The late Bill Diamond continues to influence future generations in Windham and a new initiative started by a high school student hopes to keep his memory alive.
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| Windham High School softball player Oakley McLeod once played for the Bill Diamond team in Windham Little League years ago and has created a new team in the league for this season to honor the memory of the late Windham legislator, educator and businessman. SUBMITTED PHOTO |
Diamond, who served more than 40 years in politics and service to the state, died at the age of 80 in August 2025 following a hard-fought battle with cancer. He served as a state legislator representing Windham, Maine’s Secretary of State from 1989 to 1997 and was also an educator and businessman who sponsored many local youth sports teams.
“I have been playing softball for 11 years and I love how softball shaped me into the person I am today,” McLeod said. “I am more confident and comfortable with myself, and I like how it involves mental and physical strength. What I remember about being on Bill Diamond’s team are the friendships I made and it was a start to my softball career. I remember learning the game through many great coaches and looking up to the older girls. I know how much it meant to Bill seeing girls play the sport they love.”
To honor the role Bill Diamond played in her life and continue a tradition that he started, McLeod stepped up this spring and created a new Windham Little League softball team carrying the Bill Diamond name.
“I wanted to name it after Bill Diamond because I played on the Bill Diamond team when I was younger and it brings back memories and holds a tradition to the Windham community,” McLeod said. “I want young girls to know how much he has done in the community.”
She also has been backed by her family in creating the new youth softball team.
“My family has been supportive through naming the team in Bill Diamond’s name,” she said. “They all thought it was a great way to represent the community, and it showed growth in myself as well as the Windham community having my back. We all miss Bill and want to keep the impact he had upon Windham.”
She said her high school teammates also have supported her efforts to create the new team and name it for Diamond.
“They think it’s a great way to honor our history as well as Bill’s and they want young girls to get the same impact that we did,” McLeod said. “Playing Little League softball was a key impact in our life and we made great bonds and played the sport we loved.”
McLeod says that in getting to know Bill by playing on a youth softball team he sponsored, it was evident how much he cared about children.
“Bill was great and he always supported children though his work in the legislature and as a teacher and principal, so he knew kids,” McLeod said. “I think more people should know his background because he was always there for Little League and he made a great impact upon Windham. They should know his love for softball and educating kids.”
According to McLeod, creating this team with Diamond’s name is a small way of paying respect to the person he was.
“Personally, I would love to represent Bill Diamond as much as I can. I wanted to show my love for softball and the love I had for Little League by representing Bill Diamond and his impact on Little League players,” she said. “I wanted to keep the memories going and bring back a great time in my life.”
Even though Diamond is no longer with us, McLeod says he would love the thought of naming a new team in his honor.
“I know Bill loved softball so seeing his name again would mean something to him because we all grew up with the Bill Diamond team and we all loved it,” McLeod said, “Bill came to support our games, so Bill would think this is a good thing.” <
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