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The FBI’s Homemade Mobster

A ghoulish Johnny Depp channels Whitey Bulger's malice in a story of literal "gangster government."
Johnny depp black mass gangster

Looking back at the last couple of hundred years of European history—on paper at least—you wouldn’t expect Italians, of all peoples, to have a major advantage over the Irish in terms of organizational acumen or systematic brutality. And yet, when it comes to organized crime in 20th-century America, the Mafia ran the table on the Irish mob, driving them all but out of business by the end of Prohibition.

Gangland historian T.J. English tells the tale in Paddy Whacked: The Untold Story of the Irish-American Gangster—a book the feds found on James “Whitey” Bulger’s shelves in his Santa Monica hideout in 2011, when they finally captured the last Irish Godfather after his 16 years on the lam. “Over the three-year period from 1931 to 1933,” English writes, “virtually every high-ranking Irish American bootlegger in the Northeastern United States was systematically eliminated, gangland-style.” As they went up against the wall, the great American genre of the mob movie was just being born, in films like “Public Enemy” and “Angels with Dirty Faces.” “The irony, of course,” English observes, is that “just as Jimmy Cagney emerged as the avatar of a new kind of street-wise Irish American style, the mobsters who inspired that style were dropping at an expeditious rate.” By the late 20th century, the old-school variety survived only in a few ethnic enclaves, like New York’s Hell’s Kitchen, or Boston’s Southie.

Adding insult to injury, the Mafia beat the Irish clans twice: once in the Prohibition-era turf wars over black markets, and again, more lastingly, in the American imagination. “The Godfather,” “Goodfellas,” and “The Sopranos” loom large; except for the occasional gem like 1973’s “Friends of Eddie Coyle,” the Irish Mob can’t catch a cinematic break.

That’s not for lack of rich material. The Whitey Bulger story is the most lurid, noirishly fascinating tale in mob history, one in which it’s hard to tell the gangsters from the G-men. The basic facts have been known since at least 1999, when, after 10 months of hearings, Massachusetts federal judge Mark Wolf issued a mammoth, 661-page opinion outlining the devil’s bargain between the Boston FBI and its “Top Echelon Informants” Bulger and Stephen “the Rifleman” Flemmi.

But “Black Mass,” which opened last weekend, is the first big-screen attempt to tell the story straight. You can hardly count Martin Scorsese’s criminally overrated “The Departed,” a bloated, Hollywood star vehicle that’s as phony as a Shamrock Shake. The Southie mob boss of “The Departed,” played in scenery-chewing, self-parodic fashion by Jack Nicholson, is clearly based on Whitey, though for some reason the Bulger character takes his name from an actual Italian mobster, “Frank Costello,” né Francesco Castiglia, who adopted an Irish surname.

In “Goodfellas,” Scorsese stuck close to his source material, the life of New York mob associate Henry Hill, to eke high drama out of lowlife hoods. In the “The Departed,” he mashed up the Bulger case with the sensationalist plot of the Hong Kong crime thriller “Infernal Affairs.” The result was as ridiculous as “Goodfellas” was realistic.

Unlike Costello in “The Departed,” the real Whitey Bulger didn’t sell missile parts to the Chinese. Whitey made his money by shaking down bookies and drug dealers—and, in one weird episode briefly depicted in “Black Mass”—“winning” the Massachusetts state lottery. “After a winning ticket was sold at his Rotary Variety Store,” Boston Globe reporters Dick Lehr and Gerard O’Neill explain in their 2000 book Black Mass: the True Story of an Unholy Alliance between the FBI and the Irish Mob, “Bulger informed the $14.3 million jackpot winner that it would be in his best interests to acquire a new partner.”

And unlike Costello, the real Whitey Bulger didn’t have scads of double agents and on-call assassins honeycombed throughout state and federal law enforcement, ready to kill other cops on command. He had two FBI agents in his pocket, most of the Boston FBI office criminally compromised, and a brother, Billy, who was president of the state senate and one of the most powerful figures in Massachusetts politics. That was more than enough.

“Black Mass,” based on Lehr and O’Neill’s book, sticks much closer to reality. There’s far too much in the underlying story to fit into a film that runs just over two hours. So, the fair questions to ask are: (1) Is the movie good? And (2) is it reasonably accurate? On both counts, the answer is a qualified yes.

Humanizing Whitey?

It’s a qualified yes on the first count because “Black Mass” has problems, starting with the casting. The great mob dramas take pains to put the viewer in an actual time and place; The “Sopranos” bolstered its authenticity by picking actual Bridge and Tunnel Italians to play North Jersey mobsters. And the “Godfather” would have been a very different movie with—as Francis Ford Coppola apparently contemplated—Laurence Olivier as Don Corleone and Dustin Hoffman or Martin Sheen as Michael.

So you have to wonder, did Scott Cooper hang a “No Irish Need Apply” sign outside the “Black Mass” casting call? The leading roles went mainly to actors who’d qualify only under St. Patrick’s Day rules. In Jesse Plemons from “Breaking Bad”, they actually got a guy who’s uglier than Kevin Weeks to play the feared Bulger crew enforcer, and Plemons can’t even fake-punch convincingly. Benedict Cumberbatch, who plays Billy Bulger, is practically British royalty. Come on!

What’s more, if you want to clue the viewer into the fact that it’s Boston in the 1980s, there have to be subtler ways to go about it than having a character say, “hey, Wade Boggs is hitting pretty good.” Too much of the dialogue comes from the “tell, don’t show” school of screenwriting, as in the early exchange between Billy and Connolly: “Look at you, big FBI agent now”; Connolly: “Yeah, but I haven’t forgotten where I come from!” Later on, Billy and Connolly reminisce about working on the state senator’s first campaign, with Billy waxing melancholy: “Oh Jesus, we were just kids, now look at us.” Real people don’t talk like this.

And yet, somehow, the whole thing works. For all its faults, the film gets a lot of things right, principally the Bulger-Connolly relationship. Whitey’s chief enabler in the Boston FBI grew up around the corner from the much-admired local tough, and seems never to have lost the toxic man-crush he developed on Whitey as a kid. The Australian Joel Edgerton does an admirable job as the insecure, blustery Connolly, and Depp is nearly perfect as Whitey.

The director, Scott Cooper, has said that he wanted “to humanize Whitey Bulger,” a bizarre aspiration when you’re talking about a guy who strangled young women with his bare hands. Stranger still is Cooper’s search for what he’s called Bulger’s “tender and humorous side.” The evidence that Whitey ever had a sense of humor is sparse. The “jokes” he told were the sort designed to provoke nervous laughter. Weeks and Flemmi both testified that when they passed Tenean Beach, where Bulger had buried mob rival Paul McGonagle, Bulger liked to crack, “Drink up Paulie, the tide’s coming in.” His idea of ribbing a pal was to nickname Flemmi “Dr. Mengele,” because Flemmi “kind of enjoyed” pulling victims’ teeth out with pliers so their bodies couldn’t be identified from dental records.

Luckily, Cooper’s intentions were utterly undone by Johnny Depp’s ghoulish performance. From a distance, with his popped-collar leather jacket, Depp-as-Bulger looks a bit fey, and ’80s New Wave. In every close camera shot, however, Depp radiates menace. Throughout, he conveys what Bulger biographers Kevin Cullen and Shelley Murphy called the gangster’s “strange and complex amalgam of the depraved and the blandly conventional.” Why try to “humanize”? Sociopaths can be fascinating.

“This Thing of Ours”

If anything, though, “Black Mass” is too soft on the FBI. Bulger “was a small time player” Plemons’ Weeks says in the movie, “the next thing you know, he’s a damn kingpin. You know why? Because the FBI let it happen.” The verb is wrong: the FBI made it happen.

As Judge Wolf noted in 1999, “at the urging of Attorney General Robert Kennedy, in the mid-1960’s a previously reluctant FBI became committed to combatting the LCN. FBI Special Agent H. Paul Rico recruited Flemmi to serve as an asset in that effort.“ Moreover, “the FBI played a pivotal role in forging a formidable, enduring partnership between Flemmi and Bulger, who had in 1975 also become an FBI informant. The FBI made Bulger and Flemmi, who were previously acquainted but not close, a perfect match.” From 1975 to 1990, in its quest to bring down the Italian mob, the Bureau became partner in crime to Bulger and Flemmi’s Winter Hill gang, frustrating state police and DEA investigations of the crew, and tipping them off to potential informants, who were promptly killed. Nor was the FBI’s corruption limited to “a few ‘bad apples,’” Wolf identified more than a dozen FBI officials who broke the law in attempts to protect their “assets.” It’s telling that when Flemmi was finally arrested in early 1995, a Boston FBI agent told him, apologetically, “This thing of ours, it is no more.”

The great libertarian economist Murray Rothbard was a fan of the mob-movie genre. But for my money, the craziest thing he ever wrote was his 1990 review of Goodfellas, which he condemned on ideological grounds for failing to romanticize the Mafia as an alternative to the state. “Organized crime is essentially anarcho-capitalist,” Rothbard explained, “a productive industry struggling to govern itself; apart from attempts to monopolize and injure competitors, it is productive and non-aggressive.”

“Goodfellas,” with its depiction of mobsters as “psychotic punks,” was “repellent and loathsome,” he charged. In contrast, “Godfather” I and II “were perfection,” because they recognized “that the Mafia, although leading a life outside the law, is, at its best, simply entrepreneurs and businessmen supplying the consumers with goods and services of which they have been unaccountably deprived by a Puritan WASP culture.”

But of the two, “Goodfellas” was the true-crime story, and the “Godfather” was the fairy tale. The grisly genuine article is tougher to romanticize. But if you want to draw libertarian lessons from a mob movie, you could do worse than “Black Mass,” which shows that “gangster government” isn’t just a metaphor.

The Irish immigrants who pioneered organized crime in America were never as organized as their successors, one reason why they lost. In another sense, though, they departed the field, having recognized early on that the biggest gang going was the government. By the 1960s, the term “Irish Mafia” had a somewhat different connotation. From the cops, to the city council, to the federal government, the upwardly mobile Irish went “legit.”

Maybe that’s what Whitey was getting at earlier this year in his handwritten reply to three high-school girls who wrote to him for a history project. “Advice is a cheap commodity,” Bulger wrote from his cell in Sumpterville, Florida, “some seek it from me about crime—I know only thing for sure—If you want to make crime pay—‘Go to Law School.’”

Gene Healy is a vice president at the Cato Institute and author of The Cult of the Presidency.