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LETTER OF TRANSMITTAL  

Regarding the Offer to Exchange All Outstanding

8.250% Senior Notes Due March 15, 2013

In Exchange For

Registered 8.250% Senior Notes Due March 15, 2013

of  

 OVERSEAS SHIPHOLDING GROUP, INC.  

CUSIP NO. 690368 AE5      

         THE EXCHANGE OFFER WILL EXPIRE AT 5:00 P.M., NEW YORK CITY TIME, ON

JUNE            , 2003, UNLESS EXTENDED (THE "EXPIRATION DATE").  

 NOTES TENDERED IN SUCH EXCHANGE OFFER MAY BE WITHDRAWN AT ANY TIME

PRIOR TO 5:00 P.M., NEW YORK CITY TIME, ON THE EXPIRATION DATE.  

The Exchange Agent is:  

WILMINGTON TRUST COMPANY 

YOU
CAN DELIVER THIS LETTER OF TRANSMITTAL AND ANY OTHER REQUIRED

DOCUMENTATION TO THE EXCHANGE AGENT AT THE ADDRESSES AS FOLLOWS: 

	By Hand Delivery:
 Wilmington Trust Company

301 West 11th Street

Wilmington, Delaware 19801	 	By Overnight Courier:
 Wilmington Trust Company

1100 North Market Street

Rodney Square North

Wilmington, Delaware 19890-1615
	
By First Class Mail:
 Wilmington Trust Company

1100 North Market Street

Rodney Square North

Wilmington, Delaware 19890-1615	
 	
To Confirm Receipt of

Notice of Guaranteed Delivery:
 Fax #: (302) 636-4145

Fax Confirmation #: (302) 636-6472

DELIVERY OF THIS INSTRUMENT TO AN ADDRESS OTHER THAN AS SET FORTH ABOVE

WILL NOT CONSTITUTE A VALID DELIVERY. THE INSTRUCTIONS ACCOMPANYING

THIS LETTER OF TRANSMITTAL SHOULD BE READ CAREFULLY BEFORE

THE LETTER OF TRANSMITTAL IS COMPLETED.  

        The undersigned hereby acknowledges receipt and review of the prospectus dated May     , 2003, of Overseas Shipholding Group, Inc. (the
"Company") and this letter of transmittal. These two documents together constitute the Company's offer to exchange its 8.250% Senior Notes due March 15, 2013 (the "Exchange Notes"), the
issuance of which has been registered under the Securities Act of 1933, as amended (the "Securities Act"), for a like principal amount of its issued and outstanding 8.250% Senior Notes due
March 15, 2013 (the "Original Notes") (the "Exchange Offer"). 

        The
Company reserves the right, at any time or from time to time, to extend the period of time during which the Exchange Offer for the Original Notes is open, at its discretion, in which
event the term "Expiration Date" shall mean the latest date to which such Exchange Offer is extended. The Company shall notify Wilmington Trust Company (the "Exchange Agent") of any extension by oral
or 

 

written notice and shall make a public announcement thereof no later than 9:00 a.m., New York City time, on the next business day after the previously scheduled Expiration Date. 

        This
letter of transmittal is to be used by a holder of Original Notes (i) if certificates of Original Notes are to be forwarded herewith or (ii) if delivery of Original
Notes is to be made by book-entry transfer to the account maintained by the Exchange Agent at The Depository Trust Company ("DTC") pursuant to the procedures set forth in the prospectus
under the caption "The Exchange Offer—Book-Entry Transfer" and an "agent's message" is not delivered as described in the prospectus under the caption "The Exchange
Offer—Tendering Through DTC's Automated Tender Offer Program." Tenders by book-entry transfer may also be made by delivering an agent's message in lieu of this letter of
transmittal. Holders of Original Notes whose Original Notes are not immediately available, or who are unable to deliver their Original Notes, this letter of transmittal and all other documents
required hereby to the Exchange Agent on or prior to the Expiration Date for the Exchange Offer, or who are unable to complete the procedure for book-entry transfer on a timely basis, must
tender their Original Notes according to the guaranteed delivery procedures set forth in the prospectus under the caption "The Exchange Offer—Guaranteed Delivery Procedures" by the
Expiration Date. See Instruction 2. DELIVERY OF DOCUMENTS TO DTC DOES NOT CONSTITUTE DELIVERY TO THE EXCHANGE AGENT. 

        The
term "holder" with respect to the Exchange Offer for Original Notes means any person in whose name such Original Notes are registered on the books of the Company, any person who
holds such Original Notes and has obtained a properly completed bond power from the registered holder or any participant in the DTC system whose name appears on a security position listing as the
holder of such Original Notes and who desires to deliver such Original Notes by book-entry transfer at DTC. The undersigned has completed, executed and delivered this letter of transmittal
to indicate the action the undersigned desires to take with respect to such Exchange Offer. Holders who wish to tender their Original Notes must complete this letter of transmittal in its entirety
(unless such Original Notes are to be tendered by book-entry transfer and an agent's message is delivered in lieu hereof). 

PLEASE
READ THE ENTIRE LETTER OF TRANSMITTAL AND THE PROSPECTUS CAREFULLY BEFORE CHECKING ANY BOX BELOW. 

        THE
INSTRUCTIONS INCLUDED WITH THIS LETTER OF TRANSMITTAL MUST BE FOLLOWED. QUESTIONS AND REQUESTS FOR ASSISTANCE OR FOR ADDITIONAL COPIES OF THE PROSPECTUS AND THIS LETTER OF
TRANSMITTAL MAY BE DIRECTED TO THE EXCHANGE AGENT. 

2

 

        List
below the Original Notes to which this letter of transmittal relates. If the space below is inadequate, list the registered numbers and principal amounts on a separate signed
schedule and affix the list to this letter of transmittal. 

	

	DESCRIPTION OF ORIGINAL NOTES TENDERED

	

	Name(s) and Address(es) of Registered Holder(s)

Exactly as Name(s) appear(s) on Original Notes

(Please fill in, if blank)
 
	 	Registered

Number(s)*
 
	 	Aggregate Principal

Amount Represented

By Note(s)
 
	 	Aggregate

Principal Amount

Tendered**
 

	

	

	

	

	

	

	

 	
 	
 TOTAL	
 	

 	
 	

 
	

	*
	Need
not be completed by book-entry holders.

	**
	Unless
otherwise indicated, any tendering holder of Original Notes will be deemed to have tendered the entire aggregate principal amount represented by such Original Notes. All tenders
must be in integral multiples of $1,000.

	/
	/    CHECK
HERE IF TENDERED ORIGINAL NOTES ARE ENCLOSED HEREWITH.

	/
	/    CHECK
HERE AND COMPLETE THE FOLLOWING IF TENDERED ORIGINAL NOTES ARE BEING DELIVERED BY BOOK-ENTRY TRANSFER MADE TO THE ACCOUNT MAINTAINED BY THE EXCHANGE AGENT
WITH DTC (FOR USE BY ELIGIBLE INSTITUTIONS ONLY): 

        Name
of Tendering Institution:   

        DTC
Account Number(s):   

        Transaction
Code Number(s):   

	/
	/    CHECK
HERE AND COMPLETE THE FOLLOWING IF TENDERED ORIGINAL NOTES ARE BEING DELIVERED PURSUANT TO A NOTICE OF GUARANTEED DELIVERY EITHER ENCLOSED HEREWITH OR PREVIOUSLY
DELIVERED TO THE EXCHANGE AGENT (COPY ATTACHED) (FOR USE BY ELIGIBLE INSTITUTIONS ONLY): 

        Name(s)
of Registered holder(s) of Original Notes:   

        Date
of Execution of Notice of Guaranteed Delivery:   

        Window
Ticket Number (if available):   

        Name
of Eligible Institution that Guaranteed Delivery:   

        DTC
Account Number(s) (if delivered by book-entry transfer):   

        Transaction
Code Number(s) (if delivered by book-entry transfer):   

        Name
of Tendering Institution (if delivered by book-entry transfer):   

3

 

	/
	/    CHECK
HERE AND COMPLETE THE FOLLOWING IF YOU ARE A BROKER-DEALER AND WISH TO RECEIVE 10 ADDITIONAL COPIES OF THE PROSPECTUS AND 10 COPIES OF ANY AMENDMENTS OR SUPPLEMENTS
THERETO: 

	Name:	 	

	

Address:	
 	

	

        If
the undersigned is not a broker-dealer, the undersigned represents that it is not engaged in, and does not intend to engage in, a distribution of Exchange Notes. If the undersigned is
a broker-dealer that will receive Exchange Notes for its own account in exchange for Original Notes that were acquired as a result of market-making activities or other trading activities, it
acknowledges that it will deliver a prospectus in connection with any resale of such Exchange Notes; however, by so acknowledging and by delivering a prospectus, the undersigned will not be deemed to
admit that it is an "underwriter" within the meaning of the Securities Act. 

SIGNATURES MUST BE PROVIDED BELOW. PLEASE READ

THE ACCOMPANYING INSTRUCTIONS CAREFULLY  

        Subject to the terms and conditions of the Exchange Offer, the undersigned hereby tenders to the Company for exchange the principal amount of Original Notes
indicated above. Subject to and effective upon the acceptance for exchange of the principal amount of Original Notes tendered in accordance with this letter of transmittal, the undersigned hereby
exchanges, assigns and transfers to, or upon the order of, the Company all right, title and interest in and to such Original Notes tendered for exchange hereby. The undersigned hereby irrevocably
constitutes and appoints the Exchange Agent the true and lawful agent and attorney-in-fact for the undersigned (with full knowledge that said Exchange Agent also acts as the
agent for the Company in connection with the Exchange Offer) with respect to the tendered Original Notes with full power of substitution to (i) deliver such Original Notes, or transfer
ownership of such Original Notes on the account books maintained by DTC, to the Company and deliver all
accompanying evidences of transfer and authenticity, and (ii) present such Original Notes for transfer on the books of the Company and receive all benefits and otherwise exercise all rights of
beneficial ownership of such Original Notes, all in accordance with the terms of the Exchange Offer. The power of attorney granted in this paragraph shall be deemed to be irrevocable and coupled with
an interest. 

        The
undersigned hereby represents and warrants that the undersigned has full power and authority to tender, exchange, assign and transfer the Original Notes tendered hereby and to
acquire the Exchange Notes issuable upon the exchange of such tendered Original Notes, and that the Company will acquire good and unencumbered title thereto, free and clear of all liens, restrictions,
charges and encumbrances and not subject to any adverse claim, when the same are accepted for exchange by the Company. 

        The
undersigned acknowledges that the Exchange Offer is being made in reliance upon interpretations set forth in no-action letters issued to third parties (the "Prior
No-Action Letters") by the staff of the Securities and Exchange Commission (the "SEC") that the Exchange Notes issued in exchange for the Original Notes pursuant to the Exchange Offer may
be offered for resale, resold and otherwise transferred by holders thereof (other than any such holder that is an "affiliate" of the Company within the meaning of Rule 405 under the Securities
Act), without compliance with the registration and prospectus delivery provisions of the Securities Act, PROVIDED that such Exchange Notes are acquired in the ordinary course of such holders' business
and such holders are not engaging in, do not intend to engage in and have no arrangement or understanding with any person to 

4

 

participate in a distribution of such Exchange Notes. The SEC has not, however, considered the Exchange Offer in the context of a no-action letter, and there can be no assurance that the
staff of the SEC would make a similar determination with respect to the Exchange Offer as in other circumstances. 

        The
undersigned hereby further represents to the Company that (i) any Exchange Notes received are being acquired in the ordinary course of business of the person receiving such
Exchange Notes, whether or not the undersigned, (ii) neither the undersigned nor any such other person has an arrangement or understanding with any person to participate in the distribution of
the Original Notes or the Exchange Notes within the meaning of the Securities Act and (iii) neither the holder nor any such other person is an "affiliate," as defined in Rule 405 under
the Securities Act, of the Company or, if it is such an affiliate, it will comply with the registration and prospectus delivery requirements of the Securities Act to the extent applicable. 

        If
the undersigned is not a broker-dealer, the undersigned represents that it is not engaged in, and does not intend to engage in, a distribution of Exchange Notes. If the undersigned is
a broker-dealer that will receive Exchange Notes for its own account in exchange for Original Notes that were acquired as a result of market-making activities or other trading activities, it
acknowledges that it will deliver a prospectus in connection with any resale of such Exchange Notes; however, by so acknowledging and by delivering a prospectus, the undersigned will not be deemed to
admit that it is an "underwriter" within the meaning of the Securities Act. The undersigned acknowledges that if the undersigned is tendering Original Notes in the Exchange Offer with the intention of
participating in any manner in a distribution of the Exchange Notes (i) the undersigned cannot rely on the position of the staff of the SEC set forth in the Prior No-Action Letters
and, in the absence of an exemption therefrom, must comply with the
registration and prospectus delivery requirements of the Securities Act in connection with a secondary resale transaction of the Exchange Notes, in which case the registration statement must contain
the selling security holder information required by Item 507 or Item 508, as applicable, of Regulation S-K of the SEC, and (ii) failure to comply with such requirements in
such instance could result in the undersigned incurring liability under the Securities Act for which the undersigned is not indemnified by the Company. 

        The
undersigned will, upon request, execute and deliver any additional documents deemed by the Exchange Agent or the Company to be necessary or desirable to complete the exchange,
assignment and transfer of the Original Notes tendered hereby, including the transfer of such Original Notes on the account books maintained by DTC. 

        For
purposes of the Exchange Offer, the Company shall be deemed to have accepted for exchange validly tendered Original Notes when, as and if the Company gives oral or written notice
thereof to the Exchange Agent. Any tendered Original Notes that are not accepted for exchange pursuant to such Exchange Offer for any reason will be returned, without expense, to the undersigned as
promptly as practicable after the Expiration Date for such Exchange Offer. 

        All
authority conferred or agreed to be conferred by this letter of transmittal shall survive the death, incapacity or dissolution of the undersigned, and every obligation of the
undersigned under this letter of transmittal shall be binding upon the undersigned's successors, assigns, heirs, executors, administrators, trustees in bankruptcy and legal representatives. 

        The
undersigned acknowledges that the Company's acceptance of properly tendered Original Notes pursuant to the procedures described under the caption "The Exchange
Offer—Procedures for Tendering" in the prospectus and in the instructions hereto will constitute a binding agreement between the undersigned and the Company upon the terms and subject to
the conditions of the Exchange Offer. 

        The
Exchange Offer is subject to certain conditions set forth in the prospectus under the caption "The Exchange Offer—Conditions To The Exchange Offer." The undersigned
recognizes that as a 

5

 

result of these conditions (which may be waived, in whole or in part, by the Company), the Company may not be required to exchange any of the Original Notes tendered hereby. 

        Unless
otherwise indicated under "Special Issuance Instructions," please issue the Exchange Notes issued in exchange for the Original Notes accepted for exchange, and return any Original
Notes not tendered or not exchanged, in the name(s) of the undersigned (or, in the case of a book-entry delivery of Original Notes, please credit the account indicated above maintained at
DTC). Similarly, unless otherwise indicated under "Special Delivery Instructions," please mail or deliver the Exchange Notes issued in exchange for the Original Notes accepted for exchange and any
Original Notes not tendered
or not exchanged (and accompanying documents, as appropriate) to the undersigned at the address shown below the undersigned's signature(s). In the event that both "Special Issuance Instructions" and
"Special Delivery Instructions" are completed, please issue the Exchange Notes issued in exchange for the Original Notes accepted for exchange in the name(s) of, and return any Original Notes not
tendered or not exchanged to, the person(s) (or account(s)) so indicated. The undersigned recognizes that the Company has no obligation pursuant to the "Special Issuance Instructions" and "Special
Delivery Instructions" to transfer any Original Notes from the name of the registered holder(s) thereof if the Company does not accept for exchange any of the Original Notes so tendered for exchange. 

6

 

SPECIAL ISSUANCE INSTRUCTIONS

(See Instructions 5 and 6)  

        To be completed ONLY (i) if Original Notes in a principal amount not tendered, or Exchange Notes issued in exchange for Original Notes accepted for
exchange, are to be issued in the name of someone other than the undersigned, or (ii) if Original Notes tendered by book-entry transfer which are not exchanged are to be returned by
credit to an account maintained at DTC other than the DTC Account Number set forth above. Issue Exchange Notes and/or Original Notes to: 

	Name:	 	

	PLEASE TYPE OR PRINT
	Address:	 	

	

(Include Zip Code)

Taxpayer Identification or Social Security Number:
	

 
	

 PLEASE TYPE OR PRINT

SPECIAL DELIVERY INSTRUCTIONS

(See Instructions 5 and 6)  

        To be completed ONLY if Original Notes in a principal amount not tendered, or Exchange Notes issued in exchange for Original Notes accepted for exchange, are to
be mailed or delivered to someone other than the undersigned, or to the undersigned at an address other than that shown below the undersigned's signature. Mail or deliver Exchange Notes and/or
Original Notes to: 

	Name:	 	

	PLEASE TYPE OR PRINT
	Address:	 	

	

(Include Zip Code)

Taxpayer Identification or Social Security Number:
	

	PLEASE TYPE OR PRINT
	

/ /    Credit unexchanged Original Notes delivered by book-entry transfer to DTC set forth below:
	
DTC Account Number:
	

7

 

IMPORTANT

PLEASE SIGN HERE WHETHER OR NOT ORIGINAL NOTES

ARE BEING PHYSICALLY TENDERED HEREBY

(COMPLETE ACCOMPANYING SUBSTITUTE FORM W-9 BELOW)  

(Signature(s) of Registered Holder(s) of Original Notes)

	Dated	 	 	 	, 2003	 
	 	 	
	 	 	 

        (The
above lines must be signed by the registered holder(s) of Original Notes as your name(s) appear(s) on the Original Notes or on a security position listing, or by person(s)
authorized to become registered holder(s) by a properly completed bond power from the registered holder(s), a copy of which must be transmitted with this letter of transmittal. If Original Notes to
which this letter of transmittal relate are held of record by two or more joint holders, then all such holders must sign this letter of transmittal. If signature is by a trustee, executor,
administrator, guardian, attorney-in-fact, officer of a corporation or other person acting in a fiduciary or representative capacity, then such person must (i) set forth
his or her full title below and (ii) unless waived by the Company, submit evidence satisfactory to the Company of such person's authority so to act. See Instruction 5 regarding the completion
of this letter of transmittal, printed below.) 

	

Name(s):	
 	

    
(Please Type or Print)                
	Capacity:	 	    

	Address:	 	    

	
(Include Zip Code)

	Area Code and Telephone Number:	 	

	Taxpayer Identification or Social Security Number:	 	

SIGNATURE GUARANTEE

(IF REQUIRED BY INSTRUCTION 5)

Certain signatures must be guaranteed by an Eligible Institution.  

Signature(s) Guaranteed by an Eligible Institution: 

Authorized
Signature   

Title 
 

Name
of Firm   

Address,
Include Zip Code   

 

Area
Code and Telephone Number   

	Dated	 	 	, 2003
	 	 	
	 

8

  

 
 

INSTRUCTIONS
  
    FORMING PART OF THE TERMS AND CONDITIONS OF THE EXCHANGE OFFER    
    

        1.    DELIVERY OF THIS LETTER OF TRANSMITTAL AND ORIGINAL NOTES OR AGENT'S MESSAGE AND BOOK-ENTRY CONFIRMATIONS. All physically delivered
Original Notes or any confirmation of a book-entry transfer to the Exchange Agent's account at DTC of Original Notes tendered by book-entry transfer (a "Book-Entry
Confirmation"), as well as a properly completed and duly executed copy of this letter of transmittal or facsimile hereof (or an agent's message in lieu hereof), and any other documents required by
this letter of transmittal, must be received by the Exchange Agent at its address set forth herein prior to 5:00 p.m., New York City time, on the Expiration Date for the Exchange Offer, or the
tendering holder must comply with the guaranteed delivery procedures set forth below. THE METHOD OF DELIVERY OF THE TENDERED ORIGINAL NOTES, THIS LETTER OF TRANSMITTAL AND ALL OTHER REQUIRED DOCUMENTS
TO THE EXCHANGE AGENT IS AT THE ELECTION AND RISK OF THE HOLDER AND, EXCEPT AS OTHERWISE PROVIDED BELOW, THE DELIVERY WILL BE DEEMED MADE ONLY WHEN ACTUALLY RECEIVED OR CONFIRMED BY THE EXCHANGE
AGENT. INSTEAD OF DELIVERY BY MAIL, IT IS RECOMMENDED THAT THE HOLDER USE AN OVERNIGHT OR HAND DELIVERY SERVICE. IN ALL CASES, SUFFICIENT TIME SHOULD BE ALLOWED TO ASSURE DELIVERY TO THE EXCHANGE
AGENT BEFORE THE EXPIRATION DATE. NO LETTER OF TRANSMITTAL OR ORIGINAL NOTES SHOULD BE SENT TO THE COMPANY. 

        2.    GUARANTEED
DELIVERY PROCEDURES. Holders who wish to tender their Original Notes and (a) whose Original Notes are not immediately available, (b) who cannot
deliver their Original Notes, this letter of transmittal or any other documents required hereby to the Exchange Agent prior to the applicable Expiration Date or (c) who are unable to comply
with the applicable procedures under the DTC's Automated Tender Offer Program on a timely basis, must tender their Original Notes according to the guaranteed delivery procedures set forth in the
prospectus. Pursuant to such procedures: (i) such tender must be made by or through a firm which is a member of a registered national securities exchange or of the National Association of
Securities Dealers, Inc., a commercial bank or a trust company having an office or correspondent in the United States or an "eligible guarantor institution" within the meaning of
Rule 17Ad-15 under the Securities Exchange Act of 1934, as amended (an "Eligible Institution"); (ii) prior to the applicable Expiration Date, the Exchange Agent must have
received from the Eligible Institution a properly completed and duly executed notice of guaranteed delivery (by facsimile transmission, mail or hand delivery) or a properly transmitted agent's message
and notice of guaranteed delivery setting forth the name and address of the holder of the Original Notes, the registration number(s) of such Original Notes and the total principal amount of Original
Notes tendered, stating that the tender is being made thereby and guaranteeing that, within three New York Stock Exchange trading days after such Expiration Date, this letter of transmittal (or
facsimile hereof or an agent's message in lieu hereof) together with the Original Notes in proper form for transfer (or a Book-Entry Confirmation) and any other documents required hereby,
will be deposited by the Eligible Institution with the Exchange Agent; and (iii) this letter of transmittal (or facsimile hereof or an agent's message in lieu hereof) together with the
certificates for all physically tendered Original Notes in proper form for transfer (or Book-Entry Confirmation, as the case may be) and all other documents required hereby are received by
the Exchange Agent within three New York Stock Exchange trading days after such Expiration Date. 

        Any
holder of Original Notes who wishes to tender Original Notes pursuant to the guaranteed delivery procedures described above must ensure that the Exchange Agent receives the notice of
guaranteed delivery prior to 5:00 p.m., New York City time, on the applicable Expiration Date. Upon request of the Exchange Agent, a notice of guaranteed delivery will be sent to holders who
wish to tender their Original Notes according to the guaranteed delivery procedures set forth above. 

        See
"The Exchange Offer—Guaranteed Delivery Procedures" section of the prospectus. 

9

 

        3.    TENDER
BY HOLDER. Only a holder of Original Notes may tender such Original Notes in the Exchange Offer. Any beneficial holder of Original Notes who is not the registered
holder and who wishes to tender should arrange with the registered holder to execute and deliver this letter of transmittal on his behalf or must, prior to completing and executing this letter of
transmittal and delivering his Original Notes, either make appropriate arrangements to register ownership of the Original Notes in such holder's name or obtain a properly completed bond power from the
registered holder. 

        4.    PARTIAL
TENDERS. Tenders of Original Notes will be accepted only in integral multiples of $1,000. If less than the entire principal amount of any Original Notes is
tendered, the tendering holder should fill in the principal amount tendered in the fourth column of the box entitled "Description of Original Notes Tendered" above. The entire principal amount of
Original Notes delivered to the Exchange Agent will be deemed to have been tendered unless otherwise indicated. If the entire principal amount of all Original Notes is not tendered, then Original
Notes for the principal amount of Original Notes not tendered and Exchange Notes issued in exchange for any Original Notes accepted will be returned to the holder as promptly as practicable after the
Original Notes are accepted for exchange. 

        5.    SIGNATURES
ON THIS LETTER OF TRANSMITTAL; BOND POWERS AND ENDORSEMENTS; GUARANTEE OF SIGNATURES. If this letter of transmittal (or facsimile hereof) is signed by the
registered holder(s) of the Original Notes tendered hereby, the signature(s) must correspond exactly with the name(s) as written on the face of the Original Notes without alteration, enlargement or
any change whatsoever. If this letter of transmittal (or facsimile hereof) is
signed by a participant in DTC, the signature must correspond with the name as it appears on the security position listing as the holder of the Original Notes. 

        If
this letter of transmittal (or facsimile hereof) is signed by the registered holder(s) of Original Notes listed and tendered hereby and the Exchange Notes issued in exchange therefor
are to be issued (or any untendered principal amount of Original Notes is to be reissued) to the registered holder(s), the said holder(s) need not and should not endorse any tendered Original Notes,
nor provide a separate bond power. In any other case, such holder(s) must either properly endorse the Original Notes tendered or transmit a properly completed separate bond power with this letter of
transmittal, with the signatures on the endorsement or bond power guaranteed by an Eligible Institution. 

        If
this letter of transmittal (or facsimile hereof) or any Original Notes or bond powers are signed by trustees, executors, administrators, guardians,
attorneys-in-fact, officers of corporations or others acting in a fiduciary or representative capacity, such persons should so indicate when signing, and, unless waived by the
Company, evidence satisfactory to the Company of their authority to act must be submitted with this letter of transmittal. 

        NO
SIGNATURE GUARANTEE IS REQUIRED IF (i) THIS LETTER OF TRANSMITTAL (OR FACSIMILE HEREOF) IS SIGNED BY THE REGISTERED HOLDER(S) OF THE ORIGINAL NOTES TENDERED HEREIN (OR BY A
PARTICIPANT IN DTC WHOSE NAME APPEARS ON A SECURITY POSITION LISTING AS THE OWNER OF THE TENDERED ORIGINAL NOTES) AND THE EXCHANGE NOTES ARE TO BE ISSUED DIRECTLY TO SUCH REGISTERED HOLDER(S) (OR, IF
SIGNED BY A PARTICIPANT IN DTC, DEPOSITED TO SUCH PARTICIPANT'S ACCOUNT AT DTC) AND NEITHER THE BOX ENTITLED "SPECIAL DELIVERY INSTRUCTIONS" NOR THE BOX ENTITLED "SPECIAL ISSUANCE INSTRUCTIONS" HAS
BEEN COMPLETED, OR (ii) SUCH ORIGINAL NOTES ARE TENDERED FOR THE ACCOUNT OF AN ELIGIBLE INSTITUTION. IN ALL OTHER CASES, ALL SIGNATURES ON THIS LETTER OF TRANSMITTAL (OR FACSIMILE HEREOF) MUST
BE GUARANTEED BY AN ELIGIBLE INSTITUTION. 

        6.    SPECIAL
ISSUANCE AND DELIVERY INSTRUCTIONS. Tendering holders should indicate, in the applicable box or boxes, the name and address to which Exchange Notes or substitute
Original Notes for principal amounts not tendered or not accepted for exchange are to be issued or sent, if different from the name and address of the person signing this letter of transmittal. In the
case 

10

 

of
issuance in a different name, the taxpayer identification or social security number of the person named must also be indicated. Holders tendering Original Notes by book-entry transfer
may request that Original Notes not exchanged be credited to such account maintained at DTC as such noteholder may designate hereon. If no such instructions are given, such Original Notes not
exchanged will be returned to the name and address (or account number) of the person signing this letter of transmittal. 

        7.    TRANSFER
TAXES. The Company will pay all transfer taxes, if any, applicable to the exchange of Original Notes pursuant to the Exchange Offer. If, however, Exchange Notes
or Original Notes for principal amounts not tendered or accepted for exchange are to be delivered to, or are to be registered or issued in the name of, any person other than the registered holder of
the Original Notes tendered hereby, or if tendered Original Notes are registered in the name of any person other than the person signing this letter of transmittal, or if a transfer tax is imposed for
any reason other than the exchange of Original Notes pursuant to the Exchange Offer, then the amount of any such transfer taxes (whether imposed on the registered holder or any other persons) will be
payable by the tendering holder. If satisfactory evidence of payment of such taxes or exemption therefrom is not submitted with this letter of transmittal, the amount of such transfer taxes will be
billed directly to such tendering holder and the Exchange Agent will retain possession of an amount of Exchange Notes with a face amount at least equal to the amount of such transfer taxes due by such
tendering holder pending receipt by the Exchange Agent of the amount of such taxes. 

        8.    TAX
IDENTIFICATION NUMBER. To prevent backup withholding, each tendering holder must provide the Company with its correct taxpayer identification number ("TIN") as
instructed in this section 8 and under "Form W-9 Guidelines" below. The Company reserves the right in its sole discretion to take whatever steps are necessary to comply with
the Company's obligations regarding backup withholding. 

        Certain
foreign individuals and entities will not be subject to backup withholding or information reporting if they submit a Form W-8BEN, signed under penalties of
perjury, attesting to their foreign status. A Form W-8BEN can be obtained from the Exchange Agent. 

        By
requesting the information described in this section 8 and the section "W-9 Guidelines" below, the Company is hereby notifying each holder or beneficial owner that
to the extent that the holder or beneficial owner is able to comply without undue hardship, the certification, identification and reporting requirements described herein are required under the law of
the United States as a precondition to exemption from all or part of the tax due. 

        9.    VALIDITY
OF TENDERS. All questions as to the validity, form, eligibility, time of receipt, acceptance and withdrawal of tendered Original Notes will be determined by the
Company in its sole discretion, which determination will be final and binding. The Company reserves the absolute right to reject any and all Original Notes not properly tendered or any Original Notes
the Company's acceptance of which might, in the opinion of the Company's counsel, be unlawful. The Company also reserves the absolute right to waive any conditions of the Exchange Offer or defects or
irregularities of tenders as to particular Original Notes. The Company's interpretation of the terms and conditions of the Exchange Offer (including this letter of transmittal and the instructions
hereto) shall be final and binding on all parties. Unless waived, any defects or irregularities in connection with tenders of Original Notes must be cured within such time as the Company shall
determine. Neither the Company, the Exchange Agent nor any other person shall be under any duty to give notification of defects or irregularities with respect to tenders of Original Notes nor shall
any of them incur any liability for failure to give such notification. 

        10.    WAIVER
OF CONDITIONS. The Company reserves the absolute right to waive, in whole or part, any of the conditions to the Exchange Offer set forth in the prospectus. 

        11.    NO
CONDITIONAL TENDER. No alternative, conditional, irregular or contingent tender of Original Notes will be accepted. 

11

 

        12.    MUTILATED,
LOST, STOLEN OR DESTROYED ORIGINAL NOTES. Any holder whose Original Notes have been mutilated, lost, stolen or destroyed should contact the Exchange Agent at
the address indicated above for further instructions. This letter of transmittal and related documents cannot be processed until the procedures for replacing lost, stolen or destroyed Original Notes
have been followed. 

        13.    REQUESTS
FOR ASSISTANCE OR ADDITIONAL COPIES. Requests for assistance or for additional copies of the prospectus or this letter of transmittal may be directed to the
Exchange Agent at the address set forth on the cover page of this letter of transmittal. Holders may also contact their broker, dealer, commercial bank, trust company or other nominee for assistance
concerning the Exchange Offer. 

        14.    WITHDRAWAL.
Tenders may be withdrawn only pursuant to the limited withdrawal rights set forth in the prospectus under the caption "The Exchange
Offer—Withdrawal of Tenders." 

        IMPORTANT:
THIS LETTER OF TRANSMITTAL OR A MANUALLY SIGNED FACSIMILE HEREOF OR AN AGENT'S MESSAGE IN LIEU HEREOF (TOGETHER WITH THE ORIGINAL NOTES DELIVERED BY BOOK-ENTRY
TRANSFER OR IN ORIGINAL HARD COPY FORM) MUST BE RECEIVED BY THE EXCHANGE AGENT, OR THE NOTICE OF GUARANTEED DELIVERY MUST BE RECEIVED BY THE EXCHANGE AGENT, PRIOR TO 5:00 P.M., NEW YORK CITY
TIME, ON THE EXPIRATION DATE. 

 
 

FORM W-9 GUIDELINES    
    

        A holder of any Original Notes or Exchange Notes must provide the Company (as payor) with its correct taxpayer identification number ("TIN"), which, in the case
of a holder who is an individual is
his or her social security number. If the Company is not provided with the correct TIN, the holder may be subject to a $50 penalty imposed by the Internal Revenue Service and backup withholding of 30%
on interest payments on the Exchange Notes. 

        To
prevent backup withholding, each tendering holder must provide such holder's correct TIN by completing the Substitute Form W-9 set forth herein, certifying that the
TIN provided is correct (or that such holder is awaiting a TIN), and that (i) the holder has not been notified by the Internal Revenue Service that such holder is subject to backup withholding
as a result of failure to report all interest or dividends or (ii) the Internal Revenue Service has notified the holder that such holder is no longer subject to backup withholding. If the
Exchange Notes will be registered in more than one name or will not be in the name of the actual owner, consult the instructions on Internal Revenue Service Form W-9, which may be
obtained from the Exchange Agent, for information on which TIN to report. 

        If
such holder does not have a TIN, such holder should consult the instructions on Form W-9 concerning applying for a TIN, check the box in Part 3 of the
Substitute Form W-9, write "applied for" in lieu of its TIN and sign and date the form and the Certificate of Awaiting Taxpayer Identification Number. Checking this box, writing
"applied for" on the form and signing such certificate means that such holder has already applied for a TIN or that such holder intends to apply for one in the near future. If such holder does not
provide its TIN to the Company within 60 days, backup withholding will begin and continue until such holder furnishes its TIN to the Company. 

        Backup
withholding is not an additional Federal income tax. Rather, the amount of such tax withheld will be credited against the Federal income tax liability of persons subject to backup
withholding. If backup withholding results in an overpayment of taxes, a refund may be obtained from the Internal Revenue Service. 

 
 

IMPORTANT TAX INFORMATION    
    

        WHAT TAXPAYER IDENTIFICATION NUMBER TO GIVE THE EXCHANGE AGENT. The registered holder or transferee(s), if any, is required to give the Exchange Agent the social
security number or taxpayer identification number of the holder of the Note(s). 

12

 

	

	
SUBSTITUTE
 FORM W-9
 Department of the Treasury

Internal Revenue Service	
 	
Part I: PLEASE PROVIDE YOUR TIN IN THE BOX AT RIGHT AND CERTIFY BY SIGNING AND DATING BELOW

Social security number(s)

OR ________________________

Employer Identification Number

(if awaiting TIN write "Applied For")

	
Payer's Request for Taxpayer

Identification Number (TIN)

and Certification	 	Part II—For Payees exempt from backup withholding, see the enclosed Guidelines for Certification of Taxpayer Identification Number on Substitute Form W-9 and complete as instructed therein.

	 	 	Part III: Awaiting TIN    / /
	

	Certification. Under penalties of perjury, I certify that:
	

(1) The Number shown on this form is my correct Taxpayer Identification Number (or I am waiting for a number to be issued to me),
	

(2) I am not subject to backup withholding either because: (a) I am exempt from backup withholding, or (b) I have not been notified by the Internal Revenue Service (IRS) that I am subject to backup withholding as a result of a failure to
report all interest or dividends, or (c) the IRS has notified me that I am no longer subject to backup withholding and
	

(3) I am a U.S. person (including a U.S. resident alien).
	
Certificate Instructions. You must cross out item (2) above if you have been notified by the IRS that you are subject to backup withholding because you have failed to report
all interest or dividends on your tax return. However, if after being notified by the IRS that you were subject to backup withholding you received another notification from the IRS that you are no longer subject to backup withholding, do not cross
out item (2). (Also see instructions in the enclosed Guidelines.)
	

 	
 	

 	
 	

 
	Signature 	 	Date   
	

	
NOTE:	
 	

FAILURE TO COMPLETE AND RETURN THIS FORM MAY RESULT IN BACKUP WITHHOLDING OF 30% OF ANY PAYMENT MADE TO YOU IN RESPECT OF THE NOTES. PLEASE REVIEW THE FOREGOING GUIDELINES FOR CERTIFICATION OF TAXPAYER IDENTIFICATION NUMBER ON SUBSTITUTE FORM W-9 FOR
ADDITIONAL DETAILS. YOU MUST COMPLETE THE FOLLOWING CERTIFICATE IF YOU ARE AWAITING YOUR TIN.

CERTIFICATE OF AWAITING TAXPAYER IDENTIFICATION  

             I certify under penalties of perjury that a TIN has not been issued to me, and either (a) I have mailed or delivered an
application to receive a TIN to
the appropriate IRS Center or Social Security Administration Office or (b) I intend to mail or deliver such an application in the near future. I understand that if I do not provide a TIN by the
time of payment, all reportable payments made to me thereafter will be subject to a 30% backup withholding tax. 

	Signature	 	    
	 	Date	 	    
	 

13

QuickLinks

INSTRUCTIONS FORMING PART OF THE TERMS AND CONDITIONS OF THE EXCHANGE OFFER

FORM W-9 GUIDELINES

IMPORTANT TAX INFORMATIONQuickLinks
 -- Click here to rapidly navigate through this document

 
 

NOTICE OF GUARANTEED DELIVERY
  
    FOR TENDER OF ALL OUTSTANDING
  8.250% SENIOR NOTES DUE MARCH 15, 2013
  IN EXCHANGE FOR
  REGISTERED 8.250% SENIOR NOTES DUE MARCH 15, 2013
  OF
  
    OVERSEAS
SHIPHOLDING GROUP, INC.    
  

CUSIP NO. 690368 AE5  

        This
form, or one substantially equivalent hereto, must be used by a holder to accept the Exchange Offer of Overseas Shipholding Group, Inc. (the "Company") and to tender 8.250%
Senior Notes due March 15, 2013 (the "Original Notes") to the Exchange Agent pursuant to the guaranteed delivery procedures described in "The Exchange Offer—Guaranteed Delivery
Procedures" of the Company's prospectus dated May    , 2003 and in Instruction 2 to the related Letter of Transmittal. Any holder who wishes to tender Original Notes pursuant to such
guaranteed delivery procedures must ensure that Wilmington Trust Company, as exchange agent (the "Exchange Agent"), receives this notice of guaranteed delivery, properly completed and duly executed,
prior to the Expiration Date (as defined below) of the Exchange Offer for such series. Capitalized terms used but not defined herein have the meanings ascribed to them in the Letter of Transmittal. 

        THE
EXCHANGE OFFER WILL EXPIRE AT 5:00 P.M., NEW YORK CITY TIME, ON JUNE    , 2003, UNLESS EXTENDED (THE "EXPIRATION DATE"). NOTES TENDERED IN SUCH EXCHANGE OFFER MAY
BE WITHDRAWN AT ANY TIME PRIOR TO 5:00 P.M., NEW YORK CITY TIME, ON THE EXPIRATION DATE. 

THE
EXCHANGE AGENT FOR THE EXCHANGE OFFER IS:

WILMINGTON TRUST COMPANY

YOU CAN DELIVER THIS NOTICE OF GUARANTEED DELIVERY

TO THE EXCHANGE AGENT

AT THE ADDRESSES AS FOLLOWS: 

	

 	
 	

 
	BY HAND DELIVERY:

WILMINGTON TRUST COMPANY

301 WEST 11th STREET

WILMINGTON, DELAWARE 19801	 	BY OVERNIGHT COURIER:

WILMINGTON TRUST COMPANY

1100 NORTH MARKET STREET

RODNEY SQUARE NORTH

WILMINGTON, DELAWARE 19890-1615
	

BY FIRST CLASS MAIL:

WILMINGTON TRUST COMPANY

1100 NORTH MARKET STREET

RODNEY SQUARE NORTH

WILMINGTON, DELAWARE 19890-1615	
 	

TO CONFIRM RECEIPT OF NOTICE OF

GUARANTEED DELIVERY:

FAX #: (302) 636-4145

FAX CONFIRMATION #: (302) 636-6472

 

        DELIVERY OF THIS INSTRUMENT TO AN ADDRESS OTHER THAN AS SET FORTH ABOVE WILL NOT CONSTITUTE A VALID DELIVERY. THE INSTRUCTIONS ACCOMPANYING THIS NOTICE OF
GUARANTEED DELIVERY SHOULD BE READ CAREFULLY BEFORE THE NOTICE OF GUARANTEED DELIVERY IS COMPLETED. 

        This
notice of guaranteed delivery is not to be used to guarantee signatures. If a signature on a Letter of Transmittal is required to be guaranteed by an "Eligible Institution" under
the instructions thereto, such signature guarantee must appear in the applicable space in the box provided on the Letter of Transmittal for guarantee of signatures. 

Ladies
and Gentlemen: 

        The
undersigned hereby tenders to the Company, in accordance with the Company's offer, upon the terms and subject to the conditions set forth in the prospectus and the related Letter of
Transmittal, receipt of which is hereby acknowledged, the principal amount of Original Notes set forth below pursuant to the guaranteed delivery procedures set forth in the prospectus under the
caption "The Exchange Offer—Guaranteed Delivery Procedures" and in Instruction 2 of the Letter of Transmittal. 

        The
undersigned hereby tenders the Original Notes listed below: 

------------------------------------------------------------------------------------------------------------------------------------------

	

Certificate Number(s)

(if known) of Original Notes or

Account Number at the DTC
	
 	

Aggregate Principal

Amount Represented
	
 	

Aggregate Principal

Amount Tendered*

2

  

 
 

PLEASE SIGN AND COMPLETE    
  

	Names of Record Holder(s):	 	Signature(s):	 	 
	
	 	
	 	 
	
	 	
	 	 
	

Address:	 	 	 	 
	
	 	 
	
	 	 
	(Include Zip Code)	 	 
	

Area Code and Telephone Number:	 	 
	
	 	 
	

Dated:  
 , 2003	 	 

	*
	Unless
otherwise indicated, any tendering holder of Original Notes will be deemed to have tendered the entire aggregate principal amount represented by such Original Notes. All tenders
must be in integral multiples of $1,000. 

	

	

        THIS
NOTICE OF GUARANTEED DELIVERY MUST BE SIGNED BY THE REGISTERED HOLDER(S) OF ORIGINAL NOTES EXACTLY AS THE NAME(S) OF SUCH PERSON(S) APPEAR(S) ON CERTIFICATES FOR ORIGINAL NOTES OR
ON A SECURITY POSITION LISTING AS THE OWNER OF ORIGINAL NOTES, OR BY PERSON(S) AUTHORIZED TO BECOME HOLDER(S) BY ENDORSEMENTS AND DOCUMENTS TRANSMITTED WITH THIS NOTICE OF GUARANTEED DELIVERY. IF
SIGNATURE IS BY A TRUSTEE, EXECUTOR, ADMINISTRATOR, GUARDIAN, ATTORNEY-IN-FACT, OFFICER OR OTHER PERSON ACTING IN A FIDUCIARY OR REPRESENTATIVE CAPACITY, SUCH PERSON MUST
PROVIDE THE FOLLOWING INFORMATION: 

PLEASE
PRINT NAME(S) AND ADDRESS(ES) 

	
	 	 
	

Name(s):	 	 	 	 
	
	 	 
	

Capacity:	 	 	 	 
	
	 	 

3

 

Address(es):

 

 

 

 
 

GUARANTEE
  (Not to be used for signature guarantee)    
  

        The undersigned, a firm which is a member of a registered national securities exchange or of the National Association of Securities Dealers, Inc., a
commercial bank or a trust company having an office or correspondent in the United States, or an "eligible guarantor institution" within the meaning of Rule 17Ad-15 under the
Securities Exchange Act of 1934, hereby guarantees deposit with the Exchange Agent of the Letter of Transmittal (or facsimile thereof or agent's message in lieu thereof), together with the Original
Notes of the series tendered hereby in proper form for transfer (or confirmation of the book-entry transfer of such Original Notes into the Exchange Agent's account at the DTC described in
the prospectus under the caption "The Exchange Offer—Book-Entry Transfer" and in the Letter of Transmittal) and any other required documents, all by 5:00 p.m., New York
City time, within three New York Stock Exchange trading days following the Expiration Date for such series. 

	

Name of Firm:	
 	

 
	

	
 	

	 	 	(AUTHORIZED SIGNATURE)
	

Address:	
 	

Name:
	

	
 	

	

	
 	

Title:
	(INCLUDE ZIP CODE)	 	 
	

 	
 	

	 	 	(PLEASE TYPE OR PRINT)
	

Area Code and Telephone Number:	
 	

 
	

	
 	

Date:  , 2003

4

  

        DO NOT SEND ORIGINAL NOTES WITH THIS FORM. ACTUAL SURRENDER OF ORIGINAL NOTES MUST BE MADE PURSUANT TO, AND BE ACCOMPANIED BY, A PROPERLY COMPLETED AND DULY EXECUTED LETTER OF
TRANSMITTAL AND ANY OTHER REQUIRED DOCUMENTS. 

 
 

INSTRUCTIONS FOR NOTICE OF GUARANTEED DELIVERY    
  

        1.    DELIVERY
OF THIS NOTICE OF GUARANTEED DELIVERY. A properly completed and duly executed copy of this notice of guaranteed delivery (or facsimile hereof or an agent's
message and notice of guaranteed delivery in lieu hereof) and any other documents required by this notice of guaranteed delivery with respect to the Original Notes must be received by the Exchange
Agent at its address set forth herein prior to the Expiration Date of the Exchange Offer. Delivery of such notice of guaranteed delivery may be made by facsimile transmission, mail or hand delivery.
THE METHOD OF DELIVERY OF THIS NOTICE OF GUARANTEED DELIVERY AND ANY OTHER REQUIRED DOCUMENTS TO THE EXCHANGE AGENT IS AT THE ELECTION AND SOLE RISK OF THE HOLDER, AND THE DELIVERY WILL BE DEEMED MADE
ONLY WHEN ACTUALLY RECEIVED BY THE EXCHANGE AGENT. If delivery is by mail, registered mail with return receipt requested, properly insured, is recommended. As an alternative to delivery by mail, the
holders may wish to consider using an overnight or hand delivery service. In all cases, sufficient time should be allowed to assure timely delivery. For a description of the guaranteed delivery
procedures, see Instruction 2 of the Letter of Transmittal. 

        2.    SIGNATURES
ON THIS NOTICE OF GUARANTEED DELIVERY. If this notice of guaranteed delivery (or facsimile hereof) is signed by the registered holder(s) of the Original Notes
referred to herein, the signature(s) must correspond exactly with the name(s) as written on the face of the Original Notes without alteration, enlargement or any change whatsoever. If this notice of
guaranteed delivery (or facsimile hereof) is signed by a DTC participant whose name appears on a security position listing as the owner of the Original Notes, the signature must correspond with the
name as it appears on the security position listing as the owner of the Original Notes. 

        If
this notice of guaranteed delivery (or facsimile hereof) is signed by a person other than the registered holder(s) of any Original Notes listed or a DTC participant, this notice of
guaranteed
delivery must be accompanied by appropriate bond powers, signed as the name(s) of the registered holder(s) appear(s) on the Original Notes or signed as the name(s) of the participant appears on DTC's
security position listing. 

        If
this notice of guaranteed delivery (or facsimile hereof) is signed by a trustee, executor, administrator, guardian, attorney-in-fact, officer of a corporation
or other person acting in a fiduciary or representative capacity, such person should so indicate when signing and submit herewith evidence satisfactory to the Exchange Agent of such person's authority
to so act. 

        3.    REQUESTS
FOR ASSISTANCE OR ADDITIONAL COPIES. Questions and requests for assistance and requests for additional copies of the prospectus and this notice of guaranteed
delivery may be directed to the Exchange Agent at the address set forth on the cover page hereof. Holders may also contact their broker, dealer, commercial bank, trust company or other nominee for
assistance concerning the Exchange Offer. 

5

QuickLinks

NOTICE OF GUARANTEED DELIVERY FOR TENDER OF ALL OUTSTANDING 8.250% SENIOR NOTES DUE MARCH 15, 2013 IN EXCHANGE FOR REGISTERED 8.250% SENIOR NOTES DUE MARCH 15, 2013 OF OVERSEAS SHIPHOLDING GROUP,
INC.

PLEASE SIGN AND COMPLETE

GUARANTEE (Not to be used for signature guarantee)

INSTRUCTIONS FOR NOTICE OF GUARANTEED DELIVERY

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