Both Sides of the Line

Kevin Kelly's memoir, Both Sides of the Line, is a gripping, unforgettable story about a lower middle-class kid in the turbulent Boston of the 1970s whose football team, perennial losers, rise to championship level one season because of a charismatic young coach.

Clyde Dempsey, a brilliant high school, college, and semi-pro player in his own right, inculcates his charges with a unique mantra (“technique, quickness, desire”) that helps them overcome their weaknesses. He also has a warm spot in his heart for his “kids” and helps them find their way to college when otherwise their education would stop with high school graduation.

The coach, however, has a very dark other side―he's a collector for the Boston mob. Eventually, his mob job, his anger, and his affinity for cocaine get the better of him. He brazenly commits a murder in a heavily populated Boston bar, disappears, and is only brought back to face charges when someone in Toronto recognizes him during an episode of “America's Most Wanted.”

Dempsey, and his championship season, become lifelong obsessions for Kevin Kelly, who tries to bring his teammates together to assess how such a good man could also be such a bad man, too.

Son of a Boston Irish cop, Kevin Kelly grew up in Hyde Park. After his mother’s tragic death, he and his brother found stability through their father, friends, a loving stepmother, and football.

Following his brother's footsteps to Don Bosco High, Kelly nearly quit football. He was persuaded to stay by his brother's warning that he would regret it for life. Inspired by coach Jack Dempsey, the undersized team won the Catholic Conference Championship, a victory that led Kelly to play at the college and semi-pro levels. He and Dempsey later played side-by-side, winning a second championship and solidifying a lifelong bond.

When Don Bosco closed in 1998, Kelly felt compelled to write their story to preserve the team’s legacy and to understand how his mentor could "turn out to be so bad." Though writing was a 17-year "herculean task" for him, he believed the story needed to be told. Today, Kelly passes on Dempsey’s philosophy that desire and technique trump size.

After running his own construction company, Kelly earned a Master of Education from UMass and switched careers to education administration, serving as a Principal and later as Assistant Dean of Students at Deerfield Academy. He has coached football at various levels since 1980.

Kelly holds an undergraduate degree in Special Education and is married to his wife, Xiaofeng, with whom he has two daughters.