Johnny Depp stars as Irish mob boss and fugitive James “Whitey” Bulger, the notorious former member of Boston’s Winter Hill Gang, in the upcoming biopic Black Mass. Bulger’s criminal enterprises and escape have grabbed headlines for more than four decades, and nobody understands his story better than Boston Herald columnist and Breitbart News contributor Howie Carr.
Ahead of the film’s release, Big Hollywood spoke with Carr about the film, his connection to the gang’s unraveling, and his relationship with Bulger, who is now 86-years-old and will spend the rest of his life in prison following his 2011 capture in Santa Monica, CA.
Carr’s aggressive reporting on Bulger’s criminal organization resulted in multiple assassination attempts, according to State Police and DEA documents released at Bulger’s trial. Carr discussed the film’s portrayal of the notorious criminal, and his brother Billy Bulger, who served as the President of the Massachusetts State Senate from 1978-1996.
While the Bulger brothers maintained separate lives, they operated virtually unopposed within city and state governments in the 1970s and 1980s, and only a handful of journalists, including Carr, had the audacity to question the Bulger status quo, at a time when the threat of violence kept even the most respected journalists from talking.
Carr has spent much of his decades-long career covering the Bulger brothers, also authoring several books over the duo, including the New York Times best-seller “The Brothers Bulger.” While he has yet to see Black Mass, BH asked the author and journalist if Johnny Depp’s portrayal of the ruthless criminal looks to be authentic, based off of early trailers, to which he responded, “I couldn’t believe how well they captured Whitey.”
Back when he was still operating out of South Boston, “he’d be standing outside the liquor store. He’d do his business in the street, away from wires,” where the ambient noise gave him cover, said Carr.
The former FBI informant carried a sense of intimidation everywhere, which Carr says, aside from a slight size differential, Depp has nailed.
“They got it right, the menace, the intimidation,” he says. “Whitey’s job in the gang was intimidation, and from what I’ve seen, Depp has captured that perfectly.”
While Billy Bulger has never been directly linked to any crimes, Carr says, “I’m surprised the film is taking an honest look at Whitey’s relationship with Billy… One of them robs you with a gun, the other with a gavel.”
When asked if Benedict Cumberbatch looks to be portraying Billy accurately, Carr laughs, “He’s hard to figure. We are amused by the fact Ben is 6 feet tall. Billy was known as a corrupt midget, standing only 5’ 6’.”
Howie Carr first began covering organized crime in Boston in the 1970s, while working as reporter at city hall and the State House.
“I noticed a lot of gangsters were working there,” he says.
His duties as a journalist initiated a tense relationship with the Bulgers that did not conclude until Whitey’s 2011 murder trial, when he and other reporters were called as witnesses in Bulger’s defense; something Whitey planned as a strategy to keep them out of the courtroom.
“He did that with several Boston reporters. His greatest regret is not killing me,” says Carr. “He hates me, I’m one of the guys he blames for his downfall, and because I went after his brother, the corrupt midget.”
On the subject of Whitey’s hatred for Carr, a man named Mark Gallagher, who served time at the Plymouth House of Correction with Whitey before he was sent to prison, spoke with Bob Ward from Boston’s Fox 25 about his time with the gangster in 2014.
Ward asked the former inmate if there were still any people Whitey would like to settle a score with. Bulger has not forgotten about his old nemesis in the media.
“I asked him, I said if there’s one person on this planet that you could kill right now — without even — before I almost even finished the sentence, he said, ‘Howie Carr, I’d kill that bastard in a heartbeat,’” Gallagher said.
“Whitey is very defensive. he ruined his brother’s life,” Carr says of the anger Bulger still carries.
While Whitey successfully evaded capture from 1994 to 2011, despite being second on the FBI’s most wanted list (only behind Osama bin Laden) for a number of years, he was eventually brought in without a fight, while living in a small apartment in Southern California. BH asks Carr, “Were you afraid during the 16 years Bulger was on the run?”
“I was always looking over my shoulder,” says Carr. “The day he went missing, I was driving down the street, and on the radio they said he had disappeared. For the first time in 10 years, I didn’t have to look over my shoulder.”
Howie Carr no longer looks over his shoulder, and Whitey Bulger is still likely acclimating to prison life at 86-years-old.
Black Mass will debut September 18.
Watch the trailer below:
Howie Carr is the host of a New England-wide radio talk-show syndicated to more than 25 stations. He is also a columnist for the Boston Herald, and is one of Breitbart’s newest contributors.
His upcoming novel, titled Killers: A Novel, takes an in-depth look at crime in post-Whitey Bulger South Boston. The book will go on sale September 15.
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