Football extends far beyond a Boston high school’s field in Kevin Kelly’s memoir, Both Sides of the Line, which is set to release July 1, 2016. Following in his brother’s footsteps and eager to escape his inner-city roots and mother’s suicide, Kelly played high school football from 1971-75. His coach, Jack Dempsey, augmented his desire to play, teaching Kelly lessons on the field that served as life lessons off the field. Despite rumors about Dempsey’s past as a mob collector and drug addict, Kelly and his teammates revered their coach. When Dempsey committed murder and fled the state in 1981, the author’s admiration still didn’t waver, but his lifelong obsession with his coach began.
Kelly attended Saint Don Bosco Technical High School in Boston, an all-boys Catholic school. There, Kelly was taught religious values; however, he was moved more so by the values that Dempsey instilled in him each day at practice. Dempsey’s motto was “Size means nothing. It’s all about quickness, technique, and desire.”
With his motto, Dempsey helped many of his players better their games; he also advised his players on issues in their personal lives and helped them get into college. “He gave us the belief that we could achieve anything in our lives if we worked hard enough,” says Kelly. “All of us walked away with that.”
Despite how he lived out his own life, Dempsey told his players that drinking and drugs would be death sentences to their performances. Many players disregarded his advice, but Kelly didn’t want to let his coach down; he stayed clean throughout his high school football career and throughout his adult life. His youngest daughter often asks, “Daddy, you must have?” He’s proud to always respond with a “no.”
As a football coach himself, Kelly has been lucky enough to have players who’ve avoided drugs and alcohol during the football season, but he knows some players had issues outside of the season. “As a coach, I’d try to do a lot of pre-coaching,” says Kelly. “I try to be proactive versus reactive.” He tells his players that they can’t be hypocrites and play for him, saying to his players “If you plan on doing it [drugs], do yourself and teammates a favor and turn your uniform in beforehand.” As assistant dean at Deerfield Academy in Massachusetts, Kelly is charged with disciplining students who’ve violated the school’s drug and alcohol policy. “I don’t punish anyone,” he says. “I teach consequences. I want the students to stop, think, and reflect, so that next time they’re in that position, they’re going to ask if it’s worth it.” Clearly, Dempsey’s lessons of self-discipline served Kelly well.
However, Dempsey’s lessons sometimes pushed his players too hard. During a routine practice, Michael, the quarterback, was paralyzed after a grueling drill. When he collapsed on the ground, Dempsey ordered the others to continue without checking on him. If they had been allowed to, Michael’s mobility may have been spared.
Kelly reunited with his teammates when writing his memoir, and every player the author spoke with said that he regretted falling out of touch with Michael. Michael died near the end of writing the memoir, and Kelly says going to visit the family for the funeral was very difficult. “We all felt a level of guilt for disconnecting and not staying in touch,” says the author. “He and his moment never left any of us.”
Following Michael’s incident, Kelly contemplated quitting the team, but Dempsey finally had them on the path to victory. With the 1974 Catholic Conference Championship in sight, Kelly decided to remain. Despite his coach’s brutality, he and his teammates knew that Dempsey would lead them to a long-awaited win.
And that he did. After a high school career full of losses, Kelly was on the 1974 championship team his senior year. The pride he felt pushed him to pursue football in college. However, Kelly focused on football over academics and ultimately flunked out, but his failure turned into opportunity when he landed a spot on a New England semi-professional team, the Hyde Park Cowboys; Dempsey was also a player for the team.
During that time, Kelly became friends and teammates with his former coach. Many players spent their free time drinking and indulging in cocaine. Wild stories about Dempsey’s whereabouts following his cocaine use were popular among the teammates; however, Dempsey only drank lightly around Kelly and never used cocaine. Still, Kelly saw a hot-headed Dempsey blow up several times.
After a year with the Hyde Park Cowboys, Kelly improved his grades at community college and was offered a position on the University of Hawaii’s football team. When he left, he didn’t know that he would never see Dempsey again.
During Dempsey’s lifetime, he went before a judge 14 times, and after Kelly left for Hawaii in 1977, Dempsey’s charges became more severe. In 1981, fueled by alcohol, drugs, and his easily triggered temper, Dempsey shot and killed a man in a bar after tense exchange. After the murder, Dempsey fled to Canada and assumed a new identity. Nine years later, he appeared on America’s Most Wanted and was eventually identified and sentenced to life in prison.
In 1998 Don Bosco closed its doors. In 2001, Kelly learned that Dempsey had died in prison. Feeling little closure, Kelly decided to track down his old high school teammates and decided to finally commit the story of Jack Dempsey to writing. He reconnected with his high school teammates in 2013 – 39 years after the 1974 championship game victory. At the reunion the players spoke about the impact football and Coach Dempsey had in their lives; it was clear that their coach had helped lead these boys from inner-city Boston into successful careers and loving families. Thirty-nine years later, they all still had an immense respect for their coach. “It started out as my story but ended up being our story,” says Kelly about his memoir.
Kelly compartmentalizes Dempsey, taking away all he can from what he calls the better side of his former coach. “I’ve taken the best of Dempsey, and I have ingrained that in me along with my own personal beliefs,” he says. “I echo much of what he gave me in the sense of his purity for the game and the demand that his boys play with class.”
Football fan or not, Dempsey’s double-life and Kelly’s respect for the better half of his coach will keep readers intrigued until the very end. Kelly’s story is not just about the love of a sport; it’s about finding something in life to motivate and drive you, and it’s about remembering the past in order to build a better future. Inner-city boys grew up to become educated entrepreneurs, coaches, and fathers because of one man’s influence, and that’s not something that can be said about most people in life. When Kelly interviewed his teammates for his memoir, every one of them said that they cherished their children most. The last time Dempsey was visited in prison, his advice was “If you want to be a good coach, you got to love your kids.” It sounds like his kids are still listening.