Frightening Irish: The true story of Whitey Bulger

MoviesBy Esther McCarthy
James 'Whitey' Bulger
James 'Whitey' Bulger

There’s a chilling scene in the forthcoming Whitey Bulger movie which hammers home what a terrifying character the notorious criminal was.

During dinner at the home of an associate, Bulger praises the steak served by his host, before coaxing his pal to divulge the secret family recipe involved. 

It’s then that his tone changes, and an intimidating air fills the room. 

“You said it was a family secret,” chides a wide-eyed, angry Bulger as a look of dread spreads across his host’s face. “But you gave it up to me just like that. You spill a family secret recipe to me today, maybe you’ll spill something about me tomorrow?

“You’re just saying?” he continues, as the man attempts to defend himself.

“‘Just saying’ got me a nine-year stint in Alcatraz. And ‘just saying’ could get you buried real quick.” 

Moments later he’s chuckling amiably again, but for the terrified man across the table the message has been sent. 

It’s a scene that encapsulates how James ‘Whitey’ Bulger – the son of poor Irish emigrants James and Jane, who moved to south Boston for a better life – became one of the most violent and notorious criminals in U.S. history. 

His penchant for punishing betrayal with the harshest of violence made him one of the most feared men in America in the 1970s. And his ability to play both rival gangs and senior figures in the FBI allowed him to thrive unchallenged in the Irish community that was his stomping ground.

Now Hollywood is bringing Bulger’s story to the big screen. The movie, called Black Mass, is already arousing controversy amid claims it is glamourising the crook’s legacy at the expense of his victims.

Johnny Depp (above) has stepped up, growing a paunch and sporting a comb-over to capture Bulger at the height of his notoriety. 

“Historically, in terms of the city of Boston, it’s an important story,” said Depp. 

“James Bulger is a fascinating creature and we all want to know what drove him. But I don’t think it’s as easy as good and evil, and that’s what I hope to show.”

One movie insider said: “It’s a film that does not shirk in its depiction of what a terrifying man he was in his heyday. His ability to manipulate both other criminals and the law is brought to the fore, and it is Depp’s finest performance in years. I would expect it to be a big contender come awards season.” 

It’s unknown if the now 85-year-old Bulger – arrested in 2011 after 16 years at large and 12 on the FBI’s 10 Most Wanted Fugitives list – will be interested in seeing the completed film. 

He was finally arrested for his role in 19 murders in the 1970s and ’80s connected to his criminal dealings – though the actual figure is thought to be higher. 

He was convicted on 11 counts, though he fervently denied his involvement throughout the trial. 

They included the deaths of rival gang member Paul McGonagle, shot in the back of a car, as well as witness Edward Connors. They also pinned him for the death of rival gangster Thomas King, nightclub owner Richard Castucci and Roger Wheeler. 

Brian Halloran, an FBI informant, was gunned down outside a Boston restaurant. Halloran’s neighbour Michael Donahue, who had offered him a lift home, was also killed.

He was also convicted for the shooting of John Callanan, who he feared wouldn’t hold up if questioned about Wheeler’s death. 

Whitey was also charged to have chained alleged jewel thief and bank robber Arthur Barrett to a chair, made him reveal where his stash was, then shot him in the head. 

John McIntyre, a fisherman who Bulger suspected of talking to authorities, was shot. And Deborah Hussey was strangled after it was alleged she was ‘ratting’ on the Bulger gang. 

Based on the book penned by Boston Globe journalists Dick Lehr and Gerard O’Neill, the film singles out several major players in the Whitey Bulger story. 

It centres on the huge Irish community in working-class south Boston of the 1950s, where two boys – John Connolly and James Bulger – grew up and played together. 

Decades later, they would meet again. But by this stage Connolly – played by Joel Edgerton (above left with Depp) in the film – was a key figure in the Boston office of the FBI, and Bulger had become the self-styled head of the Irish mob. 

In a bid to curb the growth of the Italian Mafia in the city, the two brokered a dirty deal. Bulger would turn supergrass for the Feds, revealing secrets about the Italians’ crimes and movements. 

It was a deal that would end in disaster, allowing Bulger’s gang – who had strong connections to the IRA – to murder, intimidate, racketeer and terrify their way across the city with impunity. 

Connolly wasn’t the only powerful connection the Irish crook had in the city; his own brother, Billy (played by Benedict Cumberbatch (above) in the film), was one of Boston’s most-prominent Senators and lawyers. 

Billy once said he was “shocked” at the revelations in the trial. 

In a rare radio interview a couple of years ago, Billy said he sees his brother once a week in jail, but added: “Just because I visit him doesn’t mean I condone it. I don’t try to sort it out any longer. I just try to be a brother.”

Meanwhile, Dakota Johnson plays Lindsey Cyr, Bulger’s one-time girlfriend and the mother of the boy believed to be his only son. 

Douglas was a healthy boy who suddenly fell sick and died at the age of six from an allergic reaction to aspirin. 

“He changed after Douglas died,” she said in 2010. “He was colder.”

Several scenes in the forthcoming film set out to depict what a conniving character Bulger could be. 

At the dinner table, he’s filmed giving his young son some fatherly advice: “There are lessons to be learned throughout your whole life. It’s not what you do, it’s when and where you do it. And who you do it to or with. If nobody sees it, it didn’t happen.

The film also shows how his notoriety in the city grows, prompting one observer to say: “In the beginning, Jim was a small-time player. He’s a very smart, disciplined man.

Next thing you know he’s a damn kingpin and you know why? Because the FBI let it happen.” 

Another poses the question: “Why has nobody nailed Whitey Bulger? He seems to be involved in every crime in this city, and yet the Bureau keeps saying that he’s clean.”

Black Mass is released in Ireland on November 27