OREANDA-NEWS. May 24, 2016. Overseas Shipholding Group, Inc. (NYSE MKT:OSG, OSGB) (the “Company” or “OSG”) announced today that it was added to the Wilshire 5000 Total Market IndexSM (Wilshire 5000) effective after the markets’ close on Friday, May 20, 2016 in conjunction with the monthly additions and deletions of the index.

“We are very pleased with our inclusion in the Wilshire 5000 Total Market IndexSM,” said Captain

Ian T. Blackley, OSG’s president and CEO. “The addition of OSG to the Wilshire 5000 will enhance our visibility within the investment community and provide an opportunity to broaden our shareholder base.”

The Wilshire 5000, the original pure and complete measure of the U.S. stock market, was developed in 1974 by

Dennis A. Tito, chairman and chief executive officer of Wilshire Associates Incorporated (Wilshire®). It is widely considered the best way to track the broad U.S. equities market and estimate market value changes. More information about the Wilshire 5000 can be found at www.wilshire.com/indexinfo.

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.

About Wilshire Associates

Wilshire Associates, a leading global, independent investment consulting and services firm, provides consulting services, analytics solutions and customized investment products to plan sponsors, investment managers and financial intermediaries. Its business units include, Wilshire Analytics, Wilshire Consulting, Wilshire Funds Management and Wilshire Private Markets.

The firm was founded in 1972, providing revolutionary technology and acting as an early innovator in the application of investment analytics and research to investment managers in the institutional marketplace. Wilshire also is credited with helping to develop the field of quantitative investment analysis that uses mathematical tools to analyze market risks. All other business units evolved from Wilshire’s strong analytics foundation. Wilshire developed the Wilshire 5000 Total Market Indexand became an early innovator in creating integrated asset/liability analysis/simulation models as well as practical models in risk budgeting through beta and active risk analysis. Wilshire has grown to a firm of approximately 300 employees serving the needs of investors around the world.

Based in Santa Monica, California, Wilshire serves in excess of 500 clients across 20 countries with combined assets exceeding \\$8 trillion*. With ten offices on four continents, Wilshire Associates and its affiliates are dedicated to providing clients with the highest quality counsel, products and services. Wilshire® and Wilshire 5000® are registered service marks of Wilshire Associates Incorporated. Wilshire 5000 Total Market Index?, Wilshire US Micro-Cap Index?, Wilshire US Large-Cap Value Index?, Wilshire US Large-Cap Growth Index?, Wilshire US Small-Cap Growth Index? and Wilshire US Small-Cap Value Index?, Wilshire US Real Estate Securities Index? and Wilshire ex-US Real Estate Securities Index? are service marks of Wilshire Associates Incorporated.

*Client assets are as represented by Pensions and Investments, detailed in P&I’s “Largest Retirement Funds” and P&I’s “Largest Money Managers (U.S. institutional tax-exempt assets)” as of 9/30/14 and 12/31/14, and published 2/9/15 and 5/18/15, respectively).

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 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.