When Kevin Kelly was on the 1974 Don Bosco Tech football team in inner-city Boston, back in the 1970s, he loved his coach. Years after Kelly graduated, he still quoted what his coach, Clyde Dempsey, told him throughout school.
Coach Dempsey coached the kids all the way to the Catholic Conference championship and the memories of that time in Kelly’s life stayed with him, even when he began coaching as well.
However, Dempsey had a dark side that Kelly documented in his book 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. A few years after Kelly graduated, Dempsey became a mob enforcer, ultimately killed a man and ran from the law to Canada, where he “found” a new identity — thanks to the name of a baby that he got off of a gravestone. He was captured after an episode of “America’s Most Wanted” aired with his story.
We had the chance to interview Kevin Kelly recently (you can listen to the full interview here) and found both the book and the interview with Kelly to be fantastic. This is a book that should be on your must-read list this year.
Here is a short Q&A with Kelly:
How, after high school, have you implemented the life lessons you learned on the football field? Football gave me the foundation to never quit, especially when moments in life became difficult. My first three years in business were very challenging, and many times it would have been easy to quit. I attribute my succes in business directly to the lessons I learned on the football field.
In what ways did your coaches inspire you? What did they teach you? My coaches pushed me to limits I didn’t know I could handle. They inspired me to believe that, through hard work, I could achieve anything on the field and in life.
Coach Dempsey had his faults however and one such time was when he made his players run a hard drill, just to teach them a lesson about standing around. The drill was, in Kevin Kelly’s words, ‘insane,’ and one player Michael Monahan suffered the consequences, breaking his neck in the process. It left him paralyzed from the neck down for the rest of his life.
“After the accident, which Coach Dempsey recklessly caused by requiring us to perform and inherently unsafe drill on the field, I and most of my teammates, were numb and in a fog. Also, and probably most important, quitting was social suicide at an all-boys school. But the fear never truly left me; I just learned to place it in a box,” said Kelly.
How different would your life had been if there hadn’t been a Clyde Dempsey? If our coaching staff at Bosco had never changed, we would have continued to lose and I would never have been inspired to continue football behind high school. Dempsey’s attitude and philosophy were embedded in my DNA. He was much more than a coach!
What lessons do you try to instill in your players? Size means nothing. Quickness, technique and desire are everything. Play with class. When you win, act a certain way. When you lose, act the same way. There is value in winning and losing. Strive to win, but it’s never guaranteed.
If you could convey one message from your book, what would it be? My teammates benefited immeasurably from using what I call the Dempsey mantra, both in football and in life: “Technique, quickness and desire trump all.” It is a huge irony that Dempsey squandered his enormous gifts by ignoring his own mantra and I will believe that until I die that the key part of the Dempsey life message is that “using drugs defeats even the best people.”
Both Sides of the Line is tackles the true meaning of competitive sports and what the name leaves those after they’ve left the game — from the gridiron to the iron bars of prison. The book is published by Bancroft Press and is available on Amazon.
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