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

PART TWO

I do my best to protect you and I may break a
few rules, but I break them in your favor
.

RAYMOND CHANDLER,
THE BIG SLEEP

CHAPTER FIFTEEN

Connolly Talk

Late Monday morning, February 8, 1988, FBI Agent John Connolly strode out of a hardware store near his FBI office and bumped into Dick Lehr, a reporter for the Boston Globe (and one of the authors of this book). Connolly had been at the store getting some duplicate keys made while Lehr was crossing town en route to an appointment with a source.

It was a chance encounter on a crisp winter day.

Connolly, recognizing the reporter, stopped on the sidewalk to say hello. They didn’t know each other very well, although Connolly was well known by a corps of reporters in the Boston media who covered organized crime as a regular beat. Of all the FBI agents in Boston, Connolly was the most accessible, the agent most eager to talk to the media about his work and the FBI.

Crime was not Lehr’s beat, but he had met Connolly the year before, in 1987. He was part of a team of Globe reporters who spent months interviewing FBI agents from the Organized Crime Squad about the Angiulo bugging. Lehr and the reporters had met with nearly a dozen agents—Connolly, John Morris, Ed Quinn, Nick Gianturco, Jack Cloherty, Shaun Rafferty, Mike Buckley, Bill Schopperle, Pete Kennedy, Bill Regii, and Tom Donlan. The series had been a hit with both the newspaper’s readers and the bureau, for it showed the FBI at its technical best: breaking into the Mafia’s inner sanctum to plant a listening device. Lehr had not seen or talked to Connolly since the newspaper project a year earlier. There was a round of greetings, and then the reporter asked the FBI agent how things were going.

Connolly, jingling the shiny keys in his hand, didn’t hesitate. He began talking about a new FBI bug, one targeting the post-Angiulo mafiosi who were jockeying for position and power. Connolly said that for about six months, from late 1986 to mid-1987, the FBI had monitored the new Mafia lineup conducting business in the back of a grinder shop located in a shopping plaza at the foot of a Boston landmark, the Prudential Tower.

“It was great,” the agent said about the bug that agents installed inside Vanessa’s Italian Food Shop.

Lehr listened intently, realizing right away that the information might make for a great story. But Connolly’s loose manner also took the reporter aback. There was no talk of the conversation being “on background” or “off the record” or restricted in any of the ways information can be when passed along to reporters. To the agent, talking about Vanessa’s seemed to be the same as talking about the Boston Bruins, who the night before had beaten the Calgary Flames, 6–3, to take over first place in their division in the National Hockey League. Or politics. The Democratic Party’s Iowa caucus was under way that very same day, featuring a challenge by Massachusetts governor Michael Dukakis to the front-runner status of Richard Gephardt. Connolly, it appeared, was used to putting tidbits into orbit and not having them traced back to him.

There had been no press coverage whatsoever of an FBI bug inside an eatery in the city’s Back Bay neighborhood. If anything, Boston reporters who covered crime had been puzzling over the status of the Mafia in the aftermath of the 98 Prince Street operation. It was known that a certain amount of Mafia disarray naturally followed the removal of a long-standing Mafia leader like Angiulo, and the names of a number of relatively unknown Mafia figures had begun to circulate. There was Vincent M. Ferrara, who combined a degree in business administration from Boston College with “a taste for blood”; an older mafioso named J. R. Russo; and Russo’s half-brother, Bobby Carrozza of East Boston. Those three men were serving as capo de regimes, or lieutenants, in the struggling Mafia, but not a lot was known about them. In addition, Cadillac Frank Salemme was finally coming home, released from federal prison after serving fifteen years for the 1968 bombing of a lawyer’s car, the assassination attempt for which his accomplice and pal Stevie Flemmi had never been prosecuted.

Outside the hardware store Connolly was buoyant about the bureau’s ability to track the Mafia from its traditional base in the North End to the upscale plaza in the Back Bay. Vanessa’s Back Bay location constituted an altogether new twist, an unlikely spot for the Mafia, churlish bulls in a china shop. Polished shoppers and young urban professionals might be catching a quick bite at the counter while at the same time, in the back room, a fiery Ferrara was spewing vulgar ultimatums to bookmakers as he explained that a new Mafia day was dawning.

The windowless room was isolated and could only be reached by a convoluted route. The gangsters would park their cars in the Pru Center’s underground garage-maze, and no one could follow them without being made. Connolly delighted in the fact that the brazen Ferrara, Russo, and Carrozza all thought they’d found a place to meet that was impenetrable, and he relished the prospect of bringing down Ferrara. Ferrara was “arrogant” and “cocky,” “a real troublemaker.” His peers hated him for his vicious streak and disrespectful way. In fact, noted Connolly, Ferrara would be dead already if word hadn’t gotten around Boston’s underworld that the FBI was after him. The other wiseguys, said Connolly, could “sit back and let us chew him up.”

Subsequently, Lehr teamed up with fellow reporter Kevin Cullen and, after more reporting to confirm Connolly’s account, wrote a front-page piece about Vanessa’s that ran on Sunday, April 17, 1988, and started out, “It was a perfect spot. The cops couldn’t tail you, and you could park your car in the underground garage, walk to a freight elevator and ride up in secrecy.” Though the article included a lot of information, the reporters didn’t have the actual recordings from the Vanessa’s bug. That meant they couldn’t hear Connolly’s favorite recording: Ferrara’s shakedown of “Doc” Sagansky.

“We got a lot of guys in trouble, Doc,” Ferrara told Sagansky. Ferrara was going for the soft touch in his approach to his target, who, at eighty-nine, was the elder statesman in the world of bookmaking. Born at the end of the last century, as a young man Doc had been a practicing dentist, a graduate of Tufts Dental School, but he became a millionaire as the city’s premier bookmaker. By the 1940s police regarded him to be the “financial top man” in the city’s rackets who held ownership interests in two Boston nightclubs and a loan company. In 1941 he’d loaned $8,500 to James Michael Curley, the legendary Boston mayor and then congressman. In return, Sagansky was named a beneficiary in a $50,000 life insurance policy that Curley had taken out as security for a loan. That the two were linked publicly raised a few eyebrows and made headlines. Sagansky’s name had surfaced in every major gambling investigation in Boston since the Depression. In the storeroom of Vanessa’s on January 14, 1987, Ferrara was trying to come off as reasonable with the old man, explaining the Mafia’s hard times—five Angiulo brothers and many other soldiers gone, in jail.

“We have to help ’em,” Ferrara urged. “Their families, lawyers. Some of us are in trouble.” Ferrara wanted Sagansky and an associate who’d accompanied him, another aging bookie named Moe Weinstein, to start paying “rent.” During the regime of Gennaro Angiulo, Sagansky had operated without having to do so. But Ferrara said those days were over, and he wanted a show of good faith in the form of $500,000. He told Sagansky that such a sum was nothing to a millionaire like him, and that Sagansky had “class.” “Help us,” Ferrara said.

Sagansky would not. Even though he was seated in the windowless storeroom surrounded by Ferrara and his muscle, Sagansky tried persuading Ferrara that his gambling business was kaput, that it had “plummeted to nothing.”

Both sides cried poor for a while until Doc had enough. “I’m not gonna give you no bankroll,” he said.

Ferrara exploded. Mob enforcer Dennis Lepore leaned down to get into the eighty-nine-year-old’s face: “You don’t have no alternative. We want something now. And you’re lucky it ain’t more. This is a serious request. You understand?” The venom poured from Lepore’s lips: “What are we playin’, a fuckin’ game here, pal? You reaped the harvest all those fuckin’ years! This is something you’re going to pay now. We want it. We’re not asking.”

To induce cooperation an angry Ferrara then threatened Sagansky that his pal Weinstein would be held hostage until he came up with the $500,000. Doc and Moe were given some time alone in the storeroom. “I’ll never see you again,” Doc said. “Now what should I do?” Weinstein stated the obvious: “Guess you’re going to have to give it to ’em.” The two old men promised to get the money, and Ferrara released them.

The next day, as investigators watched undetected from a safe distance, Weinstein carried a white plastic shopping bag into a restaurant at the Park Plaza Hotel. He handed the bag to Ferrara and Lepore. Inside was $250,000 in cash, the first installment. The two mobsters hurried back to the Vanessa’s storeroom and gloated as they split up the money into six shares of $40,000. “Those assholes, this better be real money,” a flush, cash-happy Ferrara joked to Lepore.

Even without all of the dialogue, the Globe story hit a nerve. FBI officials and federal prosecutors, particularly Jeremiah T. O’Sullivan of the Organized Crime Strike Force, were incensed. Their investigation of Ferrara was still ongoing, and they wanted to know how word about Vanessa’s had gotten out. But the reporters had no obligation or reason to explain to the authorities where their story had started. They were not about to complain about Connolly’s propensity for chatter.

▪   ▪   ▪

In fact it turned out that Connolly wanted to talk a lot about Vanessa’s, or, as it was confidentially referred to, “Operation Jungle Mist.” The agent developed a kind of stump speech in which he described Vanessa’s as the second in a “trilogy” of major Mafia bugs (the first being the 98 Prince Street bug) that the FBI would never have gotten if not for his work with Bulger and Flemmi. “They were without a doubt the two single most important sources we ever had,” Connolly liked to say in a flourish at the end of this proclamation.

But as they so often did, Connolly’s claims upon closer scrutiny proved to be overstated. Bulger and Flemmi were the unnamed informants Connolly referred to during his sidewalk moment with Lehr of the Globe in early 1988. In this regard, it was a shining moment of genuine, singular intelligence. The evidence from the tapes later helped convict Ferrara, Lepore, Russo, and Carrozza of extortion and racketeering. But most of the credit for steering the FBI toward Vanessa’s actually belonged to Flemmi rather than Whitey Bulger.

Even though Vanessa’s was listed in city records as being owned by a couple from the affluent suburb of Belmont, the eatery was in fact controlled by Sonny Mercurio, a Mafia soldier and pardoned murderer. (Later Mercurio himself would become an FBI informant.)

In April 1986 Flemmi began telling Connolly about Vinnie Ferrara, and how Ferrara was working with Mercurio, J. R. Russo, and Bobby Carrozza out of the Italian eatery. Flemmi, not Bulger, was attending the meetings, where the pending business was sorting out the underworld action between the Ferrara faction and Bulger’s gang. Following one meeting in early August, Flemmi explained that Mercurio was “friendly” with him and Whitey Bulger “from the days when he was a messenger and liaison between ‘The Hill’ and Jerry Angiulo.” Flemmi added that Mercurio was in charge of setting up the session between the groups to discuss changing the payoff on the illegal daily numbers games so that they could all rake in even more profits.

Flemmi attended another meeting a week later; afterward he once again provided Connolly with a full account—about the ongoing negotiations to change the payoff odds on the illegal numbers games and about plans to distribute illegal football betting cards during that fall’s football season. He told Connolly, “The Mafia intends to chop up the whole city and state, if possible, by controlling all independent bookmakers.” He reported that the “Mafia was on the march” into the suburbs and said that he’d made his way to the secret session “by taking an elevator up from level 5 to the service area.”

The meetings continued, and Flemmi began providing more details about the storeroom’s location, layout, and security. “The storeroom is located two doors from Vanessa’s,” he told Connolly on August 18, 1986, “which is used for the meet, is wired with an alarm system, but the system does not seem to be operative. In addition to the alarm system, the area is patrolled by a security service.” During one of their late-night huddles at Connolly’s home at the end of August, attended by Bulger and Jim Ring, Flemmi even drew up a rough sketch of Vanessa’s floor plan.

This kind of information provided ample probable cause for the FBI to win court permission to plant a bug inside the eatery’s storeroom—and then some. The diagram, for instance, was somewhat over the top, Ring said later. “I think it’s pretty stupid,” the supervisor said about Flemmi’s artwork. “I don’t need a diagram to figure out how they got in there,” he said. Better to have agents conduct surveillance than give away the FBI’s plans to a criminal informant. “You get too far down a discussion like that with an informant, the informant is learning too much from your questions,” said Ring. “Despite Mr. Flemmi’s great skills,” he added sarcastically, “the people we have are far better, and I relied upon our technicians to put the bugs in the right place so that they functioned.”

By the time the FBI’s bug began on Halloween, Flemmi had, not surprisingly or coincidentally, stopped attending the meetings in the storeroom at Vanessa’s. Once again, the FBI would capture the Mafia while Flemmi and Bulger would remain invisible. “I wasn’t intercepted because I knew it [the bug] was going to be in there,” Flemmi said. Just before the bug began, “John Connolly did tell me it was in.” For months policy meetings at Vanessa’s had involved the two powerful organized crime outfits in Boston, the Mafia and the Bulger gang. But once the FBI tapes began rolling, it was as if Boston was strictly a Mafia town.

The Sagansky shakedown coincided with the arrival of a new special agent in charge of the Boston office. Jim Ahearn, himself a veteran of organized crime cases in California, arrived in November 1986 at the same time the Boston squad was piling up taped evidence against the Ferrara faction. He was immediately impressed by the Organized Crime Squad’s work, and especially by John Connolly, who made sure others knew that the informants behind the bug belonged to him.

To rely on Flemmi at this time, however, the FBI also had to ignore mounting intelligence from other informants about the FBI’s two crime bosses. “Stevie Flemmi, of the Winter Hill gang, has been looking around for numbers agents to take over during the period of [Mafia] confusion and weakness,” one informant told John Morris on April 20, 1986. Flemmi began steering Connolly to Vanessa’s at the same time he and Bulger were moving about the city, flexing their own muscle. “The Winter Hill people are presenting a challenge to the old Angiulo regime, and Flemmi has been all over the city,” the informant went on. “The old Angiulo regime is not in a position to stop Flemmi.”

In this regard, Flemmi’s tip about Vanessa’s proved self-serving, a way to keep a staggered Mafia back on its heels. The FBI could do the dirty work.

Then there was the third in the trilogy of FBI bugs that Connolly would invoke in the 1990s as proof that Whitey Bulger had all-world status. The bugging operation itself, which unfolded on a single night, October 29, 1989, indeed warrants a spot in the FBI’s hall of fame. For the first time ever agents that night secretly recorded a Mafia induction ceremony. Present were Vinnie Ferrara, J. R. Russo, Bobby Carrozza, thirteen other Mafia figures, and, most important, the reigning Mafia boss in New England, Raymond J. Patriarca, son of the deceased Raymond L. S. Patriarca. In the dining room of an associate’s home in Medford, Massachusetts, the band of mafiosi went through their legendary ritual—the pricking of fingers, the sharing of blood oaths—that culminated in the “making” of four new soldiers. It was also a ceremony that was part of the mob’s ongoing effort, post-Angiulo, to ease tensions between competing factions and establish a better working order.

“We’re all here to bring some new members into our Family,” welcomed the presiding Patriarca, “and more than that, to start making a new beginning. ’Cause they come into our Family to start a new thing with us.” One by one the four new soldiers were administered the oath of Mafia office. Each drew blood from his trigger finger for use in the ceremony. “I, Carmen, want to enter into this organization to protect my Family and to protect all my Friends. I swear not to divulge this secret and to obey, with love and omertà.” Each was then told he had become a “brother for life,” and each responded, “I want to enter alive into this organization and leave it dead.”

Carmen Tortora, along with the other three, was also run through a test of loyalties: “If I told you your brother was wrong, he’s a rat, he’s gonna do one of us harm, you’d have to kill him. Would you do that for me, Carmen?”

“Yes.”

“Any one of us here for that?”

“Yes.”

“So you know the severity of This Thing of Ours?”

“Yes.”

“Do you want it badly and desperately? Your mother’s dying in bed, and you have to leave her because we called you, it’s an emergency. You have to leave. Would you do that, Carmen?”

“Yes.”

In the 1990s the famous induction ceremony became an integral part of Connolly’s ode to Bulger. But once again, the facts got in Connolly’s way. FBI files revealed that of the four informants the FBI used for its affidavit to win court approval to record the ceremony, Bulger was not one of them. For probable cause the FBI relied almost exclusively on another of Connolly’s informants, Sonny Mercurio. Sonny had all the hard information about the time and place of the Mafia induction—not Bulger. For his part, Flemmi was used as one of the four informants, but his contributions paled compared to Mercurio’s. In fact, Flemmi later conceded that during the early autumn of 1989 the few tidbits of information he picked up for Connolly came only after the agent told him about the planned event. Until then, Flemmi didn’t know anything about the scheduled Mafia ceremony. “He asked me to monitor all sources and to report to him any information that I obtained, which I did.” Then, once the FBI had captured the ceremony on tape, Flemmi added that he was told about the bureau’s success—a disclosure that may have seemed matter-of-fact to Flemmi but that violated FBI rules. Who told him? “John Connolly,” said Flemmi.

If anything, Connolly’s later stump speech reflected not only a habit for hype but also his knack for embellishing Bulger at the expense of Flemmi. Throughout the years Connolly sometimes filed duplicate reports for each—attributing the same information in the exact same words to both Bulger and Flemmi. The only difference between the two reports would be the typewriters used to write them. Other times the wording wasn’t exactly the same but the information was, and both would get credit. To explain the duplication Connolly said he wasn’t especially careful about how he kept the books and that he considered them one source. “Oftentimes they blurred,” he said. “The information almost came as one.”

The technique benefited Bulger, for between the two, Flemmi was the one with long personal ties to the Mafia. Flemmi, not Bulger, had the juice; he was the frequent visitor inside Mafia dens. Flemmi, not Bulger, was then later able to describe to Connolly the layout and floor plans. Larry Zannino, Patriarca, and other Mafia leaders repeatedly tried to persuade Flemmi to join La Cosa Nostra. But by his “blurrings,” Connolly spread the credit to include Whitey, pumping up—and thus protecting—his old friend from the neighborhood.

▪   ▪   ▪

Tips like Vanessa’s were to be treasured, and unlike the other two FBI bugs cited by Connolly, Vanessa’s was truly the result of working with Flemmi and Bulger. Without their intelligence there would have been no Back Bay bugging of the new Mafia, no extortion of Doc Sagansky.

But by the late 1980s, at what price?

The deal between the Boston FBI and Bulger was by now so out of whack that any good that came the FBI’s way was offset by a wave of concessions and corruption. Of course, such aspects of the deal never showed up in any of the official FBI paperwork—indeed, the annual reviews Connolly and Morris perfunctorily filed always putatively put Bulger and Flemmi on notice that they fell under the bureau’s guidelines just like any other informant. No favors. No license to commit crimes. No looking the other way. For example: “Informant shall not participate in acts of violence or use unlawful techniques to obtain information for the FBI or initiate a plan to commit criminal acts.” Each year Connolly signed an internal FBI memo saying he’d given this and ten other “warnings” to Bulger and Flemmi, including, “Informant has been advised that informant’s relationship with the FBI will not protect informant from arrest or prosecution for any violation of Federal, State, or local law, except where the informant’s activity is justified by the Supervisor of SAC pursuant to appropriate Attorney General’s Guidelines.” And in all the FBI’s files on Bulger and Flemmi, covering hundreds of pages over two decades, no documents ever surfaced showing that the mobsters’ crime spree was authorized.

Instead, Connolly and Morris and the Boston FBI office had fashioned a side deal, a fine-print, invisible-ink addendum of sorts. It was simple and relatively straightforward. It called for agents to commit crimes to protect the two informants. Up had become down.

Sometimes the FBI protective zeal extended beyond Bulger himself to include sidekicks on Bulger’s rim. Bars on the lower end of West Broadway were letting out in the early morning hours of Mother’s Day 1986. A pop-pop of gunshots rang out, and in a car parked across from the entrance of Triple O’s, Tim Baldwin, twenty-three, of South Boston, an ex-con who’d just gotten out of jail, slumped forward, dead.

Within days Boston Police homicide detectives had a suspect—twenty-six-year-old Mark Estes, another ex-con who’d been drinking inside Triple O’s just prior to the killing. Police learned that two weeks earlier Baldwin had beaten Estes with a tire iron in a dispute over a girlfriend. Police had eyewitnesses to the shooting among the hundred or so people spilling out of the bars at closing time. The witnesses told police they saw Estes shoot Baldwin, saw Estes shoot at bystanders as he fled, and saw Baldwin commandeer a car driven by a woman in a futile attempt to escape.

But at a court hearing in late June the case against Estes hit a big-time snag. The witnesses recanted their identification. The murder charge was dismissed, and afterward police complained about the long-standing neighborhood “code of silence”: residents would balk at cooperating with the authorities. “I’m from South Boston,” shrugged one of the witnesses, trying to explain the turnabout to the judge. “We keep things to ourselves.”

Prosecutors vowed to continue a grand jury investigation, and by Labor Day a subpoena to appear at the grand jury was issued to Kevin O’Neil. The Bulger protégé had been running Triple O’s the night of the murder, and Sergeant Detective Brendan Bradley of the Boston Police homicide squad said he had gotten information that O’Neil “knew all the details of the murder, including the name of the perpetrator.” Prosecutors wanted O’Neil to go before a grand jury and give them Estes.

But the Bulger gang and the FBI saw the subpoena differently—as a nuisance. Bradley came into work on September 5, 1986, and found a telephone message. FBI agent John Connolly had called. Bradley returned the call. “Connolly said that he wanted to talk.” They agreed to meet for coffee three days later in the lobby of the John F. Kennedy Federal Building, where the FBI had its Boston bureau.

Bradley arrived first. “Connolly came out of an elevator carrying a cup of coffee for himself.” The agent was apologetic that his other hand was empty, saying, “The girls in the office love me and always buy me coffee.” What’s a popular guy to do? The two investigators went and got Bradley a cup and huddled off to the side. “What are you doing to my friend?” Connolly asked the cop.

The agent explained that he knew all about the subpoena served on O’Neil. O’Neil, said Connolly, was from a good South Boston family, and his brother was an injured Boston firefighter. He was “a good shit.”

Bradley explained that they were talking about a murder investigation, and O’Neil could apparently help the police. Connolly was unmoved. “But he’s a good guy.” Besides, he said, the dead man was “a piece of shit.”

The message was simple: a “good shit” beats a “piece of shit” any day.

Connolly did not “ask directly to withdraw the subpoena to O’Neil,” but Bradley left with the impression that “that was the purpose of the conversation.” O’Neil eventually did appear before the grand jury, but he refused to testify. He cited his Fifth Amendment privilege against self-incrimination. Homicide detectives chased other leads; nothing broke, and the investigation fizzled. Estes was a free man.

Immediately afterward Bradley told a colleague and two homicide prosecutors about the disturbing lobbying on behalf of a Bulger protégé, apparently to “squash a grand jury subpoena.” Years later one of the prosecutors said that he did not recall Bradley complaining about Connolly. John Kiernan, a self-described friend of Connolly’s, said he did not “believe Connolly would ever do such a thing.” But the other prosecutor clearly recalled hearing from Bradley right after the detective had had coffee with the FBI agent.

James Hamrock said he had actually considered subpoenaing Connolly to the grand jury “to testify about his role and knowledge of the matter.” But to avoid worsening the already poor relations between the FBI and local prosecutors, Hamrock did not. Like others before him, he let the Connolly talk go.

▪   ▪   ▪

In terms of FBI housekeeping John Connolly was not acting alone in keeping the Bulger house in order. John Morris was now the supervisor of a white-collar squad that mainly pursued public corruption, and in early 1985 he was running an investigation that had started as an organized crime case. The original targets were two veteran bookmakers operating in the Roxbury section of Boston, John Baharoian and Steve Puleo. Baharoian ran a gambling business out of his run-down Avenue Variety on Blue Hill Avenue. The shelves were stocked with dust and goods with expired sale dates.

Investigators knew the convenience store was a front for one of the busiest bookie joints in that part of the city. They also believed that Baharoian paid tribute to Flemmi. But then investigators began to develop evidence that Baharoian was also bribing several Boston Police officers for protection. Once that happened, the case was transferred to Morris’s squad, with an expanded focus on the police corruption.

In the late winter of 1988 agents working for Morris were putting together a plan to install a wiretap on Baharoian’s telephone. Morris’s unspoken worry was that Flemmi—and possibly Bulger—would be caught on the tape. It was a possibility that stoked his worst fear—an arrest of Bulger and Flemmi leading to his own apprehension if the mobsters, looking for leniency, turned and traded him in. He decided he’d have to warn them off.

Morris told Connolly about the imminent danger, that Flemmi and Bulger needed to stay off the telephone and stay away from Baharoian. They should call a meeting, replied Connolly. Connolly, recalled Morris, “thought they would like to hear from me. He wanted me to give them that information as opposed to him giving them that information, or meet with them at least to discuss it with them personally.”

Fine, said Morris. The four could meet. But there was one other worry haunting Morris. Even if these circumstances were not exactly the same, Morris knew that on a prior occasion when he’d disclosed a secret investigatory effort to the group, the outcome had been bad, chillingly bad. “I don’t want another Halloran,” Morris told Connolly.

Connolly made arrangements for another get-together, this time at the Lexington town house Morris had moved into. It seemed that on every front Morris’s life was bottoming out: his marriage was torn beyond repair, and he was worried sick about his teenage daughter. But as troubled as Morris was, Connolly just cruised along. Bulger and Flemmi seemed fine too. They had certainly come to expect this sort of input—tips about investigations, wiretaps, bugs, and the names of other wiseguys who were cooperating with the police. “As the need arose and I was in a certain situation,” said Flemmi, “I would ask him [Connolly] a question regarding certain people, and he would advise me.” It was as if the two agents were serving as their consiglieri, the Mafia’s term for advisers.

But Morris’s own reasons for protecting Bulger and Flemmi had multiplied. He was desperately looking to cover himself. “I was completely compromised at that point, and I was fearful that Mr. Flemmi might be intercepted, and that would be the beginning of the unraveling of what in fact had transpired between myself and them,” Morris said. He knew he was breaking the law—obstructing justice. “I believe that the Baharoian matter clearly was a violation of regulations.” But he saw his own neck on the chopping block if agents caught Flemmi or Bulger on tape. Connolly, Bulger, and Flemmi arrived at the town house, and Morris got right to it, telling the two informants “that we had already started a Title III on Baharoian, and I warned them to avoid Mr. Baharoian.”

Flemmi appreciated the heads-up. “Morris said that he could keep me out of the indictment, but he couldn’t do the same for other participants in that operation, meaning Baharoian and Puleo.”

The FBI’s wire on Baharoian was up from June 22 to September 26, 1988. That wiretap and other evidence resulted in the indictments of Baharoian, Puleo, and several Boston Police officers. Baharoian eventually flipped and testified at trial against the police. Tapes were played, featuring the voices of bookies and cops. But not Flemmi’s. Not Bulger’s. They knew when it was safe to talk, and when to keep quiet.