Whitey Bulger America's Most Wanted Gangster and the Manhunt That Brought Him To Justice (24 page)

Whitey’s family occupied a special circle
that he defended ferociously, especially when it came to his brother Bill, who had been such a loyal advocate while Whitey was in prison. Bill’s success as a politician and his reputation as an erudite spokesman for Southie were sources of family pride. Whitey took it upon himself to be a defender and avenger of that reputation. For example, while Bill Bulger was busy promoting the 1990 gubernatorial bid of his friend John Silber, the president of Boston University, Whitey worked to muddy the name of Silber’s Democratic rival, Frank Bellotti, the former Massachusetts attorney general. Whitey hated Bellotti because Bellotti had once sent his prosecutors after him—an effort, in Whitey’s mind, to soil the family name and humiliate his brother Bill.
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There was no evidence that Bellotti ever got close to indicting Whitey while he was attorney general, but there was plenty of evidence that Bill Bulger didn’t like Bellotti and especially didn’t like Bellotti challenging his friend Silber. He took special offense at Bellotti political ads that drew parallels between Silber’s authoritarian rule at Boston University and Bulger’s iron-fist leadership style as senate president.

Whitey decided to counter Bellotti’s ads with some “ads” of his own, which harkened back to long-ago controversy. Years earlier, a state tax official named John Coady killed himself just hours after he learned he was going to have to testify before a grand jury Bellotti had convened as part of a corruption investigation. Critics accused Bellotti of leading a politically motivated probe and using Coady as a pawn to get at others, and the suicide reflected badly on Bellotti’s office. Eight years later, Whitey and Weeks drove around spray-painting “Remember John Coady” on sidewalks, walls, and highway bridges. The vandalism was noticed, and it inspired news stories.
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Bellotti ended up losing the primary, and Whitey boasted to Weeks that they had cost Bellotti the election—a dubious claim. “He was as proud of that as any crime that made him money,” said Weeks. “He had helped a friend of his brother’s.”
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Bellotti believes Whitey cost him votes not just by reminding people of John Coady. “Whitey and Weeks were going around town, tearing my signs down,” Bellotti said.
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Bill Bulger also had a long-running feud with a state senator named Alan Sisitsky, who, in the early 1980s, began acting erratically and publicly accusing Bulger of corruption. At one point, Sisitsky rose in the senate and proclaimed that the senate president’s brother, Whitey, was eavesdropping and knew all that was being said.
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After Sisitsky’s behavior became more extreme and unsettling, Bill Bulger expelled him from the senate chambers, and Sisitsky’s family hospitalized him. But Whitey had a different sort of intervention in mind. He instructed Weeks to call Sisitsky on the phone. “I know where you live,” Weeks hissed. “I’m gonna kill you.”
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Weeks believes Whitey wouldn’t have stopped harassing Bill’s political enemies even if Bill had asked. But Bill Bulger told a congressional committee that he did press his brother to back off once, when Whitey confronted Patrick Loftus, Bill Bulger’s challenger for an open senate seat in 1970. “Jimmy took it as a personal affront to him when someone went after Billy,” Weeks said. “But he didn’t make a big deal about it. He called it a hobby. He had hobbies. This was one of them.”

Another of Whitey’s favored pastimes
was giving gifts to his friends in the FBI, particularly at Christmas. Those friends occupied a circle that Whitey considered both personal and professional. Blurring those lines enabled him to conduct his criminal business without fear of prosecution and to remain an FBI informant long after any reasonable justification had expired.

The gift giving was a holiday tradition, carried out at the kitchen table at Teresa Stanley’s house on Silver Street. Whitey kept the gift list on a small piece of paper. There were symbols and nicknames. Vino was John Morris, because of his fondness for wine. Pipe was FBI supervisor Jim Ring because he smoked one. Nicky was FBI Agent Nicholas Gianturco. Agent Orange was FBI Agent John Newton because Whitey believed he had served in the Vietnam War. As Whitey chose a gift for each of them—cash or Lalique crystal or a Chelsea clock—he’d cross off a name.
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“Christmas,” Whitey told Weeks, as he stuffed the envelopes, “is for cops and kids.” The gifts were delivered by John Connolly, whom Whitey gave three nicknames: Zip, because they grew up in the same zip code; Neighbor, because they lived near each other; and Elvis, because of the way Connolly combed his thick black hair. And the gift giving was reciprocal. Whitey was especially fond of a belt that FBI Agent Nick Gianturco gave him. The buckle was emblazoned with “Alcatraz 1934–1963”—the active lifespan of the federal prison on The Rock.
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Gianturco first met Whitey in 1979, after being told by Connolly that the gangster had saved his life. As Connolly told the story, Whitey warned him that truck hijackers whom an undercover Gianturco was working with had figured out he was an agent and were going to kill him. The claim was almost certainly specious—the supposed threat was never forwarded to Gianturco’s supervisors, and the gangster who allegedly made the threat was never charged with making it—but it enhanced Whitey’s value as an informant. One evening, Gianturco was invited along when John Morris, at Connolly’s urging, held a celebratory dinner for Whitey and Flemmi at the FBI supervisor’s home in suburban Lexington. Connolly had urged Morris to hold the dinner so Morris and other agents could get to know Whitey and Flemmi. The dinner party itself was extraordinary: gangsters and G-men, sitting around the table, pouring each other wine, praising the steaks and their company. It was at that dinner, Flemmi says, that Morris told him and Whitey that they could do anything they want, with one caveat: Just don’t clip anyone.

Gianturco liked Whitey and Flemmi so much that on four separate occasions he hosted dinners for them and his colleagues at his own home in Peabody, north of Boston. He admitted that they regularly exchanged small gifts. At one dinner, Whitey gave Gianturco a toy truck, a not so subtle reminder of how Whitey supposedly had saved his life from the truck hijacker.
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The gifts Whitey gave Morris and Connolly were more substantial. Whitey knew his wine and frequently gave Morris bottles and even cases of it. As they were leaving one of their dinners at Morris’s girlfriend’s apartment, Whitey handed him five thousand dollars.
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Morris was keeping a family at home and a mistress on the side. Whitey understood the pressures, financial and otherwise. He was keeping two mistresses himself.

There were other dinners: at the Flemmi house in South Boston where Mary Flemmi made her son proud by cooking up an Italian feed for Whitey, Flemmi, and a table of FBI men. At one of them, in 1983, the plates had been cleared and the gangsters and FBI agents were enjoying after-dinner drinks when Bill Bulger walked in from next door. Jim Ring, who had just succeeded Morris as the organized crime squad’s supervisor, was stunned to see the senate president pull out photographs from a recent trip to Ireland and begin showing them to the dinner guests.
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Bill Bulger’s presence seemed like a postdinner benediction, a tacit blessing from one of the most powerful politicians in Massachusetts of the unholy alliance between gangsters and federal agents. The social dinners, the exchange of gifts, the friendly banter, and even his brother’s witness—all were confirmation to Whitey that he and his FBI handlers were on equal footing. They were partners in an enterprise that served their mutual interests. In Whitey’s mind, they also kept the world a safer place by making the underworld a more orderly place.

Weeks found out how seriously Whitey took the relationship with Connolly and the FBI when, one day in 1984, Connolly drove up to the liquor store that Whitey had begun using as his headquarters. The South Boston Liquor Mart was a squat, one-story building standing between the two housing projects where Whitey and Weeks had grown up. The sign over the entrance featured a shamrock, and there was another, much larger, shamrock painted on the whitewashed cinderblock exterior. The store was crammed with narrow rows of wine racks, and cases of beer were piled to one side. Weeks was standing behind the counter when Connolly walked in. He viewed Connolly dyspeptically—just another corrupt agent, with his hand out—and offered no greeting. “What’s up?” Connolly asked Weeks. “What’s going on?” Connolly was looking for “the other guy”—Whitey—but the gangster wasn’t there. When Whitey returned to the store, Weeks relayed the story. “He has some fuckin’ nerve,” Weeks told Whitey, “coming in and saying, ‘What’s going on?’ Like I’m going to fuckin’ tell him what’s going on.” Weeks expected to be praised for his discretion, but Whitey was furious. “Shut the fuck up!” he hissed. “Don’t ever talk about that guy like that. He’s a friend of ours.”
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It was a telling phrase. Calling someone “a friend of ours” was what a Mafia wiseguy would say about another made guy.

Connolly insisted to other agents, and even to his supervisors, Morris and Ring, that Whitey and Flemmi were to be treated not as criminals but, as he put it, associates. Connolly’s relationship with Whitey was as much social as professional. They took vacations together and occasionally traveled to Provincetown. During a particularly snowy winter in 1978, Whitey and Connolly vacationed together in Mexico. They got into an accident while Whitey was driving, leaving Connolly with a black eye he had to explain back at the FBI office.
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Connolly enjoyed traveling with a guy who dispensed cash like an ATM. For Whitey, there were perks as well. Once, when they confronted long lines at an airport in Mexico, Connolly and Whitey walked to the front of the line. Connolly flashed his badge and introduced Whitey as a fellow FBI agent. They were escorted onto the plane together without having to wait in line.
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But for all the conspicuous camaraderie, there was a built-in imbalance in their bond. “I got the sense that Connolly envied us. One day he said to me and Jimmy and Stevie, ‘You guys have all the fun.’ He would have been indebted to Billy for getting him into college and all that. But Jimmy was the guy he wished he was,” Weeks said.

Sometimes Connolly, who was a divorced bachelor in the early 1980s and maintained an active social life, displayed the perks of the partnership too openly. His flashy suits and pinky ring, his vacation home on Cape Cod with the twenty-seven-foot boat, didn’t match his modest FBI salary. “He’s gotta tone it down,” Whitey told Weeks. “You can’t call attention to yourself.” Flemmi says Whitey convinced Connolly to sell the boat that Connolly had bought with cash they’d given him.
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Whitey was also upset when Connolly bought a condo in the same six-unit complex on West Fourth Street in which Whitey and Weeks had bought units. Whitey worried that it would draw unwanted scrutiny. “Stupid,” Whitey said.
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But, more often, Connolly and Whitey worked together seamlessly, and their meetings produced a large number of thick reports. Connolly did more than pad Whitey’s informant files. He also often acted as Whitey’s public relations consultant, propagating Whitey’s own view of himself as a disciplined criminal who did not engage in gratuitous violence, a neighborhood vigilante using force for the greater good. Connolly cultivated contacts throughout the Boston media and invariably emphasized the image of Whitey as the good bad guy to reporters. Sometimes, too, Connolly worked to burnish Bulger’s name by tapping him for help on high-profile cases. After a nine-year-old girl was abducted and disappeared from an affluent Boston suburb in 1985, the FBI agent handling the case, Dick Baker, told Connolly that they had identified a suspect in the disappearance, a twenty-two-year-old man from South Boston. Connolly asked Whitey to smoke the suspect out—to visit the young man in the jail in which he was being held on unrelated charges and get him to reveal where the girl’s body was buried. The young man was terrified to find Whitey Bulger’s emissary, Kevin Weeks, waiting for him in the visiting area, and he convincingly denied having had anything to do with the crime. Whitey had long fancied himself as having been deputized by the FBI. In this case he essentially was. He reported back, telling Connolly and Baker, “I do not believe this guy did it.”
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The FBI’s investigation into the disappearance and presumed murder of a nine-year-old girl was, in this instance, directed by the gut feelings of Whitey Bulger. The woman who initially led investigators to the twenty-two-year-old man later admitted she had made up the whole story.

Connolly was more than Whitey’s chief handler; he was his chief apologist. He insisted that Whitey and Flemmi “were an extension of the police department, the difference between anarchy” and normality. Connolly didn’t deny that Whitey and Flemmi were killers. “I don’t think they ever killed anyone who wasn’t trying to kill them or wasn’t going to rat them out,” he said.
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And Connolly never accepted the premise that it had been a mistake to let a Southie agent work with a Southie wiseguy. It wasn’t a conflict of interest, he would say, it was a convergence of them. “I liked him. I liked him a lot,” Connolly said. “We came from similar circumstances. But I never lost sight of who he was and what he was. Some people say you shouldn’t put the hometown boy in charge of the hometown guy. Who the hell else is going to talk to the hometown guy? He wouldn’t talk to anyone else.”

Connolly looked at the whole uncommon arrangement as one of priorities and numbers. The FBI’s priority was taking out the Mafia. Whitey and Flemmi delivered Italians. “It was a brilliant business decision,” Connolly said. “We got forty-two stone criminals by giving up two stone criminals. What’s your return on investment there? Show me a businessman who wouldn’t do that.”
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That wasn’t just Connolly’s opinion. It was the opinion of the FBI leadership in Boston and Washington, who rewarded him for recruiting and maintaining a top-echelon informant like Whitey Bulger. During the 1980s, Connolly’s FBI salary grew from $45,000 to $65,000.
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But during that time, he would let his desk drawer fill with paychecks. An FBI assistant was astonished when Connolly called her at the office and asked her to leave his check in his desk drawer; she opened the drawer and counted ten others lying there.
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He was living beyond his means and still left his checks uncashed. Something didn’t add up.