William “Bill” P. Whiffen, Jr., 66, of Naples, FL, passed away on March 20, 2025. Born in Pittsfield, MA, on May 10, 1958, to Wm. “Pete” & Myra Whiffen, he grew up in Great Barrington, excelling in sports and building lifelong friendships. He moved to Florida in 1999, retiring in 2023. Bill will be remembered for his wit, humor, and love of storytelling. He cherished fishing, hunting, and family traditions. He is survived by his children, Andrew & Jessica, their spouses and 5 grandchildren, sister Deborah, and former wife, Stephanie. He was predeceased by his parents and granddaughter Rose.