LITMIR.BIZ

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any rush to make his pitch. “I just want you to hear me out,” he told Bulger in the car along Wollaston Beach. Connolly carefully played up the double-barreled threat that Bulger and his Winter Hill gang presently faced from Gennaro Angiulo’s Mafia. “I hear Jerry is feeding information to law enforcement to get you pinched,” he told Bulger. They talked about how Jerry Angiulo definitely had an advantage over the rest of the field, able to call on a crooked cop to do him a favor. “The Mafia has all the contacts,” Connolly said.

      Then Connolly moved along and stoked the vending machine dispute. Word on the street, observed Connolly, was that Zannino was ready to take arms against Bulger and his friends in the Winter Hill gang. “I’m aware that you’re aware that the outfit is going to make a move on you.”

      This last remark especially caught Bulger’s attention. In fact, the LCN and Winter Hill had always found a way to coexist. Not that there weren’t disputes to work out, but the two groups were closer to being wary partners than enemies on the verge of a war. Even the vitriolic and unpredictable Zannino, the Mafia’s Jekyll and Hyde, could one moment angrily denounce Winter Hill and promise to mow them down in a hail of bullets and then suddenly turn operatic and proclaim lovingly, “The Hill is us!” Truth be told, Angiulo was at this time more concerned about threats he was receiving from a runaway Italian hothead known as “Bobby the Greaser” than he was about imminent war with Winter Hill. But for Connolly’s purposes it was better to play up the beef percolating between the LCN and Winter Hill over the vending machines, and Connolly could tell right away he’d hit a hot button with the fearless Bulger when he mentioned the potential for violence. Bulger was clearly angered.

      “You don’t think we’d win?” Bulger shot back.

      Connolly actually did think Bulger could prevail. He fully believed Whitey and Flemmi were much tougher than Angiulo and his boys—”stone killers” he called Bulger and Flemmi. But that wasn’t the point.

      “I have a proposal: why don’t you use us to do what they’re doing to you? Fight fire with fire.”

      The deal was that simple: Bulger should use the FBI to eliminate his Mafia rivals. And if that alone wasn’t reason enough, the FBI wouldn’t be looking to take Bulger himself down if he were cooperating. In fact, at that moment other FBI agents were sniffing around and making inquiries into Bulger’s loan-sharking operations. Come aboard, Connolly said. We’ll protect you, he promised—just as Rico had promised Flemmi before him.

      Bulger was clearly intrigued. “You can’t survive without friends in law enforcement,” he admitted at night’s end. But he left without committing.

      Two weeks later Connolly and Bulger met again in Quincy, this time to cement the deal.

      “All right,” he informed Connolly. “Deal me in. If they want to play checkers, we’ll play chess. Fuck them.”

      This was music to John Connolly’s ears. Incredibly, he’d just brought Whitey Bulger into the FBI. If developing informants was considered the pinnacle of investigative work, Connolly was now, he proudly concluded, in the big leagues. In a single bold stroke he’d put FBI grunt work behind him and now belonged to an upper crust occupied by the likes of the retiring Paul Rico. If, in Connolly’s mind, Rico was the agent whom a slew of the new young turks in the office wanted to model themselves after, Bulger was the neighborhood legend all the kids in Southie were in awe of. Connolly had to sense that the moment marked the slick merger of both worlds.

      Moreover, this particular deal had a certain élan to it. The last gangster anyone in Boston would suspect of being an FBI informant was Whitey Bulger of South Boston. Indeed, through the years Connolly was always sensitive to this seeming incongruity. Among his FBI colleagues Connolly rarely, if ever, called Bulger an informant, a rat, a snitch, or a stoolie. He would always grate when he later heard other people use those labels. To him Bulger was always a “source.” Or he used the terms that Bulger requested: “strategist” or “liaison.” It was as if even the man who convinced Whitey to become an informant couldn’t believe it himself. Or maybe it was just that the deal from the beginning was less a formal understanding with the FBI than a renewed friendship between Johnny and Whitey from Old Harbor. And though Connolly was surely thinking about his career, the deal wasn’t about what might come; instead, it was about where he had come from. A circle, a loop, the shape of a noose—all roads led to Southie.

      Connolly always remained deferential to the older Bulger, calling him by the birth name he preferred, Jim, rather than the street name that the media preferred. Such things might have seemed like petty details, but they were details that made the deal palatable. Bulger, for example, insisted that he would provide information only on the Italian Mafia, not on the Irish. Moreover, he insisted that Connolly not tell his brother Billy, then a state senator, about this new “business deal.”

      There was a certain charged and inescapable irony to this deal between Bulger and the FBI, coming as it did during the second year of court-ordered busing in South Boston. The tableau, in its entirety, was bizarre. The people of Southie, including leaders like Billy Bulger, had been helpless in their efforts to repel the federal government, which was plowing through the neighborhood to enforce busing. The federal authority was mighty and despised and would not go away. This was the harsh reality of the neighborhood’s public life. But in a different part of Southie, Whitey Bulger had cut a deal that would freeze the feds. The FBI needed Whitey and would not be looking to do him in. The rest of the world might belong to the feds, but at least the underworld did not. Whitey had found a way to keep them out of his Southie. In an odd way he’d succeeded where his brother had not.

      Immediately the information highway was up and running. More meetings were held. Bulger blended in Flemmi, and a package deal was forged. For his part, Bulger clearly recognized the value of teaming up with Flemmi, given Flemmi’s rich access to mafiosi and the kind of information Connolly so badly wanted. Flemmi, meanwhile, had to recognize the value of teaming up with Bulger, not just for his cunning mind but also for his marquee status, particularly with Connolly. He could see something special pass between them right from the beginning: “They had a relationship.”

      For Connolly, Flemmi was a hand-me-down, but Bulger was his own, a coup for the FBI in Boston. It was a beast of a deal, a high-five achievement, with Connolly in charge of two midlevel gangsters positioned to assist the FBI in its stated campaign to cripple the Mafia enterprise. But the new deal hardly meant that Whitey would curb his style. In fact, just five weeks after the Whitey Bulger informant file was officially opened on September 30, 1975, Whitey chalked up his first murder while on FBI time. He and Flemmi took out a longshoreman from Southie named Tommy King. The hit was part power grab, part revenge, and mostly Bulger hubris. Bulger and King, never friends, had gotten into an argument one night in a Southie bar. Fists began flying. King had Bulger down and was pounding away on him when others finally pulled him off. Payback for Bulger came November 5, 1975. No doubt buoyed by the secret knowledge the FBI would always be looking to curry favor with him, Bulger, Flemmi, and an associate jumped King. The longshoreman vanished from Southie and the world. Not surprisingly, Bulger mentioned none of this in his meetings with Connolly; instead, one of Bulger’s first reports was that the Irish gang unrest and bloodshed supposedly pending between Winter Hill and the Mafia had fizzled—much ado about nothing. The streets were calm, reported Bulger.

      So it began.

      CHAPTER TWO

       South Boston

      In order to wait for Whitey at Wollaston Beach, John Connolly had to first get himself home from New York. Flemmi’s boyhood pal “Cadillac Frank” Salemme would be his ticket.

      Salemme’s arrest happened on a cold bright New York afternoon in December 1972, when the good guys and the bad guys floated past each other on Third Avenue. A face in the crowd suddenly clicked with Connolly, who told his FBI companions to unbutton their winter coats and draw their guns. A slow, almost comical footrace on snow ended with jewelry salesman Jules Sellick of Philadelphia protesting that he was not Frank Salemme of Boston, wanted for the attempted murder of a mobster’s lawyer. But indeed he was.

      The

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