NEW YORK –
Overseas Shipholding Group, Inc. (NYSE MKT:OSG, OSGB) (the “Company” or
“OSG”) announced today that it was added to the Wilshire 5000 Total
Market Index^SM (Wilshire 5000) effective after the markets’
close on Friday, May 20, 2016 in conjunction with the monthly additions
and deletions of the index.

“We are very pleased with our inclusion in the Wilshire 5000 Total
Market Index^SM,” said Captain Ian T. Blackley, OSG’s
president and CEO. “The addition of OSG to the Wilshire 5000 will
enhance our visibility within the investment community and provide an
opportunity to broaden our shareholder base.”

The Wilshire 5000, the original pure and complete measure of the U.S.
stock market, was developed in 1974 by Dennis A. Tito, chairman and
chief executive officer of Wilshire Associates Incorporated (Wilshire®).
It is widely considered the best way to track the broad U.S. equities
market and estimate market value changes. More information about the
Wilshire 5000 can be found at www.wilshire.com/indexinfo.

About OSG

Overseas Shipholding Group, Inc. (NYSE MKT:OSG, OSGB) is a publicly
traded tanker company providing energy transportation services for crude
oil and petroleum products in the U.S. and International Flag markets.
OSG is committed to setting high standards of excellence for its
quality, safety and environmental programs. OSG is recognized as one of
the world’s most customer-focused marine transportation companies and is
headquartered in New York City, NY. More information is available at www.osg.com.

About Wilshire Associates

Wilshire Associates, a leading global, independent investment consulting
and services firm, provides consulting services, analytics solutions and
customized investment products to plan sponsors, investment managers and
financial intermediaries. Its business units include, Wilshire
Analytics, Wilshire Consulting, Wilshire Funds Management and Wilshire
Private Markets.

The firm was founded in 1972, providing revolutionary technology and
acting as an early innovator in the application of investment analytics
and research to investment managers in the institutional marketplace.
Wilshire also is credited with helping to develop the field of
quantitative investment analysis that uses mathematical tools to analyze
market risks. All other business units evolved from Wilshire’s strong
analytics foundation. Wilshire developed the Wilshire 5000 Total Market
Index and became an early innovator in creating integrated
asset/liability analysis/simulation models as well as practical models
in risk budgeting through beta and active risk analysis. Wilshire has
grown to a firm of approximately 300 employees serving the needs of
investors around the world.

Based in Santa Monica, California, Wilshire serves in excess of 500
clients across 20 countries with combined assets exceeding $8 trillion*.
With ten offices on four continents, Wilshire Associates and its
affiliates are dedicated to providing clients with the highest quality
counsel, products and services. Wilshire^® and Wilshire 5000^®
are registered service marks of Wilshire Associates Incorporated.
Wilshire 5000 Total Market Index , Wilshire US Micro-Cap Index ,
Wilshire US Large-Cap Value Index , Wilshire US Large-Cap Growth Index ,
Wilshire US Small-Cap Growth Index and Wilshire US Small-Cap Value
Index , Wilshire US Real Estate Securities Index and Wilshire ex-US
Real Estate Securities Index are service marks of Wilshire Associates
Incorporated.

*Client assets are as represented by Pensions and Investments, detailed
in P&I’s “Largest Retirement Funds” and P&I’s “Largest Money Managers
(U.S. institutional tax-exempt assets)” as of 9/30/14 and 12/31/14, and
published 2/9/15 and 5/18/15, respectively).

Forward-Looking Statements

This release contains forward-looking statements. In addition, the
Company may make or approve certain statements in future filings with
the Securities and Exchange Commission (SEC), in press releases, or in
oral or written presentations by representatives of the Company. All
statements other than statements of historical facts should be
considered forward-looking statements. These matters or statements may
relate to the Company’s plans to issue dividends and make payments to
securityholders, its prospects, including statements regarding trends in
the tanker and articulated tug/barge markets, and possibilities of
certain strategic alliances and investments. Forward-looking statements
are based on the Company’s current plans, estimates and projections, and
are subject to change based on a number of factors. Investors should
carefully consider the risk factors outlined in more detail in the
Company’s Annual Report for 2015 on Form 10-K under the caption “Risk
Factors” and in similar sections of other filings made by the Company
with the SEC from time to time. The Company assumes no obligation to
update or revise any forward-looking statements. Forward-looking
statements and written and oral forward looking statements attributable
to the Company or its representatives after the date of this release are
qualified in their entirety by the cautionary statements contained in
this paragraph and in other reports previously or hereafter filed by the
Company with the SEC.

View source version on businesswire.com: http://www.businesswire.com/news/home/20160523006123/en/

Investor Relations & Media:
Overseas Shipholding Group,
Inc.
Brian Tanner, 212-578-1645
btanner@osg.com