Both Sides of the Line: The True Story of a Life-Changing Football Mentor Who Became a Longtime Target of America's Most Wanted

by Kevin Kelly

High school players in a working-class neighborhood in the 1970s gain desperately needed structure and guidance from Jack "Clyde" Dempsey, a scrappy, charismatic coach who seems like nothing more than a football geek. But Coach also happens to be the toughest guy on the streets of Boston, with a temper to match, and it's his secret life as a mob enforcer/collector that forces him to flee the country, becoming one of America's most wanted.

In this memoir a devoted Dempsey disciple, who later became a dean at a private school outside Boston, tries 35 years later to understand his former coach, role model, and mentor - both his good side and his very dark side - and Dempsey's impact on his own life. A completely true story.

Audible Audio

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.