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 over, 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.