Black Mass

Almost a year to the day after the North End meeting with Callahan about murdering Wheeler, Halloran talked nonstop to the FBI, from January 3 to February 19, 1982. He moved between three safe houses as the agents pressed him for corroboration that proved elusive. They had Halloran wear a wire, but that was unproductive—the wiseguys always seemed to know when he was coming. They demanded a polygraph, which Halloran refused. The Halloran debriefing became a stalemate, with agents believing his basic story but demanding more proof than Halloran could provide.

HALLORAN became part of Bulger’s bitter legacy within the FBI when agent Leo Brunnick went to the ever-approachable Morris and asked him for his “take” on Halloran’s tale. Morris instantly realized that Halloran’s story posed a dire threat to the unholy alliance with Bulger. It was against FBI policy to retain an informant who was also under investigation by the bureau. Morris quickly disparaged Halloran’s credibility.

While Halloran dangled in the breeze and shifted from one safe house to another, Morris told Connolly that Bulger had been accused of being part of the Wheeler murder. Morris fully believed Connolly would tell Bulger about the danger to him. Although Morris knew that dire consequences could follow his tip-off, he claimed he felt they were unlikely because Halloran’s account probably wasn’t true.

It got worse. Jeremiah O’Sullivan was the prosecutor whom pro-Halloran agents needed to get the Winter Hill snitch safely off the street. If he gave the okay, approval would become a routine matter up the line. But O’Sullivan became obdurately against giving Halloran a new identity in a new community to protect a witness with a story to tell. To him Halloran was a problem not worth having. O’Sullivan had taken a coldhearted look at the issue and decided there was simply not enough corroboration available to make a case with Halloran. Indeed, Halloran was not an easy call. It was his word against Callahan’s, and he refused to take a lie detector test. He also had little success in developing other Winter Hill cases while wearing a wire.

But it was also clear that O’Sullivan was partially blinded by the tight nexus of considerations involved in his prosecution of the Angiulos. “Was he part of the protection of Bulger?” another prosecutor asked rhetorically. “Not consciously. He refused to give Halloran a break on a fresh murder charge without some corroboration of the story. In those circumstances, a reduced charge would be a tough one to swallow. I’m not sure what he could have done differently.”

Yet investigators working the Wheeler case say that O’Sullivan lost sight of the danger to an informant providing sensitive information on a major case. Several agents, according to Robert Fitzpatrick, the number-two man in the Boston FBI office at the time, became convinced Halloran could be killed if he was not enrolled in the witness protection program.

Fitzpatrick took his concerns directly to O’Sullivan but hit a brick wall. “O’Sullivan wasn’t buying Halloran,” Fitzpatrick recalled. “To him Halloran was a wanna-be hyping a story, a drunk not worth the bother. I went back at him and said, ‘Look, my guys are coming to me and saying, ‘Get him off the street. He’s in danger.’ He said, ‘We’ve talked about this, and I’ve heard what you said, and I’ll let you know.’ That means no.”

By May 1982 Fitzpatrick felt so strongly about the danger to Halloran that he went over O’Sullivan’s head to the newly appointed U.S. attorney, William Weld. “I told him, ‘Hey, this guy could get shot. Agents are telling me about it. We need to do something.’” Years later Weld confirmed the Fitzpatrick visit. “Fitzy said to me, ‘You know, people always say there’s danger for this snitch or that snitch. They may be killed for cooperating. I’m telling you this guy—I would not want to be standing next to this guy.’” But Weld did not intervene with O’Sullivan, who had been something of a mentor to Weld when he first took the top prosecutor’s job.

Toward the end of his debriefings Halloran learned that Whitey Bulger was an FBI informant. Panicking, Halloran suddenly felt that he had nowhere to turn, that he was in danger on the street and even at the FBI office. “This really was the gang that couldn’t shoot straight,” said Halloran’s disgusted cousin, Maureen Caton. “It just slips out one day that, ‘Oh, by the way, Bulger’s an informant.’ Forget Waco. Just look at what happened to Brian Halloran.”

The upshot was that the unfocused and terrified Halloran was left on his own to move furtively through a hostile landscape while the two FBI squads chafed against each other over his fate. The agents who developed Halloran found themselves fighting a rearguard action against Connolly, who had dismissed Halloran’s lurid account as self-serving prattle from a dirtbag. Although the agents who sided with Halloran had some doubts about his precise role in the crimes and plots, they firmly believed that Bulger was in their sights and Halloran was their ticket. The fight quickly intensified. Connolly was accused by two agents of rifling their files about Halloran, and the exasperated Fitzpatrick was forced to secure the material in his office safe.

In fact, Fitzpatrick recalled, Connolly never really denied looking over the shoulders of other agents compiling information on Bulger. Connolly just stuck his jaw out, saying, “Either you trust me as an agent or you don’t. He’s my guy, and I need to know what he’s up against.”

According to Fitzpatrick, Connolly proceeded to set up an interview of Bulger and Flemmi about the Wheeler case. In a departure from standard techniques, the pair were interviewed together; as a result, investigators lost the chance to play contradictions in their accounts against each other. The interview went nowhere and was filed away.

BY THE spring of 1982 Halloran’s life had became a daily ordeal of constantly checking the rearview mirror and looking over his shoulder. He couldn’t go home to his wife and young son because he was afraid the door would be kicked in and a machine-gun burst would kill them all. His father and an uncle paid the rent and brought the weekly groceries to his wife.

After several weeks of lying low, with his wife in the hospital about to deliver their second son, Halloran got a call, according to his family, that his sister living near the South Boston waterfront wanted to see him. A friend drove him into Southie, a place he had been avoiding. Around 6:00 P.M., while Halloran and his friend were parked outside a restaurant, a car containing Bulger and Flemmi pulled alongside Halloran’s Datsun. There were some shouted words and then two shots rang out. Then a fusillade. Halloran staggered free of the car and fell in the street. One of the assassins raced up to him and shot him several more times. He died with twelve bullets in him from two guns. It had all the firepower and finality of a Bulger-Flemmi execution. And it even included a telltale swerve from Stevie Flemmi. He met with agent Connolly the day after the murder, and Connolly filed a fast report saying that Charlestown gangsters may have been behind Halloran’s death.