In for a Penny, in for a Pound - THE RUSSIA HOUSE - Black Mass: Whitey Bulger, the FBI, and a Devil's Deal by Lehr, Dick, O'Neill, Gerard (2012)

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


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



In for a Penny, in for a Pound

Their cells were side by side on the mezzanine level of cellblock H-3 at the Plymouth County Correctional Facility, number 419 belonging to Cadillac Frank Salemme and number 420 to Mafia soldier Bobby DeLuca. The seven-by-nine-foot cells had gray cement floors and walls painted a dull white. It was late summer 1996, and the racketeering case against the Mafia and Bulger and Flemmi, albeit with Bulger in absentia, was chugging along in low gear. The federal case was in discovery, a pretrial stage in every criminal case when the government discloses to the defense relevant evidence and potentially exculpatory material about the accused. The defense then studies the material, primarily to prepare for trial but, even before that, to see if it can gut the government’s case by finding legal fault with the way the evidence was developed. If defense lawyers can persuade the judge that all or part of the evidence was somehow obtained wrongly, the judge might throw it out. Depending on how much evidence goes, the case against the accused either shrinks or, better, evaporates.

Salemme and DeLuca huddled over a Sony tape recorder. Their Boston attorney, Anthony M. Cardinale, had given them a homework assignment. Listen to the tapes, the lawyer had instructed—listen carefully. The lawyer had brought to the prison handfuls of tiny cassette tapes that were copies of recordings the FBI had made during covert electronic surveillances—from 98 Prince Street, Vanessa’s, Heller’s Café, a meeting of two mafiosi at a Hilton Hotel at Logan International Airport, the Mafia induction ceremony in 1989, and others.

Tony Cardinale was listening to the tapes himself, but he wanted Salemme and DeLuca listening too. Their ears were better trained for the Mafia talk. The voices belonged to their guys. All three were looking for a way to challenge the tapes’ admissibility, a way to knock them out of the ring so they could not be used in court. Listen, Cardinale instructed, for anything irregular.

Of particular interest to the lawyer were the tapes the FBI had made by using a “roving bug.” Unlike any other bug, this bug was not fixed in a ceiling or wall or beneath a lamp. Instead, this powerful and portable hand-held microphone could move, inside a dish that FBI agents aimed at people to pick up their conversation, even if they were inside a car or house. The FBI turned to a roving bug when it did not know in advance the location of a meeting or when it otherwise lacked the time necessary to install a fixed bug or a telephone wiretap. By its mobility, the roving bug was a highly effective brand of electronic surveillance that sent chills down the spines of both guardians of privacy rights and criminal defense attorneys. Cardinale, for one, was no fan. “The roving bug is probably the most dangerous government intrusion,” he said. “In a sense, they’ve thrown out the Fourth Amendment protections. Because if you’re the target, then the government can go anywhere you go. To your house. To your mother’s house. To a church. Anywhere you are, the government has probable cause, a walking search warrant. It’s a vast expansion of electronic surveillance, and it’s a nasty little tool that should not be misused.”

Cardinale had a hunch about the Boston FBI’s use of roving bugs—namely, that the FBI was misusing them. He was convinced that the FBI, contrary to what agents swore under oath to judges, did know far enough in advance where certain meetings were going to take place. The agents knew this, he believed, because they had one or more of their confidential informants attending the meetings. If this were true—if federal judges had been misled—the defense might be able to get all or some of the tapes suppressed.

Salemme and DeLuca took their assignment seriously. Behind the hard green steel doors of their cells, seated on the thin mattresses of their metal bunk beds or at the tiny metal desks attached to their walls, the men played the tapes. There were hundreds of tapes, and the work was mind-numbing, as they played and replayed the conversations, straining to hear the dialogue.

Bobby DeLuca especially took to the task at hand, and one day, while concentrating on the Hilton-Logan tape, he detected something in the background. He stopped, replayed the passage, and the more he listened the more he became convinced he could hear other voices besides the two targeted wiseguys. DeLuca summoned Salemme, who listened to the tape. Salemme heard the extra voices too. DeLuca wasn’t crazy. Two voices in the background were whispering. It had to be the FBI agents overseeing the taping. Somehow the roving bug they were using from the next hotel room had also captured their voices, and one agent was whispering to the other agent that they should have gotten “the Saint” to give one of the wiseguys “a list of questions.”


DeLuca and Salemme stopped the tape and eagerly placed a telephone call to Cardinale in Boston.

▪ ▪ ▪

The mafia had been calling on Tony Cardinale for years, and at forty-five, he possessed the seasoning, ego, and stamina to go deep into any contest with the government. By the time of the 1995 indictment of Salemme, Bulger, Flemmi, and the others, he was Boston’s leading mob lawyer. Fond of Hermes silk ties, fine cigars, and scotch, Cardinale relished the combat of the courtroom. He was a lawyer who was best on his feet, seemingly restless behind a desk. It had always been this way for the litigator who’d grown up in Hell’s Kitchen in New York City, the son of a boxer and restaurateur. Cardinale’s father and four uncles ran Delsomma’s Restaurant on Forty-seventh Street between Eighth Avenue and Broadway, popular with the theater crowd, the old Madison Square Garden folks, and the wiseguys from the West Side. His father also trained boxers, and Tony Cardinale grew up under his father’s careful eye, taught to bob and weave, jab-jab, a right, bam! a left hook, bam! Boxing dominated the talk at the restaurant and at home, a railroad-style flat on the third floor of a tenement on Forty-sixth Street, right next to a fish market. Two uncles and their families lived across the street; his grandmother and another uncle lived around the corner. Tony Cardinale ran with the Forty-sixth Street Guys, a gritty, true-life version of the street gangs glamorized in the musical West Side Story. The teen Cardinale wore the late 1950s getup of blue jeans, white T-shirt, sneakers, and garrison belt, a thick, big-buckled belt that could double as a weapon.

Young Tony Cardinale grew up watching the city pass through the doors of his family’s restaurant—fighters, gangsters, high rollers, businessmen—and this was the spot where he first picked up the notion of someday becoming a lawyer. “If my dad met a guy at the door who was a lawyer or a doctor, he would be really impressed,” said Cardinale. “He would be very solicitous, very respectful.

“Something happened, something special about seeing that, because I’d think, as I saw how my father treated people who were lawyers, I’d say, ‘You know, that’s what I want to be, Dad,’ and he’d say, ‘God, if you ever do that, that would be great, that would be wonderful.’”

On a football scholarship Cardinale attended Wilkes College in Pennsylvania. He wanted to go to law school in New York City, but NYU, Columbia, and Fordham all rejected him, so Cardinale traveled to Boston, newly married, to attend the only school that would take him, Suffolk Law School. He never left the city. Indefatigable, he made law review. In his second year he and classmate Kenneth J. Fishman began working for famed defense lawyer F. Lee Bailey. Cardinale and Fishman became lifelong friends. Bailey called the two “the Gold Dust twins” because they came into the office at the same time and were attending law school together. The mentor thought of Fishman as “the law guy” for his acumen in legal analysis and Cardinale as “the fact guy” for his ability to investigate a case and track down flaws in the opponent’s reasoning. “He had a good measure of self-confidence,” Bailey said later, remembering a young Cardinale. “He’s got good-sized balls.”

Cardinale stayed with Bailey for five years, then struck out on his own in the early 1980s, working the trenches, building on the fast start he’d gotten with Bailey by piling up courtroom experience. Then in late 1983 he took on his first Mafia client—Gennaro Angiulo, of all people. The underboss’s original attorney, in line for a judgeship, had dropped out of the case, and Cardinale got the call one night after Christmas: “How would you like to represent Jerry Angiulo?” It was the big break, and Cardinale was eager. “This was a major league, major league case,” he said. “I want to get in the game, you know. That’s the athlete part of me coming out—if this is the biggest game in town, then I want to be in it.” Just thirty-three years old, Cardinale was the lead attorney in the biggest organized crime case in Boston’s history.

Cardinale went to war. He relentlessly attacked the devastating 98 Prince Street tapes, their quality, their accuracy, all in an attempt to knock them out of court. The trial lasted nine grueling months, and each day Cardinale was on his feet trading blows with the government team led by Jeremiah T. O’Sullivan.

In the end the House of Angiulo had fallen, but Cardinale had made it, even if his hair turned gray during the trial. Just like that, he had become the up-and-coming practitioner for the mob. During the 1980s he represented other Angiulos and Vinnie Ferrara, and he commuted to New York to represent “Fat Tony” Salerno. In the early 1990s he joined the defense team of John Gotti, representing Gotti sidekick Frank “Frankie Locs” Locascio. In the 1995 indictment of Cadillac Frank Salemme, Tony Cardinale was again the Mafia’s go-to guy. Flemmi, meanwhile, tapped another leading defense attorney, Cardinale’s law school friend Ken Fishman.

Cardinale was ecstatic to hear from Salemme about their cellblock discovery. He had turned his own office into a quasi-electronics center, with high-quality tape recorders and enhancers, and when he listened to the tape himself, he too heard the whispering that Salemme and DeLuca had detected. Each time he replayed the passage, he felt more certain that he now had a legal smoking gun, something he could use to land a counter-punch against the government. He had technicians enhance the tape, and the background FBI voices were less faint. The two agents operating the roving bug were complaining about the rambling, unfocused conversation under way in the next room between a local wiseguy named Kenny Guarino and a visiting mobster from Las Vegas named Natale Richichi. One agent seemed to tell the other that beforehand they should have had “the Saint” make up “a list of questions of shit … for Kenny to ask him … we could, you know, narrow the different categories.”

To Cardinale this was proof that the FBI had at least one—and maybe two—informants participating in the meeting with the visiting Mafia figure from Las Vegas. Cardinale figured that either Kenny Guarino or “the Saint”—a nickname for Anthony St. Laurent—or both, were working as FBI informants. If either wiseguy was an informant, then the FBI had probably known beforehand the location of the meeting at the Hilton. And if that were true, the FBI had not had a valid basis for using a roving bug and had lied to a federal judge to win his permission for one.

Cardinale prepared new court papers and, tape in hand, argued to the judge sitting in the racketeering case, Mark L. Wolf, that a special hearing was warranted to look into possible FBI subterfuge. The documents related to the case were sealed, and the court sessions held to discuss Cardinale’s findings were closed to the public. Cardinale argued that to get another judge’s okay to use a roving bug FBI agents in 1991 had filed sworn affidavits saying they had no idea where Richichi was going to be when he came to Boston on Mafia business. Cardinale, urging the judge to listen to the tape himself to hear the background FBI voices, said, “The FBI knew a great deal more about the events of December 11, 1991, but wanted to protect their source.” The Boston FBI, suggested Cardinale, was possibly “involved in illegal conduct in an effort to conceal the activities of their high-level informants.”

Throughout the fall of 1996 the matter was pursued during court sessions that remained closed to the press and public. Cardinale and a team of prosecutors led by Fred Wyshak engaged in a legal shoving match, with Cardinale seeking to push the envelope while the government pushed back.

During this time Cardinale began to develop an even more ambitious game plan. He believed the subterfuge behind the FBI roving bug at the Hilton was not an isolated event. He felt that for years the FBI had bent and broken all kinds of rules to protect a coterie of informants. In particular he believed that the FBI was especially protective of Whitey Bulger. Cardinale had read the stories in the Boston Globe, and he’d heard all the talk on the street about Bulger and the FBI. He also believed that Bulger had escaped arrest because the FBI let him get away.

All the Bulger talk had gone on outside of court, but Bulger was a co-defendant now, and to defend his client, Salemme, Cardinale was deciding to go after Whitey. He would employ the Hilton tape as a battering ram to knock down the wall of secrecy. Cardinale was going after the FBI.

▪ ▪ ▪

Defense counsel seeks the disclosure of the identity of various individuals who may have served as government informants/operatives in connection with the investigation and/or prosecution of this case,” the lawyer began a motion filed on March 27, 1997. The papers were submitted under seal, and the discussions before Judge Wolf regarding the FBI and Bulger continued to unfold in secret. Cardinale claimed that FBI misconduct might have tainted all or part of the government’s evidence, and to get to the heart of the matter the world needed to know about Bulger and the others.

In his motion Cardinale named Bulger and several other suspected informants, such as Guarino and St. Laurent—but not Stevie Flemmi. “I was just a little uncomfortable,” said Cardinale later. “Keep in mind, one of the last things you want to do in a situation like this—I mean this guy is a defendant in the case, and if you believe he’s been a rat essentially his whole life, one of the last things you want to do is to pull the trigger on the guy when you’re not ready, and the guy gets scared and rolls, and he hurts your client. I thought if the finger was pointed at Flemmi too early and he rolled, he could not only try to hurt Salemme but any number of people. It could have been a disaster.”

So for the time being Cardinale held back, partly out of caution and partly out of courtesy to his colleague, Ken Fishman, who was representing Flemmi. Besides, at the time the conventional wisdom still held that Flemmi was a stand-up guy. “The word on the street was about Bulger,” noted Cardinale. The Globe stories a decade before had been about Bulger and the FBI, not Flemmi. Bulger was the one who had evaded arrest in 1995, not Stevie. “You know, nobody had ever really said anything about Flemmi. Even among the Italians, I mean they always said, ‘Listen, Bulger is capable of anything,’ but Flemmi, they considered him almost one of them.”

Every step of the way Fred Wyshak and his fellow prosecutors fought Cardinale. They didn’t know exactly what horrors were hidden inside the FBI’s files, and they wanted Judge Wolf to keep his eye solely on the prosecution at hand. Wyshak had gone so far as to share with the judge—but not with the defense—an “extremely confidential” affidavit by Paul Coffey, the chief of the Organized Crime and Racketeering Section of the Justice Department. In it Coffey reported that as informants Bulger and Flemmi were never given specific authorization to commit crimes and that both were given periodic warnings that they were “not authorized to commit any criminal act absent specific authorization.” Ironically, Wyshak was forced to defend the FBI deal with Bulger for the sake of stopping Cardinale. The government, Wyshak insisted, did not have any formal but undisclosed deals with Bulger or Flemmi that would bar the present prosecution. The judge, argued Wyshak, should therefore ignore Cardinale’s “sweeping and nonspecific allegations.” Bulger and his relationship with the FBI was irrelevant, a distraction. Just as important, the court should not put the FBI in the harmful position of having to confirm or deny in public the names of the confidential informants so crucial to the bureau’s work.

But Wolf did not agree.

To the government’s dismay, on April 14, 1997, the judge decided that he wanted to learn more about Cardinale’s claims, at another closed hearing to start in two days. “The court has reviewed the defendant’s Motion to Disclose Confidential Informants and Suppress Electronic Surveillance conducted in this case,” wrote Wolf in a quick three-page ruling. “In this case, in which the defendants are charged, among other things with … conducting a racketeering enterprise, the fact that a codefendant was during the relevant period a confidential informant for the FBI would, if true, constitute exculpatory information to which his codefendants are entitled.” Wolf even ordered the government to bring along Paul Coffey and said that Coffey should be ready to talk about informants.

Between the lines in the ruling, Cardinale thought he detected a hint that his aggressive inquiry should not stop at Bulger but embrace Flemmi as well. “He says he wants the government to be prepared to answer questions as to whether ‘a’ defendant in the case—what impact that has if ‘a’ defendant is an informant. Now what happens is, I read from that that the judge, he was indicating that it is a defendant who is actually presently in the courtroom, not one who is on the lam, as Bulger was.”

The night before the hearing the lawyer shared this latest theory with his colleagues in a meeting at Ken Fishman’s office. There was John Mitchell, a New York City attorney who had joined Cardinale in representing Salemme and DeLuca, along with attorneys representing John and James Martorano. The half-dozen men and women were gathered around a conference table in the office on Long Wharf in a building that was rustic waterfront—restored red brick and exposed wood beams—next door to the New England Aquarium. Cardinale couldn’t even get through explaining his hunch when the other attorneys nearly hooted him out of the room. Mitchell looked at his pal and told him, quit being an asshole. Ken Fishman rolled a piece of paper up into a ball and tossed it at his former partner. No one had ever really talked about Flemmi as being part of the rat pack.

“Everybody had this sense that this guy was different than Bulger. He had been caught, and he was sitting in jail, and he was part of this ‘all for one and one for all’ defense effort,” said Cardinale. “I was convinced otherwise.”

During the meeting Cardinale did not even know if Fishman and his client had ever discussed Flemmi’s secret double life with the FBI. In fact Fishman was flummoxed hearing Cardinale say he was planning to go after Flemmi. “I don’t know that I have reacted so dramatically to anything Tony has ever said in the last twenty years,” Fishman said. The other lawyers insisted that Cardinale was misreading the judge and was way out of line.

But Cardinale wanted to prepare them for the possibility he was correct. He told the lawyers he’d already explained his plan to his clients, going over the underlying risk to this roll of the dice: if true, Flemmi might flip and turn against the other defendants in the case. For his own client, Frank Salemme, the potential exposure was limited. “Frank had been in jail for most of the Bulger-Flemmi reign, so Flemmi couldn’t give up much as far as Frank was concerned.” For the others, however, the risk was real.

The next morning the defense lawyers, their clients, and the prosecuting team led by Wyshak and Paul Coffey of the Justice Department all assembled behind the closed doors of Judge Wolf’s courtroom number 5 in the federal courthouse in Post Office Square. “We’re here pursuant to my April 14 order, which is under seal,” said Wolf from the bench, getting right into it. “I will say that I’ve closed the courtroom to the public because the matters that we will be discussing will relate to the disclosure to defendants and possible public disclosure of confidential informants.”

The judge reviewed Cardinale’s motion, mentioning the names Cardinale had included—Bulger, Kenny Guarino, Anthony St. Laurent, and two other underworld figures. The judge paused and looked up from the paperwork.

Then came the question Cardinale had been waiting for.

“Are the defendants interested in knowing about other individuals who might be similarly situated, if those people are indeed confidential informants? Or is it just those five?”

There was silence; all the dark matter that defined the world of Bulger and Flemmi as FBI informants was about to begin to ooze out, like toxic waste that had finally eaten its way through containers meant to seal the poison forever.

“It was a weird moment,” recalled Cardinale. The judge, he said, had “a kind of smile on his face. I knew then that my hunch was not just a hunch.” Cardinale walked over to his clients, Salemme and DeLuca. The lawyer knew there was no turning back. “I said, ‘Listen, we’re taking this step now. It could have some very negative impact. This guy could roll.’ But their position was, ‘Hey, Flemmi can’t say anything about me. He’d have to lie, so go on. Do it.’”

Cardinale turned and faced the front of the courtroom. The judge’s question was pending: is it just those five?

“As the old saying goes,” Cardinale said, “in for a penny, in for a pound, Judge. If there’s more, so be it.”

“That means you want it?” the judge asked.


▪ ▪ ▪

Minutes after Cardinale’s reply Wolf retired to his chambers. He ordered Paul Coffey of the Justice Department to come along with him. During the brief recess the judge and the Justice Department official discussed the crossroads the case had reached. Coffey told the judge that “our relationship,” meaning the FBI’s, was not just with Bulger but included Flemmi too. That was the point, the judge replied. If the judge was going to allow the defense to explore whether the FBI’s ties to Bulger poisoned any of the evidence, then Flemmi had to be part of that. It made no sense otherwise. (Wolf would later write that the two were “virtual Siamese twins.”) Both acknowledged that Flemmi, seated in court, did not seem to realize what was about to occur.

The judge left his chambers and returned to the courtroom, where the lawyers and the defendants had simply sat, waiting. Wyshak and his team tried again to stop Wolf from going any further, insisting that the informant angle Cardinale was pushing was no more than a red herring. Cardinale protested. Wolf called a halt to the debate. “Unless the government objects, I’d like to see Mr. Fishman and Mr. Flemmi in the lobby,” the judge decided.

“There’s something that’s come to my attention that’s negative about you,” Wolf said to Flemmi as soon as he, Flemmi, and Fishman had sat down in the private chambers. “I’m going to encourage you to think about it.”

“That’s fine,” said the ever-casual Flemmi. No sweat.

Judge Wolf asked Fishman to leave the room. Then he told Flemmi he would have preferred to have Fishman present for their chat, but he didn’t know how much information Flemmi had shared with his attorney about his past. Out of caution, the judge said, it was better to talk alone first.

“I just want you to listen to this,” Wolf said.

The judge reviewed Cardinale’s motion to Flemmi—how Cardinale wanted certain FBI informants identified as part of an effort to challenge the admissibility of the prosecution’s case against Frank Salemme and the others. Wolf told Flemmi that, as part of that process, he’d received documents informing him that Bulger—and Flemmi—were indeed informants. Wolf said he was inclined to rule in Cardinale’s favor and permit discovery of FBI informant names. In short, the judge was going to require that the FBI disclose publicly its work with Bulger and Flemmi.

“Do you feel comfortable about what we’re going to do with this?” Wolf asked after he’d finished his lecture. “Do you feel fear or anything?”

“No. I’m comfortable about my safety,” said Flemmi. “I’m not concerned about it at all.” But inside Flemmi had to be churning, bewildered by this turn of events. Ever since his arrest in early 1995 he’d kept quiet about his secret life with the FBI. He’d viewed his arrest as a mistake, or maybe somehow necessary as a cover to conceal his ties to the FBI, but a charade that Bulger and their friends at the FBI would eventually resolve quickly. “I believed that James Bulger would contact the people that would be able to help us because we were involved with the FBI for so many years,” Flemmi said later. He was quietly biding his time, remembering that years before, in the 1960s, it had taken Paul Rico and the FBI nearly four years to clean up the murder and bombing charges against him and pave the way for his return from Canada.

Flemmi also realized that the real reason Wyshak was fighting Cardinale about the disclosure of informant identities was not out of any love for him. Wyshak was trying to keep the case clean and straightforward and prevent Cardinale from knocking out any evidence. But now the judge was telling him that the fact he was an FBI informant was likely to come out; after all the history between him and Bulger and the FBI, Flemmi felt betrayed. He wasn’t alone. Bulger sidekick Kevin Weeks had been serving as a messenger between Flemmi and Connolly, paying Flemmi regular visits in prison. “The information I received from Kevin Weeks from John Connolly was that he was very upset about the situation that Jim Bulger and I were in,” Flemmi said.

What about Ken Fishman?, Wolf asked. Does your lawyer know about any of this?

“I’ll tell him right now,” Flemmi answered. “I don’t have a problem with that.”

“Can I bring him in and do that?”


Flemmi, seeming to grow bouncy, complimented Wolf, offering the judge a wiseguy pat on the back. “Your honor, you’re getting to the core of the matter. There’s no doubt about that. You’re right there. If you go a little further, you could get the whole complete story.”

Fishman returned, and the judge summarized Flemmi’s past, explaining that he’d been given government materials saying Flemmi had been an informant “for many, many years.” Paul Coffey of the Justice Department soon returned, saying, “If the court will let me, I’d like to talk to him.”

Coffey turned to Flemmi and Fishman. “I’d like an opportunity to sit down with both of you someplace and tell you what I think needs to be done.”

“Great,” Fishman replied sarcastically. The lawyer was doing his best to keep up appearances. The disclosure was like a sharp jab that had left him stunned, and even though he’d been around long enough not to reveal how shaken he was, his head was swimming. “After twenty-two years as a criminal defense attorney, you have a visceral reaction, a certain inherent distaste for an individual who has chosen to serve as an informant,” he said.

The lawyer also knew exactly what angle Coffey was working—exploit the shock of the moment, quickly persuade a “back on his heels” Flemmi to enter the witness protection program and testify on behalf of the government against the others.

Coffey went ahead and made his pitch. Flemmi curtly said no. “If I was so valuable to you, what am I doing here?” Fishman was trying to shake loose of his own confused feelings. He wanted time alone with his client. He needed to figure out what to do, and he was soon already thinking about a plan that would turn the “negative information” into a positive. Because the government, Fishman could argue, had “authorized” Flemmi and Bulger to commit crimes in a trade for their underworld intelligence, the mobsters could not now stand trial for crimes they were given permission to commit.

It would become known as the “informant defense,” and to support his claim Flemmi soon began filing sworn affidavits describing his life with the FBI and the promises he said FBI agents had made never to prosecute him and Bulger.

▪ ▪ ▪

On May 22, culminating the months of closed hearings and the legal papers filed under seal, Judge Wolf granted Cardinale’s wish for an open, evidentiary hearing. In a forty-nine-page ruling, Wolf said the purpose of the discovery hearing would be to allow Cardinale and other defense attorneys to question FBI agents and officials about the bureau’s relationship with Bulger and Flemmi so that he could decide whether tapes and other evidence should be suppressed. To that end, the judge said he had decided he had to order the Justice Department to disclose publicly whether Bulger, Flemmi, and the other names included in Cardinale’s original motion had been in fact “secretly providing information to the government.”

The government, noted Wolf, did have other options if it did not want to comply with his order. He acknowledged that his ruling undercut the “generally recognized interest of the government in maximizing the confidentiality of its informants in order to encourage the flow of information from informants.” He said that at times the government “elects to dismiss a case rather than confirm or deny the existence of a cooperating individual.” But, concluded Wolf, if the government wanted to continue against the Mafia and the Bulger gang, it would have to share its secrets.

Wyshak urged Wolf to reconsider, but the judge said no.

Despite the ruling, this team of prosecutors was not about to drop the case. There was no turning back. The Justice Department therefore decided to go ahead and do what no federal official in Boston had ever done: on June 3, 1997, more than two decades after John Connolly first approached Whitey, it confirmed for the court Bulger’s role as a longtime FBI informant.

Paul Coffey uttered the magic words: “I, Paul E. Coffey, being duly sworn, depose and say, that pursuant to this Court’s Order of May 22, 1997, I hereby confirm that James J. Bulger was an informant for the Boston Division of the Federal Bureau of Investigation (FBI).” For now, wrote Coffey, the government was only going to name Bulger, and he explained why, in Bulger’s instance, the decision was made to break from the strict practice of protecting the confidentiality of informants. Bulger, he wrote, “is accused of leading a criminal enterprise which committed serious violent crimes continuously over many years.” It was a crime spree, wrote Coffey, that overlapped with his work as an FBI informant. Moreover, Bulger, as a fugitive, was now trying to escape responsibility for his many alleged crimes. These factors combined to create “unique and rare circumstances,” wrote Coffey, which allowed for outing Bulger in order to put him behind bars. “Bulger has forfeited any reasonable expectation that his previous informant status will remain confidential.”

The Justice Department obeyed the court order, knowing full well that to do so meant allowing Judge Wolf to enter a no-man’s-land. The FBI’s Bulger files were a place where no independent body—such as a federal court—had ever gone before. None of the prosecutors—nor, for that matter, the defense attorneys—knew the extent of that corruption, but they all had a strong sense that opening up the FBI files would get ugly. Paul Coffey had said as much to the judge as the two men were discussing Cardinale’s demands about Bulger and Flemmi: “We see this as a time bomb.”

That bomb, after so many years, was about to go off.