Robert John Bennett

Naples - Robert John Bennett, 84, of Naples, FL died peacefully on November 4, 2025 surrounded by his loving family. Robert, more affectionately known as Bob or "Bear," was born in Fitchburg, MA on June 7th, 1941 to Mabel R. Bourque (formerly Bennett) and Raymond Bennett. Bear was one of 4 (Richard Bennett, Patricia Tocci, Judith Porter), and his half brother, Roy (Skip) Bourque, completed his family with his step-father, Roy J. Bourque.

Bob went to the Holy Family School while at the Brightside Orphanage in Springfield, Massachusetts for his elementary years alongside his brother Dick. He reunited with his mother, siblings, and step- father, Roy Bourque in his early junior high years. The reverence he had for his stepfather for taking in, loving and sacrificing for 4 children that weren't biologically his own informed the person Bear would become. He put his discipline and hard work into school and sports at Fitchburg High School. He earned 7 varsity letters in track and field, football and basketball, and had leading roles in the school play his junior and senior years. During this time he also held various jobs to help support the family. Bear won a math award his Senior Year which, combined with Basketball, led to a scholarship at Babson College.

Bob would go on to graduate from Babson College with a BS, University of Massachusetts Graduate School at Amherst with an MBA, and Harvard Business School's Advanced Management Program.

Following early employment in computer sales at Burroughs Corporation, finance and industrial engineering at Norton Co., and management consulting at Touch Ross & Co. Bob's career progressed through more than 35 years in commercial banking which included 12 years with Boatmen's Bankshares, St. Louis (Now Bank of America) where he left as Executive VP to become Chairman & CEO of OnBank & Trust, Syracuse for 11 years which merged in 1998 with M&T Bank Corp., Buffalo where he became Chairman of the Board at the inception of the merger. He retired from active operational management at M&T in 2001. Bob then spent an additional 10 years on the board and its standing committees until his retirement at age 70 in 2011.



Bob was an active member and a director of numerous business, civic and community organizations including: Chairman of Crouse Hospital in Syracuse; President of the Greater Syracuse Chamber of Commerce; Chairman of Syracuse Boys and Girls Clubs; Syracuse Symphony; Chairman of Syracuse Stage; Junior Achievement; Illinois College; LeMoyne College; and Syracuse University Business School. He also served on the boards of the Federal Home Loan Bank of NY, The New York Bankers Association, NASDAQ Advisory Board, Welch Allyn Co., Fay's Drugs, The Pietrafesa Corp., SBLI Life Insurance Co. of NY, and Farmers & Trader's Life Insurance Co. He received community service awards from Crouse Healthcare Foundation, The Boys and Girls Clubs, The March of Dimes, and the Interreligious Council.

He is survived by his loving wife of 54 years, Kathy (Dessert), four children: Burke Bennett and wife Helen of Vero Beach, FL, Kristin Gray of Pennington, NJ, Kim Barad and husband Nate of Bedford, NH, and Richard Bennett of Boynton Beach, FL. He leaves nine beloved grandchildren whom he adored: Burke Jr., Robert, Belle, Madelyn, Bennett, Katy, AJ, Sam and Ian, and dog Max. He is also survived by his sisters, Patti Tocci and husband Amedio (deceased) of Leominster, Massachusetts, Judy Porter of Fitchburg, Massachusetts, and brother Roy (Skip) Bourque and wife Kathy of Westminster, Massachusetts and several adored nieces and nephews. He is predeceased only four months prior by his cherished brother, Richard (Dick) Bennett and wife Claire of Plymouth, Massachusetts.

Bear was a man of quiet strength, integrity and good humor. He was wise, loyal, and family always came first. His timeless wisdom and unconditional love shaped the best parts of his family. His presence - poised and quietly commanding - filled the room, yet the moment he cracked a mischievous joke, his eyes would sparkle and his smile and laugh would light up everything around him. Those lucky enough to call him family or a friend felt instantly special when around him. Bear's fondest family memories were of times spent at their summer home in the Thousand Islands on the St. Lawrence River, and trips to Steamboat, Colorado.

In lieu of flowers please send contributions to American Cancer Society, American Heart Association or Wounded Warriors Project.

Memorial service to be held in Naples, FL in January 2026.