TAMPA, Fla. –
Overseas Shipholding Group, Inc. (NYSE: OSG) (“OSG”), a provider of
energy transportation services for crude oil and petroleum products in
the U.S. Flag markets, announced today that two of its subsidiaries have
closed on a financing from Wintrust Commercial Finance, a division of
Wintrust Asset Finance Inc., in the amount of $27,500,000. This loan is
secured by first preferred ship mortgages on the Overseas Mykonos and
Overseas Santorini, and a guaranty from OSG.

“We are very pleased to have completed this financing, as anticipated
and discussed in our earnings call on November 9,” stated Dick
Trueblood, OSG’s Chief Financial Officer. “Securing this financing is
one piece of our overall plan to refinance our term loan debt. We
appreciate working with the team at Wintrust in putting this deal
together.”

“We’re proud to partner with OSG in providing capital for the refinance
of the vessels,” stated Kirk Phillips, President and CEO of Wintrust
Commercial Finance. “Our team led by Garrett Wilkins, Justin Piot, and
Joe Gensor demonstrated Wintrust Commercial Finance’s understanding of
the industry and commitment to working closely with our customers in
meeting their unique financing needs and building long term
relationships.”

Sam Norton, OSG’s Chief Executive Officer, stated, “The Overseas Mykonos
and Overseas Santorini are the only two oil tankers that participate in
the U.S. Maritime Security Program and this transaction gives us the
flexibility to continue this participation.”

About Wintrust Financial Corporation

Wintrust is a financial holding company with assets of over $30 billion
whose common stock is traded on the NASDAQ Global Select Market. Built
on the “HAVE IT ALL” model, Wintrust offers sophisticated technology and
resources of a large bank while focusing on providing service-based
community banking to each and every customer. Wintrust operates 15
community bank subsidiaries, with over 160 banking locations located in
the greater Chicago and southern Wisconsin market areas. Additionally,
Wintrust operates various non-bank business units including business
units which provide commercial and life insurance premium financing in
the United States, a premium finance company operating in Canada, a
company providing short-term accounts receivable financing and
value-added out-sourced administrative services to the temporary
staffing services industry, a business unit engaging primarily in the
origination and purchase of residential mortgages for sale into the
secondary market throughout the United States, and companies providing
wealth management services.

About Overseas Shipholding Group, Inc.

Overseas Shipholding Group, Inc. (NYSE:OSG) is a publicly traded 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 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 as defined under the
federal securities laws. Words such as “plan”, “may”, “should”,”
believes”, “estimates”, “targets”, “anticipates” and similar expressions
generally identify forward-looking statements; however, statements other
than statements of historical facts should be considered forward-looking
statements. Forward-looking statements are based on OSG’s current plans,
estimates and projections, and are subject to change based on a number
of factors. Investors should also carefully consider the risk factors
outlined in more detail in the Annual Report on Form 10-K for OSG and in
similar sections of other filings made by OSG 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 OSG 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 OSG with the SEC.

View source version on businesswire.com: https://www.businesswire.com/news/home/20181126005683/en/

Media Contacts:
Wintrust Commercial Finance
Kirk S.
Phillips, President & CEO
kphillips@wintrust.com
469-777-5656

Overseas Shipholding Group, Inc.
Susan Allan, VP, General Counsel
813-209-0620
sallan@osg.com