Bill Diamond

WINDHAM – On Aug. 31, 2025, as the sun was setting, Bill Diamond, devoted husband, father and Papa, passed away peacefully at his home in Windham, with his family by his side.

After his cancer diagnosis in June of 2024, this is a quote from a diary he kept. “My first thought was that I’ve had a great life of 80 years. A kid from a small dirt farm in West Gardiner, Maine, poor as poor gets. My father left just after I was born, so we lived with my grandfather on the small farm. Who would have guessed I’d have so many opportunities to reach some of the top elective offices in state government.”

Bill graduated from Gardiner High School in 1963 and went on to receive his B.S. in Education and master’s in Administration from Gorham State Teachers College. Bill was a teacher, principal and superintendent in the Windham schools for 20 years.

In 1972, Bill was awarded a Ford Foundation full year paid scholarship to study Politics and Education throughout the U.S. and Europe. This began his journey into the political world, winning a seat in the State Legislature in 1976. Bill was then elected to two more terms in the Maine House, and five terms in the Maine Senate. Also elected to four terms as Maine’s Secretary of State from 1989-1997.

Bill co-founded six small businesses with his current business partner and good buddy, Ray Roux. He was also Windham’s Chamber of Commerce business person of the year.

Bill’s involvement in his town and state were endless. He was an EMT on Windham’s Rescue Unit from 1978-1982, 34-year sponsor of Windham’s Little League Softball Team, co-founder of Windham Land Trust, Neighbors Helping Neighbors, Hospice of Southern Maine and on the board of MSSPA. He was especially proud of being the founder of “Walk a Mile in Their Shoes” in 2023.

Bill is survived by Jane (Estes), his wife and partner of 57 years; daughters Dr. Karyn Diamond and Kristin Dumont (J.P.); proud “Papa” to Holly, Scarlett, Ella, Luke, Ava, Laila, Jesse, and Mya; sisters Darlene McCormick (Earle) and Elizabeth Dore; and special godson, Paul Petersen.

Bill was predeceased by his parents Elsie Emery and George Diamond.

He will be missed by all who knew him, and would say to you all “Happy Trails to you, until we meet again.”

A funeral service will be held Saturday, Sept. 27 at 1 p.m. in the auditorium at Windham High School.

In lieu of flowers, please donate to a scholarship fund in Bill’s name to

Windham High School

406 Gray Rd.

Windham, ME 04062