EXCLUSIVE: A day after 89-year old iconic South Boston mob boss James (Whitey) Bulger was beaten to death — his face reportedly pummeled beyond recognition by prisoners with mob ties and a grudge — in a West Virginia prison, I asked Scott Cooper how he would script Bulger’s headstone.
While several major movies and TV productions were built around composites of Bulger – Jack Nicholson’s performance in Best Picture winner The Departed and the James Woods arc in Ray Donovan come to mind — Cooper was the one who actually took the elusive subject head on when he wrote and directed Black Mass and cast Johnny Depp to play the feared mobster and FBI informant who held South Boston in his iron grip and enjoyed a second act by hiding from authorities nearly two decades as the second Most Wanted Fugitive behind Osama Bin Laden after being tipped to an imminent indictment for his role in 19 murders.
Whitey Bulger Dies: Mobster-Turned-Informant Inspired Film & TV Characters
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I caught up with Cooper by phone in British Columbia on his way to the set of Antlers, the Fox Searchlight film Cooper is directing in locations that could be used for witness protection. They are so remote that a lack of cell service kept him in the dark about Bulger until last night, when Cooper’s wife got an emergency message passed to him.
“Whitey Bulger’s headstone? I don’t really love going back into that head space,” Cooer said. “But I guess what I’d write is, ‘Life is a boomerang, and I got what I deserved.’”
Cooper soon warmed somewhat to the memory of the 2015 film that, before it was said and done, left him on the receiving end of threats to his life, though he didn’t want to get specific about them.
“I will say, anytime you make a film about real life events and you try to do it with the type of authenticity I was striving for, you never stop looking over your shoulder. You make a movie about people like that who might not like the way they’re portrayed, and watch out,” Cooper told Deadline.
Though Cooper and his cohorts immersed themselves in researching the life of Bulger and his former mob associates — many of whom worked on the movie or at least shared stories of Bulger’s Winter Hill gang whose reign was helped by the mob leader ingeniously using his status as FBI informant to eliminate criminal rivals – neither the filmmaker nor his star ever had a conversation with the now deceased Bulger.
“Both Johnny Depp and I reached out to Whitey and he explicitly denied us,” Cooper said. “He denied he was ever an FBI informant and that’s where the film got gray. He was certainly an informant but the question was, how much was he giving them? He was enriching himself, and he was enriching John Connolly, the FBI agent who was his childhood friend.
“My first thought about Whitey Bulger is for all the victims and their families,” he said. “There were many more deaths that occurred than I portrayed in the film. I can’t say I’m surprised this happened,” Cooper said. “The mob has a very long reach, and I guess I am surprised it took this long. The prison to which he was transferred was understaffed and short some 40 officers. It seems like certain people were lying in wait for him.
“The other thought is what happens when your life starts off as young delinquent, and you never get it back on track,” Cooper said. “Whitey wrote to some students not long ago that his life was wasted and foolish. Perhaps he was being sincere when he wrote it, but one can never tell when he was being truthful, amidst the loan sharking, the drug dealing, the gambling and the murders. It was more than the murders, it was the way he murdered, and that included killing women with his bare hands. He tortured people.”
Cooper got plenty of creepy stories from Jesse Plemons and Rory Cochrane. Those actors — who are now part of Cooper’s Antlers cast — played Bulger henchmen Kevin Weeks and Stephen Flemmi, and embedded deeply in South Boston. There, they heard war stories that made it clear the movie only scratched the surface of Bulger’s brutality. Both actors but especially Cochrane — he played Bulger’s executioner Flemmi — took a long time to shake the nightmarish memories accumulated.
There was also a toll on Depp himself, who, Cooper said, captured Bulger’s steely calm menace and ferocious temper so convincingly that former associates who came to the set felt like they were looking at the real guy.
“I’d say to Johnny, ‘Whitey was like a rattlesnake,’” Cooper recalled. “You never knew when he was going to strike. And when he strikes, it’s fast, quick and deadly. Johnny was able to turn on a dime, like Whitey did. He could be very charming and loving, and in a split second, be a man who could either have a gun to your head or already have killed you, without you having seen it coming. Johnny was always able to keep that sense of potency alive in Whitey along with the charm. Many people who worked on the film and knew Whitey intimately, and one of them was Whitey’s longtime attorney. He pulled me aside and said, ‘it’s as though I was sitting across from Whitey.’ Johnny didn’t look like Whitey, who had very piercing blue eyes that he used to intimidate. That transformation for Johnny was very important to him, to physically get that characterization right.
“Once he was able to literally and physically crawl into Whitey’s skin, I lost sight of Johnny Depp as he completely gave himself over to who he thought Whitey Bulger was,” Cooper said. “I’ve had two occasions in my short working life as a filmmaker, where two actors said they couldn’t wait to shed the skin of their characters. One was Johnny Depp as Whitey Bulger, and other was Woody Harrelson in Out of the Furnace. It was very difficult for both men to live in the skin of those characters for as long as they had to. Johnny was relieved when it was over.”
Cooper also struggled with directing the film. Mobsters, living large and lawless, have been a perennial draw in hit films and stone killers from Al Capone to John Gotti get routinely romanticized. Cooper said he couldn’t forget the carnage that Bulger left in his wake and was mindful to not get caught up in that.
“People come to the movies to be entertained, and Martin Scorsese and Coppola are to me the two best living directors, and you would be foolish to make a film and try to evoke what they did,” he said. “So I never set out to make a film about criminals who just happened to be humans. Rightly or wrongly, I wanted to make a film about humans who happened to be criminals. I wanted to take a look at a man who on one hand could be as vicious as anyone who walked the earth, but who also struggled with the loss of his son or his relationship with his mother. I had no interest in making a film that looked at the high life of a gangster. In fact, I wanted to make an anti-gangster film. So often you get criticized for that because people want to see gangsters depicted as high rolling, high living, really complex but colorful characters. While I tried to do that in a very humanistic way, some liked it and some didn’t.”
Still, Cooper understands why Bulger’s sociopathic blend of charm and murderous rage makes for a good movie villain.
He recalled inviting relatives of some of Bulger’s victims to the film’s Boston premiere and feeling how torn they were between appreciating the dedication to detail that included reenacting murder scenes in the actual South Boston locations, and seeing their worst nightmare replayed as loved ones were killed.
“They thought it was an extremely accurate portrayal, as hard as it was to see the events take place and reopen wounds that were probably will never heal,” he said. “Some reached out to say that while it was difficult, it was an authentic portrayal. They knew the duality that existed within Whitey Bulger, but it’s never easy to see your loved ones ultimately murdered onscreen in ways that were accurately portrayed because I dealt closely with the FBI in Boston and in the end in Los Angeles, these people who chased Whitey for years. One strong supporter of the film was Chief William Bratton, who was police commissioner in New York, LA and Boston. He told me he would be on the beat as a young cop in Boston, and they would drive by Whitey’s garage. And there Whitey would stand and star, much like he did in the film, with his arms crossed at the door. He and his patrol partner would stop and they would look at Whitey. He said Whitey could intimidate you literally from that garage door into your car. He said he hadn’t experienced anything quite like that.”
Cooper said that Bulger’s spell over a prison psychologist might have shown his peculiar gift to mesmerize his subject hadn’t faded, but that it might also have been his undoing by leading to a transfer to a prison that didn’t have enough guards, but allegedly several connected prisoners with long memories.
While the filmmaker got his fill of Bulger in making Black Mass, he believes that public and Hollywood’s fascination with the mobster will likely mean that we haven’t seen the last of the Winter Hill gang leader onscreen.
“In retrospect, I think Whitey Bulger’s story is so epic that it should be told in an eight-hour miniseries that could delve more fully into his relationship with his brother, who was the most powerful politician in the city while Whitey created his ring of extortion, robbery, murder and drug dealing in Boston,” Cooper said. “It’s always going to be difficult when you make movies about real characters who are alive and might not like the way they’re portrayed. Sam Shepard made Out of the Furnace with me and told me not long before he died, to keep trying to tell the truth. As an artist, that’s what you are beholden to. Whitey Bulger was a tough story to crack because it was so large. So I did the best I could in a two hour time frame.
“And I understand how many would think, an eye for an eye, and that Whitey got his just desserts,” Cooper said.
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