John "Jack" Flynn

JOHN P. ‘JACK’ FLYNN

South Portland – Born on January 27, 1938, in Danvers, Massachusetts, he passed peacefully on October 2, 2026, surrounded by family. In between, he left an indelible mark on his children, grandchildren, nieces and nephews, and the countless people he coached, counseled, and mentored.

He attended Danvers schools, graduating from the former Holten High School where he lettered in football, basketball, and track. He captained or co-captained a number of teams, and was mentored by multi-sport coach George Radulski, who served as an important and lasting influence.

In June 1960, freshly graduated from Bates College as the first college attendee in his family, he married Carol (Heldman). Their sixty-six years together were filled with devotion, adventure, and a deep commitment to family. Their journey included many countries but was always uniquely local.

From 1960 through 1993, he served South Portland High School as a teacher, guidance counselor, football coach, and athletic director. Upon retirement from South Portland, he joined his college teammate Howard Vandersea as an assistant coach at Bowdoin College and later came out of retirement again to coach Scarborough High School to its inaugural state football championship. He never stopped coaching.

He was an accomplished athlete and coach and was inducted into the sports halls of fame at Danvers, MA, high school, along with his sister, Anne, the South Portland Football Hall of Fame, the Maine Sports Hall of Fame, and was recognized by the Maine Chapter of the National Football Foundation and College Football Hall of Fame. He was selected to the Sunday Telegram All Maine Team while at Bates. He was awarded Coach of the Year multiple times. His teams won, but greater satisfaction came from the enduring connection he had with former players and counselees during their ensuing lives. He remained in regular contact with so many of them.

Jack’s faith was his compass. As a devoted parishioner of Holy Cross Roman Catholic Church, he lived his values with humility, kindness, and steadfast purpose.

Notwithstanding his many individual accolades, he would say his greatest accomplishments were his children and especially his grandchildren, Jennifer, Kiely, Christopher (Ellery), Tyler, Andrew, Elizabeth, Josiah, and Mary. He took great pride and satisfaction from each of their accomplishments but was never surprised by any of them. The arrival of great grandchild George on New Year’s Day in 2025 brought him immeasurable joy. Jack and Carol made it a point of emphasis to be present for every baptism, confirmation, graduation, and most concerts, recitals, and athletic events of their grandchildren, regardless of where they were occurring. Jack and Carol loved skiing with them at Mt. Abram in winters and spending summers with them at Higgins Beach.

Jack was predeceased by his parents, John and Rose, his sister Patricia, his in-laws Lloyd and Blanche Heldman, John and Patricia Monahan, Bob Nowak, Stanley Michalski, Carol Heldman, Lloyd “Mike” Heldman, and Lorrain Heldman. He is survived by his beloved wife, Carol, their four children and their spouses, Deborah Racine (Kevin), Catherine Solario, Brian (Gervaise) and John, his grandchildren, great-grandchild, his beloved sister, Anne Michalski, brother-in-law Dan Heldman, cousin and “little brother” Len Johnson (Janice), and a wide circle of nieces, nephews, friends, former players, and counselees. who have been grateful for his influence. A better friend couldn’t be found. He will be missed greatly, but his example will not be forgotten.

Although there were too many friendships to mention all, those that spanned fifty (50) years or more included their Bates College fellow alumni, Will and Bev Callendar, El and Eileen Guthrie, Joe and Anne Murphy, Pete and Maryellen Gartner, and Jim and Audrey Flanagan, as well as Lee and Pat Akerley, Tige and Sandy Curran, Connie and Louise Nisbet, John and Jean Sullivan, Bill and Beverly Cunnane, and Jay and Martha Vance.

The family extends heartfelt gratitude to the compassionate care teams who supported Jack in recent months, and to the Gosnell House.

Visiting Hours will be held on Thursday, October 15 from 4-7PM at the Conroy-Tully Walker Funeral Home of South Portland, 1024 Broadway, South Portland. A Mass of Christian Burial will be celebrated on Friday, October 16 at 11AM at Holy Cross Church, 124 Cottage Road, South Portland. Interment will follow at Calvary Cemetery, Broadway, South Portland. The family will host a celebration reception following the committal. To view Jack’s memorial page or to share an online condolence, please visit www.ConroyTullyWalker.com

In lieu of flowers, donations may be made to a charity of your preference.