A charismatic football coach can make a deep and lasting impression on his high school charges. Clyde Dempsey certainly did that in 1974, when he turned Boston's Don Bosco High – a perennially losing inner-city team – into an overnight champion with his emphasis on quickness, technique, and desire. While a nice,inspirational story, what sets it apart is the exploration of a darker side to the coach that author Kevin Kelly, who played for Dempsey, reveals in “Both Sides of the Line.” Unbeknowst to his young players, Dempsey was a Mob enforcer. In 1990, after being featured on “America’s Most Wanted” TV show, Dempsey was apprehended in Toronto, convicted of second degree murder, and died in prison in 2001. Kelly, who coached football at many levels before taking an administrative job at prestigious Massachusetts prep school Deerfield Academy, never had an opportunity to interview Dempsey. But his desire to know his former coach’s full life story comes through in this retelling.
Here’s an excerpt from Both Sides of the Line:
“Listening to [coach] Dempsey, I had a strong feeling my junior year was going to be something entirely new and exciting. I was determined to give him that one hundred percent and make a true contribution to the team. I felt secure and safe around Dempsey, but from a distance. Although he was relaxed and easygoing around us, we had heard enough stories about what he could be on the street to ever get too comfortable with him.
“As high school boys, we loved these stories. It put our coach on a pedestal. It was like having a really tough dad. My dad can beat-up your dad type of thing. As football players, we knew Dempsey was the real deal, a truly tough guy – a guy who could walk the walk.”
