NEW YORK –
Overseas Shipholding Group, Inc. (NYSE MKT:OSG, OSGB) (the “Company” or
“OSG”) announced today that, in connection with the previously-announced
settlement of the Company’s lawsuit against Proskauer Rose LLP, on April
28, 2016 its Board of Directors declared a dividend of $0.17968 per
outstanding Class B common share, and in conjunction with that dividend
will make a cash distribution of $0.17968 per outstanding warrant for
OSG’s Class B common stock (“Class B warrants”).

On May 13, 2016, all holders of record of OSG’s Class B common stock and
Class B warrants as of 5:00 p.m. EDT on May 9, 2016 (the “record date”),
will receive $0.17968 per outstanding Class B common share and
outstanding Class B warrant held by them as of the record date. In
accordance with the terms of the Class B warrants, holders of those
warrants will receive the cash distribution but the warrants will not
otherwise be adjusted in any manner in connection with the payment of
the dividend on the Class B stock.

Pursuant to the terms of OSG’s certificate of incorporation, each share
of Class B common stock will thereafter automatically convert into one
share of Class A common stock as of 5:00 p.m. EDT on May 27, 2016 (the
“conversion date”), the tenth business day after the payment of the
dividend and distribution to the holders of Class B securities described
above. In addition, pursuant to the terms of the warrant agreement
governing the Class B warrants, each outstanding Class B warrant will
automatically convert into a Class A warrant on the conversion date.
Each Class A warrant is currently exercisable for 1.142 shares of Class
A common stock. In connection with the conversion, holders of
certificated Class B securities may be requested to furnish certain
information to OSG’s conversion agent. After the conversion date, OSG
will have only a single class of common stock outstanding, trading under
the symbol “OSG”.

“We are very pleased to be paying a distribution to Class B stockholders
and warrantholders in connection with the final settlement of the
Proskauer lawsuit, meeting our obligation to return a percentage of the
proceeds to our Class B securityholders and simultaneously simplifying
our capital structure,” said Captain Ian T. Blackley, OSG’s president
and CEO. “We remain focused on executing on our strategy and delivering
value for our shareholders.”

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.

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 declaration and timing of future
dividends, if any, will be at the discretion of the Company’s Board of
Directors and will depend upon, among other things, the Company’s future
operations and earnings, capital requirements, general financial
condition, contractual restrictions, restrictions imposed by applicable
law or regulation, and such other factors as the Board may deem
relevant. 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.

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