Since the 1960s, Flemmi lived on-and-off with Marion Hussey in a house just over the Boston city line in Milton that once belonged to Flemmi's parents. He kept Hussey as his common-law-wife since he'd never divorced the woman, Jeannette A. McLaughlin, he'd married in 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 blonde 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 added another captivating blonde teenager to his stable, when he began 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. And while the troopers were never sure where the Chevy might land for the night -- Brookline, Randolph, Milton, parts unknown -- like clockwork Stevie picked up Bulger at the housing project around mid-day. (Flemmi would slide over and Bulger would slip in behind the steering wheel. They realized that Bulger's demeanor in South Boston seemed to soften 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 own 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, "I-4," told them that "Whitey Bulger and Stevie Flemmi were presently overseeing the majority of the sports betting, numbers action and loansharking 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 in hand. They'd witnessed plenty of street action, now they wanted to know what the mobsters were actually saying. 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 line-up, 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'd killed during the surveillance, transforming the "room kill" in trophies. By early July they sensed they'd stockpiled enough intelligence and were brimming with restlessness about taking their case to the next level -- by installing a microphone inside the garage.
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