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It's hard to think of a more malicious and sadistic character in recent U.S. criminal history than James (Whitey) Bulger.

His crazed Machiavellian ways provided the inspiration for Jack Nicholson's bloodthirsty turn in The Departed, and his life is scheduled for two further Hollywood takes, one starring Johnny Depp, the other Matt Damon.

The reason for filmmakers' fascination is clear. Once the country's most-wanted gangster, Bulger was caught in 2011 and charged with 19 murders and a laundry list of other criminal activity that took place during his 20-year reign of terror as the head of Boston's underworld.

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And yet, he's only the second-most odious part of the case laid out in director Joe Berlinger's Whitey: United States of America v. James J. Bulger.

The darkest part of this tale is the rot it reveals within the U.S. justice system. As several characters in the documentary outline, Bulger's crimes came with an implicit seal of approval from the U.S. government, though the degree of complicity remains shrouded in secrecy.

In the 1960s and 70s, the Boston office of the Federal Bureau of Investigation was so desperate to dismantle the city's Italian Mafia syndicates that FBI agents cultivated ties with the city's Irish gangsters, many of whom were eager to squeal on their cross-town rivals.

One of the men recruited was Bulger, who provided the FBI with flimsy tips in return for immunity from prosecution. Despite glaring evidence of Bulger's growing criminal empire, law enforcement officials ignored him. FBI agents felt his value as a gang informant outweighed the damage he was doing to the city.

He had a secondary line of defence against the law as well, lavishing hundreds of thousands of dollars in bribes on law enforcement figures of all stripes.

Bulger's legal exemptions finally expired in 1994, when his closest ally in the FBI, John Connolly, tipped him off that the federal Justice Department had authorized charges against him.

Bulger disappeared for 16 years before agents arrested him in Santa Monica, Calif.

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The subsequent 2013 trial provides the heart of Berlinger's documentary. He interviews several key players in the case – families of Bulger's victims, Bulger lawyers, former FBI agents, prosecutors and a few murderous Bulger accomplices – as the trial progresses. Through it all, Berlinger maintains a neutral journalistic stance, allowing the players to give opinions without taking one of his own.

As final arguments near in the trial, the big question hanging over the proceedings is whether Bulger will testify. Who would he expose? How high would the corruption reach? How complicit was the U.S. government?

In the end, Bulger decided against taking the stand, his potential bombshells destined for the grave. And that's where the documentary sates some of the appetite for a character who has passed into mythic status. The recorded telephone conversation between Bulger and his defence lawyer, Jay Carney, was provided exclusively to Berlinger after the verdict, and the lawyer has said the chances of any future interviews with the 84-year-old convict are unlikely.

Substantively, the interview is unsurprising. Dispersed throughout the film in short clips, it consists mainly of Bulger denying he was ever an FBI informant and pleading ignorance of the agency's 700-page file detailing his interactions with its agents. He had an inverse perspective of the transaction – arguing that he was acquiring information from FBI agents, not the other way around. On the whole, he sounds whiny, old and exhausted.

As evil as Bulger was, his crimes somehow pale alongside the massive government breach of trust that sanctioned his activities for so many years. One government agent, Connolly, went to jail.

The remaining people responsible must be quivering at the recent news that Bulger is busily preparing an appeal. Those bombshells may yet fly.

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Whitey: United States of America v. James Bulger has its international premiere at Hot Docs on Sunday. For more information: hotdocs.ca.

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