Who was gangster James 'Whitey' Bulger?

On June 22, 2011, one of the largest manhunts in American history ended with a whimper in a quiet Los Angeles suburb. After being lured from his apartment on a ruse, an 81-year-old Irish-American man was pounced on by FBI agents and charged with extortion, money-laundering, narcotics distribution and homicide.

These charges stretched back 40 years, and included at least 11 counts of murder: when agents searched the man’s apartment, they found over $800,000 in cash, numerous fake IDs and 30 firearms. This pensioner clearly wasn’t joking.

He, of course, was James ‘Whitey’ Bulger, the notorious south Boston mobster who’d been on the run for 16 years and on the FBI’s most wanted list for 12 of them. A bounty of $2m had been placed on Bulger’s head, and his story had become a great favourite with the tabloids. And little wonder, because it’s so unlikely it sounds like it was dreamt up by a drunken screenwriter.

He ran guns to the IRA, was a secret FBI informant, and his younger brother was a state senator. Whitey’s story has inspired numerous TV shows and movies, including Martin Scorsese’s The Departed, but Scott Cooper’s new film Black Mass sets out to tell the real, unvarnished story.

Virtually unrecognisable with bald head, bad teeth and ice blue contact lenses, Johnny Depp plays Bulger, the much-feared and chillingly calm leader of the Winter-Hill Gang. Benedict Cumberbatch is his younger brother Billy, a high-flying politician whose career will be dragged into the ditch by his brother’s notoriety, and Australian actor Joel Edgerton is John Connolly, a flashy south Boston FBI agent who gets caught in Whitey’s web.

“Above all, the last thing we wanted to do was glamorise him,” says Scott Cooper (see panel), and Black Mass certainly doesn’t do that. It paints a grim portrait of a gifted, enigmatic and very intelligent man for whom killing was just business, part of everyday life.

James Bulger isn’t just vaguely Irish-American – he’s Irish through and through. His father, James Senior, hailed from a large Newfoundland Irish-American family, and his mother, Jean McCarthy, was first generation. James Junior was the eldest of three brothers, and after his father lost his arm in an industrial accident, the family fell on hard times and ended up in a tough south Boston housing project. And while his two younger brothers excelled at school, Jimmy was drawn at an early age into a life of crime.

By the age of 12 he’d developed a reputation as a petty thief and street-fighter, and at 14 he was arrested for petty larceny. He ran with a street gang called the Shamrocks, and the local cops took to calling him ‘Whitey’ on account of his distinctive blond hair. He always hated the nickname, and woe betide those foolish enough to use it in his presence.

Bulger joined the US Air Force in 1948, but proved too tough a nut for the armed forces to crack: he assaulted comrades several times, and was arrested for going AWOL. After returning to Boston in the mid-1950s he was arrested for armed robbery and hijacking, and spent nine years in Atlanta Penitentiary and Alcatraz. And when Whitey got out in 1965, he began to reveal his criminal genius.

After a brief stint as a janitor and builder, Jimmy Bulger branched out into loan-sharking and began working with Irish mobster Donald Killeen. When a gang war between the Killeens and rival family the Mullens broke out in 1971, Bulger went to battle for the Killeens and committed what may have been his first murder.

But when Donald Killeen was shot dead, Bulger switched sides and joined forces with the Mullens to become a real force in south Boston’s underworld. Through the 1970s, he brilliantly played off his enemies against each other, and at the end of that decade took over the Winter-Hill gang following the arrest of their boss Howie Winter.

Whitey was now the criminal king of south Boston, but that wasn’t enough for him. In the mid-1970s, in circumstances that remain contested, Bulger had begun working as an FBI informant, but even managed to turn this situation to his advantage. Easily outwitting his handlers, he used the FBI to take out the Patricia family, the most powerful mob outfit in the city. Their demise left Whitey free to do as he pleased.

By the mid-1980s, he and his gang ran much of the loan-sharking, extortion, bookmaking and arms trafficking in eastern Massachusetts, and law enforcers were time and again frustrated in their efforts to stop them. What they didn’t know was that the Winter-Hill gang had informers within both the FBI and state police.

Bulger was ruthless in the extreme, and resorted to murder with alarming speed whenever his power was threatened or he caught even the faintest whiff of disloyalty. In one of Black Mass’s most chilling sequences, Jimmy Bulger is in a bar with his gang when one of his enforcers, Tommy King, has a mild disagreement with his boss and swears at him.

“Don’t worry about it,” Bulger says. But a week later he drives King out to a remote spot on the Neponset River and pretends to make peace with him before shooting him in the head. Time and again Bulger would settle disputes and potential security leaks with a bullet.

Meanwhile, his younger brother William Michael ‘Billy’ Bulger was riding high in Boston’s political elite as President of the Massachusetts State Senate. Billy would hold that lofty office for almost 20 years, and was only forced to retire from public life in 2003 when his association with one of America’s most notorious felons made his career untenable.

Whitey became a folk hero to many ‘southies’, meanwhile, who saw him as a salt-of-the-earth Irish-American. He was passionately loyal to south Boston, but also an Irish patriot who began donating money and guns to the IRA as early as the mid-1970s. After meeting IRA chief of staff Joe Cahill, Whitey raised a million dollars for the Provos by shaking down drug dealers in south Boston and Charlestown. He would later be involved in the botched attempt to smuggle a large cache of arms into Ireland aboard the ships Valhalla and Marita Ann.

He seemed invulnerable, but no one ever is. In 1994 the Drug Enforcement Administration, the state police and Boston PD began building a federal case against him for gambling and racketeering without telling the FBI, which they now realised was compromised. But Whitey’s informer John Connolly got wind of it at the last minute, and had time to warn Bulger before he was arrested. He disappeared, and would spend the next 16 years wandering America and living under assumed names.

He became the bogeyman, and supposed sightings of him were commonplace, especially after he was featured on the TV show America’s Most Wanted. But that show served its purpose, and the FBI would later admit that Bulger’s capture was a “direct result” of this media campaign.

A 2007 sighting of Bulger and his long-time girlfriend, Catherine Greig in the Sicilian holiday town of Taormina proved false. Bulger is a book lover, and in 2010 FBI agents visited a series of book stores in Victoria, British Columbia acting on a lead that turned out to be a dead end. They focused on Catherine Greig, a known animal lover with a weakness for beauty parlours, but that avenue also proved fruitless.

In the end, a priceless lead arrived from nowhere, thanks to a tip from a women in Iceland. She would later be identified by The Boston Globe as Anna Bjornsdottir, a former model who’d lived in Santa Monica and realised that the elderly gent with the east coast accent in her neighbourhood was Bulger. A day later the FBI struck, and arrested both Whitey and Catherine Greig. She was later convicted of harbouring a fugitive and identity fraud, and sentenced to eight years in jail, but the case against Bulger was more vexed.

For a start, he was wanted in three states, two of which have the death penalty. But to the surprise of many, Whitey cooperated, chatting freely about his life as a fugitive, and told his captors how he’d once visited his old haunt, Alcatraz, and had a tourist photo taken wearing a striped suit and standing behind mock prison bars.

Now the bars are real: in 2013 Whitey was given two life sentences, and will end his days in a Florida Penitentiary.

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