Both Sides of the Line

by Kelly, Kevin

  “After high school, I attended Bridgton Academy in Maine for a postgraduate year, and later was lucky enough to attend Xavier College in Ohio. Unfortunately, things didn’t turn out like I planned. When the coaches saw how small I was, they gave me the run-around. They sent me to the equipment manager, who sent me back to the coaches. Finally, I’d had enough. The equipment manager, tried to tell me that he didn’t have any equipment for me when I was looking at a wall full of equipment behind him! ‘I don’t mean to be disrespectful,’ I said to him, ‘but what the fuck is all that equipment behind you?’ I got so frustrated that I called my father and asked him to mail down my own shit.

  “I finally got the chance to prove myself on the football field, though. Two seniors were fighting for the starting center position and I got the opportunity to meet each one by way of the pit-drill. I was so fired up, I could’ve taken on King Kong and killed the son-of-a-bitch! I exploded out of my stance, drilled the first senior, and nailed the running back! I was so revved. I turned to the coaches and said, ‘Let’s do that again!’ So the next senior jumped in, and it looked like an instant replay. I drilled the second senior and nailed the back again. My adrenaline was running so high that I actually turned to the coaches and said, ‘Gentlemen, I have arrived.’

  “One of the coaches came over and said, ‘That was impressive, Dempsey, but these guys aren’t going to go up against anyone your size.’ Soon, the team started scrimmaging and the coaches just ignored me. After that, it was all downhill. I couldn’t get on track academically and, after a few months, I wanted to call it quits and go home. My father wanted me to stay, and things got heated on the phone. I ended the conversation by saying, ‘Fuck you,’ and I hung up on him. Later that day, while changing a flat tire, he dropped dead from a heart attack. After my father’s death, I made a commitment to take care of my mother. Years later, I bought her a house and I promised never to leave her.”

  We sat in silence for a moment. I had always looked at Dempsey as solid, both physically and emotionally, but here he was, letting me view a part of his life that few people—and none of his players—had ever had access to. I was discovering that he had scars from old wounds that had never fully healed. We were both from similar backgrounds. I could tell that the finality of his father’s death had badly affected him. When you realize that you can never speak to your parent again, it’s gut-wrenching. I understood, but still I didn’t tell him, and never did tell him, of my mother’s death—this was Dempsey’s time. He was opening his inner world to me, and I didn’t want to redirect the flow of the conversation. But he was quick enough to do that for me, changing the subject on a dime:

  “So, Kevin, you ready for Hawaii?”

  Looking back, I now understand that, at that moment, Dempsey had shared enough of his past with me. He didn’t have it in him to give me any more than that.

  “I’m not sure if I’m ready, to tell you the truth, Coach,” I said. “But if I was ever gonna be ready, it’s because of you. Seriously, thank you again for everything you’ve done for me.”

  With both hands, Dempsey grabbed me by my shirt, shook me, and barked, “I didn’t spend my Friday evenings all summer long getting you ready if I didn’t think you could play! Remember what I’ve always told you: They put their pants on one leg at a time, just like you, Kel.”

  Then the shaking stopped and he wrapped me up in a hug. I knew I would really miss him, but I had no idea it would be the last time I’d ever talk with him.

  On August 19, I boarded a United Airlines 747 feeling excited and ready. This was my first time flying, and I was headed to beautiful, exotic Hawaii.

  As the plane pulled away from the gate, I saw my entire family, a few friends, and my high school girlfriend all waving goodbye. I saw Anne, my sister—still only six years old—pressing her hands and face against the window, seemingly wondering, Why would he choose to leave us?

  I’d been so self-absorbed that I hadn’t thought much about this moment until I was already knee-deep in it, and suddenly I felt a lump in my throat.

  Some of my friends and neighbors were very confused about my decision to move to Hawaii.

  “Why would you want to live there, for Christ’s sake? Apply for a Civil Service job, get married, raise a family here in Hyde Park where you belong, put in your years, retire, and collect a pension.”

  “What’re you going to do if things don’t work out?”

  “Stay with your own kind, Kev.”

  “What’re you running away from?”

  But still I struggled to see what was so complicated. Who in their right mind would give up an opportunity to live in Hawaii? I never wanted to look back on my life with regrets, and so for me the decision was easy.

  Now there was no turning back—I was headed for a new life on the other side of the world.

  Downfall

  “Are you Clyde Dempsey?”

  “No, I’m Ronald Mior. I’m Canadian. I’ve never been to America.”

  — Detective Sid Millin, Ontario, Canada

  From 1977 through 1980, Dempsey’s use of cocaine only intensified. He took to carrying his gun more often when he was out at night. People close to Dempsey were starting to see him more frequently out of control and even completely unglued.

  He began to struggle with his role as mentor and coach at Don Bosco.

  “There were times when he didn’t show up for practice,” Sylva later told me. “It was so unlike Dempsey, and no one knew exactly what was going on, but it hurt us as a team.”

  Dempsey had always had the utmost respect for Coach Currier, and though Currier knew this, there was no way Dempsey could continue on at the school as unhinged as he’d become. In 2001, Currier and I met in Brighton for lunch and he told me, “I think Jack knew he was heading down a different path. There were areas in his life that I stayed away from. And if we ever did talk about his darker side, then the conversations were always initiated by him. Then one night, near the end of the season, we were sitting at a bar in Quincy Market and he promised me he’d never do anything to hurt me, the team, or the school. So our last year coaching together at Don Bosco was 1979.”

  In 2012, Skip and I met at a local pub in Waltham, Massachusetts. He reflected on bumping into Dempsey again in 1980.

  “I don’t think there was any player closer to Dempsey than me,” Skip said. “He took me under his wing and shaped me from being a boy to becoming a young man. My ability to attend college and play ball was all due to him. But then in 1980, I was back home in Brighton visiting my mother. One night, while I was at Sammy White’s bar with a group of friends, I saw Dempsey off in the distance. I stood up, waving, ‘Hey, Coach, how you doing?’ Dempsey quickly turned and looked at me as if he’d never known me. The look on his face was like ‘Don’t fuck with me.’ He never said a word. He just turned and walked away, and I’ve never forgotten the look on his face. I sat back down, bewildered, wondering, What the hell just happened?”

  Coach Currier explained what it was like to watch Dempsey zero in on someone. “Many times, I’d seen Dempsey enter a bar, pick out the biggest guy, and wait for the right moment. Dempsey would sit up at the bar and eye the guy throughout the evening while having a few drinks. Dempsey loathed muscle-heads who purposely wore overly tight shirts to try to impress the girls. Late into the evening, Dempsey would saunter up to the unexpected target, slap him on the back, and offer to buy the guy a drink. When the muscle-head scoffed at Dempsey and said, no thanks with a dismissive tone, Dempsey would turn it up a notch.

  “What’s the matter? Too good to have a drink with me? Come on: I said I want to buy you a drink.

  “After a second refusal, Dempsey would unleash on the poor son-of-a bitch. At times, Dempsey would simply punish people. It was truly something to watch,” Currier said, as I shuddered at the thought of seeing Dempsey beat someone to such an extent that they ended up needing
an ambulance.

  During Dempsey’s lifetime, he would find himself in front of a judge fourteen times. From 1963 to 1973, he was arrested nine times. Most were DUIs, one was for operating to endanger, and one was for assault and battery. But in 1978, his rap sheet would start to look different. That year, Dempsey was arrested for discharging a firearm and an assault with a dangerous weapon. Though the charges would eventually be dismissed, it was barely a year before Dempsey was arrested again for assault and battery with a dangerous weapon. Somehow, though, these charges were also dismissed.

  On July 1, 1981, however, Dempsey made a decision that would change his life forever.

  Edward White (not his real name) was big for twenty-four. A resident of Dedham, Massachusetts, he stood 6’3” and weighed close to two hundred and thirty pounds. White had been a regular at a bar called Mr. McNasty’s in downtown Boston. According to management, White was a good kid. He had never caused a problem at the bar and was viewed as quiet and friendly. Dempsey had just begun hanging out at McNasty’s after being introduced to the place by a new acquaintance, a taxi driver and part-time bouncer named Sawyer.

  Life can involve a series of complicated intersections and, for White and Dempsey, theirs would end up being catastrophic. To this day, no one can say for sure whether or not Dempsey and White had ever met prior to July 1st of that year. But that evening, Dempsey was with a small group of friends, drinking White Russians and working the room, socializing with his friends and with Meany, McNasty’s 6’6” bartender.

  When interviewed by police, Meany reported that, “Dempsey came up and introduced himself to me and, throughout the night, bought me a few beers. I couldn’t drink on the job, though, so I put the beers on ice to take home for later. Dempsey appeared clear-headed and calm throughout the night. I didn’t sense any hostility at all from him. If he was agitated, in a bad mood, or looking for trouble, it didn’t come across to me.”

  But waitress Allison Towne picked up a different vibe from Dempsey. “He called me a bitch for not smiling at him after he made a comment to me,” she said. “He wasn’t the typical Mr. McNasty’s customer. He made me feel uneasy.”

  What first lit the fuse between Dempsey and White, no one knows for sure, but a few words were tossed back and forth before someone eventually approached Sawyer to intervene.

  “Mr. Sawyer, please tell us exactly what happened when you first approached Mr. Dempsey,” Detective O’Halloran said, waving the cigarette smoke from his face while sitting at a private table in the back corner of McNasty’s.

  “I walked over to Dempsey,” Sawyer said, “placed my hand on his shoulder, and asked if everything was okay. Dempsey shrugged and said he was fine and that it was White who was having the problem. So I approached White and told him that Dempsey didn’t want any trouble and everything would be okay.”

  Having been a bouncer at the Hatter, and having worked crowd control at Fenway Park, I had broken up plenty of fights. On a scale of 1-10 (10 being the worst), White and Dempsey’s interaction to that point seemed like it should’ve been somewhere around a 2. But I had seen plenty of disputes escalate with devastating results, where people got knocked out, lost teeth, had their noses broken, were hit with pipes, bats, tire irons, and so forth, but those fights were usually triggered by an emotional outburst that turned red-hot real fast, much more intense than what was initially going on between Dempsey and White (at least according to witness accounts).

  Case in point: One Friday night when the Hatter was packed, four Boston College football players arrived. One of the players was Fred Smerles. Smerles stood 6’4” and was two hundred and eighty-five pounds of solid muscle. He was enormous! He was also an All-American defensive tackle who’d go on to have an NFL career with the Buffalo Bills at nose guard.

  Fights inside the Hatter didn’t last long, what with twenty-eight bouncers on duty, but on this particular night, Smerles and his teammates had a problem with a group of kids from Southie. After the first punch was thrown, the club exploded and, for the first time in my career there, we couldn’t shut the fight down. Over forty Southie kids swarmed over the BC players. After ten minutes, each of which felt like an eternity, we managed to regain control of the club. But five bouncers still had Smerles up against a wall.

  “Freddie,” pleaded Billy Bragger, one of our biggest bouncers, “just stay right here, please. Someone’s gonna get really hurt if you don’t stop.”

  “Okay, okay, we’ll leave,” Smerles said, relaxing and putting his hands down by his sides.

  Suddenly, though, a Southie kid ran up behind Bragger, jumped up, and threw a punch straight at Smerles’ face. Without looking or skipping a beat, the kid flew out the front door into the parking lot. Smerles snapped. He was so enraged that, as he chased the kid into the lot, I thought to myself, If he ever gets his hands on this kid, he’ll kill him. That level of anger made sense to an outside observer given the brawl’s build-up.

  But to the witnesses at McNasty’s, the interactions between Dempsey and White hadn’t come anywhere close to the Smerles incident. Dempsey and White’s comments were short and comparatively light. And, what’s more, a bouncer was there to intervene. So the million dollar question is: What made Dempsey, a man who could easily take care of himself in a fistfight, a man who was legendary for it, pull out a handgun so soon?

  It’s a mystery we may never find the answer to.

  But, no matter the reasons, around eleven-thirty that evening, someone heard Dempsey say to White: “You fucking asshole, you want to fuck with me now?”

  Witnesses then saw Dempsey holding a snub-nosed .38 caliber pistol just three feet away from White, who replied, “Put that puny thing away.”

  “I’m going to kill you, motherfucker.”

  Then Dempsey aimed the gun at the floor and pulled the trigger. The bullet hit the ground between White’s feet, causing him to jump back, but then, to everyone’s surprise, White turned around, bent over, and jeered, “Why don’t you stick it in my ass and pull the trigger?”

  For someone who’d just had a gun fired at them, this was a more than bizarre response, and one that only heightens suspicions that perhaps there was some prior connection between White and Dempsey.

  I’d once had a gun pulled on me back in 1987. I was line-striping a parking lot for a bank on Route 9 in Framingham. We could work only when the parking lots were empty, so we arrived no later than five in the morning to get started. The bank guard working inside the bank had no idea who we were, though, that first morning, and so he called the local police.

  It was obvious the cop who arrived had been sleeping while on his shift—his hair was a mess and his eyes were still adjusting to the lights in the parking lot as he squinted blearily at us. In fact, it was easy to tell he’d been in a lousy mood even before he climbed out of his cruiser, given how he came tearing into the lot. Screeching to a halt, he jumped out of his cruiser with his gun already drawn.

  “Hit the ground now, motherfuckers! Now!”

  Having a gun pointed at you, realizing your life could end in an instant, made the size of the gun increase tenfold. To me, that barrel looked to be the size of a howitzer. Scared shitless, I hit the ground just to get out of the line of fire.

  What enabled White to remain so relaxed after the gun was fired at him is mind-boggling.

  When White then turned around and laughed in Dempsey’s face, Dempsey fired one shot directly into White’s chest.

  White stepped back and looked at the bartender, and then at the bouncer. His expression was one of disbelief, as if he was thinking, Can you believe he just shot me?

  White took one step forward toward Dempsey. Dempsey fired a second shot into White. The kid spun quickly to his left, and that’s when Dempsey fired his third and final shot into White’s body. White stumbled backwards and collapsed near the front door.

  Dempsey stepped over White and, in a fit
of rage, took two swipes at him with his gun, missed, and then pushed White back into the floor. Someone moved quickly toward Dempsey’s right side, perhaps in an effort to wrestle the gun from him, but then Dempsey raised his weapon again and the man immediately stopped and threw up his hands.

  “Hey, no problem here!” the man said.

  Dempsey finished his drink, placed the empty glass on the counter, shook hands with the doorman, and told him he’d see him later.

  Patrons were stunned. As Sawyer later testified, “At first, I thought it was a joke.” Some people thought someone had lit firecrackers inside the club, which is actually fairly reasonable since it was so close to the Fourth of July. One witness thought White was dead before he hit the ground, but then two patrons (both with medical backgrounds) opened up his shirt, saw three holes in his chest, and said he was having trouble breathing. They yelled out for someone to call 911.

  White never said another word. He died on the way to the hospital.

  Dempsey, in the meantime, worked his way to another bar and had a few more drinks to calm himself down and try to make sense of what had just happened. He eventually made his way to a friend’s home in Stoughton, a small town outside of Boston, and stayed for a day or two. The shooting made the papers and the local television news. Dempsey then headed for Maine and stayed with his lifelong friend, Mike Kelly, who was there on vacation with his family.

  Dempsey told Mike Kelly that he’d had a bad beef in Boston and needed to stay out of the city for a while. Kelly testified that he never asked for any specifics, and that Dempsey never gave them. After a few days, Kelly told Dempsey that he might want to leave the states entirely if he was really in that much trouble. So Dempsey called a friend for some money and jumped on a bus to Canada with twenty-eight hundred dollars, a stolen Vermont driver’s license, and a loaded gun. Dempsey eventually made his way to Toronto and stayed in a few halfway houses, quickly realizing that he needed to establish a new identity.