Whitey Bulger: How a man from Boston became one of the most notorious gangsters in history

He was serving time for his involvement in 11 murders when he died 

Chelsea Ritschel
Tuesday 30 October 2018 20:08 GMT
Whitey Bulger: Infamous Boston gangster killed in West Virginia jail aged 89

When James Joseph Bulger Jr was born on September 3 1929, it would have been hard to predict that he would grow up to become a dangerous organised crime boss.

Bulger, now more commonly known as “Whitey” Bulger, was born and raised in Dorchester, Massachusetts by his father and mother, an Irish immigrant.

During an early life rife with poverty, the eldest Bulger child of six was drawn to a life on the wrong side of the tracks in Boston, Massachusetts.

He was arrested for the first time at the age of 14 for larceny, at which point he’d already joined a local gang.

It was during his early days of petty crime that Bulger was given his nickname, by the local police for the colour of his hair.

Despite a brief stint in the US Air Force in 1948, Bulger was committed to a life of criminal activity - evidenced by his continued issues within the military and his multiple stints in military prison.

By 1952, Bulger had received an honourable discharge but found himself in federal prison four years later for charges related to armed robbery and hijacking.

While serving what was meant to be a 25-year sentence, Bulger spent time in Atlanta, Alcatraz and Leavenworth.

He was released after nine years and, by the late 1970s, had become a prominent figure in Boston’s organised crime scene.

Renowned Boston mobster, Whitey Bulger

Following his time in prison, Bulger had returned to Massachusetts where he began a relationship with Lindsey Cyr and began to work as an enforcer for crime boss Donald Killleen.

Bulger fathered a child with Cyr, Douglas Glenn Cyr, in 1967. Their son later died in 1973 from Reye’s Syndrome and the couple eventually split up after a 12-year common-law marriage.

After Killleen was killed in his line of work, Bulger joined his second gang - the Winter Hill Gang. In just a few short years, he rose through the ranks and assumed the position of boss of the gang by 1979.

During his infamous years leading the Winter Hill Gang, Bulger assumed all gang-related responsibilities - including calling for multiple murders and controlling a significant portion of Boston’s drug deals, illegal gambling and arms dealing.

However, at the same time, Bulger also became a key FBI informant, in part responsible for taking down the Patriarcas, a rival New England crime family - which ultimately allowed him to grow his own gang further.

To tip off the FBI, Bulger used his family ties - as his brother William was a member of the Massachusetts State Senate, and the corrupt police forces in South Boston at the time.

After successfully evading police capture in 1995 for charges related to illegal gambling, Bugler was added to the list of the FBI’s 10 most-wanted fugitives in 1999 and a $2m reward was offered for any information that led to his arrest.

At the time, he was considered a mark of national embarrassment for the FBI as it was reported the agency had accepted bribes and offered protection to the gangster.

However, Bulger’s life story also made for a highly entertaining film narrative, first appearing in 2006 Martin Scorsese movie, The Departed, and later, in a 2015 movie Black Mass starring Johnny Depp.

Bulger managed to stay on the run for 16 years before being captured in June 2011 in Santa Monica, California.

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At the time, he was 81 years old and living in a rent-controlled apartment with his long-term girlfriend, Catherine Greig.

For her involvement in harbouring a fugitive, Greig was sentenced to eight years in prison.

As for Bulger, his own life on the run ended with a trial beginning in June 2013.

After a two-month trial, the notorious criminal was found guilty on 31 counts including federal racketeering, extortion, conspiracy, and participating in 11 murders.

The court sentenced James "Whitey" Bulger to two life sentences plus five years in November 2013, which he served until October 30 2018 - when the former mob boss was found dead in jail at the age of 89.

He had just been moved to a prison in West Virginia.

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Following his death, the US attorney for the Northern District of West Virginia said: “The FBI will be conducting an investigation into the death of James Bulger. No other information will be released at this time.”

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