Whitey Bulger America's Most Wanted Gangster and the Manhunt That Brought Him To Justice (18 page)

In what would become a pattern, Connolly falsified reports and credited Whitey with detailed information about the activities of a Mafia leg breaker. But eight months later, in a memo that justified keeping Flemmi on as an informant, Connolly credited Flemmi for the same information. It was Flemmi, not Whitey, who associated with the Mafia figures on a regular basis.
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Connolly not only allowed Whitey and Flemmi to believe they were, as Whitey put it, strategists and not snitches, thus avoiding in their minds the stigma of the rat; he bought into it, adopting the language they used. “These guys were not informants, they were strategists,” Connolly insisted. “They were never paid and we could never ask them to hurt their friends. Their deal was, if the Mafia wants to play checkers, we’ll play chess.”
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Connolly also insisted that neither he personally nor the FBI as an agency gave Whitey and Flemmi the green light to commit murders to enhance their cover. But he acknowledged that they were killers, and that they were encouraged to do everything short of murder. To Connolly, it seemed naïve in the extreme to imagine you could recruit top-level criminals as sources and then expect them to mend their ways. If they were to be of any use at all and remain credible with the mobsters they mixed with, Whitey and Flemmi had to stay their brutal selves. “They were like Mafia members,” Connolly said. “You’re dealing with stone killers. That’s who you’re trying to recruit. Then you’re supposed to tell them you can’t do that anymore? Are you shitting me?”
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Whitey and Flemmi were anything but shy about playing this two-sided game. They became in fact, the epitome of lethal hypocrisy, and would spend a decade killing people who were, for the most part, actual or potential informants for law enforcement. And whenever they went out on a hit, Whitey and Flemmi preferred the company of their friend and Winter Hill partner John Martorano.

Martorano had grown up in a well-to-do family in Milton, an affluent suburb just south of Boston. His father ran a restaurant and successful after-hours club that attracted a gangster clientele. Martorano attended a prestigious Catholic prep school in Rhode Island; among his well-heeled classmates was a poor kid on scholarship who would grow up to be the CBS newsman Ed Bradley. Like a lot of well-off suburban kids, Martorano went to summer camps in the Berkshires. But he found himself drawn more to the hit men who drank at his father’s bar in downtown Boston than to his classmates who went on to the Ivy League. He started working at his father’s place right out of high school, learning things they didn’t teach in college.

Unlike Whitey and Flemmi, Johnny Martorano didn’t watch what he ate, didn’t count his drinks, and had trouble keeping count of how many people he had shot. While Whitey and Flemmi were discreet with their cash, Martorano was flashy. He wore a huge Rolex on his wrist and drove a big Mercedes-Benz. But whatever Martorano lacked in self-discipline he more than made up for in his utter and complete willingness to kill anyone, anywhere, especially at the behest of a friend. And Whitey and Flemmi were his friends. He committed his first murder in 1965, when he was twenty-four, at Flemmi’s request. There was a guy named Bobby Palladino who Flemmi thought might implicate his brother Jimmy in a murder. Martorano shot Palladino before he could give up Jimmy Flemmi.
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Killing snitches, or potential snitches, became his forte. He had no idea that the two men who most often put him up to this were snitches themselves.

Flemmi was on the lam in Canada when Whitey and Martorano first went hunting together, dispatching various enemies of Winter Hill. In December of 1973, they went gunning for a rival gangster named James “Spike” O’Toole. O’Toole was one of the last living members of the McLaughlin gang from Charlestown. One night, O’Toole was drinking at Bulldogs, a bar in the Savin Hill section of Dorchester. Eddie Connors, a former boxer who owned Bulldogs, knew O’Toole was on the Winter Hill hit list, and he made a phone call. Before O’Toole had finished his drink, Whitey and Martorano were parked outside the bar. O’Toole had walked a few blocks away from the bar when Whitey pulled the car alongside of him. O’Toole scampered behind a mailbox but Martorano just fired through it.
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By Martorano’s account, he and Whitey had done a half-dozen murders together by the time they set off with Flemmi on the first of what would be many hits by the trio. It was 1975, and their prey was Eddie Connors, the bar owner, who was himself a marked man, and for more than one reason. There were claims that he had bragged openly about helping Winter Hill kill O’Toole. Howie Winter, meanwhile, worried that Connors could implicate him in an armored car robbery for which Connors was awaiting trial.
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Connors was a former New England middleweight champion, and that toughness was sometimes useful, but he was also considered a risk to talk if facing a long prison stretch. And so he had to go.

Connors was told that Winter wanted to talk to him. He was instructed to go to a pay phone at the corner of Morrissey Boulevard and Freeport Street, about a half mile from Bulldogs. Shortly after 9:00 p.m. on a rainy June night, Connors pulled his black Lincoln Continental up next to the phone booth and left the car door open and the motor running as he stepped in and waited for the call. A police van parked a few hundred feet away had left moments before, lured away by a phony report of a bad accident nearby. The call Eddie Connors was waiting for never came, but Whitey and Flemmi did, running out of the shadows toward their cornered victim. Whitey fired a sawed-off shotgun, bringing Connors down, then pulled a .38 revolver and emptied it into him as Flemmi raked him with bullets from a carbine.
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Connors slumped to the floor of the phone booth. One of his legs protruded through the smashed glass panel. The phone dangled by its cord.
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Martorano usually did the shooting, but this time he was the getaway driver. Whitey and Flemmi jumped into the car, adrenaline pumping, and Martorano drove away from the scene at a leisurely speed. They were less than a half mile away when an impatient Whitey ordered Martorano to pull over. Whitey said he knew the area better. They switched places and Whitey pushed his foot to the floor. They were in Somerville fifteen minutes later.
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Despite the occasional petty dispute, the three proved a most effective hit team. Flemmi said he and Martorano helped Whitey pick off some of his remaining Mullens gang rivals. And in 1976, the three men got together again to kill Richie Castucci, a bookmaker who doubled as a professional gambler. It was a bad combination, as potentially destructive as an alcoholic owning a barroom; there was always the temptation to sample the product. Flemmi says they killed Castucci because John Connolly had told Whitey that the bookie was, in fact, an FBI informant. More precisely, Castucci had compromised the New York City hiding place of some Winter Hill fugitives. That would have been enough to get him killed, but there was a secondary motive—money. If Winter Hill got rid of Castucci, they wouldn’t have to pay two hundred thirty thousand dollars they owed him in gambling debts.
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Castucci was called to the garage on Marshall Street on the premise that Winter Hill was going to hand over the first installment of the debt. Martorano told him it was sixty thousand dollars and that they had it at a nearby apartment, where Castucci was welcome to count it. Whitey led Castucci to the apartment and even went so far as to let him start counting a large stack of cash in small bills. Martorano came to the apartment minutes later. Castucci was trying to keep the numbers in his head when Martorano put a snub-nosed .38 revolver to his ear and fired.
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They stuffed him in a sleeping bag and put him in the trunk of his car.

Richie Castucci, a forty-eight-year-old father of four, was dead, but Winter Hill’s gambling debts were not. A good chunk of the two hundred thirty thousand dollars due Castucci was actually owed, through him, to the Mafia in New York. When a few New York Mafiosi came north for a meeting at the Somerville garage to collect, Whitey recognized one of them as someone he had been in prison with.
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The Mafiosi noticed that the garage was crowded with far more people than cars; Martorano had arranged for fifty local gangsters to be on hand as a show of force.
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They stood around in wary clusters in the service bays. The New York Mafiosi were chaperoned by Sonny Mercurio, a Mafia soldier in Boston who later became John Connolly’s informant on the recommendation of Whitey and Flemmi.
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The Mafia men started shaking their heads when Martorano told them Winter Hill wouldn’t pay because Castucci had been a snitch and so had his bookie partner.
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It was a standoff rich with irony: one FBI informant outed, another killed, all at the behest of another FBI snitch named Whitey Bulger. But Winter Hill’s ploy worked. The Mafia men walked away empty-handed.

Still, Whitey and Flemmi weren’t satisfied with taking Castucci’s life and wiping out the gambling debt. They also wanted Castucci’s financial interest in The Squire, a popular and highly profitable strip club in Revere. Castucci’s widow, Sandra, was terrified when Flemmi showed up unexpectedly at her Revere Beach home a year after her husband’s slaying. He asked about the stake in the club and suggested he should handle it for her. She had never met Flemmi but knew of his reputation. She reported the visit to her husband’s partner. The Mafia quickly got involved, and this time they won. New England Mafia boss Raymond L. S. Patriarca summoned Sandra Castucci to a meeting in a back room of a store in Providence, Rhode Island. The Don told her that he was seizing her husband’s share of the club because he had died owing him money. Sandra Castucci was left with nothing, but she was too frightened to go to the police. And the FBI, which knew she had been fleeced, looked the other way.
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The murder of Richie Castucci demonstrated to Whitey and Flemmi that the FBI would protect them no matter what. Whitey and Flemmi knew they could even kill other informants and it would be excused by the bureau as the cost of doing business with dangerous people. Years later, Castucci’s handler, FBI agent Tom Daly, was asked, “What, if anything, did you do to investigate the murder of your own informant?”

“Nothing,” Daly replied.
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Sometime in the mid-1970s,
Joe Oteri’s law office in downtown Boston became Whitey’s and Flemmi’s favored meeting spot. It was much plusher than the garage in Somerville and contained exercise equipment of the sort the mobsters enjoyed. Health clubs were the craze at the time, but Whitey and Flemmi couldn’t be bothered paying for memberships or mixing with strangers. They used the law office’s state-of-the-art gym instead. The office was typically thick with Winter Hill gangsters; Oteri’s firm represented a number of them. Whitey and Oteri knew each other well, going back to elementary school days. One of the most successful criminal defense lawyers in town, Oteri was also a Southie guy, and a marine. He had attended the Hart School in South Boston with Whitey. Oteri remembered Whitey as the kid who just walked out of school.

As the son of Italian immigrants, Oteri had a different perspective on the clannishness of South Boston. The Irish, so dominant in numbers, dominated the Italians. “I never knew I was Italian,” Oteri said. “I thought I was a guinea, because that’s all I was ever called.” In those days, there was a matter-of-factness about the bigotry in Southie, an air of innocence about—or was it indifference to?—the invidious ethnic divides. Because a large number of Italian families clustered around Emmet Street in South Boston, the locals called it “Guinea Emmett,” almost with fondness. Almost. “We had a fight a week,” Oteri said. “The Irish kids would call us guineas until someone fought.”

The animosity was the product of immigration patterns and a change in the fortunes of the various groups. The Irish were treated poorly by the Brahmins when they filled Boston during the second half of the nineteenth century. By the time the Italians began arriving in great numbers in the early part of the twentieth century, the Irish had been able to make serious inroads in politics and filled the police and fire departments and other municipal jobs with their own. The Italians were on the lower rung, and the Irish wouldn’t let them forget it. “Ethnicity was terribly important in the city, but nowhere more so than Southie,” said Oteri. “And especially down around Andrew Square and the projects, so Whitey would have grown up in that.”

But Oteri was not surprised that when it came to picking a business partner, Whitey chose Flemmi. “My best friend growing up was an Irish kid,” Oteri said. “On a personal basis, everything was fine. But in a group, we were all guineas. It was groupthink, not individual think. Whitey and Stevie were very similar as persons, that’s why they teamed up. The Irish-Italian thing didn’t have anything to do with it, except that the FBI wanted to go after the Mafia and Whitey and Stevie knew what was good for them.”

Oteri’s office was in Post Office Square, right across from the federal courthouse where more than a few of his clients had regular appointments. Whitey and Flemmi started dropping by the office every other day, mainly to use the gym. “They liked the free weights,” Oteri said. “They were very competitive, trying to lift more than each other.” After a workout, they would sit around, having lunch and shooting the breeze. Whitey would pick at his salad and sneer as Oteri bit into a hamburger. “That stuff’ll kill ya,” Whitey told him.

When they discussed cases, Whitey was anxious to impress. One day, as Oteri debated the option of taking a plea or going to trial in the case of a Winter Hill associate, Whitey said, “Joe, that is a Scylla and Charybdis.”

Oteri laughed out loud, and Whitey looked at him with dead eyes.

“Jimmy,” Oteri said, holding his hands out, trying to explain his reaction. “I’m not laughing at you. I’m laughing because there’s only three guys in Massachusetts who know what you mean: you, me and Alan Dershowitz.”