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 TWELVE

The Bulger Myth

Detective Dick Bergeron of the Quincy Police Department pulled himself closer to the manual Royal typewriter that sat atop his gunmetal desk. Typing was not his calling in life; working the streets, stalking gangsters was. He shifted uneasily in the chair and then pecked at the keyboard.

The detective typed the words: “TOP SECRET.”

He typed the words: “SUBJECT: Proposed Targets of Investigation for Sophisticated Electronic Surveillance.”

He typed the names of the two targets:

I.

James J. (AKA “Whitey”) Bulger.

 

d/o/b: 09-03-29.

 

ssn: 018-22-4149.

II.

Stephen Joseph (AKA “The Rifleman”) Flemmi.

 

d/o/b: 06-09-34.

 

ssn: 026-24-1413.

It was June 19, 1983, and scattered across Bergeron’s desk were stacks of notes and surveillance reports. Bergeron was shuffling through the material to compose a seven-page, single-spaced report for his Quincy Police superiors about the two “notorious organized crime leaders.” The time had come for the cops to do something about them.

Bergeron had been watching Bulger and Flemmi for months. Bulger, he had learned, was not just the boss of illegal rackets in South Boston but now controlled organized crime in the city of Quincy and “beyond into the South Shore.” Moreover, by following Whitey, Bergeron and the other detectives in his organized crime unit had learned that Bulger had now moved right into their midst. As Bergeron wrote, “Subject Bulger is residing in a condominium at 160 Quincy Shore Drive, Quincy, which is located in a luxury apartment complex called Louisburg Square. The apartment or unit number is 101.” The condo, he’d found, was not listed in Bulger’s name. The owner was Catherine Greig, a Bulger girlfriend. The purchase price for the unit in 1982 was $96,000—cash, no mortgage. “The shades in said unit are usually pulled down, and cardboard is taped to the small windows in the outside entry doors.” (Unknown to Bergeron at the time was the condo’s eerie proximity to a gravesite. The new address was just about a hundred yards away from where Bulger and Flemmi, eight years earlier, had buried the corpse of Tommy King along the banks of the Neponset River.)

The cops had learned that Bulger ran the rackets in Quincy and was now often spending his nights there—reason enough to take action against him. But Bergeron had come up with an intriguing and altogether new twist about the crime boss. By consulting with his own network of underworld informants, Bergeron had learned that Bulger and Flemmi “now appear to have broadened their horizons into drug trafficking.” With their “expansion into the drug market,” wrote Bergeron in flat, official prose, “they will be helping people destroy their lives.”

Bergeron finished typing his report, handed it off to his boss, and returned to the street. He and other detectives continued to follow Bulger as the gangster moved between their city and South Boston and as he met regularly with Flemmi, a few other select gangsters, and George Kaufman, the associate who often served as a front for them as the owner of record of their garages. In early 1984 Bergeron watched Bulger and Flemmi replace the sign out in front of the liquor mart at the rotary with a new one: South Boston Liquor Mart.

Eventually Bergeron’s written proposal worked its way through various law enforcement channels, landing at the federal agency specializing in drug cases, the DEA. Bergeron’s report was consistent with the DEA’s own intelligence. The DEA had busted a major drug dealer, Arnold Katz, who had told DEA agents about Bulger’s business ties to another major drug trafficker, Frank Lepere. Lepere was the dealer the state police had seen with Bulger at the Lancaster Street garage during surveillance in 1980. Now Katz was disclosing to the DEA that during the early 1980s Lepere had forged an “alliance with Whitey and his partner, Stevie Flemmi, in which Lepere agreed to pay Whitey and Stevie whenever he smuggled a load of narcotics in return for protection.” Katz said Lepere had told him all about the deal himself, including how he delivered cash payments to Bulger in a suitcase.

The DEA had more. Early in 1981 a confidential informant had reported that Bulger and Flemmi were on the move—“attempting to control drug trafficking in the region by demanding cash payments and/or a percentage of profits for allowing dealers to operate.” With the arrival of the secret Quincy police report, two DEA agents, Al Reilly and Steve Boeri, were assigned to work with Bergeron. Reilly and Boeri quickly added to the growing pile of Bulger intelligence. In February 1984 Reilly met with one of his informants, named “C-2” in DEA reports, who told him that coke dealers were complaining about having to “pay protection money to Whitey.” The informant identified a pub owner in South Boston who paid Bulger for the right to sell “small quantities of cocaine and heroin from the bar.” Then Agent Boeri met with one of his informants, called “C-3,” who’d known Bulger for two decades and said the ambitious gangster “most recently” had taken control of “drug distribution in the South Boston area.”

The drug theme was reiterated by “C-4” as well as other underworld sources, and by early 1984 the pieces were falling into place for a joint investigation into Bulger’s drug activities. The case, called Operation Beans, would mainly involve the DEA and Quincy detectives.

It had come from bottom-up police work, especially through the often mind-numbingly tedious efforts of Bergeron and his colleagues. Piling up night after night of surveillance throughout 1983 and early 1984, Bergeron had learned a lot about Bulger. Going through the trash at the condo, Bergeron might find a grocery list intact, in Greig’s swirling cursive handwriting—“asparagus, chicken breasts, sherbet, ricotta cheese, olive oil”—but he’d also find Bulger’s papers torn into tiny pieces or burned to ash. He’d learned that Bulger was “habit-oriented”—leaving the condo in Quincy at about the same time each afternoon for dinner at Teresa’s house in South Boston. Then a full night of secret business meetings, mostly at the liquor mart. Then home to the condo. If it was sunny the next day, he’d often appear on the second-floor patio in the early afternoon for a breath of fresh air, sometimes still clad in pajamas.

Bergeron uncovered a man leading two lives. It was apparent that Teresa did not know about Catherine. But besides his women, Bergeron was witness to another Bulger double-cross—one against his neighborhood. Bulger had an iron grip on drugs moving through South Boston and beyond. He made dealers pay “rent” on every gram of “Santa Claus,” a Southie code name for cocaine. He extorted a share of everything from nickel bags to kilos, loose joints to burlap-wrapped bales of marijuana. Just across from the liquor mart certain apartments in the Old Colony project, a project near where Bulger had grown up in Old Harbor, had visitors tapping at the door at all hours of the day and night. Young men, even some mothers, were selling drugs out of the homesteads—angel dust, mescaline, valium, speed, coke, and heroin—and nothing moved without Whitey’s okay. (Paul “Polecat” Moore, one of Bulger’s underlings in the drug business, kept a place in Old Colony.) Bulger might often refer to drugs as “fuckin’ shit,” but his disgust didn’t stop him from making big money off the drug trade, which smoked hotter in the two projects at the rotary than it did in the more middle-class streets of City Point. It got to where “P-dope,” a heroin mixture, cost only four dollars a hit—cheaper than a six-pack.

It would take another decade before the code of silence began to break, when victims’ groups would sprout up and begin pushing back against the Bulger tide, when social workers would hit the streets to take hold of the neighborhood kids and urge them to quit snorting coke and shooting up the heroin, when former addicts would stand up. There was the Southie eighteen-year-old who openly described how he hadn’t seen his dad in eight years, how his mother had died from an overdose, how he’d even tried once to hang himself in the hallway of his project. But after all that, he actually considered himself lucky: he hadn’t shot up in fourteen months. There was a nineteen-year-old named Chris who described his seven years lost to drugs—a spiral that began with booze and pot, then LSD, coke, and heroin. He’d served time but was now determined to go straight. “There’s nothing out there for me if I go back, nothing but a grave with my name on it.” Patrick, a thirty-nine-year-old recovering addict, talked about the slippery slope that teen junkies followed: “When they’re fourteen or fifteen, they start out snorting it. They’ll say, ‘I’d never stick a needle in my arm.’ Then, once they do that, they’ll say, ‘I’ll never use a dirty needle.’ Before long they’ll use a rusty nail to get high.”

The thaw was not only about recovery. Too often there was bad news. Shawn T. “Rooster” Austin, a twenty-four-year-old who’d grown up in Old Colony, was found dead one morning in a rooming house from a suspected drug overdose. The empty bag of heroin and a syringe without a needle were discovered near the corpse. “I can remember him as a little boy on his bike,” said a tenant at Old Colony, adding that she’d seen Rooster just a few weeks earlier. “He was saying that all his friends were dying, that all he was doing was going to wakes. Now, to think. . . .” Patricia Murray, a twenty-nine-year-old Southie woman, was a high school dropout and a hard-core heroin addict when she was picked up on prostitution charges in the late 1980s. “Do you think I like going out on the street?” she said at the time, her thin legs covered in a maze of sores. “Well, I don’t.”

But in the 1990s, for the first time, people were fighting back. Michael McDonald, who also grew up in the Old Colony project and would later write a bestselling memoir about life in Southie, founded the South Boston Vigil Group. Drugs had ripped apart his family, and two brothers died playing with the fire that Whitey stoked. “There’s a lot of pain in this neighborhood that’s been ignored by us,” he once said. “If you look at this community the way you look at an addict, we’re at the stage where the addict admits he has a problem.”

Former addicts like Leo Rull emerged as frontline troopers in Southie’s new war on drugs. Back when he was eighteen in the mid-1980s he was heavy into angel dust and coke, and a decade later he described himself as “a man on a mission,” trying to save the lives of a new generation of project kids, at times rushing those who’d overdosed in alleyways to emergency rooms and then counseling them afterward. Rull worked for an agency with a federal grant that was trying to break the cycle of poverty and drugs in the poorest sections of Southie and Roxbury, an ironic pairing given their past animosity. During busing, one of the Southie chants had been that Roxbury was plagued with troubles not found in the neighborhood whose twenty-nine thousand residents—and especially its pols—saw it as the best and most blessed place to live.

Later in the 1990s the city of Boston was planning to open the state’s first detox and treatment center geared exclusively for adolescent drug users. Inside the former rectory at St. Monica’s Church at the rotary near Whitey Bulger’s liquor mart, Catholic Charities had opened Home for Awhile, a halfway house with a dozen beds for boys aged fourteen to eighteen sent on referrals from the South Boston courthouse or detox centers.

Even if some believed that blacks and busing were the twin forces killing the neighborhood, that wasn’t the whole of it—one of their own was at it too. Southie had suffered in Whitey’s hands. This was the reality that Bergeron knew, that DEA agents knew, that state troopers knew, that drug dealers all around knew. If you wanted to supply Southie, one dealer later told an undercover DEA agent, “you either pay Whitey Bulger or you don’t deal or you end up dead.”

But back in the 1980s these were truths the old neighborhood was reluctant to confront. Instead, everyday people clung to the notion that Whitey was their protector. More powerful than any politician, he could police and preserve. To think this way gave them a lift; the ache for a protector had never been greater than after busing, when much of Boston and even the nation unfairly looked down on Southie as a racist, backwater town. Whitey might rarely be seen, but his presence was palpable and, for many, a source of comfort. He might even send flowers or contribute to the funeral expenses of a family who’d lost a member to drugs or violence. He had the right touch that way—sticking to the shadows. His hands were clean. Drugs and prostitution might be “a way of life in other sections of the city, but they will not be tolerated in South Boston,” the South Boston Information Center boldly declared in one of its newsletters, even as crime statistics showed that the neighborhood was just like any other in the city—awash in drugs. Yearly drug arrests were tripling in Southie between 1980 and 1990. Narcotics cases doubled in South Boston District Court from 1985 to 1990, and one Boston Police detective said he thought there was more coke in Southie per capita than anywhere else in Boston. In the end the neighborhood’s personality—its reserve and deep mistrust of outsiders—simply served Whitey all the more.

But just as the neighborhood was in denial, the FBI in Boston did not want to know the true story about drugs and Bulger and the forgotten casualties like Patricia Murray. Circulating instead on the streets of Southie and in the corridors of the FBI was a warm, do-good version of Whitey: Whitey hated drugs, hated drug dealers, and did his best to make Southie a drug-free zone.

It was a classic collision of reality and myth.

▪   ▪   ▪

The antidrug Whitey Bulger was always one of the most stubborn and durable stories about the crime boss. It was a position that Bulger, along with John Connolly, staked out by using a linguistic sleight of hand. To the self-styled moral gangster, drug money was separate from the drugs themselves. He could extort “rent” from dealers, loan them money to get them started, and demand that they buy from wholesalers with whom he and Flemmi were associated. He’d make the world safe for drug dealers in return for a piece of the action, but he didn’t personally cut the coke or bag the marijuana. That distinction became the basis for the Bulger ballyhoo: Bulger didn’t do drugs.

It was a tortured kind of semantic somersault, but there was precedent: Bulger’s attitude about alcohol. Bulger drank only occasionally, and when he did, just a glass or two of wine. He hated to see other people drink. Even on St. Patrick’s Day he would complain about celebrants drinking at midday. He once said “he didn’t trust anyone who drank.” Drinkers, he said, “were weak” and might rat him out.

During their two decades together the only time Bulger hit Teresa Stanley was after she stayed out late drinking wine at a friend’s house. If she sipped two drinks, he’d act as if she’d guzzled a dozen. “I almost got killed for drinking a couple glasses of wine,” Stanley recalled. Yet at the same time he was berating his girlfriend for wine tasting, Bulger was emerging as the neighborhood’s biggest liquor supplier. He happily emptied the register at the liquor store he’d taken over from Stephen and Julie Rakes and once bragged to a patrolling Boston cop, “We have the busiest liquor store around.” There were those who weren’t fooled by the hypocrisy. The increasing numbers of dopers and junkies joked about the poster hanging in one of the stores Bulger controlled: “Say Nope to Dope.” The liquor mart Bulger had taken over was nicknamed the “Irish Mafia store.”

Eventually Flemmi himself was caught red-handed trying to push the phony wordplay. He claimed under oath that he could not be prosecuted for the illegal gambling operation he and Bulger ran during the 1980s because the FBI knew about it and had even “authorized” it. As part of the claim, Flemmi described the gambling operation: he and Bulger mostly required bookmakers to pay them “rent” for protection. “So part of the gambling business was shaking down bookmakers?” a prosecutor asked Flemmi. Flemmi replied, “That’s correct.”

Then the prosecutor pounced: “If you were shaking down drug dealers, you’d be in the drug business, right?”

“I assert the Fifth on that,” Flemmi responded.

Flemmi was stuck. Faced suddenly with extending the same logic to drugs, Flemmi blinked. If he hadn’t, he would have undercut the comfortable fiction that had served him and Bulger for years—the claim they were not involved in drugs.

Under the FBI’s informant guidelines Bulger’s drug activities should have led to an abrupt end to the deal he and Connolly and Morris had worked so hard to preserve. Instead, the developing underworld intelligence putting Bulger together with drugs had to be discounted and deflected, and what better way to accomplish that than by cultivating a definition of drug activity that separated the money from the merchandise? Then Bulger, Flemmi, and Connolly could share a refrain: shaking down drug dealers did not make Bulger the person he in fact was—a drug lord.

▪   ▪   ▪

Right from the start Bulger and Connolly had begun drawing a portrait of Bulger as the antidrug gangster. During the crucial powwow on November 25, 1980, when Larry Sarhatt was conducting his suitability review of Bulger, the gangster proclaimed that he was “not in the drug business and personally hates anyone who [is]; therefore he and any of his associates do not deal in drugs.” Inside the bureau Bulger’s words went untested: if Bulger said so, it must be true. And in January 1981, as other police agencies were documenting Bulger’s alliance with the drug trafficker Frank Lepere, John Connolly was padding the FBI files with the opposite. Connolly reported that Bulger and Flemmi were actually distancing themselves from Lepere because of the latter’s drug predilection. Bulger, wrote Connolly, had formerly associated with Lepere but more recently had “broomed him due to his involvement in the marijuana business.”

It was a Teflon coating that came in handy in 1984.

The FBI was not a major participant as the DEA and the Quincy Police put together Operation Beans. But as a matter of courtesy, the DEA notified the Boston FBI of its intentions. The Boston office now faced a dilemma: what to do with Bulger and Flemmi? To decide, FBI managers in Boston naturally turned to the agents in the best position to gauge what Bulger and Flemmi were up to: John Connolly and Jim Ring, who’d taken over from John Morris as supervisor of the Organized Crime Squad. The fortyish Ring had been fighting the Mafia in New England for nearly a decade, but mostly from Worcester, a city in central Massachusetts viewed by agents as a minor league outpost. From the moment he took over the squad, Ring recalled, Connolly insisted that Bulger and Flemmi “weren’t involved in drugs, they didn’t do drugs, and they hated drug dealers, and that they would never allow drugs in South Boston.” When managers began raising questions, Connolly, fixed in place as the bureau’s authority on all things Bulger, came armed with his FBI files discounting any possible link between the gangster and drugs.

Having to notify FBI headquarters in Washington, DC, about the DEA’s plans, the Boston office fired off a two-page telex to headquarters on April 12, 1984, explaining that the DEA was targeting Bulger and Flemmi, “whom DEA alleges are individuals who control a narcotics trafficking group.” But the FBI in Boston urged calm. It labeled the DEA’s allegations “unsubstantiated, and DEA has furnished no specific information relative to their involvement.” Bulger, the telex concluded, should not be “closed due to the past, present and future valuable assistance.”

Ring authored a more detailed memo later in the year explaining the Boston office’s hands-off position toward Operation Beans, and once again the FBI in Boston displayed its backing for the antidrug version of Bulger. “The predication” for the DEA’s investigation, wrote Ring in October, “although it may be correct, is not consistent with our intelligence regarding the activities of these individuals.” Guided mainly by Connolly but also by Ring, the FBI brass in Boston would simply not accept the drug talk building around Bulger.

But behind Ring’s back even Connolly was apparently engaged in hushed FBI talk about Bulger and drugs. In early April 1983 fifteen tons of marijuana were seized from a warehouse at 345 D Street in South Boston. The marijuana belonged to a trafficker named Joe Murray, and after the raid Connolly and agent Rod Kennedy got to talking. Connolly described specifically for his colleague how Bulger profited from Murray’s drug business, Kennedy said later.

“The conversation was basically that Joe Murray was required to pay rent to Mr. Bulger and Mr. Flemmi for having used South Boston as a storage warehouse for his drug activity,” Kennedy recalled. He said Connolly told him that Murray had paid Bulger and Flemmi between $60,000 and $90,000 for that particular load. “It was like rent money for having used, you know, having gone into South Boston and using that area for illegal drug activity,” said Kennedy, adding that this amount was on top of more regular tribute.

But that was off the record. In a report he filed after the bust Connolly did not write a word about the payments Murray was making to Bulger and Flemmi. Instead, Connolly stated that the “Murray crew” was worried about Bulger being “upset with them over their storing grass in his town.”

Kennedy, who worked briefly as the bureau’s liaison with the DEA for Operation Beans, did share some of his intelligence about Bulger’s drug activities with DEA agents Reilly and Boeri. (Kennedy had an informant who’d told him Bulger relied on a South Boston drug dealer named Hobart Willis to serve as his go-between with Joe Murray.) But Kennedy never told anything to FBI supervisor Ring. Nor did Kennedy tell Ring or the DEA agents about Connolly’s disclosure regarding Joe Murray and Bulger. That was Connolly’s responsibility, not his, Kennedy felt. Besides, Connolly had probably expected him “not to pass it on,” and he didn’t want to cross Connolly.

Eventually more FBI agents in Boston would have informants telling the bureau about Bulger and drugs. By the mid-1990s even some of Bulger’s own rank-and-file dealers—like Polecat Moore—had decided to testify against him. And other dealers too. David Lindholm told investigators that in 1983 he was summoned to East Boston, where Bulger and Flemmi held a gun to his head to persuade him to pay them their share of his illegal drug action. In 1998 federal judge Mark Wolf ruled that Flemmi lied to FBI supervisor Jim Ring in 1984 in denying his and Bulger’s drug involvement. “It’s my understanding that he [Flemmi] was at least involved . . . in extorting money from drug dealers,” Wolf said on September 2, 1998.

But Connolly never let up. He had played a key part in creating the myth, and he clung to it. “Well, you know, I’ve never seen any evidence that they ever did get into drugs,” he boasted in 1998—six weeks after Judge Wolf’s comments in court. Never mind the evidence, the testimony, the federal judge’s findings. “I mean, to get involved with a drug dealer, to collect rent from them—they are the lowest form of animal life. A guy like Flemmi or Bulger is not ever going to put himself in a position to be dealing with these guys.”

Denial is not a river in Boston.

▪   ▪   ▪

Bergeron soon developed another reason for wanting to take Bulger and Flemmi down. He believed he’d lost a promising informant to them. It began one Sunday night in early October 1984 when the detective got word he better hurry down to the station. He arrived and learned that some other cops on the Quincy force had brought in thirty-two-year-old John McIntyre, an Army vet with a string of minor run-ins with the law, for questioning after he was found trying to break into his estranged wife’s home. Held in one of the claustrophobic, poorly lit cells, McIntyre’s talk soon went way over the heads of the patrol officers. The man was rambling on about marijuana, mother ships, gunrunning, and, most shocking, the Valhalla.

The fishing trawler Valhalla had left Gloucester, Massachusetts, on September 14 for a few weeks of swordfishing. At least that was the cover story. In fact the trawler was carrying seven tons of weapons valued at a cool million—163 firearms and seventy rounds of ammunition—destined for the IRA in Northern Ireland. Two hundred miles off the coast of Ireland the Valhalla met up with a fishing boat from Ireland, the Marita Ann. The cache of weapons was transferred, and the operation seemed a success. But the Irish Navy had been tipped off and intercepted the Marita Ann at sea. The seizure of an IRA-bound arsenal made front-page news on both sides of the Atlantic.

Bergeron summoned Boeri, and they sat with McIntyre in the office of the chief of detectives at the Quincy Police station, a tape recorder running. Bergeron sat transfixed as the names of some of the men he’d been targeting came tumbling off McIntyre’s lips: Joe Murray, the major drug smuggler who worked out of Charlestown, and Patrick Nee of Southie, who worked as a liaison between Bulger and Murray. Identifying himself as a member of Murray’s “cell,” McIntyre described a number of marijuana-smuggling operations. He talked about how in the past couple of years Murray’s group had merged with the “South Boston organization,” and that meant Nee was around more often because “they wanted to bring some of their own representative people over, so they could keep an eye on everything.”

With regard to the botched IRA gunrunning mission that was so recently in the news, McIntyre confessed that he’d actually helped load the weapons and then served as the boat’s engineer, and he said that six men went along on the voyage—himself, a captain, an IRA member named Sean, and three guys from the Southie crew. He didn’t know them except by nicknames, and he didn’t like them. “You can tell them right away. All of them wear scally caps. They got the Adidas jumpsuits, and they ain’t got a speck of dirt on them. They don’t know the first thing about a boat. Every day they got to take two, three showers. These fuckin’ guys, running around flossing their teeth, takin’ showers. There was a storm so bad out there that me and the captain were driving about two days, three days. They wouldn’t even come out of their cabins.”

Murray, Nee, and “the guys from the liquor store” were behind the arms shipment, and, McIntyre added, theirs was a gang no one should take lightly. “They would tie you right up with piano wire to a pile and leave you there. That’s their idea of a joke.”

The night the Valhalla left port, Kevin Weeks had stood watch on a nearby hill. Kevin was tough, said McIntyre, but then there was “one guy above him.” Cross him, said McIntyre, and “he’ll just put a bullet in your head.” Bergeron could see McIntyre was shaky, almost petrified. “I’d like to start living a normal life,” he’d said earlier. “It’s almost like living with a knife in you. The last few years you don’t know where you’re going to end up or what kind of demise you’re going to come to. I mean, I didn’t start out in life to end up like this.”

He never actually uttered the name of the “one guy” above Weeks who oversaw the drug smuggling and the Valhalla, but everyone else in the room knew exactly whom he meant: Bulger.

Bulger was considered to be a chest-beating IRA sympathizer. But eventually some investigators came to believe that Bulger, just as he’d betrayed his neighborhood with his phony antidrug posturing, had also betrayed the IRA. He might have played a key role in rounding up the weapons to sell to the IRA, but after taking payment he dropped a dime. “Whitey waved good-bye to the Valhalla, then made a phone call,” said one official later. Even if true, Bulger was not the only leak. The former head of the IRA in Kerry later admitted that he’d compromised the gun exchange at sea. Sean O’Callaghan, an assassin-turned-informer, said he did so to get revenge against the IRA. He immediately became a marked man for admitting his perfidy.

Bergeron at the time knew none of this. He was soaking up McIntyre’s words and feeling as if he’d won the lottery. “Seemed like an awful big gift at that particular point in time,” he was thinking. “This guy had a mountain of information.” Over the next several days he and Boeri notified the DEA, customs, and even the FBI. McIntyre was willing to cooperate, and plans were made to use him to gather more information about the gang’s drug trafficking. Then one day a few weeks after this seemingly huge break, McIntyre left his parents’ house in Quincy, saying he was heading off to see Patrick Nee. McIntyre was never seen again. His truck and wallet were found abandoned in a parking lot. Bergeron was crushed. It was Halloran all over again. It was Bucky Barrett all over again. Disappearances that followed talk about Bulger and Flemmi. There was even one more disappearance that autumn that fell outside Bergeron’s jurisdiction. Stevie Flemmi and Deborah Hussey were having a bad time of it. The couple was fighting a lot, and Hussey was threatening to tell her mother about her affair with Flemmi. Of course, this would have made things difficult for Stevie. Suddenly Deborah Hussey disappeared. Like Debra Davis before her, she was twenty-six. Flemmi went home to Marion Hussey in Milton. He wasn’t about to tell Marion he’d just buried Deborah in a basement in South Boston, a location he and Bulger had already used to dispose of John McIntyre’s body a few weeks earlier and, before that, Bucky Barrett’s. Instead he just shrugged his shoulders and did his best to console the girl’s mother.

▪   ▪   ▪

Bergeron believed Bulger and Flemmi had murdered McIntyre. He didn’t know exactly how they’d found out about his cooperation, but he suspected the FBI. Bergeron and, especially, DEA Agents Reilly and Boeri already knew about the rumors circulating throughout law enforcement in the Boston area that Bulger and Flemmi were informants for the FBI. In planning for Operation Beans, they had consulted with trooper Rick Fraelick, who provided the new team of investigators with photographs of the targets, informant reports, and other intelligence that state troopers had assembled. He also gave them a full accounting of the failed bid at electronic surveillance at the Lancaster Street garage in Boston. Fraelick was convinced the FBI had “dimed them out.”

The new investigators were not naive. They harbored suspicions about Bulger’s possible ties to the FBI. But no one had hard proof. From their own informants they also knew that Bulger was supremely confident, that he liked to boast about outfoxing anyone who might try to pursue him. Bulger would rank on the state troopers, calling the failed Lancaster Street garage effort “a joke.” It was similar to the wiseguy bluster the troopers had witnessed from their perch in the rooming house, spying Bulger posing outside the garage, sucking in his stomach.

In fact Bulger had taken the Lancaster Street garage challenge to heart. Post-Lancaster, the ever-wary Bulger and Flemmi had grown increasingly careful in their ways. Bulger installed a sophisticated alarm system in the condo he shared with Greig. He did the same with the 1984 Black Chevy Caprice he and Flemmi drove. (The car was registered to Kevin Weeks’s sister Patricia, who worked as a clerk for the Boston Police.) In the condo Bulger now always had the TV and stereo turned up. In the car he always blared the radio and a police scanner crackling with noise to mask his low talk. Then at the end of his day Bulger parked the car right up against the condo’s door, where he could watch it.

Moreover, Bulger and Flemmi had further insulated themselves, especially Bulger. Instead of exposing himself to a steady stream of underworld figures—as he had each day at the Lancaster Street garage—Bulger pulled back. Bulger, one informant told investigators in 1984, “will converse with subordinates only when necessary. Subordinates cannot directly contact Bulger and Flemmi. Contact is directed to George Kaufman, and Kaufman will relay information.”

The extra Bulger caution was in addition to his already well-established countersurveillance habits, such as the driving techniques he employed to check to see if anyone was following him: suddenly pulling over; suddenly reversing direction, especially on a one-way street; suddenly veering from the high-speed lane on the highway to take an exit. Bergeron and DEA agents Reilly and Boeri took note that Bulger and Flemmi seemed to function on high alert at all times.

Bulger and Flemmi and the new investigators periodically bumped into one another. Bergeron and Boeri were tailing Bulger one summer night along Dorchester Avenue in Southie when Bulger spotted them. Bulger waved and smiled. But Whitey wasn’t always so jaunty. Bergeron and another detective one night set up surveillance at the condo in Quincy with a white Ford van the DEA had provided. It was 2:02 in the morning, and Bulger came out of unit 101, got into his car, and drove around the parking lot while staring suspiciously at the van. Then he parked, got out, and looked into the van’s rear window. He walked all around the van, checking out the front plate. Visibly agitated, he went back inside the condo. Investigators hustled over to drive the van away, and as they did, Bulger appeared in the rearview mirror in a car that pulled out of the shadows by the dumpster.

The investigators realized from these cat-and-mouse encounters that Bulger and Flemmi were aware of their interest in them. But even while recognizing that Operation Beans was unfolding in a high-risk atmosphere, they never thought of not going for it. Bergeron, Boeri, and Reilly had frequently worked over the possibility that Bulger and Flemmi were FBI informants. But in the end, so what? The bottom line in 1984 was actually quite simple. Bulger and Flemmi, Reilly concluded, “were the strongest organized crime figures remaining in Boston, since the recent downfall of the Angiulo organization.” Even if they were informants, noted Reilly, “informants aren’t given any particular free pass.” They all recognized that building a case would be a lot easier if they could line up witnesses to testify in court against Bulger and Flemmi, but that wasn’t realistic—not with Bulger’s insular lifestyle, not with the widespread fear of Bulger that persisted in the underworld, not when men like John McIntyre disappeared off the face of the earth. Thus, the central game plan for Operation Beans was to capture Bulger’s own words. For much of 1984 the investigators worked to assemble the probable cause they’d need to win a judge’s okay to install bugs.

Even though the FBI was notified as a matter of courtesy in April 1984, the goal in putting together Operation Beans was to limit the FBI’s knowledge and participation in the drug investigation. “I wanted to keep it away from the FBI and go on with it,” said Reilly. The case, he said, was, “DEA initiated, DEA sustained, DEA funded. We did everything.” The whole operation was specifically set up to try to keep certain Boston FBI agents from knowing about it. That autumn, when agents from the FBI’s crack “tech team” arrived from New York City to consult with the DEA on installing a bug in Bulger’s car and condo, the out-of-town FBI agents were ordered not to check in with the Boston FBI office. The two local FBI agents who were eventually loaned to the DEA to help monitor the bugs were newcomers to the city. The office for Operation Beans was even moved off site to the Fargo Building in downtown Boston, away from the John F. Kennedy Federal Building, where DEA agents and FBI agents often passed each other, ate lunch together, and might gossip about cases.

▪   ▪   ▪

But the FBI did know, and the way Flemmi saw it, the FBI’s role in Operation Beans was “no more than a surreptitious effort to ensure that the investigation was ultimately unsuccessful.” Connolly, it turned out, had caught wind of Operation Beans right from the start—early on in 1984, even before the investigation had a name and before the DEA had assembled its plan of action. Immediately after the telex was sent from Boston notifying FBI headquarters about DEA’s planned investigation, a top FBI official in Washington, DC, named Sean McWeeney picked up the telephone to call Jim Ring. McWeeney was chief of the Organized Crime Section at FBI headquarters.

Instead of Ring, John Connolly took the call.

“Aren’t these our guys?” McWeeney asked the handler.

And if Connolly knew, Bulger and Flemmi knew. They continued to meet regularly throughout the year, and, said Flemmi, the talk often turned to the intensifying interest the DEA and Quincy Police showed in them. They had a kind of cross-fertilization going, each sharing with the other whatever information they’d picked up. Connolly got additional information from other agents, either directly or through Ring. It would have been helpful to have John Morris’s input as well, but not only was Morris no longer running the squad, but he was also out of town: the former supervisor had been dispatched to Florida on a special assignment and would not return until early 1985.

During one key session in September 1984 Bulger, Flemmi, Ring, and Connolly huddled at Connolly’s apartment in South Boston. Connolly’s apartment had been chosen because of all the cops spotted skulking around Bulger’s condo all hours of the night. The foursome, recalled Flemmi, had an “animated discussion” about Operation Beans. Flemmi and Bulger made their self-serving denials to Ring about the drugs. Ring and Connolly told them not to worry, insisting that he and Bulger “hang in there and stay, you know, stay on the team.” In addition, Bulger and Flemmi were told that Operation Beans was working out of the Fargo Building in Boston. This enabled Bulger to stake out the building and pick up the makes, models, and plates of the undercover cars the investigators were driving.

By the time DEA investigators, on Christmas Eve, won a court order to place a wiretap on George Kaufman’s telephone, Flemmi and Bulger were one step ahead. John Connolly had provided a holiday treat: a warning about the telephone wiretap. Thus, instead of capturing criminal conversations, all DEA Agents Reilly and Boeri overheard was Flemmi talking nonsense or in code to George Kaufman. The agents never picked up Bulger using the phone at all.

Given the heads-up, it was a wonder that Bergeron and the DEA’s Reilly and Boeri actually succeeded in planting microphones in Bulger’s car and condo. But they did do it, briefly, for a few weeks in 1985. The DEA agents and Bergeron had been left to their own devices after the FBI technical team called in for a consultation was unable to offer any surefire method to implant a microphone in Bulger’s car and condo. Both contained sophisticated alarm systems designed to detect any intrusion inside the condo or the car. The technical team, looking at the condo and the car from a distance, concluded that unless the local agents could come up with the codes to defeat the alarms, there was no way agents could sneak inside to install the bugs. The other option the FBI mentioned was replacing Bulger’s car with an exact duplicate wired for sound. Reilly considered that proposal ridiculous. After a day the FBI tech team returned to New York. Their anemic proposals simply fueled Reilly’s worries about the FBI, even if the tech team had been ordered not to tell local FBI agents about being in town. “I thought they didn’t put their best effort forward.”

So Reilly, Boeri, and Bergeron took matters into their own hands. They obtained a Chevy exactly like Bulger’s and began studying it, looking for a way to insert a bug without having to break into the car. They found a point of entry low on one of the door panels, and they practiced drilling into it until they could install a microphone that worked. They took the same approach with the condo—they practiced drilling into window sills to plant a bug from the outside.

In early 1985, under the cover of darkness, the agents got a bug inserted into the condo’s window. “The bug worked fine,” Bergeron said. The problem, he said, was that Bulger blasted the stereo and television once Flemmi arrived, and the two gangsters would go upstairs to talk business. The attempt was a bust.

Then, on February 2, 1985, while Bulger slept, the agents installed a bug in the door panel of the black Chevy. But the next day, after Bulger got into his car and drove into South Boston, all the agents got was an earful of road noise. The microphone was picking up the bump and grind of the car’s wheels turning along the highway. Even after repositioning the bug the next night, the agents were faced with a persistent “lack of clarity” in catching Bulger talk. Part of the problem was that the technology they’d been forced to use had severe limitations. They were using a tiny device that transmitted a signal to a surveillance vehicle, where the actual recordings of the conversations were made. This meant that their ability to tape anything depended on keeping the van close to Bulger’s car—no easy task. Moreover, the agents were always competing with the road noise and Bulger’s habit of playing the car radio as he and Flemmi chatted quietly, managing their affairs in a general state of wariness.

It was a constant struggle to decipher who exactly was talking in the car and what they were saying. The best night came on February 17, 1985, with the two DEA agents and Bergeron tailing Bulger and Flemmi to a meeting with George Kaufman at Triple O’s. It was after 10:00 p.m. when Bulger and Flemmi emerged from the bar and drove off. Fighting through the radio and road noise, the agents then heard Bulger and Flemmi talking about the revised underworld order. They heard the gangsters talking about Howie Winter, who was due to come out of prison soon. “Fuck Howie,” Bulger said.

The agents heard the talk veer briefly toward drugs.

“This fuckin’ coke deal,” said Flemmi.

“I’m running the business and everything over the phone,” replied Bulger.

It was tantalizing stuff, but never more than a tease. They got snatches of talk about money, about “drug outlets,” and about Bulger’s gambling operations. They even captured what they thought was a reference to one of the local FBI agents, but they didn’t know what it meant: “Connolly has been a little fuckin’ nervous,” Flemmi remarked at one point.

The agents kept at it nonetheless, but as the nights passed they were never able to get enough words strung together to put together a criminal storyline. They saw Bulger sitting in the car with Patrick Nee, who worked as messenger between Bulger and Joe Murray, but they couldn’t quite capture what was said. They watched a Bulger subordinate climb into the car and deliver a pile of money to the crime boss, but once again their talk was broken up. They listened to an angry Bulger curse another underling for daring to come for him at Teresa Stanley’s. Bulger read the miscreant the riot act, saying he would “clip” anyone who came there. Family had nothing to do with business, he said.

No investigation had ever caught Bulger on tape before, even in fractured form, but the investigators realized that if they wanted to make a case that they could take into court, they were going to have to improve the quality of their recordings. On the morning of March 7, at 2:40 a.m., Reilly and Bergeron made a final attempt to tinker with the position of the microphone. “We thought he was asleep because normally he would be asleep around two-thirty in the morning,” recalled Reilly. “We came around the building, and he came out of the condo. He saw us, and we saw him, and we took off and ran.” Bergeron said an agitated Bulger jumped into his car with his girlfriend Greig and began driving in circles around the parking lot. “He began driving around like a madman, screaming at Greig, real hyper and suspicious and screaming he knows all about the cops.”

Flemmi was out of town, in Mexico, and a jumpy Bulger hunkered down. Eluding the investigators, he met with John Connolly the very next day, on March 8. Then, three days later DEA agents Reilly and Boeri followed Bulger as he drove his black Chevy into a garage beside the liquor mart in Southie.

The next words they heard from Bulger signaled the end.

“He’s right—they did put a bug in the car.”

The agents jumped out of their van and raced in to retrieve their electronic surveillance equipment. The last thing agents ever wanted was for targets to know exactly what kind of technology was being used against them. They found Bulger tearing open the door panel and Kevin Weeks standing nearby holding a radio frequency detector that located bugs just like the bug the DEA had used. Facing down Reilly, Boeri, and two other DEA agents inside the garage, Bulger resumed the take-charge bounce that usually characterized his interplay with cops. He said he was surprised they’d been able to install a bug. “I got a pretty good alarm system,” he said as Reilly stepped forward and fumbled around the door panel to pull out the microphone. Bulger mentioned he knew something was up after bumping into Bergeron and Reilly in the condo’s parking lot a few nights earlier. He did not, however, mention his FBI contacts.

Boeri noticed that Bulger wore a fancy belt buckle—inscribed with the words “ALCATRAZ: 1934–1963.” Making small talk, the agent pointed out the handsome buckle, but Bulger didn’t dare mention how he’d come to possess it.

The crime boss and the agents kept up their banter, with Bulger nagging them for details about when the bug was installed and how long it had been running. He guessed “seven or nine days.” Weeks offered his guess the bug had been in place for about two months. They probably had a bug in his car too, Weeks added.

“You want to buy my car—cheap?” Weeks wisecracked.

Boeri asked Bulger where Flemmi was.

“He’s around,” Bulger lied.

The talk went around in circles. “Hey,” announced Bulger at one point to the DEA agents, “we’re all good guys.”

How so?

“You’re the good good guys. We’re the bad good guys.”

The agents took their equipment and went home. Two days later Boeri and Bergeron were driving past Teresa’s house when Bulger waved them down. He kept up his gangster panache, advising the investigators they shouldn’t believe all the things they heard about him. He showed them that the car panel had come loose and asked for their help securing it.

“Pretty ingenious installation,” Bulger told Boeri, returning again to the bug, fishing for information.

Flemmi returned from Mexico and ran into Boeri and Reilly in the parking lot of the Marconi Club in Roxbury, where he often hung out. They talked about the “excitement” earlier at the garage over the bug. Flemmi asked about the quality of the transmissions. “Doesn’t the cold weather affect the batteries?” he taunted. The agents said everything worked fine. They weren’t going to give an inch.

Flemmi urged that they all get along. Instead of chasing each other, they should be scratching each other’s backs. “Whaddya want?” he joked. “We don’t need Miranda. We can wrap a rope around anyone’s neck. Just tell us what you want.” Then he asked where all this was headed. He hoped the agents were not going to bother them much longer. “You’re not going to make Jimmy and me a lifetime investigation?”

“Well, we’re really just getting started,” said Boeri.

Bulger and Flemmi knew this was a bluff. The two gangsters had already huddled again with Connolly. “John Connolly said that Jim Ring told him that the DEA investigation was collapsing, or it collapsed, words to that effect,” Flemmi said. “Connolly told me. We had frequent meetings at John Connolly’s house, independent of the meetings we had with supervisors.”

In the garage the moment Bulger had uttered the line, “He’s right—there is a bug in the car,” DEA agent Reilly was convinced that the FBI had tipped off Bulger. Reilly had his suspicions but couldn’t prove exactly who in the FBI Bulger was referring to. But the words were like the exclamation point to long-harbored concerns about Bulger’s ties to the FBI. From then on, Reilly, Boeri, and Bergeron all believed their effort was compromised.

Even so, no governmental inquiry was ever undertaken to examine this belief. No postmortem was conducted to try to find out exactly why Operation Beans failed. Everyone walked away, moved on. It was as if yet another investigatory dud gave rise to a numbness, with police agencies now unwittingly ready to accept the FBI’s protective shield of Bulger and Flemmi as a fact of life, the way things were in Boston, part of the city’s fabric.

Outwardly, the gangsters made the best of it. “I didn’t think they appeared to be concerned,” Ring recalled. Bulger and Flemmi acted like the car bug was a pretty funny joke. “It was more a matter of, I guess I’d have to call it ‘Gotcha.’”

The truth was that the close call was no laughing matter. The year-long chase had proved grueling. Bulger and Flemmi had felt harassed at every turn. Despite the FBI, the DEA had actually managed to accomplish a first—a bug on Bulger. Detective Bergeron and DEA agents Reilly and Boeri had revealed the man behind the myth, though not in a way that could result in a criminal indictment. But what Bergeron and the agents knew would remain locked in confidential law enforcement files. John Connolly, Bulger, and Flemmi resumed their antidrug mantra. They had beaten the DEA’s Operation Beans.

But it had been way too close for comfort. The scrutiny was tiring—not the good life the gangsters had in mind as part of their deal with the Boston FBI. So in April 1985, just days after Flemmi’s repartee with the DEA agents at the Marconi Club, Bulger and Flemmi were looking for reassurance that things were okay and would stay that way. John Morris was back in town, and it was time to pay him a visit.