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Murderer, Irish-American gangster, FBI informer: The Whitey Bulger story

The author of Black Mass and Bulger’s biography Dick Lehr speaks to us about the criminal’s life.

Updated Oct 30th 2018, 5:36 PM

Update: Infamous Irish-American gangster Whitey Bulger was found dead today in a prison in West Virginia. In 2015, we talked to his biographer about his career and crimes.

James_Bulger_1994 Source: FBI via WIkimedia Commons

IF THERE WAS one thing James ‘Whitey’ Bulger hated, it was a rat.

Informants were very high up on the Bostonian gangster’s list of things he detested. So why did he end up becoming one for the FBI?

His dirty deal with the agency – which helped him rise up the criminal ladder in Boston – is delved into in the film Black Mass, which stars Johnny Depp as the nefarious Bulger himself. 

Based on the book of the same name by Boston Globe reporters Dick Lehr and Gerard O’Neill, the film shows the lengths that Bulger (who boasted of his Irish heritage) could go to because of his deal with FBI agent John Connolly.

Dick Lehr spoke to TheJournal.ie about Bulger – who he describes as a psychopath – the new film, and the criminal’s connection to Ireland.

NEW ENGLAND MOB Source: AP/Press Association Images

Connolly (played in the film by a fantastic Joel Edgerton) and Bulger’s deep-rooted bond was down to the fact they both grew up in Southie, Boston’s tough southside area where many Irish settled.

Bulger made much of his connection to the ‘old sod’, and it helped him make and keep connections in the underworld, while keeping Southie locals sweet.

Southie is located across the bridge from downtown Boston, which helps to reinforce its isolation, says Lehr. The Irish in Southie tended to be the housekeepers and help of the upperclass Bostonians, and there was an ‘us and them’ mentality between people who grew up there and people from the rest of the city.

A tale of two brothers

Lehr and two other Boston Globe reporters set out under the watchful eye of Gerard O’Neill (who co-wrote Black Mass) in the spring of 1988 to write a profile of Whitey Bulger (then 58) and his brother Billy Bulger, who was then a 54-year-old Massachusetts state senator. (In 2011, RTÉ Doc on One spoke to Billy for his first interview since 1992 – he hasn’t gone public since.)

That the two men were so different – and so powerful – in their chosen fields was a fascination to many in Boston.

“That story of the profile of the two brothers was in many ways the dream story – it was so fascinating that these two brothers in the 1980s, when we did the story, were at the top of their games in the underworld and politics,” says Lehr.

The pair had grown up and shared a bedroom in the same housing project in South Boston, yet both were drawn to two very different sides of life.

Though Bill Bulger (played by Benedict Cumberbatch in Black Mass) “largely stayed within the boundary lines of society and law”, he did share some traits with his brother. “Whitey immediately crossed the line from the start and found his groove outside the law,” says Lehr. “But they do share, interestingly, a number of personality traits.”

“Very tough, very loyal, very political”

While Lehr describes Bulger as “extreme – I don’t think anyone would dispute he is a psychopath”, of his brother he says: “I don’t think Bill Bulger [is a psychopath]. They are both very tough, very loyal, very political and calculating in terms of seeing the chessboard and working the next move and applying that genius to their next game.”

In politics, if you opposed Bill Bulger you paid a big price – it wasn’t with your life like Whitey Bulger would do it.

In the book, Lehr describes how he and his colleagues were “flat-out incredulous” at the rumours that Bulger was an informant. He seemed far too entrenched in the criminal way of life, where ‘rats’ were seen as “just as bad as rapists”, in the words of one of Whitey Bulger’s underlings, John ‘Red’ O’Shea.

“It was unthinkable at the time that Whitey Bulger, with his Southie and cultural Irish heritage, would be an informant,” says Lehr. (Bulger wasn’t alone – one of his fellow gang members, Stephen Flemmi, was also an FBI informant.)

But Whitey had served just one jail term – nine years in the notorious Alcatraz prison – and had never been arrested since his return to Boston in 1965. He’d gone from a foot soldier in the Winter Hill Gang to an underworld boss.

The Irish link

James_J._Bulger_-_1959_mugshot Alcatraz mugshot of Bulger in 1959 Source: Federal Bureau of Prisons via Wikimedia Commons

Bulger’s Irish heritage meant a huge amount to him, but perhaps only so far as it helped to cement his links within both his local community and criminal community.

“I think in terms of Whitey – I think this is part of the evidence of his narcissism and that he is a psychopath – he embraced the values of neighbourhood and loyalty, all those things he inherited from the Irish connection,” says Lehr.

He inflated them; that’s what he was all about. He protected his neighbourhood but that was part of the myth of Whitey Bulger: what mattered was him. The cultural things which I alluded to, he used them as tools to power because the biggest one was the myth of Whitey Bulger keeping drugs, heroin, cocaine, out of the neighbourhood.

It was one thing, says Lehr, for Whitey to be into loan sharking and murder, but he would not let drugs into his neighbourhood.

While writing their biography of Whitey Bulger, O’Neill and Lehr discovered that Bulger was economical when it came to his family’s connection with Ireland.

“Everyone here assumed the Bulgers came directly from Co Wexford, but in fact they’d gone through Newfoundland and there had been three to four generations of Bulgers in Newfoundland before they made it to Boston,” says Lehr. “I don’t know why they would want to do that. Somehow it mattered to Bulger and the Bulger myth and the story they told about the family history.”

Most people thought of the Bulgers as “sons of Southie”, who were born and raised there, when in fact Whitey was nine when the family moved to the neighbourhood.

Lehr describes this fudging of the truth, this massaging of the Whitey myth, as “part of his genius”. “He cultivated this Robin Hood myth about him,” he says. “With a politician’s touch, he would help a family in need or hand out a turkey at Thanksgiving, so the neighbourhood, those around him would feel good about him – ‘he’s our bad guy’.”

But, says Lehr, this helped to mask the danger that Bulger was actually putting the neighbourhood in: “He was happy to move drugs in there; if someone opposed him, he didn’t think twice of eliminating them”.

“In the end,” says Lehr, “it’s all about Whitey.”

Does Lehr ever feel sympathy for Whitey Bulger? The author says he has, but only in relation to one thing: the death of Bulger’s young child from an illness.

“And that was the one moment – I’m a parent, he grieved in that moment, as monstrous as he is. I don’t know if sympathy is too strong a word, but he suffered then.”

“Tucked-in rage”

Whitey_Bulger_US_Marshals_Service_Mug1

Lehr was impressed with Depp’s rendering of Bulger on screen, saying that when he first saw an early cut of the film it blew him away: “it was disorientating”. “He was so capturing this cold and menacing, I call it tucked-in rage. Whitey was kind of tucked in and taut, but in an instant he could explode and I think Depp had that.”

Police surveillance tape showed Whitey as a lean man, one with a “stomach flat, arms tucked in, shirts folded, and this rage right underneath it all”, says Lehr.

Whereas the other criminals are depicted in Black Mass as being doughy, Bulger is shown working out and keeping fit. “That’s the real Whitey – very disciplined, and when he did that one stint in [Alcatraz] prison he got real into both physical discipline and emotional discipline and that’s all reflected in Depp’s portrayal.”

It’s a challenge to distill Bulger’s story into a two hour movie (Black Mass doesn’t linger on his time on the run, or on his capture, preferring to instead focus on his time under the FBI’s wing).

Whitey Bulger Arrested Source: AP/Press Association Images

“I do think they captured the essence, which was this dark and deadly deal between a crime boss and a corrupted FBI,” says Lehr.

I don’t like anyone to think it was just John Connolly and John Morris, two rogue agents, two bad apples. The corruption in the FBI was systemic and institutional. More than a dozen agents were involved and Connolly and Morris were at the centre of it.

As a journalist, Lehr took satisfaction in unmasking the ‘dirty deal’ between Whitey and the FBI, and making it public. “There was a sense that it was important that the American public learn about that,” he says now.

The capture of Whitey Bulger

Whitey Bulger Arrested Source: AP/Press Association Images

Whitey Bulger went on the run in 1994. For years, the only person more sought after than him on the FBI’s most wanted list was Osama Bin Laden.

When Bin Laden was killed, Bulger knew that the jig was up. He was living at the time in an apartment in Santa Monica, California, with his partner Catherine Greig,

They were known as Carol and Charlie Gaskos, but Bulger had a range of aliases that he would use, depending on the situation.

As the Boston Globe reported, Carol Gaskos would tell neighbours that her husband had schizophrenia, in order to deter people from asking questions. Their neighbours knew them as a quiet, friendly retired couple.

But Carol and Charlie Gaskos lived a life built on lies, and in a bizarre twist it was their kindness to a small cat that led to their undoing.

Bulger and Greig were eventually found after an old neighbour, who had noticed them feeding a local stray cat, spotted a news report about them on the TV.

She recognised them instantly. She picked up the phone in Iceland and called the FBI, ending a decades-long manhunt.

Their kindness to that tiger-striped cat saw Greig and Bulger being hauled into police custody, and Bulger’s arsenal of weapons being discovered hidden behind holes in their apartment walls.

Whitey Bulger Whitey Bulger in court Source: AP/Press Association Images

Bulger was found guilty of racketeering, murder, conspiracy to murder, money laundering and other serious offences. He was sentenced to two terms of life imprisonment. He will spend the rest of his life in Coleman II United States Penitentiary in Sumterville, Florida.

In March 2012, Greig was sentenced to eight years in jail. She is incarcerated in a low-security prison in Minnesota. Her crimes included conspiracy to harbour a fugitive, one Whitey Bulger.

“Dick, he’s never going to talk to you guys”

Though he has written two books about Whitey Bulger, Lehr is yet to meet the man himself. It’s not for want of trying – he has tried, and tried, and tried again.

His last attempt was in 2011, after Whitey was captured. “I think I wrote Whitey five times trying to get a jailhouse interview, but his lawyer finally came up to me and said ‘Dick, he’s never going to talk to you guys’.”

Lehr is happy to see Bulger caught and in jail, and doesn’t underestimate his legacy.

“He’s done such incalculable harm to the neighbourhood, to the city, to justice, [through] corruption with the FBI,” says Lehr.

“It’s still staggering, not just a single case or family with a murder, it’s staggering because it went on for several decades.”

Read: “Justice has been served” – Boston mobster ‘Whitey’ Bulger found guilty of 11 murders>

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