Barry Dennis Roy, of Chilmark, died on August 9 at the Tufts Medical Center in Boston. He was 73.

Born on September 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 scouting, eventually leading him to become an Eagle Scout.

Barry was a 1967 graduate of Saint Michael’s College in Colchester, Vt. During his school years he spent his summers working in Falmouth. He treasured the friendships that he made during his time at St. Mike’s, many of whom became his “Band of Brothers” for the next 50 years.

After St. Mike’s, he graduated from Albany Law School in 1971 and then received a masters in taxation (LLM) 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 and 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, Vt., on October 12, 2019 at 11 a.m.

In lieu of flowers, memorial donations can be made to Saint Michael’s College, “The Barry Roy Memorial Fund”. Saint Michael’s College, One Winooski Park, Colchester, VT 05439. Condolences may be sent to PO Box 171, Chilmark, MA 02535. For information and online guestbook, please visit