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1945 Thomas 2020

Thomas J. O'Leary

January 31, 1945 — November 14, 2020

Tom O'Leary wanted to be remembered as just a 'regular guy' . . . but he was anything but.

Kind, generous, optimistic, and loyal are just some of the many words that described a man who constantly lived his life for others, whether it was for friends, family, or even a complete stranger. Known for his approachable and affable demeanor, he will be dearly missed by all who knew and loved him.

Mr. Thomas J. O'Leary, Jr., of Weston, died on Saturday, November 14, 2020 in Brigham and Woman's Hospital in Boston. He was 75.

Tom was born in Cambridge on January 31, 1945 to the late Dorothy (Hanley) and Thomas J. O'Leary, Sr. He was a graduate of North Cambridge Catholic High School and had worked in technology sales for many years until his retirement. He married Weston native Gail B. Chisholm forty-six years ago and the pair made Weston their lifelong home.

In recent years Tom spent his time driving the Jesuits at the Campion Center and for the Sisters of Charity, taking them to and from appointments, running errands, and more. It wasn't long before he quickly became a familiar face and trusted friend to many. Tom had 'the gift of gab' and loved making people laugh. Although he kept busy doing the things he loved, the center of his world and the highlight of his life were being around his grandsons. They were his absolute pride and joy. Tom was a wonderful cook and loved sharing meals with family and friends. He and Gail and their daughter, Dana, made many happy memories on their many Cape Cod getaways.

In addition to his wife, Gail, he leaves his daughter, Dana Reese (Jim) of Sudbury, his grandsons, Teddy and Chase Reese; his sisters, Dorothea Glew (Dick) and Mary Rose Card (Mal) and many dear nephews.

Funeral services are private. Once restrictions have been lifted, a celebration of Tom's wonderful life will be held.

Memorial donations may be made to the Sisters of Charity, c/o Elizabeth Seton Residence, 125 Oakland Street, Wellesley, Massachusetts 02481, www.elizabethseton.org, or to a charity of one's choice.
To order memorial trees or send flowers to the family in memory of Thomas J. O'Leary, please visit our flower store.

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