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Alan ‘Al’ Dole

December 5, 2018 03:00 pm

Alan “Al” Dole, longtime Chatham resident, peacefully departed this life on Sunday, November 11, 2018 in Waterbury, CT after a lengthy illness. His family was by his side. Born on April 13, 1943 in Springfield, MA, Al was one of three children: J. Robert Dole (deceased) and Janice Dunn. Son of the late Helen Louise (Abbott) and John Markham Dole. Al spent his adult life in Chatham, NY. He was married for forty-nine years to his college sweetheart, Jane who died in 2015.

Educated in the East Longmeadow, MA school system, Al graduated from East Longmeadow High School. He attended the University of Massachusetts at Amherst, Stockbridge School and completed his college studies at Westfield State University. After college, he enjoyed a long career in agriculture and sales.

Alan was active in the Chatham community. He supported school and athletic activities particularly when his daughter, Kim, was a participant. Family was everything to Al and he was devoted to Kim; his son-in-law, Thomas Allen, and his grandsons Jaiden Gray, Kai Robert and granddaughter, Maila Jane. An avid fisherman, Al and his beloved Jane spent winters in Florida where he and his friends enjoyed the perennial sunshine.

Al was also a dedicated football enthusiast. He was involved with the Empire Football League (EFL) operations for almost 40 years as a player, coach, owner and Deputy Commissioner. He was a respected leader and mentor who was held in high regard by everyone he met. There are numerous stories that describe Al as a wise, compassionate coach who saw unrealized potential in athletes and challenged them with opportunities to play when other doors were closed. Al’s contributions to semipro/minor league football led to his selection to the prestigious American Football Association’s Hall of Fame in 2006.

In addition to his immediate family, daughter Kimberly (Thomas) Allen of Watertown, CT and grandchildren Jaiden, Kai and Maila, Al leaves myriad family and friends to cherish his life and memory including: his sister, Janice Dunn; nephews Sean Dunn (Jung Kwak); Harley Dole (Debbie); nieces Julie Smith (Marshall); Heather Hampton (Charlie); Sherry Dole and many great-nephews and nieces.

A memorial service is planned for Spring 2019. For condolences you may email his daughter Kim at