Whitey: United States of America v. James J. Bulger

Intentionally or not, the tired myth of the noble gangster gets another rigorous workout in Joe Berlinger’s promising but undercooked Whitey Bulger documentary. Fortuitously hitting theaters well before Scott Cooper’s fictional (and likely mythological) take on Bulger’s life, Whitey doesn’t try to be the feature-length nonfiction take on the South Boston crime lord. Instead, true-crime documentarian Berlinger (co-director of the Paradise Lost documentaries on the Memphis Three) zeros in on the sort of thing he normally does best: the trial itself.

Vindictive, ambitious, and murderous to a fault, Bulger was a nasty piece of work. He was just the kind of man who could rise to the top of the Winter Hill Gang, the Irish crew that ran a good part of Southie from the 1970s to the ‘90s. In 1995, after decades of extortions, burglaries, and murders that impressed even the hard-botten people living in Southie’s decrepit public housing, Bulger disappeared from view. He was arrested in 2011, after being discovered living near the beach in Santa Monica with his girlfriend. Berlinger runs through the background on Bulger at a fast clip, laying out just enough background for the fairly anticlimactic trial that followed.

The film’s structure is unevenly balanced between the 2013 trial (and following the emotional toll that takes on Bulger’s victims and their families) and examining Bulger’s defense, much of which rides on the abysmal conduct of law enforcement in the case. The latter ends up comprising the bulk of the film, since film cameras weren’t allowed in the courtroom. The ease with which Bulger was finally apprehended — the FBI, which had long included him on their Most Wanted List, sometimes just under Osama bin Laden, ran TV ads with his picture and a phone number to call — leads some of Berlinger’s interviewees to speculate on why exactly it took so long for him to be caught. A theory is even advanced that the FBI didn’t particularly want to catch him. Whitey is able to run with that idea, despite the paucity of much supporting evidence, entirely because the FBI’s earlier record regarding Bulger was so atrocious.

For much of Bulger’s underworld reign, he was working in close concert with Southie childhood acquaintance and FBI agent John Connolly. As reported in the groundbreaking book Black Mass — the basis for Cooper’s film; Dick Lehr and Gerard O’Neill both appear in Berlinger’s film — Bulger provided information on local Italian gangsters. In return, Connolly reportedly gave Bulger’s gang the run of the town, under certain conditions. It was a canny deal, fattening the confidential informant files of the frankly rather sycophantic Connolly while removing Bulger’s rivals from the scene.

This would be gruesome enough. But once Berlinger tries to turn the behavior of Connolly and other Bulger abettors like U.S. Attorney Jeremiah O’Sullivan into a wide-ranging conspiracy, Whitey starts to fall apart. The tone of the film is slanted from the start, with Bulger’s eager-to-please defense team practically inviting Berlinger’s crew in for coffee, while the prosecution is limited to a few robotic sound bites. More distasteful is the deference shown to Bulger himself. While Berlinger does illustrate the long-term pain left by Bulger’s terroristic legacy with its lengthy segments on his victims, the film does little to challenge his repeated assumptions (mostly through counsel, but once over the phone) that he never ratted. By the end of the film, it can’t help but read as another of Bulger’s self-mythologizing claims (like the since-disproven one that he didn’t deal drugs) that once made him a false Robin Hood for Southie.

As a filmmaker, Berlinger deserves credit for not just rehashing old material, and for trying to find a fresh slant on an already overdone corner of American organized crime (indeed, nearly everybody in the film remotely connected with Bulger seems to have written a book). But as a journalist, he should have realized that there was less of a story to dig up here than he thought.