enjoin or delay the
implementation of the Amendments, the entering

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into of the Supplemental Indenture or the payment of the Consent Payment or question the
legality or validity of any thereof.

     5. NEW YORK LAW TO GOVERN. THIS SUPPLEMENTAL INDENTURE SHALL BE GOVERNED BY AND
CONSTRUED IN ACCORDANCE WITH THE LAW OF THE STATE OF NEW YORK BUT WITHOUT GIVING EFFECT TO
APPLICABLE PRINCIPLES OF CONFLICTS OF LAW TO THE EXTENT THAT THE APPLICATION OF THE LAWS OF ANOTHER
JURISDICTION WOULD BE REQUIRED THEREBY.

     6. Counterparts. The parties may sign any number of copies of this Supplemental
Indenture. Each signed copy shall be an original, but all of them together represent the same
agreement.

     7. Effect of Headings. The Section headings herein are for convenience only and shall
not affect the construction hereof.

     8. Effect of Supplemental Indenture. Except as amended by this Supplemental Indenture,
the terms and provisions of the Indenture shall remain in full force and effect.

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

[Signature pages follow]

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

	 	 	 	 	 
	COMPANY:                                              	WASTE SERVICES, INC.

 	 
	 	By:  	/s/ Ivan R. Cairns
 	 
	 	 	Ivan R. Cairns 	 
	 	 	Executive Vice President, General Counsel and

Secretary 	 

	 	 	 	 	 
	GUARANTORS:                               	WASTE SERVICES OF FLORIDA, INC.

 	 
	 	By:  	/s/ Ivan R. Cairns
 	 
	 	 	Ivan R. Cairns 	 
	 	 	Vice President and Secretary 	 

	 	 	 	 	 
	 	TAFT RECYCLING, INC.

 	 
	 	By:  	/s/ Ivan R. Cairns
 	 
	 	 	Ivan R. Cairns 	 
	 	 	Vice President and Secretary 	 
	 
	 	SANFORD RECYCLING AND TRANSFER, INC.

 	 
	 	By:  	/s/ Ivan R. Cairns
 	 
	 	 	Ivan R. Cairns 	 
	 	 	Vice President and Secretary 	 
	 
	 	JACKSONVILLE FLORIDA LANDFILL, INC.

 	 
	 	By:  	/s/ Ivan R. Cairns
 	 
	 	 	Ivan R. Cairns 	 
	 	 	Vice President and Secretary 	 
	 

[Signature Page to Supplemental Indenture]

 

 

	 	 	 	 	 
	 	OMNI WASTE OF OSCEOLA COUNTY LLC

 	 
	 	By:  	/s/ Ivan R. Cairns
 	 
	 	 	Ivan R. Cairns 	 
	 	 	Manager 	 
	 
	 	WASTE SERVICES OF ARIZONA, INC.

 	 
	 	By:  	/s/ Ivan R. Cairns
 	 
	 	 	Ivan R. Cairns 	 
	 	 	Vice President and Secretary 	 
	 
	 	SUN COUNTRY MATERIALS, LLC

 	 
	 	By:  	/s/ Ivan R. Cairns
 	 
	 	 	Ivan R. Cairns 	 
	 	 	Vice President and Secretary 	 
	 
	 	FREEDOM RECYCLING HOLDINGS, LLC

 	 
	 	By:  	/s/ Ivan R. Cairns
 	 
	 	 	Ivan R. Cairns 	 
	 	 	Vice President and Secretary 	 
	 
	 	SLD LANDFILL, INC.

 	 
	 	By:  	/s/ Ivan R. Cairns
 	 
	 	 	Ivan R. Cairns 	 
	 	 	Vice President and Secretary 	 
	 

[Signature Page to Supplemental Indenture]

 

 

	 	 	 	 	 
	                TRUSTEE:              	WELLS FARGO BANK, NATIONAL ASSOCIATION,

as Trustee

 	 
	 	By:  	/s/ Julie Salovitch-Miller
 	 
	 	Name:  	 	Julie Salovitch-Miller 	 
	 	Title:  	 	Vice President 	 
	 

[Signature Page to Supplemental Indenture]EX-4.2 Supplemental Indenture

Exhibit 4.2

SUPPLEMENTAL INDENTURE

     SUPPLEMENTAL INDENTURE (this “Supplemental Indenture”), dated as of October 8, 2008, among
Capital Environmental Holdings Company, a Nova Scotia unlimited liability company, Waste Services
(CA) Inc., an Ontario corporation and Ram-Pak Compaction Systems Ltd., a Canadian corporation (each
a “Guaranteeing Subsidiary”), each a subsidiary of Waste Services, Inc. (or its permitted
successor), a Delaware corporation (the “Company”), the Company, the other Guarantors (as defined
in the Indenture referred to herein) party to the Indenture on the date hereof and Wells Fargo
Bank, National Association, as trustee under the Indenture referred to below (the “Trustee”).

W I T N
E S S E T H

     WHEREAS, the Company has heretofore executed and delivered to the Trustee an indenture, dated
as of April 30, 2004 and amended by a supplemental indenture dated as of October 6, 2008
(collectively, the “Indenture”), providing for the issuance of 91/2% Senior Subordinated Notes due
2014 (the “Notes”);

     WHEREAS, the Indenture provides that under certain circumstances the Guaranteeing Subsidiary
shall execute and deliver to the Trustee a supplemental indenture pursuant to which the
Guaranteeing Subsidiary shall unconditionally guarantee all of the Company’s Obligations under the
Notes and the Indenture on the terms and conditions set forth herein (the “Note Guarantee”); and

     WHEREAS, pursuant to Section 9.01 of the Indenture, the Trustee is authorized to execute and
deliver this Supplemental Indenture;

     NOW, THEREFORE, in consideration of the foregoing and for other good and valuable
consideration, the receipt of which is hereby acknowledged, the Guaranteeing Subsidiary and the
Trustee mutually covenant and agree for the equal and ratable benefit of the Holders of the Notes
as follows:

     1. Capitalized Terms. Capitalized terms used herein without definition shall have the
meanings assigned to them in the Indenture.

     2. Agreement To Guarantee. Each Guaranteeing Subsidiary hereby agrees to provide an
unconditional Guarantee on the terms and subject to the conditions set forth in the Note Guarantee
and in the Indenture including but not limited to Article 11 thereof.

     3. No Recourse Against Others. No past, present or future director, officer,
employee, incorporator, stockholder or agent of each Guaranteeing Subsidiary, as such, shall have
any liability for any obligations of the Company or any Guarantor (including such Guaranteeing
Subsidiary) under the Notes, any Note Guarantees, the Indenture or this Supplemental Indenture, as
applicable, or for any claim based on, in respect of, or by reason of, such obligations or their
creation. Each Holder of the Notes by accepting a Note waives and releases all such liability.
This waiver and release are part of the consideration for issuance of the Notes. Such waiver may
not be effective to waive liabilities under the federal securities laws and it is the view of the
SEC that such a waiver is against public policy.

 

 

     4. NEW YORK LAW TO GOVERN. THIS SUPPLEMENTAL INDENTURE SHALL BE GOVERNED BY AND
CONSTRUED IN ACCORDANCE WITH THE LAW OF THE STATE OF NEW YORK.

     5. Counterparts. The parties may sign any number of copies of this Supplemental
Indenture. Each signed copy shall be an original, but all of them together represent the same
agreement.

     6. Effect of Headings. The Section headings herein are for convenience only and shall
not affect the construction hereof.

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

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

	 	 	 	 	 
	 	CAPITAL ENVIRONMENTAL HOLDINGS COMPANY

 	 
	 	By:  	/s/ Ivan R. Cairns
 	 
	 	 	Ivan R. Cairns 	 
	 	 	President and Secretary 	 
	 
	 	WASTE SERVICES (CA) INC.

 	 
	 	By:  	/s/ Ivan R. Cairns
 	 
	 	 	Ivan R. Cairns 	 
	 	 	Vice President and Secretary 	 
	 
	 	RAM-PAK COMPACTION SYSTEMS LTD.

 	 
	 	By:  	/s/ Ivan R. Cairns
 	 
	 	 	Ivan R. Cairns 	 
	 	 	Vice President and Secretary 	 

Page 2 of 3

 

	 	 	 	 	 

	 	 	 	 	 
	 	WELLS FARGO BANK, NATIONAL ASSOCIATION, 

as Trustee

 	 
	 	By:  	/s/ Julie Salovitch-Miller
 	 
	 	 	Name:  	Julie Salovitch-Miller 	 
	 	 	Title:  	Vice President 	 

Page 3 of 3

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