Gang of Two? - 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



Gang of Two?

Like a curtain rising, the garage doors at the Lancaster Foreign Car Service flew open in the spring of 1980 on a new era in Boston’s underworld order. Howie Winter had fallen, and a realignment was under way. It was an industry shakeout, and standing in the bays of the repair shop were Whitey Bulger and Stevie Flemmi, arms folded, ready to take center stage and exploit any and all opportunities.

The old haunt, Marshall Motors in Somerville, had been abandoned in favor of this new downtown location. Though some of the former Winter Hill gangsters were on the run, others had come along. George Kaufman, who had operated Marshall Motors as a front for Howie Winter, now operated the Lancaster Street garage for Bulger and Flemmi. In the mornings the bays might be filled with the clanging and banging of mechanics’ tools, but by early afternoon the tone of the place would change markedly. Most days Bulger and Flemmi arrived around one-thirty to take over the show. Whitey pulled into an empty bay and climbed out of his shiny black 1979 Chevy Caprice. The hushed conversations, the stream of visitors—it all revolved around Bulger and Flemmi. And accompanying them was the big and beefy Nick Femia, an enforcer with a reputation as a killer hooked on shotguns and cocaine. Femia, Kaufman, and other wiseguys stood outside as lookouts as Bulger and Flemmi took up in an office inside.

The Lancaster Street site represented an upgrade, the mobster equivalent of a law firm or bank moving its base from the margins to the center of a city’s business district. It was a location that came with certain frills that just about any Bostonian would covet: a couple blocks west and across the street stood Boston Garden. The Celtics, led by a rookie named Larry Bird, had just fallen short in their surprising run at the Eastern Conference title against Philadelphia.

More important, the Lancaster Street garage was situated in close proximity to the city’s Mafia heartland in the North End. In a matter of minutes you could walk from the garage to the front door of 98 Prince Street, where Gennaro Angiulo and his four brothers oversaw the region’s LCN racketeering enterprise. Finally, there were Bulger’s neighbors a few blocks south: the Lancaster Street garage stood practically in the shadow of the FBI’s Boston field office in Government Center, where John Connolly and John Morris were stationed.

In many ways Bulger was on a roll. Even though their former Winter Hill gang had suffered a crippling blow from the government’s wildly successful prosecution in the race-fixing case, Bulger and Flemmi seemed to have adopted the optimistic view that in life there were no setbacks, only new opportunities. They’d heard that an unaffiliated East Boston wiseguy named Vito was running a loan-sharking and gambling business without the blessing of either Bulger or the Mafia. Soon the gun-toting Femia paid Vito a visit and put a pistol to his head. Then Bulger and Flemmi had their own session with Vito in the back room of a downtown smoke shop and explained the meaning of life. Vito decided to retire, and Bulger, Flemmi, and Femia took control of the East Boston franchise.

There was no question that when the need arose, Bulger and Flemmi were hands on. If a “client” was late on a loan payment, they would take the wayward one for a ride in the black Chevy. Flemmi would drive with the recalcitrant debtor seated by his side. From the backseat Bulger would whisper in a low but unmistakably firm tone about the need to “get it up” or “face the consequences.” If a second trip was necessary, Bulger and Flemmi would have someone like Femia trash the debtor’s apartment while the two crime bosses talked over the problem during the ride-along.

Usually there was no call for a third ride.

Inside the FBI Connolly and Morris were stuffing the bureau’s files with confidential reports about how down and out Bulger and Flemmi were in the wake of Howie Winter’s fall, but out on the street the two gangsters hardly appeared to be suffering. In addition to coordinating their affairs with the Mafia, the two were busy launching their new tactic of extorting tribute—or rent—from already established rackets. The bookmaker Chico Krantz was now stopping by to drop off his monthly payments, at one point plunking down an extra $5,000—an additional fee Bulger had demanded for settling a dispute Krantz had had with another bookie. Krantz was only one of many bookies now paying such tributes.

There was one hardship, a personal one: on New Year’s Day 1980 Bulger’s mother had died at Massachusetts General Hospital after a long illness. She was seventy-three. Whitey Bulger had stayed on in the family apartment on O’Callaghan Way in the South Boston housing project where he, his brother Billy, and John Connolly had all grown up. It was where Flemmi often picked him up in the late morning in the black Chevy to start their business day.

Bulger did have two other women in his life to comfort him. One was his longtime girlfriend, Teresa Stanley, who lived in South Boston. He’d met Stanley in the late 1960s, when she was twenty-five and aimless, already a single mother of four children. He taught her how to organize her life and to have dinner ready for him each night at the same time. She was always grateful for his presence in her life. He was strict with her children, and he wanted everyone to sit at the dinner table together. But these days, even if he played father to Teresa’s four kids, Bulger often ended his day in the arms of a much younger woman, a dental hygienist named Catherine Greig, who lived in North Quincy.

Despite the loss of their mother at the start of the year, 1980 was a time when both Bulgers were consolidating their power and fast approaching the top of their games. Elected as president of the State Senate in 1978, Billy Bulger had established himself as a charming orator and cunning powerbroker. Conservative on social issues—opposing abortion rights and supporting the death penalty—Bulger was an outspoken defender of the working class. He remained impatient with dissent, however, if not intolerant. In words that could have been ascribed to his gangster brother, politicians described having worked with “two Billy Bulgers.”

“If you are going to be just his friend, he’s very polite, very proper, a very nice person, a good host, all that,” George Keverian, the house speaker, said about dealings with his counterpart in the State Senate. But, he added, if you opposed Bulger, you faced a different and darker side: “He gets steely-eyed, he gets cold.”

In a number of highly publicized disputes Billy Bulger’s reputation as a vindictive autocrat was cemented. In one, Billy became enraged when a Boston housing court judge refused to fill a clerkship with his hand-picked choice. The judge lashed out against Bulger’s raw patronage move by calling Bulger a “corrupt midget.” Payback came through legislation that cut the judge’s pay, reduced the size of his staff, and ended the court’s independent status by having it folded into another branch of the judiciary. Both Bulgers were used to having the last word.

Indeed, the Bulger brothers—each in his own way—seemed determined to make a struggling city theirs. It was a period of economic unrest, of high inflation, with an aging ex-movie actor, Ronald Reagan, on his way to ousting the unpopular incumbent president, Jimmy Carter. It was the dawn of what would soon become known as the high-flying 1980s, the “Me Decade,” featuring yuppies, skinny ties, designer food, and leg warmers, an era of Wall Street greed and corporate takeovers led by mega-financiers like Carl Icahn and Michael Milken.

Strutting into the Lancaster Street garage each day were Bulger and Flemmi to take care of their own mergers and acquisitions. And Jane Fonda wasn’t the only one exercising hard. Both Whitey and Stevie worked out, lifted weights, and stayed fit. Bulger, even at fifty, took his appearance seriously, and he showed up at the garage to flex his underworld power wearing the body-fitting shirts that were in style. There wasn’t a mirror or a windshield he didn’t like. He’d pause, catch his reflection, secure in the feeling that no one—at least not the Boston FBI—was watching what he was really up to.

▪ ▪ ▪

But someone was watching.

Peering out from behind the shabby curtains of a second-story window in a flophouse directly across from the Lancaster Street garage was a group of hard-driving troopers from the Massachusetts State Police. Six days a week, beginning in late April and lasting into July, the troopers were hunkered down at the window in the roach-infested bedroom, chronicling the mob action across the street.

They saw the little things—Bulger and Flemmi preening on the sidewalk between appointments, sucking in their stomachs when a pretty woman walked by or making sure their shirt buttons lined up with their belt buckles. They watched Bulger’s body language downshift into business gear when he was displeased—charging hard at a visitor and jabbing a finger into the man’s chest, swearing at him all the while. When Bulger was done, Flemmi would take over and do the same. More significant, the troopers saw the big things—men arriving with briefcases and betting slips. They watched money change hands. They took notes—and pictures. In all, during the eleven weeks they watched they counted more than sixty noted underworld figures come and go; in fact, virtually every organized crime figure in New England, at one time or another, showed up at the Lancaster Street garage for a meeting with Whitey Bulger and Stevie Flemmi.

Like a silent movie—no words and all action—the garage provided a panoramic shot of the whole of the Boston underworld. And the action filling the wide screen in living color contrasted sharply with the narrow snapshot of Bulger and Flemmi that the Boston FBI was planting in the bureau’s files and in the minds of anyone who asked about the two gangsters.

The state police surveillance had begun quite by accident. Trooper Rick Fraelick happened upon the garage one day while he was driving in the neighborhood on a tip about a stolen car ring. He drove down Lancaster Street and noticed George Kaufman and some of the other mobsters standing on the sidewalk. He pulled over and, out of their view, checked out what was going on.

It was a jaw-dropping moment. He recognized other mobsters coming and going. He saw Bulger and Flemmi. Fraelick returned to headquarters and told Sergeant Bob Long, the supervisor of the Major Crime Unit. Long accompanied Fraelick on a few drive-bys to view the activity for himself. They felt the adrenaline rush that comes with the prospect of a potentially big case. The question was where to set up. Directly across from the garage was a run-down brick building, 119 Merrimac Street. The first floor was a gay bar. Upstairs rooms could be rented. It was a dump, a cheap place where winos crashed. There was little privacy: the uninsulated walls were made of thin wood paneling that a fist could pass through easily. Posing as a gay man, Fraelick rented the room looking directly on to the Lancaster Street garage, and starting in late April, he and Long and trooper Jack O’Malley began documenting Bulger’s affairs.

Other troopers were involved along the way, but these three were the principal investigators who arrived early each day and took up at the window, usually in shifts of two. The men were all local. Long, in his midthirties, had grown up just outside Boston, in nearby Newton, the fourth in a family of ten kids. His father was a lawyer, and since he was a boy he’d dreamed of becoming a state trooper. Long was a jock in high school, even won a partial basketball scholarship to a local junior college, but once he blew out his knee, his sporting life was over. Less than nine months after earning a college degree in criminal justice from City College in San Francisco in 1967, he was back in Massachusetts standing at attention at the state police academy.

Now in charge of a special investigations squad, Long had handpicked Fraelick and O’Malley—both, like himself, athletic and solidly built, the brown-haired Fraelick originally from the North Shore and the reddish-blond O’Malley from Boston’s Dorchester neighborhood and a family of cops. (O’Malley’s dad, a Boston cop, still patrolled Roxbury.) The two troopers, both in their late twenties, were pulled off the road to work with Long. The hours were a killer, but O’Malley was single and Fraelick, though newly married, didn’t have any kids yet. Long had two sons, and the youngest, ten-year-old Brian, had just been selected as the poster boy for the Massachusetts Cystic Fibrosis Foundation. The boy got to pose with Bobby Orr of the Bruins in the poster.

The room the troopers shared was small and stuffy, and as the weeks passed into June and July it got hotter. They’d come to work wearing shorts and T-shirts, carrying gym bags that concealed their cameras and logbooks. They practically had to whisper so the other occupants in the flophouse would not overhear them. Fights frequently broke out in the other rooms running down the hallway. But it was worth it, they thought.

The garage’s daily rhythm quickly revealed itself: Kaufman opened up in the morning, and then Bulger and Flemmi took over in the early afternoon. Besides Bulger, Flemmi, Kaufman, and Femia, there were a number of other regulars, including established mobsters like Phil Waggenheim and Mafia associate Nicky Giso.

Then there were the heavy hitters. Bulger met with Donato Angiulo, a capo de regime, or captain, in his brother’s crime family. Larry Zannino, Flemmi’s old acquaintance who ranked second only to underboss Gennaro Angiulo in the hierarchy of the Boston Mafia, made entrances that resembled a Hollywood set piece. Zannino would pull up in a new blue Lincoln Continental or a polished brown Cadillac driven by an underling. The men at the garage would scatter like ants as Zannino made his way from the car to a meeting inside the office with Bulger and Flemmi. Sometimes the flamboyant mafioso would embrace Bulger and kiss him on the cheek. Not every visit was so lovey-dovey, though. Once Zannino emerged from the office and was met by two men who’d been waiting outside. Zannino embraced one, but when the second man moved in for a hug, Zannino slapped him violently. The man dropped to his knees, and Zannino began yelling. Bulger and Flemmi hustled out of the office to catch the show. Zannino berated the fleeing man and then stopped, composed himself, and climbed back into his cool blue Continental.

To the troopers taking notes across the street, Bulger and Flemmi and the Mafia—it all seemed like one family. The troopers developed a feel for the garage. They could tell when an associate was “in the shits” with Bulger. Bulger would make these men wait, and the troopers watched the men nervously pacing outside the garage, checking their wristwatches for the time, looking up and down the street, their faces clenched. When Bulger finally appeared, he would begin the finger jabbing. The body language spoke volumes. Bulger was in charge, no doubt about it. The other men at the garage deferred to him, including Flemmi.

Over time the troopers could detect when Bulger was in a funk. He would turn dark, refuse to talk to anyone or to be bothered, and sulk over in one corner. In keeping with his fanaticism about fitness, he’d take a hamburger and throw out the bun, eating only the meat. Long, O’Malley, and Fraelick learned that Bulger was neat as a pin, a casual but careful dresser who wouldn’t let a hair fall out of place. He liked the things around him kept up and in place. One time Femia had gone down the street to the McDonald’s near Boston Garden. Upon his return the hungry henchman spread out the Big Mac and French fries on the hood of the black car. Bulger came out of the office, saw the greasy display of fast food, and turned white-hot. He marched over, grabbed the French fries, and began whipping them at Femia. He whipped French fries into Femia’s chest and face. The 240-pound Femia backpedaled and stumbled, a hulking hitman cowering before Bulger’s rage. It was as if, instead of hot French fries, Bulger were swinging a crowbar. The troopers would never forget the food fight and its clear message: you did not mess with Whitey Bulger.

At times Long, Fraelick, or O’Malley followed Bulger and Flemmi in order to pick up their routine. They learned that Flemmi often kept the Chevy overnight. They saw that Whitey was not the only one with a complicated love life; Flemmi was the true underworld Lothario. In fact, his juvenile rap sheet contained a portent of the man’s appetites: an early arrest at fifteen for a bizarre charge of “carnal abuse” without further explanation. Flemmi always had a slew of women. He might age, but he made sure the women on his arm were young.

Since the 1960s Flemmi had lived on and off with Marion Hussey in a house that once belonged to his parents just over the Boston city line in Milton. He kept Hussey as his common-law wife, as he’d never divorced Jeannette A. McLaughlin, the woman he’d married in the 1950s when he was a paratrooper. Then, in the mid-1970s Flemmi became smitten with a teenager working behind the counter at a Brookline jewelry store. Debra Davis was stunning. She had shiny blond hair, a big white smile, and long legs. Flemmi showered her with clothes, jewelry, even a car, and the two began to play house, first in a luxury apartment Flemmi kept in Brookline and later in a smaller apartment in Randolph, a suburb on the South Shore. By the late 1970s Flemmi had added another captivating blond teenager to his stable: he was fooling around with Debbie Hussey, Marion’s daughter. Stevie and Debbie could sometimes be seen tooling around in Flemmi’s Jaguar.

There were other women too, but these were the regulars. Although the troopers were never sure where the Chevy might land for the night—Brookline, Randolph, Milton, parts unknown—like clockwork Stevie would pick up Bulger at the housing project around midday. Flemmi would slide over, and Bulger would slip in behind the steering wheel. They realized that Bulger’s demeanor seemed to soften in South Boston, away from Lancaster Street. He greeted kids, waved to mothers, and stopped his car to allow elderly women to cross the street.

But even in Southie he had his moments. One day that summer O’Malley was following Bulger and Flemmi when Bulger turned down Silver Street. Bulger supposedly owned some property on the street, and his girlfriend, Teresa Stanley, lived there. Turning onto Silver, Bulger came upon a group of old men seated on the front stoop of one of the houses. The men were drinking. Bulger hit the car’s brakes and jumped out. The men scrambled off, but one was too slow to react. Bulger hit him across the face, back and forth. The man fell to the ground and curled up. Bulger kicked him. Then he grabbed the man’s hat and threw it down the street. Flemmi, meanwhile, looked up and down the street, keeping watch, but Bulger was done. He and Flemmi laughed hard, got back into the car, and sped away. O’Malley raced over to the bleeding man, but the man was no fool: he waved the trooper off, told him to get away. “I don’t know nothin’ and don’t bother me.” Even a drunk knew better.

While they were assembling their own intelligence about Bulger, the troopers also checked in with their criminal informants. One informant, code-named “It-1,” reported that starting that year “there was a large Money Bank at the garage on Lancaster Street, where the ‘Big Boys’ go to deliver money collected as a result of illegal gaming operations run by the North End. This garage is where the accounts are settled up.” Another informant, named “It-3,” told the troopers that “Bulger is a former lieutenant in the Howie Winter organization and is believed to be assuming control of the operation in Winter’s absence.” Another informant, “It-4,” told them that “Whitey Bulger and Stevie Flemmi were presently overseeing the majority of the sports betting, numbers action, and loan-sharking for the Boston area and in particular the Somerville area.”

The troopers tapped other informants as well, all of whom hooked Bulger and Flemmi up with the Mafia in a flourishing joint venture. By the time July rolled around, Fraelick, Long, and O’Malley felt they had enough probable cause in hand. In open view from the window was a case with the potential to stand as the hallmark of any investigator’s career: nailing the entire lineup—the Mafia and the Bulger gang. The troopers had put up with the squalor of the flophouse, logged the long hours of surveillance, and even gotten a little wacky: on the walls of their room they’d mounted the largest of the cockroaches they killed during the surveillance, transforming the “room kill” into a trophy.

By early July the troopers had witnessed plenty of street action; now they wanted to know what the mobsters were actually saying. They sensed they’d stockpiled enough intelligence and were eager to take their case to the next level—installing a microphone inside the garage.

▪ ▪ ▪

Several times that spring Long, along with his commander, met with Jeremiah T. O’Sullivan, still the top federal prosecutor at the New England Organized Crime Strike Force. Long briefed O’Sullivan on what he and his troopers were witnessing at the Lancaster Street garage. They came up with a plan in which the feds would provide funding for the state police bugging operation. They brought in a local prosecutor, Tim Burke, an assistant district attorney in Suffolk County, to prepare the court papers to win a judge’s approval.

Despite the federal funding, it would be a stand-alone state police effort—no other agency. It wasn’t as if the troopers could not work with the FBI; after all, Long had served as state police commander in Operation Lobster, the joint FBI and state police investigation that had involved Nick Gianturco. But there were the new rumors, especially after the race-fixing indictments when Bulger had eluded prosecution. The rest of law enforcement had begun wondering about Bulger and the FBI. But O’Sullivan, despite what he knew, told Long nothing—it was their case.

On July 23, 1980, Superior Court Judge Robert A. Barton approved Burke’s application for a warrant to bug the Lancaster Street garage. Pumped up, Long, Fraelick, and O’Malley went to work. None of them had had much experience when it came to electronic surveillance, but they’d make up in energy what they clearly lacked in expertise. They’d actually made a trip to Radio Shack to buy the microphones they were going to use. Then, to case the garage’s interior and get a sense of the layout of the office, O’Malley posed as a tourist needing to relieve himself. He wandered into the garage one day, looking lost and looking all around. Bulger confronted him, saying there was no bathroom, and sharply ordered O’Malley out.

It was all trial and error.

The troopers came to call their first attempt “the Trojan Horse.” They obtained a fancy-looking, souped-up van, pulled up the floorboards, and created crawl space for O’Malley. Then they replaced the floorboards, covered them with a shag rug, and filled the van with furniture. With a state police secretary at his side, Fraelick drove up to the garage late one midsummer afternoon. He told George Kaufman that he and his bride were new to Boston and having some car trouble. He was worried about leaving the van with all their belongings overnight on the streets of Boston. What if he pulled the van inside the garage and then first thing in the morning a mechanic could take a look at it?

Kaufman gave his okay and waved the van in. The “newlyweds” thanked Kaufman, promised to return in the morning, and walked off. Kaufman eventually closed up and left too. The plan was for O’Malley to emerge from the van during the night and let a crew in to install the microphones. But none of the troopers had counted on one of the winos from the flophouse across the street setting up right by the garage. O’Malley, bathed in sweat and grime, had no idea what was going on. He was not in radio contact with the others, but he could hear the wino making noise outside. The troopers improvised. Long had one of his crew go out and buy a case of beer. The trooper plopped down next to the wino and began feeding him beers. Once the man passed out, the troopers could move in. But waiting ate up precious time, and just when the man was going down Kaufman unexpectedly reappeared. Kaufman started yelling at the two men drinking at his garage, and he chased them off. By this time it was too late to pull off a bug installation. Eventually O’Malley emerged from his suffocating hiding spot only to learn that Long had called off the effort.

Their next try met with more success.

Early one evening the troopers parked a U-Haul truck snugly next to the garage. The truck not only carried a crew but also created a wall so that no one from the flophouse could look down onto the garage. Most nights the winos and wackos were yelling and hanging out the open windows in the sweltering heat. The truck took care of the flophouse follies. Then, after Kaufman left, two troopers dropped down by the side of the truck and kicked out a bottom panel of the garage door. The troopers crawled in and, with the help of a technician they had hired for the job, installed three microphones—one in a couch, one inside a radio, and one in the ceiling of the office. They left, replacing the panel on the garage door.

Bob Long and his troopers were ecstatic. But the operation went quickly downhill from there. Testing the reception, they faced technical problems. Instead of mobster talk, they were picking up pager calls for doctors at nearby Massachusetts General Hospital. The microphone installed inside the radio didn’t function at all. The one in the couch worked but wasn’t of much use, producing little more than a rush of sound, like a hurricane, when one of the mobsters, especially the oversized ones like Nicky Femia, collapsed into it. But they were getting transmission from the microphone in the office, and that was the prime location; after straightening out the hospital interference, it was soon up and running.

Then the sky fell in.

Bulger, Flemmi, and Kaufman mysteriously started looking up at the windows in the flophouse. Abruptly they altered their routine. Instead of talking in the office or in the open bays, Bulger and Flemmi held meetings inside the black Chevy. The office was now off limits. The troopers were stunned. They kept monitoring their bugs, but shortly after the gangsters moved their talk to the backseat of the Chevy, they had to stop coming to the Lancaster Street garage altogether. Early in August the court order permitting them to bug the garage expired. The troopers had their notes, a pile of great photographs, but nothing more. Bulger was gone.

▪ ▪ ▪

In the days before Long, Fraelick, and O’Malley failed in their bugging attempt, trouble had been brewing for the FBI. It began with a chance encounter at a Friday night party. John Morris, cocktail in hand, sidled up to a hulking Boston detective. The diminutive Morris still managed to talk down to him—the federal agent lording over a local cop. “You have something going at Lancaster Street?” Morris asked with a conspiratorial smile that urged: C’mon, you can tell me.

Taken aback, the detective put on a poker face to mask his surprise. A direct question about another agency’s secret investigation wasn’t expected cocktail chatter at a midsummer party. The question hung in the air, unanswered.

Morris pushed on. “If you have microphones in there,” he said, “they know about it.”

After some more dead air, the police detective finally replied, “I don’t know what you’re talking about.”

The detective moved away from Morris. But his heart was racing. The next morning he called Bob Long. The early morning phone call did not take Long completely by surprise. He had been sensing something was wrong. All that the bug inside the Lancaster Street garage’s corner office was picking up was a jaunty Whitey Bulger commending state troopers for the great job they did patrolling the Massachusetts Turnpike. Ballbusting or coincidence?

Long wasn’t entirely sure. But the more he thought it over, a pattern became clear. He and his troopers had watched for months from the flop-house across the street as Bulger harassed anxious gamblers who owed money and bantered with visiting Mafia dignitaries. Then, exactly one day after a bug was up and running inside the garage, Bulger had been praising highway patrols and, more important, changing his routine. Business conversations had moved from inside the office to the backseat of Bulger’s black Chevy parked inside the bay area.

Initially Long had figured that Bulger and Flemmi spotted the troopers across the way. But now word of Morris’s overture made Long realize that the problem was much worse than a blown surveillance. To Long, the gangsters’ new routine wasn’t just one of those things that happened—it was treachery. The call from the police detective confirmed the shocking truth that Long saw through a red haze of fury. And he became transfixed by two questions:

How did John Morris know about the state police bug?

And how did he know Bulger and Flemmi knew?

By Monday morning, August 4, 1980, it was war. The ranking state police officer, Lieutenant Colonel John O’Donovan, was on the phone complaining about the leak to the head of the FBI’s Boston office. The state police and FBI office were already accustomed to tangling over glory and credit for fighting crime in Massachusetts, but this kind of accusation marked the nadir of a strained relationship.

Faced with the angry finger pointing, law enforcement did what it always does—it held a meeting. The summit at a Ramada Inn in Boston convened four days after Morris’s party blunder. Attending was a who’s who of law and order: O’Donovan and Long from the state police, county prosecutors, Boston Police officials, an FBI official, and Jeremiah T. O’Sullivan.

O’Donovan presented the grievances of the state police. Looking around the room, he spiced his indignation with a small bluffing game. He claimed their bug had been “extremely productive” until it was tipped. And he said they knew Bulger and Flemmi were informants. Of course, the state police had no solid proof that Bulger and Flemmi were FBI snitches, but O’Donovan had a strong hunch about Bulger’s possible ties to the FBI, going back to an encounter he’d had with the gangster a couple of years earlier. O’Donovan recalled going to see Bulger at Marshall Motors. The issue was a threat against a state trooper from one of Bulger’s associates in the Winter Hill gang. Packing two guns, O’Donovan stopped by the garage to convince Bulger that any move against a trooper was a stupid idea. Bulger quickly assured the lieutenant colonel that nothing would come of the hotheaded rhetoric. Then the two chatted sociably about life along the law enforcement landscape, with one thing leading to another, and finally to the FBI. O’Donovan mentioned that he preferred the older agents in the Boston office to the younger ones, saying that newer agents like John Morris were too inexperienced in the ways of Boston. He made it clear that Morris and other young turks did not impress him.

About two weeks later O’Donovan took a call from a fuming John Morris, who wanted to know why he was badmouthing the FBI with Whitey Bulger. O’Donovan was brought up short and concluded that either the FBI had a bug planted inside Marshall Motors or Bulger was an FBI informant.

Morris’s indiscreet call only compounded O’Donovan’s mistrust for the FBI supervisor. O’Donovan saw the agent as a schemer who maneuvered behind a friendly demeanor. Another time he’d passed along a state police tip to Morris about a fugitive on the Ten Most Wanted List. The same day Morris and several agents raced to capture the terrorist bomber. There was no joint arrest, just an FBI press conference. O’Donovan and his troopers were forgotten on the sidelines.

But none of this was proof of skullduggery. It was just troubling background that an experienced policeman never forgot. And at the Ramada O’Donovan didn’t get into this kind of history. But neither did he and Sergeant Long disclose that the troopers, despite the setback at the Lancaster Street garage, were planning to take another run at Bulger and Flemmi later in August. Instead, O’Donovan focused on recapping the debacle at the garage, climaxed by his conviction that the FBI had compromised the bug. Between the lines the topic on the roundtable was nothing short of accusing FBI agents of a crime: obstruction of justice.

But the FBI men did not flinch—it was their kind of game. The bureau’s representative, an agent named Weldon L. Kennedy, one of the assistant supervisors in Boston, listened politely to O’Donovan of the state police. Once O’Donovan was done, Kennedy had little to say.

“We’ll get back to you,” he finally offered. But that was it.

After the meetings, however, the FBI in Boston went into spin cycle. Initially the bureau insisted that Morris had learned about the bug by putting two and two together: first, his own informants from the North End Mafia had detected “new faces” in the area, and second, Morris had heard that Boston Police were ordered to stay away from Lancaster Street. To a professional like Morris, there was only one conclusion to draw: something investigatory was under way. Morris even offered that his approach to the Boston cop was a well-meaning bid to use his insight as a warning to the troopers.

But O’Donovan and his troopers viewed Morris’s account as disingenuous at best and, during the weeks after the Ramada Inn summit, made it clear that they were not buying the FBI’s explanation. In turn, the FBI moved the tense, interagency dispute up a notch. The FBI said it had learned from its informants that any leak had come from within the state police; the collapse of the bugging operation was the state police’s own fault. The agent who had brought this new juicy intelligence to the table was John Connolly.

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Back at state police headquarters the troopers kept debating what went wrong, going over every move they’d made. They weren’t going to give up, not yet. They’d seen too much of Bulger and Flemmi.

They let a few weeks go by to give Bulger and Flemmi some room to move. Then they hit the street again, riding around to see if they could pick up the gangsters’ scent. It wasn’t easy, especially after the debacle at the garage. Bulger was crafty, a difficult mark. Behind the wheel of the Chevy he employed a number of evasive driving techniques. If he was approaching a traffic light and the light was turning yellow, he accelerated and raced through the intersection. Sometimes he simply ran the red light. He drove down a street and suddenly pulled a U-turn and came back at you. Sometimes he drove the wrong way down a one-way street, and Southie seemed cursed with one-way streets. He knew South Boston cold, and he often zigzagged his way through the old neighborhood rather than take a direct route to his destination.

But soon enough the troopers picked him up. Just before Labor Day Long, Fraelick, and O’Malley established that Bulger and Flemmi had a new pattern, and it revolved around a bank of public pay phones outside a Howard Johnson’s restaurant right off of the Southeast Expressway.

The new routine went like this. Nicky Femia drove into the HoJo’s parking lot, circled around, and then parked. He’d saunter over to the pay phones, look around, stuff a few coins into the phone, and make a call. The black Chevy pulled in a few minutes later, carrying Bulger and Flemmi. Then they climbed out and looked around, and each went into a telephone booth to make some calls. They chatted away, their heads bobbing and turning, always looking out over the parking lot and studying any vehicle that might drive by. Once off the phone, they drove off. The troopers, if they could keep up, followed them to Southie or into the North End, where they met up with any one of the number of underworld figures they used to meet in the bay and office of the Lancaster Street garage.

So far the investigation had focused on loan sharking and gambling, but the troopers now began to make out the hint of a drug connection. The troopers didn’t know at first who Frank Lepere was; in fact, a number of photographed wiseguys were written up in their logs as “unknown white male.” But showing one such photograph around, the troopers learned it was Lepere, a former Winter Hill associate who’d gone into the business of marijuana trafficking with Kevin Dailey of South Boston. Lepere had shown up at Lancaster Street carrying a briefcase; looking back, Long and his troopers realized “it wasn’t full of candy bars, that’s for sure.” After Labor Day the troopers had followed Bulger and Flemmi from the pay phones to South Boston, where the two gangsters met up with Kevin Dailey. This time Flemmi was the one carrying a briefcase. They met for an hour in the parking lot of a closed-down gas station across from the Gillette Company plant along the Fort Point Channel.

The next day at HoJo’s, on Friday, September 5, Femia caught the troopers’ attention when he tucked a small automatic handgun in his pocket before locking up his blue Malibu. Bulger and Flemmi pulled in, and then a short while later a gray Mercedes 450SL rolled into the lot. Driving the car was Mickey Caruana, who, at forty-one, was reputedly the biggest drug trafficker in New England. Caruana was the Mafia’s own drug kingpin, a brash high roller who answered to no one except Raymond L. S. Patriarca, the Providence-based godfather of New England. (In 1983 he would become a fugitive, fleeing a federal indictment for drug trafficking that charged him with netting $7.7 million between 1978 and 1981.) Bulger and Flemmi greeted Caruana. Femia stayed back while the three men went into the restaurant. The meeting lasted about ninety minutes. Outside, Bulger and Caruana shook hands heartily before splitting up.

It was all tantalizing stuff. There was another meeting with Kevin Dailey in Southie, and yet another encounter with the Mafia’s Larry Zannino, who arrived at HoJo’s in his blue Continental. Compared to the flophouse, the troopers’ command post was posh. They’d set up in a fourth-floor bedroom at HoJo’s overlooking the pay phones and were photographing and videotaping Bulger’s comings and goings.

Pulling all their intelligence together, the troopers went back to court. On September 15, 1980, Judge Barton approved their second bid to capture Bulger’s and Flemmi’s incriminating words. The troopers had all five pay phones tapped. The wiring was done two nights later, on a Wednesday night.

But once again the troopers came up empty. Eager and optimistic, they took up their position in their hotel room the next afternoon, awaiting their targets’ regular arrival. But one o’clock came and went. Two o’clock. Three o’clock. The hours passed. Bulger and Flemmi were no-shows. They didn’t show up the next day either, or the day after, or the day after that. Once again Bulger was gone.

Inside their hotel room the sullen troopers had a lot of empty time on their hands. The court order they had lasted until October 11, but Bulger never reappeared. They could have screamed and yelled, cursed the high heavens, but they didn’t. They didn’t trash the room. But they did talk obsessively about their plight, talk that went in dizzying circles. What the hell was going on?

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Maybe they were crazy, or at least too stubborn for their own good, but Long and his unit reviewed the intelligence they had amassed against Bulger and Flemmi and, despite their setbacks, decided to launch a third and final try. They all felt some pressure to produce something tangible—a prosecutable case—after investing more than six months of manpower and resources in the investigation. They also weren’t naive: with each failure the chances for success narrowed. Bulger and Flemmi were on high alert. But Long and the troopers were still fired up, and they decided to take a final shot at the high-riding crime bosses. “We didn’t think our chances were good,” Long recalled, “but we figured what the hell—go for it. If it doesn’t work out, we close the books on it and move on.”

Their target would be the black Chevy—installing a bug in the car would be their “Hail Mary” pass. The troopers had chased Bulger from the Lancaster Street garage and from the pay phones outside HoJo’s. From their surveillance they now saw that Bulger was using the car as a mobile office. For a few weeks in the fall the troopers once again eased off to give Bulger and Flemmi some breathing room. Resuming their surveillance in late 1980, they saw that Bulger and Flemmi continued to conduct most of their business in the Chevy.

Bulger’s new routine was to drive into the North End in the early afternoon and park outside of Giro’s. The restaurant, located on one of the neighborhood’s busier streets, Commercial Street, was only a few blocks from Angiulo’s headquarters at 98 Prince Street. Giro’s, like the garage before it, was a hub of underworld activity: wiseguys were moving in and out of the restaurant throughout the early afternoon. Sometimes Bulger or Flemmi went inside and sat at a table for a meeting with various underworld figures, but most of the time they sat in their car and hosted a stream of wiseguys who climbed into the Chevy, talked a bit of business, and then got out.

Following Bulger into the North End, it was a wonder the troopers did not bump into the FBI. The troopers, of course, didn’t realize it at the time, but for most of 1980 the FBI had been putting the finishing touches on its sophisticated plan to bug 98 Prince Street. The operation, code-named “Bostar,” targeted Gennaro Angiulo and the top tier of Boston’s Mafia. Throughout the year FBI agents had been combing the North End, documenting the daily rhythms at 98 Prince. John Morris, as supervisor of the Organized Crime Squad, was in charge, along with case agent Edward M. Quinn. John Connolly and a dozen or more agents were part of the top-secret team.

By the fall of 1980 strike force attorney Wendy Collins had already gone through several drafts of the Title III application to win the federal court approval the FBI needed to break into 98 Prince Street to install bugs. Even though Bulger and Flemmi were Connolly’s prized informants, the two had not been used to develop the probable cause the FBI needed for Wendy Collins’s Title III work-in-progress. Instead, the FBI was mostly relying on five or six other informants—all of them gamblers and loan sharks—who, unlike Bulger and Flemmi, regularly met with Angiulo inside 98 Prince Street.

Of course, it wasn’t as if Bulger had not been discussing the Mafia in his surreptitious meetings with Connolly. He had, but Connolly’s FBI reports for those sessions contained mostly secondhand Mafia gossip. Early in 1980, for example, Bulger described a “brawl” that had erupted at a Mafia wedding reception after a young hothead made the stupid mistake of “ridiculing Larry Zannino.” Instantly some of Zannino’s men attacked the young man, who “suffered multiple lacerations and a couple of broken bones.” Bulger told Connolly about Nick Giso, who was Bulger’s daily Mafia contact at the Lancaster Street garage and then at Giro’s. The Mafia, said Bulger, “is supposed to be upset with Nick Giso … because of Nick’s continual use of cocaine.” To his credit, Bulger did provide some information about the activities of the drug traffickers Caruana, Lepere, and Dailey. “Mickey Caruana and Frank Lepere were behind the load that was interrupted recently in Maine,” Bulger told Connolly in April. Bulger even gave Connolly Caruana’s phone number. But these Bulger reports did not include any disclosures by Bulger about the extent and nature of his own growing business ties to the marijuana and cocaine traffickers.

At Giro’s, Bulger and Flemmi met with a who’s who of Mafia associates of Gennaro Angiulo’s—Zannino, Danny Angiulo, Nicky Giso, Domenic F. Isabella, Ralph “Ralphie Chong” Lamattina, Vincent “Fat Vinnie” Roberto, and a steady stream of bookmakers and loan sharks. In March, armed with a 102-page sworn affidavit authored by Rick Fraelick and with accompanying surveillance photographs of Bulger and his Mafia contacts, the troopers went back to court.

Superior Court Judge John T. Ronan authorized their third bid for electronic surveillance on March 19, 1981; that court order gave them five days to get their bug in the car. But five days later the troopers were back in court seeking an extension to the original court order. They hadn’t been able to get near the car long enough to install their one-watt transmitting microphone along with a tracking device. Flemmi kept the Chevy at night, either in Milton or in Brookline at the apartment complex, Longwood Towers. Neither location was accessible. In Milton each time the troopers approached the car under the cover of darkness Flemmi’s dog went nuts. At Longwood Towers the state police technician actually got into the Chevy, but then a delayed car alarm went off. Fraelick threw a rag over the security camera, grabbed the technician, and fled, just ahead of a security guard and Flemmi himself.

The judge approved an extension, and the troopers, their hopes waning, devised their most ambitious plan. A trooper would stop Flemmi for a phony traffic infraction. The trooper would run Flemmi’s plate, inform him the Chevy had been reported stolen, and then order the car towed away. With the car in their possession, the troopers could install a bug before Flemmi retrieved it.

The trooper, Billy Gorman, stopped Flemmi one afternoon as he drove the Chevy through an intersection in Roxbury. Hidden but nearby, Long and the other troopers watched and monitored the cruiser’s radio. Gorman had been handpicked for the assignment; he was unflappable, and the mission called for a trooper who would not be drawn into an ugly exchange with the volatile gangster.

The cruiser’s lights flashed, and Flemmi pulled over. The trooper got out, and so did Flemmi. They headed for each other right there in the street. The trooper spoke first: “Did you see that old lady there you almost ran over?”

The many months of only being able to study gangster body language now ended abruptly, and at long last the troopers finally heard actual noise from one of their targets. Flemmi’s first words were hardly pleasant ones.

“What the fuck is this shit?” he shouted. No ordinary citizen, the gangster was not impressed by a trooper’s uniform and badge. His temper raced from zero to sixty in an instant. “Do you know who I am, you fuckin’ jerk? This is harassment!”

Methodically, Gorman asked Flemmi for his license and registration. “I don’t got no fuckin’ registration,” Flemmi yelled. “These are dealer plates, can’t you see?” The trooper calmly told Flemmi he should still have a registration. The trooper explained he was going to have to run the plate and that Flemmi would have to wait patiently. Gorman headed back to his cruiser, and Flemmi stormed off into a convenience store, where he began making telephone calls.

In the cruiser Gorman consulted with Long. The tow truck was summoned. The installation crew was waiting in the back lot of the nearby abandoned Mattapan State Hospital. Flemmi came back out of the store, and Trooper Gorman explained that the car had been reported stolen. Gorman and Long even play-acted on the cruiser’s radio, with Long telling the patrol trooper, “Please be advised that the vehicle comes back as stolen from Nassau County, New York, in July 1979.” Gorman told Flemmi the Chevy was going to be towed.

Flemmi was apoplectic. Then he uttered the words that made Long’s and every other state trooper’s stomach turn to mush. “You tell fuckin’ O’Donovan that if he wants to bug my car so bad, I’ll drive it right up to fuckin’ 1010.” “O’Donovan” was obviously Lieutenant Colonel John O’Donovan, Long’s commander, and “1010” was a reference to state police headquarters. Flemmi knew.

It was over.

Flemmi went back inside the convenience store. The car was towed away, but even before its arrival behind the hospital Flemmi’s lawyer was telephoning O’Donovan screaming about the blatantly absurd seizure of the car. The state police commander kept a stiff upper lip and didn’t give the lawyer anything, saying the car had come back as reported stolen. But the troopers all knew the ruse was up. Long told the troopers not to even install the bug. Don’t give Bulger and Flemmi the satisfaction of taking apart the car and finding the bug, he said. Let them wonder, maybe they’ll get a little paranoid.

This was the troopers’ only consolation. They’d thrown the Hail Mary, and it had fallen woefully short. Despite their many months of successful surveillance, they’d lost in the streets against Bulger and Flemmi. They may have seen Bulger and Flemmi joined at the hip to the Boston Mafia, but they would not be taking them to court. They’d been outmaneuvered at every turn. But even in failure the state police had triggered, unbeknownst to them, a massive internal crisis over at the FBI, a crisis that, more than any other in the FBI’s long history with Bulger and Flemmi, posed the biggest threat to the cherished deal Connolly and Morris had with the two gangsters.