Black Mass

A Boston detective at the murder scene claimed that the dying Halloran was able to identify Charlestown gangster Jimmy Flynn as his killer. Flynn had the motive, according to police, because he and Halloran were two Winter Hill gang members who never got along, particularly after Flynn learned that Halloran had ratted him out on a bank robbery. Flynn went into hiding and was not captured until two years after the murder. In fact, he was not at the murder scene. Investigators concluded that Flynn was a patsy set up to send police in the wrong direction. Halloran’s murder was a case of Bulger doing his own dirty work, a rare instance when he stepped out of the shadows to pull the trigger himself.

Ironically, after the Halloran murder, the discord within the FBI office abated, with agents from the two squads only occasionally glaring at each other in the back of an expansive room. It was like a dysfunctional family papering over incest. An informant had been killed, and agents began to live with the embarrassment.

At the same time the office leadership fell into a resigned torpor about Bulger. The agent in charge, Larry Sarhatt, had gone from being a new man determined to get to the bottom of Lancaster Street in 1980 to a harried boss looking forward to retirement after twenty years in the bureau.

As one by-product of the Boston office’s effort to smooth over internal strife, upper management became permanently hobbled by the Bulger dilemma. For the most part, the managers didn’t entirely trust Connolly. But no one wanted to deal with the institutional grief involved in taking him on. Connolly might be too close to an informant, but it wasn’t worth a brawl. It happens.

“Connolly just became a force unto himself,” Fitzpatrick said, “a vortex in a constantly changing system. He stayed put as new agents in charge came and went. And he could take care of other agents. He became the guy who could get you sports tickets. He could help you get a day off through the secretaries. He made no secret that he could help you get a job after retirement through Billy Bulger. But he just wasn’t much of an agent. He couldn’t write a report. He was no administrator. He was just this brassy bullshit artist. We enabled him to some extent. No one had the stomach for examining what he was up to. We just never came to grips with that guy.”

But the Halloran episode lingered in Morris’s mind. Although he had rationalized his passive role in Halloran’s demise, he knew exactly what had happened. Later, during a back-channel tip-off to Bulger and Flemmi that one of their bookies was being targeted by other FBI agents, Morris felt compelled to warn the pair against murder. Stay away from the bookie, Morris said. No more bloodshed.

Morris had reason to fear the worst. He knew what had happened to Wheeler and Halloran. And he had firsthand experience in the fate of another underworld figure who ran afoul of Bulger. Arthur “Bucky” Barrett was an expert safecracker who got caught in the no-man’s-land between the bureau and Bulger. He had pulled a daring bank heist in 1980, working with five others to rifle safety deposit boxes of $1.5 million in cash. Shortly after the robbery Morris and Connolly were put on to Barrett by Bulger. The agents approached the safecracker with an off-the-books double mission: they wanted to soften him up for Bulger with a friendly “warning” that Whitey would be looking for a cut from the bank job. And then they offered him the perilous haven of the FBI informant program if he would become a snitch. It was a mission of staggering corruption. Here were two seasoned FBI agents acting as Whitey Bulger’s emissaries on the street.

Nevertheless, Barrett rejected the FBI overture. And even though Barrett paid much of his bank withdrawal to placate Bulger, it did not save him from being kidnapped, tortured, and dragged into the cellar of a South Boston home in 1983, never to be seen alive again.

But Bucky Barrett was an anonymous casualty of war. He simply disappeared, and no one misses a safecracker except his wife and kids. It was Brian Halloran’s dead body on Northern Avenue that left a deep mark on agents in the Boston office. Fitzpatrick looked back on it and felt “defeated by it all. I still think about it and fight off the ghosts.”

TULSA homicide detective Michael Huff, the first officer on the Wheeler murder scene in 1981, had learned quickly that John Callahan and the World Jai Alai business were probably behind the killing and that the Winter Hill gang was in the picture. But he could get no hard information out of Boston. Phone calls went unreturned, and conferences were canceled or rescheduled. The Massachusetts State Police told him that Winter Hill was probably involved, but Huff could not induce the FBI to help him get background information on gang members. He never heard the name Bulger until Halloran was dead.

Callahan was the early focus for Huff and some Connecticut State Police detectives who had been chasing the accountant with the double life for several years because of the swirl of dust around the jai alai outlet in Hartford. They began looking into Callahan’s finances and the company books for irregularities that could be used to pressure him to talk about Wheeler’s death. Detectives had even gone to Switzerland to check his accounts and recent stay there. With investigators from two states rummaging through his books, Callahan became chillingly aware that he was now the last person alive who could implicate Bulger on the murder.

The former driving force of World Jai Alai was clearly in the crosshairs. But the pursuit of Callahan as a suspect ran into the usual detour in Boston. When Callahan first came into view as a suspect in late 1981, Huff began working with the Tulsa FBI office, which sought information about Callahan’s Winter Hill associates from none other than John Morris. In response to the queries from Tulsa, Morris sent Connolly to question Callahan. A defensive Morris later argued that Connolly was the “absolutely logical choice” to ask Callahan if Winter Hill was involved in the Oklahoma murder. Not surprisingly, Connolly reported back that Callahan had no dealings with Winter Hill and that Bulger had nothing to do with the Wheeler hit. One more time Connolly said Whitey didn’t do it. Morris obligingly closed the file.

The quick action confused Huff. He could understand there being no hard information available, but case closed? It burned him up that Wheeler’s death didn’t strike a chord in Boston. Wheeler was a “big damn guy” in his town who hired hundreds of people and gave money to good causes. Something’s wrong here, he thought. Why won’t anyone talk straight to me about a broad daylight murder of a prominent businessman whose family deserved some answers?

Huff and his new colleagues in Connecticut did the only thing they could do—they pushed on, scratching their heads about what was going on with the bureau in Boston. Their focus shifted to the Miami outlet of World Jai Alai to develop incriminating information on Callahan. By July 1982 Huff and the other detectives felt they had gathered enough damaging financial material to pressure Callahan in person toward the end of July 1982. They headed down to Florida on August 1. But one of Callahan’s old drinking buddies, Johnny Martorano, was already there. When Huff and Connecticut detectives landed at Miami airport, John Callahan was dead in the trunk of his rented Cadillac in a garage at the same airport. The peppery Callahan, who liked drinking with wiseguys, died like one at age forty-five.