Overseas Shipholding Group Inc. Exercises Option for Second 204,000 Barrel Barge at Gunderson Marine LLC

Overseas Shipholding Group, Inc. (NYSE: OSG) (the “Company” or “OSG”) a provider of energy transportation services for crude oil and petroleum products in the U.S. Flag markets, announced today that it has exercised an option to construct a second 204,000 barrel Oil and Chemical ATB Barge at Gunderson Marine LLC’s (“GM”) Portland, Oregon facility. The barge, scheduled for delivery in the second half of 2020, will be designed and built to be paired with one of the Company’s existing modern tugs, replacing a rebuilt barge unit which is expected to be phased out of service prior to delivery of the new barge. Each of the two barges contracted with GM will be of identical design, meeting all of the latest safety and environmental requirements. The Company intends to finance the construction of the two barges at GM with a combination of existing cash and future debt financing.

“OSG is pleased to have taken this step to further ensure a continued leading presence in the US Flag petroleum transportation sector,” said Sam Norton, OSG’s President and CEO. “The larger barge capacity offered by OSG’s Gunderson design, as compared to most of the other available modern units, should give our barges a competitive edge on a dollar per delivered barrel cost across almost all voyages. With the addition of these modern, efficient and environmentally responsible vessels to our existing fleet, we have increased confidence in our ongoing ability to offer our core customer base both the assets and the quality of service that they demand.”

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 21 vessel U.S. Flag fleet consists of five ATBs, two lightering ATBs, three shuttle tankers, nine MR tankers, and two non-Jones Act MR tankers that participate in the U.S. MSP. In addition to the currently operating fleet, OSG has on order two additional non-Jones Act MR tankers and two Jones Act compliant barges which are scheduled for delivery in 2019 and 2020 respectively. 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; Non-GAAP Financial Measures

This release contains forward-looking statements. In addition, OSG 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 OSG. All statements other than statements of historical facts should be considered forward-looking statements. These matters or statements may relate to OSG’s prospects, OSG’s future results of operations, OSG’s ability to maintain its market position, OSG’s ability to operate without interruption, OSG’s ability to pursue growth opportunities, and OSG’s ability to comply with the terms of its credit facilities and other material contracts. Forward-looking statements are based OSG’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 OSG’s Annual Report on Form 10-K and in similar sections of other filings made by OSG with the SEC from time to time. OSG 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 OSG with the SEC. “TCE revenue” and “net annual vessel operating contribution” are non-GAAP financial measures, which are defined in OSG’s most recent Quarterly Report on Form 10-Q and the related earnings release, a copy of which was filed as an Exhibit to OSG’s Current Report on Form 8-K filed with the SEC on November 9, 2018. These Non-GAAP measures are used because management makes economic decisions, and evaluates OSG’s financial performance, based on these measures.

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