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.
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