Document:

Exhibit 4.2

 

Execution Version 

 

OVERSEAS SHIPHOLDING GROUP, INC.

and

WILMINGTON TRUST COMPANY,

as Trustee

__________________________________________

 

FIFTH SUPPLEMENTAL INDENTURE

Dated as of December 16, 2015

___________________________________________

 

 

7.50% Senior Notes I
due 2021

 

 

 

     
 

     

    

 

FIFTH SUPPLEMENTAL INDENTURE

 

THIS FIFTH SUPPLEMENTAL INDENTURE, effective as of December
16, 2015 (this “Fifth Supplemental Indenture”), is entered into between Overseas Shipholding Group, Inc., a
corporation duly organized and existing under the laws of the State of Delaware (the “Company”), having its
principal office at 1301 Avenue of the Americas, New York, New York 10019, and Wilmington Trust Company, a Delaware trust company,
as trustee (the “Trustee”).

 

WHEREAS, the Company and the Trustee have executed and delivered
an indenture (the “Original Indenture”), dated as of March 7, 2003, as supplemented by the Second Supplemental
Indenture dated as of August 5, 2014 (the “Second Supplemental Indenture”; the Original Indenture, as supplemented
by the Second Supplemental Indenture, the “Indenture”), that governs the Company’s existing outstanding
$6,508,000 aggregate principal amount of 7.50% Senior Notes I due 2021 (the “Notes”), of which $3,000,000 in
aggregate principal amount is held by the Company as of the date hereof;

 

WHEREAS, Section 902 of the Original Indenture provides, among
other things, that, with the consent of the Holders of not less than 66 2/3% in principal amount of the Outstanding Securities
of each series affected by such supplemental indenture, the Company, when authorized by a Board Resolution, and the Trustee may
enter into a supplemental indenture for the purpose of adding any provisions to or changing in any manner or eliminating any of
the provisions of the Indenture or of modifying in any manner the rights of the Holders of Securities of such series under the
Indenture, subject to those certain exceptions set forth in Section 902 thereof;

 

WHEREAS, the Company distributed an offer to purchase and consent
solicitation statement (the “Statement”) dated as of December 2, 2015 to the Holders of the Notes in connection
with the offer to purchase for cash any and all of such Notes and the concurrent solicitation of such Holders’ consents to
a proposed amendment to the Indenture (the “Tender Offer and Consent Solicitation”);

 

WHEREAS, consent by the Holders of not less than 66 2/3% in
principal amount of the Outstanding Notes is required to execute this Fifth Supplemental Indenture;

 

WHEREAS, pursuant to the Statement, in accordance with the provisions
of the Indenture, the Holders of not less than 66 2/3% in principal amount of the Outstanding Notes have consented to the amendment
to the Indenture effected by this Fifth Supplemental Indenture, evidence of such consents has been provided by the Company to the
Trustee, and all other conditions precedent, if any, provided for in the Indenture relating to the execution of this Fifth Supplemental
Indenture have been complied with as of the date hereof;

 

WHEREAS, pursuant to Section 902 of the Indenture, the Trustee
is authorized to execute and deliver this Fifth Supplemental Indenture; and

 

WHEREAS, all acts and requirements necessary to make this Fifth
Supplemental Indenture the legal, valid and binding obligation of the Company have been done.

 

NOW THEREFORE, in consideration of the foregoing and for other
good and valuable consideration, the receipt of which is hereby acknowledged, the parties agree as follows:

 

    	 	1	 

     

    

 

ARTICLE ONE

 

DEFINITIONS AND OTHER PROVISIONS OF GENERAL
APPLICATION

 

Section 101.Relation to Indenture. This Fifth Supplemental
Indenture constitutes an integral part of the Indenture.

 

Section 102Definition of Terms.

 

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

 

(b) the following terms have the meanings given to them
in this Section 102(b):

 

“Fifth Supplemental Indenture” has the meaning
set forth in the recitals to this Fifth Supplemental Indenture.

 

“OBS” has the meaning set forth in Section
201 of this Fifth Supplemental Indenture.

 

“OBS ABL Facility” means the ABL Credit Agreement
dated as of August 5, 2014, among the Company, OBS, certain subsidiaries of OBS as co-borrowers, the other guarantors party thereto,
various lenders, Jefferies Finance LLC, Barclays Bank PLC and UBS Securities LLC, as joint lead arrangers and joint book running
managers, Wells Fargo Bank, National Association, as administrative agent, Barclays Bank PLC and UBS Securities LLC, as co-documentation
agents, Jefferies Finance LLC, as syndication agent, and Wells Fargo Bank, National Association, as collateral agent and mortgage
trustee, swingline lender and issuing bank, as amended on June 3, 2015.

 

“OBS Term Loan Facility” means the DTL Credit
Agreement dated as of August 5, 2014, among the Company, OBS, the other guarantors party thereto, various lenders, Jefferies Finance
LLC, Barclays Bank PLC and UBS Securities LLC, as joint lead arrangers and joint book running managers, Jefferies Finance LLC,
as administrative agent, Barclays Bank PLC and UBS Securities LLC, as co-documentation agents, and Jefferies Finance LLC, as syndication
agent, collateral agent and mortgage trustee, as amended on June 3, 2015.

 

“OIN” has the meaning set forth in Section
201 of this Fifth Supplemental Indenture.

 

“Original Indenture” has the meaning set
forth in the recitals to this Fifth Supplemental Indenture.

 

ARTICLE TWO

 

AMENDMENTS TO THE INDENTURE

 

Section 201Amendment to Section 801 of the Original Indenture.
Section 801 of the Original Indenture is hereby amended to add the following underlined language to the first paragraph of such
section:

 

    	 	2	 

     

    

 

“The Company shall not consolidate
with or merge into any other Person or convey, transfer or lease its properties and assets substantially as an entirety to any
Person, and the Company shall not permit any Person to consolidate with or merge into the Company or convey, transfer or lease
its properties and assets substantially as an entirety to the Company (provided, however, that for the
purposes of this Section 801, neither OSG International, Inc., a Marshall Islands corporation that is a subsidiary of the Company
(“OIN”), nor (i) any or all of OIN’s assets or OIN’s subsidiaries’ assets, (ii) any entity into which
OIN or its subsidiaries may be merged or converted or with which they may be consolidated, (iii) any entity resulting from any
merger, conversion or consolidation to which OIN or its subsidiaries may be a party, or (iv) any entity, that is not currently
owned directly or indirectly by the Company, that acquires OIN or any or all of the assets of OIN or any of its subsidiaries’
assets (provided in each case that OIN and the assets and entities described in (i) through (iv) above, collectively, may include
assets directly or indirectly transferred from OSG Bulk Ships, Inc. (“OBS”) to OIN and such other entities only to
the extent that such transfers would, to the extent applicable to such transfer, be permitted under each of Sections 6.09 (Transactions
with Affiliates), 6.08 (Dividends) and 6.04 (Investments, Loans and Advances) of each of the OBS ABL Facility and the OBS Term
Loan Facility, each as in effect on the date hereof), constitutes substantially an entirety of the Company’s assets)
unless:..”

 

ARTICLE THREE

 

GENERAL PROVISIONS

 

Section 301.Effectiveness. The provisions of this
Fifth Supplemental Indenture shall become effective immediately upon the execution and delivery by the Company and the Trustee
of this Fifth Supplemental Indenture; however, Section 201 of this Fifth Supplemental Indenture will not become operative until
the Company has delivered to the Trustee an Officers’ Certificate certifying that the amounts payable by the Company pursuant
to the terms of the Tender Offer and Consent Solicitation have been paid.

 

Section 302.Ratification of Indenture. The Indenture
is in all respects acknowledged, ratified and confirmed, and shall continue in full force and effect in accordance with the terms
thereof and as supplemented by this Fifth Supplemental Indenture. The Indenture and this Fifth Supplemental Indenture, shall be
read, taken and construed as one and the same instrument.

 

Section 303.Effect of Headings. The Article and Section
headings in this Fifth Supplemental Indenture are for convenience only and shall not affect the construction of this Fifth Supplemental
Indenture.

 

Section 304.Governing Law. THIS FIFTH SUPPLEMENTAL
INDENTURE SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAWS OF THE STATE OF NEW YORK.

 

Section 305.Multiple Counterparts. This Fifth 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.

 

Section 306.Successors and Assigns. All agreements
of the Company in this Fifth Supplemental Indenture shall bind its successors. All agreements of the Trustee in this Fifth Supplemental
Indenture shall bind its successors.

 

Section 307.Trustee Not Responsible for Recitals.
The recitals in this Fifth Supplemental Indenture are made by the Company, and the Trustee assumes no responsibility for the correctness
of such recitals.

 

    	 	3	 

     

    

 

IN WITNESS WHEREOF, the parties to this
Fifth Supplemental Indenture have caused the Fifth Supplemental Indenture to be duly executed as of day and year first above written.

 

	 	OVERSEAS SHIPHOLDING GROUP, INC.	 
	 	 	 	 
	 	 	 	 
	 	By 	/s/ Rick F. Oricchio	 
		Name:	Rick F. Oricchio	 
	 	Title: 	Senior Vice President, Chief Financial Officer	 
	 	 	 	 
	 	 	 	 
	 	 	 	 
	 	WILMINGTON TRUST COMPANY,

	 
	 	 	 	 
	 	as Trustee	 
	 	 	 	 
	 	 	 	 
	 	By 	/s/ W. Thomas Morris, II	 
	 	Name:	W. Thomas Morris, II

	 
	 	Title:	Vice President	 

 

 

    	 	4Exhibit 4.3

 

Execution Version 

  

OVERSEAS SHIPHOLDING GROUP, INC.

and

WILMINGTON TRUST COMPANY,

as Trustee

__________________________________________

 

SIXTH SUPPLEMENTAL INDENTURE

Dated as of December 16, 2015

___________________________________________

 

 

7.50% Senior Notes II
due 2021

 

 

 

     
 

     

    

 

SIXTH SUPPLEMENTAL INDENTURE

 

THIS SIXTH SUPPLEMENTAL INDENTURE, effective as of December
16, 2015 (this “Sixth Supplemental Indenture”), is entered into between Overseas Shipholding Group, Inc., a
corporation duly organized and existing under the laws of the State of Delaware (the “Company”), having its
principal office at 1301 Avenue of the Americas, New York, New York 10019, and Wilmington Trust Company, a Delaware trust company,
as trustee (the “Trustee”).

 

WHEREAS, the Company and the Trustee have executed and delivered
an indenture (the “Original Indenture”), dated as of March 7, 2003, as supplemented by the Third Supplemental
Indenture dated as of August 5, 2014 (the “Third Supplemental Indenture”; the Original Indenture, as supplemented
by the Third Supplemental Indenture, the “Indenture”), that governs the Company’s existing outstanding
$138,708,000 aggregate principal amount of 7.50% Senior Notes II due 2021 (the “Notes”), of which $36,143,000
in aggregate principal amount is held by the Company as of the date hereof;

 

WHEREAS, Section 902 of the Original Indenture provides, among
other things, that, with the consent of the Holders of not less than 66 2/3% in principal amount of the Outstanding Securities
of each series affected by such supplemental indenture, the Company, when authorized by a Board Resolution, and the Trustee may
enter into a supplemental indenture for the purpose of adding any provisions to or changing in any manner or eliminating any of
the provisions of the Indenture or of modifying in any manner the rights of the Holders of Securities of such series under the
Indenture, subject to those certain exceptions set forth in Section 902 thereof;

 

WHEREAS, the Company distributed an offer to purchase and consent
solicitation statement (the “Statement”) dated as of December 2, 2015 to the Holders of the Notes in connection
with the offer to purchase for cash any and all of such Notes and the concurrent solicitation of such Holders’ consents to
a proposed amendment to the Indenture (the “Tender Offer and Consent Solicitation”);

 

WHEREAS, consent by the Holders of not less than 66 2/3% in
principal amount of the Outstanding Notes is required to execute this Sixth Supplemental Indenture;

 

WHEREAS, pursuant to the Statement, in accordance with the provisions
of the Indenture, the Holders of not less than 66 2/3% in principal amount of the Outstanding Notes have consented to the amendment
to the Indenture effected by this Sixth Supplemental Indenture, evidence of such consents has been provided by the Company to the
Trustee, and all other conditions precedent, if any, provided for in the Indenture relating to the execution of this Sixth Supplemental
Indenture have been complied with as of the date hereof;

 

WHEREAS, pursuant to Section 902 of the Indenture, the Trustee
is authorized to execute and deliver this Sixth Supplemental Indenture; and

 

WHEREAS, all acts and requirements necessary to make this Sixth
Supplemental Indenture the legal, valid and binding obligation of the Company have been done.

 

    	 	1	 

     

    

 

NOW THEREFORE, in consideration of the foregoing and for other
good and valuable consideration, the receipt of which is hereby acknowledged, the parties agree as follows:

 

ARTICLE ONE

 

DEFINITIONS AND OTHER PROVISIONS OF GENERAL
APPLICATION

 

Section 101.Relation to Indenture. This Sixth Supplemental
Indenture constitutes an integral part of the Indenture.

 

Section 102Definition of Terms.

 

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

 

(b) the following terms have the meanings given to them
in this Section 102(b):

 

“OBS” has the meaning set forth in Section
201 of this Sixth Supplemental Indenture.

 

“OBS ABL Facility” means the ABL Credit Agreement
dated as of August 5, 2014, among the Company, OBS, certain subsidiaries of OBS as co-borrowers, the other guarantors party thereto,
various lenders, Jefferies Finance LLC, Barclays Bank PLC and UBS Securities LLC, as joint lead arrangers and joint book running
managers, Wells Fargo Bank, National Association, as administrative agent, Barclays Bank PLC and UBS Securities LLC, as co-documentation
agents, Jefferies Finance LLC, as syndication agent, and Wells Fargo Bank, National Association, as collateral agent and mortgage
trustee, swingline lender and issuing bank, as amended on June 3, 2015.

 

“OBS Term Loan Facility” means the DTL Credit
Agreement dated as of August 5, 2014, among the Company, OBS, the other guarantors party thereto, various lenders, Jefferies Finance
LLC, Barclays Bank PLC and UBS Securities LLC, as joint lead arrangers and joint book running managers, Jefferies Finance LLC,
as administrative agent, Barclays Bank PLC and UBS Securities LLC, as co-documentation agents, and Jefferies Finance LLC, as syndication
agent, collateral agent and mortgage trustee, as amended on June 3, 2015.

 

“OIN” has the meaning set forth in Section
201 of this Sixth Supplemental Indenture.

 

“Original Indenture” has the meaning set
forth in the recitals to this Sixth Supplemental Indenture.

 

“Sixth Supplemental Indenture” has the meaning
set forth in the recitals to this Sixth Supplemental Indenture.

 

ARTICLE TWO

 

AMENDMENTS TO THE INDENTURE

 

Section 201Amendment to Section 801 of the Original Indenture.
Section 801 of the Original Indenture is hereby amended to add the following underlined language to the first paragraph of such
section:

 

    	 	2	 

     

    

 

“The Company shall not consolidate
with or merge into any other Person or convey, transfer or lease its properties and assets substantially as an entirety to any
Person, and the Company shall not permit any Person to consolidate with or merge into the Company or convey, transfer or lease
its properties and assets substantially as an entirety to the Company (provided, however, that for the
purposes of this Section 801, neither OSG International, Inc., a Marshall Islands corporation that is a subsidiary of the Company
(“OIN”), nor (i) any or all of OIN’s assets or OIN’s subsidiaries’ assets, (ii) any entity into which
OIN or its subsidiaries may be merged or converted or with which they may be consolidated, (iii) any entity resulting from any
merger, conversion or consolidation to which OIN or its subsidiaries may be a party, or (iv) any entity, that is not currently
owned directly or indirectly by the Company, that acquires OIN or any or all of the assets of OIN or any of its subsidiaries’
assets (provided in each case that OIN and the assets and entities described in (i) through (iv) above, collectively, may include
assets directly or indirectly transferred from OSG Bulk Ships, Inc. (“OBS”) to OIN and such other entities only to
the extent that such transfers would, to the extent applicable to such transfer, be permitted under each of Sections 6.09 (Transactions
with Affiliates), 6.08 (Dividends) and 6.04 (Investments, Loans and Advances) of each of the OBS ABL Facility and the OBS Term
Loan Facility, each as in effect on the date hereof), constitutes substantially an entirety of the Company’s assets)
unless:..”

 

ARTICLE THREE

 

GENERAL PROVISIONS

 

Section 301.Effectiveness. The provisions of this
Sixth Supplemental Indenture shall become effective immediately upon the execution and delivery by the Company and the Trustee
of this Sixth Supplemental Indenture; however, Section 201 of this Sixth Supplemental Indenture will not become operative until
the Company has delivered to the Trustee an Officers’ Certificate certifying that the amounts payable by the Company pursuant
to the terms of the Tender Offer and Consent Solicitation have been paid.

 

Section 302.Ratification of Indenture. The Indenture
is in all respects acknowledged, ratified and confirmed, and shall continue in full force and effect in accordance with the terms
thereof and as supplemented by this Sixth Supplemental Indenture. The Indenture and this Sixth Supplemental Indenture, shall be
read, taken and construed as one and the same instrument.

 

Section 303.Effect of Headings. The Article and Section
headings in this Sixth Supplemental Indenture are for convenience only and shall not affect the construction of this Sixth Supplemental
Indenture.

 

Section 304.Governing Law. THIS SIXTH SUPPLEMENTAL
INDENTURE SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAWS OF THE STATE OF NEW YORK.

 

Section 305.Multiple Counterparts. This Sixth 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.

 

Section 306.Successors and Assigns. All agreements
of the Company in this Sixth Supplemental Indenture shall bind its successors. All agreements of the Trustee in this Sixth Supplemental
Indenture shall bind its successors.

 

Section 307.Trustee Not Responsible for Recitals.
The recitals in this Sixth Supplemental Indenture are made by the Company, and the Trustee assumes no responsibility for the correctness
of such recitals.

 

    	 	3	 

     

    

 

IN WITNESS WHEREOF, the parties to this
Sixth Supplemental Indenture have caused the Sixth Supplemental Indenture to be duly executed as of day and year first above written.

 

	 	OVERSEAS SHIPHOLDING GROUP, INC.	 
	 	 	 	 
	 	 	 	 
	 	By 	/s/ Rick F. Oricchio	 
		Name:	Rick F. Oricchio	 
	 	Title: 	Senior Vice President, Chief Financial Officer	 
	 	 	 	 
	 	 	 	 
	 	 	 	 
	 	WILMINGTON TRUST COMPANY,

	 
	 	 	 	 
	 	as Trustee	 
	 	 	 	 
	 	 	 	 
	 	By 	/s/ W. Thomas Morris, II	 
	 	Name:	W. Thomas Morris, II

	 
	 	Title:	Vice President	 

 

 

    	 	4

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