Black Mass

Bulger and Flemmi had notified “salesmen” from their company about potential sites, and the salesmen had then paid visits to the bars and restaurants to explain why each establishment ought to install their company’s vending machines. It was a fairly persuasive pitch that included the muscle of a certain kind of underworld name recognition. “They would use our names,” Flemmi said.

The Melotone matter found its way to handler John Connolly.

After huddling with Bulger, Connolly set up a meeting with the executives from Melotone to outline for the company officials the hard-core truths about pursuing a criminal case. The agent told them they could certainly go after Bulger and Flemmi; that was their legal right. But he asked them if they’d really thought the whole thing through. Did they understand what it meant to testify against the mobsters? The disruption to their lives, even the risk to their families’ safety? “He painted a very bleak picture to them,” Flemmi recalled.

Connolly also told the company men their lives might be in danger. “If they wanted to prosecute, he was willing to, you know, to prosecute us,” Flemmi recalled. “But he said that they’d have to go into the witness protection program because of who we were.”

John Connolly’s grim forecast had its desired effect. Soon, said Flemmi, “they backed off.” Connolly even worked out a compromise. He promised the executives he’d arrange for Bulger and Flemmi to concede a bit. “One location was in question,” said Flemmi. “The machine came out of the place. Their machine stayed in place. . . . There wasn’t any problem after that.”

No harm, no foul.

It was unorthodox, but, to Connolly, why not? He’d negotiated something akin to an out-of-court settlement. No one had gotten hurt. And if the complaint evaporated into thin air, there was nothing for the FBI to investigate. Just as important, there was no reason to conduct any kind of internal review at the Boston office of Bulger and Flemmi. And certainly no reason to bring headquarters into it. The requirement in the guidelines that an informant’s crimes be reported was not even triggered. Connolly had found a way to protect the deal.

“He didn’t want to see us get indicted,” Flemmi explained, and the FBI culture provided Connolly with the room he needed to improvise; he could talk the talk of the manual but also make up his own lines along the way.

Five months after Whitey Bulger was opened up as an FBI informant, Connolly succeeded, on February 2, 1976, in having him elevated to top echelon status. The Boston-bred agent now had two “TEs” in hand, Bulger and Flemmi. Flemmi, once “Jack from South Boston,” became known as “Shogun.” Bulger was “Charlie.”

But cracks—small fissures, but cracks nonetheless—began to show. “Connolly fashioned himself as a very important guy,” recalled Robert Fitzpatrick, a seasoned agent who became an assistant special agent in charge (ASAC) of the Boston office in the early 1980s. He always seemed to be moving around the city working people in the media, in politics, and at the office. He became the go-to guy for Red Sox tickets. On occasion Connolly failed to make the mandatory morning sign-in. His manner began to change, and his style became more charged. He began to operate like a salesman—skilled at feigning sincerity but uninterested in the real thing. It was the consummate skill of a great pretender, a skill that became his hallmark.

And he’d apparently outgrown his marriage. John and Marianne Connolly separated in early 1978. He promptly relocated to an apartment in Quincy just a few blocks from the beach road where he’d met with Bulger that moonlit night. The apartment was also practically across the street from the Louisburg Square condo complex where Bulger bunked with Catherine Greig, the younger of his two girlfriends. But for Connolly, Quincy was part of a journey, not a destination. He began thinking about moving back into Southie.

Fitzpatrick was one FBI manager who began having reservations. He and Bulger and Connolly had a secret meeting, a rendezvous that was part of a required, periodic supervisory check of an FBI handler and informant.

“I let him bullshit,” recalled Fitzpatrick, about how Bulger immediately took control of the session. Bulger talked about his weight lifting, the good shape he kept himself in.

“He did a lot of talking. He did a lot of bragging—what I would consider bragging—about how strong he was, what he was doing in prison. He told me about his background. We talked about Southie. And generally speaking, it was my impression that he was trying to impress me.”

After the meeting, Connolly told his FBI boss, “Isn’t he a great fuckin’ guy?” Fitzpatrick never forgot agent Connolly’s line. Bulger, the reputed killer, loan shark, and drug trafficker—a great fuckin’ guy? Fitzpatrick blanched.

IN AN office where some agents had their doubts, managers took comfort in the December 1977 promotion of another agent to oversee Connolly. The new supervisor of the Organized Crime Squad, veteran agent John Morris, was viewed as a good match for the savvy street agent, a straight-arrow supervisor who could serve as counterpoint.

The two paired off like an odd couple. Connolly was gregarious, tall, and dashing. Morris, a man of midwestern origins, was quiet and plain-looking. Connolly was a free man moving about the town. Morris was married, with a family. He lived in the suburbs, often commuted to work with Dennis Condon, and was considered a smart, capable manager whose paperwork was thorough and of high quality.

But over time Morris would himself turn out to be the polar opposite of a role model. The FBI brass had made a horrible mistake. The intense, thin-lipped Morris was no match for all that was brewing inside the Boston office of the FBI. The deal between Connolly and Bulger and Flemmi was going to turn out to be bigger than Morris could handle—bigger than any subsequent supervisor, or even the FBI itself, could handle.

CHAPTER FIVE

Win, Place, and Show
The third race at the Suffolk Downs racetrack was set to go according to script. The Winter Hill gangsters were standing by in Somerville in eager anticipation. Led by Howie Winter, and including associates Whitey Bulger and Stevie Flemmi, they had placed thousands of dollars in bets at both the track in East Boston and with bookmakers.

Time to sit back and smell the roses.

But something was wrong. One jockey, who’d been paid $800 to do his part, had decided to improvise. Instead of holding his horse out of the running, he’d raced hard to the end. Bets had been made, and now money had been lost. Howie Winter was not happy.