Whitey Bulger: Snitch, mob boss, or Robin Hood?

Rick Klein, Richard Cooldige, Alexandra Dukakis, and Jordyn Phelps
Power Players

Top Line

Between the upcoming biopic “Black Mass” starring Johnny Depp and Jack Nicholson’s character in the hit movie “The Departed,” the mystique surrounding infamous Boston crime kingpin James “Whitey” Bulger, who inspired both characters, has captured the public’s fascination.

But interest surrounding the notorious gangster is not limited to Hollywood. Enter Academy Award-nominated documentary filmmaker Joe Berlinger, whose documentary, “Whitey: The United States of America vs. James J. Bulger,” gives viewers an up-close look at Bulger’s life story and his 2013 trial.

“I think he has an irresistible narrative,” Berlinger told “Top Line” in an interview. “Here's a guy who was on top of Boston's criminal empire for 25 years, not even charged [with] so much as a traffic ticket. Whitey rises to the top of Boston's underworld, and he has a life of crime, extorting and killing his way to the top.”

A point permeating the film is the relationship between the notorious mobster and the FBI. The FBI has long maintained that Bulger was their informant; but Bulger, who has been perversely heralded by some who said he did more good than bad for his South Boston community as the “Robin Hood of Southie,” claims that the reverse was true.

“[He] had an unusual relationship with the FBI,” Berlinger said. “The conventional narrative is he was an informant, and while he was an informant he was eliminating his rivals and, at the right moment, when the heat was on and he was about to be indicted, his friends in the FBI tip him off, and he goes on the lam.”

Sixteen years passed before the FBI officials took Bulger into custody, finding him across the country in Santa Monica, California, in June 2011. Bulger returned to Boston for a federal trial and faced 19 counts of murder and 32 other serious charges, of which he was ultimately convicted of 11 and 22 respectively.

The 2013 trial, at which the family members of Bulger’s victims finally got their day in court, is the backdrop against which Berlinger’s film explores the defense’s central claim: that Bulger was not an FBI “snitch.”

“What my movie tries to explore is some of the claims of the defense that Bulger, in fact, was not an informant -- that there was evidence that demonstrates the relationship was much more corrupt,” Berlinger said, later adding that the film does not definitively conclude whether or not Bulger was an informant.

Berligner pointed to the informant file kept by FBI agent John Connolly, who was assigned to Bulger, as an example of questionable evidence from the government.

“It’s full of information that's not unique, where there are duplicative sources, sometimes from other informant files,” he said. “The very definition of an informant file is one that is replete with unique information that directly leads to a prosecution.”

The film also airs the account of former FBI agent Bob Fitzpatrick, who went to interview Bulger at his house for what was supposed to be a one-on-one meeting and was surprised to find Connolly there, as well.   

“[Bulger] told me, ‘I'm not an informant. I pay them, for information -- not the other way around,’” Fitzpatrick said in the film.

But whatever validity there may be to Bulger’s claim, Berlinger said, is diminished by the fact that he chose not to testify during the trial.

“I think his tale would have been evidence that there was institutional knowledge both at the FBI and Department of Justice that Bulger was on the streets killing people while not necessarily being an FBI informant, because he denies he had a special relationship with the FBI.”

For more of the interview with Berlinger, including more about his doubts regarding the government’s case in the trial, watch this episode of “Top Line.”

ABC News’ Tom Thornton contributed to this episode.