The Strange Story of Notorious Gangster Whitey Bulger: ‘Paradise Lost’ Filmmaker Joe Berlinger on His Controversial Documentary

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James J. “Whitey” Bulger was a notorious Boston gangster who ruled the city before going on the lam for 20 years as one of the FBI’s Most Wanted. Then he was found (and tried), last summer, in his eighties. While he was a fugitive, his younger brother Billy grew into the most powerful politician in Massachusetts, reigning as the head of the State Senate. On top of all that, Whitey may have just been an FBI informant, turning on his friends and associates in order to stay clean. It’s hard not to look at the story as a collection of myths: two brothers who both grow up to become leaders in their respective fields, on opposite sides of the law. A notorious crime lord who may have been a rat. The contradictions are irresistible to a host of storytellers.

On film, he was the inspiration for Jack Nicholson’s crime kingpin in The Departed, a character so evil that he wears a Yankees hat. (Which, well: unrealistic.) The largely forgotten Showtime series Brotherhood involved a powerful New England politico and his crime lord brother, a nod to the irresistibly Greek, nearly Shakespearean roots of Whitey’s story. And noted Irishman Johnny Depp is currently wearing all of the makeup and blue-eye contacts in order to film Black Mass, based on the reported book about Whitey’s reign, with horrific casting of a bunch of thugs from the greater Boston area. (Depp and human lizard Benedict Cumberbatch are the Bulger brothers, for one. I could rant about this. I am a native.) It is already creating controversy in Boston as to whether it’s “glamorizing” Whitey’s life. Regarding nonfiction, there’s been a series of books about the notorious criminal and his associates, ranging from Black Mass: Whitey Bulger, the FBI, and a Devil’s Deal to Whitey, many of them written by longtime reporters for The Boston Globe.

In the new documentary Whitey: The United States of America v. James J. Bulger, filmmaker Joe Berlinger, best known for the essential Paradise Lost series, investigates why “Whitey,” as he was known, reigned over Boston for decades with no repercussions and then went on the lam as the FBI’s second-most wanted (after Osama Bin Laden) for 16 years, only to be brought on trial for 33 charges, including 19 counts of murder, at 83.

“I’m an advocate for crying out when there’s corruption,” said Berlinger, in an interview in New York. “And as a storyteller, I’ve been fascinated by the mythology of this guy, how he’s passed into this cultural status where there’s multiple versions of him, to the point that some of the people in Southie think he’s a hero because of how he handled the busing crisis… I’m not saying everyone revered him in Southie, but he certainly passed into this myth.”

It’s a talking head-heavy film, filled with the voices of Bulger’s associates (his right-hand man Kevin Weeks, a thuggish Danny McBride IRL, will be played by Friday Night Lights‘ Landry in Black Mass), Bulger’s legal team, law enforcement, the still-raw-with-pain families of Bulger’s victims, reporters (current and former Boston Globe employees), and even Bulger himself, speaking over the phone. Berlinger covers the trial, where he doesn’t have access to courtroom, instead using voice-over and subtitles to get the moments across, and he covers Bulger’s legal perspective regarding the trial, most controversially positing that, potentially, Bulger was not an informant, that it was a juiced-up charge. While Berlinger goes into that idea with Bulger’s legal team, it doesn’t come out in much detail during the trial, since Bulger doesn’t take the stand and he’s not allowed to use his “immunity defense.”

This angle — and the implications that it carries for Boston media, Boston law force, and the FBI — has made the film a subject of some controversy. Kevin Cullen of The Boston Globe has been particularly vocal, writing that “Berlinger’s documentary, in an attempt to put its own stamp on a story so often told, lends undeserved legitimacy to Whitey’s unsubstantiated claim that he wasn’t an informant. The film ignores much of the overwhelming evidence in the public record, and the resulting impression is so guileless and sympathetic to Whitey as to be disingenuous.”

Berlinger, on the other hand, feels that local media painted Bulger’s claims as a “sideshow,” not digging into the evidence that the documentary presents (which is troubling, and certainly convincing): “To me that represents an inherent conflict of interest. The media is the watchdog of society, and the only people who are going to expose corruption is an engaged press corp.” He mentions Dick Lehr and Gerald O’Neill’s Black Mass, a book from 2000 that was published “before the Congressional hearings, before a lot of this ugliness has come out… For the reporters to not seriously investigate the claims that Bulger was making, I felt that was a conflict of interest by people who were in control of the story.”

Berlinger’s film is remarkably dense, nearly going minute by minute into the trial minutia, but he mentions — and is correct — that for people who are unfamiliar with Whitey’s story, and the details, the film is paradoxically “superficial,” in a fashion. “I used the trial as a springboard. Billy Bulger did not figure into that trial, so we did not tell that story. I wish I could’ve gone more into the textures of what makes Southie such a particular place.”

But even though Berlinger is honest about the film’s faults, it’s still a gripping, thorough documentary that raises real questions about the justice system, and whether our institutions that are supposed to protect us — the police and the FBI — are really trustworthy. For the filmmaker, the work is about “the depth of the loss of faith” that the people watching Bulger’s trial and the city of Boston felt, “which to me demands a kind of clearing of the air about how Bulger was made possible.” The trial didn’t serve that purpose.

Bulger’s story remains, in its way, mysterious. Maybe he wasn’t a rat. Maybe he wasn’t a very good informant. He’s trying to burnish his own narrative at the end of his life, claiming he’s a good bad guy, a Robin Hood who didn’t snitch and didn’t hurt women. We know that he’s a murderer, criminal, and liar. But the digging that Berlinger does, showing the people and community affected by this man’s life of crime — that’s important. More people should know about it, about what Whitey was like in the real world — before he becomes, again, just another image in the flickering lights. Sadly, though, the story of Whitey Bulger, a thug who murdered people and committed crimes against society, is likely to remain burnished in the near future. Berlinger notes, rightly: “More people will see that Depp movie in its first hour of release than in the lifetime of this film.”