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

Manny Casabielle
Ex-FBI Agent John Connolly Jr. helped Whitey Bulger elude capture.
​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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Matthew Melanson
Matthew Melanson

John Connolly was a fall man and nothing else. He was strictly following orders from his superiors. Whitey was an FBI informant, meaning he could still perform some illegal activities. Perhaps Connolly was in the wrong, but not wrong enough to spend the rest of his life in jail. John Morris, who went before the court and threw Connolly under the bus, should be behind bars for the rest of his life. He was the supervisor; he gave the orders. John Connolly should be a free man today. Maybe now that Whitey is caught, he may be able to.


John Melton
John Melton

Wrong...Se the My Lai Massacre...Just following orders is not an excuse...there has to be a line where morals and character overcome direct orders...No excuse


connolly was a greedy, crooked cop ! He is just as guilty of murder a Whitey and Steve Flemmi. 

Lewis Alton
Lewis Alton

Connolly was a fall man?! Ridiculous!  He knew exactly what Bulger was doing and considered it a win win situation between him and Bulger, Connolly getting great tips on criminals and Bulger's criminal competition being eliminated.  Moreover, how do you escape the fact that Connolly tipped Bulger off, allowing him to escape.  Wake up!  

Matthew Melanson
Matthew Melanson

So Connolly was suppose to give up everything he had worked so hard for because his direct boss was giving him orders that were of questionable morality?

From a study in 2005: In an analysis of 120 informant files from around the country, the Justice Department's inspector general, Glenn A. Fine, found that FBI agents violated procedures in 87 percent of the cases, including some in which informants allegedly engaged in illegal activity without proper oversight or permission.

Connolly wasn't alone; the majority of the FBI were allowing illegal activities to go on. Why? Because they need information which lead to other arrests; which helped lead to the arrest of many Italian mobsters, including boss Gennaro Angiulo. Connolly made it clear to Whitey and Flemmi: that they could continue with some of their illegal activities, but that violence was not allowed. So how could Connolly have known that the murders were going to happen? The perfect example of why he should not be in prison for second degree murder.

Matthew Melanson
Matthew Melanson

And John Morris wasn't? Morris is a free man because he placed all the blame on Connolly. How is the fair? He was blubbering sissy in court. Unacceptable, seeing how Connolly was following DIRECT ORDERS from Morris. Morris let Whitey and Flemmi do as they please because they kept him financially sound. That, and providing him with all the top notch booze he wanted. Connolly was following orders. (and don't even think of comparing it to Nazi's following the orders of Hitler; I know a lot of people are thinking about that for a comparison; Connolly never pulled the trigger.) Even Kevin Weeks wimped out after 2 weeks in prison; the same man who would have broken someone's neck had Whitey winked at him. John 'Red' Shea was the only one who kept true to South Boston way; keeping your mouth shut. Sure he wrote about it, but only he after he served his time without rolling over on someone else. And his book was excellent too. Whether or not Connolly informed Whitey about the arrest coming down on him, it still took the FBI over 15 years to find him. Connolly is not responsible for the murder charges. Racketeering charges? Perhaps. But not 40 years for something there is no proof of. Sentencing Connolly to 50 years in prison isn't justification...it's just a way for the FBI to cover their own asses.


Don't forget Howie. He never rolled. He finished a race fixing jail term in 87. In 1993, he was caught dealing cocaine. When the FBI told him that Whitey had been a snitch all those years they offered him a deal if he would inform on Bulger, He refused the deal telling the FBI he was no "rat", despite facing another decade behind bars, which he would serve, being released from prison in July 2002.

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