Document:

Exhibit 4.3

 

Execution Version

 

 

OVERSEAS SHIPHOLDING GROUP, INC.

and

WILMINGTON TRUST COMPANY,

as Trustee

__________________________________________

 

SECOND SUPPLEMENTAL INDENTURE

Dated as of August 5, 2014

___________________________________________

 

 

7.50% Senior Notes I due 2021

 

    	 

    	 

    

   

 SECOND SUPPLEMENTAL
INDENTURE

 

THIS SECOND SUPPLEMENTAL INDENTURE, effective as of August 5,
2014 (the "Second 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") under and pursuant to the Indenture dated as of March 7, 2003, between the Company and the Trustee (the "Original
Indenture").

 

WHEREAS, Section 301 of the Original Indenture provides that
Securities may be issued under the Original Indenture in one or more series;

 

WHEREAS, Section 901 of the Original Indenture provides, among
other things, that the Company and the Trustee, at any time and from time to time, may enter into one or more supplemental indentures
to establish the form or terms of Securities of any series;

 

WHEREAS, the Company desires to create a new series of Securities
having the terms set forth in this Second Supplemental Indenture; and

 

WHEREAS, the Board of Directors of the Company has adopted resolutions
authorizing and approving the creation and issuance of $6,508,000 aggregate principal amount of 7.50% Senior Notes I due 2021 (the
"2014 Notes I"), and the Company and the Trustee are executing and delivering this Second Supplemental Indenture in order
to provide for the establishment of such Securities;

 

NOW, THEREFORE, for good and valuable consideration, the receipt
and sufficiency of which are hereby acknowledged, the parties to this Second Supplemental Indenture hereby agree as follows:

 

ARTICLE ONE

 

DEFINITIONS AND OTHER PROVISIONS OF GENERAL
APPLICATION

 

Section 101.Relation to Original Indenture. This
Second Supplemental Indenture constitutes an integral part of the Original 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):

 

"2014 Notes I" has the meaning set forth in the recitals
to this Second Supplemental Indenture.

 

    	 

    	 

    

 

"Designated Debt" means any debt for borrowed money
in the form of bonds, notes, debentures or other debt securities issued by way of a public offering or private placement, but excluding
loans made by banks and other financial institutions, customers and strategic partners.

 

"Original Indenture" has the meaning set forth in
the recitals to this Second Supplemental Indenture.

 

"Second Supplemental Indenture" means this instrument
as originally executed and as it may from time to time be supplemented or amended by one or more indentures supplement hereto entered
into pursuant to the applicable provisions hereof."

 

ARTICLE TWO

 

GENERAL TERMS AND CONDITIONS OF THE 2014
NOTES I

 

Section 201Designation and Principal Amount. There
is hereby authorized a series of Securities designated as 7.50% Senior Notes I due 2021 limited in aggregate principal amount to
$6,508,000. The 2014 Notes I may be issued from time to time upon written order of the Company for authentication and delivery
of the 2014 Notes I pursuant to Section 303 of the Original Indenture.

 

Section 202Maturity. The date upon which the 2014
Notes I will become due and payable at final maturity, together with any accrued and unpaid interest, is February 15, 2021.

 

Section 203Interest.

 

(a)    The 2014 Notes I will accrue interest at a rate of 7.50%
per annum from August 5, 2014, payable in cash on February 15 and August 15 in each year, commencing February 15, 2015 to the Person
in whose name the 2014 Note I (or one or more Predecessor Securities) is registered at the close of business on the Regular Record
Date for such interest, which shall be February 1 or August 1 (whether or not a Business Day), as the case may be, next preceding
such Interest Payment Date. Interest will be computed on the basis of a 360-day year comprised of twelve 30-day months. Any such
interest not so punctually paid or duly provided for will forthwith cease to be payable to the Holder on such Regular Record Date
and may either be paid to the Person in whose name the 2014 Note I (or one or more Predecessor Securities) 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 the 2014 Notes I not less than 10 days prior to such Special Record Date, or be paid at any time in
any other lawful manner not inconsistent with the requirements of any securities exchange on which the 2014 Notes I may be listed,
and upon such notice as may be required by such exchange.

 

(b)    Payment of the principal of (and premium, if any) and
interest on the 2014 Notes I will be made at the office or agency of the Company maintained for that purpose in the City of New
York, 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.

 

Section 204Redemption. The Company shall not be entitled
to redeem the 2014 Notes I prior to the maturity of the Notes.

 

Section 205Legal Defeasance and Covenant Defeasance.

 

    	 

    	 

    

 

(a)    Pursuant to Section 1302 of the Original Indenture, the
Company may, at its option and at any time, elect to have its obligations discharged with respect to the outstanding 2014 Notes
I.

 

(b)    Pursuant to Section 1303 of the Original Indenture, the
Company may, at its option and at any time, elect to have its obligations released with respect to certain covenants that are described
in the Original Indenture and thereafter any omission to comply with such obligations shall not constitute a Default or Event of
Default with respect to the 2014 Notes I.

 

Section 206Global Note. The 2014 Notes I shall be
issuable in one or more definitive Global Securities in book-entry form, which will be deposited by or on behalf of the Company,
through the facilities of The Depository Trust Company ("DTC") or its designated custodian. Every Global Security evidencing
all or part of the 2014 Notes I that is authenticated and delivered shall bear the legend set forth on the face of the form of
the 2014 Notes I attached as Exhibit A to this Second Supplemental Indenture.

 

Section 207Maintenance of Insurance. Section 1007
of the Original Indenture shall not apply to the 2014 Notes I.

 

Section 208Limitation on Liens. Section 1009 of the
Original Indenture as applied to the 2014 Notes I is hereby amended in its entirety to read as follows:

 

“The Company may not, directly or indirectly,
Incur, assume or suffer to exist any Mortgage on or with respect to any property or assets, now owned or hereafter acquired, to
secure any present or future Designated Debt without making effective provision for securing the 2014 Notes I: (1) in the event
such Designated Debt is pari passu with the 2014 Notes I, equally and ratably with such Designated Debt as to such property or
assets for so long as such Designated Debt will be so secured, or (2) in the event such Designated Debt is subordinate in right
of payment to the 2014 Notes I, prior to such Designated Debt as to such property or assets for so long as such Designated Debt
will be so secured."

 

Section 209Limitation on Sales and Leasebacks. Section
1010 of the Original Indenture shall not apply to the 2014 Notes I.

 

Section 210Limitation on Incurrence of Indebtedness by
Restricted Subsidiaries. Section 1011 of the Original Indenture shall not apply to the 2014 Notes I.

 

ARTICLE THREE

 

FORM OF THE 2014 NOTES I

 

Section 301.Form of the 2014 Notes I. The 2014 Notes
I and the Trustee's Certificate of Authentication to be endorsed thereon are to be substantially in the forms attached as Exhibit
A to this Second Supplemental Indenture, with such changes thereto as the officers of the Company executing the 2014 Notes
I (by manual or facsimile signature) may approve, such approval to be conclusively evidenced by their execution thereof.

 

    	 

    	 

    

 

ARTICLE FOUR

 

GENERAL PROVISIONS

 

Section 401.Effectiveness. The provisions of this
Second Supplemental Indenture shall become effective immediately upon the execution and delivery by the Trustee of this Second
Supplemental Indenture.

 

Section 402.Ratification of Indenture. The Original
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 Second Supplemental Indenture. The Original Indenture and this Second Supplemental
Indenture, shall be read, taken and construed as one and the same instrument.

 

Section 403.Effect of Headings. The Article and Section
headings in this Second Supplemental Indenture are for convenience only and shall not affect the construction of this Second Supplemental
Indenture.

 

Section 404.Governing Law. THIS SECOND SUPPLEMENTAL
INDENTURE SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAWS OF THE STATE OF NEW YORK.

 

Section 405.Multiple Counterparts. This Second 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 406.Successors and Assigns. All agreements
of the Company in this Second Supplemental Indenture shall bind its successors. All agreements of the Trustee in this Second Supplemental
Indenture shall bind its successors.

 

Section 407Trustee Not Responsible for Recitals.
The recitals in this Second Supplemental Indenture are made by the Company, and the Trustee assumes no responsibility for the correctness
of such recitals.

 

[Remainder of Page Left Blank Intentionally;
Signature Page Follows]

 

    	 

    	 

    

 

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

 

	 	OVERSEAS SHIPHOLDING GROUP, INC.
	 	 
	 	By /s/ Captain Ian T. Blackley
	 	Name: Captain Ian T. Blackley
	 	
        Title: Senior Vice
President, Chief Financial Officer and Treasurer

	 	 
	 	
         

        WILMINGTON TRUST COMPANY,

        

        as Trustee

	 	 
	 	By /s/ W. Thomas Morris, II
	 	Name: W. Thomas Morris, II
	 	Title: Vice President

 

    	 

    	 

    

  

EXHIBIT A

 

IF THIS SECURITY IS TO BE A GLOBAL SECURITY, INSERT:

 

THIS SECURITY IS A GLOBAL SECURITY WITHIN THE MEANING OF THE
INDENTURE HEREINAFTER REFERRED TO AND IS REGISTERED IN THE NAME OF A DEPOSITARY OR A NOMINEE THEREOF. THIS SECURITY MAY NOT BE
EXCHANGED IN WHOLE OR IN PART FOR A SECURITY REGISTERED, AND NO TRANSFER OF THIS SECURITY IN WHOLE OR IN PART MAY BE REGISTERED,
IN THE NAME OF ANY PERSON OTHER THAN SUCH DEPOSITARY OR A NOMINEE THEREOF, EXCEPT IN THE LIMITED CIRCUMSTANCES DESCRIBED IN THE
INDENTURE.

 

 

OVERSEAS SHIPHOLDING GROUP, INC.

 

7.50% Senior Notes I due 2021

 

	No. ___                                                                     	                                $_____________

 

Overseas Shipholding Group, Inc., a corporation duly organized
and existing under the laws of Delaware (herein called the "Company", which term includes any successor Person under
the Indenture hereinafter referred to), for value received, hereby promises to pay to _____________________________________, as
nominee for The Depository Trust Company (the "Holder"), or to its registered assigns, the principal sum of ___________________
Dollars on February 15, 2021, and to pay interest thereon from August 5, 2014 or from the most recent Interest Payment Date to
which interest has been paid or duly provided for, semi-annually on February 15 and August 15 in each year, commencing February
15, 2015, at the rate of 7.50% per annum, until the principal hereof is paid or made available for payment. This Security is issued
under an Indenture, dated as of March 7, 2003, as supplemented by the Second Supplemental Indenture dated as of August 5, 2014
(herein called the "Indenture" which term shall have the meaning assigned to it in such instrument), between the Company
and Wilmington Trust Company, as Trustee (herein called the "Trustee", which term includes any successor trustee under
the Indenture). The interest payable, and punctually paid or duly provided for, on any Interest Payment Date will, as provided
in such Indenture, be paid to the Person in whose name this Security (or one or more Predecessor Securities) is registered at the
close of business on the Regular Record Date for such interest, which shall be February 1 or August 1 (whether or not a Business
Day), as the case may be, next preceding such Interest Payment Date. Any such interest not so punctually paid or duly provided
for will 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 Security (or one or more Predecessor Securities) 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 Securities of this
series not less than 10 days prior to such Special Record Date, or be paid at any time in any other lawful manner not inconsistent
with the requirements of any securities exchange on which the Securities of this series may be listed, and upon such notice as
may be required by such exchange, all as more fully provided in the Indenture.

 

    	 

    	 

    

 

Payment by the Company of the principal of (and premium, if
any) and interest on this Security will be made at the office or agency of the Company maintained for that purpose in The City
of New York, 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.

 

Reference is hereby made to the further provisions of this Security
set forth on the reverse hereof, which further provisions shall for all purposes have the same effect as if set forth at this place.

 

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

 

In Witness Whereof, the Company has caused this instrument to
be duly executed under its corporate seal.

 

Dated as of ___________ ___, _____

           

 

	 	Overseas Shipholding Group, Inc.
	 	 
	 	By: 	_________________________
	 	 	 
	 	Name:	 
	 	 	 
	 	Title:	 

  

Attest:

______________________

                       
, Secretary

 

    	 

    	 

    

 

 TRUSTEE'S CERTIFICATE
OF AUTHENTICATION

 

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

 

                                                                    Wilmington
Trust Company,

 

                                                                     as
Trustee

 

	 	By:___________________________	 
	 	 	 
	 	Authorized Officer

 

    	 

    	 

    

 

FORM OF REVERSE OF SECURITY

 

This Security is one of a duly authorized issue of securities
of the Company (herein called the "Securities"), issued and to be issued in one or more series under the Indenture, and
reference is hereby made to the Indenture for a statement of the respective rights, limitations of rights, duties and immunities
thereunder of the Company, the Trustee and the Holders of the Securities and of the terms upon which the Securities are, and are
to be, authenticated and delivered. This Security is one of the series designated on the face hereof, limited in aggregate principal
amount to $6,508,000.

 

The Company shall not be entitled to redeem the Securities prior
to the maturity of the Securities.

 

If a Change of Control shall occur, Holders of the Securities
will have the right to require the Company to redeem such Holder's Securities, in whole or in part, in integral multiples of $1,000,
at a Redemption Price equal to 101.00% of the principal amount thereof and unpaid interest, if any, to the Redemption Date, all
as provided in the Indenture.

 

In the event of redemption of this Security in part only, a
new Security or Securities of this series and of like tenor for the unredeemed portion hereof will be issued in the name of the
Holder hereof upon the cancellation hereof.

 

The Indenture contains provisions for defeasance at any time
of the entire indebtedness of this Security or certain restrictive covenants and Events of Default with respect to this Security,
in each case upon compliance with certain conditions set forth in the Indenture.

 

If an Event of Default with respect to Securities of this series
shall occur and be continuing, the principal of the Securities of this series may be declared due and payable in the manner and
with the effect provided in the Indenture.

 

The Indenture permits, with certain exceptions as therein provided,
the amendment thereof and the modification of the rights and obligations of the Company and the rights of the Holders of the Securities
of each series to be affected under the Indenture at any time by the Company and the Trustee with the consent of the Holders of
66-2/3% in principal amount of the Securities at the time Outstanding of each series to be affected. The Indenture also contains
provisions permitting the Holders of specified percentages in principal amount of the Securities of each series at the time Outstanding,
on behalf of the Holders of all Securities of such series, to waive compliance by the Company 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 Security
shall be conclusive and binding upon such Holder and upon all future Holders of this Security and of any Security 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 Security.

 

As provided in and subject to the provisions of the Indenture,
the Holder of this Security 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 Securities of this series, the Holders of not less than 25% in principal
amount of the Securities of this series at the time Outstanding shall have made written request to the Trustee to institute proceedings
in respect of such Event of 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 Securities 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 Security for the enforcement of
any payment of principal hereof or any premium or interest hereon on or after the respective due dates expressed herein.

 

    	 

    	 

    

 

No reference herein to the Indenture and no provision of this
Security or of the Indenture shall alter or impair the obligation of the Company, which is absolute and unconditional, to pay the
principal of and any premium and interest on this Security 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 Security is registrable in the Security Register, upon surrender of this Security for registration
of transfer at the office or agency of the Company in any place where the principal of and any premium and interest on this Security
are 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 his attorney duly authorized in writing, and thereupon one or more new Securities
of this series and of like tenor, of authorized denominations and for the same aggregate principal amount, will be issued to the
designated transferee or transferees.

 

The Securities 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, Securities of this series are exchangeable for a like aggregate principal amount of Securities
of this series and of like tenor 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 Company 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 Security for registration of
transfer, the Company, the Trustee and any agent of the Company or the Trustee may treat the Person in whose name this Security
is registered as the owner hereof for all purposes, whether or not this Security be overdue, and neither the Company, the Trustee
nor any such agent shall be affected by notice to the contrary.

 

All terms used in this Security which are defined in the Indenture
shall have the meanings assigned to them in the Indenture.Exhibit 4.4

 

Execution Version

 

 

OVERSEAS SHIPHOLDING GROUP, INC.

and

WILMINGTON TRUST COMPANY,

as Trustee

__________________________________________

 

THIRD SUPPLEMENTAL INDENTURE

Dated as of August 5, 2014

___________________________________________

 

 

7.50% Senior Notes II due 2021

 

    	 

    	 

    

 

 THIRD SUPPLEMENTAL
INDENTURE

 

THIS THIRD SUPPLEMENTAL INDENTURE, effective as of August 5,
2014 (the "Third 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") under and pursuant to the Indenture dated as of March 7, 2003, between the Company and the Trustee (the "Original
Indenture").

 

WHEREAS, Section 301 of the Original Indenture provides that
Securities may be issued under the Original Indenture in one or more series;

 

WHEREAS, Section 901 of the Original Indenture provides, among
other things, that the Company and the Trustee, at any time and from time to time, may enter into one or more supplemental indentures
to establish the form or terms of Securities of any series;

 

WHEREAS, the Company desires to create a new series of Securities
having the terms set forth in this Third Supplemental Indenture; and

 

WHEREAS, the Board of Directors of the Company has
adopted resolutions authorizing and approving the creation and issuance of $138,708,000 aggregate principal amount of 7.50%
Senior Notes II due 2021 (the "2014 Notes II"), and the Company and the Trustee are executing and delivering this
Third Supplemental Indenture in order to provide for the establishment of such Securities;

 

NOW, THEREFORE, for good and valuable consideration, the receipt
and sufficiency of which are hereby acknowledged, the parties to this Third Supplemental Indenture hereby agree as follows:

 

ARTICLE ONE

 

DEFINITIONS AND OTHER PROVISIONS OF GENERAL
APPLICATION

 

Section 101.Relation to Original Indenture. This
Third Supplemental Indenture constitutes an integral part of the Original 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):

 

"2014 Notes II" has the meaning set forth in the recitals
to this Third Supplemental Indenture.

 

“Change of Control Triggering Event” means the occurrence
of a Change of Control and a Rating Decline.

 

    	 

    	 

    

 

"Designated Debt" means any debt for borrowed money
in the form of bonds, notes, debentures or other debt securities issued by way of a public offering or private placement, but excluding
loans made by banks and other financial institutions, customers and strategic partners.

 

“Gradation” means a gradation within a Rating Category
or a change to another Rating Category, which shall include: (a) “+” and “–” in the case of S&P’s
current Rating Categories (e.g., a decline from BB+ to BB would constitute a decrease of one gradation); (b) 1, 2 and 3
in the case of Moody’s current Rating Categories (e.g., a decline from B1 to B2 would constitute a decrease of one
gradation); or (c) the equivalent in respect of successor Rating Categories of S&P or Moody’s or Rating Categories used
by Rating Agencies other than S&P and Moody’s.

 

“Investment Grade” means: (1) BBB- or above in the
case of S&P (or its equivalent under any successor Rating Categories of S&P); (2) Baa3 or above, in the case of Moody’s
(or its equivalent under any successor Rating Categories of Moody’s); and (3) the equivalent in respect of the Rating Categories
of any

Rating Agencies substituted for S&P or Moody’s.

 

“Moody’s” means Moody’s Investors Service,
Inc.

 

"Original Indenture" has the meaning set forth in
the recitals to this Third Supplemental Indenture.

 

“Rating Agencies” means: (1)
S&P; (2) Moody’s; or (3) if either S&P or Moody’s or both of them are not making ratings of the 2014 Notes
II (or of the long term debt of the Company, if applicable) publicly available, a nationally recognized U.S. rating agency or agencies,
as the case may be, selected by the Company, which will be substituted for S&P or Moody’s or both, as the case may be.

 

“Rating Category” means: (1) with respect to S&P,
any of the following categories (any of which may include a “+” or “-”): AAA, AA, A, BBB, BB, B, CCC, CC,
C and D (or equivalent successor categories); (2) with respect to Moody’s, any of the following categories: Aaa, Aa, A, Baa,
Ba, B, Caa, Ca, C and D (or equivalent successor categories); and (3) the equivalent of any such categories of S&P or Moody’s
used by another Rating Agency, if applicable.

 

“Rating Decline” means that at any time within 90
days (which period shall be extended so long as the rating of the 2014 Notes II (or the long term debt of the Company, if the 2014
Notes II are not then rated) is under publicly announced consideration for possible downgrade by any Rating Agency) after the date
of public notice of a Change of Control, or of the intention of the Company or of any person to effect a Change of Control, the
rating of the 2014 Notes II (or the long term debt of the Company, if the 2014 Notes II are not then rated) is decreased by both
Rating Agencies by one or more Gradations and the rating by such Rating Agencies on the 2014 Notes II (or the long term debt of
the Company, if the 2014 Notes II are not then rated) following such downgrade is below Investment Grade.

 

"Third Supplemental Indenture" means this instrument
as originally executed and as it may from time to time be supplemented or amended by one or more indentures supplement hereto entered
into pursuant to the applicable provisions hereof."

 

“S&P” means Standard & Poor’s Rating
Services, a division of The McGraw-Hill Companies, Inc.

 

    	 

    	 

    

 

ARTICLE TWO

 

GENERAL TERMS AND CONDITIONS OF THE 2014
NOTES II

 

Section 201Designation and Principal Amount. There
is hereby authorized a series of Securities designated as 7.50% Senior Notes II due 2021 limited in aggregate principal amount
to $138,708,000. The 2014 Notes II may be issued from time to time upon written order of the Company for authentication and delivery
of the 2014 Notes II pursuant to Section 303 of the Original Indenture.

 

Section 202Maturity. The date upon which the 2014
Notes II will become due and payable at final maturity, together with any accrued and unpaid interest, is February 15, 2021.

 

Section 203Interest.

 

(a)     The 2014 Notes II will accrue interest at a rate of 7.50%
per annum from August 5, 2014, payable in cash on February 15 and August 15 in each year, commencing February 15, 2015 to the Person
in whose name the 2014 Note II (or one or more Predecessor Securities) is registered at the close of business on the Regular Record
Date for such interest, which shall be February 1 or August 1 (whether or not a Business Day), as the case may be, next preceding
such Interest Payment Date. Interest will be computed on the basis of a 360-day year comprised of twelve 30-day months. Any such
interest not so punctually paid or duly provided for will forthwith cease to be payable to the Holder on such Regular Record Date
and may either be paid to the Person in whose name the 2014 Note II (or one or more Predecessor Securities) 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 the 2014 Notes II not less than 10 days prior to such Special Record Date, or be paid at any time
in any other lawful manner not inconsistent with the requirements of any securities exchange on which the 2014 Notes II may be
listed, and upon such notice as may be required by such exchange.

 

(b)     Payment of the principal of (and premium, if any) and
interest on the 2014 Notes II will be made at the office or agency of the Company maintained for that purpose in the City of New
York, 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.

 

Section 204Redemption. The Company shall not be entitled
to redeem the 2014 Notes II prior to the maturity of the Notes.

 

Section 205Legal Defeasance and Covenant Defeasance.

 

(a)     Pursuant to Section 1302 of the Original Indenture, the
Company may, at its option and at any time, elect to have its obligations discharged with respect to the outstanding 2014 Notes
II.

 

(b)     Pursuant to Section 1303 of the Original Indenture, the
Company may, at its option and at any time, elect to have its obligations released with respect to certain covenants that are described
in the Original Indenture and thereafter any omission to comply with such obligations shall not constitute a Default or Event of
Default with respect to the 2014 Notes II.

 

    	 

    	 

    

 

Section 206Global Note. The 2014 Notes II shall be
issuable in one or more definitive Global Securities in book-entry form, which will be deposited by or on behalf of the Company,
through the facilities of The Depository Trust Company ("DTC") or its designated custodian. Every Global Security evidencing
all or part of the 2014 Notes II that is authenticated and delivered shall bear the legend set forth on the face of the form of
the 2014 Notes II attached as Exhibit A to this Third Supplemental Indenture.

 

Section 207Definitions. Section 101 of the Original
Indenture as applied to the 2014 Notes II is hereby modified as it applies to the 2014 Notes II by amending the definition of “Change
of Control” in its entirety to read as follows:

 

“Change of Control” means the occurrence
of either of the following events:

 

(1) a “person” or “group” (within
the meaning of Sections 13(d) and 14(d)(2) of the Exchange Act) becomes the ultimate “beneficial owner” (as defined
in Rule 13d-3 under the Exchange Act and including by reason of any change in the ultimate “beneficial ownership” of
the Capital Stock of the Company) of more than 50% of the total voting power of the Voting Stock of the Company (calculated on
a fully diluted basis); or

 

(2) individuals who at the beginning
of any period of two consecutive calendar years constituted the Board of Directors of the Company (together with any new directors
whose election by such Board of Directors or whose nomination for election was approved by a vote of at least two-thirds of the
members of such Board of Directors then still in office who either were members of such Board of Directors at the beginning of
such period or whose election or nomination for election was previously so approved) cease for any reason to constitute at least
50% of the members of such Board of Directors then in office.

 

Section 208Events of Default. Section 501(4) of the
Original Indenture as applied to the 2014 Notes II is hereby amended in its entirety to read as follows:

 

“(4)default in the payment of the principal
of (or any premium on) and any interest upon any Security required to be purchased upon the occurrence of a Change of Control Triggering
Event, when and as due by the terms of a Security of that Series; or”

 

Section 209Maintenance of Insurance. Section 1007
of the Original Indenture shall not apply to the 2014 Notes II.

 

Section 210Limitation on Liens. Section 1009 of the
Original Indenture as applied to the 2014 Notes II is hereby amended in its entirety to read as follows:

 

“The Company may not, directly or indirectly,
Incur, assume or suffer to exist any Mortgage on or with respect to any property or assets, now owned or hereafter acquired, to
secure any present or future Designated Debt without making effective provision for securing the 2014 Notes II: (1) in the event
such Designated Debt is pari passu with the 2014 Notes II, equally and ratably with such Designated Debt as to such property or
assets for so long as such Designated Debt will be so secured, or (2) in the event such Designated Debt is subordinate in right
of payment to the 2014 Notes II, prior to such Designated Debt as to such property or assets for so long as such Designated Debt
will be so secured."

 

    	 

    	 

    

 

Section 211Limitation on Sales and Leasebacks. Section
1010 of the Original Indenture shall not apply to the 2014 Notes II.

 

Section 212Limitation on Incurrence of Indebtedness by
Restricted Subsidiaries. Section 1011 of the Original Indenture shall not apply to the 2014 Notes II.

 

Section 213Offer to Repurchase Upon a Change of Control
Triggering Event. Section 1013 of the Original Indenture as applied to the 2014 Notes II is hereby amended in its entirety
to read as follows.

 

“SECTION 1013. OFFER TO REPURCHASE UPON A CHANGE
OF CONTROL TRIGGERING EVENT.

 

Upon the occurrence of a Change of Control Triggering
Event, each Holder shall have the right to require the Company to repurchase all or any part (equal to $1,000 or an integral multiple
thereof) of that Holder's Securities pursuant to the Change of Control Triggering Event offer on the terms set forth in this Indenture
(a "Change of Control Offer") at an offer price in cash equal to 101% of the aggregate principal amount of Securities
repurchased plus accrued and unpaid interest, if any, on the Securities repurchased to the date of purchase (the "Change of
Control Payment"). Within 30 days following any Change of Control Triggering Event, the Company shall mail a notice to each
Holder stating:

 

(1) the transaction or transactions
that constitute the Change of Control Triggering Event;

 

(2) that the Change of Control
Offer is being made pursuant to this Section 1013 and that all Securities tendered shall be accepted for payment;

 

(3) the purchase price and the
purchase date, which date shall be no earlier than 30 days and no later than 60 days from the date the notice is mailed (the "Change
of Control Payment Date");

 

(4) that any Security not tendered
or properly withdrawn shall continue to accrue interest;

 

(5) that, unless the Company defaults
in the payment of the Change of Control Payment, all Securities accepted for payment pursuant to the Change of Control Offer shall
cease to accrue interest after the Change of Control Payment Date;

 

(6) that Holders electing to have
any Securities purchased pursuant to a Change of Control Offer shall be required to surrender the Securities, together with such
form or forms as may be specified, to a Paying Agent at the address specified in the notice prior to the close of business on the
third Business Day preceding the Change of Control Payment Date;

 

(7) that Holders shall be entitled
to withdraw their election if the Paying Agent receives, not later than the close of business on the second Business Day preceding
the Change of Control Payment Date, a telegram, telex, facsimile transmission or letter setting forth the name of the Holder, the
principal amount of Securities delivered for purchase, and a statement that such Holder is withdrawing its election to have the
Securities purchased; and

 

    	 

    	 

    

 

(8) that Holders whose Securities
are being purchased only in part shall be issued new Securities equal in principal amount to the unpurchased portion of the Securities
surrendered, which unpurchased portion must be equal to $1,000 in principal amount or an integral multiple thereof.

 

On the Change of Control Payment Date, the Company shall,
to the extent lawful:

 

(1) accept for payment all Securities
or portions of Securities validly tendered and not properly withdrawn pursuant to the Change of Control Offer;

 

(2) deposit with the Paying Agent
an amount equal to the Change of Control Payment in respect of all Securities or portions of Securities properly tendered and not
properly withdrawn pursuant to the Change of Control Offer; and

 

(3) deliver or cause to be delivered
to the Trustee the Securities so accepted together with an Officers' Certificate stating the aggregate principal amount of Securities
or portions of Securities being purchased by the Company.

 

The Paying Agent shall promptly mail to each Holder
of Securities validly tendered and not properly withdrawn the Change of Control Payment for such Securities, and the Trustee shall
promptly authenticate and mail (or cause to be transferred by book entry) to each Holder a new Security equal in principal amount
to any unpurchased portion of the Securities surrendered, if any; provided that each new Security will be in a principal amount
of $1,000 or an integral multiple thereof.

 

The Company shall publicly announce the results of the
Change of Control Offer on or as soon as practicable after the Change of Control Payment Date.

 

The Company shall not be required to make a Change of
Control Offer upon a Change of Control Triggering Event if a third party makes the Change of Control Offer in the manner, at the
times and otherwise in compliance with the requirements set forth in this Indenture applicable to a Change of Control Offer made
by the Company and purchases all Securities validly tendered and not properly withdrawn under such Change of Control Offer.

 

The Company shall comply with the Requirements of Rule
14e-1 under the Exchange Act and any other securities laws and regulations thereunder to the extent those laws and regulations
are applicable in connection with the repurchase of the Securities as a result of a Change of Control Triggering Event. To the
extent that the provisions of any securities laws or regulations conflict with the Change of Control Triggering Event provisions
of this Indenture, the Company shall comply with the applicable securities laws and regulations and will not be deemed to have
breached its obligations under this Section 1013 by virtue of such conflict.”

 

    	 

    	 

    

 

ARTICLE THREE

 

FORM OF THE 2014 NOTES II

 

Section 301.Form of the 2014 Notes II. The 2014 Notes
II and the Trustee's Certificate of Authentication to be endorsed thereon are to be substantially in the forms attached as Exhibit
A to this Third Supplemental Indenture, with such changes thereto as the officers of the Company executing the 2014 Notes II
(by manual or facsimile signature) may approve, such approval to be conclusively evidenced by their execution thereof.

 

ARTICLE FOUR

 

GENERAL PROVISIONS

 

Section 401.Effectiveness. The provisions of this
Third Supplemental Indenture shall become effective immediately upon the execution and delivery by the Trustee of this Third Supplemental
Indenture.

 

Section 402.Ratification of Indenture. The Original
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 Third Supplemental Indenture. The Original Indenture and this Third Supplemental
Indenture, shall be read, taken and construed as one and the same instrument.

 

Section 403.Effect of Headings. The Article and Section
headings in this Third Supplemental Indenture are for convenience only and shall not affect the construction of this Third Supplemental
Indenture.

 

Section 404.Governing Law. THIS THIRD SUPPLEMENTAL
INDENTURE SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAWS OF THE STATE OF NEW YORK.

 

Section 405.Multiple Counterparts. This Third 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 406.Successors and Assigns. All agreements
of the Company in this Third Supplemental Indenture shall bind its successors. All agreements of the Trustee in this Third Supplemental
Indenture shall bind its successors.

 

Section 407Trustee Not Responsible for Recitals.
The recitals in this Third Supplemental Indenture are made by the Company, and the Trustee assumes no responsibility for the correctness
of such recitals.

 

[Remainder of Page Left Blank Intentionally;
Signature Page Follows] 

 

    	 

    	 

    

  

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

 

	 	OVERSEAS SHIPHOLDING GROUP, INC.
	 	 
	 	By /s/ Captain Ian T. Blackley
	 	Name: Captain Ian T. Blackley
	 	
        Title:    Senior Vice
President, Chief Financial Officer and Treasurer

	 	 
	 	
         

        WILMINGTON TRUST COMPANY,

        

        as Trustee

	 	 
	 	By /s/ W. Thomas Morris, II
	 	Name: W. Thomas Morris, II
	 	Title: Vice President

 

    	 

    	 

    

   

EXHIBIT A

 

IF THIS SECURITY IS TO BE A GLOBAL SECURITY, INSERT:

 

THIS SECURITY IS A GLOBAL SECURITY WITHIN THE MEANING OF THE
INDENTURE HEREINAFTER REFERRED TO AND IS REGISTERED IN THE NAME OF A DEPOSITARY OR A NOMINEE THEREOF. THIS SECURITY MAY NOT BE
EXCHANGED IN WHOLE OR IN PART FOR A SECURITY REGISTERED, AND NO TRANSFER OF THIS SECURITY IN WHOLE OR IN PART MAY BE REGISTERED,
IN THE NAME OF ANY PERSON OTHER THAN SUCH DEPOSITARY OR A NOMINEE THEREOF, EXCEPT IN THE LIMITED CIRCUMSTANCES DESCRIBED IN THE
INDENTURE.

 

 

OVERSEAS SHIPHOLDING GROUP, INC.

 

7.50% Senior Notes II due 2021

 

	No. ___                                                         	                                            $_____________

 

Overseas Shipholding Group, Inc., a corporation duly organized
and existing under the laws of Delaware (herein called the "Company", which term includes any successor Person under
the Indenture hereinafter referred to), for value received, hereby promises to pay to _____________________________________, as
nominee for The Depository Trust Company (the "Holder"), or to its registered assigns, the principal sum of ___________________
Dollars on February 15, 2021, and to pay interest thereon from August 5, 2014 or from the most recent Interest Payment Date to
which interest has been paid or duly provided for, semi-annually on February 15 and August 15 in each year, commencing February
15, 2015, at the rate of 7.50% per annum, until the principal hereof is paid or made available for payment. This Security is issued
under an Indenture, dated as of March 7, 2003, as supplemented by the Third Supplemental Indenture dated as of August 5, 2014 (herein
called the "Indenture" which term shall have the meaning assigned to it in such instrument), between the Company and
Wilmington Trust Company, as Trustee (herein called the "Trustee", which term includes any successor trustee under the
Indenture). The interest payable, and punctually paid or duly provided for, on any Interest Payment Date will, as provided in such
Indenture, be paid to the Person in whose name this Security (or one or more Predecessor Securities) is registered at the close
of business on the Regular Record Date for such interest, which shall be February 1 or August 1 (whether or not a Business Day),
as the case may be, next preceding such Interest Payment Date. Any such interest not so punctually paid or duly provided for will
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
Security (or one or more Predecessor Securities) 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 Securities of this series not
less than 10 days prior to such Special Record Date, or be paid at any time in any other lawful manner not inconsistent with the
requirements of any securities exchange on which the Securities of this series may be listed, and upon such notice as may be required
by such exchange, all as more fully provided in the Indenture.

 

    	 

    	 

    

 

Payment by the Company of the principal of (and premium, if
any) and interest on this Security will be made at the office or agency of the Company maintained for that purpose in The City
of New York, 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.

 

Reference is hereby made to the further provisions of this Security
set forth on the reverse hereof, which further provisions shall for all purposes have the same effect as if set forth at this place.

 

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

 

In Witness Whereof, the Company has caused this instrument to
be duly executed under its corporate seal.

 

Dated as of ___________ ___, _____

                                                                           

	 	Overseas Shipholding Group, Inc.
	 	 
	 	By:	 
	 	 	 
	 	 	Name:
	 	 	 
	 	 	Title:

 

Attest:

______________________

                       
, Secretary

 

    	 

    	 

    

  

 TRUSTEE'S CERTIFICATE
OF AUTHENTICATION

 

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

                                                           

	 	Wilmington Trust Company,
	 	 
	 	as Trustee	 
	 	 	 
	 	By:	 
	 	 	 
	 	Authorized Officer

 

    	 

    	 

    

   

FORM OF REVERSE OF SECURITY

 

This Security is one of a duly authorized issue of securities
of the Company (herein called the "Securities"), issued and to be issued in one or more series under the Indenture, and
reference is hereby made to the Indenture for a statement of the respective rights, limitations of rights, duties and immunities
thereunder of the Company, the Trustee and the Holders of the Securities and of the terms upon which the Securities are, and are
to be, authenticated and delivered. This Security is one of the series designated on the face hereof, limited in aggregate principal
amount to $138,708,000.

 

The Company shall not be entitled to redeem the Securities prior
to the maturity of the Securities.

 

If a Change of Control Triggering Event shall occur, Holders
of the Securities will have the right to require the Company to redeem such Holder's Securities, in whole or in part, in integral
multiples of $1,000, at a Redemption Price equal to 101.00% of the principal amount thereof and unpaid interest, if any, to the
Redemption Date, all as provided in the Indenture.

 

In the event of redemption of this Security in part only, a
new Security or Securities of this series and of like tenor for the unredeemed portion hereof will be issued in the name of the
Holder hereof upon the cancellation hereof.

 

The Indenture contains provisions for defeasance at any time
of the entire indebtedness of this Security or certain restrictive covenants and Events of Default with respect to this Security,
in each case upon compliance with certain conditions set forth in the Indenture.

 

If an Event of Default with respect to Securities of this series
shall occur and be continuing, the principal of the Securities of this series may be declared due and payable in the manner and
with the effect provided in the Indenture.

 

The Indenture permits, with certain exceptions as therein provided,
the amendment thereof and the modification of the rights and obligations of the Company and the rights of the Holders of the Securities
of each series to be affected under the Indenture at any time by the Company and the Trustee with the consent of the Holders of
66-2/3% in principal amount of the Securities at the time Outstanding of each series to be affected. The Indenture also contains
provisions permitting the Holders of specified percentages in principal amount of the Securities of each series at the time Outstanding,
on behalf of the Holders of all Securities of such series, to waive compliance by the Company 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 Security
shall be conclusive and binding upon such Holder and upon all future Holders of this Security and of any Security 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 Security.

 

As provided in and subject to the provisions of the Indenture,
the Holder of this Security 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 Securities of this series, the Holders of not less than 25% in principal
amount of the Securities of this series at the time Outstanding shall have made written request to the Trustee to institute proceedings
in respect of such Event of 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 Securities 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 Security for the enforcement of
any payment of principal hereof or any premium or interest hereon on or after the respective due dates expressed herein.

 

    	 

    	 

    

 

No reference herein to the Indenture and no provision of this
Security or of the Indenture shall alter or impair the obligation of the Company, which is absolute and unconditional, to pay the
principal of and any premium and interest on this Security 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 Security is registrable in the Security Register, upon surrender of this Security for registration
of transfer at the office or agency of the Company in any place where the principal of and any premium and interest on this Security
are 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 his attorney duly authorized in writing, and thereupon one or more new Securities
of this series and of like tenor, of authorized denominations and for the same aggregate principal amount, will be issued to the
designated transferee or transferees.

 

The Securities 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, Securities of this series are exchangeable for a like aggregate principal amount of Securities
of this series and of like tenor 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 Company 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 Security for registration of
transfer, the Company, the Trustee and any agent of the Company or the Trustee may treat the Person in whose name this Security
is registered as the owner hereof for all purposes, whether or not this Security be overdue, and neither the Company, the Trustee
nor any such agent shall be affected by notice to the contrary.

 

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

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