AS FILED WITH THE

Registration No. 333-

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION ON JUNE 15, 2001

Registration No. 333-62702

SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

AMENDMENT NO. 1

TO

FORM S-3

REGISTRATION STATEMENT

UNDER

THE SECURITIES ACT OF 1933

OVERSEAS SHIPHOLDING GROUP, INC.

(Exact Namename of Registrantregistrant as Specifiedspecified in its Charter)charter)

(Address, Including Zip Code, and Telephone Number, Including Area Code, of Registrant's Principal Executive Offices)

Robert N. Cowen
511 Fifth600 Third Avenue,
39^th Floor

New York, New York 10017
212-953-410010016

(212) 953-4100

(Name, Address, Including Zip Code,including zip code, and Telephone Number, Including Area Code,telephone number,
including area code, of Agent for Service)registrant’s principal executive offices)

Copies to:

Approximate date of commencement of proposed sale to the public: As soon as practicableFrom time to time after the effective date of this Registration Statement.

If the only securities being registered on this form are being offered pursuant to dividend or interest reinvestment plans, please check the following box./ /¨

If any of the securities being registered on this formForm are to be offered on a delayed or continuous basis pursuant to Rule 415 under the Securities Act of 1933, other than securities offered only in connection with dividend or interest reinvestment plans, check the following box./ /x

If this formForm is filed to register additional securities for an offering pursuant to Rule 462(b) under the Securities Act, please check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering./ /¨

If this formForm is a post-effective amendment filed pursuant to Rule 462(c) under the Securities Act, please check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering./ /¨

If delivery ofthis Form is a registration statement pursuant to General Instruction I.D. or a post-effective amendment thereto that shall become effective upon filing with the prospectus is expected to be madeCommission pursuant to Rule 434, please462(e) under the Securities Act, check the following box./ /¨

If this Form is a post-effective amendment to a registration statement filed pursuant to General Instruction I.D. filed to register additional securities or additional classes of securities pursuant to Rule 413(b) under the Securities Act, check the following box.¨

CALCULATION OF REGISTRATION FEE

The registrant hereby amends this registration statement on such date or dates as may be necessary to delay its effective date until the Registrantregistrant shall file a further amendment which specifically states that this registration statement shall thereafter become effective in accordance with Section 8(a) of the Securities Act of 1933 or until the registration statement shall become effective on such date as the Securities and Exchange Commission, acting pursuant to said Section 8(a), may determine.

The information in this preliminary prospectus is not complete and may be changed. These securitiesThe selling securityholders may not be soldsell these securities until the registration statement filed with the Securities and Exchange Commission relating to these securities is effective. This preliminary prospectus is not an offer to sell nor doesthese securities and it seekis not a solicitation of an offer to buy these securities in any jurisdiction where thesuch offer, solicitation or sale is not permitted.

Subject to Completion. Dated June 15, 2001.

5,000,000 SharesSUBJECT TO COMPLETION, DATED AUGUST 9, 2016

PROSPECTUS

Overseas Shipholding Group, Inc.

33,350,136 Shares of Class A Common Stock

 All

17,719,598 Class A Warrants, Each to Purchase 0.190 Shares of Class A Common Stock

This prospectus relates to the shares of common stock in the offering are being soldresale from time to time by the selling stockholderssecurityholders identified in this prospectus. Overseas Shipholding Group, Inc.prospectus of up to (i) 33,350,136 shares of our Class A Common Stock, par value $0.01 per share, and (ii) 17,719,598 Class A Warrants, each to purchase 0.190 shares of our Class A Common Stock (subject to adjustment as described herein). The Class A Warrants have a per share exercise price of $0.01 and expire on August 5, 2039.

We are not offering any securities for sale under this prospectus, and we will not receive any of the proceeds from the sale or other disposition of the shares.securities covered hereby.

The common stockselling securityholders may offer the securities from time to time directly or through underwriters, broker-dealers or agents and in one or more public or private transactions and at fixed prices, prevailing market prices, at prices relating to prevailing market prices or at negotiated prices, or otherwise. If the securities are sold through underwriters, broker-dealers or agents, the selling securityholders will be responsible for underwriting discounts or commissions or agents’ commissions. See “Plan of Distribution” for additional information.

Our Class A Common Stock is listed on the New York Stock Exchange under the symbol "OSG."“OSG.” The last reported sale price of our Class A Common Stock on the common stockNew York Stock Exchange on June 14, 2001August 8, 2016 was $30.79$12.77 per share.

 See "Risk Factors"

We will pay the expenses related to the registration of the shares of the securities covered by this prospectus. The selling securityholders will pay any underwriting discounts or commissions or agents’ commissions and selling expenses they may incur.

Investing in our Class A Common Stock and Class A Warrants involves a high degree of risk. You should consider carefully the risks and uncertainties in the section entitled “Risk Factors” beginning on page 6 in4 of this prospectus, to read about certain factors you should considerin the documents we file with the Securities and Exchange Commission and as set forth in any applicable prospectus supplement before buying the common stock.investing in our securities.

Neither the Securities and Exchange Commission nor any other regulatory bodystate securities commission has approved or disapproved of these securities or passed upon the accuracyadequacy or adequacyaccuracy of this prospectus. Any representation to the contrary is a criminal offense.

The date of this prospectus is              , 2016.

TABLE OF CONTENTS

 To

ABOUT THIS PROSPECTUS

This prospectus is part of a registration statement on Form S-3 that we filed with the extentSecurities and Exchange Commission (the “SEC”) using a “shelf” registration process. Under this shelf registration process, the selling securityholders may, from time to time, offer and sell, in one or more offerings, the securities described in this prospectus.

This prospectus only provides you with a general description of the securities that may be offered. Each time the selling securityholders sell securities using this shelf registration, we may provide a supplement to this prospectus that will contain specific information about the terms of that offering, including the specific amounts, prices and terms of the securities offered. The prospectus supplement may also add, update or change information contained in this prospectus. If there is any inconsistency between the information in this prospectus and any applicable prospectus supplement, you should rely on the information in the applicable prospectus supplement. You should read in their entirety both this prospectus and any accompanying prospectus supplement, together with the additional information described under the sections entitled “Where You Can Find More Information” and “Incorporation of Certain Documents by Reference” before deciding to invest in any of the securities being offered.

This prospectus and any accompanying prospectus supplement do not contain all of the information included in the registration statement as permitted by the rules and regulations of the SEC. We are subject to the reporting requirements of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), and, therefore, file reports and other information with the SEC. Statements contained in this prospectus and any accompanying prospectus supplement about the provisions or contents of any agreement or other document are only summaries. If SEC rules require that any agreement or document be filed as an exhibit to the registration statement, you should refer to that agreement or document for its complete contents. Any summaries of such agreement or documents set forth in this prospectus or any accompanying prospectus supplement are qualified in their entirety by reference to such agreement or document as filed with the SEC.

You should not assume that the Underwriters sell moreinformation in this prospectus, any accompanying prospectus supplement or any document incorporated by reference herein is accurate as of any date other than 5,000,000 sharesthe date on the front of common stock, the Underwriters have the option to purchase up to an additional 750,000 shares from certaineach document, regardless of the selling stockholderstime of delivery of this prospectus, any accompanying prospectus supplement or any sale of securities. Our business, financial condition, results of operations and prospects may have changed since then. We have not authorized anyone to provide you with information that is different. This prospectus may only be used where it is legal to sell these securities. Any information we incorporate by reference in accordance with SEC rules into this prospectus or any accompanying prospectus supplement shall be deemed to be a part of this prospectus from the respective dates of filing of that information.

IF YOU ARE IN A JURISDICTION WHERE OFFERS TO SELL, OR SOLICITATIONS OF OFFERS TO PURCHASE, THE SECURITIES OFFERED BY THIS PROSPECTUS OR ANY ACCOMPANYING PROSPECTUS SUPPLEMENT ARE UNLAWFUL, OR IF YOU ARE A PERSON TO WHOM IT IS UNLAWFUL TO DIRECT THESE TYPES OF ACTIVITIES, THEN THE OFFER PRESENTED IN THIS PROSPECTUS OR ANY ACCOMPANYING PROSPECTUS SUPPLEMENT DOES NOT EXTEND TO YOU.

In this prospectus, unless otherwise specified or the context otherwise requires, we use the terms “the Company,” “OSG,” “we,” “our” and “us” to refer to Overseas Shipholding Group, Inc., a Delaware corporation, and its consolidated subsidiaries.

RISK FACTORS

An investment in this prospectus assumes thatour securities involves a high degree of risk. You should carefully consider the Underwriters' over-allotment option to purchase an additional 750,000 shares is not exercised. If it is exercised, up to an additional 750,000 shares will be soldspecific risks described below, in the documents incorporated by the selling stockholders.

Risk Factors

    Prospective purchasers of the common stock should consider all of the information contained inreference into this prospectus, including in the information incorporated by reference,“Risk Factors” sections of our Annual Report on Form 10-K for the fiscal year ended December 31, 2015 and in any applicable prospectus supplement before making an investment decision. If any of the risks described below or in these documents actually materializes, our business, financial condition, results of operations and prospects could be materially adversely affected. As a result, the common stock. Ourvalue of our securities could decline and you could lose part or all of your investment. The risks described below are not the only ones we face. There may be other unknown or unpredictable economic, business, competitive, regulatory or other factors that could have material adverse effects on our future results. Past financial performance is subject to various risks, including the cyclical naturemay not be a reliable indicator of the oil shipping industry, the volatility of charter ratesfuture performance and vessel values, and potential liabilities and costs under environmental laws and regulations. You should consider carefully the information set forth in the section of this prospectus entitled "Risk Factors" beginning on page 6.

4

The market price of our stock. In that case,securities may fluctuate significantly following the offering and you could lose all or a part of your investment.

Industry Specific Risk Factorsinvestment as a result.

The market price of our securities may fluctuate substantially. The price of our Class A decline in demand for crude oil could cause demand for tanker capacityCommon Stock and charter rates to decline which would decrease our revenues and profitability.

    The demand for tanker capacity to transport crude oil is influenced by the demand for crude oil and other factors including:

•

global and regional economic and political conditions;

•

increases and decreases in production of crude oil, particularly by OPEC and other key producers;

•

developments in international trade;

•

changes in seaborne and other transportation patterns, including changesClass A Warrants that will prevail in the distances that cargoesopen market following this offering may be higher or lower than the price you pay for such securities. You may not be able to resell your Class A Common Stock or Class A Warrants at or above the price you paid for such securities due to a number of factors, some of which are transported;

•

environmental concerns;

•

weather;beyond our control. These risks include those described or referred to in this “Risk Factors” section, under “Cautionary Note Regarding Forward-Looking Statements” and

•

competition from alternative sources of energy.

Any of thesethe foregoing factors could also cause the price of our Class A Common Stock and Class A Warrants to fall and may expose us to securities class action litigation. Any securities class action litigation could result in substantial costs and the diversion of management’s attention and resources. Furthermore, the stock market has recently experienced volatility that, in some cases, has been unrelated or disproportionate to the operating performance of particular companies. These broad market and industry fluctuations may adversely affect the demandmarket price of our securities, regardless of our actual operating performance.

Our Class A Common Stock and Class A Warrants are thinly traded, and your ability to sell such Class A Common Stock or Class A Warrants will be limited.

We cannot assure you as to the liquidity of any market that may develop for tanker capacitythe Class A Common Stock and charter rates. Any decrease in demandClass A Warrants, your ability to sell your Class A Common Stock and Class A Warrants or the price at which you would be able to sell such securities. Future trading prices of the Class A Common Stock and Class A Warrants will depend on many factors, including, among other things, our operating results and the market for tanker capacitysimilar securities. The effect an offering of our Class A Common Stock or decrease in charter rates would adversely affect our business.Class A Warrants by one or more selling securityholder from time to time will have on the volume or trading price of these securities is uncertain. You may not be able to sell acquired securities at the price equal to or greater than the offering price.

 Demand

Prior to this offering, there has not been an active trading market for our Class A Warrants. Our Class A Warrants are currently traded as “restricted securities” in the over-the-counter market and in privately negotiated transactions among individual holders pursuant to exemptions from the Securities Act. Although our Class A Common Stock is listed on the New York Stock Exchange, our common stock has experienced low trading volume. Limited trading volume may subject our common stock to greater price volatility and may make it difficult for investors to sell shares at a price that is attractive to them

Our common stock is subject to restrictions on foreign ownership, which could have a negative impact on the transferability of our common stock, its liquidity and market value, and on a change of control of OSG.

Certain of our U.S. Flag operations are conducted in the U.S. coastwise trade and are governed by the U.S. federal law commonly known as the “Jones Act”. The Jones Act restricts waterborne transportation of goods and passengers between points in the United States to vessels owned and our related servicescontrolled by “U.S. Citizens” as defined thereunder (as so defined, “U.S. Citizens”). We could lose the privilege of owning and operating vessels in transporting crude oil is also dependent upon world and regional oil markets. Historically, these markets have been volatile as a resultthe Jones Act trade if non-U.S. Citizens were to own or control, in the aggregate, more than 25% of the many conditions and events that can affect the price, demand, production and transport of oil. Any decreaseequity interests in the shipment of crude oil in these markets could result in tanker charter rates in our markets declining or a decrease in the number of charters for our vessels, both of which couldCompany. Such loss would have a material adverse effect on our revenuesresults of operations.

Our Amended and profitability.

An increase in the supplyRestated Certificate of tanker capacity without an increase in demand for tanker capacity could cause charter ratesIncorporation and Amended and Restated By-Laws authorize our Board of Directors to decline which could have a material adverse effect on our revenues and profitability.

    Historically, the tanker industry has been cyclical. The profitability and asset values of companies in the industry have fluctuated based on changes in the supply of and demand for tanker capacity. The supply of tankers generally increases with deliveries of new vessels and decreases with the scrapping of older vessels, conversion of vessels to other uses, such as floating production and storage facilities, and loss of tonnage as a result of casualties. Currently there is significant newbuilding activityestablish with respect to VLCCsany class or series of our capital stock certain rules, policies and Aframaxes. Ifprocedures, including procedures with respect to transfer of shares, to assist in monitoring and maintaining compliance with the number of new ships delivered exceeds the number of vessels being scrapped, tanker capacity will increase. If the supply of tanker capacity increases and the demand for tanker capacity does not, the charter rates paid for our vessels could materially decline. A decline in charter rates could have a material adverse effect on our revenues and profitability.

6

Charter rates may decline from their current level which could have a material adverse effect on our revenues and profitability.

    Average charter rates for 2000 and for the first quarter of 2001 have significantly exceeded the average charter rates in prior periods, particularly 1999. Because many of the factors which influence the supply of and demand for vessel capacity are unpredictable, the nature, timing and degree of changes in charter rates are unpredictable. Charter rates can also be negatively affected by anticipated additional tanker capacity. All of the factors influencing the supply of and demand for oil tankers, and therefore future charter rates and values of vessels, are beyond our control. The nature, timing and degree of changes in industry conditions are unpredictable. These changes could have a material adverse effect on our revenues and profitability.

Our revenues are subject to seasonal variations.

    We operate our tankers in markets that have historically exhibited seasonal variations in demand, and therefore, charter rates. Tanker charter rates (and our revenues and earnings) are typically higher in the winter and fall months (the first and fourth quarters of the calendar year) as a result of anticipated increased oil consumption in the Northern Hemisphere during the winter months. In addition, unpredictable weather patterns in the winter months and variations in oil reserves tend to disrupt vessel scheduling. Because we largely trade in the spot market, seasonality has affected our operating results on a quarter-to-quarter basis and could continue to do so in the future.

Environmental costs and liabilities could have a material adverse effect on our business, results of operations or financial condition.

    Our operations are subject to extensive laws, treaties and international agreements governing environmental protection, the management, transportation, discharge and release of hazardous substances, and human health and safety. We are required to satisfy insurance and financial responsibility requirements for potential oil spills and other pollution incidents. In addition, our vessels must meet stringent operational, maintenance, inspection, training and structural requirements and follow approved safety management and emergency preparedness procedures and are subject to rigorous inspections by governmental authorities and other parties. Violations of applicable requirements could result in substantial penalties, and in certain instances, seizure or detention of one or more vessels. From time to time, in connection with our shipping operations, we have experienced spills of oil or other materials and incurred cleanup costs relating to such spills. We could be required to pay the costs of responding to future oil spills or cleaning up contaminated properties pursuant to the Oil PollutionJones Act of 1990, the Comprehensive Environmental Response Compensation and Liability Act and other U.S. and foreign laws and regulations. We also could become subject to personal injury or property damage claims relating to exposure to hazardous substances in connection with our existing and historical operations. Our existing insurance may not be sufficient to cover all such risks, in which case such risks could have a material adverse effect on our business, results of operations or financial condition.

ownership restrictions. In order to maintainprovide a reasonable margin for compliance with existing and future laws, treaties and international agreements, we incur, and expect to continue to incur, substantial costs in meeting maintenance and inspection requirements, developing and implementing emergency procedures to address potential oil spills, and obtaining insurance coverage or other required financial assurance of our ability to address pollution incidents. These laws, treaties and international agreements also can:

•

impair the economic value of our vessels;

•

require a reduction in cargo-carrying capacity or other structural or operational changes;

•

make our vessels less desirable to potential charterers or purchasers;

•

lead to decreases in available insurance coverage for affected vessels; or

•

result in the denial of access to, or detention in, certain ports.

7

Future environmental requirements may be adopted which could limit our ability to operate, require us to incur substantial additional costs or otherwise have a material adverse effect on our business, results of operations or financial condition.

Because the market value of our vessels may fluctuate significantly, we may incur losses when we sell vessels, which could adversely affect our financial condition.

    The market value of vessels has fluctuated over time. The market value of oil tankers may vary significantly over time based upon various factors, including:

•

general economic and market conditions affecting the tanker industry;

•

number of vessels in the world fleet;

•

types and sizes of vessels available;

•

changes in trading patterns affecting demand for particular sizes and types of vessels;

•

cost of newbuildings;

•

prevailing level of charter rates; and

•

technological advances in vessel design and propulsion.

    Declining vessel values could affect our ability to replace existing financings upon their expiration as well as raise cash generally and thereby adversely impact our liquidity. In addition, declining vessel values could result in a breach of certain loan covenants, which could give rise to events of default under the relevant financing agreements. There can be no assurance that the market value of our vessels will not decline, nor can there be any assurance that the market value of the vessels that are currently under construction or on order will not decline during the construction process.

Shipping is a business with inherent risks and our insurance may not be adequate.

    Our vessels and their cargoes are at risk of being damaged or lost because of events such as:

•

marine disasters;

•

bad weather;

•

mechanical failures;

•

human error;

•

war, terrorism and piracy; and

•

other unforeseen circumstances or events.

In addition, transporting crude oil creates a risk of business interruptions due to political circumstances in foreign countries, hostilities, labor strikes, port closings and boycotts. Any of these events may result in loss of revenues and increased costs.

    We carry insurance to protect against most of the accident-related risks involved in the conduct of our business. We currently maintain one billion dollars in coverage for each of our vessels for liability for spillage or leakage of oil or pollution. We also carry insurance covering lost revenue resulting from vessel off-hire due to vessel damage. Nonetheless, risks may arise against which we are not adequately insured. For example, a catastrophic spill could exceed our insurance coverage and have a material adverse effect on our operations. In addition, we may not be able to procure adequate insurance coverage at commercially reasonable rates in the future and we cannot guarantee that any particular claim will be paid. In the past, new and stricter environmental regulations have led to higher costs for insurance covering environmental damage or pollution, and new regulations could lead to similar increases or even make this type of insurance unavailable. Furthermore, even if insurance coverage is adequate to cover our losses, we may not be able to timely obtain a replacement ship in the event of a loss. We may also be subject to calls, or

8

premiums, in amounts based not only on our own claim records but also the claim records of all other members of the protection and indemnity associations through which we obtain insurance coverage for tort liability. Our payment of these calls could result in significant expenses to us which would reduce our profits or cause losses.

Because we conduct our business on a worldwide basis, we face a number of significant risks that could result in losses or higher costs.

    Our vessels operate all over the world, exposing us to many risks, including:

•

changing economic, political and social conditions in the countries where we do business or where our vessels are registered or flagged;

•

the imposition of increased environmental and safety regulations by international organizations, classification societies, flag states and port states;

•

the imposition of taxes by flag states, port states and jurisdictions in which we or our subsidiaries are incorporated or where our vessels operate;

•

currency fluctuations;

•

war, terrorism and piracy; and

•

expropriation of our vessels.

As a result of these risks, we may incur losses or higher costs, including those incurred as a result of the impairment of our assets or a curtailment of our operations.

Our vessels could be arrested by maritime claimants which could result in a significant loss of earnings and cash flow for the related off-hire period.

    Crew members, suppliers of goods and services to a vessel, shippers of cargo and other parties may be entitled to a maritime lien against a vessel for unsatisfied debts, claims or damages. In many jurisdictions, a maritime lienholder may enforce its lien by either arresting or attaching a vessel through foreclosure proceedings. The arrest or attachment of one or more of our vessels could result in a significant loss of earnings and cash flow for the related off-hire period.

    In addition, international vessel arrest conventions and certain national jurisdictions allow so-called "sister ship" arrests, that allow the arrest of vessels that are within the same legal ownership as the vessel which is subject to the claim or lien. Certain jurisdictions go further, permitting not only the arrest of vessels within the same legal ownership, but also any "associated" vessel. In nations with these laws, an "association" may be recognized when two vessels are owned by companies controlled by the same party. Consequently, a claim may be asserted against us, any of our subsidiaries or our vessels for the liability of one or more of the other vessels we own.

Company Specific Risk Factors

Our existing financing arrangements contain provisions that may adversely affect our ability to operate and expand our business and our ability to obtain additional financing.

    We had approximately $864.5 million of debt outstanding at March 31, 2001, of which approximately $182.1 million is secured by a pledge of certain of our vessels and related collateral as security to the lenders under these loan agreements. This substantial indebtedness may:

•

limit our ability to obtain additional financing to meet working capital requirements and provide for capital expenditures;

•

require that a substantial portion of our cash flow be dedicated to the payment of principal and interest on our indebtedness; and

•

limit our ability to acquire additional tonnage and expand our business.

9

    In addition, our existing financing agreements impose operating and financial restrictions, including restrictions which limit our ability to:

•

incur additional indebtedness;

•

create liens on our assets;

•

sell the capital stock of our subsidiaries or other assets;

•

make certain investments, including in joint ventures;

•

engage in mergers and acquisitions;

•

make capital expenditures or pay dividends;

•

change the management of our vessels or terminate or materially amend the management agreement relating to each vessel; and

•

sell our vessels.

    As a result, we may need the permission of our lenders to engage in various corporate activities. Our lenders' interests may be different from, and may be adverse to, those of our stockholders, and we cannot assure you that we will be able to obtain our lenders' permission if and when we need it. Our failure to obtain a required permission will keep us from effecting corporate transactions and may prevent us from expanding or properly managing our business.

    In addition, if we default under any of our secured loan agreements, we could forfeit our rights in our vessels and their charters, the lenders could foreclose on the mortgages on the vessels and the related collateral, and we could lose our rights in the vessels and their charters.

When our credit facilities mature, we may not be able to refinance or replace them.

    When our indebtedness matures, we may need to refinance it and we may not be able to do so. If we are able to refinance maturing indebtedness, the terms of any refinancing or alternate credit arrangements may contain terms and covenants that restrict our financial and operating flexibility.

Interest rate fluctuations may significantly affect our loan payments.

    At March 31, 2001, approximately $638.1 million, or 74%, of our indebtedness bore interest at floating interest rates. We have entered into interest rate swaps with respect to a portion of this floating rate indebtedness, resulting in approximately $425 million of our total indebtedness being subject to interest rate fluctuation. Increases in interest rates would increase interest payments on that indebtedness.

We are highly dependent upon volatile spot market charter rates.

    We depend on spot charters for a significant portion of our revenues. During 2000, we derived approximately 76% of our net shipping revenues from spot charters and contracts of affreightment which are predominantly priced on a spot market basis. During the quarter ended March 31, 2001, we derived approximately 80% of our net shipping revenues from spot voyages and contracts of affreightment.

    The spot market is highly competitive and charter rates in the spot market are volatile. As a result, our revenues may fluctuate significantly. Successful operation of a vessel in the spot market depends on a number of factors, including obtaining profitable voyage charters and minimizing, to the extent possible, ballast legs (time spent traveling unladen to load cargo) and time waiting for charters. Increased dependence on the spot market by us could result in a lower utilization of our vessels and decreased profitability. There can be no assurance that charter rates in the spot market will not decline, or that charters in the spot market will continue to be available.

10

We may not be able to renew time charters when they expire.

    There can be no assurance that any of our existing time charters will be renewed, or if renewed, will be renewed at similar rates. If upon expiration of the existing time charters, we are unable to obtain time charters or voyage charters at rates equivalent to those received under the charters, our profitability may be adversely affected.

Termination or change in the nature of our relationship with the Tankers International pool or the Aframax Pool could adversely affect our business and our ability to grow our VLCC and Aframax fleets.

    Our VLCCs are part of the Tankers International pool and our Aframaxes are part of the Aframax Pool. Being part of these pools enhances the financial performance of our vessels as a result of the higher vessel utilization these pools provide. A participant in either pool may withdraw upon notice in accordance with the respective pool agreement. The termination of Tankers International or the Aframax Pool, the withdrawal by participants in either pool or other significant change in our or another participant's relationship with either pool could adversely affect our ability to commercially market our VLCC and Aframax fleets.

We may not be able to grow our VLCC and Aframax fleets.

    One part of our strategy is to continue to grow, on an opportunistic basis, our VLCC and Aframax fleets. Our ability to grow these fleets will depend upon a number of factors, many of which we cannot control. These factors include our ability to:

•

identify acquisition candidates and joint venture opportunities;

•

consummate acquisitions or joint ventures;

•

integrate any acquired vessels or businesses successfully with our existing operations;

•

hire and train qualified personnel; and

•

obtain required financing.

Our strategy of growing our business in part through acquisitions is capital intensive, time consuming and subject to a number of inherent risks.

    Part of our business strategy is based upon the opportunistic acquisitions of complementary businesses or vessels. If we fail to develop and integrate any acquired businesses or vessels effectively, our results of operations may be adversely affected. In addition, our management team will need to devote substantial time, attention and other resources to the integration of the acquired businesses or vessels, which could distract them from running the business. Operational or financial problems may occur as a result of the integration with our business of an acquisition.

Our newbuilding program requires us to advance significant progress payments prior to the time a vessel is placed in service.

    We currently have contracts for the delivery of four newbuilding VLCCs and four newbuilding Aframaxes. The aggregate purchase price for these newbuildings is approximately $406 million, of which progress payments of $201 million have been made through March 31, 2001. When we order newbuildings, we are typically required to expend substantial sums in the form of progress payments during the construction of the vessel, but we do not derive any revenue from the vessel until after its delivery. Moreover, if we were unable to obtain financing required to complete payments on any of our newbuilding orders, we could effectively forfeit all or a portion of the progress payments previously made with respect to such contract.

Operating costs and capital expenses will increase as our vessels age.

    In general, capital expenditures and other costs necessary for maintaining a vessel in good operating condition increase as the age of the vessel increases. Accordingly, it is likely that the

11

operating costs of the older vessels in our fleet will increase. Due to improvements in engine technology, older vessels are typically less fuel efficient than more recently constructed vessels. In addition, changes in governmental regulations, safety or other equipment standards as well as compliance with classification society standards may require us to make additional expenditures. For example, we may be required to make significant expenditures for alterations or the addition of new equipment. In addition, these modifications may require us to take our vessels out of service for extended periods of time (with corresponding losses of revenue) in order to make such alterations or to add such equipment. Cargo insurance rates increase with the age of a vessel, making older vessels less desirable to charterers. There can be no assurance that market conditions will justify such expenditures or enable us to operate our older vessels profitably during the remainder of their economic lives.

Our purchase of second-hand vessels carries risks associated with the quality of those vessels.

    Our fleet renewal and expansion strategy includes the opportunistic acquisition of quality second-hand vessels as well as the ordering of newbuildings. Second-hand vessels typically do not carry warranties with respect to their condition in contrast to warranties available for a newbuilding. While we generally inspect any second-hand vessel prior to purchase, such an inspection would normally not provide us with as much knowledge of its condition as we would possess if the vessel had been built for us and operated by us during its life.

In the highly competitive international tanker market, we may not be able to effectively compete for charters with new entrants or established companies with greater resources.

    Our vessels are employed in a highly competitive market. Competition arises primarily from other tanker owners, including major oil companies and independent owners, some of which have substantially greater resources than we do. Competition for the transportation of crude oil and other petroleum products can be intense and depends on price, location, size, age, condition and the acceptability of the vessel and its operators to the charterers. We believe that because ownership of the world tanker fleet is highly fragmented, no single owner is able to substantially influence charter rates. To the extent we enter into new geographic regions or provide new services, we may not be able to compete profitably. New markets may involve competitive factors which differ from those of our current markets and the competitors in those markets may have greater financial strength and capital resources than we do.

We depend upon a few significant customers for a large part of our revenues.

    Historically, we have derived a significant portion of our revenue from a small number of charterers. In 1999 and 2000, our 10 largest customers accounted for approximately 50% and 46%, respectively, of our consolidated voyage revenues. One customer accounted for $35.2 million, or approximately 10%, of our consolidated voyage revenues for 1999. No other single customer accounted for over 10% of our consolidated voyage revenues in either 1999 or 2000. The failure by a major charterer to meet its charter payment obligations could result in a material loss.

We depend on our key personnel and may have difficulty attracting and retaining skilled employees.

    Our success depends to a significant extent upon the abilities and efforts of our key personnel, particularly senior management who have been employed by us for many years. The loss of the services of any of our key personnel or our inability to attract and retain qualified personnel in the future could have a material adverse effect on our business, financial condition and operating results.

12

Our inability to successfully shift certain ship management and administrative functions to our U.K. office may adversely affect our operations.

    As part of our cost reduction program, we are shifting ship management and administrative functions associated with our international fleet from New York to Newcastle, U.K. If we are unable to make this shift successfully or if it is delayed, we may not realize the cost reductions we anticipate and our ability to manage our vessels and administer our business may be adversely affected.

We may face unexpected drydock costs for our vessels.

    Vessels must be drydocked periodically, in the case of a VLCC or Aframax vessel, typically every 24 to 30 months. The cost of repairs and renewals required at each drydock are difficult to predict with certainty and can be substantial. Our insurance does not cover these costs. In addition, vessels may have to be drydocked in the event of accidents or other unforeseen damage. Our insurance may not cover all of these costs. Large drydocking expenses could significantly decrease our profits.

We may not be able to make dividend payments to holders of our common stock.

    The timing and amount of dividends, if any, will depend, among other things, on our operating results, cash flow, working capital requirements and other factors deemed relevant by our Board of Directors. Because we are a holding company with no material operating assets other than the stock of our subsidiaries, our ability to pay dividends on our common stock is dependent on the earnings and cash flow of our subsidiaries. The credit agreements governing certain of our credit facilities also limit our ability to pay dividends.

Restrictions on foreign ownership of our common stock may decrease the liquidity of our common stock.

    U.S. law requires that, to be eligible for U.S. coastwise trade, a corporation owning a vessel must be at least 75% owned by U.S. citizens. In order to assure compliance with this citizenship requirement,Jones Act, our Board of Directors has adopted a requirementdetermined that until further action by it, at least 77% (the “Minimum Percentage”) of the outstanding shares of each class of our capital stock must be owned by U.S. Citizens. Moreover, our Amended and Restated Certificate of Incorporation and Amended and Restated By-Laws provide that any purported transfer of equity interests in us that caused the percentage of outstanding shares of a class of our capital stock to fall below the Minimum Percentage will be ineffective to transfer the equity interests or any voting, dividend or other rights associated with such interests.

The percentage of U.S. Citizen ownership of our outstanding common stock be held by U.S. citizens. This requirement mayfluctuates based on daily trading, and at times in the past has declined to the Minimum Percentage. At and during such time that the Minimum Percentage is reached with respect to outstanding shares of a class of our stock, we are unable, among other things, to issue any further shares of such class of common stock to non-U.S. Citizens or to approve transfers of such class of common stock to non-U.S. Citizens. The existence and enforcement of these ownership restrictions could have an adverse impact on the liquidity or market value of our equity securities. Under certain circumstances, the ownership restrictions could discourage, delay or prevent a change of control of OSG.

Our outstanding warrants are not subject to the above ownership restrictions, but the warrants include provisions limiting the right of non-U.S. Citizens to exercise warrants if the shares of common stock because ifthat would be issued upon exercise would cause the percentage of outstanding shares of our common stock held by non-U.S. citizens reaches 23%, U.S. holders will be unable to sell additional shares to non-U.S. citizens. Any purported transfer of shares in violation of these provisions will be ineffective to transfer the shares or any voting, dividend or other rights in respect of the shares.

The requirement that at least 77% of our outstanding common stock be held by U.S. citizens may restrict us from making certain acquisitions usingCitizens to decline below the Minimum Percentage.

Holders of our common stock.Class A Warrants will have no rights as a stockholder of the Company until such holders exercise their warrants and acquires shares of Class A Common Stock.

 Currently, approximately 83.6%

Until a holder of Class A Warrants acquires shares of Class A Common Stock upon exercise of its Class A Warrants, such holder will have no rights with respect to the Class A Common Stock underlying such warrants. Any such exercising holder will be entitled to exercise the rights of a shareholder only as to matters of which the record date occurs after the exercise date. The Class A Warrants do not confer any rights of common share ownership on their holders, such as voting rights or the right to receive dividends, and represent solely the right to acquire shares of Class A Common Stock.

Future sales of our common stock or warrants, or the perception in the public markets that these sales may occur, may depress our stock price.

Sales of substantial amounts of our common stock or warrants, including the sale by the selling securityholders of our Class A Common Stock and Class A Warrants from time to time, or the perception that these sales could occur, could adversely affect the price of our common stock or warrants and impair our ability to raise capital through the sale of equity securities.

The Company has a limited history of paying cash dividends on its securities.

The Company has not paid any regular cash dividends since the third quarter of 2011. On February 29, 2016, the Board of Directors declared a cash dividend of $0.08 per share of common stock, which was paid on March 25, 2016. The declaration and timing of future cash dividends, if any, will be at the discretion of the Board of Directors and will depend upon, among other things, our future operations and earnings, capital requirements, general financial condition, contractual restrictions, restrictions imposed by applicable law or the SEC and such other factors as our Board of Directors may deem relevant.

We are a holding company and depend on the ability of our subsidiaries to distribute funds to us in order to satisfy our financial obligations or pay dividends.

Overseas Shipholding Group, Inc. is held by U.S. citizens.a holding company and its subsidiaries conduct all of its operations and own all of its operating assets. It has no significant assets other than the equity interests in its subsidiaries. As a result, of our relatively high non-U.S. holdings, we may be unableits ability to offer certain non-U.S. sellerssatisfy its financial obligations or pay dividends depends on its subsidiaries and their ability to distribute funds to it. In addition, the terms of vessels our common stock as consideration. In some cases, our common stock as opposed to cash may be the preferred form of consideration for sellers. Our inability to offer our common stock as consideration to certain sellers could make certain acquisition transactions unavailable to us.

Anti-takeover provisions in our financing agreements restrict the ability of our organizational documents, our Rights Agreement and certainsubsidiaries to distribute funds to Overseas Shipholding Group, Inc.

Some provisions of Delaware law and our governing documents could discourage a takeover that stockholders may consider favorable, or otherwise influence our ability to consummate a change of control.

Delaware law and provisions contained in our Amended and Restated Certificate of Incorporation and Amended and Restated By-Laws could have the effect of discouraging, delaying, deferring or preventing a mergerchange of control of us. In addition, these provisions could make it more difficult to bring about a change in the composition of our board of directors. For example, our Amended and Restated Certificate of Incorporation and Amended and Restated By-Laws:

These and other provisions of our organizational documents and Delaware law may have the effect of delaying, deferring or acquisition,preventing changes of control or changes in management, even if such transactions or changes would have significant benefits for our stockholders. See “Description of Capital Stock.” As a result, these provisions could limit the price some investors might be willing to pay in the future for shares of our common stock.

Separately, we have elected to opt out of Section 203 (“Section 203”) of the Delaware General Corporation Law (the “DGCL”), which restricts certain business combinations between a Delaware corporation and an “interested stockholder.” Accordingly, we will be able to enter into such transactions with our principal stockholders without complying with the requirements of Section 203. The election to opt out of Section 203 could deprive certain stockholders of an opportunity to receive a premium for their common stock as part of a sale of OSG, particularly if we enter into a transaction with an “interested stockholder.”

We may issue preferred shares in the future, which could make it difficult for another company to acquire us or could otherwise adversely affect holders of our common stock and warrants, which could depress the price of our securities.

Our Amended and Restated Certificate of Incorporation authorizes us to issue one or more series of preferred shares. Our Board of Directors will have the authority to determine the preferences, limitations and relative rights of such preferred shares and to fix the number of shares, up to the current authorized share capital amount, constituting any series and the designation of such series, without any further vote or action by our shareholders. Our preferred shares could be issued with voting, liquidation, dividend and other rights superior to the rights of shares of our common stock. The potential issuance of preferred shares may delay or prevent a change in control of us, discouraging bids for our common stock at a premium to the market price, and materially and adversely affect the market price of our common stock.

    Severalstock and warrants and the voting and other rights of the holders of shares of our existing financing agreements impose restrictions on changes of control ofcommon stock.

If securities or industry analysts issue an adverse or misleading opinion regarding us or do not publish or cease publishing research or reports about us, our companybusiness, our market or our competitors, or if they change their recommendations regarding our Class A Common Stock adversely, the price and our ship-owning subsidiaries. These agreements include requirements that we obtain

13

the lenders' consent prior to any merger or consolidation unless we ensure that any surviving entity assumes the relevant indebtedness.

    Several provisions of our certificate of incorporation, our by-laws and Delaware law could discourage, delay or prevent a merger or acquisition that stockholders may consider favorable, including those provisions:

•

prohibiting cumulative voting in the election of directors;

•

providing that vacancies on the Board of Directors will be filled by the remaining directors then in office; and

•

prohibiting us from engaging in a "business combination" with an "interested stockholder" for a period of three years after the date of the transaction in which the person became an interested stockholder unless certain provisions are met.

    These provisions could impede the stockholders' ability to change our management and Board of Directors. Please see "Description of Capital Stock."

Offering Specific Risks

The pricetrading volume of our common stock may fluctuate significantly, which may result in losses for investors.and warrants could decline.

The trading market price for our common stock has beenClass A Common Stock and Class A Warrants will be influenced, to some extent, by the research and reports that industry or securities analysts may continue to be volatile. For example, during the 52-week period ended June 8, 2001, the closing prices ofpublish about us, our common stock as reported on the New York Stock Exchange ranged from a high of $37.09 to a low of $20.25. Our stock price can fluctuate as a result of a variety of factors, including:

•

actual or anticipated fluctuations in quarterly and annual results;

•

mergers and strategic alliances in the tanker industry;

•

market conditions in the industry;

•

changes in government regulation;

•

fluctuations inbusiness, our quarterly revenues and earnings and those of our publicly held competitors;

•

shortfalls in our operating results from levels forecast by securities analysts;

•

announcements concerning usmarket or our competitors;competitors. We do not control these analysts or the content and

•

the general state opinions included in their reports. If any of the securities market.

    Because of this volatility, we may fail to meet the expectations ofanalysts who cover us change their recommendation regarding our stockholdersClass A Common Stock adversely, or of securities analysts at some time in the future, andprovide more favorable relative recommendations about our competitors, our stock price could decline as a result.

Future saleswould likely decline. If any analyst who covers us were to cease coverage of us or fail to publish reports on us regularly, or if analysts elect not to provide research coverage of our common stockClass A Common Stock, we could depresslose visibility in the marketfinancial markets, which in turn could cause the price and/or trading volume of our common stock.Class A Common Stock and Class A Warrants to decline.

CAUTIONARY NOTE REGARDING FORWARD-LOOKING STATEMENTS

 The market price

Some of our common stock could decline duethe statements contained in this prospectus and the documents incorporated by reference herein constitute “forward-looking statements” within the meaning of the Private Securities Litigation Reform Act of 1995. All such statements other than statements of historical facts should be considered forward-looking statements. These statements can be identified by the fact that they do not relate strictly to saleshistorical or current facts, and you can often identify these forward-looking statements by the use of a large number of shares in the market after this offeringforward-looking words such as “outlook,” “believes,” “expects,” “potential,” “continues,” “may,” “will,” “should,” “could,” “seeks,” “approximately,” “predicts,” “intends,” “plans,” “estimates,” “anticipates,” “target,” “projects,” “forecasts,” “shall,” “contemplates” or the perceptionnegative version of those words or other comparable words. Such forward-looking statements represent our reasonable expectation with respect to future events or circumstances based on various factors and are subject to various risks and uncertainties and assumptions relating to our operations, financial results, financial condition, business, prospects, growth strategy and liquidity. Accordingly, there are or will be important factors that could cause our actual results to differ materially from those indicated in these statements. You should not place undue reliance on any forward-looking statements and should consider the following factors, as well as the factors discussed elsewhere in this prospectus, including under “Risk Factors,” when reviewing such statement. We believe that these salesfactors include, but are not limited to:

The factors identified above should not be construed as exhaustive list of factors that could occur. These sales could also make it more difficult or impossible for us to sell equity securitiesaffect our future results, and should be read in the future at a time and price that we deem appropriate to raise funds through offerings of common stock.

    As of June 1, 2001, 34.2 million shares of common stock were outstanding. We have also reserved 2.9 million shares of common stock for issuance under our stock option plans. Options to purchase 1.9 million shares were outstanding as of June 1, 2001. We and our executive officers and directors and the selling stockholders have agreedconjunction with the Underwriters not to offer, sell, contract to sell or otherwise dispose of any shares of common stock without the prior written consent of Goldman, Sachs & Co.,other cautionary statements that are included elsewhere in the case of us and our executive officers and directors who are not selling stockholders, prior to 90 days after the date ofthis prospectus. The forward-looking statements made in this prospectus or, in the caseare made only as of our selling stockholders, 180 days after the date of this prospectus. AfterThe forward-looking statements made in documents incorporated by reference into this prospectus are made only as of the date of such documents. The forward-looking statements made in any accompanying prospectus supplement are made only as of the date of such document. We do not undertake any obligation to publicly update or review any forward-looking statement except as required by law, whether as a result of new information, future developments or otherwise. If we do update one or more forward-looking statements, no inference should be made that time, the selling stockholderswe will make additional updates with respect to those or other forward-looking statements.

If one or more of these or other risks or uncertainties materialize, or if our underlying assumptions prove to be incorrect, our actual results may vary materially from what we may have expressed or may not decide, based upon the prevailing market and other conditions, to sell all or a portion of their remaining shares in the market.

14

FORWARD-LOOKING STATEMENTS

    This prospectus includesimplied by these forward-looking statements. We have based these forward-looking statements largelycaution that you should not place undue reliance on our current expectations and projections about future events and financial trends affecting the financial conditionany of our business. These forward-looking statements are subject to several risks, uncertainties and assumptions.

    In addition,statements. You should specifically consider the factors identified in this prospectus the words "believe," "may," "will," "estimate," "continue," "anticipate," "intend," "expect" and similar expressions, as they relatethat could cause actual results to us,differ before making an investment decision to purchase our business or our management, are intended to identify forward-looking statements.

    In light of thesecommon stock. Furthermore, new risks and uncertainties arise from time to time, and it is impossible for us to predict those events or how they may affect us.

You should refer to our periodic and current reports filed with the SEC for further information on other factors that could cause actual results to be significantly different from those expressed or implied by these forward-looking events and circumstances discussedstatements. See “Where You Can Find More Information” in this prospectus may not occur and actual results could differ materially from those anticipated or implied in the forward-looking statements.prospectus.

USE OF PROCEEDS

All securities sold pursuant to this prospectus will be offered and sold by the selling securityholders. We will not receive any of the proceeds from the sale of the shares of common stock by the selling stockholders. All proceedssecurityholders of the securities offered hereby.

SELLING SECURITYHOLDERS

This prospectus covers (i) 33,350,136 shares of our Class A Common Stock and (ii) 17,719,598 Class A Warrants, each to purchase 0.190 shares of our Class A Common Stock, subject to adjustment pursuant to the terms thereof ((i) and (ii) together, the “Securities”). The Securities were issued in a private placement transaction exempt from the saleregistration requirements of the commonSecurities Act pursuant to Regulation D thereunder and in a stock offered in this offering will be for the accountdividend effected on December 17, 2015. We have entered into a Registration Rights Agreement with each of the selling stockholders.

15

PRICE RANGE OF COMMON STOCK
securityholders to register the resale of the Securities by the selling securityholders.

 Our common stock

The selling securityholders may from time to time offer and sell pursuant to this prospectus any or all of the Securities set forth below. However, the selling securityholders are under no obligation to sell any of the Class A Common Stock or Class A Warrants offered pursuant to this prospectus. As used in this prospectus, the term “selling securityholders” includes the selling securityholders listed in the table below, as well as permitted transferees, pledgees, donees, assignees, successors and others who later come to hold any of the selling securityholders’ interests in the Securities, other than through a public sale pursuant to this prospectus or Rule 144 under the Securities Act.

Beneficial ownership for the purposes of the following table is listeddetermined in accordance with the rules and tradedregulations of the SEC. These rules generally provide that a person is the beneficial owner of securities if such person has or shares the power to vote or direct the voting of securities, or to dispose or direct the disposition of securities or has the right to acquire such powers within 60 days. In some cases, we believe that foreign ownership or other restrictions may limit the ability of warrantholders to exercise Class A Warrants they hold, meaning that such person may not be required, under relevant rules and regulations, to report beneficial ownership as they would not be entitled to receive the underlying shares of Class A Common Stock.

Except as disclosed in the footnotes to these tables and subject to applicable community property laws, we believe that each beneficial owner identified in the table possesses sole voting and investment power over all Class A Common Stock shown as beneficially owned by the beneficial owner. The information with respect to beneficial ownership by the selling securityholders was prepared based on information supplied by such stockholders to us. Unless otherwise indicated in the table or footnotes thereto, the address for each beneficial owner is c/o Overseas Shipholding Group, Inc., 600 Third Avenue, 39^th Floor, New York, Stock Exchange and the Pacific Stock Exchange under the symbol "OSG." New York 10016.

Selling Securityholders

The following table sets forth for the periods indicated, the price range of our common stock as reported on the New York Stock Exchange.

    Prices shown in the table are the high and low closing prices on the New York Stock Exchange by quarter.

    On June 14, 2001, the last reported sales price of our common stock on the New York Stock Exchange was $30.79 per share. As of June 1, 2001, there were approximately 1,018 stockholders of record. We believe there are approximately 2,100 beneficial owners of our common stock.

DIVIDEND POLICY

    We have continuously paid cash dividends since 1974 and we have paid a regular quarterly cash dividend of $0.15 per share of common stock for each of the quarters during the last two years. The payment of cash dividends in the future will depend on our operating results, cash flow, working capital requirements and other factors deemed relevant by our Board of Directors.

16

CAPITALIZATION

    The following table summarizes our capitalization as of March 31, 2001. You should read the information in this table together with our consolidated statements and the related notes and with "Selected Consolidated Financial Data" and "Management's Discussion and Analysis of Financial Condition and Results of Operations" included elsewhere in this prospectus.