Retired Wiscasset Middle High School math teacher and coach Timothy “Tim” Flanagan at his home in 2017. Surrounded by family, Flanagan died at his home on Dec. 6. (LCN file)
Wiscasset’s Timothy “Tim” Flanagan is being remembered by those who knew him as a compassionate and considerate educator, coach, friend, and community member.
“They don’t make them like Tim Flanagan,” said Midcoast Sports Hall of Fame Board of Directors President Tom Mellor. “A person like him comes along once in a lifetime.”
Flanagan, who died at his home in Wiscasset on Dec. 6, was best known for his roughly four-decade coaching and teaching career at Wiscasset High School, now Wiscasset Middle High School.
Beginning his teaching career as a mathematics teacher at Westbrook High School in 1971, Flanagan joined Wiscasset High School in 1977 and remained until his retirement in 2017.
He led the 1990-1991 Wiscasset boys basketball team to the Class C state championship, the only state championship in the high school’s boys basketball history. The team, which included Flanagan’s sons Darin and Donald, was honored as an outstanding team at the 2023 Midcoast Sports Hall of Fame banquet.
Robert “Bob” Sommers, a former basketball and soccer coach and teacher at Wiscasset High School, and Mellor both met Flanagan in the 1970s.
Sommers said he and Flanagan bonded over their shared love of golf. They worked together until Sommers’ retirement in 2011 and remained friends until Flanagan’s death.
When Flanagan started at Wiscasset High School in 1977, Sommers said he “blended right in.”
When he was not busy as “Coach Flanagan,” he was crafting young minds in the classroom through mathematics.
Flanagan’s contributions to the community did not stop at the doors of Wiscasset High School. He was a dedicated member of the Midcoast Sports Hall of Fame Board of Directors for over a decade, advocating for the inclusion of athletes from Wiscasset High School and Boothbay Regional High School, said Mellor. At the time of its inception in 2003, Mellor said the hall only included athletes from Knox County schools.
A native Mainer, Flanagan was born in 1946 in Rockland, graduating from Rockland High School in 1964.
His love for sports started early in life. As a child, he would walk from his home in Rockland to the Megunticook Golf Club in Rockport, where his father worked as the head golf professional, according to his obituary. Flanagan’s father taught him the game, and he eventually worked his way up from caddying to becoming the caddy master at the Portland Country Club.
Flanagan’s golf accomplishments span decades. He won numerous titles, including the Maine Junior Championship in 1964, the Maine State Father/Son Championship in 2007, and multiple club championships at Rockland Golf Club; Wawenock Golf Club, of Walpole; and Sheepscot Links Golf Club, of Whitefield.
Coach Timothy “Tim” Flanagan led the 1990-1991 Wiscasset boys basketball team to Wiscassets first boys basketball state championship win in 1991. (LCN file)
Fresh out of high school, Flanagan was drafted into the U.S. Army in 1965, where he was selected to attend the United States Military Academy Preparatory School at West Point in New York.
Following his service, Flanagan attended Gorham State Teachers College, now the University of Southern Maine. There, he met his wife, Judy, whom he married in 1969. The couple had three children: Darin, Donald, and Doreen.
While at Wiscasset High School, Flanagan coached basketball, golf, cross country, track, baseball, tennis, and the math team. Along with the 1991 boys basketball state championship win, Flanagan’s track record included multiple state math team championships, a state golf Championship, and numerous conference and regional championships.
Sommers recalled Flanagan’s dedication to his students, noting that Flanagan often paid “out of his own pocket” to purchase items for the school. Sommers said Flanagan’s approach to coaching and teaching was serious yet compassionate.
“Tim (Flanagan) was very proud of the school and the teams that he coached,” Sommers said. “He’s one of the few guys that I know that was real successful by coaching either boys or girls.”
In the halls of Wiscasset High School in the 1990s, Sommers said “if you saw Tim, you saw me,” and vice versa.
Timothy “Tim” Flanagan poses for a photo in 2001. (LCN file)
“He was more like a brother than anything else,” he said. “We were just always together … We went through a lot of things.”
Mellor and Flanagan are both lifetime members of the Midcoast Sports Hall of Fame, a nonprofit organization that publicly recognizes outstanding athletes and contributors to athletics in Midcoast Maine. Mellor said Flanagan joined the hall’s board of directors roughly 12 years ago, serving on the board’s nominating committee for about 10 years.
Flanagan was an ideal candidate for induction into the Midcoast Sports Hall of Fame, according to Mellor, but he was so “humble” that he did not want to be nominated. Mellor said he asked Flanagan several times for his athletic biography, as it is required of nominees to provide it; however, Flanagan would not give it to him.
“He said, ‘There are other people that are more deserving than me,’” said Mellor.
Flanagan was a caring and dependable person, whether he was on the court, in the classroom, or out in the community, according to Mellor.
“He was just a really good guy, and very positive,” said Mellor. “I don’t know anyone that would say a negative thing about him. He was someone I was proud to call a friend, and he was so sincere,”
Flanagan was always one to lend a helping hand, according to Sommers, and would often do so without expecting anything in return.
“It wasn’t in your face; it was always behind the scenes. He didn’t want any of the recognition, he just wanted things to be done and be done right,” said Sommers. “I think the turnout at his funeral … I think that just sends a clear message of how he was liked and loved by a lot of people.”
Sommers said Flanagan was “just one (person) you didn’t think would go.”
“He was always there when you needed him … I’m going to miss him,” said Sommers. “They always say, ‘You lost a good man.’ By golly, we lost a good man.”
