Black Mass - THE BIG SLEEP - 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)


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



Black Mass

Tight lipped and intense, the John Morris of 1985 was still enjoying the glow of having overseen the successful bugging of Mafia headquarters in early 1981. He was viewed as a seasoned veteran, thoughtful and determined. He was also leading the double life of a libertine, as were the other members of the cabal—John Connolly, Whitey Bulger, and Stevie Flemmi. Each had a public pose that contrasted sharply with a private reality. Morris and Connolly were FBI agents by day who at night caroused with the two gangsters they now zealously protected, even if it meant bending rules and breaking laws. Bulger and Flemmi feasted off reputations as the ultimate stand-up guys who cunningly outwitted the police at every turn, when in fact they had for years given the FBI tidbits about underworld friends and foes and enjoyed a protective shield from the nation’s top law enforcement agency.

Morris was essentially in Bulger’s back pocket—having solicited and taken $1,000 in 1982 to fly Debbie Noseworthy to Georgia. And during the early days of 1984, amid the start-up of the DEA’s Operation Beans, Morris had taken a second bite from the apple Bulger held out for him.

“Connolly called me and said, ‘I have something for you from these guys. Why don’t you come on over and pick it up?’ I went over; I picked it up. It was a case of wine. On the way out he said, ‘Be careful with it, there’s something in the bottom for you.’ So I took the case of wine, and then when I opened the case I found that there was an envelope on the bottom that contained $1,000 in it.” It was as if Morris needed more moments like this one to keep the high going. The concern was not whether he should march into the office of the special agent in charge of the Boston office and turn them all in; instead, his narrow eyes darted this way and that to make sure no one was watching. He picked up a corkscrew, opened a bottle, pocketed the Bulger money, and savored it all.

But if Bulger saw the case of wine as a second premium on his FBI insurance plan, he was suddenly disappointed. The FBI that considered Morris a model of integrity dispatched the supervisor off to Miami to oversee a special team of agents investigating—of all things—the corruption of an FBI agent in Florida. The timing was horrible, given the detectable increase in scrutiny Bulger and Flemmi were getting from the drug agents and the Quincy Police. Throughout the remainder of the year and into early 1985 Bulger and Flemmi weathered Operation Beans with the help of Connolly and, to a lesser degree, Jim Ring. It had not been easy, however, and now that federal drug agents were stymied and John Morris was resurfacing, it seemed like the time for a reunion. Time to clarify their secret alliance over a good meal. Time to review some old business—Operation Beans—as well as discuss pressing new concerns, such as the long-delayed, upcoming racketeering trial of the Mafia’s Gennaro Angiulo, featuring the FBI’s extensive tape recordings of Mafia talk at 98 Prince Street. The trial—the biggest criminal trial in Boston in decades—was finally due to start any week, and Bulger and Flemmi had a list of worries about the tapes.

Going into the dinner Connolly had already disclosed the fact that Mafia leaders Jerry Angiulo and Larry Zannino often got to talking on the tapes about Bulger and Flemmi—“conversations,” said Flemmi, about “different criminal acts.” Of particular concern to Flemmi was the Mafia talk about his role in the 1967 slayings of the three Bennett brothers. But there was plenty more. Connolly provided a full telling of the wiseguy dialogues. “The Bennetts were mentioned on the tapes,” Flemmi said, and John Connolly also “mentioned the gambling, if I can recall, some bookmakers on there that were—that we were involved with. I think Jerry [Angiulo] mentioned the fact that Whitey had all of South Boston, Stevie had all of the South End, and we were extracting X amount of dollars from bookmakers. He mentioned an amount—Whitey probably gets … $50,000 a week from extracting payments from bookmakers.”

Flemmi and Bulger were alarmed. Prior to the 1981 bugging of the Mafia, this was the exact situation Bulger and Flemmi had voiced concern about—that even if they avoided appearing at 98 Prince Street the Mafia bosses would nonetheless talk about their mutual business interests. They needed reassurance of a promise Morris and Connolly had made at the time, that in return for their help against Angiulo the tapes would not be used against them.

While Morris was off in Miami, the gangsters had talked all of this over with Connolly, asking the FBI handler about the precise danger the tapes posed to them. Connolly tried comforting them. “That’s when he said not to be concerned about it,” Flemmi recalled. But better to hear the same from Morris, to have the promise restated.

“The meeting was set up by John Connolly,” Flemmi recalled. Connolly got in touch with Bulger, and Bulger lined up Flemmi: “We just became available.” They picked a weekday night in early spring. The city was emerging from the darkness of winter, and the weather was mild, hinting at summer. Connolly picked up Bulger and Flemmi in a South Boston parking lot. He said another old friend would be joining them, Dennis Condon, the former FBI agent who’d been with them all at the start of their deal in 1975 and was now a high-ranking public safety official overseeing the state police. Condon was an elder statesman, a veteran of FBI tricks from the 1960s. “They knew each other,” Morris recalled, “and Connolly and I felt that Condon would enjoy the opportunity of seeing them.” It went without saying that having Dennis Condon attend what was essentially a fifty-thousand-mile checkup in the FBI’s Bulger deal made sense. Condon was ex-FBI and now sitting atop the state police, and Bulger and Flemmi were constantly distracted by the attention they were drawing from other police agencies. Why not try to touch as many bases as possible?

Driving into the rush-hour traffic, Connolly, Bulger, and Flemmi headed out of the city for dinner with John Morris.

▪ ▪ ▪

Morris, meanwhile, was busy puttering around the kitchen of his Lexington home. He seasoned the steaks and got the meat ready for the oven. He set the table in the dining room for five. His wife Rebecca would not be joining them. “I refused to cook dinner for them,” she said later. John might be upbeat about his dinner party, but his wife was downcast. They circled one another in the kitchen, wary and mistrustful. Her head shaking, she voiced again her strong opposition to having two gangsters in their home—what about their son and daughter? John tried calmly to explain again the necessity of maintaining Bulger’s and Flemmi’s trust. Rebecca knew nothing about the Bulger money or any of the other peculiarities of her husband’s ties to the crime bosses. But she knew something wasn’t right. Rebecca had been an FBI wife long enough to sense that something was irregular about the long-running arrangement.

So she would have none of it. John might try to soften the terms of the disagreement by always referring to Bulger and Flemmi as “the bad guys,” a kind of concession to her that he never forgot who Bulger and Flemmi were and that, rest assured, he knew exactly what he was doing by having them over. He even tried saying he was actually concerned about John Connolly and Connolly’s closeness to Bulger and that he, as Connolly’s friend and former supervisor, had a duty to keep an eye on things. But Rebecca was not impressed. She didn’t want them or their gifts in her house.

The maple trees in the yard were sprouting buds, and inside the kitchen John Morris was doing his best to let the marital tension drain from him. He was feeling pretty good otherwise, riding a professional high from the Florida special assignment he was in the process of wrapping up. Morris thought about what he’d done down South. The agent he’d investigated, Dan Mitrione, had been considered a role model—smart, always physically fit, an ex-Marine and Vietnam vet with solid law enforcement blood-lines. He was the son of a former police chief and State Department employee who had been murdered by terrorists in Uruguay in 1970. In the early 1980s Dan Mitrione had begun working undercover as part of a major FBI drug investigation. He worked his way into the inner circle of a major cocaine cartel but fell under the spell of the key smuggler, an older man who began treating Mitrione like a son. Mitrione eventually began aiding the smugglers he was supposed to catch. By 1984 he was under investigation.

John Morris was in charge of a team of FBI agents assembled from around the country and sent to unravel the mess. By the fall of 1984 Mitrione had confessed to the special task force that he’d taken $850,000 in bribes from the drug smugglers. He pleaded guilty in federal court and was sentenced to serve a decade in prison. The federal judge, at his sentencing, was clearly dismayed at the undoing of an agent with such an exemplary career. “The Lady of Justice may have a blindfold on, but she also has a tear on her cheek today,” the judge said from the bench.

Morris had come home to applause from superiors for a job well done. But it had to be an eerie experience. He’d gone off to Florida within weeks of accepting wine and $1,000 from Bulger. He realized that the dirty money he had taken amounted to chump change compared to Mitrione’s eye-popping $850,000. But imagine the fallout if the FBI brass realized they had sent one corrupt agent to investigate another. And there were other secrets to keep, including hiding from Rebecca the romantic affair with his secretary, Debbie.

The husband and wife maintained their big chill in the kitchen of their suburban home when, around seven o’clock, the doorbell rang. The special guests had arrived. Rebecca stiffened. John surveyed the kitchen, saw the meal was coming along fine, and headed to the front door. “I felt that my house was a very safe place,” Morris said about hosting gangsters at his home. “I did not think that they were an immediate threat to my family. I was concerned later on about them knowing where I lived, but at the time I was not concerned for the safety of my wife and children.” It would be good to see Connolly, Bulger, and Flemmi again. He had already picked up talk from the office that the group was not all that happy with Jim Ring.

Morris pulled open his front door. He heartily greeted his guests. There were handshakes all around. Welcome, welcome. The gangsters had brought along not just wine but a bottle of champagne as well. John Morris and Flemmi headed into the kitchen to put the bubbly on ice. Rebecca Morris stood at the sink washing her hands. The moment Flemmi entered her kitchen she turned off the water and abruptly left the room. Morris shrugged. He turned his attention to his guests, offered a thin, wan smile, and asked how things were.

▪ ▪ ▪

The trio of Connolly, Bulger, and Flemmi was just as happy to see Morris as Morris was to see them. Especially Connolly—Jim Ring had been a tough mark. Connolly had tried his best to get off on the right foot by arranging get-togethers so everyone could get to know one another. (“John Connolly came to me and used the expression, ‘The boys want to meet with you,’” Ring said later.) But Ring had studied Connolly, grown increasingly concerned at the agent’s breezy style, and was left momentarily speechless at the end of the dinner at Mrs. Flemmi’s house when, “as we were leaving, Whitey Bulger’s brother, Bill Bulger, came into the kitchen to give him some photographs.

“What the hell is going on?” Ring blurted at Connolly afterward about the pileup of breaches in protocol—the casual dinner atmosphere with two crime bosses, the involvement of an informant’s mother, the entrance of one of the state’s most powerful public figures. No one in the room had even blinked—one big happy family. Connolly didn’t understand Ring’s question. He simply pointed out to his supervisor that Bill Bulger lived next door—that was the explanation for the unexpected drop-in.

Ring’s dismay had culminated in private sit-downs with the Boston office’s star handler of informants. The supervisor’s list of grievances covered just about every basic ground rule the FBI or any police agency had on how to work informants. “I had a meeting with John Connolly in my office,” Ring said later, “and I told him that what I was observing was contacts with Mr. Flemmi and Mr. Bulger with mistakes made that a first-year agent wouldn’t make.” Ring complained that Connolly’s friendly manner was way over the top, that instead of treating the two informants as criminals he treated them as if they were colleagues at the FBI office.

Ring immediately noticed that information was flowing the wrong way—to Bulger and Flemmi. Connolly, Ring said, “gave away too much. He could have rephrased the question in a different way. You could have buried the question among five others, and the one thing—I think it was the second meeting—that struck me was Connolly turned to me and said something to the effect, ‘Oh, tell them about such and such.’”

The meetings at Connolly’s home in South Boston were also a problem. “It was crazy,” Ring said. He ordered Connolly to stop hosting Bulger and Flemmi at his home. Connolly responded like a merry schoolboy prankster determined to fool the stern, humorless schoolmaster. He sought out another agent, John Newton, and asked if he could move the gatherings to his South Boston apartment. Newton, the agent Connolly had befriended upon his arrival in Boston, was happy to help. Newton opened up his home to his FBI friend, and when they all showed up for these unauthorized encounters, Newton would take his two dogs out for a stroll. The considerate Bulger eventually began bringing along dog biscuits.

Connolly then reported back to Ring that he’d obeyed the order and halted the practice of meeting at his house. But word got to Ring that Connolly had simply pulled a fast one, relocating down the street. “Un-professional, stupid, not the way business is done by FBI agents. I was just not happy,” Ring said. “Why go into a neighborhood where two people are known? You can go to New York City. You can go to Canada. Go someplace. This is being lazy.”

And Ring didn’t even know about the dinner parties—at Nick Gianturco’s house, at John Morris’s house. In addition, Ring noted that seeing two informants together—an accepted fact at this point in the history of the FBI’s deal with Bulger and Flemmi—was highly irregular. “If you could control the situation,” noted Ring, “you’d meet Bulger and Flemmi separately.” But of course the FBI was not in full control.

In response to Ring’s criticisms Connolly unleashed his well-rehearsed defense of Bulger and Flemmi as indispensable to the FBI’s war on the Mafia. Included was Connolly’s patented story that pulled the heartstrings of every FBI agent—how Bulger and Flemmi had saved Nickie Gianturco’s life.

But Ring even had the gall to question this piece of Bulger hype. Rather than take Connolly at his word, he went and asked Gianturco about the tale. “I asked him, what was the story? And he went back and related that there was this undercover operation which he had been in, that there was some scheduled meeting he was supposed to attend, and that reportedly Mr. Bulger and Mr. Flemmi had sent him information warning him not to attend.

“I was saying to him: ‘You didn’t answer my question. My question was, “Are you reporting to me that you believe that these two people saved your life?”’ And I recall his response being that the case was over.” Ring never got a straight answer.

For all of his concerns, Ring kept the matter between himself and Connolly. He did not document his criticisms or share his concerns at the time with any of the other FBI supervisors in the Boston office. He did not discipline Connolly. Ring didn’t think discipline was warranted “for doing something stupid. What I thought I needed to do was to manage the people that I have and start doing that.” Instead, Connolly’s personnel files continued to fill with glowing reports about his work.

No surprise, then, that in the spring of 1985 at Morris’s house Jim Ring was not standing in the kitchen alongside Bulger, Flemmi, and Connolly. In fact, around the time of the dinner Ring and Connolly had even discussed the issue of “Mr. Bulger and Mr. Flemmi not liking me,” recalled Ring, “and my position being I really didn’t care, because they were informants.” But Morris did care about being liked—by everyone.

▪ ▪ ▪

“Connolly, Flemmi, and Bulger had arrived together,” Morris recalled. Dennis Condon showed up thirty minutes later, around 7:30 p.m. He had driven directly from his executive office at the state Public Safety Department in Boston. Morris hustled from living room to kitchen, the dutiful host and cook.

The men headed into the dining room. It had been years since Bulger and Flemmi had seen Condon. The night in Lexington marked “the first meeting that I’ve had since 1974 with Dennis Condon,” Flemmi recalled. The year 1974 had certainly been a pivotal one for Flemmi. He’d returned to Boston after spending nearly five years on the lam, a forced departure triggered by his indictment in 1969 for a car bombing and the William Bennett murder. Flemmi believed that Condon had paved the way for his eventual return from Canada by seeing that the two major felony charges were dropped along with a third charge that had been added as soon as he fled the country to avoid prosecution. After Flemmi’s return there had been the get-together with Condon at the coffee shop as part of his hand-off to the very useful Connolly. In Flemmi’s eyes Condon had been the stage manager behind many of these moves, and he was grateful. “I hadn’t seen him for quite a while. I asked him how he was doing, how he felt. I thanked him for disposing of the federal flight warrant that I had. I asked him how Mr. Rico was, who was a partner of his, and I says, ‘If you ever have the opportunity to see him, say hello for me.’”

The men took their seats at the table. Morris served up the steak. The men poured more wine. For the first hour or so they chatted about old times.

“It was light banter,” Flemmi recalled. Bulger recounted stories from his time in federal prison during the late 1950s for robbing banks. “Most times he does most of the talking,” Flemmi said about Bulger. “Quite a variety of subjects. He’s very knowledgeable, very intelligent. He kind of captivates his audience.”

But if Bulger was a chatterbox, Condon was not. The graying veteran of Boston’s law enforcement circles sat there picking at his food and listening politely. He felt ambushed, he said, surprised to find Bulger and Flemmi in Morris’s home. He’d gotten his invitation during a telephone call late in the afternoon—c’mon and swing by on your way home. He said that all he’d been told was that Morris and Connolly were going to be there “and a couple of people were coming by, and they’d like to say hello.”

Of course there was an outward collegiality to the occasion, the appearance of a simple gathering of old friends sharing wine and war stories. But beneath the easygoing veneer were pressing concerns that Bulger and Flemmi had about their protection. In a way each law enforcement official present at the dinner was a symbol of the history and the scope of the alliance. The past, the present, and, they hoped, the future were represented at the table in Condon, Morris, and Connolly. But Condon, who potentially covered two police agencies—the FBI and the state police—was hardly having a regular old time. Morris said about Condon, “I could tell from the way he looked when he came in … he didn’t look real comfortable.”

“I thought that it was extremely unusual that Mrs. Morris was there and I was there, and neither of us at the time were members of the FBI,” said Condon. “I also felt that in the position that I occupied I shouldn’t have been there.”

Dennis Condon did not protest to anyone at the time, did not pull Morris and Connolly aside and ask for an explanation. “I hung in there for, I would say, for politeness and diplomacy.” (He would also keep the dinner a secret, telling no other official about it for at least another decade.) But the others at the table that night got no hand-holding from him. Finishing his food, Condon made his exit less than sixty minutes after he’d arrived. Flemmi was taken aback. To him, Condon “didn’t seem to be uncomfortable,” and he was sorry to see him leave.

The party was now minus one.

Even so, Bulger and Flemmi still had Connolly and Morris at hand. They poured more wine and got down to business.

John Connolly, Flemmi said later, provided updated accounts on who the two crime bosses should avoid in their underworld activities. He disclosed the identities of several police informants. The talk then turned to the upcoming Mafia trial, the FBI’s tapes, Bulger’s possible vulnerability, and, most important of all, the keeping of promises the agents had made.

“I don’t know who raised it,” said Flemmi. “We were concerned because we believed our names would be, during conversation at Prince Street, would be mentioned regarding criminal matters.

“I knew at that particular time there was conversation on them wiretaps between Jerry [Angiulo] and Larry [Zannino], and they were discussing Jim Bulger and myself. I was concerned about them at some point in time being used against us. I asked John Morris and John Connolly about that. And they said to me that that would be of no concern because I was not going to be prosecuted for anything that would be on those tapes.

“Well, when we were discussing the tapes, the flow from that conversation led into a statement that John Morris made to me and Jim Bulger.”

It was better than any promise Morris and Connolly had ever made to them. Morris, his wine nearby but clearly sober, said, “You can do anything you want as long as you don’t clip anyone.”

Flemmi liked what he heard. “I said to John, I says, well, I says, ‘John, can we shake on that?’ And he says, ‘Yes.’

“And we shook hands, and Jim Bulger shook hands.”

They had finally reached a champagne moment.

▪ ▪ ▪

The dinner lasted three hours but did not run late. Bulger, Flemmi, and Connolly drove away around 10:30 p.m. Morris tidied up before heading off to bed.

Condon may have departed prematurely, unable to enjoy the highlight of the night, but Bulger and Flemmi nonetheless left feeling pretty good. The gangsters thought their FBI agents had sanctioned what they did best: committing crime.

“That’s the way I interpret it,” Flemmi said later of the wonderful life he’d been promised. “Short of murdering someone, I think that, yes, they could give that kind of assurance.”

In Flemmi’s mind the two agents had reaffirmed a group protection policy featuring a full menu of services: snuffing out trouble before an investigation could even get going, as the agents had done in the past in matters involving the Melotone vending machine executives, Frank Green’s extortion, the many unsolved murders, and the takeover of the Rakes family liquor store; tipping them off to wiretaps against them, as they had done in the state police’s Lancaster Street garage case and, most recently, the DEA’s Operation Beans; pulling them out of any indictment that actually made it to the development phase, as they had done in prosecutor Jeremiah O’Sullivan’s horse race-fixing case; and finally, if all else failed and Bulger and Flemmi were actually facing indictment, giving them a head start.

It was as if at the tenth anniversary of their secret deal they all renewed their vows. Bulger and Flemmi could leave the table feeling recharged. Ring might be unpredictable and therefore unreliable, but they could count on Morris and Connolly. The timing for this revived good cheer turned out to be fortuitous too. Though no one realized it that night, another Bulger, brother Billy, was about to have his own need for a friendly FBI.