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Then Connolly returned to New York for his job, where, in 1972, he netted a big fish: "Cadillac Frank" Salemme, a known Italian Mafia boss. The then-32-year-old agent chased Salemme through the streets of the Upper East Side and arrested him at gunpoint. Salemme was convicted of the attempted murder a car bombing of an attorney and sentenced to twenty years. The FBI rewarded Connolly with a transfer back to Boston, where he bought a home near his alma mater, South Boston High.
Being the new agent in the office, Connolly wanted to impress his bosses by solving another difficult case.
The agency's main target in those days was La Cosa Nostra the Mafia and Connolly knew of someone who had inside information about the Italian mob in Boston: Whitey. He, too, had returned to Southie; he had moved in with his mother back in the Old Harbor projects. Billy, his brother, had been elected to the Massachusetts Senate by this time (Connolly was one of his campaign workers) and had nine children.
Though Whitey worked as a janitor at a local school, he re-established ties with the underworld. In the early Seventies, Whitey plied his trade after school hours, extorting money from shylocks and bookmakers often with brutal force. He and his buddies, known as the Winter Hill Gang, were in an all-out war with the Italians on the city's North End.
On September 18, 1975, Connolly asked Whitey to meet him on a beach several miles south of the city, in the shipbuilding town of Quincy, according to public records. As a full moon rose into the sky, the agent parked his old Plymouth in the empty lot. He could see the Boston skyline in the moonlight.
Then without warning, the passenger door swung open. It was Whitey.
"What the hell did you do, parachute in?" Connolly asked his old friend, who had parked on a side street and walked over. Out of respect, Connolly called him Jim, never Whitey.
The two men made small talk. About what, the records aren't clear. Then Connolly offered a proposal: "You should use your friends in law enforcement." Whitey, he suggested, should rat out the Italians.
Whitey mulled it over for a couple of weeks. The men met again at the same beach.
"All right," Whitey said, according to the Boston Globe, which published groundbreaking work about the Irish thug. "Deal me in." He had no love for the Italians and figured that informing on them would be better than fighting them in the streets.
"If they want to play checkers, we'll play chess. Fuck them."
Connolly's FBI superiors knew exactly what they were doing when they authorized him to use Whitey as an informant; other agents had tried for years to win over the mobster. Cops, politicians, and average citizens in Boston all knew of Whitey's violence and increasing influence in Boston's underworld. The police had been stymied by his ability to slip out of indictments; the politicians (especially his brother Billy) looked the other way; and the residents of Southie considered him a hero.
So to have attracted Whitey as an informant was a coup for the young agent. Connolly's superiors were proud of his work. Colleagues were a bit jealous.
Soon Whitey convinced a friend to snitch. Steve Flemmi was a double-chinned, lug-headed Irish-Italian from Southie. He had earned the nickname "The Rifleman" while serving in the Korean War he was a particularly good killer and that nom de guerre applied on the streets as well.
The pair seemed the least likely men in Boston to be rats.
Flemmi was six years Whitey's junior and one of the few people the gangster trusted. A curly-haired brothel owner, he was great with women (he liked young blonds and would later kill two of them) and even better with local gangsters; Italian Mafia leaders liked and confided in him, yet he wasn't a "made" man. And Flemmi was no stranger to the FBI. In the Sixties he had secretly fed another agent information about the largest family of Italian gangsters in New England at the time and then evaded a murder indictment.
Between 1975 and 1983, Whitey and Flemmi gave Connolly enough information for a big arrest: the elderly Gennaro Angiulo, head of the Italian Mafia in Boston. Then the agent helped dismantle the Patriarca family, another big win. Thanks to his Irish gang friends, Connolly knew where the Italians were, what they were doing, and who they were talking about; the information given to him often led to wiretaps that captured illegal deeds.
Connolly got rave reviews from his superiors and reveled in the glory of the high-profile cases.
Perhaps too much.
"John was a dapper guy," says one high-ranking Massachusetts law enforcement official who is close to the case. "Well dressed, flashy, more than you would expect from an FBI agent. He wasn't your run-of-the-mill FBI agent. He knew all the power brokers." Indeed even Whitey poked fun at his foppishness; he would often call Connolly "Elvis" because the agent always perfectly combed his hair up and back.
Connolly's informant work certainly impressed the G-men in Washington, D.C., in the Seventies and Eighties. He was asked to lecture other agents about "informant development tactics and techniques" at the FBI Academy in Quantico, Virginia.