Barry Dennis Roy

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Barry Dennis Roy, 73, of Chilmark passed away peacefully on August 9, 2019, at Tufts Medical Center in Boston. Born on Sept. 6, 1945, in Norwich, Conn., he was the only child of Emory and Bernice (Baril) Roy, and spent his youth in Taftville, Conn. During these years Barry grew to love the scouting experience, eventually leading him to become an Eagle Scout.

Barry was a 1967 graduate of Saint Michael’s College in Colchester, Vt., with his summers spent working on Cape Cod in Falmouth. He treasured the many lifelong friendships that he made during his time at St. Mike’s, his friends becoming his “Band of Brothers” for the next 50 years.

After St. Mike’s, he graduated from Albany Law School in 1971, followed by a master’s in taxation (LL.M.) from Boston University School of Law. From 1974 to 1980 Barry worked in the Office of Chief Counsel for the Internal Revenue Service. He joined Deloitte as a tax partner in 1981, serving many multinational clients, and was named national director of tax quality assurance in 1996. He retired in 2009. 

Barry was an avid supporter of many charities, including the Miami Project to Cure Paralysis, Compassionate Care ALS, and the Aquinnah Lighthouse project of the Wampanoag Nation on Martha’s Vineyard. He was also a trustee of Saint Michael’s College, and chair of the investment committee. Barry loved his alma mater, and was a dedicated alumnus through both his philanthropy and volunteer work. 

Barry was fondly called “the Bear” by those who knew and loved him. He was larger than life, and lived with the biggest of hearts and immense generosity. He filled the room with love and laughter, and became a beloved member of many families, with more than a dozen godchildren. As an only child, he is survived by numerous cousins, their children, godchildren, and dear friends who all became his chosen family.

The sunsets are not quite as vivid and the moon not quite as bright over the Vineyard Sound without him, but lives are fuller for all who knew him.

A celebration of life will be held at Saint Michael’s College in Colchester on Oct. 12 at 11 am. In lieu of flowers, donations can be made to “The Barry Roy Memorial Fund,” Saint Michael’s College, 1 Winooski Park, Colchester, VT 05439, or bit.ly/StMikeDonation. Condolences may be sent to PO Box 171, Chilmark, MA 02535. For information and online guestbook, please visit dolanfuneral.com.