The Long Arm of Whitey Bulger - Pacific Standard

The Long Arm of Whitey Bulger

A compelling new documentary on Boston's infamous mob boss shows the lasting trauma of his reign of terror.
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The apartment building in Santa Monica, California, where Bulger lived as a fugitive for at least 15 years. (Photo: Shirtwaist/Wikimedia Commons)

The apartment building in Santa Monica, California, where Bulger lived as a fugitive for at least 15 years. (Photo: Shirtwaist/Wikimedia Commons)

The Departed it ain’t. The new documentary Whitey: United States of America v. James J. Bulger about last year’s trial of one of the most notorious mob bosses in American history, has its share of twists and turns, but it does nothing to glamorize this story of organized crime and terror in Boston. It’s dark, and it’s damning, and next to no one comes out looking good.

James “Whitey” Bulger and his Winter Hill Gang ruled South Boston during the 1970s, '80s, and early '90s—gambling, stealing, extorting, and, when someone got in their way, killing. Close ties with the FBI in Boston kept Bulger from ever being charged with any crime until the mid-1990s, and even then an agent tipped him off before he could be arrested. Bulger was on the lam for 16 years before he was finally found, appearing just below Osama bin Laden on the FBI’s “Most Wanted” list. After a dramatic trial last year, he was found guilty of racketeering and 11 out of the 19 murders he had been charged with.

This documentary, which examines the nature of those FBI ties, uses an impressive range of archival materials to tell the story. It features crime scene photos, old police surveillance video of Winter Hill Gang meetings, news reports, and even an FBI video from the 1980s about how to use informants that features Bulger’s own handler, John Connolly. It interviews Bulger’s right-hand-man-turned-government-witness Kevin Weeks, who describes the gruesome murders of the gang’s girlfriends who “knew too much” as matter-of-factly as a trip to the grocery store.

"It’s been 30 years of torment, and now it’s coming to an end, thank God. My father always told me that ‘Good will always triumph over evil, even if it takes a long time,’ and that’s what I’m here for."

Cameras weren’t allowed in the courtroom during Bulger’s trial, but still shots and voice-overs of the transcripts do the trick. And for the first time since Bulger refused to testify at his trial, we hear his voice. In taped phone calls with his defense attorney from prison, we hear him sounding pissed off, tired, aggrieved.

During Bulger’s trial, his defense team spent all its time and energy on arguing that Bulger was not, as the accepted narrative goes, an informant for the FBI. They explained that the reason authorities seemed to give his group a pass while they aggressively pursued other mafia families was that they themselves were corrupt. At the time, the authorities were under political pressure to go after the bigger-name Italian mafia families, and when they did, the Winter Hill Gang stepped into the vacuum.

Bulger has maintained that he didn’t get protection from the FBI; rather, he bought them when they were for sale. (As Bulger put it, “We pay; we don’t say.”) In exchange for cash, jewelry, and cases of wine, the defense argued, the FBI would give Bulger information about other groups—not the other way around. Bulger was not on trial for his relationship with the FBI; he was on trial for racketeering and murder. But everyone knew he was guilty of those. He was intent on shaping his legacy as a “good bad guy,” as one person puts it. And the worst thing anybody in Southie could ever be was a rat.

Most of the film is devoted to the trial and the debate about whether or not Bulger was an informant, and it gets into the weeds of who-said-what-when and who-was-where. The film’s director, Joe Berlinger, who previously put out three feature-length films on one murder trial, could never be accused of skimping on detail.

But the most powerful sections of the film, book-ending the main event, are the interviews with the family members of the victims. Regardless of whether the FBI paid Bulger in protection or Bulger paid the FBI in cash, or both, there’s no denying that he and his associates were ruthless killers. The film is most affecting when it follows the victims’ families as they prepare themselves for Bulger’s trial, when they will finally face him in court, and hope to get some closure.

As they drive to the trial with the filmmakers in their passenger seats, the family members’ adrenaline, anxiety, and relief are palpable. Steve Davis, whose sister Debra Davis was killed, stutters and shakes his head as he drives. “My head’s been so twisted over this,” he says. “It’s like, surreal ... it’s happening.” Patricia Donahue, murder victim Michael Donahue’s widow, says, “Mike was killed 30 years ago, but it seems like yesterday.”

“It’s been 30 years of torment, and now it’s coming to an end, thank God,” says Stephen Rakes—a poignant quote from an extortion victim with an especially tragic tale. “My father always told me that ‘Good will always triumph over evil, even if it takes a long time,’ and that’s what I’m here for.”

The belief that the government was complicit in the murders of their loved ones is what seems to have brought many of these family members the most bitter pain, the most lasting trauma. Tommy Donahue, son of Michael Donahue, tells the filmmakers with wide eyes, “I think they’re the most organized crime family on the planet, who can do whatever they want, and they’re not to be screwed with, to be honest with you—we’ve seen that first hand.” He’s not talking about Bulger’s gang; he’s talking about the FBI, whom he holds directly responsible for his father’s death. “The FBI, they haven’t been on our side since the day they killed my father,” he says.

"I think they’re the most organized crime family on the planet, who can do whatever they want, and they’re not to be screwed with, to be honest with you—we’ve seen that first hand." He’s not talking about Bulger’s gang; he’s talking about the FBI.

One FBI agent in Boston, John Connolly, was convicted in 2008 in relation to a different Winter Hill Gang murder. But no one else has been punished for any misconduct, and the FBI maintains the narrative that Connolly was just one “rogue agent,” and that the corruption was not systemic. (Connolly’s conviction was actually very recently overturned, and his case is ongoing.)

Berlinger has said that he does not want the FBI’s corruption to be the takeaway of the film, but he does give it a lot of air time. A viewer comes away not knowing what the truth is, but feeling pretty cynical about everyone involved. Except, that is, for the victim’s families, and the media who doggedly covered this case for so many years. The film crew spends a lot of time in the public radio studios of Boston’s WBUR, and the film closes with a montage at the newsroom and printing press of the Boston Globe as the print edition declaring Bulger “Guilty” on its front page is going to press.

WBUR reporter David Boeri reflects on the the case in a candid moment with the director. “They empowered these people, who were carrying out terror,” he says, referring to the government’s role. “They gave them the run of the city! That was lawlessness by the government. That is what we can never forget.... And memory is a political act ... you’ve got to keep the memory, even if other people aren’t.”

Whitey premiered at the Sundance Film Festival this January, just a few days after Bulger arrived at the high-security federal prison in Tucson where he still remains incarcerated today. It is coming out in theaters and on iTunes on June 27.

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