Whitey Bulger - FBI Informant

FBI Informant

In 1971, the FBI, searching for reliable information in their battle against the Patriarca crime family, approached Bulger and attempted to recruit him as an informant. FBI Special Agent Dennis Condon was assigned to make the pitch. However, Condon reported that Bulger was too concerned about his own safety to start working with the FBI.

In 1974, Bulger became partners with Stephen Flemmi, an Italian American mobster and FBI informant since 1965. Although it is a documented fact that Bulger soon followed Flemmi's example, exactly how and why continues to be debated. Special Agent John Connolly frequently boasted to his fellow agents about how he had recruited Bulger at a late night meeting at Wollaston Beach inside an FBI issue car. Connolly allegedly said that the Bureau could help in Bulger's feud with Mafia underboss Gennaro Angiulo. After listening to the pitch, Bulger is said to have responded, "Alright, if they want to play checkers, we'll play chess. Fuck 'em."

Author Howie Carr alleges that Bulger had been an off-the-books informant since the 1940s. Carr dubiously claims that a teenaged Bulger worked as a male prostitute in Boston's gay bars. Carr also claims that Bulger was blackmailed into informing after Special Agent H. Paul Rico tailed him into a gay bar. This has never been confirmed, however.

Kevin Weeks dismisses all of these allegations. According to Weeks, the charismatic Bulger, "had more women than Hugh Hefner." As for Bulger's informant status, Weeks considers it more likely that Bulger's partner Stephen Flemmi had betrayed him to the FBI. He writes of his belief that Bulger was caught between a rock and a hard place: supply information to the FBI or return to Federal prison.

In 1997, shortly after The Boston Globe disclosed that Bulger and Flemmi had been informants, Weeks met with retired FBI Agent John Connolly, who showed him a photocopy of Bulger's FBI informant file. In order to explain Bulger and Flemmi's status as informants, Connolly said, "The Mafia was going against Jimmy and Stevie, so Jimmy and Stevie went against them."

According to Weeks,

As I read over the files at the Top of the Hub that night, Connolly kept telling me that 90 percent of the information in the files came from Stevie. Certainly Jimmy hadn't been around the Mafia the way Stevie had. But, Connolly told me, he had to put Jimmy's name on the files to keep his file active. As long as Jimmy was an active informant, Connolly said, he could justify meeting with Jimmy and giving him valuable information. Even after he retired, Connolly still had friends in the FBI, and he and Jimmy kept meeting to let each other know what was going on. I listened to all that, but now I understood that even though he was retired, Connolly was still getting information, as well as money, from Jimmy. As I continued to read, I could see that a lot of the reports were not just against the Italians. There were more and more names of Polish and Irish guys, of people we had done business with, of friends of mine. Whenever I came across the name of someone I knew, I would read exactly what it said about that person. I would see, over and over again, that some of these people had been arrested for crimes that were mentioned in these reports. It didn't take long for me to realize that it had been bullshit when Connolly told me that the files hadn't been disseminated, that they had been for his own personal use. He had been an employee of the FBI. He hadn't worked for himself. If there was some investigation going on and his supervisor said, 'Let me take a look at that,' what was Connolly going to do? He had to give it up. And he obviously had. I thought about what Jimmy had always said, 'You can lie to your wife and to your girlfriends, but not to your friends. Not to anyone we're in business with.' Maybe Jimmy and Stevie hadn't lied to me. But they sure hadn't been telling me everything.

A federal judge ruled on September 5, 2006, that the mishandling of Bulger and Flemmi caused the 1984 murder of informant John McIntyre. As a result, the McIntyre family was ordered to receive more than $3 million from the U.S. Federal Government. The judge stated the FBI failed to properly supervise their own agent John Connolly (convicted and jailed in 2002) and also failed to investigate numerous allegations that Bulger and Flemmi were involved in drug trafficking, murder, and other crimes over decades.

In a 2011 interview, Stephen Flemmi recalled, "Me and Whitey gave shit, and they gave us gold."