Boston mob kingpin James & # 39; Whitey & # 39; Bulger is remembered as a charismatic and ruthless leader whose name was linked to 19 murders and countless horrific events in which victims were tortured, bound in heavy chains, shot and buried in cellars with their teeth removed to prevent identification.
He also famously set fire to John F Kennedy's Brookline birthplace and enjoyed taking naps after shooting at people in the head.
Once the head of & # 39; Winter Hill Gang & # 39; in South Boston, Bulger & # 39; s stamp on American organized crime is just as pronounced as the stain he left on the FBI's reputation as he escaped decades and 16 years earlier on the list of most wanted people was his arrest in 2011.
The Bulger trial in 2013 showed that he had already served as an FBI informant in 1975, although he has always denied this. The deal gave Bulger virtual impunity to commit any crime he wanted for decades – except murder.
Bulger was eventually convicted of killing at least 11 people in 2013 and served two life sentences at the time of his death.
Bulger was born in September 1929 about four miles north of Boston in the city of Everett. He was the eldest of six children in an Irish-American family.
His father, James Sr., worked as a dock worker, but found that he was unemployed after losing an arm in an accident. Due to the poverty that followed, the family moved to a social housing project in the difficult neighborhood of South Boston when Bulger was eight years old.
But while his siblings were studying hard and doing well at school, Bulger began to deviate from the right path at a young age. By the time he reached his teens, he already had a reputation as a street fighter and thief.
Not surprisingly, he had also come to the attention of local police, who nicknamed him & # 39; Whitey & # 39; because of his characteristic blonde hair.
Bulger is seen in a few undated mugshots that have been released by the FBI
At the age of 14 he was first arrested for theft. In the meantime he was a member of a street gang that & # 39; de Klavers & # 39; and soon followed convictions for assault, theft, extortion and forgery.
Proverbs in juvenile prisons did not detract from him becoming a wave of one-man crime. Nor did he stop at the US Air Force, of which he became a member at the age of 18.
After his training as an aircraft engineer, he was first stationed in Kansas and then in Idaho. But he ended up in a military prison for a number of assaults and was arrested for absence without leave in one phase.
However, he managed to leave the armed forces with an honorable dismissal and returned to Boston. It was at this point that his burgeoning criminal career took a crucial turn.
In 1956, 25-year-old Bulger was sent to a federal prison for the first time after being convicted of armed robbery and hijacking.
According to some reports, he was one of the prisoners who received LSD and other substances as part of a CIA research program into drugs for mind control.
What is certain is that he was such a tricky prisoner that he was eventually transferred to Alcatraz, the notorious maximum security prison in San Francisco Bay, as one of the last group of jailbirds sent there before it was sent in 1963 closed.
After spending time in two other institutions, Bulger finally came up in 1965 as a free man after nine years in custody. Unlike many criminals, he never boasted about his imprisonment.
& # 39; For him, & # 39; said William Chase, an FBI agent who had been haunting Bulger for years, & # 39; imprisonment was proof of failure. & # 39; Back on the street, he was determined to do two things: stay out of jail and establish a criminal empire.
Although he first took on jobs as a janitor and construction worker, Bulger soon became involved in making books, collecting debts and acting as a enforcer in the underworld.
It wasn't long before he managed to take over a small operation, the Winter Hill Gang, and turn it into Boston & # 39; s most ruthlessly efficient crime syndicate.
The main activities were drug use, gambling and prostitution. Bulger based his modus operandi on the mafia, which controlled the northern suburbs of the city.
But unlike some of his Italian counterparts, he was extremely disciplined.
Not only did Bulger not have lazy afternoons during long lunches in neighborhood restaurants, but he seemed to have no vices. He didn't drink, didn't smoke, never used credit cards, didn't even gamble.
The little time he spent on his nefarious enterprise was largely devoted to bodybuilding and reading. He has always been interested in history, especially everything that had to do with Adolf Hitler.
Much of his energy also went into trying to become a master of disguise. He dyed his hair in different colors and wore different styles of glasses, although most observers agreed that he found it impossible to mask his thick Boston accent.
Another thing Bulger had trouble hiding was his volcanic mood. Even in seemingly informal conversations, he was sensitive to explosive outbursts.
Meanwhile, his tendency toward extreme violence shocked hardened criminals and the police. Rivals and enemies were brutally murdered, either by Bulger himself or by order of him.
His former right-hand man Kevin Weeks said later: & He stabbed people. He hit people with bats. He shot people. Strangled people. Run over them with cars & # 39; s. After he killed someone, it was like relieving stress, you know? He would be nice and calm for a few weeks. As if he has just lost all his stress. & # 39;
Given this brutal crime, it wasn't long before questions were asked about how he could get away with it.
The answer came long and it was shocking: Bulger had been active as an FBI informant since the mid-1970s.
From his perspective it was a perfect setup. He gave his desk handler and childhood friend John Connolly a tip about other criminal activities in Boston in exchange for being allowed to continue his own activities unhindered. The information he has provided has virtually eliminated the presence of Mafia in the city.
It was in the 1990s before the Boston police and the Drug Enforcement Agency, furious with the FBI's failure, started their own investigation.
Bulger disappeared on December 23, 1994, after being tipped by Connolly – who was later imprisoned for ten years for obstructing the law – that the authorities realized.
During his years on the run with girlfriend Catherine Grieg, various sightings were reported from locations as diverse as New Zealand, Canada, Italy and along the American Mexican border.
He and Grieg ended up in Santa Monica, California, where they pretended to be married retirees from Chicago.
After Al Qaeda leader Osama bin Laden was killed by US troops in Pakistan in 2011, Bulger succeeded him as No. 1 refugee wanted on the & # 39; Ten Most Wanted & # 39; from the FBI.
One of the many aliases that Bulger used while fleeing was that of James Lawlor, a man who found Bulger on the street in the Los Angeles area.
The two men looked so much alike that Bulger could use Lawlor's driver's license and other identity papers. In return, he paid Lawlor's rent, according to the Boston Globe.
Catherine Greig and Whitey Bulger are seen in June 1998. They were on the run for 16 years and posed as a retired couple from Chicago in Santa Monica
A crucial role in Bulger's conquest was Miss Iceland of 1974, Anna Bjornsdottir, who lived near him and Grieg in Santa Monica.
While visiting Iceland, the actress who worked under the name Anna Bjorn saw a news report about the authorities' hunt for Bulger.
She recognized him as the quiet retiree she knew from her neighborhood and called the FBI, who arrested him in June 2011. Bjornsdottir later claimed a $ 2 million reward.
When the police raided his apartment in Santa Monica, they found several fiction and non-fiction books about criminals, including & # 39; Escape From Alcatraz & # 39 ;.
The police also found around $ 800,000 in cash and an arsenal of weapons in the modest apartment where Bulger and Greig had lived for years as Charles and Carol Gasko.
In his trial in 2013, Bulger was convicted of 11 murders, including the strangulation of a woman. Jury members were unable to pass judgment on charges of strangling a second wife. A witness said that Bulger insisted on having the teeth of the women pulled to hide their identities.
Bulger refused to testify during his trial that he had received immunity from prosecution by federal agents.
He firmly denied being an FBI informant, but close ties between some FBI agents in Boston and Bulger's Winter Hill Gang in the 1970s and 1980s are well documented.
Former FBI agent John Connolly was sentenced to prison after being convicted in 2002 of actually joining the gang.
His trial, with 72 witnesses and 840 exhibitions, delivered a hair-raising testimony worthy of a poem novel.
It heard shocking tooth stories from the mouth of murder victims to prevent identification and the strangulation of the girlfriend of a gangster who & # 39; knew too much & # 39 ;.
In June 2013, Bulger was tried for 32 counts of racketeering, including allegations that he was an accessory to 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 weapons and ammunition used in the Iita Marita-Ann shooting in 1984, resulting in the current Sinn Féin TD Martin Ferris who was imprisoned for ten years.
The judge sentenced him to two sentences of life plus five years and told Bulger that he had been involved in & # 39; inscrutable & # 39; crimes involving the suffering of its victims & # 39; painful & # 39; used to be.
Five years after his sentence, Bulger had just been transferred to USP Hazelton, a heavily guarded prison, when he was found dead on October 30, 2018.
A prison source said Bulger was wheelchair-bound in the general population when three prisoners rolled him to a corner, out of sight of surveillance cameras, slapped him in the head with a lock in a sock, and tried to stick his eyes out with a shiv.
The source said he was not even processed at the West Virginia facility when he was killed. But someone who knew he was being transferred connected the word – the murderer had to know he was coming.
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