Black Mass

In the days following the incident Connolly did not document the episode in any FBI report. He did not notify the two FBI and state police field managers of Operation Lobster who were responsible for the safety of “Nick Giarro.” Connolly told Morris about it, and the Flemmi tip was transformed as it was passed along, just as in the child’s game of telephone, deepening in seriousness from a possible shakedown to a threat of murder. The more they talked about it, the more they dramatized the idea of a heart-pounding, midnight scramble that resulted in saving an agent’s life, the more they now had in hand a profound illustration of the importance of the deal they had with Bulger and Flemmi. The “accidental tip” that began with Flemmi seemed suddenly to capture the essence of why Connolly and Morris had to do what they could to keep Bulger and Flemmi for the FBI.

AS 1978 came to a close, the FBI handler and the FBI supervisor had a big problem looming on the horizon: the gathering storm of the race-fixing case. Instead of fizzling, the case building around Fat Tony Ciulla had taken off. For Howie Winter, Ciulla was turning out to be the biggest insult to a string of injuries he and his gang had suffered. In a state prosecution, Winter had been convicted of extortion and was sitting in a Massachusetts state prison as Ciulla was unloading before the federal grand jury in Boston. Hit by a run of huge losses in his New England sports-betting operations, Winter had actually gone to see the Mafia’s Gennaro Angiulo before his incarceration and borrowed more than $200,000.

The November 6, 1978, issue of Sports Illustrated featured a cover story about Ciulla and his life in crime as the “master race fixer.” The newly minted government witness was paid $10,000 by the magazine for the long piece, which mentioned the ongoing Boston probe. Down in Mt. Holly, New Jersey, Ciulla was busy walking through a dress rehearsal of sorts for the upcoming Boston case, testifying as the key witness at a local trial against nine jockeys and trainers.

It all worried John Connolly. He didn’t care about Howie Winter, but he cared about Bulger and Flemmi. In a sense, the New Jersey trial was not the immediate threat. That trial involved only the jockeys. But Ciulla’s role in the New Jersey trial was nonetheless making life in Boston miserable. Testifying against the jockeys, Ciulla was talking publicly for the first time about how the race-fixing scheme worked. During the same weeks when Connolly was scrambling with information he’d gotten from Bulger and Flemmi that might affect undercover agent Nick Gianturco’s safety, Fat Tony was providing a blow-by-blow account of who had done what to fix horse races that netted millions of dollars for the gangsters back in Boston. At one point Ciulla had been asked to identify his partners in Boston. Ciulla at first hesitated, like an actor setting up his best lines.

“Your honor, I have been in front of federal grand juries with these names. I don’t know if I am allowed to say these names here in open court.”

The local judge was unimpressed with Ciulla’s dilemma. “You are here now,” the judge replied from the bench. He ordered Ciulla to identify the key partners in Boston.

There was to be no holding back, and Ciulla didn’t.

“Fellows that were partners of mine,” he began.

“One’s name is Howie Winter.

“One name is John Martorano. M-a-r-t-o-r-a-n-o.

“Whitey Bulger.

“Stephen Flemmi.”

It was the end of 1978, and the much-anticipated Boston indictments in the federal race-fixing probe were being assembled. John Connolly and John Morris both decided they had to do something, even if Ciulla’s sworn testimony in another state had made any backstage maneuverings to guard Bulger and Flemmi all the more difficult to pull off.

FIRST OFF, Connolly and Morris huddled secretly with Bulger. The meeting was “off the books.” No report or memo was ever written up describing the January 1979 session. Connolly and Morris rendezvoused with Bulger at his apartment in South Boston, and the three talked through the case that had been constructed around Ciulla. “We thought we were going to get indicted,” Flemmi said about those tense days of early 1979.

To Bulger, his position was pretty simple. He told the two agents that he and Flemmi were not part of their gang’s race-fixing scheme. The government was in bed with a liar.

Bulger’s claim hardly came as a surprise to the FBI agents—a criminal target’s assertion of innocence was neither unique nor unusual. To cover his bases, Morris could have played hardball with Bulger. He could have insisted that Bulger and Flemmi execute a sworn affidavit attesting to their innocence. Doing so would have made the FBI look more responsible. If evidence ever surfaced showing Bulger to be the liar, the informants could have been prosecuted, at a minimum, for making a false statement to the FBI.

But Morris was not about to put Bulger and Flemmi through that kind of meat grinder. He “never gave that any thought,” he said. Bulger was a prime cut, not ground chuck. Instead, Morris and Connolly wholeheartedly adopted Bulger’s position—Bulger’s word against Ciulla’s—and promised to pursue the cause by seeking an audience with the chief prosecutor in the case, Jeremiah T. O’Sullivan.

Bulger was heartened when the agents said they would go to bat for him. He immediately told Flemmi they were off the hook. Bulger explained that “John Connolly had told him that we would be taken out of the case and we would not be indicted.” It was music to Flemmi’s ears.

Within days Morris and Connolly were crossing the few city blocks separating their FBI office in downtown Boston at the John F. Kennedy Federal Building and prosecutor O’Sullivan’s office on the upper floors of the John W. McCormack Courthouse in Post Office Square. O’Sullivan was not pleased to be taking up a matter like this so late in the game. The intense prosecutor, a bachelor in his midthirties, was all business, nearly all of the time. To many lawyers who went up against him he came off as a self-righteous zealot. But to his associates he was a relentless crime fighter, even if humorless and demanding. He’d grown up in a three-decker in nearby Cambridge, graduated from Boston College and Georgetown Law School, and was determined to work his way through the ranks of local organized mobs until he reached his ultimate ambition, nailing the Mafia.

By the time Morris and Connolly walked into his office, the finishing touches were being put on indictments in the race-fixing case, and at that point Bulger and Flemmi were indeed in the mix of the nearly two dozen figures facing arrest. This was hardly the right time—the final days of a two-year investigation—to come asking for favors.