Black Mass

Connolly pulled over a few blocks from the apartment Bulger had begun using after closing down his mother’s place in Old Harbor following her death. Once inside, Newton just sat and kept his mouth shut for the first hour or so, as the other three talked business, mostly about the Mafia’s Angiulo. Then, said Newton, “we just had a general conversation.” They talked about “military topics and things.” They opened a bottle of wine. They all drank, including Whitey, a sign that he was completely at ease.

This was the first of a number of times Newton tagged along for a session with the two informants. Just like that, Connolly had enlarged his circle.

By now Connolly was right back into the old neighborhood. He had bought a house at 48 Thomas Park in 1980, on a street atop one of Southie’s rolling hills; more than a few notches above the Old Harbor project in status, these hills, two centuries earlier, had been a windswept pasture of rich grass with a commanding view. Like all the surrounding streets, the natural topography had long since been covered by rows and rows of double- and triple-deckers and shingled houses built right up against one another. They formed the wall of residences in the tightly woven Irish-American community. The FBI agent’s new home was also situated across from South Boston High School, the battleground over forced busing just a few years earlier.

In Connolly’s work, day was night; Bulger usually came around for a secret meeting after hours, while most of Boston slept. Sometimes even Connolly was asleep, dozing off on the couch with the TV on. He’d leave his door unlocked for Bulger and Flemmi, and the two mobsters would walk right in and make themselves at home.

Connolly appreciated the company. Now in his early forties, he was also officially single again. Citing an “irretrievable breakdown” after a four-year separation, his wife had filed for divorce in January 1982. Marianne, a registered nurse, was making do on her own. They’d split up their things long before, and with no children, the divorce was a routine, uncontested matter that became official a few months later. Now Connolly was out and around town, the ladies’ man others in the office knew him to be. Like Bulger and Flemmi, he showed a preference for younger women. The twenty-three-year-old Elizabeth L. Moore, a stenographer at the office, had caught the flashy agent’s eye, and the two were an item. They were soon off together to a getaway on Cape Cod, where Connolly, fulfilling the dream of so many who grow up in Boston, now owned his own place, an $80,000 condo in Brewster.

Morris was jealous of the new couple. His own marriage was also irretrievably broken down, and he struggled seeing Connolly free to escort a new young girlfriend in the city while he could only sneak around with his: Debbie Noseworthy, an FBI secretary who worked directly for Morris and his Organized Crime Squad. The adulterous affair was an open secret at the office, but for Morris it was a lie that began to eat away at him. There would soon be more and far worse deceptions to come.

EVEN though Morris and Connolly had dodged a bullet during the Sarhatt review, the two agents did not want to take any chances. They had to make sure no one would again second-guess their ties to Bulger and Flemmi. To carry this off they would have to play off the high-minded provisions in the agency’s guidelines for monitoring informants. There was a fundamental tension in the guidelines that could be exploited. To secure intelligence, agents like Connolly and Morris were, on the one hand, encouraged to court gangsters like Bulger and Flemmi. And for the deal to work, gangsters were going to have to be given some breathing room.

The question was, how much? How much criminal activity could the FBI tolerate? In theory, no deal was without limits. FBI managers and handlers were always supposed to be evaluating their informants. The crux of oversight could be reduced to two issues: balancing the value of the informant’s intelligence against the severity of his crimes. The trick in the Boston office was to manipulate those two sides of the equation, and inside the FBI no two agents were better positioned to shape the hierarchy’s views than a handler and his supervisor.

Connolly and Morris were right there at ground control. To keep the flame burning bright, the two began creating the FBI paperwork that downplayed Bulger and Flemmi’s dark side while inflating the value of the intelligence they provided. Connolly was the Bulger chronicler, and Morris signed off on the narrative. They possessed enormous influence up the chain of command and, between them, seemed to have every FBI angle covered. The Irish of South Boston have long been known for being great storytellers. In the Bulger file, native son John Connolly showed himself to be one of the great spinners of tall tales. John Morris would do pretty well for himself too.

THE crudest technique involved outright lying.

During the late 1970s, as the FBI’s reliance on Bulger and Flemmi hardened, Morris had shown a knack for mendacity in his internal reports about Bulger in the race-fixing case. He’d reported that contacts with Bulger had ceased when, in truth, Connolly was seeing him regularly. Morris then lied in reports he’d filed to Sarhatt during the internal inquiry about leaks in the state police’s bugging of Bulger and Flemmi at the Lancaster Street garage. For his part, Connolly sometimes filed reports to satisfy certain FBI rules that Morris afterward admitted were false. In one instance Connolly described a meeting he and Morris supposedly had had with Bulger and Flemmi to go over the warnings and ground rules agents were required to discuss with their informants. The report documenting the so-called annual review included a time and date, but Morris later admitted: “I do not believe such a meeting took place.”

The more artful moves employed to downplay Bulger’s crimes not only served to make Bulger appear less bad but, more important, provided a way around the bureau’s guidelines requiring a strict evaluation of any unauthorized criminal activities. If a complaint or tip against a prized FBI informant could be rendered too vague or unreliable, then there would be nothing solid for the FBI to pursue. Morris and Connolly could then continue to pay lip service to the guidelines—offering assurances that if they ever did get a hard and fast tip against Bulger they would certainly perform their duty and run it down.

But somehow, in their hands, tips regularly turned to sand. It was a pattern Connolly established early on in the way he parried the vending machine executives who complained to the FBI that Bulger and Flemmi were shaking them down, and again, in the way the extortion of Francis Green fizzled once the matter landed in the FBI’s lap.

The new challenge in the early 1980s was what to make of the information other FBI agents were gathering from their own informants about Bulger and Flemmi’s widening criminal empire. The gangsters, said one informant, were taking over gambling operations in communities surrounding Boston. In early 1981 yet another informant reported that “James Bulger, aka Whitey, is a known bank robber and is trying to finance the funds from bank robberies into gambling activities.”