James “Whitey” Bulger, the leader of the Boston Mafia, is remembered as a charismatic and ruthless leader whose name was linked to 19 murders and countless gruesome events in which victims were tortured, tied up in heavy chains, shot and buried in cellars, with their teeth were removed to prevent identification.
He also famously set fire to John F Kennedy’s Brookline birthplace and enjoyed taking cat naps after shooting people in the head.
Once the head of South Boston’s Winter Hill Gang, Bulger’s mark on American organized crime is as pronounced as the stain he left on the FBI’s reputation when he evaded prosecution for decades and sixteen topped the Most Wanted list for years. his arrest in 2011.
During Bulger’s 2013 trial, it emerged that he had served as an FBI informant as far back as 1975, although he has always denied this. The deal gave Bulger virtual impunity for decades to commit any crime he wanted, except murder.
Bulger was ultimately convicted of murdering at least eleven people in 2013 and was serving two life sentences at the time of his death.
Bulger was born in September 1929, about four miles north of Boston, in the town of Everett. He was the eldest of six children in an Irish-American family.
His father, James Sr., worked as a dock worker but became unemployed after losing an arm in an accident. Because of the poverty that followed, the family moved when Bulger was eight years old to a public housing project in the tough South Boston neighborhood.
But while his siblings studied hard and did well in school, Bulger began to deviate from the straight and narrow from an early age. By the time he reached his teens, he already had a reputation as a street fighter and thief.
Unsurprisingly, he had also come to the attention of the local police officers, who nicknamed him ‘Whitey’ because of his distinctive blond hair.
Bulger is seen in a pair of undated mugshots released by the FBI
At the age of 14, he was arrested for the first time for theft. By now he was a member of a street gang called ‘the Shamrocks’ and convictions for assault, theft, extortion and forgery soon followed.
The stints in juvenile detention did not stop him from becoming a one-man crime spree. 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 first in Kansas and then in Idaho. But he ended up in military prison for a number of assaults and was arrested for leaving without leave at one point.
However, he managed to leave the armed forces with an honorable discharge 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 federal prison for the first time after being convicted of armed robbery and hijacking.
According to some reports, he was among the prisoners given LSD and other drugs as part of a CIA research program into mind control drugs.
What is certain is that he was such a troublesome inmate that he was eventually transferred to Alcatraz, the infamous maximum security prison in San Francisco Bay, as one of the last batch of prison birds sent there before the prison was closed in 1963. Closed.
After spending time in two other institutions, Bulger finally became a free man in 1965 after nine years in custody. Unlike many criminals, he never boasted about his incarceration.
“For him,” said William Chase, an FBI agent who pursued Bulger for years, “the prison sentence was proof of failure.” Back on the streets, he was determined to do two things: stay out of prison and establish a criminal empire.
Although he initially took jobs as a janitor and construction worker, Bulger soon became involved in bookmaking, debt collection, and acting as an underworld enforcer.
It wasn’t long before he took over a small operation called the Winter Hill Gang and turned it into Boston’s most ruthlessly efficient crime syndicate.
The main areas of activity were drug trafficking, 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 he not spend lazy afternoons over long lunches at neighborhood restaurants, Bulger didn’t seem to have any vices. He didn’t drink, didn’t smoke, never used credit cards and didn’t even gamble.
The little time he spent away from his nefarious business was largely spent on bodybuilding and reading. He was always interested in history, especially anything related to Adolf Hitler.
Much of his energy also went into efforts to become a master of disguise. He dyed his hair different colors and wore different types of glasses, although most observers agree that he found it impossible to mask his thick Boston accent.
Another thing Bulger had a hard time hiding was his volcanic temper. Even in apparently casual conversations, he was prone to explosive outbursts.
Meanwhile, his propensity for extreme violence shocked 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 hit people with clubs. He shot people. Strangled people. Run them over with cars. After he killed someone, it felt like a stress relief, you know? He would be nice and quiet for a few weeks. As if he’s just gotten rid of all his stress.’
Given the blatant criminality, it wasn’t long before questions were asked about how he got away with it.
The answer was a long time coming, and when it did it was shocking: Bulger had been operating as an FBI informant since the mid-1970s.
From his perspective, it was a perfect arrangement. He tipped off his agency handler and childhood friend, John Connolly, about other criminal activity in Boston in exchange for allowing him to continue his own activities unhindered. The information he passed on virtually destroyed the mafia’s presence in the city.
It wasn’t until the 1990s that Boston police and the Drug Enforcement Agency, angry at the FBI’s inaction, launched their own investigations.
After Connolly – who later received a 10-year prison sentence for obstruction of justice – was alerted that authorities were on his trail, Bulger disappeared on December 23, 1994.
During his years on the run with girlfriend Catherine Grieg, several sightings were reported from locations as diverse as New Zealand, Canada, Italy, and along the U.S.-Mexico border.
He and Grieg ended up in Santa Monica, California, where they posed as married retirees from Chicago.
After al-Qaeda leader Osama bin Laden was killed by U.S. forces in Pakistan in 2011, Bulger replaced him as the No. 1 wanted fugitive on the FBI’s “Ten Most Wanted” list.
One of the many aliases Bulger used while on the run was that of James Lawlor, a man Bulger found on the street in the Los Angeles area.
The two men looked so much alike that Bulger was able to use Lawlor’s driver’s license and other identification documents. 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, posing as a retired Chicago couple in Santa Monica.
Playing a crucial role in Bulger’s arrest were Miss Iceland of 1974, Anna Bjornsdottir, who lived next door, and Grieg in Santa Monica.
During her visit to 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 police raided his Santa Monica apartment, they found several fiction and nonfiction books about criminals, including “Escape From Alcatraz.”
Police also found about $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.
At his 2013 trial, Bulger was convicted of eleven murders, including the strangulation of a woman. Jurors were unable to reach a verdict on the accusation that he strangled a second woman. A witness said Bulger insisted that the women’s teeth be extracted to conceal their identities.
Bulger refused to testify at his trial, claiming he had been given immunity from prosecution by federal agents.
He adamantly 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 pieces of evidence, produced chilling testimonies worthy of a pulp novel.
Harrowing stories were heard of teeth being pulled from the mouths of murder victims to thwart the identification and strangulation of the girlfriend of a gangster who ‘knew too much’.
In June 2013, Bulger was tried on 32 counts of racketeering, including allegations that he was complicit in 19 murders.
The two-month hearing, which included testimony from more than seventy witnesses, resulted in his conviction for eleven of the murders.
It also heard evidence that Bulger supplied the weapons and ammunition used in the 1984 escape from the IRA’s Marita-Ann, which resulted in a 10-year prison sentence for current Sinn Féin TD Martin Ferris.
Sentencing him to two life sentences plus five years, the judge told Bulger he had been involved in “unfathomable” crimes that caused “agonizing” suffering for his victims.
Five years into his sentence, Bulger had just been transferred to USP Hazelton, a maximum security prison, when he was found dead on the night of October 30, 2018.
A prison source said the wheelchair-bound Bulger was among the general population when three inmates rolled him to a corner, out of view of surveillance cameras, hit him in the head with a sock lock and tried to gouge his eyes out with a shiv. .
The source said he had not even been treated at the West Virginia facility when he was killed. But someone who knew he was being transferred made it known: the killer had to know he was coming.