Black Mass

Johnny Depp as Whitey Bulger in Black Mass

All images courtesy of Warner Brothers/Cross Creek Pictures

Black Mass

| published October 8, 2015 |

By R. Alan Clanton, Thursday Review editor


In a recent interview in Wired magazine, writer/director Aaron Sorkin tells readers of some advice he got from director/producer/writer Mike Nichols: when it comes to non-fiction, fact-based films, art isn’t about what happened.

An apt quote for Sorkin, since one complaint about his soon-to-be-released Steve Jobs biopic of the same name is that the movie plays it fast and loose with the truth, in most cases due to compressing vast tracts of time into backstage moments in advance of a new product. Since biographical pictures, fact-based films, and the always-fun business of “movies based on real-life history” are back in vogue this year, with a vengeance, this mantra that art isn’t about what happened seems crucial to our understanding, going into these movies, about the stuff we are about to see.

But when it comes to the great American fascination with films about the mob, dabbling with the facts is generally not necessary since it is usually worse than you think. This is often the result of the inescapable laws and canons crafted by Francis Ford Coppola with his classics, The Godfather and The Godfather Part II—films which recrafted, more or less forever, how movies about gangsters are written and produced. But it is also the result of other directors, including Martin Scorcese (Goodfellas) and Mike Newell (Donnie Brasco), both of whom directed films based on books about the real world of organized crime (author Nicholas Pileggi; FBI undercover agent Joe Pistone, respectively). Goodfellas follows the careers of Jimmy Conway (aka Jimmy Burke; aka Jimmy the Gent) and Henry Hill, two non-Italian associates of the Lucchese crime organization. Though writer Pileggi and director Scorcese take a lot of liberties with the story, the underlying facts of Burke and Hill remain largely accurate—or at least as accurate as one can be when it comes to the heavily shaded world of the mob.

Black Mass, based on the book by Boston Globe investigative reporters Dick Lehr and Gerard O’Neill, tells the gritty, often gruesome story of James “Whitey” Bulger, the notorious head of the so-called Winter Hill Gang of South Boston, a leading organized crime faction which eventually became the predominant criminal force in Boston and far beyond. Though the film is anchored largely in the work of journalists Lehr and O’Neill, it also owes something to a half dozen of major books recently published on the subject, including Howie Carr’s The Brothers Bulger: How They Terrorized and Corrupted Boston For a Quarter Century, and Kevin Cullen and Shelley Murphy's Whitey Bulger: America’s Most Wanted Gangster & the Manhunt That Brought Him to Justice.

The attraction for both readers and filmgoers to American organized crime is nearly limitless. There are literally thousands of books on the topic and more than 300 major fact-based motion pictures on the subject of the Mafia and American organized crime. Many tell the stories in a straightforward if not sanitized way, while some play it fast and loose with the truth, and still others are forced by default into the realm of conjecture. Goodfellas, while deeply fact-based, nevertheless must take great liberties to make its decades-long story coherent to audiences; the same can be said of Scorcese’s follow-up film, Casino, which tells of the mob’s deep and nearly inextricable interest in gambling in Las Vegas—one of the Mafia’s richest sources of income for years, but which hubris and stupidity eventually trumped common sense, forcing most of the crime out and essentially allowing Vegas to reinvent itself as a family-oriented tourist destination.

That Whitey Bulger operated his criminal empire for so long—across a wide stanch of time and despite vast law enforcement efforts to break the back of the mob—is at the heart of his anachronistic staying power. Black Mass concentrates its unflinching lens of that aspect of Bulger’s story: his ability to operate with impunity for decades even as other mob and Mafia organizations had long been extinguished or fragmented.

There are two parallel factors in Bulger’s success: his brother, a renowned and longtime political chief and legislative hack who was a kingpin in Boston and Massachusetts politics for decades. William “Billy” Bulger was the president of the State Senate, and later president of the university system in the Bay State. Something of an anomaly himself, Billy was an electoral street survivor who essentially ran the backside of politics in the state, often outflanking nationally known political figures ranging from Ted Kennedy to Michael Dukakis, from William Weld to Paul Tsongas. Billy Bulger was the chief facilitator of nearly everything that happened in Boston in those days, and that included arranging things neatly but quietly for his older brother, Jimmy.

Whitey’s other advantage was decisive, and outweighed strategically even any backroom assistance that came from his brother, the politician. Whitey had friends inside the FBI. It was this unholy arrangement which would eventually cause the FBI its greatest twentieth century embarrassment, and it is this subject which Black Mass explores most closely.
Johnny Depp as Whitey Bulger in Black Mass
Though the full story is both complex and baroque, the short version is this: a childhood pal of Billy and Whitey Bulger, John Connolly (who grew up on the same mean streets of South Boston), would reconnect in 1974 with the mobster. Connolly was then a young FBI agent. Under pressure to rid Boston of the Mafia—primarily Italian and Sicilian operations to some extent beholden to other crime organizations in New York—Connolly and fellow agent John Morris propose to mid-level street hoodlum Whitey Bulger that he become an informant to the FBI. Bulger balks at the suggestion…at first. But soon he warms to the idea as he quickly realizes that the FBI, desperate and hungry for success—any measurable and newsworthy activity—could be manipulated into becoming an unwitting ally in his own ambitions to become the big fish in Boston crime. Bulger and Connolly agree to repudiate the word “informant,” rechristening their arrangement as an “alliance,” one which will become strategically important for both parties, but profitable in the extreme for Bulger.

Bulger will provide modestly useful tips about the Mafia, and in exchange the FBI will begin to systematically look the other way as Whitey slowly begins to consolidate power. Soon, the FBI can take credit for systematically breaking the back of the Mafia in Boston. Even the credulous FBI supervisors in the Boston field office eventually come on board as the newspaper headlines begin to produce a positive result for the Bureau. In time, other agents come on board with the scam, many of them accepting bribes ranging from cash to lucrative private sector jobs with companies under the control of the mob or beholden to the politically powerful Billy. Connolly and other agents become local and regional folk heroes as they get photographed arresting dozens of Italian mobsters.

Still, some in the FBI are quietly suspicious of Connolly’s dangerous arrangement with the Bulger Brothers. Over time, Whitey goes about the grim and often gruesome business of eliminating his competitors or those just in the way. When it is easier and more convenient, he simply provides a few tips to the Bureau, and arrests are made. Witnesses who walk in and provide information damaging to Bulger often turn up dead days later, only after agents Connolly and Morris dismiss their tips as garbage. Despite these red flags, the corruption within the FBI office grows deeper.

With each arrest, with each murder, Whitey’s empire grows—including eventual control over all shakedown rackets, vending machines, pinball machine cash, cocaine revenue, and soon enough, his most lucrative adventure, skimming the cash from huge Jai Alai fronton operations in South Florida and Connecticut. The Jai Alai business, already rank with corruption and cheating for decades, turns violent under Whitey’s unofficial stewardship, and leads to a series of grisly murders in the late 1970s and early 1980s, including the infamous torture-killing of Peggy Westcoat in her Miami home, and the broad-daylight shooting of fronton owner Roger Wheeler in Tulsa, Oklahoma. Wheeler’s murder becomes a tipping point for the FBI in Washington, which begins to try to understand while Bulger’s empire continues to grow despite vast law enforcement efforts to make even a dent in the Winter Hill Gang’s operations.

At stake is nothing less than the reputation of the FBI, the nation’s seemingly unimpeachable law enforcement agency. At the core of Whitey’s unimpeded rise to absolute power in Boston’s increasingly violent underworld is a key conduit of information through which flows everything Whitey needs to stay ahead of problems—the names of informants, the names of real or potential rivals, even the timing of police raids by Boston and State cops. Agent Connolly becomes, in essence, Bulger’s informant within the FBI. This lopsided quid pro quo eventually runs amok, and leads to the FBI’s complicity in, or acquiescence in, an increase in drug trafficking and shakedown activity, more violent murders, and even the murders of several key FBI witnesses.

Then, when others inside the FBI begin to look more closely at the Connolly’s paper trail—and all those immeasurably valuable “tips” and “leads” provided by Whitey—they discover prevarication and outright subterfuge: Connolly has been merely using other’s testimony and other’s tips, and substituting Whitey’s name as the “secret” source. Connolly, as it turns out, has been little more than a mole working for the mob. When the scam unravels, Whitey must pack up suitcases filled with cash and flee Boston forever; he remained on the lam for more than a decade before the FBI located him, in the summer of 2011, hiding in “retirement” in a quiet condominium in Santa Monica, California.

For a period of several years, Whitey remained high upon the FBI’s list of the most-wanted fugitives from justice. Connolly and other FBI agents were later indicted on corruption charges and ended up in prison, consigned to special units out of reach of the general prison population. Bulger was eventually convicted of multiple murders, money laundering, extortion, robbery, drug trafficking, weapons charges, and racketeering.

Johnny Depp is cast in the role of Whitey—a excellent casting decision save for the eyes: Depp’s dark brown eyes must match Bulger’s famously cold, steely ice blue, and the contacts worn by Depp heighten the sense that the calculating psychopath we are watching verges on something close to non-human, an eerie taunt to moviegoers which director Scott Cooper may have intended.

A warning to anyone who wants to see this film: the violence is extreme in some places, even more so than aficionados of mob movies may find comfortable. Again, this is certainly deliberate: Whitey Bulger’s world was gritty and tough, and those loyalists around him were accustomed to enforcing discipline in the rawest, most bloody means possible. The primarily Irish South Boston where Whitey and Billy grew up was not for the meek or the faint-of-heart, and it was not a neighborhood for bluebloods. Kids sorted out their differences with extreme violence, and those who remained in the neighborhood carried that flintiness with them into adulthood. Black Mass translates this brutal world quite effectively to the big screen.

In addition to Depp’s icy, chilling performance, the rest of the cast works seamlessly, with Benedict Cumberbatch as Billy Bulger, Joel Edgerton as FBI agent John Connolly, Kevin Bacon as FBI agent Charles McGuire, Rory Cochrane as Whitey’s longtime top lieutenant Steven Flemmi, and David Harbour as FBI agent John Morris. Morris will be the agent who eventually contacts reporters for the Boston Globe to reveal the depth of the corruption within the Boston’s FBI office. Jesse Plemons plays the role of Kevin Weeks, a driver and street muscle guy working for Whitey, who himself turns state’s evidence and cooperates when the poop hits the fan. (Weeks is the co-author of a book revealing his participation in the Winter Hill gang’s criminal activities in the 1970s and 80s).

One important sidebar issue which cannot be overlooked when reviewing this film (and it takes us full circle back to Martin Scorcese’s directorial skill when it comes to organized crime movies): for anyone who has seen Scorcese’s 2006 fictional film The Departed, much contained in Black Mass will seem oddly familiar, even at times like déjà vu. That’s because the story for The Departed, which stars Leonardo DiCaprio, Matt Damon, Martin Sheen and Jack Nicholson, was written as a loose homage to the famous Whitey Bulger criminal empire (by then already defunct, with Bulger in hiding), and his control over key corrupt FBI agents and police in Boston. Nicholson plays a Bulger-like Irish mobster, Damon plays a Connolly-like mole within the state police, and so on. Scorcese fictionalized his story, and rebooted it into a higher tech, more contemporary version—but make no mistake that the “any resemblance to persons real or living” clause in the final credits is a feigned concern for the boilerplate legal issues, and an ironic nod to the fact that Bulger was alive and on the lam.

Black Mass is highly watchable and revealing, but clearly not for all audiences. Aside from the predictable language, the violence is—at times—intense and visceral. That Bulger and Flemmi were known to employ extreme violence is now well-documented in those dozens of books and investigative works. What is not as generally known is that Bulger had a particularly high taste for intense violence which verged on sadistic and psychotic, the result—he intimates in some of his diaries and his letters—of being asked to “volunteer” for LSD experiments during his first long stretch (1956 to 1965) in some of the hardest federal prisons at the time—Leavenworth, Atlanta, and Alcatraz. Bulger was one of the last criminals sent to Alcatraz; only a hundred or so are listed in the rolls after his arrival there in the 1960s.

While serving time in Atlanta, Bulger was one of several dozen who negotiated early releases in exchange for the psychotropic drug testing, which doctors at the time thought might be useful in treating schizophrenia. Bulger called the experiments nightmarish, confiding to friends and associates that the after-effects of the high doses of LSD were with him forever, and would surely play a part in his ill-tempered forms of criminal violence. Depp captures this uneasy, barely checked sadism with chilling skill, and shows us a crime boss all-too-willing to let his business decisions become clouded by unhinged episodes of cruelty.
Johnny Depp as Whitey Bulger in Black Mass
The film moves quickly, and comes in at two hours and two minutes. The only disappointment for me was that I wanted more historical context, and a better understanding of how a major FBI office slipped so easily into corruption. In his book, Howie Carr suggests that too many of the top politicians in Boston and Massachusetts chose for too long to simply look the other way as the Bulgers systematically corrupted the democratic processes. Among those political figures who rose to power while the Bulgers controlled Boston are Michael Dukakis, John Kerry, William Weld, Paul Tsongas, and a half dozen Kennedys. Carr and other writers suggest that the unofficial policy was to simply look the other way—easier to go along and get along than to confront a corrupt system.

In that sense, those who facilited Whitey Bulger's reign of crime, violence and murder were engaged in a slight variation of that filmmakers' canon: it isn't about what happened.

Related Thursday Review articles:

The Martian; R. Alan Clanton; Thursday Review; October 7, 2015.

Pulp Fiction Turns Twenty; R. Alan Clanton; Thursday Review; December 14, 2014.