Both Sides of the Line: The Coach and the Mob Enforcer, The Mentor and the Murderer: The True Story of Clyde Dempsey

by Kevin Kelly

We all come in shades of gray, always battling back the smoke and shadows, but what happens when the darkness takes over, when what is done cannot be undone?

Kevin Kelly’s Both Sides of the Line tells the story of Jack Clyde Dempsey, football coach at a Catholic school in Boston—the man who forever changes the lives of countless young men. He brings unity and discipline and a seemingly magic mantra to a group of inner-city boys for whom football is a means to escape the many challenges faced at home. With charisma and unrelenting determination, Dempsey insists on quickness, technique, and desire―what he calls “the holy trinity” of being a good football player―and converts a group of non-winners into believers.

He also makes them into teammates who support and believe in one another. And while his team, his football family, quickly comes to respect him for his unwavering belief in their potential, the truth is, the storied and mythic nature of Dempsey’s “dark side” has preceded him. While revered by the streetwise boys well before they ever lay eyes on him, Dempsey reveals an unapologetically street-tough temper, and his whispered-about dealings with the local mob are multiplied in the rumor mill of Don Bosco High.

And when a teammate is paralyzed partly because of a Dempsey excess, linebacker Kevin Kelly begins to reconsider his faith in the game of football. And though Dempsey stays on as their coach, the ghostly memory of the crippled teammate lingers in the minds of teammates for decades.

In the fall of 1974, with team morale at an all-time low, Dempsey’s relentless drive for perfection leads his undersized charges to a championship season—the first and only title Don Bosco’s football team will ever know while competing in the prestigious Catholic Conference. The crown becomes the motor for many a player’s self-esteem and confidence as well as for their college and career success.

For Dempsey, however, it only becomes the towering peak from which he will spiral downward, crashing in a blast of violence that, one fateful night, wipes away the life of a young patron, Edward White, in a Boston bar. A football coach who preaches God, family, and country, and the need to live a clean, drug-free life, allows his penchant for drinking and cocaine to finally get the better of him.

Fleeing the scene with a gun and soon a false identity, Dempsey reinvents himself as Ronald Mior in Ontario, Canada and remains on the run from the law for ten years, even reaching the top rungs of “America’s Most Wanted” list.

This is the remarkable story of an unlikely team of winners from some of the roughest parts of Boston, and of the coach who both inspires and shapes them into believing in themselves, to achieve remarkable heights of lifetime success, as he himself self-destructs.

This is Kevin Kelly’s memoir about Jack Dempsey, the man who played on both sides of the line.

318 pages, Kindle Edition

First published March 1, 2016

Reviews

[Bert Robbens · Rating 5 out of 5]

This book was so far from my usual reading I was shocked how much I liked it. The writing is far from professional, but it's so simple and honest it has a realness that a more polished product could never achieve. It's a memoir about a kid playing high school football and the lessons he learned from a charismatic coach that carried the author and his teammates through successful and fulfilling adult lives. It contains a mystery about the coach's dark side that led him to commit a senseless murder and be put away for life in prison. Wisely, it focuses on the life of the author and leaves the mystery as just that - a mystery. I happen to love football (as a spectator), which may have given the book a bit of extra interest for me, but it is the human side of the story that makes this a great read. I highly recommend it to anyone who cares about people.

[Damon Cerrone · Rating 2 out of 5]

I grew up in Boston during busing. I went to the sister school of Bosco run by the Salesian Brothers, Saint Dominic Savio high school. Share many of the same characters in stories of going to Catholic school. The best memories are our basketball games against Bosco. Two power houses in the 70s and 80s the issue I have with the book is Kelly seems arrogant. The book was more about him and how he was able to survive the turbulent times in Boston during the 70s and 80s .We all know guys like Dempsey. Great athletes and could help us on the field or basketball courts. However, the people who cared about us, the most helped us realize. they weren’t good people. I believe the word psychopath or sociopath describes them best. I’d love to know how the white family or all the diseased gamblers and their families whose lives or ruined by the mob feel about this book And its author.

[Walker Adams · Rating 5 out of 5]

This book did a great job at displaying Coach Clyde Dempsey’s internal conflict. Love hearing about Catholic Conference football too!

[Sue · Rating 4 out of 5]

This was an interesting story to read. You don't always know someone deep inside when you are their teammate, student, or coach. I realized while I was reading this book that there are a large number of individuals going through 'something', you may not see it.