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James A. Johnson III, Longtime Winchester Resident, Passes Away at 71
It is with deep regret that we share the passing of James A. Johnson III, a lifelong resident of Winchester, Massachusetts, who passed away on Wednesday, April 16, 2025 at the age of 71. He was the beloved husband of 49 years to Barbara A. (Scholl) Johnson and a devoted father, grandfather and community leader.
Born to the late James A. Johnson Jr. and Dorothy (O’Keefe) Johnson, James—affectionately known as “Jimmy” to many, grew up in Winchester and graduated with the Winchester High School Class of 1972. He was preceded in death by his two brothers, Richard and David Johnson. Jimmy’s presence was impossible to ignore and even harder to resist. His childhood was filled with adventures alongside his brothers, full of laughter and the lifelong friendships they built together in their hometown.
For over 50 years, Jimmy proudly owned and operated Johnson Fuel Oil—a business built on hard work, integrity, and a deep commitment to the community. Throughout his career in the fuel oil, trucking, and car sales industries, he formed countless friendships and lasting connections. His tireless work ethic and unwavering dedication were well known to everyone he worked with.
And those who knew him also knew that Jimmy loved a good deal. Whether it was snagging a car at auction or bargaining over a $2 wrench at a flea market, he never passed up the chance to haggle. If there was a bargain to be had, you could count on Jimmy to be right there, working his charm and trying to knock a few dollars off the price.
Jimmy’s devotion to the Winchester community was steadfast. He served with distinction on the Board of Selectmen for 18 years and gave his time and leadership to numerous town committees, including the Finance Committee, Town Day Committee, and Capital Planning Committee. In 2016, he was honored as Winchester's Citizen of the Year. His passion for public service and his efforts to make Winchester a better place have left a meaningful and lasting legacy.
Above all else, Jimmy was defined by his deep love for his family. He was the kind of husband, father, and grandfather who would do anything for those closest to him. His happiest moments were spent surrounded by family, especially during summers at Herring Pond in Plymouth, filled with boating, tubing, and treasured memories with his grandchildren. In the winters, he found joy at his home in Lincoln, NH, skiing and snowmobiling with the ones he loved most.
Jimmy leaves behind his loving family: his wife Barbara, son James A. Johnson IV and his wife Jennifer of Walpole, MA, along with their three children—Victoria, Savannah, and James V; son Robert Johnson and his wife Melissa of Medford, MA, and their son Ronan; and daughter Jennifer Penquite and her husband Bryan of Enfield, CT, and their son William.
Though we are heartbroken by his passing, we will carry his love, his laughter, and his legacy with us always. Jimmy wouldn’t want us to dwell in sadness. He’d want us to come together, tell stories, and celebrate the incredible man he was and the life he lived so fully.
Relatives and friends are kindly invited to gather for Visiting Hours at Costello Funeral Home, 177 Washington St., Winchester, on Tuesday, April 22 from 4-7PM, and again on Wednesday, April 23 at 10AM, followed by a Funeral Mass in St. Mary’s Church, 155 Washington St., Winchester, at 11AM. Burial will follow in Wildwood Cemetery, Winchester.
