James ‘Whitey’ Bulger: Notorious Boston gangster jailed for murders after years of evading justice

The mobster headed a racketeering and drug-dealing operation for three decades and once spent 16 years on the run before the FBI caught up with him

Bulger had a stash of 30 guns and $822,000 in cash hidden in the walls of his California apartment when arrested in 2011 (AP)

James “Whitey” Bulger was the Boston mob boss who corrupted FBI agents, tortured and killed his associates, and spent 16 years on the run.

He died at the age of 89 while serving a double life sentence at the high-security US Penitentiary Hazelton in West Virginia.

Bulger headed a racketeering and drug-dealing operation for 30 years while his younger brother, William, was president of the Massachusetts Senate.

Nicknamed “Whitey”, Bulger disappeared in 1995 after learning from a former FBI agent, John J Connolly Jr, that an indictment was pending, triggering an international manhunt.

He was finally captured on 22 June 2011, when a tipoff from a former neighbour led FBI agents to an apartment in Santa Monica, California, where Bulger and his girlfriend, Catherine Greig, had been living under the names Charlie and Carol Gasko.

Bulger had a stash of 30 guns and $822,000 in cash hidden in the walls.

Bulger in 1984: the Boston gangster is said to have taken pleasure in his killings (AP)

“Do what you want with me,” Bulger told the judge when he decided not to testify in his own defence – the court had barred him from telling jurors his claim that a former federal prosecutor had given him immunity beginning in the 1970s.

Bulger called the trial a sham and was appealing his conviction.

During his two-month hearing in 2013, Bulger’s former crime partners testified he took pleasure in killing his victims and sometimes took a nap while his underlings dug graves.

James Bulger grew up in Boston and had five siblings (AP)

His lawyers attacked the veracity of FBI files allegedly documenting Bulger’s years as a criminal informant on Italian organised crime in America.

His defence team claimed he purchased information from law-enforcement officials, and was never an informant.

According to Dick Lehr, co-author of Whitey: The Life of America’s Most Notorious Mob Boss, writing in the Boston Globe newspaper, he sought “to soft-pedal his monstrosity by assuming the mask of a tough guy but not such a bad guy”.

“I never, never, never cracked,” Bulger said in the 2014 film Whitey: United States of America v James J Bulger.

Bulger was convicted of racketeering and the murder of 11 people. Some of his victims, mostly former associates whom he feared were cooperating with police, were missing for decades until his crime partners led law enforcement to secret graves as part of plea agreements. Bulger was acquitted of seven murders.

At his sentencing in November 2013, Bulger refused to look at the children of his victims as they took to the podium one by one and described the pain of their losses.

“The scope, the callousness, the depravity of your crimes is almost unfathomable,” US district court judge Denise Casper told Bulger.

Connolly was convicted of racketeering and received a 40-year sentence for murder. His girlfriend Greig, a former dental hygienist, pleaded guilty without a plea agreement and was sentenced to eight years for harbouring a fugitive and identity fraud.

James Joseph Bulger Jr was born in 1929, in the Dorchester neighbourhood of Boston. He was one of six children born to James Joseph Bulger Sr and Jane Veronica McCarthy, a first-generation Irish American who was known as Jean. His father, who was from Newfoundland, lost his left arm as a young labourer when he was pinned between two trains while working in a Boston rail yard.

Raised mostly in public housing in the city’s South Boston district, Bulger graduated from a trade school and served in the US air force. He went AWOL but received an honourable discharge in 1952 before embarking on a life of crime.

The gangster shortly after his arrest in 2011

Dubbed “Whitey” as a boy because of his white-blond hair, Bulger loathed the nickname and insisted his associates call him Jim. His experience with crime as a juvenile escalated to bank robberies in the 1950s that eventually landed him in Alcatraz.

“I had seen him change from a blithe spirit to a rebel whose cause I could never discern,” his brother William wrote in While the Music Lasts: My Life in Politics (1996). “He was in a constant state of revolt against – I’m not sure what. He was restless as a claustrophobic in a dark closet.”

By 1956, Bulger was sentenced to more than 20 years in federal prison for bank robbery. He was released after nine years, including that stint in Alcatraz.

While in federal prison in Atlanta in 1957, Bulger voluntarily participated in medical experiments involving LSD to get reduced prison time. The programme was later exposed as part of the CIA’s research into mind control, known under the code name MK-ULTRA.

In diaries recovered by the FBI, Bulger wrote that he suffered terrible side effects from the LSD experiments and was never able to sleep well again.

“I was in prison for committing a crime and feel they committed a worse crime on me,” Bulger wrote.

Bulger never married. A woman named Lindsey Cyr said she and Bulger had a 12-year relationship beginning in 1966 that produced a son, Douglas, who was born in 1967. The boy died in 1973 from a rare medical condition.

Cyr, a former waitress, said Bulger was at the hospital the night their son died and was devastated.

“My life was wasted and spent foolishly, brought shame and suffering on my parents and siblings and will end soon,” he wrote in a letter to three girls from Apponequet Regional High School in Lakeville, Massachusetts, who had contacted him for a history project, the Boston Globe reported in June 2015.

“If you want to make crime pay – go to law school,” he wrote.

James Joseph “Whitey” Bulger Jr, Boston mob boss, born 3 September 1929, died 30 October 2018

© Bloomberg