In loving memory of our beloved husband, father, grandfather, and great-grandfather

Ronald A. Bennett
December 14, 1949 – October 5, 2025

Ronald A. Bennett, 75, of Clearwater, Florida, formerly of Jamaica Plain, Massachusetts, passed away peacefully on October 5, 2025, surrounded by his loving family.

Born on December 14, 1949, Ron grew up in Jamaica Plain, where he built a life centered on family, friendship, and community. In 2017, he and his beloved wife, Rita, made their home in Clearwater to enjoy retirement and the Florida sunshine.

Ron and Rita were married on November 13, 1967, and shared 57 wonderful years together filled with love, laughter, and adventure.

He leaves behind his loving wife, Rita Bennett; daughter Lisa Watson (husband Chris) of Cape Coral, FL; son Ronald A. Bennett Jr. (wife Tracey) of Chelmsford, MA; and daughter Heatherlee Madden (husband Gary) of Largo, FL. He was the proud grandfather of Adriana, Kelsey, Ryan, Krystle, CJ, Jake, Brendan, Brianna, and Corey, and the adored great-grandfather of eleven.

Ron is also survived by his siblings Harold Bennett of Cambridge, MA; Ella Lorraine Brown (and her late husband Ronald) of North Carolina; and Anna Zevolo (husband Patrick) of Parrish, FL. He was predeceased by his mother Esther Bennett and his brothers John Del Dotto and Bert Del Dotto.

Family meant everything to Ron. His children fondly remember their Sunday family days spent roller skating, going to the movies, bowling, and visiting Lincoln Park. Every year, Ron would load the family into the car and drive straight through from Massachusetts to Florida for their annual Disney trip—only stopping for quick pee breaks. Those were the memories he treasured most.

Ron was also known for his dedication to his community. When no one else stepped forward, he took it upon himself to run the Jamaica Plain Little League, ensuring that local kids, including his own, could experience the joy of the game.

In his younger days, Ron enjoyed trips to the casino and later found joy in traveling and cruising with Rita—often, of course, spending time in the ship’s casino. At home, he loved relaxing with his ragdoll cat, Misha and playing poker on the TV. We always got a laugh out of him saying “Five bucks!” when you asked him for anything. It was a running joke that brings a smile to those who loved him.

Ron will be remembered for his deep love for his family and his unwavering devotion to the people he loved most. His legacy lives on in the laughter, memories, and love he leaves behind.

 

A private family celebration of life will be held at Best Care Cremation, 15381 Roosevelt Blvd, Clearwater, FL 33760, on October 24th, 2025. Visitation will be held from 3:00PM-4:00PM, with a small service following from 4:00pm-5:00PM.