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Thomas J. O'Leary, Jr.

Pause Best of Times by Bruce H. Zimmerman (ASCAP)
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Memories & Candles

“Dear Gail. sympathy to you and family. So sad for your loss. My prayersand thoughts are with you. Nick ”
1 of 11 | Posted by: NICHOLAS FERRI - sherborn, MA

“We are so sorry for your loss - Tom was a great guy and he loved Gail and Dana and his beautiful grandsons so much. I know he will be watching over...Read More »
2 of 11 | Posted by: Kristen Harding - Sugar Land, TX

“So sorry for your loss of Tom. We grew up in North Cambridge and went all through school together. I have many wonderful memories of Tom, he was a...Read More »
3 of 11 | Posted by: David Errico - Cocoa, FL

“Sending condolences and prayers to your family. I went to North Cambridge Catholic High with Tommy and he was a great friend Rest In PeaceJan ”
4 of 11 | Posted by: Jan Dedrick Foley - Winchester, MA

“Rest in Peace Tom. I will pray for your soul. Have'nt seen you since graduation 1963. You were quiet in school and highly regarded. But you seem to...Read More »
5 of 11 | Posted by: Kevin O'Connor - Classmate

“Tom was a pleasure to be with, always, down to earth, warm, cheerfully interested in whatever you were interested in, and yes, he liked to talk as...Read More »
6 of 11 | Posted by: Jonathan Winer - Bethesda, MD

“Tom was a great friend, mentor, and always the center of laughter in every circle. The world has lost a another great man. You are all in my thoughts...Read More »
7 of 11 | Posted by: Paul Morris - Friend

“Tom and Gail have been great friends to my family, especially Mimi for so many years. We are so sorry that Tom has left us, and grateful for all his...Read More »
8 of 11 | Posted by: Joshua Winer - Waltham, MA

“Hi Gail,So sorry to hear of your loss. Thank you for your decades of assistance to Mimi. From reading about your husband, it appears you both were...Read More »
9 of 11 | Posted by: David Feldman - Dedham, MA

“We had so many terrific times together. You were a true friend. You were always in a good mood and ready to have fun. You were a wonderful brother,...Read More »
10 of 11 | Posted by: Bob and Betty Millen - Cape Coral, FL

“You'll be missed by everyone and forgotten by no one. ”
11 of 11 | Posted by: Bob and Betty Millen - Cape Coral, FL


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.