Both Sides of the Line

by Kelly, Kevin

Dempsey was shackled by the waist and sent to cell thirty-eight, the same cell where Dempsey later claimed he’d been kept shackled and naked for five days.

  “I was kept in solitary confinement, cold and without a blanket. I wasn’t given any medical attention and, for a week, they only fed me sandwiches and juice.”

  But according to Rob MacIntosh, a guard working the night shift at the Nashua Jail, there were a few facts missing from Dempsey’s account of the story.

  “Guards never put their hands on a prisoner. It’s against protocol as well as straight-out dangerous to a guard’s health. We’re simply outnumbered. Guards are trained to communicate with prisoners under the following criteria: Ask, Advise, Order. When an emergency occurs, the SERT”—Severe Emergency Response Team—“is called in to restore order but, in this case, the prisoners held the unit captive and an ‘All Call’ went out. Approximately forty guards stormed the unit. Dempsey was out of control. He took one of the guards, Chuck Wheeler, knocked him to the ground and bit the upper third of his right ear off. Dempsey knocked another guard unconscious, which sent him to Mass General Hospital. Dempsey was so strong and his bone structure so thick, they couldn’t fit the handcuffs around his wrists.

  “When I came onto my shift, I could feel something was up,” MacIntosh explained. “Everyone seemed to be on edge, even the prisoners.” To find out what had happened, MacIntosh naturally turned to his sergeant.

  “How you doing, Sarge?”

  “Better now that Dempsey’s locked up.”

  “Dempsey? What are you talking about?”

  “You haven’t heard, Rob?”

  “Sarge, I’ve been working the night shift for four years. I just came on duty fifteen minutes ago. What the hell is going on here?”

  “Okay, okay, relax. Everyone is on pins and needles and a little edgy right now. Dempsey incited a riot this morning, and he sent a few guys to the hospital. Jesus, he’s a God damn animal. Are you ready for this: He bit Chuck Wheeler’s ear off and sent Johnny O’Driscoll unconscious to Mass General. We lost the unit for ten minutes and had to put out an All Call.”

  “An All Call? Shit, when was the last time Nashua had to do that? It hasn’t happened during my time.”

  “It’s been eleven years. The veteran guards were just trying to remember during dinner.”

  And to add an extra twist to the story, it just so happened that Rob MacIntosh was also the head line coach at Bosco, and that he’d had a strong desire to connect with Dempsey prior to the inmate’s arrival at the facility. Rob had played for and later coached with Bob Currier at Bosco. Additionally, Rob’s mother had grown up in Brighton and had gone to school with Currier at St Columbkille’s.

  “My father was built strong,” MacIntosh said, “but it was my mother who was the tough one in the family. She was a Marine during the Korean War. She was so tough that years later, after we moved to Charlestown, she had a heart attack and walked to Mass General Hospital.

  “But what really made me want to connect with Dempsey was a desire to pick his brain on coaching, on teaching the offensive and defensive linemen. I had heard of Dempsey for years while at Bosco. In 1992, Skip would take over as head coach at Bosco and all I heard was ‘Dempsey would do it this way.’ ‘Dempsey would do it that way.’ ‘We’ll do it the way Dempsey did.’”

  “Where’s Dempsey held up, Sarge?” Rob asked.

  “Cell number thirty-eight. Why?”

  “How long has he been locked up?”

  “Since eight-thirty this morning.”

  “Sarge, give me the keys, will ya?”

  “Give you the keys for what?”

  “I think I can reach Dempsey.”

  “Reach Dempsey! Are you out of your mind? The guy will kill you.”

  But MacIntosh was adamant. Grabbing the keys and donning a Bosco football jacket, MacIntosh made his way to cell number thirty-eight.

  “Are you Jack Dempsey?”

  “Why?”

  “We have a mutual friend.”

  “Yeah? Who’s that?”

  “Bob Currier.”

  Dempsey, looking out his window at the pedestrians on the street, responded, “How do you know, Bob?”

  “I played for Bob at Don Bosco and later coached with him.”

  But when Dempsey finally turned to him, it wasn’t as an old high school football coach, recalls MacIntosh. “When our eyes first met, I felt like I was looking into the eyes of Satan. But then Dempsey saw my football jacket and, instantly, he transformed into Dempsey the coach.”

  “What do you want?” Dempsey asked.

  “I wanted to know if I could pick your brain about coaching both sides of the line.”

  “Well, nice to meet you,” Dempsey said, extending a hand. “Pull up a chair.”

  “And although I was nervous,” MacIntosh said, “realizing this guy could kill me at any moment, I spent the next five-and-a-half hours in his cell. During that time, I learned more about coaching football than I have in thirty years. I stood up to leave, ready to lock Dempsey in. His closing statement will stay with me as long as I live: ‘Remember, the secret to great coaching is loving your kids.’”

  Reconnecting

  “We did it all together―teacher, teammate, brother.

  Love, Coach Dempsey”

  While Dempsey was on the run in Canada, I and my teammates were still on the treadmill of life attempting to make something of ourselves. We had gone our separate ways and, for the most part, lost contact with one another.

  A year after Dempsey killed White, I was back at Bosco coaching with Currier. I knew very few of the specifics of Dempsey’s fatal encounter at Mr. McNasty’s. All I knew was that Dempsey was in Canada and that he occasionally had contact with Currier. There were even rumors that he drifted back into Boston from time to time. We all acknowledged that the death of White was a game changer for Dempsey. All of the legendary street fights and romantic tales about Dempsey collecting for the mob were now put aside, tainted and darker. And we all knew, no matter how it pained us, that Dempsey now would never be able to coach, mentor, or inspire kids again.

  I had ended my football career in 1980 when the Hyde Park Cowboys won their third championship in five years in the Eastern League of New England. In 1981, I went into business for myself, applying all the skills and determination I’d learned from football to become a parking lot maintenance contractor. I’d made plenty of mistakes, but I’d gained two core gifts given me by football: perseverance and commitment. I wouldn’t accept being defeated, although I didn’t spend too much time looking back.

  It’s hard to recall exactly what I thought of Dempsey during this period in my life. I’m sure I put his act of murder into a place and framework that worked best for me. Dempsey’s actions went too far, of course, but perhaps he’d been justified somehow. Maybe the guy he shot had been a bad guy—just like all those borrowers he’d once told me about. Maybe the guy he’d shot had known the rules of the game but simply refused to play by them. Maybe Dempsey had just been performing some kind of street or mob justice I couldn’t understand.

  I had no knowledge of White, so it was easy to create a character or personality that justified Dempsey’s deciding to kill him. It wasn’t difficult for me to root for “Street Dempsey” and somehow glorify his being on the run.

  Regardless of how I portrayed Dempsey, he was still rooted deep within me. I coached football for a number of years at different schools and, when I did, I was Dempsey. The same speeches, the same connecting of lessons learned on the field to lessons learned in life, and, of course, the same endless mantra: Size means nothing in football. It’s all about quickness, technique, and desire.

  The more I coached, the more I felt drawn to make a change in my life. I decided to work with kids full-time. So, in 1990, I sold my business and returned to school at the University of M
aine to pursue a degree in teaching. While working out in the gym, I shared some Dempsey stories with a few fellow students with whom I’d become friendly. I was in my thirties, and they were much younger―somewhere in their early twenties. When I told them about Dempsey, they had looks on their faces I knew all too well: shock, surprise, and awe. It made for great theater, and I loved playing my part.

  Before the Christmas break, one of my lifting buddies, Kapoula Thompson, found me leaving the library.

  “Hey, Kev, did you catch America’s Most Wanted this evening?”

  “No, why?”

  “Your coach—that Dempsey guy you told us about—he was the featured fugitive! They talked about him coaching at Don Bosco and how all the players loved him. They think he’s on the run in Canada.”

  It was only after Dempsey had been caught, tried, and sentenced to Walpole that I suddenly felt the gravity of White’s murder. Even so, a life sentence for Dempsey was impossible for me to comprehend.

  “I just can’t believe that he’ll spend the rest of his life in prison!” I said, shaking my head incredulously as my parents listened to the entire, wild tale.

  “Dempsey will handle Walpole with no problem,” my father said, laughing as he glanced through the Boston Globe. “Give him some time and he’ll be running the place.”

  The funny thing was, I didn’t laugh back. Instead, I could only turn and walk away, conflicted.

  What did Dempsey really mean to me after all these years?

  In April of 1996, the 1974 Bosco champions finally got some well-deserved recognition. We were inducted into the Bosco Hall of Fame. For me, it was a highlight month: I married my wife, Xiaofeng, on April 7; ran the Boston Marathon on April 15; and capped it all off on April 29 by gathering with old teammates I’d not seen in twenty-one years. But while our head coach stood with us for many of the photos, we all felt the discomfort and strangeness of knowing that our beloved line coach was locked up behind bars.

  Unfortunately for me, I was unable to spend much time reconnecting with my teammates. My wife and I had to work the next morning and had a two-hour drive back to Deerfield. So, after some quick handshakes and photos, I was out the door.

  My wife and I settled in beautiful western Massachusetts. We started a family, and both began to work in education. Xioafeng taught Chinese at Deerfield Academy (a world-famous private school) and I became the Assistant Principal of Deerfield Elementary School, a public school. Life was good for the Kellys.

  But then another rock dropped into the Bosco pond: in 1998, after forty-three years of educating and shaping the lives of thousands of inner city kids, Bosco closed its doors.

  Immediately, I was back in 1974. My teachers, teammates, coaches, the championship year—all of it wiped out and gone forever in one quick swipe.

  I realized then that we—my team—would forever own the distinction as the only Bosco team to ever win the Catholic Conference. I also realized that we were going to evaporate into obscurity if we didn’t do something soon to preserve this legacy. I decided then and there that I wasn’t going to allow our memory and achievements to slip away, and the first person I knew I needed to contact was Coach Dempsey.

  Sitting in my office, I wrote Dempsey a letter. It was a perfect, cloudless spring morning, the air was crisp, and the sun shone brightly through my office windows. Tulips—red, yellow and purple—were pushing up through the ground. A dogwood tree was budding dark red, and the birds sounded like a symphony warming up before a concert. Reclining amid all this idyllic scenery and beauty, I wondered what Dempsey was doing, seeing, and hearing at that same moment in his prison cell. What was he thinking about? What beauty was in his life? Would he remember who I was or even care?

  Dear Coach Dempsey,

  I hope this letter finds you well.

  You may not remember me, but my name is Kevin Kelly and I played for you at Don Bosco and was part of the ’74 championship team. We also won a championship together as teammates in ’76 with the Hyde Park Cowboys.

  I have coached high school football off and on over the last twelve years, and have had the opportunity to work alongside many accomplished coaches. However, I have never before met anyone who coached line technique with your level of knowledge. You were an outstanding motivator and teacher to me. The smallest details were always addressed: stance work, reading the opponent’s body, watching for shifts in a lineman’s stance, focusing on the lineman’s hand for quickness off the line. You punched into us that the average play lasts only three and a half seconds, and that if you can’t give a hundred percent for three and half seconds, go play tennis! And, most importantly, you drilled into us that size means nothing in the game of football. It’s all about quickness, technique, and desire.

  I teach all of these strategies and principles as a coach today.

  I can’t help but reflect on the number of high school players who’ve missed the opportunity to have you as their coach. I, along with many other Bosco players, feel that our championship never would have happened if we hadn’t had you as part of the coaching staff. You and Coach Currier were the perfect balance.

  I’m planning to write a book on the ’74 Bosco team and feel that you and your life story are a critical part of that story. With your permission, I’d like to come and visit you for an interview.

  Looking forward to hearing from you.

  Respectfully,

  Kevin Kelly

  A few weeks later, I received the following letter from Coach Dempsey:

  Dear Kevin,

  Great to hear from you and of course I remember you. The ’74 season was one of the most enjoyable and satisfying years of my coaching career. The memories of the players and coaches coming together for a common goal will stay with me for the rest of my life.

  I’m also glad to hear that you are coaching. The “ME” athlete is so difficult to watch on TV. The pros are hurting the purity of the game. Playing with an unselfish attitude, sacrificing for the good of the team, and connecting the lessons learned on the field to the real world, all seem to be fading.

  Keep the game pure!

  You are the only player that I ever celebrated championships with as both coach and teammate!

  Write the book!

  We did it all together,

  Teacher,

  Teammate,

  Brother,

  Love,

  Coach Dempsey

  Later, as I sat in my comfortable office looking out my window, taking in all the beautiful sights and sounds, I thought of my coach sitting in his dirty, tiny cell in Walpole. I was stunned and emotionally moved by what I’d just read. The letter brought tears to my eyes. What a tremendous waste! I thought, suddenly overwhelmed. A waste of talent, a waste of potential and, mostly, a waste of a life! How could he have thrown it all away?

  Dempsey had self-destructed—taking drugs, committing murder, breaking every rule in the book while evading arrest in Canada, and all to end up with a life sentence in prison.

  Yet here he was, writing me as if from the back porch of his childhood home; reflective, insightful, and caring. He worried about the future of his sport and about those who played it. Where had this Dempsey been during those critical moments back at McNasty’s?

  A few months went by before I wrote Dempsey again to set a date for our interview. In the meantime, I decided to meet with Currier. Currier was a man who, if nothing else, could always be depended upon for the truth—and the truth was just what I needed. After all, though I was by then a mature, mid-forties adult, there was still that part of me that wanted to see Dempsey through the eyes of my eighteen-year-old self. And Currier knew it.

  “Kevin, I know you’re excited to see Dempsey, and I know you’re going to look at him only as your coach,” Currier said, reading me with stunning ease. “But be careful. Coach Dempsey is only part of who he truly is. There’s
a dangerous and unpredictable Dempsey as well. You have a family. If Dempsey gets out of prison, he’ll gravitate to those he can reach out to. Ask yourself: If Dempsey were at your door and told you he needed a place to stay, would you invite him to live with you and your family? How would you get him to leave if he overstayed his welcome or became unstable?”

  Coach Currier sobered me up. He was absolutely right. I needed to keep my emotional distance from Dempsey.

  Dempsey had recently appealed his case. There’d been some sticky, legal loophole for him—the judge may not have correctly explained to the jury the differences between murder one, murder two, and manslaughter. Dempsey and his lawyers were convinced that his verdict would be overturned. If so, he could be free within four years.

  No matter how I felt about Dempsey, I had to admit that he was a master manipulator. And, for my family’s sake, I couldn’t afford to get sucked into his world.

  So I let more time pass and didn’t worry much about why Dempsey hadn’t yet responded to my last letter. My life as a school administrator was busy enough as it was, and, besides, being a dad and husband were my first priorities.

  It wasn’t until the fall of 2001 that I prepared to mail out my next letter to Dempsey. First, however, I called Walpole to make sure that Dempsey was still there—I was told it was not unusual for prisoners to be rotated periodically from prison to prison across the state of Massachusetts.

  “Hi, I’m just calling to see if Jack Dempsey is still being held at Walpole.”

  “Do you mean Clyde Dempsey from Allston Brighton?” asked the operator.

  “That’s the one,” I said, laughing to myself. Why had I assumed that the operator would automatically know who Dempsey was? His legend didn’t stretch that far!

  “Clyde Dempsey died last month. Are you a relative?”

  My heart fell. How was this possible? Coach Dempsey dead?

  I felt a sudden, tremendous guilt settle upon me. I felt selfish. I wondered who’d been with Dempsey when he took his last breath. How had he died? Why hadn’t I tried to visit him sooner? During his many years locked up in Walpole, some of my teammates had. If I hadn’t thought of writing the book, and if Bosco hadn’t closed its doors, would I even have thought to visit Dempsey at all?