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Organized crime has been the worst kept secret in America since the early 1900s and big cases have been made against a number of mafioso heavyweights over the years. But for all the Italian goodfellas who got their comeuppance, one man remained largely untouched with a stranglehold over the city of Boston, only recently having been arrested in Florida, when he was in his 80s. Why did it take so long to catch him? Why, with all the murders he’s supposed to have committed directly or indirectly as the head of the Irish mob, was he left to his own devices in the ’70s and ’80s? This is very much the focus of the new documentary Whitey: The United States of America Vs. James J. Bulger. Did Whitey Bulger remain out of custody because he was an informant, like the FBI says, or was he just that good, like he maintains? Either way, he kept a reign of terror going for decades.

The film, directed by Joe Berlinger, takes an interesting approach to its subject: at no point is anyone saying, either on the prosecution or the defense, nor indeed any of the witnesses and victims, that Whitey Bulger is anything other than guilty of being a mobster. The real tenet of the defense attorneys’ position is that Bulger was not an FBI informant the way it states in the official records, that he had relationships with members of the FBI but it was he getting the information, and not the other way around, and that the FBI claiming his cooperation was a cover-up for their own corruption. Whitey has no problem being thought of as a horrible, violent murderer who ruined many people’s lives, but he needs to clear the air and prove he’s not a grass. The twisted criminal mind.

What I think the movie does very well is balance the history of the FBI and local police’s interactions with Bulger throughout the years with interviews during his 2013 trial by victims and family members of victims of his years of unfettered theft, racketeering, extortion, assault, and murder. The intense anger these people have toward Bulger and their mistrust of the system that let him get away with it for so long is palpable, and their outrage is one of the most sobering aspects of the film.

For awhile it looks as though the film will just be a chronicle of Bulger’s life in organized crime, but it quickly becomes a very compelling mystery concerning FBI cover-ups and whether or not a conspiracy existed to keep him in power at the expense of lives in Boston. Another mystery springs up after one of the witnesses we meet in the early part of the film suddenly disappears mid-trial. It’s never explained entirely what happened, but there is a strong suggestion that, even at 82, Bulger’s influence might run deep.

Whitey: The United States of America vs. James J. Bulger is one of the most compelling true crime documentaries I’ve seen in a long, long time. It deftly weaves histories and mysteries all surrounding the man who was at one point #2 on the FBI’s 10 Most Wanted List behind Osama bin Laden, and who was also the inspiration for Jack Nicholson’s character in Martin Scorsese’s The Departed. There isn’t any of the glamour or romanticism in the Irish mobs of Boston the way there is with New York’s Italian families; just a lot of violence and a lot of corruption. It’s a fascinating, and troubling, two hours.