Mr. Kelly's Book: Both Sides of the Line

THIJS WITTINK/DEERFIELD SCROLL

Deerfield’s Student Life Office Senior Associate Kevin Kelly published his memoir Both Sides of the Line with the help of Bancroft Press in 2016. 

The book covers Mr. Kelly’s experience with Jack Clyde Dempsey, his high school football coach, who led the team to a championship season. While Dempsey acted as a mentor and leader for many high school students, including Mr. Kelly himself, his hidden identity as a mob enforcer forced him to flee the country, becoming one of America’s most wanted fugitives. 

Decades after graduation, Mr. Kelly came across a Boston Globe article featuring his Catholic high school, where he played under Dempsey. He remembered initially that his 1974 football team won their Catholic conference championship, the first time his school had ever won.

Dempsey, a longtime role model and teacher, “preached God, family, and country.” At the same time, Mr. Kelly explained, Dempsey worked for a mob, ended up killing someone, and was mentioned on the TV show America’s Most Wanted—a strange and unnerving character tension. Mr. Kelly felt like the story was worth sharing with others and decided to write about it.

Throughout the writing process, Mr. Kelly faced a big challenge: writing consistently. He shared, “For multiple years, I put the book down for a couple of months then picked it back up again, being inconsistent with the plan.” It was his publisher and close friend for the past ten years who advised him to “stop pretending to be a writer, [and] tell the story.” Mr. Kelly felt that this piece of advice “really opened the doors to continue the memoir after years of work piling up.” The book ended up taking him 18 years to write. 

Mr. Kelly had never seen himself as a writer, he said: “Writing has always been and continues to be my weakest area,” he explained. Through his experience of writing Both Sides of the Line, Mr. Kelly learned to put himself into the reader’s shoes by coming up with questions when developing the storyline. 

“Not being a writer,” he said, “I had to look at something and say to myself: Is this worthwhile? Is there anything of value here, and who would want to read this story?” 

During the process of crafting his book, Mr. Kelly found it “daunting at first,” but halfway through, he felt a burst of motivation. “I felt the runner's high kick in and felt driven to continue finishing the book,” he said. 

Back in Deerfield, he spoke about his book following its release. For one class period, Scroll Faculty Advisor English Teacher Justin Romick invited Mr. Kelly to speak in his Creative Non-Fiction Workshop, where Mr. Kelly shared a synopsis of his book. 

Julie Yan ’26, a student in Mr. Romick’s class shared her insight about the memoir: “The book is really compelling because it shows the dual perspective of the football coach. On one hand, the coach was a father figure to the team, changing the lives of so many young people, but on the other hand, he killed someone and was in the mafia,” she said. Yan emphasized how the book is not only a one-dimensional story, but it also explores the multifaceted identity of a person. 

As Mr. Kelly began to discover the other side of his football coach he had never seen, he decided to separate the coach’s admirable side from his criminal side. “I noted down the positive traits of being a role model, providing life lessons, and giving good coaching advice,” he said. 

As the main takeaway, Mr. Kelly noted how he hopes for readers to decide if Jack Clyde Dempsey was a hero or a villain by creating a book with an open-ended conclusion.