Should you be in any doubt as to the extent of the menacing nature of Irish-American mobster James “Whitey” Bulger, immortalised by Johnny Depp in the new crime film Black Mass, then consider this. When Osama Bin Laden was captured in 2011, Bulger ascended to being number one on the FBI’s most wanted list.
After spending 16 years on the run, the Boston gangster was apprehended in Santa Monica, California, and convicted of 11 murders in 2013. He is currently serving life imprisonment in Florida.
Black Mass, opening this month, chronicles Bulger’s reign of terror and will do nothing to diminish his infamy.
But it’s far more than a clear-cut depiction of evil. The film covers Bulger’s unholy alliance with his childhood friend FBI Agent John Connolly (Joel Edgerton) as well as with his upright politician brother Billy Bulger (played by Benedict Cumberbatch) who rose to become President of the Massachusetts Senate.
Both relationships helped ensure Bulger evaded justice for four decades as he built up his Irish-American Winter Hill Gang from small-time racketeering and debt collecting and became the most powerful gangster of his time in the process.
Among the themes explored in Black Mass are the bonds of brotherhood, how crime impacts a community and the complicity between law enforcement and the lawless (the FBI turned a blind eye to the illicit activities of Winter Hill Gang in exchange for information Bulger supplied that helped the FBI decimate the Italian mafia in Boston).
But another key theme of the film according to American director Scott Cooper is Whitey Bulger’s sense of Irishness. “I have great reverence for the Irish nation from a personal standpoint and a musical standpoint and I tried to reflect this in the film,” Cooper tells the Examiner.
Bulger was the son of an Irish-Canadian father and an Irish- American mother and moved to South Boston when he was nine. “South Boston is an extremely Irish tightly-knit community,” Cooper says. In Black Mass, Kevin Weeks, a member of the Winter Hill Gang played by Jesse Plemons from Breaking Bad, declares “Us Irish Southie kids went straight from playing coppers and robbers on the playground to doing it for real in the streets. Just like on the playground, it wasn’t easy to tell which was which.”
“Whitey felt very strongly about his ties to Ireland and what I hoped to do in the film was explore this notion of loyalty whether it was the Bulger brothers being extremely loyal to one another or their loyalty to their old country,” says Scott Cooper.
This loyalty was taken to extreme limits by Bulger who, in Cooper’s words, “wanted to help the Irish Republican Army as much as he could.” Although South Boston has become increasingly gentrified in the 21st century, in the 1970s and 1980s it was a locale unto itself where money was raised for the families of IRA prisoners and streets were decorated with Republican murals.
Bulger increasingly became drawn into the struggle. “He did possess a deep love of Ireland,” says Dick Lehr, co-author of the book Black Mass on which the film is based. But Bulger’s love for the IRA would prove to significantly lead to his undoing.
In an event depicted in the film, in 1984 the Winter Hill Gang arranged for a fishing trawler Valhalla to carry seven tons of weapons from Massachusetts to the IRA in Northern Ireland. Although the guns and explosives were transferred to the fishing vessel the Marita Ann, the Irish navy had been tipped off and captured the weapons arsenal.
A few weeks later a Valhalla crew member John McIntyre was arrested on a drunken driving charge and revealed the full extent of the drug-smuggling and gun-running of the Winter Hill Gang to the authorities.
Although McIntyre had not mentioned Bulger by name as overseeing the operation, when Connolly heard about the confession that threatened to blow open the criminal activities of Bulger, he tipped off his childhood friend.
McIntyre was murdered by Bulger and two other gang members shortly afterwards for being an informant. His body was found in Dorchester, Massachusetts, in 2000 and over a decade later Bulger was convicted of his murder.
“In some sense Whitey was able to fortify their fight, as he saw it, against injustice,” says Cooper, “but in the end his commitment [to the IRA] helped bring him down because of the relationships and murder that took place in the wake of the Valhalla. “ A Bulger lieutenant Patrick Nee, jailed for his part in the Valhalla gunrunning, wrote in his memoir A Criminal and an Irishman: The Inside Story of the Boston Mob-IRA Connection: “Whitey loved being associated with the IRA and the cause of Irish freedom.”
After the Valhalla incident, the relationship was never the same between Bulger and IRA. Indeed investigators suspected Bulger himself betrayed the IRA by informing on them. “He supported the gunrunning, such as with the Valhalla,” says Black Mass co- author Dick Lehr, “but when the truth came out about Whitey being an informant, I think he worried because the IRA is no friend to an informant. That’s when it became complicated.” Black Mass doesn’t shy from complexity in chronicling Bulger’s ties to law enforcement authorities and the FBI. “In South Boston in the 1970s and 80s, the circle of criminals and the circle of law was virtually indistinguishable,” says Scott Cooper.
It’s an ensemble film (Dakota Johnson, Kevin Bacon and Peter Sarsgaard are among those who feature in the film) but at the centre is Johnny Depp who has been tipped for an Oscar nomination for his performance.
In order to more closely resemble his subject, the Pirates of the Caribbean star had the upper half of his face covered with prosthetic and 50 different headpieces were created to mimic Bulger’s receding hairline. “Johnny, his make-up artist and I looked at all the surveillance footage of Bulger and knew we had to change his hairline and that he had to put on weight because Whitey was a stockier, muscular guy,” says Cooper.
“We had to get his physicality just right but Johnny is a brave actor and never afraid to take chances.” Depp’s transformation proved disconcerting to his fellow cast members. “I met Johnny in the production office with his tattoos and denim jeans- the iconic look I grew up with,” says the Australian actor Joel Edgerton.
“So for the majority of time I spent with him on set as Jimmy, it didn’t feel like there was much Johnny in there at all.” Cooper was determined to make Bulger as human as possible. “You want to get the story right,” he says, “I wanted to portray him as a very human figure who happened to be a criminal. Whitey was a dangerous, notorious figure but he was a man who was so many things to so many people; he was a father to one child who died and a loving brother but in the end his crimes speak for themselves.”
Depp, 52, and Cumberbatch, 39, make unlikely brothers but their good cop-bad cop dynamic is compelling in the film. “We don’t quite know what the relationship between the two brothers was like and how much Billy Bulger knew,” Cooper says. “But Benedict really understood the heart of this man and who Billy was to his community. Any time I visited Benedict’s trailer or his apartment in Boston, he was continually watching footage of Billy.”
Black Mass was shot on location in South Boston.
“It could not have been shot anywhere else,” says Cooper. “I shot in every corner of the city and the citizens of Boston for the most part welcomed us with open arms.” In many ways Black Mass is a portrayal of a bygone Boston era. Yet Edgerton can testify to the strong feelings that still run high in South Boston about Whitey Bulger.
“When I came to America to film Black Mass I came through the Canadian Border Patrol system and the guy stamping my passport was from South Boston, “ he says. “He knew I was an actor and I told him what I was about to do.
He said, only kind of jokingly, “You better not f**k it up!” As I was walking away, the next person in queue said, ‘Don’t f**k it up!” Confounding the warnings Edgerton received at border patrol, all the signs are that Black Mass will enjoy a more successful fate than the doomed Valhalla mission that helped set in motion Whitey Bulger’s demise.