Charles Alonzo Winchester, 94, died peacefully in his sleep early Sunday, May 29, 2022 at his home in Lexington, Massachusetts. He leaves his wife, Jean; daughters Carol Ann (Cherrington), Maryann (Trono), Suzanne (Miller), Joanne (Brine) and Dianne Winchester; nine grandchildren; and eight great-grandchildren.
Charles grew up in Dorchester, the son of Senator Charles A. Winchester and Lillian Ursula Desmond. He was one of six children, including living siblings George Winchester, S.J., and Paula Trask. He graduated from St. John's Preparatory and received his bachelor's degree from the College of the Holy Cross and master's degree in Criminal Law from Boston University. Throughout his education he was a notable athlete, in the Hall of Fame at St. John's and playing football, basketball, baseball, and track at Holy Cross. He served in the Navy Air Force Training Program in 1946 and in the Army during the Korean War.
That spirit of service was the hallmark of Charles' life. After several years working as an insurance broker, he was invited to become a probation officer for the Woburn District Court, eventually being named chief probation officer of the Eastern Middlesex Division of the 4th District Court in Woburn. He received a Lifetime Achievement Award from the Middlesex Bar Association and holds the distinction of being the longest-serving probation officer in Massachusetts, finally retiring after 42 years of service. A plaque imbedded in stone outside the courthouse in Woburn marks that achievement.
He was a sensitive man with a deep compassion for people in difficult circumstances, and he helped many, many people rebuild their lives and avoid prison. In a job that could all too easily be bureaucratic, he made it entirely human and personal. He was truly invested in each person's life and welfare. He also was very outgoing, with a thousand jokes, making friends easily among coworkers, clients, judges, police officers, politicians and celebrities.
In addition to being the chief probation officer, Charles found time to work as a justice of the peace, whose first wedding service was for Olympic skater Nancy Kerrigan. He was also the chairman of the Woburn Board of Assessors and a lecturer in Criminal Justice at Northeastern University, and was certified in underwater search and rescue. He loved music and had a fine singing voice, a legacy from his father, who was a well-known orchestra leader in Boston in the 1920s.
But the center of his life was his family. He and his wife, Jean, met while they were in college, and each of them knew after the first date that they would be married. Charles was devoted to Jean, and celebrated their 70th wedding anniversary a week before he died. On the evening of his death, he sat holding Jean's hand for a long time before kissing her goodnight for the last time.
All services will be private. A mass and celebration of Charlie's life will be held in the future. In lieu of any gestures please consider a donation to St. John's Prep in Danvers in Charlie's honor, either online (https://www.stjohnsprep.org/giving/annual-giving) or by mail at 72 Spring St., Danvers, MA 01923.

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A Graveside Service for Charles Winchester is presented on our YouTube based Funeral Services page using the following address.

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https://www.youtube.com/watch?v=8mzxUN66u24