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.
There were other women too, but these were the regulars. While 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, Theresa 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?