Legal 02

Robert J Sheffield

August 21, 1941 ~ February 7, 2021 (age 79)




Robert J. (Bob) Sheffield passed away at home on February 7, 2021, surrounded by his adoring family while watching Sunday Mass on TV. He was predeceased by the love of his life, his wife, Mary, in 2019, after 55 years of marriage.

Bob was the loving father of Rob Sheffield, and wife Ally, of Brooklyn, NY; Ann Sheffield, and partner John Grub, of Weymouth; Tracey Mackey, and husband Bryant, of Zurich, Switzerland; and Caroline Hanlon, and her husband John, of Dorchester. He was the adoring grandfather of Charlie, Sarah, Allison, and David Mackey, and Sydney, Jackie, Mallory, and Maggie Hanlon.

Bob is also survived by two of his sisters: Sister Margaret Sheffield, O.P., of Sinsinawa, Wisconsin, and Cathy Durham of Plymouth. He was preceded in death by his sister Margaret (Peggy) Connors of Duxbury and brother Raymond Sheffield of Brockton. He is also survived by his wonderful brothers- and sisters-in-law, many beloved nieces, nephews, and members of his extended family.

Anyone who ever had the pleasure of meeting Bob Sheffield knows how special he was. He was kind, smart, competent, and hugely optimistic. His warm and earnest manner made him loved and trusted by all. He never complained, and his sunny disposition never left him, even after his challenging injury last spring.

Bob was extremely devoted to his late wife, Mary. They loved to socialize and had many treasured friends. They shared a love of Florida, traveling, playing golf, and spending time with their children and grandchildren. Bob truly enjoyed his monthly breakfasts with his breakfast group.

A lifelong resident of Milton, Bob attended kindergarten at Tucker School and graduated from Milton High School in 1959. He earned his bachelors in business from Boston College and spent six years in the Army Reserves. He got his MBA from Northeastern and was appointed the CFO of Mass Home Mortgage Finance Agency, later Mass Housing. He earned his law degree from Suffolk Law School, then went on to pass the Massachusetts and Florida bar exams in the same week. He opened his law practice in East Milton Square in 1989. Bob loved being an attorney, and was Milton’s go-to lawyer for 30 years. He enjoyed helping people and only accepted cases he thought were in the best interest of the town and the community.

Throughout his life, Bob felt a deep civic responsibility and played an active role in Milton. An elected Town Meeting member since 1971, he never missed a Town Meeting in 50 years. Over the years he was a member of the Knights of Columbus, a member of the Warrant Committee, a member and past president of the Milton Jaycees, and a member and past president of the Kiwanis Club. He loved organizing the traditional Milton 4th of July races and handed out ice cream to the kids for 35 years in a row.

He served on the Board of Directors of Milton Hospital for 20 years, and was on the Finance and Investment Committee. He also served on the Boards of Fuller Village, Curry College, and the Quincy Neighborhood Club. He supported his wife in her years on the Board of HOME Inc (Pine Tree Brook Homes), and later joined the Board himself. He loved history and was a member of the Milton Historical Society. He also coached Milton youth basketball for many years.

Bob was a man of deep faith and was very involved with St. Mary of the Hills Church. He was active in the parish since childhood, and served his parish community from a young age as an altar boy until last year as a lector.

Bob and Mary were members of the Milton Hoosic Club, the Quincy Neighborhood Club, and Del Tura Country Club in Fort Myers, FL. They lived in a wonderful community at Pine Tree Brook for the past 10 years. His neighbors were extremely supportive as Bob was recovering from his injury and returned home.

Most of all, Bob was a family man. He always enjoyed spending time with his children and grandchildren, and was supportive, loving, and funny. He will be greatly missed.

For those who feel comfortable attending, visiting hours at the Alfred D. Thomas Funeral Home 326 Granite Ave., Milton, Wednesday 5-7 p.m.  Due to the current Covid-19 restrictions, only 20 guests will be allowed within the funeral home at once, masks are required, and guests should bring their own pens to sign the register book.  Funeral Mass will be held at St. Mary of the Hills Church, Milton, Thursday morning at 10:00 a.m. A private burial will be held in Milton Cemetery. The Funeral Mass will be live-streamed and can be accessed through Facebook under Blue Hill Streaming Service page.

In lieu of flowers, donations may be made in Bob’s memory to the Milton Council on Aging, 10 Walnut St., Milton, MA 02186.  A celebration of Bob’s life will be held at a later date to be announced.


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