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.
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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