Black Mass: Whitey Bulger, the FBI, and a Devil's Deal by Lehr, Dick, O'Neill, Gerard (2012)

PART THREE

Some things are necessary evils,
some things are more evil than necessary
.

JOHN LE CARRÉ,
THE RUSSIA HOUSE

CHAPTER TWENTY

The Party’s Over

On a rainy winter morning in Boston, January 6, 1998, the judicial excavation into the FBI’s ties to Bulger and Flemmi finally began. “We’re here today,” the judge announced formally in courtroom number 5 in US District Court, to begin “hearings on the motions to suppress certain electronic surveillance and Mr. Flemmi’s motion to dismiss based on alleged promises that were made to him.”

The lawyers, standing, introduced themselves: Fred Wyshak, Brian Kelly, and Jamie Herbert for the government; Tony Cardinale, Ken Fishman, Martin Weinberg, and Randolph Gioia for the four mobsters. Off to the left side, under the watchful eye of federal marshals, sat the accused: first Frank Salemme, dressed in a gray, double-breasted suit and red tie; then Bobby DeLuca; Stevie Flemmi; and finally, to the left of Flemmi, hitman Johnny Martorano. They sat in silence. No one—not the mobsters, not the lawyers, not the judge, and none of the television, radio, and newspaper reporters who filled the benches in back—had any idea what was to come. Never before had the matter of the Boston FBI, Whitey Bulger, and Stevie Flemmi been the grist of open federal court proceedings.

It was now seven months since the government had obeyed the court’s order in June to identify Bulger as an FBI informant. But since that pivotal moment weeks and months had come and gone as the judge and the lawyers prepared for the hearings and argued over their scope and ground rules. The racketeering case was already almost three years old and still stuck in its pretrial phase. But by now all the parties had realized that nothing about the case would ever move quickly, as the judge moved ponderously into unknown legal terrain: the backstage, inner workings of the FBI.

In the months leading up to this moment, the Justice Department had been downloading to defense attorneys hundreds of pages of previously secret FBI files covering the FBI’s history with Bulger and Flemmi. Cardinale, Fishman, and the others devoured the documents. “We started to realize there were all kinds of new motions, including government misconduct,” said Cardinale. “We began to ask, ‘If Flemmi was an informant for that many years, how in the world can this indictment be any good?’”

For his part, Flemmi, having decided he had nothing more to lose, began filing sworn affidavits describing juicy details of his double life. It was the legal equivalent of flirting, revealing selective and sensational examples of FBI protection he claimed went to the heart of “informant defense.” In one, Flemmi said that Morris had promised him and Bulger they could commit any crime “short of murder”; in another, that the FBI regularly tipped them off to other investigations, including the timing of the 1995 racketeering indictment that he was now fighting to get booted out of court. By year’s end Fishman had refined the Flemmi defense, arguing that Flemmi had been “authorized,” mainly by Morris and Connolly, to commit many of the crimes for which he stood accused. Because the FBI had promised Flemmi “immunity,” he could not now be prosecuted for those crimes.

Wyshak, meanwhile, had staked out the government’s response to Flemmi’s various disclosures that now regularly made front-page headlines in the city’s newspapers. The actions of “rogue agents,” Morris and Connolly, Wyshak argued, should not undermine the racketeering case; any promises of protection they may have given Bulger and Flemmi were illegal and therefore could not possibly constitute anything close to legal “authorization.” Wrote Wyshak: “Extensive reviews of [FBI informant] files by the parties as well as by the Court have failed to unearth a single shred of objective evidence that Bulger and Flemmi were authorized to commit the crimes alleged in the indictment.”

It was a high-wire argument of sorts, as prosecutors sought to protect the evidence against the mobsters but, at the same time, acknowledge the stomach-turning corruption of FBI agents. Then, late in the year Morris was granted immunity in return for testimony that would buttress the government’s point of view; he would confess, on the one hand, to crimes and FBI misconduct, but, on the other hand, also testify that Bulger and Flemmi had never been given any formal immunity.

The two positions were reflected in the opening remarks that winter morning when the Wolf hearings finally began.

“The focus here is on the promises made to my client, Stephen Flemmi, by the FBI,” Fishman told the court. “In exchange for his very unique and special cooperation, he would be protected, he would not be prosecuted.”

Hogwash, replied Wyshak when his turn came. Bulger and Flemmi had never had any official deal guaranteeing they would not be prosecuted for their crimes. The defense attorneys, said Wyshak, were portraying Flemmi as if he were some kind of “Junior G-man with a license to kill.

“Isn’t that preposterous?” mocked Wyshak.

▪   ▪   ▪

But of course it wasn’t so preposterous after all.

In the months to come Fishman and Cardinale may not have been able to uncover a paper trail showing a formal promise of immunity, but they showed that the Boston FBI was a House of Horrors when it came to Bulger and Flemmi—that agents coddled, conspired, and protected the mobsters in a way that for all practical purposes had given them a license to kill.

Right from the start Wyshak and Wolf tangled, and the tension between the prosecutor and the judge erupted regularly as Wyshak fought Wolf on the range of the questions put to government officials and the growing pile of government files that were being unsealed. It wasn’t as if Wyshak was trying to cover up FBI corruption—by now he was overseeing an active investigation of Connolly and others—but he opposed Wolf’s approach to staging a court inquiry that, to Wyshak, seemed without limits and restraints.

“You might as well put the whole file in!” Wyshak barked at the judge just two days into the hearings, on January 8. “Why don’t you just put the whole file in?”

“Why don’t you just sit down, Mr. Wyshak?” Wolf said.

Wyshak would not, and he continued arguing against allowing a new batch of FBI files to be made public.

“Have a seat,” Wolf interrupted.

“What is the relevance?”

“Have a seat.”

Wyshak remained standing.

“Do you want to be held in contempt? Sit down!”

The hearings lasted most of 1998. The testimony of the forty-six witnesses filled seventeen thousand pages of transcripts, and 276 exhibits—mostly lengthy internal FBI documents—were admitted into evidence. Taking the stand and swearing to tell the whole truth were a former Massachusetts governor and US attorney (William Weld); a sitting Superior Court judge and former protégé of prosecutor Jeremiah T. O’Sullivan (Diane Kottmyer); the three FBI supervisors who ran the Boston office during the Bulger years (Lawrence Sarhatt, James Greenleaf, and James Ahearn); and a long line of federal drug agents, other FBI supervisors, and many of the FBI agents who’d worked alongside Connolly (Nick Gianturco, Ed Quinn, and John Newton). It was a who’s who of the federal law enforcement establishment, and there was a touch of the surreal as former FBI agents on the witness stand sometimes seemed to mimic tactics usually displayed in court by the gangsters they pursued.

The godfather of the FBI’s Organized Crime Squad, Dennis Condon, the retired supervisor who had first matched Connolly, Bulger, and Flemmi together back in the mid-1970s, took the stand in early May and eluded tough scrutiny. The lawyers were hoping he would shed light on the early years of the FBI and Bulger, but Condon pleaded a blank memory. He set the standard for responding, “I don’t recall.” Even when an attorney showed him an FBI document he’d prepared, Condon would shrug, say he didn’t recall writing it, and was therefore unable to elaborate further. Cardinale and the other attorneys were left rolling their eyes, exasperated.

Jeremiah T. O’Sullivan eluded scrutiny altogether. In late February the fifty-six-year-old former prosecutor suffered a heart attack, was hospitalized, and had an adverse reaction to medication. Facing a lengthy rehabilitation, he was spared sharp questioning about removing Bulger and Flemmi from the horse race–fixing case in 1979. O’Sullivan would also have been grilled on claims he’d made publicly and to government investigators that his hands were clean because he’d never even known Bulger and Flemmi were FBI informants. The evidence to the contrary was substantial, and defense attorneys had been eager to put O’Sullivan on the hot seat.

The missing prosecutor quickly became a target of dark courthouse humor. Lawyers and commentators couldn’t resist suggesting that the heart attack enabled O’Sullivan to assert a claim many mafiosi had tried to pull off—too ill to testify. In fact, a fiery O’Sullivan, back in the mid-1980s, had aggressively fought Mafia enforcer Larry Zannino’s medical claim that he was too sick to come to court. The prosecutor forced Zannino to appear, even though he was in full medical regalia, strapped into a wheelchair and breathing from an oxygen tank. Now people began to joke that O’Sullivan had “pulled a Zannino.” Though by the end of the hearings O’Sullivan would recover and resume his private law practice at one of the city’s prestigious, old-line firms, Choate, Hall & Stewart, the man who for sixteen years had fought the Boston Mafia never once took the stand.

Teresa Stanley was granted immunity and compelled to testify about her life with Whitey Bulger—and his getaway when the 1995 indictment came down. In a soft voice the blue-eyed fifty-seven-year-old, with snow-white hair and dressed in an orange floral top and black slacks, described how she and Whitey had been an item for nearly three decades. She’d cooked dinner for Bulger at her South Boston home nearly every night, and he’d spent most holidays with her family. Stanley spoke about mysterious trips to Europe. She didn’t ask Bulger why they were just moving about because such questions always ended in an argument. She recalled their hasty drive around the country—to Long Island, to New Orleans, where they spent New Year’s Eve, to Graceland in Memphis, and to the Grand Canyon. Bulger made lots of calls from pay phones, but she didn’t ask who he was talking to or what the calls were about. Stanley also testified that Bulger ultimately abandoned her for the much younger Catherine Greig, who he’d been seeing secretly for twenty years.

“He was leading a double life with me,” a spurned Stanley concluded, “and a double life with the FBI.”

Unsealed in court were FBI reports revealing that Flemmi had ratted on Salemme for three decades. Flemmi was quoted in one FBI report as calling Frank Salemme “a jerk.” After hearing this, Frank Salemme moved, making sure DeLuca sat between himself and Flemmi. Cadillac Frank’s affection for Stevie evaporated; indeed, Salemme became “just sickened by the sight of him,” Cardinale concluded. The FBI files also clearly showed that Bulger and Flemmi had informed on Howie Winter and other Winter Hill gangsters, including Johnny Martorano, who, like Salemme, began pulling away from Flemmi in the courtroom.

Throughout, Flemmi tried to keep up his game face, coached that his only hope for freedom was to have all this surface to prove the FBI had promised not to prosecute him.

“To be in court every day with a smile on his face,” Cardinale remembered, “it’s crazy. I mean, one day I just got through telling the judge what a murderous piece of crap I thought he was, and he called me over. I thought he was going to say something to me, like, you know, ‘Don’t you ever say things like that about me again.’ He calls me over and he says, ‘Jesus, you’re doing a great job.’ It’s like, whoa! That’s all I can think: I-yi-yi-yi-yi. I mean, it’s not even registering here. I had just literally gotten through saying he’d killed, you know, Halloran, that he’d done all kinds of horrendous, diabolical, murderous things, and I thought, Ohmygod, I went too far, he’s going to say something, and he says, ‘Look, you’re doing a good job.’”

▪   ▪   ▪

The unfolding debacle for the FBI hit rock bottom when John Morris walked into court and began testifying on April 21. In the months leading up to the hearings Morris had negotiated immunity with the prosecutors for the crimes he’d committed. During the private debriefing with FBI agents and prosecutors that accompanied those negotiations, he wept. He’d thrown his career away by getting too close to Bulger, and he knew it. Now on the witness stand for eight grueling days, a wasted Morris sought to project the composed manner of an aging monsignor as he matter-of-factly described his descent from agent to liar and criminal, confessing to taking Bulger’s money and obstructing justice by warning Bulger about investigations.

Going back to the 1970s, when the unholy alliance was forged, Morris recalled a “time frame” of “intense pressure on agents to have informants” against the Mafia. “There was a lot of pressure,” he testified. He talked about how he teamed up with John Connolly and, together, they rode Bulger and Flemmi to stardom in the Boston FBI office as the master agents in the war against the Mafia, even if, in truth, the ride was a free fall into hell. Morris rued the day he hitched his star to Bulger, Flemmi, and Connolly and ended his professional life in Boston in fear of both Bulger and Connolly—Whitey because of his hold on him through the $7,000 in bribes he’d taken, and Connolly because of his network of political allies, most notably Billy Bulger.

Despite defense attorneys’ relentless effort to get Morris to concede that he’d promised Bulger and Flemmi immunity from prosecution, Morris disagreed. He admitted he’d leaked investigations, but that hardly constituted a grant of immunity. He testified he didn’t have the authority as a supervisor to confer immunity on the mobsters. “Immunity was a very formal process, and there’s actual documentation,” he said. There was none for Bulger.

Toward the end Morris began to wobble. Following questions about yet another instance where his shady work with Bulger may have cost a man his life, one of the defense attorneys suddenly departed from the set sequence of questions. Turning to Morris, the lawyer catapulted to a higher meaning, demanding to know what Morris could have been thinking all these years: did the FBI’s crusade against the Mafia justify the Bulger evil? “Do you agree that your conduct as an FBI agent in connection with Mr. Bulger and Mr. Flemmi was consistent with that concept, that the end justifies the means?” Brought up short, Morris sagged noticeably, and he struggled to regain his monsignor’s placid demeanor. He sighed and looked sadly off to the side.

“I’m not certain of that,” he testified softly.

By the end there was nothing left except for Morris to acknowledge the part he’d played in all that had gone wrong. Urged by defense attorneys to explain “more fully for us” how he was compromised, Morris said that he “had violated standards, integrity, rules, regulations.” Was John Connolly part of that process of compromise?

“I felt that he participated in it,” Morris replied, “but I accept responsibility for my own actions.”

▪   ▪   ▪

The shocking confessions made headlines, and about this same time John Connolly began to speak out—not in court but outside of court to reporters. From the sidelines the retired agent, now fifty-seven and still working as a lobbyist for Boston Edison, began offering sound bites to rebut the testimony given under oath before Judge Wolf. Each time a retired agent or government official took the stand and provided testimony that in any way criticized him, Connolly would sound off and call the witness a liar. So, for example, when retired FBI supervisor Robert Fitzpatrick testified that agents complained about Connolly “rifling” their files to find out what they had on Bulger, Connolly reacted, “That’s ludicrous.” Connolly angrily told reporters that Fitzpatrick’s testimony was nothing more than “unmitigated nonsense.”

The list of “liars” grew and grew. But Connolly saved his best lines for Morris, whom he began calling “the most corrupt agent in the history of the FBI.” Each day after Morris finished testifying, Connolly would condemn his former friend and supervisor. Morris may have only met with Connolly, Bulger, and Flemmi a dozen times over the years—while Connolly saw the mobsters hundreds of times—but Connolly insisted that he himself was a model FBI agent who’d never broken a single rule. All of Morris’s wrongs, said Connolly, “he did that on his own.”

Talking about the difficulty of the job he’d performed so well, Connolly said that handling informants was “kind of like a circus,” and “if the circus is going to work you need to have a guy in there with the lions and tigers.

“That was me. I was no John Morris, back in the office with a number 2 lead pencil. My job was to get in there with the lions and tigers. And I am no liar like Morris.”

Near the end of Morris’s testimony Connolly even made a brief court appearance. Having teamed up with a prominent defense attorney, R. Robert Popeo, Connolly strode into the courthouse in an expensively tailored suit and brushed past throngs of TV cameras and reporters saying he wanted to clear his name. He was a hero, not a villain, and now this band of prosecutors led by Fred Wyshak was out to bust him. He’d become the government’s scapegoat, a victim of runaway prosecutorial rage, when the truth of the matter was that he was a highly decorated FBI agent who’d done nothing wrong. “The proof is in the pudding,” Connolly said, defending the Bulger deal. “Look at the decimated New England Mafia.”

Then, standing in court on April 30 before Judge Wolf, the lawyer Popeo explained that unless Connolly was granted immunity from prosecution—like John Morris—he would not let his client testify. He would not allow Connolly to be “blindsided” when the government had made it known that Connolly was under investigation. Connolly then asserted his Fifth Amendment privilege against self-incrimination, walked outside, and resumed a tirade against Morris, who was still inside waiting to wrap up his eight days of testimony.

“I made him look away,” Connolly said of Morris. “He couldn’t even look me in the face.”

The Connolly sideshow continued into the summer, and a pattern developed: an affronted Connolly would issue heated public denials to any witness’s incriminating words. He disputed most of former supervisor Jim Ring’s testimony, particularly Ring’s account of the concerns he’d had for the “stupid” way Connolly met Bulger and Flemmi for dinner. Connolly wasn’t the only one in denial. Billy Bulger, now retired from politics and the president of the University of Massachusetts, joined the Connolly chorus after Ring in court told about Billy Bulger dropping in on one meeting. “I never met the man,” Billy Bulger said about Ring. “It never took place, but the business of denying such things is to make it appear as if something sinister had happened.”

By midsummer Massachusetts Representative Martin T. Meehan announced plans to hold congressional hearings into the FBI’s long affair with Bulger, saying the revelations tumbling out in the federal courthouse in Boston raised concerns about “establishing, maintaining, and monitoring relationships between agents and informants.” But like much of the nation’s business during late 1998, the inquiry was soon pushed aside by President Clinton’s impeachment.

Eventually the Wolf hearings even changed locations, from the building in Post Office Square, which had housed the federal court for sixty-five years, to a new $220 million facility overlooking Boston Harbor, an area known as Fan Pier, right in South Boston.

The hearings were shut down for a recess in July, and by the time they resumed in early August a key participant was absent. Frank Salemme took his seat next to Bobby DeLuca, and next to DeLuca sat Stevie Flemmi. But Johnny Martorano was gone. He’d heard more than he could take. He’d sat grim-faced as agents, cops, and officials testified about Bulger’s deal. He’d listened to how the FBI protected Bulger and Flemmi from the 1979 horse race–fixing case while the rest of the gang, including Martorano, were indicted. He’d learned that after fleeing to avoid arrest and living on the lam in Florida for more than a decade, he’d been found by the FBI because Bulger and Flemmi told the agency where he was. Disgusted, Martorano agreed to cooperate with prosecutors against Bulger and Flemmi. Quietly, he was moved out of cellblock H-3 in the Plymouth County Correctional Facility on Thursday, July 20, 1998, where he’d been kept along with the others, and was ushered to a secret “safe house” for a debriefing. Martorano was busy telling investigators about the murders that he, Bulger, and Flemmi had committed that had long gone unsolved. The defection shook up Flemmi.

Nevertheless, even after months of the FBI testimony, the colorful Connolly sideshow, and Martorano’s sharp reversal, only when Stevie Flemmi took the witness stand did the lengthy hearings finally reach a climax. His back against the wall, he’d launched the “informant defense,” and he had to persuade Judge Wolf that the government had promised not to prosecute him. It was tricky business whenever a criminal defendant took the witness stand, and in these pretrial hearings Flemmi and Fishman wanted Flemmi to go into deep detail about his deal with the FBI while avoiding admissions to any crimes—except crimes he insisted were approved by the FBI.

▪   ▪   ▪

Flemmi usually wore a black-and-white nylon jogging suit to court. But on the day he took the stand, August 20, 1998, the bespectacled crime boss wore a crisp, white shirt and maroon tie under a gray, herringbone sport jacket.

“Mr. Flemmi, it may be easier if you pick that microphone up a little,” the judge instructed a few minutes after Flemmi had begun his testimony.

Flemmi adjusted the mike. “How’s that, Judge?”

“And pull the seat a little closer.”

Ken Fishman, handling Flemmi carefully, opened right where it mattered most to the defense—at the dinner at John Morris’s house in the spring of 1985, during which, Flemmi said, Morris had promised that the gangsters could freely commit any crime “short of murder.” Fishman walked Flemmi through his history of the work he and then Bulger did with Paul Rico, John Connolly, John Morris, and Jim Ring. Throughout, Flemmi, at Fishman’s encouragement, emphasized the protection the FBI promised—a central tenet to the deal from day one.

“It was one of our themes: how much protection do we have? We’ve always stressed that, and they’ve always answered that in the affirmative, that we were protected, we wouldn’t be prosecuted,” Flemmi said just minutes into his first day on the witness stand. “We insisted on it. We wouldn’t be involved if we weren’t protected. It’s common sense. I wasn’t proud of it, and I wanted assurances. And with that I can speak for Mr. Bulger.”

There were times when Flemmi even waxed patriotic. “I believe I was performing a service for the United States government in my role as an informant,” he told Fred Wyshak once the prosecution’s turn came to ask the questions. Flemmi said he and Bulger had helped the FBI “to destroy the LCN, and I believed whatever I was doing I was doing in the interest of the United States government.”

The government’s chief prosecutor winced.

“Do you think it was in the interest of the United States government to control the flow of drugs into South Boston?” he asked. “Is that what you think, Mr. Flemmi?”

“I’ll assert the Fifth on that.”

Wyshak was no friend of Flemmi’s. The two sparred for hours over Flemmi’s “public service” as an informant.

“You had a good deal going,” chided Wyshak, pushing Flemmi to cut the phony high-minded spin. “You were committing crimes at will, putting money in your pockets, and, in your view, being protected from prosecution?”

FLEMMI: You’re forgetting one thing, Mr. Wyshak. The LCN was taken down. That was their [FBI’s] main goal. They were completely satisfied with that. We fulfilled our bargain.

WYSHAK: Did you think, Mr. Flemmi, that you and Mr. Bulger single-handedly took the LCN down?

FLEMMI: I’ll tell you something, Mr. Wyshak, we did a hell of a job.

WYSHAK: That’s what you think?

FLEMMI: I think we did. The FBI thought we did.

WYSHAK: And when the FBI did that, you and Mr. Bulger were top dog in town, weren’t you?

FLEMMI: I’ll assert the Fifth on that.

WYSHAK: And that was really your goal throughout this entire period, was to gain control of criminal activities in Boston? Isn’t that true, Mr. Flemmi?

FLEMMI: We had formed a partnership, the FBI and I. How we benefited from it with their assistance or with their okay—yes, we did all right.

There were even times when Flemmi got mixed up—especially about whether he was supposed to view the leaks he’d gotten from FBI agents as either legal or illegal acts. The leaks, he argued, were proof of his claim of FBI protection. But would it matter to Judge Wolf if the leaking were illegal? Flemmi more than once wasn’t sure what position to stake out. At one point Wyshak was pushing Flemmi on the range of services Connolly provided Bulger and Flemmi—from warning the crime bosses about wiretaps to burying complaints against them, such as the extortion of Stephen and Julie Rakes—when the prosecutor suddenly asked, “You knew Mr. Connolly was breaking the law in his relationship with you, didn’t you?”

FLEMMI: Yes.

WYSHAK: In fact, do you know Stephen Rakes—Stippo?

FLEMMI: I’ll assert the Fifth on that.

WYSHAK: Well, you told us that—

FLEMMI: Excuse me, Mr. Wyshak. I just wanted to clarify one thing, when you asked me a question about did I know he was breaking the law. As far as I’m concerned, everything he was doing was legal—illegal—excuse me, legal.

WYSHAK: Now you’re saying you didn’t know he was breaking the law?

FLEMMI: No. I’m saying that everything that I believe he did, he as far as—it was consistent with his job. He was protecting us.

WYSHAK: Did you think it was consistent with his job to violate the law, yes or no?

FLEMMI: Whatever he was doing was legal.

WYSHAK: It was legal to tip you off on investigations?

FLEMMI: That’s correct.

Most of the time Flemmi had kind words for John Connolly, but he did express disappointment that Connolly had neither gotten him out of the current fix immediately following his arrest nor taken the witness stand during the hearings to defend their deal.

FLEMMI: He should be up here testifying on our behalf.

WYSHAK: So . . . he’s committed the cowardly act?

FLEMMI: Obviously—that he’s not here. I feel he should be here.

WYSHAK: So you feel he’s betrayed you also?

FLEMMI: I feel that we’ve been abandoned.

WYSHAK: Because if what you’re saying is true, he would have been knocking on the U.S. attorney’s door on day one, isn’t that true, Mr. Flemmi?

FLEMMI: He should be.

WYSHAK: Should have been knocking on my door and saying: “Hey, Fred, you made a mistake; this guy has immunity?”

The prosecutor’s near-constant mockery notwithstanding, the bottom line of Flemmi’s ten days of testimony, covering the career criminal’s murky collusion with the FBI, was that an FBI promise to protect was a covenant in perpetuity. Flemmi felt that he “would be protected for crimes past, present, and future.” If nothing on FBI paper existed to codify the deal, no matter. “We had a gentleman’s agreement,” he said about the arrangement he and Bulger had with Connolly, Morris, and the other agents.

“We shook hands. To me, that was an agreement.”

Perhaps the most dramatic moment came when Flemmi was asked if he’d been tipped to flee just before his indictment in 1995. With a sly smile, Flemmi replied, “That’s the big question, I guess.” Despite the torrent of evidence that pointed to John Connolly, Flemmi tried to convince the judge that John Morris was the one who obstructed justice by leaking a grand jury indictment. Flemmi apparently hoped this feeble scenario might lure Connolly to the witness stand to back his claim to an immunity defense. But many in the courtroom rolled their eyes. The most visible disbelief came from codefendant Frank Salemme. Until then, despite the close quarters in court and in prison, Salemme had managed to keep his deepening disdain for Flemmi in check during his week on the stand. Salemme had even weathered Flemmi’s denial that he was the one who ratted to the FBI Salemme’s New York location when he was arrested back in 1972.

But the Morris story was too much to bear. Salemme viewed it not only as a farce but as a threat to the immunity defense that could benefit all the defendants, not just Flemmi. In a game within a game, Flemmi looked to be currying favor with Connolly by protecting him. It put Salemme over the edge. During a break Salemme’s suppressed ire flared in the court’s holding cell. He went after the smaller Flemmi, lifting him up and screaming in his face. “You piece of shit,” he shouted. “You’ve fucked me all my life, and now you’re screwing everyone around you. You’re scum, and you’re gonna die.” Bobby DeLuca jumped in between the former partners in crime and broke it up. Salemme abruptly walked away from Flemmi and never spoke to him again.

▪   ▪   ▪

The hearings seemed to lose steam once the drama of Flemmi’s testimony ended. More FBI agents were among the remaining witnesses, including experts testifying about the FBI’s guidelines for handling informants. Debbie Noseworthy—who was now Debbie Morris—appeared briefly to corroborate John Morris’s account of the day John Connolly gave her $1,000 of Bulger’s money for plane fare. But the remaining witnesses were anti-climactic compared to the sight of a mob boss of Flemmi’s stature testifying in federal court. By October the months of testimony were winding down, and everyone had pretty much had their say.

Except John Connolly.

Thinking Judge Wolf was done, he launched a media blitz to rehabilitate a reputation that for months had taken a beating. Though he had been talking sporadically to reporters during the hearings, Connolly wanted the last word. He appeared on talk radio, on television, and as a centerpiece in magazines he’d selected to grant interviews. Each interview and article was friendly and supportive, a chance for Connolly to sound off virtually unchallenged. The headline on the cover story of the October 27 issue of the Boston Tab boldly announced, “Connolly Speaks Out,” and the cover featured a large photograph of John Connolly, dressed in his trademark tailored suit and wearing sunglasses, standing outside 98 Prince Street, the former Mafia headquarters. The meaning of the photo was clear: here was the G-man who took out the Mafia. “I’m Proud of What I Did,” screamed another headline, in bold print. But no interview was more fawning than the one Connolly had on WRKO-AM during the afternoon of Saturday, October 24, 1998. The host, Andy Moes, announced at the start that Connolly was an old friend, “a fine son of South Boston” and “a man I know to be an honorable and decent man.” Then came Moes’s breathless ode to Connolly.

MOES: Man, oh man. What has happened? Last time your name came up it was hero John Connolly. I’ve only heard your name referred to as, like, Prince of the City. Every supervisor, everybody I know who knows you in the FBI talks about what an incredibly smart, streetwise agent John Connolly was. John Connolly did the impossible. He was able to break through and literally bring down La Cosa Nostra to their knees in Boston, something the bureau was very proud of. And happy to take credit for. Those were the last stories I heard about John Connolly. All of a sudden, I’m hearing whispers, and they are whispers, that are done in back rooms, quietly: “He’s a rogue agent, you know. He was a rogue agent.” You a little tired of hearing that? You a little sick and tired of having people assassinate your character?

CONNOLLY: It’s wearing a little thin.

Like a politician, Connolly had certain “talking” points he seemed to want to get across each time he was interviewed: that he’d never done anything wrong in handling Bulger and Flemmi; that the crime bosses were merely a “gang of two” who helped the FBI take out the Boston branch of an international criminal organization; that Bulger and Flemmi did have permission from the FBI to commit certain crimes—gambling and loan sharking—while gathering intelligence; that John Morris was “an evil guy”; and that prosecutors Wyshak, Kelly, and Herbert had no business indicting the FBI’s informants back in 1995. Connolly called the prosecutors “cowards” who violated the FBI’s promise—and most important, Connolly’s promise—not to go after Bulger and Flemmi. “I never would have given my word to anyone had I ever thought there was a chance that the government would break it,” Connolly told Moes, his voice slowing to a crawl to put extra emphasis on his words. “They broke their word,” he growled. “Shame on them, the prosecutors here. But they had no right to break my word.”

By this time John Connolly had emerged as the kind of quintessential public figure for the 1990s, a decade increasingly obsessed with style and celebrity. It was as if Connolly had decided that if he self-assuredly proclaimed himself the true hero in the story—and he made this swaggering claim unabashedly, even tenaciously—then it would be true. Forget about the mountain of evidence before Judge Wolf and the hours of incriminating testimony. And for the most part Connolly did have his way during his media blitz. Just about the only bump in the road he encountered—albeit briefly—was a question posed by Peter Meade of WBZAM, who stopped Connolly to ask about an FBI actually condoning violence.

MEADE: Isn’t violence an inherent part of loan-sharking?

CONNOLLY: Well, uh. Not really. I mean, loan-sharking? Yeah, I mean, you know, violence is an explicit part of loan-sharking. Uhh. If someone doesn’t pay you, people hurt them. But, um, they, the deal with these two individuals and anyone else was—no violence. No murders. No violence.

During the blizzard of interviews Connolly piled up public relations points. He even turned up his rhetoric about the ongoing hearings before Judge Wolf. During most of the year he’d taken the position that, as much as he wanted to tell his side, he couldn’t testify without immunity, not when the prosecutors had him under investigation. But now that the hearings seemed to be over, Connolly was saying, immunity be damned—he didn’t want it, he didn’t need it. “I do not need immunity for corrupt acts,” he told the Boston Tab. “I did not commit corrupt acts. I would refuse immunity for those reasons. I don’t need it.

“They can stick it,” he added.

The overheated talk proved to be a misstep.

Both the defense attorneys and the prosecutors suddenly asked Judge Wolf to summon Connolly back to court, now that he was repeatedly saying that he no longer wanted immunity. It was one of those rare instances when Cardinale and Wyshak agreed. “It’s time to put Mr. Connolly’s feet to the fire on this issue,” Cardinale told the judge. Wyshak’s colleague Jamie Herbert noted that during the media interviews Connolly “has lied about what takes place in this courtroom and outside this courtroom.”

The lawyers had called Connolly’s bluff, and on the morning before Halloween, October 30, John Connolly returned to federal court, his lawyer Robert Popeo at his side. The broad-shouldered Connolly cut a striking pose on the witness stand. He wore a dark, fitted suit, a smart-looking yellow silk tie, and a white handkerchief was neatly arranged in his breast pocket. His hair appeared recently cut and styled.

Tony Cardinale cut right to the chase.

“Mr. Connolly, in 1982, did you give any cash to an FBI secretary named Debbie Noseworthy, now Debbie Morris?”

Cardinale was looking to provoke Connolly. “I was hoping his arrogance would get the better of him,” he said later. He wanted an angered Connolly to blurt out a denial—no, he had not delivered Bulger’s money to Morris! “Then boom—there would have been an instant indictment for perjury,” said Cardinale. “It would have made my day, after what he’s done to my client and to so many other people in his so-called role as a defender of the law.”

The two men locked eyes, and the question that Cardinale had asked in his baritone voice echoed in the courtroom. Then Connolly shifted in his seat and removed a card from the pocket of his suit. He held the card in his right hand, delicately between the tips of his index and middle fingers.

“Upon advice of counsel, I respectfully decline to answer at this time and rely upon my rights under the United States Constitution not to give testimony against myself.”

CARDINALE: On April 30 of 1998, as the Court has pointed out, Mr. Connolly, you appeared before the Court and refused to answer questions, asserting your Fifth Amendment privilege, is that correct?

CONNOLLY: That’s correct.

CARDINALE: Since that time, you’ve been interviewed by a number of media representatives . . . have you not?

CONNOLLY: Upon advice of counsel, I repeat . . .

Cardinale did not let up, firing off a string of questions: have you personally committed any criminal offenses with regard to any promise made to Mr. Bulger and Mr. Flemmi? Did you at any time give Mr. Morris around Christmas a box of wine containing $1,000? Did you warn Mr. Bulger and Mr. Flemmi of any existing investigative efforts that were targeting them? Did you know an individual by the name of Brian Halloran?

Each time, Connolly took the Fifth.

Then prosecutor Jamie Herbert had a turn.

HERBERT: Good morning, Mr. Connolly.

CONNOLLY: Good morning.

HERBERT: Mr. Connolly, you know what the term “bribery” means?

CONNOLLY: I assert my Fifth Amendment rights.

HERBERT: Mr. Connolly, you have told at least three different versions of this supposed deal that you had with Mr. Bulger and Mr. Flemmi, isn’t that correct?

CONNOLLY: I assert my Fifth Amendment rights.

HERBERT: Mr. Connolly, in all your years with the FBI working with Mr. Bulger and Mr. Flemmi, did you ever once document this supposed deal anywhere in the FBI files?

CONNOLLY: I assert my Fifth Amendment rights.

Inside of twenty minutes Connolly took the Fifth nearly thirty times to the questions Cardinale and Herbert posed. The judge broke off the give and take, ruling that the exercise was fruitless, that Connolly had not changed his mind and decided to testify without immunity. Robert Popeo told the judge that his client was asserting the Fifth at his insistence, particularly “in light of the fact that there are two separate grand juries sitting in which we have been advised by prosecutors that Mr. Connolly is a target.” Even if Connolly was speaking boldly outside of court and proclaiming his innocence—a right of free speech under the First Amendment—he was not waiving his rights under the Fifth Amendment against self-incrimination.

“To each and every substantive question put to the witness,” said Popeo, “he has been advised to invoke his privilege under the United States Constitution.”

The judge excused Connolly. “Mr. Connolly, you may go.”

Minutes later Connolly could be found outside the new courthouse on Fan Pier, holding forth to a circle of television cameras and reporters, resuming his bellicose stance toward prosecutors Wyshak, Herbert, and Kelly. He called them “character assassins” hell-bent on singling him out as their scapegoat. But even a renewed attack could not remove the lasting impression of a lackluster John Connolly reading from the Fifth Amendment card he’d just spent weeks telling the world he no longer needed.

▪   ▪   ▪

Then came the waiting game. In chambers, with the aid of his clerks, Wolf began the task of preparing a ruling, studying the testimony, the exhibits, and the applicable case law. Months passed, and by early 1999 the case had mostly fallen from public view. Occasionally, in other contexts, it popped up. The former US attorney and ex-governor Bill Weld appeared on a radio show in 1998 to promote his first novel and ran into a host who wanted to ask about the Bulger affair with the FBI. Christopher Lydon of WBUR’s The Connection was incredulous that Weld hadn’t done more to dig out the Bulger mess. “Why aren’t you more outraged?” challenged Lydon. “Did your friend William Bulger know about it? Did you ever ask him about it?”

The usually garrulous Weld went mum. He replied no, a trace of annoyance in his voice. Lydon kept going, but mostly in monologue. Rather than join in, Weld allowed seconds of silence to fill the radio space. Of particular concern to Lydon was the recent suicide of Billy Johnson, the state trooper who had gotten tough with Whitey Bulger at Logan Airport over smuggled cash and later believed the encounter had cost him his career. “He killed himself!” said Lydon. “A miserable man at the end of a life that he thought had honorably been devoted to law enforcement.

“Where’s the outrage?” Lydon asked again.

The tense encounter ended finally, and the two got to talking about Weld’s novel. But Weld’s reluctance to get into it with Lydon seemed to capture symbolically the reluctance of Weld’s generation of Boston law enforcement leaders to ever seriously tackle the Bulger scandal.

By the end of the summer of 1999 word began spreading around town that Wolf, after ten months of rumination and writing, was applying the finishing touches to his ruling. In early August FBI director Louis Freeh arrived in Boston and, at a press conference, acknowledged publicly that the FBI “made significant mistakes” during the Boston FBI’s twenty-year run with Bulger and Flemmi. The admissions were seen as an effort by a publicity-obsessed FBI to take some of the sting out of the upcoming federal court ruling. “We have a lot of mistakes to account for,” said Freeh. He promised that corrupt FBI agents from Boston would be brought to justice.

Two weeks later the FBI announced that the fugitive Whitey Bulger was finally being added to its Ten Most Wanted List. The move—more than four years after Bulger fled his 1995 indictment—was seen as long overdue. In the public’s mind in Boston, the perception had taken root that the FBI was never really interested in tracking down its former informant. But now Bulger joined the likes of fugitives Eric Robert Rudolph, a suspect in abortion clinic bombings, and Osama bin Laden, the Saudi terrorism suspect. And he held a distinction all his own: he was believed to be the first FBI informant to ever make the famous top ten list, which had posted 458 fugitives since its inception in 1950. His face would now appear across the country in post offices and federal buildings, on the FBI’s website, and even in a Dick Tracy cartoon as part of an FBI Most Wanted promotion.

In cellblock H-3 three celebrated inmates were also eagerly awaiting the ruling—Frank Salemme, Bobby DeLuca, and Stevie Flemmi. Their high hopes were that the judge would find the evidence so compromised that he would throw out the racketeering charges against the group—that Wolf would rule that the FBI had indeed promised blanket immunity for Flemmi and Bulger and therefore the government could not now violate that immunity and prosecute them.

Ever since their arrest in 1995 the three mobsters had been kept at the Plymouth prison, a modern facility that opened in 1994 and was located forty-eight miles south of Boston. The new facility had been built atop an old landfill in an isolated, unwanted area of the historic community. It was also right off of Route 3, a highway connecting Boston to Cape Cod, and Flemmi, from his cell, could hear the hum of freedom in the distance, the cars carrying commuters and vacationers along a route he and Bulger and John Connolly all used to take on their way to the Cape.

The cellblock could hold 140 inmates in seventy cells. It was a large rectangular space constructed as a self-contained “miniprison,” meaning that the inmates spent virtually all of their time on the block and did almost everything there. Meals arrived on wheels from a central prison kitchen, and inmates ate at the tables in the unit’s common area. The cell-block had its own showers along one end, its own televisions, and its own pay phones. It was smoke-free. The unit had a “rec deck,” a small, outdoor recreation area that opened up off the far end of the unit. The area was essentially a fenced-in cage, but inmates could escape the stale air of the cellblock and get some exercise by going out there. The chin-up bar attached underneath a set of stairs was jokingly called “the gym,” and the cart of books positioned against one wall was “the library.” Two decks of cells, on a ground floor and a mezzanine level, lined the long walls of the cellblock. Salemme and DeLuca lived side by side in cells at the far end of one mezzanine level, near the entrance to the rec deck. Flemmi was on his own.

Over time Salemme had emerged as a model inmate and cellblock leader. The guards relied on him. He was given the top cellblock job, a position previously occupied by, of all people, Howie Winter, until Winter was moved out of the unit. Frank was the “meal server”: three times a day, while all the other inmates were locked down, he set up the common area for meals. He put ice in the juice pitchers, wiped down the tables, arranged the chairs. No job on the unit carried more responsibility—not cleaning the rec deck, emptying the trash bins, cleaning the showers, or sweeping the tiled floors and the mezzanine walkway. The guards wanted the unit as shiny and clean as a hospital ward, and Frank was the key inmate making that happen. It was a far cry from his old life as a high-rolling gangster, but the job, a way to help pass the days, kept the mobster busy.

DeLuca was not as motivated a worker. His job was sweeping the mezzanine. But like Salemme, he worked out and wanted to stay in shape. He regularly performed chin-ups to keep his upper body hard and muscular. Both watched their diet, especially Salemme, who avoided the high-fat prison offerings and preferred salads and fruits. Salemme also read a lot—boating magazines, Tom Clancy, and Dean Koontz.

Flemmi was another story. During the course of the hearings in court, as the extent of his FBI deal was exposed, Flemmi was pushed further and further to the margins of cellblock life. Inmates did not want to have anything to do with him. He was ostracized—a rat, the lowest form of underworld life. Salemme would not talk to him, would not even look at him. Flemmi sometimes approached DeLuca, but the encounters were curt and brief.

The alienation that came with being a career informant was bad enough, but Flemmi withdrew further into himself the day Johnny Martorano was whisked away to commence cooperating with the prosecutors. The prison guards surely weren’t going to miss the hitman. Martorano gave them the creeps—a surly, cold-blooded troublemaker who strutted around the cell-block as if to say: Get out of my way, I’m John Martorano, and I kill people. But Martorano’s departure was devastating to Stevie Flemmi. It meant that Martorano was implicating Flemmi and Bulger in murder—particularly the 1981 assassination of Roger Wheeler. It meant that even if Flemmi’s lawyer Ken Fishman succeeded in persuading Judge Wolf to throw out pending racketeering charges, the prosecutors were preparing to come back with a new indictment for murder.

In early September, as everyone was waiting on Judge Wolf, the news broke that Martorano and the government had completed negotiating the terms of a plea bargain for Martorano’s testimony. In exchange for a sentence of twelve and a half to fifteen years, Martorano had agreed to plead guilty to twenty murders spanning three decades and three states, including the murder of Roger Wheeler, a killing he claimed was committed on orders from Bulger and Flemmi. “The people he’s giving up are people who have enjoyed the protection of the FBI for many years while committing heinous crimes,” said David Wheeler, son of the slain Jai Alai executive, voicing support for the hitman’s deal.

Flemmi retreated to his prison cell. In cellblock H-3 the former crime boss was shunned, and he spent most of his time alone, seated on his bunk. “Just there,” said one guard. “He’s like the bag of golf clubs sitting in my closet.” Flemmi didn’t have a cellblock job to keep him busy. He didn’t have anyone to talk to. “He’s about as despondent as you can get without going insane,” one officer noted. Flemmi rarely, if ever, went out on the rec deck for the fresh air or the sun. It was the eve of one of the most eagerly awaited court rulings in the biggest organized crime case in Boston’s history, and Flemmi’s face had turned pallid, almost translucent. His skin had turned the color of the prison walls, one guard observed—a ghostly “popcorn white.”

▪   ▪   ▪

Tony Cardinale, the lawyer who had kicked open the Pandora’s box hiding the FBI’s affair with Bulger and Flemmi, began the day the ruling finally came out with a workout at the Boston Athletic Club. Then he picked up his associate John Mitchell, who’d flown in from New York City, at his hotel. They swung by the courthouse, where a clerk handed the lawyers a box containing seven copies of the ruling. Immediately Cardinale dispatched a messenger to take a copy down to the Plymouth prison for Frank Salemme. Then, huddled in shirtsleeves in Cardinale’s office, the Dunkin Donuts coffee and donuts spread out on the desk, the two lawyers opened up the thick ruling and began reading.

Boston Herald columnist Howie Carr would later wisecrack that Mark Wolf must have fashioned himself the Edward Gibbon of New England organized crime, penning The Rise and Fall of the Bulger Empire: it ran 661 pages. Cardinale and Mitchell both enjoyed the way Wolf opened his treatise, quoting from Lord Acton. “In 1861,” the judge began, “Lord Acton wrote that ‘every thing secret degenerates, even the administration of justice.’” To that the judge added, “This case demonstrates that he was right.”

The donuts sat uneaten. The lawyers couldn’t put the ruling down. The legal part—the immediate impact on the status of the racketeering case—was inconclusive. For example, the judge refused to find that all of the protection the FBI had provided Bulger and Flemmi—much of it illegal—amounted to blanket immunity from prosecution. But he had decided that past FBI promises to Bulger and Flemmi tainted some of the wiretap evidence and that those tapes would never be used against them. The judge said he was going to suppress that evidence, and possibly more. With that, the racketeering case seemed to be hanging by a thread. But to reach a final decision on the disputed evidence the judge had decided he would need still more information, drawn from even more pretrial hearings. “In essence,” concluded Wolf, “the record for deciding Flemmi’s motions to dismiss and suppress is incomplete. Therefore, the court will hold the hearings necessary to determine whether this case must be dismissed and, if not, the scope of the evidence to be excluded at trial.” It meant that, for now, the case would go on.

But the legal part of the judge’s ruling was not the story of the day. The hard news was the judge’s “findings of facts” about the FBI and Bulger and Flemmi. More than half of the text—368 pages—was devoted to factual findings about all that had gone wrong in the FBI’s deal with Bulger, judicial findings resulting from sworn testimony and the mountains of FBI documents and files.

The judge acknowledged that Bulger and Flemmi were “very valuable and valued confidential informants” for the FBI, but then proceeded to describe in minute detail the corruption, rule breaking, and misconduct that defined the deal almost from its start three decades earlier. The leaks—from the Lancaster Street garage to the DEA’s car bug to the Baharoian wire—were all there, along with the long list of tips the crime bosses got about other wiseguys who posed a threat to them. “In an effort to protect Bulger and Flemmi, Morris and Connolly also identified for them at least a dozen other individuals who were either FBI informants or sources for other law enforcement agencies.” The judge cited the Brian Halloran leak and the fact that, a few weeks after he had talked to the FBI, “Halloran was killed.”

The judge concluded that, to protect Bulger and Flemmi, agents essentially fictionalized the FBI’s internal records on a regular basis, both to overstate their value and to minimize the extent of their criminal activities. The FBI’s files showed “recurring irregularities with regard to the preparation, maintenance, and production in this case of documents damaging to Bulger and Flemmi.” And despite Connolly’s claims to the contrary, Wolf ruled that the handler did indeed handle Morris’s bribe money. “Morris solicited and received through Connolly $1,000 from Bulger and Flemmi.”

The judge also cleared up some of the smaller details of the sordid saga. Despite Billy Bulger’s public comments to the contrary, the judge ruled that the powerful politician had in fact made a cameo appearance. “William, who was the President of the Massachusetts Senate and lived next door to the Flemmis, came to visit while Ring and Connolly were there.”

“Man-o-manischevitz!” Cardinale exclaimed. He and John Mitchell began a duel of sort, reading passages aloud, each one trying to top the other with a juicier factual finding.

In all, Wolf identified eighteen FBI supervisors and agents as having broken either the law or FBI regulations and Justice Department guidelines. Paul Rico, John Connolly, and John Morris were at the hub of the wrongdoing, and the list included supervisors Jim Greenleaf, Jim Ring, Ed Quinn, Bob Fitzpatrick, Larry Potts, Jim Ahearn, Ed Clark, and Bruce Ellavsky, and agents Nick Gianturco, Tom Daly, Mike Buckley, John Newton, Rod Kennedy, James Blackburn, and James Lavin.

“John Connolly is fucked,” said Cardinale, shaking his head, pausing at the section in Wolf’s ruling where he addressed a central question: how Whitey got away in early 1995. Even though Flemmi had testified that the leak came from Morris, the judge found that Flemmi, while generally truthful in his testimony, was not always “candid” and “at times attributed information received from John Connolly to other agents of the FBI in an evident effort to protect Connolly.” Despite Connolly’s strident public statements, Wolf had ruled that Connolly was the culprit.

“The court concludes that in early January 1995, Connolly, who remained close to Flemmi and, particularly, Bulger, had been monitoring the grand jury investigation in part through his contacts in the FBI, and was in constant communication with Bulger and Flemmi about the investigation, was the source of the tip to Bulger.”

Finally, despite Jeremiah T. O’Sullivan’s public comments to the contrary as well his statement to federal investigators in 1997, the judge ruled that O’Sullivan had known Bulger and Flemmi were informants since 1979.

The ruling exposed the ugly addiction the Boston FBI had to Bulger, and it was not a pretty picture. By sheer coincidence the ruling came out just twelve days after a personal milestone for Whitey Bulger: he turned seventy years old on September 3, 1999. But the 661-page treatise was hardly the sort of birthday greeting he would have wished for. James J. “Whitey” Bulger may still have had his freedom, but there was little else to celebrate.

“Judge Blasts FBI for Deal with Bulger and Flemmi” was the front-page headline in the next day’s tabloid Boston Herald. “Judge Says Hub FBI Broke All the Rules.”

The headlines had captured the moment, and they were headlines that no doubt reached Whitey Bulger himself—out there, somewhere, still on the run, riding the back roads of rural America with a bleached blonde by his side, false papers in his wallet, and packets of $100 bills stashed in safety deposit boxes around the country.