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How High School Football Coach Clyde Dempsey Went From Mentor To Murderer10:00
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Both Sides of the Line book cover. (Courtesy Bancroft Press)
Both Sides of the Line book cover. (Courtesy Bancroft Press)
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Both Sides of the Line by Kevin Kelly. (Courtesy Bancroft Press)
Both Sides of the Line by Kevin Kelly. (Courtesy Bancroft Press)

A new memoir charts the course of a Boston high school football coach from conference champion to maximum security prisoner.

Clyde "Jack" Dempsey was the charismatic line coach of the Don Bosco Bears in 1973. Just a year after joining the now-closed technical high school, Dempsey led the perennial last-place team to victory in the competitive Catholic Conference championship. It was the only year Don Bosco won the conference.

But in a striking turn of events, less than two decades later, Dempsey would be convicted of second-degree murder and given a life sentence at Cedar Junction, where he died in 2001.

How did a beloved coach go from mentor to murderer?

Kevin Kelly was a lineman on Dempsey's 1974 team. He's written about his relationship with Dempsey in his new book, "Both Sides of the Line."

Guest

Kevin Kelly, author of "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" and assistant dean of students at Deerfield Academy, which tweets @Deerfield.

This segment aired on August 22, 2016.

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