Both Sides of the Line

My Coach, the Boston Mob Enforcer; My Mentor, the Murderer; the True Story of Clyde Dempsey and the 1974 Don Bosco Bears

Kevin Kelly

High school players in a working class neighborhood of the 1970s gain desperately needed structure and guidance from Jack “Clyde” Dempsey, a scrappy, charismatic coach who seems like nothing more than a football geek. But “Coach” also happens to be the toughest guy on the streets of Boston, with a temper to match, and it’s his secret life as a mob enforcer/collector that forces him to flee the country, becoming one of America’s most wanted. In this memoir, a devoted Dempsey disciple, who later becomes a dean at a world private school outside Boston, tries thirty-five years later to understand his former coach, role model, and mentor—both his good side and his very dark side—and Dempsey’s impact on his own life. A completely true story.