Ex-G-Man John Connolly Jr. Helped Mobster Whitey Bulger Escape 16 Years Ago

​More than a decade-and-a-half of being on the lam finally caught up to James "Whitey" Bulger. The F.B.I. announced today that they nabbed the 81-year-old Boston mobster in Santa Monica by focusing on locating his longtime girlfriend, who was arrested with Bulger. His brutal ways were depicted on the silver screen by Jack Nicholson in Martin Scorcese's The Departed, but for a deep sketch into Whitey's underworld, we recommend reading former New Times staff writer Tamara Lush's cover story on the G-Man who helped Bulger make like David Copperfield.

See, Whitey was a snitch for FBI agent James Connolly Jr., who is appealing a Miami-Dade murder conviction for leaking information to Bulger that prompted the gangster to kill a Boston businessman in Florida. Connolly was also convicted and sentenced to 10 years on federal racketeering charges. Prosecutors say the ex-federal investigator tipped off Bulger in 1995 that he was going to be indicted for racketeering and his participation in 19 homicides.

Here is an excerpt of Lush's story describing how Connolly got too cozy with Bulger after winning praise from his FBI bosses for landing a high-profile rat:

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.

Meanwhile Whitey's criminal enterprise -- loan-sharking, extortion, drug-dealing, bookmaking, murders of assorted underworld figures -- continued without a hitch. His influence flourished to some degree because the Italians had been rendered impotent. And since Whitey also snitched on other, minor hoods in Southie, his competition was reduced.

Other law enforcement agencies tried to investigate and wiretap Whitey, but the operations always inexplicably failed. Whitey and Flemmi seemed untouchable. Many cops around Boston wondered just what kind of information was passing between the FBI and Whitey. "People suspected Connolly had a relationship with Flemmi and Bulger," commented the anonymous Massachusetts lawman. "There was no constraints put on him whatsoever in the handling of those informants."
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Francisco Alvarado was born in Nicaragua and grew up in Miami, giving him unique insight into the Magic City and all its dark corners. An investigative reporter with a knack for uncovering corruption, Alvarado made his bones as a staff writer at Miami New Times and remains in dogged pursuit of the next juicy story.