by Howie Carr
No matter how incorrigible, any prisoner was eligible, as Jimmy Flemmi discovered one Friday in 1976 when he was released from MCI-Norfolk for a weekend on the town. The Bear immediately took off for Boston, to settle some old scores, starting with his ex-wife.
Fortunately for Mrs. Flemmi, she wasn’t in her Hyde Park home when the Bear arrived, so he settled for strangling her cat and tearing the place apart. Then he vanished, not to be seen again for three years. This time, Jimmy Martorano wouldn’t get arrested for helping the fugitive Jimmy the Bear. Like everyone else, he now knew enough to steer clear of the Bear.
But even though Jimmy Martorano didn’t know it yet, he had another problem. The FBI was lining him up. They’d done a lot for the Hill, and now it was time to claim a scalp.
My brother was doing a little shylocking, not much, but some. He knows this guy who loaned $2,000 to his own brother, who ran a bar in Revere. Now this guy figures out his brother will never pay him back, so he asks Jimmy if he can say he got the money from Jimmy Martorano. That way maybe his deadbeat brother will get scared and pay it back.
In other words, it was a favor. Well, of course the brother still doesn’t pay it back, so the guy asks Jimmy if he can send somebody over to the bar to scare his brother. Jimmy didn’t want to get involved—what does he care about this one way or the other? But Brian Halloran heard the story and he decided to go up to Revere on his own. As usual, he’s drunk, and he pulls a gun on the bar owner and steals $445 out of the register. The bar owner runs to the FBI, and John Morris takes over the case and they arrest Halloran and my brother.
Still, Jimmy Martorano wasn’t that worried. If he was needed, his friend said he would be willing to testify he hadn’t borrowed any money from Jimmy. That way, Jimmy and Brian Halloran might be facing state robbery or assault charges, but not a serious federal rap like extortion. In a Suffolk County courtroom, at worst they’d be looking at months, not years.
One morning, at the garage, Jimmy mentioned he was going into the city to confer with his attorneys. Whitey and Stevie asked if they could tag along and Jimmy said sure. They overheard the entire discussion of Jimmy Martorano’s defense—including the name of his surprise witness.
The next morning, agents Morris and Connolly barged into the home of the guy who was to be Jimmy Martorano’s defense witness. Panicking, he ad-libbed a different story where the $2,000 had come from. He said he got it from his wife. He mentioned nothing about asking for a favor from Jimmy Martorano.
So Jimmy’s witness was out. If he told his original story under oath, Zip and Morris would be sworn as witnesses to impeach his credibility. A few months later, in June 1976, Jimmy Martorano was convicted on the federal charges. Halloran inexplicably beat the rap, although by that time he was already in prison on weapons charges.
Nobody ever put two-and-two together until everybody was in jail together years later in the late ’90s. As part of discovery, the feds gave everybody an FBI letter of commendation to Zip for getting one conviction of a so-called major Winter Hill figure in 1976. Well, there was only one conviction of anyone that year—my brother, Jimmy.
I was gone by then, but after they saw the document, somebody asked Stevie, why’d you rat out Jimmy Martorano over nothing, just to allow your pal Zip to win a few Brownie points with his bosses in Washington?
You know what Stevie said? He said, “Somebody had to go, and Jimmy did good time.”
9
The Bubble Bursts
LAWYER: You weren’t afraid to punch somebody, right?
MARTORANO: Not if it was called for.
EVERYTHING STARTED TO go wrong for the Winter Hill Gang in 1976. For three years or so, ever since Tony Ciulla had started fixing horse races, they’d been in an economic bubble—their assets rising wildly, out of all proportion to reality. They were making money here, there, and everywhere. The local cops were their friends, they had total protection in Somerville, they owned an FBI agent, they were getting along with the Mafia—what could possibly go wrong?
Like all bubbles, though, this one would end badly, in ways that no one in the gang could have ever imagined.
Johnny was in charge of keeping the sports gambling books. His partners didn’t like bad news, especially during football season. With an open line of credit from Jack Mace, they bet heavily. Their long-distance phone bills were astronomical. They were always calling Vegas, looking for an edge. One of the race-fixing guys out there was an old Boston hand named Mel Goldenberg. He had a handicapper known as “White-Haired Jack from Pittsburgh.” Another guy they used was Bob Martin. He was supposed to be bigger than Lefty Rosenthal, the Vegas gambler Robert DeNiro played in Casino.
Sometimes their guys in Vegas came up with good information, and the gang collected. Sometimes.
I’d go to the garage every Monday morning, and they’d all be staring at me as I walked in. They didn’t want to know, did we win this weekend? They wanted to know, how much did we win this weekend? That’s the way they thought. You gotta remember, we weren’t six Einsteins, we were six shylocks, gamblers, bank robbers—you know what I mean. Regular guys.
One thing that was always strange to me was how little Whitey knew about sports. It’s one thing not to care about watching the games on TV, which neither he nor Stevie did. But they didn’t even know what a double play was in baseball. And Whitey had no understanding of odds. I could never figure out why he wanted to get into sports gambling in the first place when he didn’t understand odds. Sometimes on Fridays, Whitey would ask me, who are we rooting for this weekend? And I’d say, the Patriots. And Monday morning I’d come into the garage and he’d say, all right, the Patriots won, I saw it in the paper. So we won, right? And I’d have to explain it to him, Well no, we didn’t win, because the Patriots were six-point favorites, and they only won by three, so we lost. But he never got it, no matter how many times I explained it to him.
It was practically un-American how little he knew about sports. I even called him un-American to his face a couple of times. He just laughed.
Anyway, how the money worked was, if we took a big hit, we’d just borrow money from ourselves. I could always get cash from Joe McDonald—he handled the money for the “old” Winter Hill Gang, which was him, Howie, and Sims. At the end the new Hill owed the old Hill a half million. I borrowed 200 grand from myself, Whitey threw in 60, Stevie 20, and of course eventually we owed Jerry Angiulo $250,000. It didn’t seem like such a big problem because when I lent the Hill 200 grand, I was paying myself a point a week vig—two grand. That’s a lot better than you can get in a bank, right?
But the reality was, every week I had to come up with over ten grand just to pay the vig to everybody. Five grand to old Winter Hill, which I mainly gave to Howie Winter Jr., $2,500 to Jerry Angiulo, $2,000 to myself, $600 to Whitey, $200 to Stevie, and another grand or so to various other guys.
But remember, we didn’t lose every week. A lot of weeks, we came out ahead—way ahead. So I’d come into the garage Monday and say, okay, we’re up a hundred grand this weekend. Now, what do we want to do, do we pay down the balance on what we owe, or do we just whack up the 100 grand right now? You can guess what the vote was.
Then Tony Ciulla got arrested. The first one to go down was one of his jockeys, a guy in New Jersey. At Suffolk Downs, the jockeys might have stood up, especially the ones who’d been slapped around. But in New Jersey, names like Barnoski and McDonald didn’t inspire quite the same respect as they did on their home turf.
The jockey gave up Ciulla, and he was arrested on a parole violation. Everyone knew it was only a question of when, not if, he’d flip. At the garage, Johnny didn’t even have to state the obvious, that he had told them so—that they should have whacked Ciulla when they had the chance, not Sousa. Now there was going to be trouble. The only question was, how much.
* * *
JOE MCDONALD and Jimmy Sims had more immediate concerns. Like all the other partners, they had always continued operating their
own separate rackets, one of which was robbing coin and rare-stamp dealers. In 1974, police in California found a stamp dealer they’d held up who was willing to testify against them. Joe Mac and Sims took off for California, where Joe Mac once again barged into a home and gunned down the witness, whose name was Raymond Lundgren.
“Jimmy Sims told me about it later,” Martorano recalled. “He said, that Joe is one crazy bastard the way he just keeps walking into somebody’s house in a strange town with a gun in his hand.”
The FBI was drawn into the robbery case because McDonald and Sims had moved the stolen stamps across state lines. On April 1, 1976, the FBI put Joe McDonald on the Ten Most Wanted List—for interstate transportation of stolen goods, but not murder. It didn’t seem like such a big deal at first. Joe Mac went on the lam—to Chelsea.
One reason they weren’t concerned was because they had grown to rely on their own personal FBI agent, John Connolly, as a literal Johnny on the spot. Whitey and Stevie were giving him information in return, but everybody assumed it was routine stuff. What they didn’t know was that Whitey was handing the feds all kinds of dirt on every underworld figure in Southie who wasn’t on the Bulger team. As one of the Hill’s lawyers put it later, “With the Italians, Stevie was mainly providing gossip—so-and-so’s going to a wedding, or somebody was opening a restaurant on Hanover Street. With the Irish from Southie, Whitey was giving Zip addresses, telephone numbers, license plate numbers. He was already letting the FBI do his dirty work for him, weeding out the competition.”
All we knew was that Zip was taking care of us, indirectly, because of Whitey. We told Whitey, anytime you have the opportunity to do something for him, whatever it is—cash, airline tickets, anything—you tell us and we’ll get it for him.
So Whitey comes to the garage one day and tells us, Zip wants to give his wife a ring. Now, I know Joe’s got some stolen jewelry, so I went to see him in Chelsea and I picked out a nice diamond ring—two carats. I paid him two grand, out of the kitty, but the stone itself was probably worth 6 or 8 grand. The only problem was, it was in a man’s setting, but Whitey took it to a jeweler and got it reset. Zip was pretty happy. I figured it was the least we could do. I mean, when Howie and I went to see Schneiderhan, I always brought an envelope with at least $1,000 in it. I’d just leave it there for him, no name on the envelope or anything. I didn’t want to embarrass him.
Jimmy Martorano had always managed Chandler’s, and after his conviction nobody else in the gang had any interest in actually running the place. It was too much like work. There was only one thing to do, the same thing they always did when they got tired of operating a business. They torched it.
The Boston police organized-crime unit and the fire department’s arson squad quickly began investigations.
As usual, nothing came of the probes, and the Hill collected on the insurance. The money came in handy. Not only had they lost the income from Ciulla’s race fixing, now they had to support Joe Mac and Jimmy Sims on the lam. And Zip Connolly notwithstanding, some of his fellow feds were actually looking for Joe and Jimmy. The Hill had to get them out of town, and they did, in the fall of 1976.
I went down to New York to see Jack Mace, Castucci’s friend, the guy we were betting with. He had an apartment in the Village, Washington Square. I gave him $14,000 cash for a year’s rent, including utilities, telephone, everything, so Joe and Jimmy didn’t have to put their names on anything. I didn’t tell him who I was putting in there, but I did tell him, don’t tell anybody about this. Nobody.
But Jack Mace did. He told his associate in Boston, Richie Castucci, and Castucci put two-and-two together. Joe McDonald and Jimmy Sims had to be the guys in New York. And then Castucci told the FBI. He, too, was an informant. Castucci had been recruited back in 1969 at the Howard Johnson’s in Revere, when Boston FBI agents told him that his wife had been involved in an affair with Mafia soldier Salvatore “Mike” Caruana, who would become a major drug trafficker before vanishing in the early 1980s.
In a later lawsuit against the U.S. government, Castucci’s widow would deny the affair. But according to a 1970 FBI report, Castucci had thanked the G-men for telling him that Caruana “stole his wife. He stated that if he was a guy who carried a ‘piece,’ or was violent, he would kill Caruana for doing this.”
Six years later, Castucci found himself in a precarious situation. He was with the Hill, he was with In Town, and he was with Mace, who was connected to the Gambino crime family in New York, although no one in Somerville knew that yet. Castucci had put Mace and the Hill together, and now the Winter Hill Gang was betting thousands of dollars a week with Mace. Sometimes Johnny would send down a doorman from the old Chandler’s to settle up with Mace at LaGuardia Airport. Depending on the weekend’s outcome, the doorman would either deliver or pick up a bag of cash. If the doorman wasn’t around, sometimes Castucci would make the pickup or delivery at the garage.
The problem for Castucci was that his handlers in the Boston FBI office trusted Zip Connolly. Why shouldn’t other agents know who their fellow feds were talking to? After all, if you couldn’t trust a brother agent, who could you trust? And this wasn’t exactly a shoplifter they were hunting—Joe McDonald was a Ten Most Wanted fugitive.
So the other agents in the office tell Connolly what Castucci came up with, and Connolly tells Whitey. Whitey comes to the garage and tells us that Castucci is a rat, and he’s told the FBI where Joe Mac and Sims are. I think my first words when I heard it were, “That motherfucker!” I never liked the guy to begin with. He was a swindler, a past-poster, a card cheat, just no fucking good. But I didn’t figure him for a rat.
Still, it’s pretty easy to figure out what happened. Mace is just talking out of school—he’s not a rat, not on this anyway, although we found out later, he was in fact an informant for the feds down in New York. So he mentions it to Castucci, not knowing the significance of what he’s telling him, and Castucci, that motherfucker, he runs right to the feds with it.
There was only one way to settle up with Castucci now. Later, it was suggested that Castucci was killed because the Hill owed Mace $150,000, but just a few weeks earlier, Johnny had sent his guy down to LaGuardia with some money that the Hill owed him. Altogether, Mace had already collected $400,000 from Winter Hill.
Castucci rocketed to the top of the Hit Parade because he had ratted out Joe McDonald and Jimmy Sims. Still, at the garage, the thought did occur to everyone, why pay any more money to a guy who’s about to get hit in the head? Being a rat cancels a debt—that was one of the Hill’s rules to live by. And to die by.
* * *
THE FIRST thing Johnny did was call the apartment in the Village and tell Joe and Jimmy to clear out. He’d fill them in on the details later, but the most important thing was to get out of New York. And Johnny mentioned one other thing to them, that Whitey had insisted upon. Johnny told them to never, ever tell anyone that they got a heads-up to leave. If anyone asks, he said, just say you had a feeling. Zip was already starting to sweat this one. This tip was worth more than a diamond ring, a whole lot more.
* * *
IT WAS December 30, 1976, cold and snowy in Somerville. Johnny called Castucci in Revere and told him he was a little short from the holidays but wanted to get Jack Mace at least $60,000. His guy wasn’t around to make the flight to New York, Johnny said, so would Richie mind coming over to the garage to pick it up?
Johnny had the money in small bills, so Castucci would have to count it. He told Castucci that Whitey would take him down to the Pad—the gang’s apartment—and that he could take as long as he wanted to count it.
Once inside the Pad, Whitey got Castucci seated just inside the front door at a round table, with his back to the door. Whitey was facing the door on the other side of the table, directly across from Castucci. Johnny waited a couple of minutes, until Castucci got settled in and started counting the bills. Then Martorano walked in with a gun, the usual .38-caliber snub nose revolver, approaching Ca
stucci from the side. Johnny put the gun right up to his forehead and pulled the trigger. Castucci never knew what hit him. There were no last words.
When Johnny fired, across the table Whitey flinched. Next Stevie arrived, and he and Whitey began the cleanup. Joe McDonald’s brother, Leo McDonald, then showed up. Johnny told him to go down to K-Mart and buy a sleeping bag to wrap the body in—the same duty he’d had after the Sousa murder two years earlier. A half hour later Leo returned with a cheap Walt Disney sleeping bag covered with pictures of Snow White and the Seven Dwarfs. It cost maybe six dollars.
Leo McDonald, Joe’s older brother, a Hill associate.
“You can pay me later,” Leo told Johnny, and Johnny smiled and nodded. He’d just killed a guy for Joe Mac, and now he owed his brother Leo six bucks.
They waited until it got dark, which wasn’t long on one of the shortest days of the year. Then they lugged Castucci’s body out to his Cadillac and put it in the trunk. Wearing gloves, Johnny drove Castucci’s car back to Revere, with Leo behind Johnny in his own car. Johnny dropped the Caddy off in some parking lot over by the water and then he and Leo drove back to the garage.
The cops found Castucci’s body in the trunk a couple of hours later.
Richie Castucci’s body in the trunk of his Cadillac after his murder by Johnny in 1976.
* * *
THERE WAS hell to pay at the JFK Federal Office Building. The FBI couldn’t allow its informants to get whacked. It was bad enough that Castucci had been outted, let alone killed. Even though it was a holiday week, an interagency meeting was immediately convened of all the various federal law-enforcement agencies—FBI, Justice Department, DEA, Customs, Secret Service. Zip Connolly was among the attendees.
One after another, everyone was asked: Who could have done this? Where was the leak? Finally they got around to Zip Connolly. Zip spoke slowly, for emphasis. Already a lot of the other feds looked up to him, for his success in recruiting such high-level informants. Zip explained how he’d been working his sources. He said they’d told him that Castucci had owed the Mafia a lot of money, and In Town didn’t like that he was planning to pay off his debts to the Hill first. Now he was dead and the Hill was out a lot of money. So obviously they had no reason to kill Castucci. Good old Zip, always taking care of “his Irish,” as he called them, even while he was simultaneously trying to save his own hide as well.