“Welcome to the brotherhood. You’re gonna go far.”
My previous top-secret deliveries were warm-ups for what came next.
In November of 1971, Mr. Alex began sending me on what he reverently called “the confidential runs.” It was an assignment for only the most trusted and loyal of employees, he told me.
Mr. Alex was looking to expand his liquor delivery to include a Montreal-to-Boston route, and there was only one way to get that. He had to pay a kickback to the guy who was already leaning on the local distributors there—that guy was Boston crime boss James “Whitey” Bulger.
At that point the Irish Bulger, 42, wasn’t a crime boss yet. He’d done time at Alcatraz and was a top lieutenant to mobster Howie Winter, the leader of the Winter Hill Gang—the top Irish Mob syndicate on the East Coast. Seven years later he’d be boss of that gang and kill his way onto the FBI’s “Ten Most Wanted List” for his role in nineteen murders. He was a cunning, charismatic, “hands-on” killer—the kind of guy who’d shoot your testicles off and enjoy watching you slowly die as blood poured out from where your balls used to be.
In 1971, all I knew was that Whitey was the guy we had to pay off if we wanted our trucks to make a stop in Boston. If we even wanted to pass through Boston without paying Whitey, he’d steal our loads.
I arrived at the office in early November to find Mr. Blumenblatt, Mr. Alex’s VP, waiting for me. Mr. Alex was the boss, but Mr. Blumenblatt was the brains. He wore old fedoras from the forties and underneath them his mind worked overtime. Mr. Blumenblatt did everything for Mr. Alex, including sucking his ass. If Mr. Alex stopped short, Mr. Blumenblatt’s face slammed into his butt.
When I arrived that morning, Mr. Blumenblatt handed me the usual briefcase—a black, beat-up Samsonite with a combination lock. These were leftover, used suitcases the salesmen at Maislin had worn out and tossed. This time, Mr. Blumenblatt also gave me a piece of paper with an address scribbled on it, a wad of petty cash, and a plane ticket on Allegheny Airlines.
“You’re flying to Boston this morning,” he said. “The briefcase goes to Mr. Bulger. We gotta take care of him.”
Just like Hoffa, the name meant nothing to me. Mr. Blumenblatt proceeded to give me specific hand-off instructions.
“Tommy, when you give it to Mr. Bulger . . . hand it to him low.”
“Low?”
“Yeah. Under the table like, so nobody sees.”
A few hours later I was landing in Boston with a briefcase full of $125,000 in cash on my lap. That was the beauty of the seventies—no security opening your bags, no X-ray machines to worry about.
I took a cab to Triple O’s Lounge in South Boston, where Mr. Bulger was waiting for me at the back. The place looked dark and sticky, and it smelled of spilled beer and stale cigarette smoke.
I didn’t need anyone to tell me which one he was. First of all, the joint was empty because it was strictly used for the gangsters and their crew. Second, Whitey’s whole demeanor had boss written all over him. After I was frisked at the door, I was escorted past the pool table and dance floor to Mr. Bulger, who stood up to shake my hand. He had a guy sitting with him. Guys like him always had a guy sitting with them.
The first thing I noticed were his wrists—they were as thick as tree trunks. They were the kind of wrists that were connected to the kind of hands that killed people.
“Ha ya doin’, kid?” he said, in an elongated Boston accent, and smiled.
“I do just fine, Mr. Bulger.”
I handed the briefcase to him low, as instructed, and he put it under the table.
“You did good. Thank you. You hungry? Djeet? ” (Translation: Did you eat?)
On the table was every antipasto and pasta on the menu.
“No thank you, Mr. Bulger. I’m good.”
The entire exchange lasted less than five minutes and then I was out the door, on my way back to the airport.
That was my routine with Whitey every four to six weeks. We didn’t say much more than that, and I never sat down when he asked Djeet?
On a snowy day in February 1972, I was given a new confidential run. Mr. Alex told me the assignment himself; it was that important.
“We have a VP coming in from Detroit,” he said. “You’re going to the airport to pick him up; he’s coming in on the Blue Goose. His name is Jimmy Hoffa.”
I still had no idea who he was. (“Tommy, you’re green apples,” Mr. Alex used to say, when I didn’t know these guys. “You ain’t ripe yet.”)
Six weeks earlier, Teamsters Union leader Hoffa, 59, was sprung from a Pennsylvania prison after serving less than five years of a thirteen-year sentence for attempted bribery and fraud. Richard Nixon himself pardoned Hoffa—after the union leader allegedly bribed him. Also part of Hoffa’s sweet deal with his pardon was a one-time lump sum of $1.7 million for a pension—a first of its kind in Teamsters’ history.
A few weeks before I was sent to pick up Hoffa, Nixon announced his candidacy for reelection. The International Brotherhood of Teamsters would endorse Nixon for a second term as president later that year, of course.
Mr. Alex tossed me the keys to his Cadillac.
“Take my car. At the airport, hold up a piece of paper that says ‘Hoffa.’ I told him you’re a scrawny kid wearing a baseball cap and he’ll come to you. Go pick up this motherfucker and bring him back here. And Tommy . . . for god’s sake, drive slow.”
I wasn’t sure if he was worried about Mr. Hoffa or his car.
At the arrivals gate I held up my scribbled sign and two men approached me. One had dark slicked-back hair and the face of a bulldog. The other guy was one of those guys who was always with the important guy.
“Are you the driver?” the bulldog-faced one asked. I nodded.
“I’m Jimmy Hoffa.” He stuck out his hand. “How you doin’?”
“I do good, Mr. Hoffa, real good.”
“No, no. You call me Jimmy.”
“All right, Mr. Hoffa. Here, let me carry your bags.”
“No,” said Hoffa, “we carry our own bags. Just take us to the car.”
I had parked illegally outside the front doors, but I knew the cops circling the airport would recognize Mr. Alex’s XXX plates and protect the car. The drive back to the office was quiet, uneventful, and slow—at Mr. Alex’s orders. When Hoffa’s meeting with Mr. Alex was over a few hours later and I took him back to the airport, he was talkative.
“In prison they built a special cell just for me,” he told me, “with accommodations to my liking.”
Talk in the back seat shifted to the Kennedys. In the fifties, Bobby Kennedy worked for years investigating labor racketeering and tried to nail Hoffa then, but he couldn’t. After John Kennedy was elected in 1960, Bobby continued his crusade as attorney general and put together a “Get Hoffa” squad of prosecutors and investigators in the Justice Department to get him behind bars, which they finally did. John Kennedy was assassinated four months before Hoffa was sentenced, and Bobby Kennedy was assassinated while Hoffa was in prison.
“Slimy pricks set me up,” he was saying to the other guy.
At Newark Airport, I hopped out of the car and opened the door for him. Before he left, he shook my hand again.
“Tommy, how long you been in trucking?”
“Just a few months, Mr. Hoffa. I graduated high school last year.”
“Ah, a real working man, I see. Well let me tell you something. They love you at Maislin, kid. You’re smart and fast; I can see that and so can Alex Maislin. We talked about you. You’re going to have a big career in the trucking business, lemme tell you. Welcome to the brotherhood. You’re gonna go far.”
“That’s beautiful, Mr. Hoffa.”
And just like that, standing in front of the Blue Goose entranceway at Newark Airport, the powerful and corrupt union leader predicted my future and solidified a new fate for me.
When I got back to the office, Mr. Alex and Mr. Blumenblatt were giddy drunk on whisky, and Mr. Alex hugged me.
“Hoffa loved you!” said Mr. Alex. “Did he tell you we’re going to send you to the Academy of Advanced Traffic? It’s a private school, very expensive. His idea. We’re going to take you under our wing and you’re going to learn everything there is to know about trucking. We’re going to groom you to be an executive here.”
“Oh, that’s beautiful, Mr. Alex!”
Hoffa liked me so much that we added him to my out-of-town confidential runs every four to six weeks, just like Whitey.
Why was Hoffa getting a briefcase full of cash if we were already paying various union presidents? Because Hoffa was more powerful than the president of the United States.
Every two weeks, I was either flying to see Whitey or Hoffa. I never knew who or when. I’d find out when I arrived at work that day and Mr. Blumenblatt or Mr. Alex handed me a plane ticket.
I’d meet Hoffa in Detroit at a restaurant called Machus Red Fox in Bloomfield Hills. It smelled like an old-fashioned gin mill. He always sat in the back, like Whitey, with his back to the wall, and he had a guy with him.
Like with Whitey, I’d hand the case to Hoffa low, and our entire exchange would only last a few minutes and I’d be on my way back to the airport.
“You’re doing great, Tommy,” he’d say each time, then added, “You’re going to be a big success. Djeet?”
Sometimes Hoffa would say, “Do the right thing, Tommy.” That meant: Take care of yourself, take care of me, take care of Mr. Alex, keep your mouth shut, and most of all—don’t fuck up.
When winter weather was bad, the handoff happened at the Detroit airport without Hoffa—he’d send his bodyguard, a short guy with a big gun, to meet me at my gate. We’d walk to a coffee shop and do the handoff there. A few minutes later, I’d be back on a plane to Jersey.
Delivering money to Whitey and Hoffa, I never had a real concept of the danger I was putting myself in. I look back now and know I could have been robbed or beat up or worse. To me, it was just part of my job. I didn’t know enough to be scared or overly in awe of these guys. I still didn’t have a full understanding of what the world of organized crime was until a month after my first meeting with Hoffa, when The Godfather was released in movie theaters.
Debbie and I went to see it and I couldn’t take my eyes off the screen. The Cadillacs, the suitcases filled with money, the guys beaten up by the docks, the guns, the corrupt union bosses. I’d seen it all, but in real life.
“Holy shit,” I whispered, under my breath. I went to see the film three more times, alone. I was thrilled by the danger, riveted by the power, and mesmerized by the money. Being a small part of something so big, so feared, and so notorious made me feel strong. I couldn’t wait to get my own black Cadillac.
Mr. Alex was true to his word about grooming me. During the spring and summer of 1972, he put me in different departments at the office for weeks at a time to learn about over-shortages and damages, customer service pickup, dispatch, sales coordination, receivables, payables, accounting, and mergers and acquisitions.
In the sales department, Mr. Blumenblatt watched me charm potential clients on the phone while aggressively pitching them, and he reported back to Mr. Alex.
“I hear you’re a natural-born salesman, Tommy,” said Mr. Alex. “I have good news. I’m going to groom you to take over the New Jersey division.”
I told this to my mother when I got home from work that day, and for the first time in my life she said, “I’m so proud of you, Tommy. The way you’ve changed.” She made sure to say it in front of my father just to scootch him. He didn’t say anything.
That weekend, I went next door to see Charlie. I’d ignored him all year but now I was feeling so good about how I was doing, I wanted to tell him. And maybe, I wanted to brag and rub it in his face a little—no, a lot. I was making money, and I was in school and wasn’t stealing and I had a big future in trucking—Mr. Alex and Mr. Hoffa said so! I wasn’t on the bad path he predicted for me.
When I approached Charlie on his driveway, this time he was the one who walked away from me. Motherfucker, I thought. I was hurt, and that made me angry. I’ll show him.
But I never did.
A few months later, Charlie died of a sudden heart attack. I refused to go to his funeral and I would feel a lot of regret about that later—but not just yet.
My mind was elsewhere. It was with the dangerous, enticing world I’d seen on the movie screen. In that moment, I felt like Michael Corleone in The Godfather when he realizes that this world is in his blood.
I belonged to a new crew, a new kind of family, and that was my world now. I was a teenager associated with some of the most powerful Mafia associates in the country. My mother was proud of me for turning my life around and being a good boy, but I knew the truth about that.
By the end of 1972 Nixon had been reelected in a landslide victory months after the Watergate break-in, and he was all over the news. It would be a while before we’d hear about slush funds and Deep Throat and bribes, but when I looked at his face and into his eyes on our old black-and-white, I saw the crook that he was.
I knew one when I saw one, because I looked at one in the mirror every morning. Even though I’d been good all year at Maislin, the thieving con artist in me was like a dormant monster, waiting to take over.
It would again, soon enough. Not just yet, but soon.
Like the stench of the dump, it was in me for good.