The IRA supplier with an Irish passport who became one of America’s most wanted men
The focus of Hollywood blockbuster, Black Mass ‘Whitey’ Bulger was a vicious thug whose links to the FBI helped him build a criminal empire
INFAMOUS gangster James ‘Whitey’ Bulger was found dead in his cell yesterday at a prison in West Virginia, US, a day after his transfer to the maximum security facility. From the tough streets of the South Boston projects where he grew up, to the top of the FBI’s most wanted fugitives list, the 16-year manhunt to capture him finally came to an end in 2011. Here we revisit the genesis of his nefarious criminal career...
THE official police mugshot doesn’t give much away. Like most similar portraits, there is a distinctly grim look on the subject’s face. But there is nothing in the photo to suggest anything sinister about the balding elderly man with the neatly trimmed grey beard looking back.
If anything, he looks like a schoolteacher with a reputation as a stickler for disciplineand punctuality. Yet the reality is rather different. Behind the slightly stern-looking demeanour is one of the most notorious and violent figures in the history of organised crime. Now aged 86, James ‘Whitey’ Bulger — prisoner number 02182-748 — was at one stage second only to Osama Bin Laden on the list of the FBI’s most wanted fugitives.
His name has been linked to 19 murders and countless gruesome events involving victims being tortured, bound in heavy chains, shot and buried in cellars with their teeth removed to prevent identification.
Not, though, that Bulger was always destined for a life on the wrong side of the law. To make a compelling story even more incredible, his younger brother went on to become a leading politician and one of the most respected members of society in their home state of Massachusetts.
Now Bulger’s extraordinary reign of terror and carnage has been recreated on the big screen in Black Mass, which opens in cinemas this weekend.
Wearing facial prosthetics and various thinning hairpieces, Johnny Depp’s portrayal of the brutal mobster is being hailed as his best performance for almost two decades.
The story begins about four miles north of Boston in the town of Everett, where Bulger was born in September 1929. He was the eldest of six children in an Irish-American family.
His father, James senior, worked as a docker, but found himself unemployed after losing an arm in an accident. Due to the poverty that ensued, the family moved to a social housing project in the tough neighbourhood of South Boston when Bulger was eight years old.
Yet while his siblings studied hard and did well at school, Bulger started veering off the straight and narrow from a young age. By the time he reached his teens, he already had a reputation as a street fighter and a thief. Unsurprisingly he had also come to the attention of local police officers, who nicknamed him ‘Whitey’ because of his distinctive blond hair.
It was at the age of 14 that he was first arrested for theft. By now, he was a member of a street gang called ‘the Shamrocks’ and convictions soon followed for assault, robbery, extortion and forgery. Spells in juvenile detention centres did little to deter him from becoming a one-man crime wave. Nor did a stint in the US Air Force, which he joined at the age of 18.
After training as an aircraft mechanic, he was stationed initially in Kansas and then Idaho. But he ended up in military prison over a number of assaults and was arrested for going absent without leave at one stage.
He managed to leave the forces with an honourable discharge, however, and returned to Boston. It was at this point that his burgeoning criminal career took a crucial twist.
In 1956, the 25-year-old Bulger was sent to a federal jail for the first time after being convicted of armed robbery and hijacking. According to some reports, he was one of the inmates given LSD and other substances as part of a CIA research programme into mind-control drugs.
What is certain is that he was such a troublesome prisoner that he was ultimately transferred to Alcatraz, the notorious maximum security prison in San Francisco Bay, as one of the last batch of jailbirds sent there before it closed in 1963.
After doing time in two other institutions, Bulger eventually emerged a free man in 1965 following nine years in custody. Unlike many felons, he never boasted about his incarceration.
‘To him,’ said William Chase, an FBI agent who spent years pursuing Bulger, ‘prison time was evidence of failure.’ Back on the streets, he was determined to do two things: stay out of jail and establish a criminal empire.
Though he at first took jobs as a janitor and construction worker, Bulger quickly got involved in bookmaking, debt-collecting and acting as an under-
He was first arrested for theft at 14
world enforcer.
Before long, he managed to take over a small-time operation called the Winter Hill Gang and transform it into Boston’s most ruthlessly efficient crime syndicate.
Its main areas of activity were drug running, gambling and prostitution. Bulger based his modus operandi on the Mafia, which controlled the city’s northern suburbs. But unlike some of his Italian counterparts, he was supremely disciplined. Not only did he not while away lazy afternoons over long lunches in neighbourhood restaurants, Bulger appeared not to have any vices. He didn’t drink, didn’t smoke, never used credit cards, didn’t even gamble.
What little time he spent away from his nefarious business was largely devoted to body-building and reading. He always had an interest in history, especially anything involving Adolf Hitler.
Much of his energy also went into trying to become a master of disguise. He dyed his hair different colours and wore varying styles of glasses, although most observers agree that he found it impossible to mask his thick Boston accent. Another thing that Bulger struggled to hide was his volcanic temper. Even in seemingly casual conversations, he was prone to explosive outbursts.
Meanwhile, his propensity for extreme violence shocked both hardened criminals and police alike. Rivals and enemies were brutally killed either by Bulger himself or on his direct orders.
His former right-hand man Kevin Weeks later said: ‘He stabbed people. He beat people with bats. He shot people. Strangled people. Run over ‘em with cars. After he wouldkill somebody, it was like a stress relief, y’know? He’d be nice and calm for a couple of weeks. Like he just got rid of all his stress.’
Given such brazen criminality, it wasn’t long before questions were asked about how he was allowed get away with it. The answer was a long time coming and, when it did, it was a shocking one: Bulger had been operating as an FBI informer since the mid-1970s.
From his perspective, it was a perfect arrangement. He tipped off his Bureau handler and childhood friend, John Connolly, about other criminal activity in Boston in return for being allowed to proceed unimpeded with his own activities. The information he passed on virtually wiped out the Mafia presence in the city. Wanted: Whitey’s FBI poster
It was the 1990s before the Boston Police Department and the Drug Enforcement Agency, angered at the FBI’s failure to act, launched their own investigation. After being tipped off by Connolly — who was later jailed for ten years for obstructing justice — that the authorities were on to him, Bulger vanished on December 23, 1994.
During his years on the run, various sightings were reported from locations as diverse as New Zealand, Canada, Italy and along the US Mexican border. It was also claimed that he snuck into a screening of The Departed, the 2006 movie loosely based on his crime empire, in a San Diego cinema. There was even a suggestion that he hid out for a time posing as a sheep farmer in Donegal.
At the very least, he certainly maintained contacts in this part of the world. Twelve years ago, a safety deposit box belonging to Bulger was found in a London branch of Barclays Bank. It contained £45,000 (€50,000) in various currencies and a membership card for a West End gym, as well as the key to another deposit box in Dublin, where a further sum of cash and an Irish passport in Bulger’s name were discovered.
One of the few people known to have been in touch with Bulger during his years as a fugitive was his brother Billy, five years his junior. Billy, who is played by Benedict Cumberbatch in Black Mass, was a prominent figure in the Democratic Party and served for almost 20 years as president of the Massachusetts State Senate.
He later became president of the University of Massachusetts, but was forced to resign after admitting that he spoke to his brother by phone shortly after he fled and had failed to inform the authorities that the conversation took place.
When justice finally caught up with James ‘Whitey’ Bulger, it was in an unlikely manner.
The $2million bounty offered for his capture — the largest ever for a domestic American fugitive — had failed to produce a result.
It was his long-time lover, a glamorous 64-year-old blonde named Catherine Greig, who indirectly led the authorities to him. In a 2011 media campaign targeting female chat show viewers, investigators sought information about Ms Greig in adverts that described her as having a penchant for plastic surgery and beauty salons.
One of the tip-offs led detectives to a residential block in Santa Monica, California, where Bulger and Greig were living in an apartment close to an Irish pub popular with members of the city’s Bostonian community.
In June 2013, Bulger went on trial accused of 32 counts of racketeering, which included allegations that he was complicit in 19 murders. The two-month hearing, which included testimony from more than 70 witnesses, resulted in him being convicted of 11 of the murders.
It also heard evidence that Bulger supplied the arms and ammunition used in the IRA’s Marita-Ann gunrunning escape in 1984, which resulted in current Sinn Féin TD Martin Ferris being jailed for ten years.
Sentencing him to two life sentences plus five years, the judge told Bulger that he had been involved in ‘unfathomable’ crimes that involved ‘agonising’ suffering for his victims.
There is a scene in Black Mass that doesn’t contain any violence, but offers a terrifying glimpse into Whitey Bulger’s mindset. It happens during a cordial dinner scene at an associate’s home.
Bulger compliments the host on his steak marinade and, through flattery and cajoling, eventually gets him to reveal the ‘secret’ recipe. It is at that point that Bulger turns nasty.
‘You said to me this is a family secret, and you gave it to me, boom, just like that,’ he hisses. ‘You were “just saying”. Just saying gets people sent away... Just saying can get you buried real quick.’
Against all the odds, James ‘Whitey’ Bulger eventually got sent away himself. That he was caught at all is a bigger surprise than the fact that he managed to get away with it for so long.
‘One of the things that intrigued me,’ explained Black Mass director Scott Cooper recently, ‘was that lawmen and criminals in South Boston in the 1970s and 1980s were virtually indistinguishable.’
It was claimed he hid out as a farmer in Donegal