DEERFIELD – In the fall of 1974, no one thought Don Bosco Technical High School’s football team — ranked among the worst in the Catholic Conference — had any shot at taking the championship. But with the mentorship of one of the team’s defensive coaches, Jack “Clyde” Dempsey, they did just that, completely upsetting the season.
Seven years later, however, the coach that had been such a positive force in many of the player’s lives, the same man who’d inspired them to take the season all the way to the top, was on the run from the Federal Bureau of Investigations. On July 1, 1981, he’d fired a bullet straight through a man’s chest during a bar fight in Boston, killing him.
Kevin Kelly of Deerfield, the assistant dean of students at Deerfield Academy, was a linebacker on the team that year, and was privy to all of it: to the championship season as a player on the team, and to his former coach’s crime from whispers in his youth of Dempsey’s possible involvement with the mob to the story being aired on America’s Most Wanted.
Now, he’s recounted it all in his new book, “Both Sides of the Line: The True Story of the Life-changing Football Mentor Who Became A Long-time Target of America’s Most Wanted.”
“Both Sides” is Kelly’s first book, which he said he wrote on-and-off for about 17 years. He said he got the idea to write his tale after seeing a Boston Globe article about the closure of Don Bosco, in Boston, in 1998.
“Two immediate thoughts went through my mind at that moment,” he said. “That the ’74 team would go down as the only team in the school’s history that won the Catholic Conference, and that we would fade into obscurity.”
Over the years, he’d write, then let it sit, then pick up writing again, trying to pen his tale on paper. But his breakthrough didn’t come until 2013, when he tracked down some of his former teammates to arrange a reunion. At the event, decked out in their game jerseys, they discussed Dempsey, the impact he had on their lives and the story of his eventual downfall after a descent into drugs. That changed the focus of his story entirely.
“It was first driven with the intent that it was my story, then halfway through I realized it was our story,” he said. “This guy had a tremendous influence on us. And it’s sad.”
Coach Dempsey, it turned out, had been not just a central factor in the team’s championship season, but also in many of their lives and personal development. Many of the players had come from broken, dysfunctional homes, he said, and some recounted decades later that the support and stability Dempsey gave them as a coach made all the difference.
“Statistically, they should have been dysfunctional and divorced, but nobody was,” he said of his teammates. Some had gone on to become top military officials or successful businessmen. “It was interesting to see how well-rounded many became.”
Kelly said Dempsey was a “phenomenal” coach and a father figure of sorts to many of his teammates, working to help them get into college and supporting them in other ways even after they’d graduated. “He had no children, and I think he took it upon himself that we were his boys. He was committed to making sure we had the life he didn’t.”
The championship season, he said, laid a foundation that they “could be anything they wanted to be.”
“He was a master teacher,” Kelly said. “I couldn’t put it in any other terms. What he gave us was to believe in ourselves. There’s no doubt.”
It was the contrast between Dempsey’s positive role in their lives and his darker, criminal side as a street enforcer and, later, convicted murderer that made him a particularly interesting character.
“It was the Doctor Jekyl and Mr. Hyde life he was leading. He’s preaching God, family and country — demanding the best out of his boys — while at the same time working for the mob and that whole bit,” Kelly said. “Why, what led him to do that? Dempsey’s life was a story.”
Dempsey’s attention to detail, technical proficiency and high-energy, highly-motivating persona made him the best coach Kelly said he ever played under, and some of those same things made him the “ferocious” street fighter that afforded him a level of respect on the “other side of the line.” Rumors had it that he was working as hired muscle, collecting for the mob, Kelly said — and he claims this was confirmed to him later by Dempsey himself — among other dark deeds, until the fateful night that he took a man’s life.
Eventually, Dempsey was caught and sentenced to prison for the rest of his life.
Kelly also played alongside Dempsey on a semi-professional team, the Hyde Park Cowboys, where the pair won a championship together. There, he saw more of the Dempsey’s deftness as an athlete and inspirational nature.
Twenty-two years later, Kelly said he wrote a letter to Dempsey while he was in prison, before his death. He didn’t expect him to remember him, but he received a reply in which the duality between the lighter side of the man who was his former coach, teammate and mentor and the dark side that led many to consider him a monster, shone through.
“At the end of the letter, he wrote, ‘Kevin, you’re the only person I’ve ever coached and played with and won a championship. We did it all together, teacher, teammate, brother,” Kelly said. “It was astounding to me, it was like he was writing from the back porch of his house, when he was in prison. Where’d that come from?”
Kelly’s book can be purchased online, and he said he expects it will available in local bookstores by April.
Tom Relihan started at The Recorder in 2014, where he covers health, human services and education. He can be reached at 413-772-0261 x 264 or at trelihan@recorder.com