Robert “Bob B” Elbridge Benson passed away peacefully in his sleep on April 20, 2026.
Bob was born on December 26, 1962, in Augusta, Maine. He was the third child of Carol Ann Libby Benson and Frank Elbridge Benson Jr., of Gorham, Maine, formerly of East Winthrop.
Bob grew up in East Winthrop and graduated from Winthrop High School in 1981, where he was active in the Debate and Theatre Club. He became an Eagle Scout and, for many years, volunteered as a Boy Scout leader, including canoeing the 50-mile stretch of the Penobscot River in northern Maine.
He attended Augustana College in Sioux Falls, South Dakota. He was active in debate and theatre, graduating in 1985. He remained close with his classmates throughout his life, cherishing ongoing friendships and annual “family” trips with them and their families. He went on to earn his law degree from New England School of Law and became an attorney, representing Boston nurses and standing alongside them on picket lines until a fair agreement was reached. He later worked for many years as a hotel manager and went on to become a real estate broker.
In Boston, Bob built a vibrant and engaged community life. He bowled with the MNBL and became deeply involved in the Boston Gay Basketball League (BGBL), joining in the 1995–1996 season and playing a key role in its early development. Over the years, he served as a player, coach, Assistant Commissioner, Treasurer, and league sponsor. He supported the league through fundraising, recruiting new players, and helping establish the Women’s Division. In 2019 Bob was inducted into the BGBL Hall of Fame.
Bob also served as an assistant volleyball coach at Newbury College alongside his dear friend, the late Coach David Hildebrandt. To his players, he was always “Coach Bob”—a title they continued to use long after their college years, a testament to his lasting impact both on and off the court.
He was an active member of the Cambridge Boston Volleyball Association (CBVA), the North American Gay Volleyball Association (NAGVA), and Yankee Volleyball. A certified referee through USA Volleyball, Bob was a longtime head of referees for the Boston Beantown Classic, an annual NAGVA-sanctioned tournament. He was instrumental in ensuring the tournament ran smoothly, recruiting skilled referees and fostering a safe, welcoming environment for all.
Bob lived unapologetically as his authentic self. He had a remarkable ability to speak honestly while softening the edges with humor. His gifts were many—his intelligence, wit, insight, compassion, athleticism, and his unforgettable drag performances. Whether on the volleyball court, where he was known for his exceptional setting hands, or in his signature rainbow skirt, Bob brought joy and belonging wherever he went. He had a unique way of making everyone feel welcome and included, especially within the CBVA community.
He was known for his quick wit, playful sass, and sharp humor—often offering a perfectly timed, clever, and sometimes delightfully irreverent remark that brought laughter to those around him. The joy he created and the lives he touched will not be forgotten.
Bob is survived by his father, Frank Benson Jr.; his siblings, Wendy Benson Sargent of Gorham, Maine; Randall Benson and his wife Tammy of Sturbridge, Massachusetts; and Christopher Benson of Madison, Alabama. He was predeceased by his mother, Carol Ann Libby Benson.
He is also survived by his nieces and nephews: Justin Benson and his husband Charles Berds of Dorchester, Massachusetts; Alexandria Gonzales and her husband Joe of Swarthmore, Pennsylvania; Michael, Natalia, and Kenny Benson of Martinsville, New Jersey; and Bryce and Susan Benson of Madison, Alabama. He was a proud great-uncle to Asher Cole Gonzales. He is also survived by many cousins and a wide circle of friends who became family.
A memorial service will be held at the Brady & Fallon Funeral Home, 10 Tower Street, (Opp. Forest Hills MBTA Station) Jamaica Plain on Saturday May 9 from 1-4 pm. Visiting hours will begin at 1:00 p.m., followed by a service at 2:00 p.m. and fellowship afterward.