Even though Rico had instructed Flemmi that he was not to consider himself an employee of the FBI and had gone over with Flemmi some of the FBI’s other ground rules for informants, the agent and Flemmi regarded most of those instructions as an annoying formality. What was important was that Rico had promised Flemmi he would keep confidential the fact that Flemmi was his informant, and this was the key to their alliance. It was a pledge most agents customarily gave to their informants, a pledge viewed as “sacred.” But in Rico’s hands the promise was sacred above all else, even if it required that he commit the crime of aiding and abetting a fugitive. Rico promised that as long as Flemmi worked as his informant he would see to it that Flemmi wasn’t prosecuted for his criminal activities.

For obvious reasons, such a deal had proven advantageous for Flemmi. He also liked how Rico did not treat him like some kind of lowlife gangster. Rico wasn’t the pompous G-man ready to spray the room with disinfectant immediately after he’d left. He was more like a friend and an equal. “It was a partnership, I believe,” said Flemmi.

Eventually the criminal charges against Flemmi were dropped, after key witnesses recanted, and in May 1974 Flemmi was able to end his fugitive life and return to Boston. With the help of the FBI, he’d survived the gang wars and outlasted the murder and car bombing charges. But Flemmi had no intention of going straight. Once back in Boston he’d hooked up with Howie Winter and gone back to what he knew best. And now he was standing alongside Whitey Bulger at Marshall Motors. “Should I meet him?” Bulger had asked. Flemmi thought for a moment. He had been back less than a year, and it was obvious to him that things were in flux. It was clear that some new arrangement was in the works. He’d even met on his own with Dennis Condon, a short meeting at a coffee shop where he was introduced to John Connolly. Flemmi regarded all the huddling as a kind of “transition,” with Connolly being set up to take over now that Paul Rico was transferred to Miami and nearing retirement. Over time, of course, Flemmi had experienced a strong upside to his FBI deal. But he was just Stevie Flemmi, not the already legendary Whitey Bulger.

Flemmi cautiously opted for a short answer. It was an answer soaking in subtext, but short nonetheless.

“It’s probably a good idea,” he told Bulger. “Go and talk to him.”

CONNOLLY wasn’t in 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, Gennaro 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.”

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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 gruntwork 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 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, 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 still 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 John Connolly was surely thinking about his career, the deal wasn’t about what might come—it was about where he had come from. A circle, a loop, the shape of a noose. All roads led to Southie.




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