It is with heavy hearts that we announce that Timothy John Flanagan passed away peacefully on Dec. 6, 2024, surrounded by his loving family in his home in Wiscasset.

Born on Oct. 17, 1946, in Rockland, Maine, Tim was one of nine children of James and Eileen (Spinney) Flanagan. Raised in a close-knit family, the values of generosity and love became hallmarks of his life.  

Tim was known for his boundless kindness and unwavering support for those around him. His generous spirit touched the lives of many, leaving a lasting impact on all who had the privilege of knowing him. Tim’s dedication to family and community was evident in every action, as he consistently put the needs of others above his own. Even in his final days, he was more concerned about his family than his own dire situation.  

Tim’s life was marked by deep commitment to his family, who were the center of his world. He is survived by his beloved wife of 55 years, Judy (Shea) Flanagan, and their children: Darin and his wife Taryn and their children Aiden and Ashley; Donald and his wife Vicki and their children Trevor and Abby; and Doreen and her partner Rick Vachon. He is also survived by his last remaining sibling Kathleen (Flanagan) Martin and her husband Jeff, his brother-in-law Chuck Shea and his wife Faye, his sisters-in-law Sandra Shea and Yang Shea, as well as many, many, many nieces, nephews, cousins, and other extended family.  

Tim graduated from Rockland High School in 1964. Drafted into the U.S. Army in 1965, he was selected to attend the U.S. Military Academy Preparatory School at West Point. In 1969, he married Judy, whom he met at Gorham State Teachers College (now the University of Southern Maine). Tim began his teaching career at Westbrook High School in 1971 and later moved to Wiscasset High School, where he taught from 1977 until his retirement in 2017. His love of teaching and helping students was so strong that even in retirement, he continued to share his love for teaching for a few more years at Lincoln Academy and Winthrop High School. 

In addition to teaching, Tim was a dedicated board member of the Midcoast Sports Hall of Fame, which honors athletes, coaches, and teams past and present. It was his advocation that made it possible for Wiscasset to be included in the Midcoast Sports Hall of Fame. 

As a teacher, “Mr. Flanagan" profoundly impacted generations of students (especially at Wiscasset High School). Tim was known for starting his workday before normal school hours and often locking up the school on his way home. He created a safe and welcoming environment for generations of students–often providing snacks and drinks purchased on his own and kept in a small fridge in his classroom. He was always willing to help students with their academic work but his lessons on work ethic, preparation, and good moral character were perhaps some of his most important lessons.  

Tim’s contributions extended beyond the classroom to the sports fields and courts where he was best known as Coach Flanagan. He coached basketball, golf, cross-country, track, baseball, tennis, and even the math team. Among his many accomplishments, he is best remembered for leading the Wiscasset’s boys’ basketball team to Wiscasset’s first state Men’s Basketball State Championship in 1991. Under his guidance, Wiscasset teams also won multiple State Math Team Championships, a State Golf Championship, and numerous conference and regional championships.  

Tim’s passion for golf began as a young child when he would walk seven miles along Route 1 from his home to the Megunticook Golf Club, where his father worked as the head golf professional. It was there that Tim’s father taught him the love for the game of golf (both instructing and playing) that Tim would eventually pass along to multiple generations of his own family and countless junior golfers at Wiscasset High School. Tim worked his way up from caddying at Megunticook to becoming the caddy master at the Portland Country Club. His golf accomplishments span decades where he won numerous titles, including the Maine Junior Championship (1964), the Maine State Father/Son Championship (2007), and multiple club championships at Rockland Golf Club, Wawenock Golf Club, and Sheepscot Links Golf Club. Even with success throughout his golf career, Tim firmly believed it was more than just a sport—it was a platform to teach values like honesty, sportsmanship, and integrity.

Tim’s legacy of compassion, generosity, and selflessness will continue to inspire those who knew him.

A Celebration of Life will be held at Wiscasset Middle High School (272 Gardiner Road, Wiscasset, Maine) on Dec. 14 from 2 to 4 p.m. where family and friends are invited to gather and honor the extraordinary man that Timothy was. In honor of Tim, attendees are encouraged to dress casually in green to reflect his pride in his Irish heritage or in red and black to honor his legacy at Wiscasset High School. 

In lieu of flowers the family requests donations be made to promote and assist youth in playing golf around the state. Every $5 donated will provide a round of golf to one junior golfer. 

Donations can be made to: Maine Golf, c/o Tim Flanagan, Youth on Course, 2 Old County Road, Freeport, ME 04032.