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Dec 4, 2017

Overseas Shipholding Group Announces CFO Appointment

TAMPA, Fla. –
Overseas Shipholding Group, Inc. (NYSE:OSG) (“OSG”) announced today that
Richard L. Trueblood was appointed Chief Financial Officer on December
1, 2017. Mr. Trueblood has been serving as OSG’s interim CFO since July.

Mr. Trueblood is a CPA with over 45 years of experience, holding a
Bachelor of Science degree in accounting from Bentley University. His
broad range of financial and executive experience includes serving as a
Florida CFO Group Partner, as Chief Financial Officer at the technology
start-up companies Heliotrope Technologies, Inc., Advent Solar Inc., and
Troon Golf LLC, and as SVP Finance at NYSE listed Promus Hotel
Corporation. Mr. Trueblood was a partner at KPMG where he provided
extensive services to clients in strategic business management, mergers
and acquisitions, SEC compliance, secondary debt and equity securities
offerings, as well as leading KPMG’s real estate practices in Boston,
Massachusetts and Orange County, California. He also served as a
director for UMB Bank Arizona, N.A. for eight years.

“I am very pleased that Dick is joining OSG as CFO,” said Sam Norton,
OSG’s President and CEO. “In his role as interim CFO since July, Dick
has proven to be a valuable member of the management team who has worked
tirelessly to contribute to the extensive agenda undertaken by the
finance team. I look forward to his continuing contributions as we move
forward in implementing our business plan.”

“I have enjoyed working with the OSG team and gotten to know its
business well,” said Trueblood. “It is certainly exciting to be with a
leading U.S. Flag shipping company with a reputation of being a trusted
operating franchise. OSG has a diversified portfolio in the Jones Act
market and strong financial profile, and I hope to contribute to its
future.”

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 22 active vessel U.S.
Flag fleet consists of six active 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. All statements other
than statements of historical facts should be considered forward-looking
statements. 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 and subsequent Form 10-Q filings. The Company assumes no obligation
to update or revise any forward-looking statements.

Investor Relations & Media:
Overseas Shipholding Group,
Inc.
Susan Allan, 813-209-0620
sallan@osg.com