When the RSU 14 Board of Directors meets on Wednesday, Nov. 4 at Windham High School, further discussion and the name of the new middle school currently under construction will be voted upon.
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| As construction continues for the new middle school at 71 Windham Center Road, RSU 14 Board of Directors members will determine what to name the school on Nov. 4, including a proposal to name the building after the late Windham and Raymond educator and legislator Bill Diamond. PHOTO BY ED PIERCE |
Diamond, a longtime legislator, educator, local business owner and child welfare advocate, died Aug. 31, 2025, at the age of 80. He also co-founded Windham Neighbors Helping Neighbors to provide heat assistance to those in need in Windham and Raymond, and the Walk A Mile In Their Shoes Foundation to end child homicide in the state of Maine.
While some RSU 14 board members expressed support for naming the school after Diamond, others disagreed, saying they wanted the school’s name to reflect both the communities of Windham and Raymond and recognizing each town.
During public comments, speakers including State Rep. Mark Cooper and Maine State Senate District 26 Republican candidate Kenny Cianchette supported naming the school after Diamond because of his advocacy for children in the state.
One board member then inaccurately said that Diamond had no connection with Raymond schools, and she wasn’t in favor of naming the new middle school after him.
However, Raymond Schools’ first school superintendent, Frank McDermott, who lives in Raymond, confirmed that when he left the Raymond district to join Bonny Eagle Schools in 1976, Bill Diamond succeeded him as superintendent and as the principal of Jordan-Small School.
Diamond grew up on his grandfather’s farm in West Gardiner and originally came to the Lakes Region after earning a bachelor’s degree and master’s degree in education at Gorham State Teacher’s College. Starting in 1968, he taught in Windham schools and went on to serve as the first principal of Windham’s Manchester School, and he also led Field-Allen Junior High School and Windham Middle School as principal before joining Raymond Schools as superintendent and the principal of Jordan-Small School.
He first ran for the Maine House of Representatives in 1976 as a write-in candidate in Windham, winning re-election in 1978 and 1980. In 1982, he won a seat in the Maine State Senate seat, representing Windham and Raymond and won re-election to the Maine Senate in 1984.
In 1989, Diamond was sworn in as Maine’s 45th Secretary of State and campaigned to become governor in 1986 and then campaigned for the 1st Congressional District position in the U.S. House of Representatives in 1994.
He founded the Windham Independent newspaper and publicized achievements of both Windham and Raymond students for more than a decade before deciding in 2004 to re-enter politics and winning the Maine Senate District 12 seat representing Windham and Raymond. He won re-election in 2006, 2008 and 2010 before being term limited. Four years later in 2014, Diamond won the Maine Senate District 26 seat, representing Windham and Raymond, and subsequently won re-election to that position in 2016, 2018, and 2020.
Before leaving political office in 2022, Diamond was known statewide as a staunch advocate for children and led Maine Senate investigations into prominent deaths of abused children whose families were relegated to the state’s child welfare system. In 2014, Diamond wrote a book about the subject called “The Evil and the Innocent.”
In 2023, Diamond launched the “Walk A Mile In Their Shoes Foundation,” a non-profit dedicated to preventing child homicides and the abuse of children who are under the supervision or direct care of the State of Maine or who are or have been associated with the state’s Child Protective System.
During the RSU 14 meeting on Oct. 21, a board member suggested that it would be unusual for the school district to name a school after an individual, yet the school district’s Manchester School, Field-Allen School and even Jordan-Small Middle School where the board meeting was held were all named after individuals. Another board member said she admired Bill Diamond's accomplishments, but she supported naming the new middle school Windham Raymond Middle School to make the Raymond students and the Raymond community feel that they are an equal part of the school.
Karyn Diamond, Bill Diamond’s daughter, attended the Oct. 21 meeting and prior to that had posted on Facebook that the Diamond family was humbled by the idea of possibly naming the new school after him.
“Naming the school after my dad, a man who dedicated his life to educating and protecting children and who poured out his heart into his hometown of Windham, would be the highest honor this community could do for him,” she said.
John Cressey of Windham believes the school should be named after Diamond.
“Having the new school named for one of the most influential people in Windham and Raymond, who rose up to become Maine Secretary of State, all while still maintaining close ties to the community would be inspirational,” Cressey said. “He deeply cared about the community and for children and was at every sporting event until he passed away. He sponsored a softball team every season for 30 years in Windham Little League even after his daughters were out of school.”
RSU 14 Board Chair Christina Small said the Oct. 21 board discussion was preliminary, and she personally does not believe that not having "Raymond" in the name of the new school would marginalize Raymond students.
She said there is not a high school in Raymond so Raymond students attending Windham High School have the option to attend other high schools, such as Gray New Gloucester High School and that is why it isn’t named "Windham Raymond High School."
Small said that middle school students in Raymond will have to attend the new school and that is why a name to reflect both communities is under consideration by the board.
Public comments about the school’s name will be included during the RSU 14 Board of Directors meeting at 6:30 p.m. Wednesday, Nov. 4 at the Windham High School Performing Arts Center. <
While some RSU 14 board members expressed support for naming the school after Diamond, others disagreed, saying they wanted the school’s name to reflect both the communities of Windham and Raymond and recognizing each town.
During public comments, speakers including State Rep. Mark Cooper and Maine State Senate District 26 Republican candidate Kenny Cianchette supported naming the school after Diamond because of his advocacy for children in the state.
One board member then inaccurately said that Diamond had no connection with Raymond schools, and she wasn’t in favor of naming the new middle school after him.
Diamond grew up on his grandfather’s farm in West Gardiner and originally came to the Lakes Region after earning a bachelor’s degree and master’s degree in education at Gorham State Teacher’s College. Starting in 1968, he taught in Windham schools and went on to serve as the first principal of Windham’s Manchester School, and he also led Field-Allen Junior High School and Windham Middle School as principal before joining Raymond Schools as superintendent and the principal of Jordan-Small School.
He first ran for the Maine House of Representatives in 1976 as a write-in candidate in Windham, winning re-election in 1978 and 1980. In 1982, he won a seat in the Maine State Senate seat, representing Windham and Raymond and won re-election to the Maine Senate in 1984.
In 1989, Diamond was sworn in as Maine’s 45th Secretary of State and campaigned to become governor in 1986 and then campaigned for the 1st Congressional District position in the U.S. House of Representatives in 1994.
He founded the Windham Independent newspaper and publicized achievements of both Windham and Raymond students for more than a decade before deciding in 2004 to re-enter politics and winning the Maine Senate District 12 seat representing Windham and Raymond. He won re-election in 2006, 2008 and 2010 before being term limited. Four years later in 2014, Diamond won the Maine Senate District 26 seat, representing Windham and Raymond, and subsequently won re-election to that position in 2016, 2018, and 2020.
Before leaving political office in 2022, Diamond was known statewide as a staunch advocate for children and led Maine Senate investigations into prominent deaths of abused children whose families were relegated to the state’s child welfare system. In 2014, Diamond wrote a book about the subject called “The Evil and the Innocent.”
In 2023, Diamond launched the “Walk A Mile In Their Shoes Foundation,” a non-profit dedicated to preventing child homicides and the abuse of children who are under the supervision or direct care of the State of Maine or who are or have been associated with the state’s Child Protective System.
During the RSU 14 meeting on Oct. 21, a board member suggested that it would be unusual for the school district to name a school after an individual, yet the school district’s Manchester School, Field-Allen School and even Jordan-Small Middle School where the board meeting was held were all named after individuals. Another board member said she admired Bill Diamond's accomplishments, but she supported naming the new middle school Windham Raymond Middle School to make the Raymond students and the Raymond community feel that they are an equal part of the school.
Karyn Diamond, Bill Diamond’s daughter, attended the Oct. 21 meeting and prior to that had posted on Facebook that the Diamond family was humbled by the idea of possibly naming the new school after him.
“Naming the school after my dad, a man who dedicated his life to educating and protecting children and who poured out his heart into his hometown of Windham, would be the highest honor this community could do for him,” she said.
John Cressey of Windham believes the school should be named after Diamond.
RSU 14 Board Chair Christina Small said the Oct. 21 board discussion was preliminary, and she personally does not believe that not having "Raymond" in the name of the new school would marginalize Raymond students.
She said there is not a high school in Raymond so Raymond students attending Windham High School have the option to attend other high schools, such as Gray New Gloucester High School and that is why it isn’t named "Windham Raymond High School."
Small said that middle school students in Raymond will have to attend the new school and that is why a name to reflect both communities is under consideration by the board.
Public comments about the school’s name will be included during the RSU 14 Board of Directors meeting at 6:30 p.m. Wednesday, Nov. 4 at the Windham High School Performing Arts Center. <
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