Obituaries 10-20-2022

Thomas Patrick May

He Will be Sorely Missed

Thomas Patrick May of Palm Harbor, Florida, formerly of Winthrop, passed away suddenly on October 11. He was 74 years old.

Born in Buffalo, NY, the first of eight children of his late parents, James and Norma (Shephard) May.

He was the beloved husband of Carol Ann May of Palm Harbor, FL. and he also leaves behind his son, Timothy May, daughter-in-law, Karen and grandchildren, Meaghan and Peter of Framingham as well as his former spouse, Dorothy (Kudrick) May; brothers: William, Daniel, Peter, Donald and Michael, sister, Joan McDonnell and his late brother, Richard. Tom is also survived by his wife Carol’s children: Robert O’Donnell and his wife, Anne and Maureen O’Donnell, all of Quincy, Sean O’Donnell and his wife, Morgan of Washington D.C. and Brian O’Donnell and his wife, Taniya of Milton.

Tom grew up in Dorchester and Hyde Park and was a graduate of Don Bosco Technical High. He used his Graphic Arts major in a very successful career in Print Sales and Estimating. He taught Print Estimating at Northeastern University and was a long-time member of the printing industries Craftsman Club, a member of the Dunedin Golf and Country Club and a long-time past member of the Cottage Park Yacht Club. He was also the former vice president of Mass Bay Sailing Offshore.

Tom was an avid sportsman enjoying great accomplishments in basketball, golf and sailing. 

At 6’5”, Tom was the reserve center for Bosco and played a key role in a near upset win in the Tech Tourney against Melrose High in the old Boston Garden. Golf and Sailing were also a big part of Tom’s life. A long ball 300-yard driver led to a very good scoring average in the high 70’s, 7 holes in one and a sandbagging 9 handicap.

But his sailing exploits with son, Timmy and brother, Billy led to a room full of trophies with too many wins to mention aboard his boats, Sailsman and Hound Dog, as well as a regular crew and backup driver on Dick Hyde’s, Freightrain.

Affectionately known as Tommy Mo, The Big Dog, The Dancing Bear and Pop, Tom will be sorely missed.

His funeral will be held from the Maurice W. Kirby Funeral Home, 210 Winthrop St., Winthrop today, Thursday, October 20 at 9 a.m. followed by a Funeral Mass in St. Michaels Parish-Winthrop at 10 a.m. Relatives and friends are invited. Interment will be private. Donations in his memory can be made to Make-A-Wish 133 Federal St. 2nd  Floor, Boston, MA 02110.

For guestbook, please visit:

Richard Tewksbury

He Was a Friend to All

Richard O. Tewksbury of Revere and formerly of Winthrop passed away suddenly at the Massachusetts General Hospital in Boston on October 15. He was 40 years old.

Born in Boston, the beloved son of Felicia (Simione) and Richard E. Tewksbury, he previously worked as a Sales Manager for Mcgee Motor Cars and was a proud graduate of the NADA Dealer Academy. He was also a member of the Winthrop Yacht Club.

He was an avid lover of all types of music and going to concerts. He was also a huge Boston sports fan.

There was never a room that his big smile and spirit wouldn’t light up. He was a friend to all.

He was the loving father of Olivia M. Tewksbury and the dear brother of Joseph R. Tewksbury of Revere. He is also survived by his step-daughter, Mackenzie Coles and his girlfriend, Kellie Long.

The funeral will be conducted from the Caggiano-O’Maley-Frazier Funeral Home, Winthrop,  today,  Thursday, October 20 at 10:30 a.m. followed by a Funeral Mass in St. John the Evangelist Church, 320 Winthrop St., Winthrop at 11:30 a.m. Services will conclude with the interment in Winthrop Cemetery.

For directions or to sign the online guestbook, go to

Pauline Rielly

Member of the Telephone Pioneers and the Winthrop Catholic Women’s Club

Pauline M. Rielly of Winthrop, formerly of East Boston, passed away at the Brudnick Center for Living in Peabody on October 13. She was 98 years old.

She was born in Boston, the beloved daughter of the late Ellen R. (Hartery) and Edward J. Barron. A resident of Winthrop for over 30 years, she worked as a telephone operator for New England Telephone prior to her retirement. She was also a member of the Telephone Pioneers and the Winthrop Catholic Women’s Club.

She was the devoted wife of the late Robert Rielly and the loving mother of Kathleen Gallo and her late husband, Francis of Hooksett, New Hampshire, Pauline Boland and her husband, James of Peabody, Patricia Imbrogno and her husband, Joseph of Lynnfield and James Rielly and his wife, Michelle of Windsor, Vermont; dear sister of the late Rita Barron, Ellen Barron, Edward Barron and Paul Barron. She is also survived by her beloved sister-in-law, Mary L. Barron and cousin, Ellen Naughton. She was the cherished grandmother to seven and great grandmother to six.

The funeral was conducted from the Caggiano-O’Maley-Frazier Funeral Home, Winthrop on Tuesday, October 18 followed by a Funeral Mass in St. John the Evangelist Church, Winthrop. Rev. Patrick O’Connor celebrated the mass and offered prayers at the interment in the Holy Cross Cemetery in Malden.

To sign the online guestbook, go to

Dorothy Simonini

Retired Administrative Assistant to the Principal of the Dom Savio Preparatory School

Dorothy (Cataldo) Simonini of Peabody, formerly of Revere, passed away peacefully on October 11. The beloved mother of Paul Simonini and his wife, Donna and daughter-in-law, Beverley, all of Peabody, Dorothy is also survived by her sister-in-law, Dorothea Simonini of East Boston and two nephews, A. Henry Latorella (Cathy) and Jon Latorella (Caroline and Megan.) Dorothy was predeceased by her beloved husband, George, son, Donald, sister, Cecelia Latorella, her mother, Francis Bolino Cataldo and her father, Joseph Cataldo. In addition to raising two boys with her husband, George, she enjoyed a career that spanned 31 years during which time she was the Administrative Assistant to the Principal at Dom Savio Preparatory School in East Boston. She was affectionately known simply as “Mrs. Sim” to many of the students she encountered over the years.
After retiring, Dorothy moved to an Independent Living community in Danvers, where she rekindled her interest in painting, much to the joy of the many people with whom she shared her painting. At age 94, her re-found talent culminated in her winning a state-wide contest to redesign the logo for the Massachusetts Assisted Living Association (Mass-ALA). Dorothy certainly lived a full life and she will be missed by all those she touched for nearly a century. Visiting hours were held in the Maurice W. Kirby Funeral Home, 210 Winthrop St., Winthrop on Friday, October 14, from 9 to 12 p.m. followed by a funeral service in the funeral home beginning at 12 Noon. Interment followed in Winthrop Cemetery. Donations in her memory can be made to Care Dimensions, 75 Sylvan St., Danvers, MA. 01923. To sign Dorothy’s guestbook, please visit: 

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