HE was one of America’s most feared crime lords, a mob boss who had been on the FBI’s “Ten Most Wanted” list since 1999 and a man whose infiltration of America’s top crime-fighting agency would inspire a Hollywood blockbuster.
In the end, however, it appears that James “Whitey” Bulger, 81, was not ratted out by a crony or rival.
Even the $2 million bounty offered for his capture – the largest on record for a domestic American fugitive – may not have been a factor.
In the end, it seems, he was finally undone by his moll’s penchant for teeth-whitening treatments and facials.
Bulger was arrested in Santa Monica on Wednesday, after an FBI media campaign targeting women chat-show viewers in their 60s.
The aim had been to locate Catherine Greig, a 60-year-old former dental hygienist who was Bulger’s long-term girlfriend.
The adverts described her as an animal lover with “well-kept” teeth and a fondness for plastic surgery and beauty salons.
The hope was that another beauty parlour customer would recognise her.
The plan seems to have worked.
A tip-off led detectives to an apartment in Santa Monica and ended the freedom of a man whose life story directly inspired the writers who created the gangster boss played by Jack Nicholson in the Oscar-winning film The Departed.
Of Irish-American descent, Bulger was born into poverty in the projects of South Boston in 1929.
He was arrested for the first time, for larceny, at the age of 14, before graduating to assault, battery and armed robbery while associated with the Shamrocks street gang.
In 1952 he helped to hijack a liquor truck. By 1955 he was robbing banks.
During his first stint in a federal prison, from 1956 to 1959, he is said to have been part of a CIA program researching mind-control drugs.
One account suggests that he was given LSD and suffered insomnia and nightmares ever since.
In the late 1970s he took control of the Winter Hill Gang, the most feared Irish crime syndicate on the East Coast.
His criminal career would earn him tens of millions of dollars, along with a reputation for hideous cruelty.
Rivals, and even young girlfriends, would be found dead and horribly mutilated.
Bulger was wanted for his alleged role in 19 murders.
He was also linked the theft of 13 paintings from the Isabella Stewart Gardner Museum in Boston by thieves dressed as policemen in 1990, in one of the biggest unsolved art heists on record.
The stolen canvasses included Rembrandt’s only seascape, The Storm on the Sea of Galilee.
As Bulger climbed the underworld career ladder he came to the notice of the FBI, who recruited him as an informer under a controversial deal that allowed him to continue with his criminal activities.
It was a tip-off from an FBI handler that allowed him to flee in 1995.
The FBI agent, John Connolly, is now in prison for his role in the murder in 1982 of a businessman who was about to testify against Bulger. In 2000 the FBI’s Boston branch created a unit tasked with the sole objective of finding Bulger.
Until this week, the last confirmed sighting was in London in the 1990s, by a businessman who saw him working out in the gym of the Meridien Hotel in Piccadilly Circus.
A safe-deposit box was later uncovered in London containing $50,000 and the key to another deposit box in Dublin, where Bulger had connections with the republican movement.
For decades, he had salted away cash and fake passports across Europe and America, perhaps anticipating that he would spend his twilight years on the run.
The Pakistani Ambassador to the US recently referred to the Boston gangster while defending his country’s failure to find another fugitive.
“If Whitey Bulger can live undetected by American police for so long, why can’t Osama bin Laden live undetected by Pakistani authorities?” he asked.
In May Time magazine published a long profile on him. “In South Boston, Bulger still casts a long shadow. Locals don’t talk to strangers about him, so at home his infamy is his best protection against ever being caught,” it said.
Over the years, those hunting him had built up a detailed portrait. He was an avid reader, a history buff with a special interest in Adolf Hitler. He had a bullying manner that he struggled to tame even in casual conversation, and an explosive temper.
He was known to dye his hair, sport a moustache and to alternate between different styles of glasses. He loved dogs, never used credit cards and spoke in a thick Boston accent that he probably could not disguise if he tried.
Completing a life story that reads like a Mario Puzo novel was the younger brother who chose a different, more righteous path.
William M. Bulger was one of the most powerful politicians in Massachusetts, leading the state senate for 17 years and later serving as president of the University of Massachusetts for seven years. In 2003 he resigned from his university post under pressure from the Governor, Mitt Romney.
His resignation came two months after he testified about his brother before a congressional committee. William Bulger said that he spoke to his brother shortly after he went on the run, but did not alert the authorities.