Dec 5, 2016

Overseas Shipholding Group Announces Leadership Transition

TAMPA, Fla. –
Overseas Shipholding Group, Inc. (NYSE:OSG) (the “Company” or “OSG”)
announced today that Christopher Wolf will become the Senior Vice
President and Chief Financial Officer of the Company on December 29,
2016, taking over from Rick F. Oricchio. From December 1 to December 29,
Mr. Wolf will serve as the Chief Financial Officer of OSG’s subsidiary,
Overseas Bulk Ships, Inc.

In addition, Susan Allan has been appointed to serve as Vice President,
General Counsel and Corporate Secretary of the Company. Ms. Allan is
replacing James D. Small III, who became the Chief Administrative
Officer, Secretary and General Counsel of International Seaways, Inc.,
following the completion of its spin-off from OSG on November 30, 2016.
The Company has moved its corporate headquarters to Tampa.

Sam Norton, OSG’s SVP & President and CEO of the U.S. Flag Strategic
Business Unit said, “I am pleased to welcome both Chris and Susan to
OSG. It is an exciting time in the Company’s history, and their
experience and fresh perspective will complement and enhance our
existing management team’s strengths and capabilities.”

“This is a pivotal time to be joining OSG, a company with both a rich
history and a compelling future,” Wolf said. “I look forward to working
with the leadership team to advance the Company’s strategy and drive
shareholder value.”

Ms. Allan added, “I am pleased to be part of the OSG leadership team as
the Company begins to navigate this next chapter and drive its future
success.”

Christopher Wolf Details

Mr. Wolf has extensive experience as a Chief Financial Officer, having
served in this role at several companies-both publicly-listed as well as
privately-owned-including most recently at Higher One Holdings, Inc., a
publicly-traded provider of technology-based refund disbursement,
payment processing and data analytics services to higher education
institutions and students, where he worked from 2013 to 2016. Earlier in
his career, Mr. Wolf was a Chief Financial Officer at Acxiom Corporation
and Catalina Marketing. He began his career at Arthur Andersen, LLP. Mr.
Wolf received his B.S. in Accounting from Florida State University and a
Master of Accounting from the University of North Carolina. Mr. Wolf is
a Certified Public Accountant.

Susan Allan Details

Ms. Allan comes to OSG from Jabil Circuit, Inc., where she was Vice
President and Assistant Corporate Secretary since 2009. Jabil is a
publicly listed, global electronic and technology solutions company
providing design and manufacturing product management services. From
1997 to 2009, she was senior counsel at Tech Data Corporation, also a
publicly traded company and one of the world’s largest wholesale
distributors of technology products, services and solutions. Ms. Allan
has significant experience in corporate governance matters, as well as
experience with capital markets offerings and mergers and acquisitions.
Ms. Allan received her B.A. from George Mason University and her law
degree from the University of Southern California. She is a member of
the Bars of Florida and the District of Columbia.

About Overseas Shipholding Group, Inc.

Overseas Shipholding Group, Inc. (NYSE:OSG) is a publicly traded tanker
company providing energy transportation services for crude oil and
petroleum products in the U.S. Flag markets. OSG is a major operator of
tankers and ATBs in the Jones Act industry. OSG’s 24-vessel U.S. Flag
fleet consists of eight ATBs, two lightering ATBs, three shuttle
tankers, nine MR tankers, and two non-Jones Act MR tankers that
participate in the U.S. Maritime Security Program. 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
Tampa, FL. 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 prospects, its ability to retain and effectively
integrate new members of management, and the effect of the Company’s
spin-off of International Seaways, Inc. Forward-looking statements are
based on each of 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
Annual Report on Form 10-K for OSG and the Registration Statement on
Form 10 for International Seaways, Inc. and in similar sections of other
filings made by each of the Companies 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.

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