Black Mass, directed by Scott Cooper, world premieres at the Venice Film Fest, September 4.
For more than a decade—until his capture in 2011—Boston’s most infamous crime lord, James “Whitey” Bulger, was hunted by the FBI, surpassed only by Osama Bin Laden at the top of the Bureau’s Most Wanted List.
The irony is that Bulger might never have risen to the level of power he achieved were it not for the aid and abetment of the FBI.
Black Mass explores how a deal between ruthless gangster Whitey Bulger and FBI Agent John Connolly enabled Bulger to expand his criminal empire with complete impunity. Connolly—blinded by his own ambition—shielded Bulger from investigation, ignoring the rising body count.
Growing Up in Southie
Director-producer Scott Cooper notes, “John Connolly had known Whitey and his brother, Billy Bulger, since they were kids growing up in the small enclave of South Boston, called ‘Southie.’ This story interested me because of the bond between these two brothers, who could not have been more different, and John Connolly, who understood the power of the Bulger clan and had always revered them. Connolly ultimately allowed Bulger to run amok in the city because he’d wanted to be in Whitey’s good graces ever since Whitey rescued him in a playground fight when they were kids.”
While Connolly was rising through the FBI ranks by taking on the New York Mafia, Whitey Bulger was making a different kind of name for himself back home. As he grew in power, eventually taking over leadership of the local Winter Hill Gang, he was feared by some, but for many others he was a Robin Hood figure who was good to the neighborhood.
Johnny Depp, who portrays James “Whitey” Bulger, expands, “Southie was and is a very close knit neighborhood and they were very loyal to Jimmy,” he says, using the first name by which Bulger preferred to be called. “Many people grew up kind of idolizing him; many wanted to be him because he did things his own way and, for the most part, he won. But he was also a very charismatic man. He had this draw that made people want to get close to him. They wanted to understand him. They wanted to know him. I found James Bulger to be a fascinating character and was interested in what drove him.”
Cast in the role of John Connolly, Joel Edgerton says, “I think John saw Whitey as a kind of renegade who had this rock star glow about him in the community. To him, there was a deeper connection—he knew the rock star and that rock star had treated him well. Once. I believe he went into the FBI with good intentions and had aspirations of being a great lawman. But on his home turf there was a very blurry line between crime and the law, and if the person you admired was on the other side of the law, it could lead to other aspirations. When you look at the seemingly boundless freedom with which criminals operate…I think he started to get a little intoxicated by that.”
Producer John Lesher observes that Connolly’s fascination with Whitey might not be so different from the rest of us. “We know from movies, books and TV that people are intrigued by gangsters; they live by different rules than the rest of society. In this particular case, you have a close tie between a notorious gangster, whose brother happens to be the most powerful politician in the state, and a star FBI agent. You couldn’t make this up; it’s too incredible.”
Lesher acknowledges that the filmmakers did take some creative license in dramatizing the real-life events “because it would be impossible to adequately portray everything that transpired in a single movie. We composited a few characters and compressed the timeline of some things, but the overall story is based on real events, which makes it extremely compelling.”
The explosive revelation that Whitey Bulger had been an informant for the FBI made headlines in The Boston Globe in 1988. Over the next decade, the details of the corruption spilled out. Globe reporters Dick Lehr and Gerard O’Neill, who broke the story, later laid out the entire story in their book Black Mass: Whitey Bulger, the FBI, and a Devil’s Deal, upon which the movie is based.
Initially, however, they’d had a completely different slant to their article. Lehr discloses, “It was originally going to be a tale of two brothers: Whitey and Billy, who grew up in the same house in the South Boston projects and ended up at the top of their respective games, albeit with very different rules.”
Billy Bulger’s game was politics. College educated, his career trajectory was the polar opposite of his criminal brother’s, taking him all the way to the presidency of the Massachusetts State Senate.
Benedict Cumberbatch, who plays the role of Billy, concurs that the dichotomy between the two brothers was an intriguing angle to pursue. “Billy Bulger was a very powerful political figure for many years in the State Senate. If you wanted anything done, you went through him. And then, on the other hand, he’s the brother of Whitey Bulger and is fatefully entwined with quite possibly the most infamous criminal of the 20th century. It’s a fascinating divide.”
Depp agrees. “Billy went his way and became this very highfalutin’ politician, and Jimmy went his way and ended up a king of the underworld. Yet they visited their mom and were a close family even though they were on distinctly different sides.”
The exploration of the brothers’ remarkably divergent paths was going to be the crux of the article–until the journalists uncovered a stunning twist. Lehr explains, “We discovered that even though Whitey was an acknowledged crime boss, he had somehow eluded the authorities with a kind of magical touch. As we started to peel the layers of the onion, we found that, within local law enforcement, it was long suspected something funny was going on between Whitey and the FBI—namely an agent named John Connolly, also from South Boston.”
“Once we were able to establish that Whitey was an FBI informant, we let the genie out of the bottle,” O’Neill says. “Informants are the Holy Grail of the FBI and, in turn, the ‘wise guys’ want a friend in law enforcement, so it’s a symbiotic relationship. But I don’t think Whitey Bulger would have been an informant for anyone who wasn’t from Southie. Connolly having grown up in that neighborhood made them simpatico in a way no other agent could be. Connolly was able to use his hometown connection and was recognized and rewarded for having Whitey as an informant, but it was Whitey who was in control.”
“At first,” Lehr continues, “it was hard to believe that Whitey was informing for the FBI because it went against everything he stood for. We did corroborate and confirm it and published what turned out to be just the tip of the iceberg.”
“And boom…the fuse was lit,” O’Neill interjects.
“We didn’t know how deep and dark and horrifying it was; that took years to tumble out,” says Lehr. “But the story opened the door to what later became this epic saga and the historic scandal involving Whitey and the FBI.”
Producer Brian Oliver, who originally optioned Lehr and O’Neill’s book, notes, “What interested me was the notion that the FBI would have high level mob people working for the Bureau—or the FBI thinking they’re working for them. It shows anybody can get sucked down the rabbit hole. Connolly probably thought he was doing the right thing until he knew he was doing the wrong thing, but there was no going back.”
The screenplay for “Black Mass” was written by Mark Mallouk and Jez Butterworth, who each saw how the neighborhood ties that bound Connolly and Bulger formed a knot that couldn’t be undone. Mallouk says, “It’s about how ambition erased the better part of the good works Connolly achieved when he started out in the FBI. He wanted to save Boston from the Italian mob; that was his intention when he put his toe in the pool and started helping Whitey. He thought it would be a mutually beneficial relationship. But there is no putting your toe in the pool with someone like Whitey Bulger. You’re underwater right away.”
“It becomes a case of the tail wagging the dog,” adds Butterworth. “This force Connolly was hoping to harness on behalf of the FBI ends up the other way around, with Whitey holding the reins. Anyone who wasn’t so embroiled with Bulger would probably have recognized what was happening, but for some reason Connolly didn’t.”
Scott Cooper reveals that the unique dynamic between the characters was largely what intrigued him about the script. “I tend to be drawn to the deeply tragic and the deeply human and this film offered up both. It’s almost Shakespearean in nature and dealt with themes I like to explore: corruption, deceit and hubris, all wrapped into a narrative I felt it would be very interesting to mine.”
There are also the contrasting—and sometimes conflicting—portraits of family: the family to which you are born, personified in Whitey and Billy, and the family born of the streets, seen through Connolly and Whitey and also through Whitey and the Winter Hill Gang. “I think James Bulger ran his crew like a family and looked at those people as his real family,” says Depp.
Another aspect of family is the one you choose, depicted in the relationships between Whitey and his former girlfriend, Lindsey Cyr, played by Dakota Johnson, and Connolly and his wife, Marianne, played by Julianne Nicholson. “Lindsey and Marianne bring an emotional quality to the story that would be missing without them,” Cooper remarks. “It is only through their eyes that we see this facet of Whitey Bulger and John Connolly, respectively.”
The producers knew that director Scott Cooper was the right choice to capture the themes of deception, ambition and often misguided loyalty woven throughout the film. Lesher recalls, “When we met with Scott, one of the things he said to me, which I loved, was that he wanted to focus on the characters as people first. Then he would sort of pivot the point of view and show what they were up to. I think he really achieved that without making them sympathetic or excusing their actions.”
“You need a very skilled and extremely intelligent director to figure out how to make a movie work where there are truly no good guys, and in ‘Black Mass,’ that’s definitely the case,” Oliver notes. “To pull off a story where the characters have real arcs, but without any of them as your hero, is a hard thing to do, and Scott navigated those waters amazingly well.”
“Scott Cooper is a rare talent,” Depp attests. “I was blown away by ‘Crazy Heart’ and ‘Out of the Furnace’—the depth he exhibited that you might not expect from a relative newcomer—and I really wanted to work with him. On the set, I found it remarkable that this was only his third film. I was stupefied by his ability, the strength of his vision and his passion. He ate, drank and slept this film. I mean, the dude’s amazing; I’d shoot the telephone book with him,” the actor smiles, emphasizing, “I would! I have tremendous respect for him; he’s a great filmmaker with an enormous future.”
Kevin Bacon, who appears as Connolly’s direct superior in the film, adds, “I’ve admired Scott’s work and appreciated his process on the set. He fostered a very open and collaborative atmosphere among the cast, so it was a shared and very rewarding experience.”
Rounding out the main cast were Rory Cochrane, Jesse Plemons, W Earl Brown, Corey Stoll, Peter Sarsgaard, Adam Scott and Juno Temple.
One element as important to the fabric of the story as the characters was the city in which the drama unfolded. “Black Mass” was filmed in Boston because “it could not have been shot anywhere else,” Cooper states. “For me, a specific location or a city allows the audience to really grasp a certain place and time, and Boston is a very distinct town.”
Producer Tyler Thompson agrees. “Boston plays its own role in the movie that couldn’t have been duplicated anywhere else. It’s an amazing place and the people were wonderful.”
“It’s a homegrown story,” producer Patrick McCormick affirms. “It still echoes throughout those neighborhoods. We needed to be there to catch the voices, the architecture and, whenever possible, the actual locations where some of the events happened.”
“We understand that people and events get modified for the purpose of a movie,” Lehr says, “but accuracy in the setting and surroundings is still key, and the cast and filmmakers had almost an obsession to get that right.”
Cooper asserts, “All films are challenging in one way or another, but especially so when you’re dealing with any kind of truth. This particular story was sprawling and had a large cast of players with many different vantage points, so the truth often seemed elusive. It took a great deal of work to creatively show what happened as faithfully as possible.”
