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Home Movies: Who’s the Bigger Criminal, Whitey Bulger or the FBI?

Whitey
Mugshot of James "Whitey" Bulger. Alcatraz Federal Penitentiary. Magnolia Pictures

Joe Berlinger's fascinating true-crime film suggests that the legendary crime boss may not be the most corrupt guy in Boston

In the Irish-American neighborhood of South Boston, parents wanted their children to excel. Kevin Weeks, whose brothers both went to Harvard, matriculated instead into organized crime. Weeks recalls that, as he prepared to commit his first murder, he promised himself, “I’m gonna be the best at it that I can.”

Whitey Bulger’s younger brother Billy was, as one journalist notes, “the most powerful politician in Massachusetts”: he ran the state Senate from 1978 to 1996, then served seven years as the President of the University of Massachusetts. Whitey served in juvenile jail, the Atlanta Penitentiary, Lewisburg and Alcatraz. Back home in the mid-’60s, he took over the Winter Hill Gang and, with Weeks as his enforcer, became the most famous and feared gangster in New England. Before Bulger was arrested with his girlfriend Catherine Greif in Santa Monica on Jun. 22, 2011, having lived on the lam for 15½ years, he ranked No. 2 on the FBI’s Most Wanted list, just behind Osama bin Laden. As America’s top homegrown criminal, the kid from Southie had made it big.

How did Bulger run the Boston mob so long and with such impunity? (As his defense attorney Hank Brennan says, “He was never charged with even a misdemeanor.”) And how did he manage to elude the law when he went into hiding? Joe Berlinger’s engrossing documentary Whitey: The United States of America v. James J. Bulger, argues that he was shielded from prosecution by John J. Connolly, Jr., Bulger’s FBI contact and an old Southie pal, and federal prosecutor Jeremiah T. O’Sullivan — perhaps in exchange for inside information, perhaps not. Either way, the government enabled him. The film’s subtitle could be The United States of America in cahoots with James J. Bulger.

Whichever side you take, Whitey is a must-see. On VOD, where the film is widely available, viewers can savor each betrayal, replay the enormity of Bulger’s (and perhaps the FBI’s) crimes and study the eloquent pain of the victims. Sticking to the facts, this documentary is still a much movie-r movie than, say, Martin Scorsese’s Oscar-winning The Departed, starring Jack Nicholson as a fictionalized Bulger, or other Boston-based dramas like Mystic River and The Town, with famous actors doing their darnedest to mimic the distinctive Southie accent. (Next year we’ll see an official Bulger bio-pic, Black Mass, with Johnny Depp as Whitey and Benedict Cumberbatch as his brother Billy.) There’s truth, not art, in the handsome, meaty faces and broad vowels of the men and women Berlinger interviewed. The tears these tough people shed come not from the Method but from memories of what the ogre did to them and their loved ones.

(READ: Corliss’s review of The Departed)

For Bulger returned to Boston like a dreaded ghost from the bedroom closet of a child’s nightmares. One difference: this scary figure left lasting scars on the victims and their families. Stephen Rakes recalls Bulger and Weeks visiting him in the ’70s, shortly after he opened the South Boston Liquor Mart; they dropped by to convince him to accept the mob as partners. If he didn’t, Whitey said, “I’ll stab ya and I’ll kill ya.” When Rakes declined the proposal, Bulger looked at the man’s year-old daughter and noted, “It’d be terrible for this kid to grow up without a father.” Rakes says he was never the same, but is now eager to testify against Bulger: “Thirty years ago he scared me to death. He don’t scare me to death no more.”

Rakes’ partner in grief is Steve Davis; he believes Whitey killed his sister Debbie, who had been a girl friend of Bulger hit man Steve Flemmi. (You need a scorecard to sort out all the Steves, Debbies and John J.’s in this movie.) “Steve and I,” says Davis, referring to Rakes, “we have something in common: this psychotic individual. We’re gonna bring justice. It has to be done” — as if they are the villagers who consider it their solemn duty to take communal revenge on the monster. Yet later, after Rakes is taken off the witness list, he is found dead seven miles from where his car was abandoned. He seems to have been the victim of a business dispute that had no connection with the Bulger case.

Weeks (who in Black Mass will be played by Jesse Piemons) has the roguish bravado of an insider who can rationalize crimes against anyone: the feds, or civilians caught in the crossfire, or his old boss. Of FBI agents, he says, “They have a badge that [identifies them as a] Special Agent. But there’s nothin’ special about them. They’re regular people. If you find their weakness, or their needs, or if they have a problem and you can solve it for them, you can corrupt them” — with payoffs of between $25,000 and $50,000 per transaction. He shrugs off the death of Michael Donahue, whose crime was to have shared a ride with one of Whitey’s enemies. Rules of the game, says Weeks: “You wanna spend time with gangsters and wise guys, this is what happens.” A serial perjurer who admits, “I’ve been lyin’ all my life,” Weeks defends his decision to inform on Whitey: “You can’t rat on a rat.”

Berlinger, who spent nearly 20 years on his Paradise Lost trilogy documenting the unjust convictions of the West Memphis Three, lets Bulger’s lawyers lay out the defense: that, yes, Whitey was involved in drug-dealing, bookmaking and loan-sharking but, no, not murder. He says Weeks, Flemmi and John Martorano committed the crimes, then turned informants to get shorter sentences. At issue in his trial, as Bulger saw it, was not his freedom — 83 when the trial convened, he knew he would spent the rest of his life as a guest of the state — but his legacy. On the phone with defense attorney J.W. Carney, he stoutly avers, “I never, never, never cracked [informed].” Says Fred Wyshak of the prosecution team, “He doesn’t want to be called an informant. Because where he came from, in Southie, that’s the worst thing you can be.”

(READ: Joe Berlinger on the West Memphis Three)

That, and a literal lady-killer. Bulger also strenuously denies the charges that he strangled Deborah Hussey and Steve Davis’s sister Debbie. “Whitey Bulger cannot have people think he murdered those two women,” says Kevin Cullen, a Boston Globe columnist who coauthored two books on Bulger. “And he cannot have people think he was an informant. This is not about getting acquitted. This is about changing the narrative back to the one he spent years cultivating. And that narrative is he is a good bad guy. He is a gangster with scruples; he is a criminal with standards. And gangsters with scruples do not murder women and bury them in shallow graves. Criminals with standards don’t turn on their friends.”

“Criminals with standards” are still criminals, while the feds are supposed to be the good guys. Yet long-time Boston journalists insist the FBI protected Whitey in exchange for information on the local Mafia. Connolly and his fellow agent John Morris, as well as federal prosecutor O’Sullivan, are said to have let the Bulger gang run unfettered for decades. One unsullied agent, Bob Fitzpatrick, who tried to bring the mob boss to justice and was determined to testify to the unholy alliance between Bulger and the feds, is treated nearly as a hostile witness by the prosecution. “I think the FBI is worse than the Mafia,” says Michael Donahue’s surviving son Tommy. “They’re the most organized crime family on the planet.”

“The real story here is that our government enabled killers to run free in this city,” says David Boeri, senior reporter for WBUR radio and a consultant on the film. So compromised was the FBI, Boeri claims, that it became “the Bulger Bureau of Investigation. And it was because they [the feds] were all crazed about getting the Mafia that they enabled the Irish godfather to run the show here. And he was far more dangerous than the Italians.” In the end, Weeks and his lieutenants wore out their loyalty to Whitey and agreed to help bring him down. As Steve Davis notes, “The Irish mob, every one of them, they were stumbling over each other, just to rat.”

One thing Boston mobsters and their victims have in common: they love to talk. The charm and blarney, the threats and alibis, form a spectacular symphony of verbal belligerence, which Berlinger listens to and sorts out for viewers. The director gives more screen time to the defense than to the prosecution, perhaps because he buys their assertion about government corruption, perhaps because they’re just better bullshitters. At the end, though, we learn that “The FBI declined to be interviewed for this film.” In this complex weave of Southie malfeasance, the Agency’s silence may be its own indictment.

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