Both Sides of the Line: The Coach and the Mob Enforcer, the Mentor and the Murderer; The True Story of Clyde Dempsey

Similar to John Feinstein's A Season on the Brink and Pat Conroy's My Losing Season, school administrator Kelly's memoir of his senior season at Don Bosco Technical High School in Boston's powerful Catholic Conference is a fascinating story of the rise of a perennial bottom-feeder to a league championship. Kelly's rags-to-riches account is interspersed with adversity and triumph and centers on Clyde Dempsey, an inspirational but controversial coach whose life and tragic end dominates the book. Dempsey spent time as a mob leg breaker and likewise nine years on the run in Canada after killing a man in a bar fight in 1981. After extradition back to Massachusetts, Dempsey was convicted and sent to prison, where he died in 2001. In 2014, Kelly and his teammates held a reunion, reflecting on their championship season, their current lives, and Dempsey. Throughout the narrative, Dempsey's mantra of coaching shines through: quickness, technique, and desire.