by Dick Lehr
Morris greeted his guests. It was the first of many such gatherings to come. “It was more social than anything,” Morris said. The easy tone of the evening conveyed the feeling that they all belonged to something special, that the playing field of Boston was theirs. Morris was one of many government officials who would recognize eventually that in this instant the rule book was being put aside for good. Something much stranger than the proper, arm’s-length FBI informant relationship was going on in Boston. But at the time Morris went ahead, opened some wine, and filled everyone’s glass. Bulger, it turned out, had indeed brought a gift, a token of affection revealing that the gangster had a sense of humor. He presented FBI agent Nick Gianturco with a little wooden toy truck, a remembrance of the agent’s undercover work in the Operation Lobster hijacking case.
“It wasn’t an adversarial relationship,” Gianturco said afterward. Everyone was happy.
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 SIX
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 coveted by just about any Bostonian—a couple of 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.
No question, 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, Theresa 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 Theresa’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 handpicked 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 ousti
ng 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 they took 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 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 of 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 ove
r, grabbed the french fries, and began whipping them at Femia. He whipped french fries into Femia’s chest and into Femia’s 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, just over the Boston city line in Milton, that once belonged to his parents. He kept Hussey as his common-law wife since 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.