Hitman

by Howie Carr

  Whitey’s other idea was that they would offer to back bookies who wanted to get into betting on football. Long-term, that turned out to be the Hill’s biggest mistake. In the numbers racket, everything was fairly predictable, especially if you could control the daily winner by manipulating the handle at the track—usually Suffolk Downs—that was used to establish the daily number. But Whitey and the others were novices at sports betting. They failed to take into account that if you hit a bad patch in sports gambling, even the bank—the gang—was going to be hemorrhaging such large amounts of cash that they, too, would have to go to bigger shylocks, and in Boston that meant Jerry Angiulo.

  The way we considered it was, think about two people—one is a bookmaker you know and the other is a gambler you know. Guaranteed, the bookmaker is going to be living in a better house than the gambler. Because long-term the odds are on his side. As long as a bookmaker is patient and has enough money to ride out a bad stretch, in the end he wins. Bookmakers got no big edge in any one particular game. If you’re a gambler, you can win anytime. You can hit a streak and keep winning for weeks. But in the end, greed takes over and you lose. It happens every time. What’s the old saying? “All horseplayers die broke.” It’s so true, and it applies to sports bettors, too.

  In the beginning, the Hill had visions of going around to their bookies every week—guys like Dick O’Brien on the South Shore, Tommy Ryan in Cambridge, and Charlie Raso on the near North Shore—and cutting up huge pots of cash, 10 grand here, 20 grand there. They’d be rolling in dough, and with any luck, they wouldn’t have to risk shooting anybody.

  Now they just had to close the deal with Jerry Angiulo.

  Meeting as usual at the Dog House on Prince Street, Angiulo and the new gang leaders, Howie and Johnny, quickly hammered out an agreement. From now on, all bookmakers had to be connected with either In Town or the Hill. In other words, it was open season on independent bookmakers. Angiulo knew he couldn’t control every bookie anyway, and this way, he was partnering up with a group that might otherwise cause him problems down the road. The likelihood of an eventual war would be greatly diminished if everybody was making money, working together, more or less.

  But before they left, Angiulo gave his two new, younger partners some prescient advice: “If you get into betting on games, make sure you got a barrel of money, ’cause you’re gonna need it.”

  Jerry had it figured out a lot better than we did. He was financing bookies; all he cared about was one point a week on the money they owed him, the interest—the vig, as it’s called. He would back a guy who backed sports. Guy loses his shirt and has to borrow a hundred grand from Jerry, it’s a point a week—a grand a week, forever. Jerry wasn’t into sports gambling, he was into shylocking.

  Just as Howie and Johnny weren’t paying close enough attention when Angiulo mentioned that barrel of money they’d be needing, they likewise ignored the other tip Angiulo offered them, about a guy he’d heard had been hanging out at Chandler’s lately.

  “Stay the fuck away from Tony Ciulla,” the underboss of Boston said, not as a threat but as friendly advice, from one businessman to another. “He’s no fuckin’ good.”

  Later on, they couldn’t say they hadn’t been warned.

  * * *

  CHANDLER’S BECAME a hot spot, mentioned in the city’s gossip columns. When the 1973 gangster movie The Friends of Eddie Coyle was being filmed in Boston, actor Robert Mitchum hung out there nightly, along with his driver from Local 25, Fat Harry Johnson. As someone who’d done time himself almost thirty years earlier on a trumped-up marijuana charge in Hollywood, Mitchum fit in well with the Chandler’s crew.

  Also in the cast, both in the movie and at Chandler’s, was Bobo Petricone, Buddy McLean’s old pal who’d moved to Hollywood, changed his name to Alex Rocco, and become an actor. With his role in The Godfather behind him, Bobo was now back in his hometown, playing a bank-robbing gangster who bought guns from Mitchum’s title character.

  Mitchum was a John Wayne type, a two-fisted drinking cowboy. Howie and I are having dinner with him one night in Chandler’s and some cops come in and serve both of us with subpoenas for the grand jury. Howie is real embarrassed, and he apologizes to Mitchum, and Mitchum just laughs and says, “I’m just glad they didn’t serve me.”

  Fat Harry Johnson, Mitchum’s driver during the making of Eddie Coyle.

  Another guy from the movie who was in Chandler’s all the time was Peter Yates, the director. You know that scene at the end of the movie when they take Mitchum to the Bruins game and get him drunk, and then Peter Boyle shoots him in the head from the backseat? Before they shot it, Yates asked Howie for his … insight, I guess you’d say. Scene turned out pretty well, don’t you think? Very realistic.

  In addition to the nightly socializing, a lot of business was conducted out of Chandler’s. As Jerry Angiulo had heard, one guy who had started hanging around was a local swindler and degenerate gambler named Fat Tony Ciulla. A few years earlier, he’d tried to run a past-posting scam on a Mafia bookie—that was how Angiulo had gotten to know, and intensely dislike, Ciulla.

  Fat Tony was always working on a new grift. One of his more successful flimflams involved a large diamond pinkie ring that he always carried with him in a velvet-lined box from the high-end jeweler Shreve Crump & Lowe. Whenever he found a suitable mark, Fat Tony would offer to sell him his prized possession. To show what a trusting soul he was, Fat Tony would hand the Shreve box to the mark and tell him, take it to a jeweler, get it appraised, and then bring it back to me.

  Fat Tony Ciulla, the race fixer who eventually went into the Witness Protection Program.

  The mark would quickly find out the stone was genuine, worth maybe $30,000. He’d bring the box back to Fat Tony, who’d quickly stick it back in his pocket. After much negotiation, they’d finally agree on a very reasonable price and then Fat Tony would give the mark back the ring—except, of course, it wasn’t the same ring. It was in an identical box from the same store, and the stone was in the exact same gold-plated setting. But instead of a diamond, the mark would have bought himself a zircon.

  Whatever money Fat Tony could steal, he blew at the track. He had to place all his bets at the track, because bookies refused to take any action from him. Fat Tony was a pariah. On the first night that he had appeared in Chandler’s in 1972, it was to settle a betting debt with one of Howie’s top bookies in Somerville, Bobby Gallinaro. Fat Tony’s brother-in-law, Eddie Ardolino, was a friend of Johnny’s from the old days at Basin Street. So Martorano asked Ardolino to bring his wayward in-law around to Chandler’s to settle up his debt to Bobby G.

  Bobby Gallinaro, “Bobby G,” a Somerville bookie and associate of Howie Winter.

  As Howie and Johnny sat at a table, Eddie Ardolino appeared in the doorway of Chandler’s. Behind him stood a hulking, unshaven, shabbily dressed man. He was six feet five inches and had to weigh at least 300 pounds. It was Fat Tony Ciulla. He was only twenty-eight years old, but he looked decades older. They walked over to the table and Fat Tony pressed a bulging letter-size envelope into Ardolino’s hand. Ardolino then handed the envelope to Howie as Fat Tony bowed his head, to avoid making eye contact.

  “There’s $2,000 in there,” Eddie Ardolino told Howie. “That’s all he’s got and he borrowed this from his mother.” He shook his head. “I’m telling you, Howie, don’t ever do nothing with this guy. He’s a big piece of shit.”

  Within a couple of weeks, though, Howie was often huddling in a back booth with Fat Tony. Like Ciulla, Howie loved the horses, and both owned a few. Tony had been fixing races, or at least trying to, ever since he was a kid. He’d done time for race fixing in Rhode Island, and he’d also been arrested at least once at Suffolk Downs. But now he claimed to have worked out a system. Johnny was wary; he trusted the judgment of both Jerry Angiulo and Eddie Ardolino. But they all needed money.

  Eddie Ardolino, Ciulla’s brother-in-law, who warned Howie Winter against doing business with Fat T
ony.

  * * *

  JOHNNY MIGHT be hanging out in a slightly more upscale neighborhood now, but sometimes he had to deal with an issue from out of the past—like Nelson Padron, the Roxbury drug dealer he’d pistol-whipped at Slade’s for the Campbells.

  In February 1973, when Padron was about to go away on an income-tax-evasion rap, he got into his head that he was going to settle a few old scores before he left, starting with Johnny Martorano.

  One Saturday night, a woman Martorano knew came running into Chandler’s and told Johnny that Nelson was in Roxbury telling people he was going to get Martorano. It wasn’t the first time Johnny had heard that Nelson was shooting his mouth off, so all night he kept a close eye on the traffic outside on Dartmouth Street. Finally, after midnight, he saw Padron’s silver Mercedes convertible glide past Chandler’s.

  Johnny wordlessly nodded at Nicky Femia, one of Barboza’s old crew who happened to be drinking at Chandler’s that evening. They hurriedly left the bar and got into Johnny’s car, Femia at the wheel, Johnny in the back with a carbine.

  When Nelson comes back around down Columbus and turns right onto Dartmouth Street, we pull up beside him and I let go with the carbine. The next day it was in the papers that the cops said they’d found six bullet holes in the car. But I know I only had time to shoot twice, before Nelson stopped the car. We had to keep driving.

  Poor Nelson, he was hit pretty bad but somehow he managed to drive all the way to Mass. General, and then he crashed the Mercedes into an abutment. He was on the danger list for a while, and with all the bullet holes, the cops had probable cause to search his car. They found a bag of coke, an unregistered handgun, and $2,400 cash in the car. I still remember the headline in the Herald: “He’s riddled by bullets, is arrested.”

  From then on, whenever I saw Nelson, he was on a cane.

  In the daytime, the gang still congregated at Howie Winter’s garage—Marshall Motors. Chandler’s was a nicer place to hang, but it couldn’t accommodate that many wiseguys. It would have been too obvious. So the garage in Somerville was the most logical place for the gang to have its headquarters, and its location soon gave the new mob its name—the Winter Hill Gang. The fact that Howie Winter was one of the bosses of the gang was nothing more than coincidence.

  In the front of the building, there was an actual garage, run by Johnny’s brother Jimmy and Johnny’s old friend George Kaufman. Yet another hood born in 1929, the mild-mannered Kaufman first served as a liaison to the gang members in prison or on the lam, and later to the Jewish bookies from whom “the Hill” would extract tribute.

  In the back of the building were the “offices” of Howie and Johnny. Nobody who owed money ever wanted to be taken back there. On the wall was a poster of two vultures perched on a dead tree in the middle of a desert, with one vulture saying to the other, PATIENCE, HELL, I WANT TO KILL SOMEBODY.

  Next to his desk Howie had a trapdoor built into the floor, leading to the unfinished basement. What the trapdoor was used for was left to the imaginations of his visitors, most of whom owed the Hill money, and all of whom had heard chilling stories about the gang.

  Farther down Marshall Street, Winter owned a house. He lived upstairs and for a nominal rent allowed the other gang members to use the ground floor as a more informal clubhouse than the garage—the Pad, they called it. Joe McDonald’s Fire House was a few doors south.

  With so many known hoodlums congregating in the area, even the Somerville police couldn’t totally ignore the comings and goings. Occasionally they or the state police would raid the garage. So all the mob’s hardware—guns, silencers, stolen cars, etc.—had to be stashed elsewhere. For that purpose, the gang rented a bank of garages a few hundred yards away, at the top of Winter Hill. The garages were particularly useful because the stolen cars—the ones that would be used on hits—could be brought into the garages through a back alley that was not visible from the street. The Hill called the stolen cars “boilers” because they were so hot.

  The garages were also where shotguns could be sawed off, and bodies occasionally dismembered.

  * * *

  WHITEY BULGER was the only original partner who didn’t have some ties to Somerville, but he, too, quickly began spending at least a few hours at the garage every weekday. From the start, though, he was a man apart. Everyone else parked at the garage, but Whitey would always get out across Broadway from the garage in the supermarket parking lot. He always insisted on driving himself, but he brought with him one of his older Southie guys, Jack Curran, who would then drive Whitey’s car back to Southie.

  After getting out of his car, Whitey would pull down his hat and wrap his coat collar up around his neck before walking across the street, in case any cops who had the place under surveillance hadn’t figured out that he showed up there every morning at the same time. He’d leave the garage the same way around 3 P.M., crossing Broadway and getting back into the driver’s seat, while Curran slid across the seat to the passenger’s side.

  Jack Curran drove Whitey’s car back to Southie each day after Bulger arrived at the garage.

  As time went on, more and more hoods frequented the garage. As the old saying went, if you were indicted, you were invited. Now that the gang war against the McLaughlins was a fading memory, Charlestown guys started stopping by, as well as Teamsters from Local 25, and ocassionally Whitey Bulger’s still-uneasy Mullen allies. Black guys from Roxbury occasionally came by to pay their respects to Johnny. The garage was also a good place to get their cars fixed. George Kaufman didn’t ask any questions about bullet holes, or dark, sticky stains on the floorboards.

  The Hill had long been home to many of Boston’s more colorful gangsters. One of Howie’s closest associates from Charlestown was a guy named Tommy Ballou. Ballou always carried two personal possessions: a $100 bill and a longshoreman’s grappling hook.

  Tommy Ballou, a colorful Charlestown hoodlum murdered in 1970.

  If he ever got in a barroom brawl, Ballou would try to get face-to-face with the guy he was taking on. Before his foe could jump him, Ballou would pull out his C-note and throw it up in the air. Usually, the other brawler would be at least half drunk, and would pause just long enough to watch the bill float to the floor, then lean over to pick it up. Which was Tommy Ballou’s cue to grab his grappling hook and sink it into the other guy’s back, thereby ending the fight.

  Ballou had been shot to death in Charlestown a couple of years earlier, but other colorful characters remained on the scene. One of the Local 25 wiseguys had once decided on the spur of the moment to rob the bank on Winter Hill where he had his own accounts, and where, much like the Cheers bar, everyone knew his name.

  After the robbery, the hood quickly realized the extent of his folly. He drove straight to a drug-addled physician who’d been stripped of his license to practice, and who had lately been working under the table, including supplying the drugs that Fat Tony Ciulla sometimes used to fix horse races. The hood ordered the quack to break his leg, then set it, and forge a set of medical documents indicating that he’d been wearing the cast for weeks. That way he could “prove” he couldn’t have robbed the bank, despite what all the eyewitnesses said. He beat the rap, although he would later be indicted in Local 25 shakedowns.

  LAWYER: What was Mr. Bulger’s role in the gang?

  MARTORANO: Intimidating people, mostly.

  Many of the hoods, even Mafia members, stayed around the garage to socialize while having their cars serviced by the garage crews who worked for Kaufman and Jimmy Martorano. Sometimes the other mobsters would wander back into the gang’s offices, jangling their car keys. If they were too loud, Whitey would jump up and order them to stop shaking the keys. He couldn’t take it, he said. It reminded him of the “screws” at Alcatraz.

  Local women—some wannabe molls, others just salt-of-the-earth neighborhood types—would regularly stop by with home-cooked food for the boys. Whitey seethed whenever any female wandered into the garage. He talked even
more about women than he did about Alcatraz, or about taking massive doses of LSD in CIA-sponsored experiments while he was in prison in Atlanta in the late 1950s.

  “Women should be subservient,” Whitey would say, over and over again. “He who controls the purse strings controls everything.”

  At which point, the Somerville guys would surreptitiously steal glances at one another, trying not to let Whitey see their smirks. This guy had obviously never met their broads. They figured he was just running around with project girls from Southie who didn’t know any better. Like Teresa Stanley, his longtime girlfriend. When they were out for dinner, Whitey never allowed her to have more than two drinks, so the other guys in the gang would wait until Whitey went to the men’s room, and then they’d let her gulp down a couple of quick ones. Once Teresa was half in the bag, she’d start mouthing off to Whitey, and that would really drive him over the edge.

  When it came to women, Whitey tried to practice what he preached. One time, a couple of the Mullens were over at his apartment in Quincy. They were all sitting at the kitchen table when suddenly Whitey yelled at one of his girlfriends to bring him his slippers.

  She obediently complied with his order, bringing him the slippers and offering them to him as he sat at the table with his men. Whitey glared at her.

  “I want you to put them on for me,” he said, barely controlling his rage. The woman knew better than to talk back to him. She immediately dropped to her knees and crawled under the table. Then, after struggling to remove the tight-fitting boots he always wore outside, she gently placed the slippers on his feet.

  Later on, I heard he told people he was afraid to have kids because of all the LSD he’d taken in those CIA prison experiments in Atlanta back in the 1950s. Remember all those scare stories they put out in the ’60s about LSD causing chromosome damage?