Obituary: John P. “Jack” Flynn
Former South Portland High School Coach Jack Flynn Dies at 88
South Portland, Maine – John P. “Jack” Flynn, a long‑time educator, coach, and community pillar, died peacefully on October 2, 2026, surrounded by family. The 88‑year‑old, who spent more than 30 years shaping young athletes and minds at South Portland High School, left behind a legacy that extended far beyond the football field.
Flynn was born in Danvers, Massachusetts, on January 27, 1938. He attended Danvers public schools and graduated from Holten High School, where he earned letters in football, basketball, and track. He went on to Bates College, graduating in 1960 as the first member of his family to receive a college degree. While at Bates he was named to the Sunday Telegram All‑Maine Team and later served as an assistant coach at Bowdoin College after his retirement from South Portland.
“His greatest accomplishments were his children and especially his grandchildren,” the obituary noted, a sentiment that echoed in the community’s remembrance of a man who treated every former player with the same devotion he showed his own family.
Flynn married Carol Heldman in June 1960, and the couple celebrated 66 years of marriage. Together they raised four children—Deborah Racine (Kevin), Catherine Solario, Brian (Gervaise), and John—and raised a large extended family. His grandchildren, including Jennifer, Kiely, Christopher (Ellery), Tyler, Andrew, Elizabeth, Josiah, and Mary, and great‑grandchild George, whom he welcomed into the world on New Year’s Day 2025, were central to his life. The family often spent winter ski trips at Mount Abram and summer beach days at Higgins Beach.
From 1960 to 1993, Flynn taught, served as guidance counselor, coached football, and acted as athletic director at South Portland High School. He was known for his calm demeanor and steady mentorship. After retiring, he joined former college teammate Howard Vandersea as an assistant coach at Bowdoin, then came out of retirement to coach Scarborough High School’s inaugural state football championship team, proving that his passion for coaching never faded.
His contributions earned him induction into multiple halls of fame: Danvers High School, the South Portland Football Hall of Fame, and the Maine Sports Hall of Fame. The Maine Chapter of the National Football Foundation and College Football Hall of Fame also honored him, and he received Coach of the Year awards on several occasions. In addition, the local press frequently highlighted his leadership and the respect he commanded among athletes and colleagues.
Beyond athletics, Flynn was a devoted parishioner at Holy Cross Roman Catholic Church. He described his faith as a compass that guided his actions, emphasizing humility, kindness, and steadfast purpose.
He predeceased his parents, John and Rose, his sister Patricia, and several in‑laws and relatives. He is survived by his wife, Carol; his four children and their spouses; his many grandchildren and great‑grandchild; his sister Anne Michalski; brother‑in‑law Dan Heldman; cousin Len Johnson; and a broad circle of nieces, nephews, friends, former players, and counselees.
A celebration of his life will be held at Conroy‑Tully Walker Funeral Home on Thursday, October 15, from 4:00 to 7:00 p.m. A Mass of Christian burial is scheduled for Friday, October 16, at 11:00 a.m. at Holy Cross Church, followed by interment at Calvary Cemetery in South Portland. The family will host a reception after the committal. A memorial page can be found at www.ConroyTullyWalker.com, and donations may be made in his honor to a charity of choice.
Flynn’s impact on generations of students, athletes, and family members remains a testament to his enduring commitment to mentorship and community service. His legacy will be felt for many years to come.
