11 surprising facts about Irish American gangster James 'Whitey' Bulger

11 surprising facts about Irish American gangster James 'Whitey' Bulger

JAMES 'WHITEY' Bulger earned a reputation as one of Boston's most notorious crime lords through a deadly mix of cunning, violence and intimidation.

Over the course of more than four decades, Whitey was involved in a string of illegal activities that ran the gamut from drug trafficking and racketeering to assault and murder.

When his criminal endeavours began to catch up with  him, Bulger spent a further 16 years from 1994 to 2011 evading capture before his arrest in California following a tip-off to the FBI.

Convicted two years later for his role in 11 murders and various other crimes, Bulger's rap sheet would have extended even further, but prosecutors were unable to prove the crimes in court.

Bulger was no ordinary crime lord either, leading a double life as one of America's most wanted men while also serving as an informant to the FBI for three decades.

It was a duplicitous existence that eventually caught up with him, aged 89, when he was violently killed while serving out his days in prison.

Here are 11 facts about Irish American gangster James 'Whitey' Bulger.

11. Bulger served in the military

Bulger spent four years in the US Air Force as an aircraft mechanic. He even earned a high school diploma during his time in the forces. He was never far from trouble though. During his four-year stint in the forces, Bulger was arrested after going AWOL and was also arrested by police on rape charges.

Whitey was never convicted on either charge and eventually left the military in 1952 after being honourably discharged.

10. Whitey loved Alcatraz

Bulger first spent time behind bars back in 1956, when he was sentenced for armed robbery and hijacking a truck. Three years later a foiled prison escape plan saw him moved to Alcatraz Island where he would stay for another three years. Bulger would later reflect: "'If I could choose my epitaph on my tombstone, it would be 'I'd rather be in Alcatraz.' '"

His love of Alcatraz saw him read countless books on the topic while at some point in the 1990s, Bulger and his girlfriend visited the prison island as tourists, while on the run and posed for photos dressed in mock prison outfits.

Two Federal Bureau of Investigation (FBI) artist composite images of fugitive James "Whitey" Bulger.

9. He hated the nickname Whitey

Bulger despised his nickname Whitey, which was a reference to his pale complexion and white-blond hair. While he preferred to go by his given name, Jim, Whitey was also happy with the moniker Boots, which apparently referred to his love of cowboy boots.

8. The CIA conducted experiments on Bulger

During his first stint in prison, Bulger volunteering to be a guinea pig for a drug test experiment conducted in an apparent attempt to find a cure for schizophrenia. Whitey was injected with LSD as part of the bizarre experiment and went on to suffer insomnia and nightmares for much of his life as a result.

He later learned the tests were actually conducted as part of a top-secret CIA program designed to develop a mind-control weapon.

7. Bulger suffered a personal tragedy

Bulger had one son, who was conceived with then-girlfriend Lindsey Cy in the 1960s. Though initially hesitant to accept the child was his own, Bulger eventually began to dote on the boy, christened Douglas, though he was careful to keep the child secret due to his many enemies.

But his joy was short-lived. In 1973, while Bulger was busy rising through the ranks of the Winter Hill Gang, Douglas was hospitalised with Reye’s Syndrome, following a severe reaction to aspirin. Bulger was at his bedside when Doulas died three days later.

6. A lookalike helped Bulger evade the authorities

While on the run, Bulger adopted a string of aliases with James Lawlor perhaps the most infamous of the bunch. Lawlor bore a striking resemblance to Bulger and was discovered by the crime boss living on the streets of Los Angeles.

Because of their striking similarity to one another, Bulger was able to use Lawlor’s driver’s license and other documents. As part of the deal, he paid for Lawlor to live in a rented apartment.

5. He was America's most wanted 

Following the death of al Qaeda leader Osama bin Laden in Pakistan in 2011, Bulger became the no.1 most wanted fugitive on the FBI’s 10 Most Wanted List.

His reign at the top of the list would only last a few short months.

4. Miss Iceland of 1974 was responsible for Bulger’s capture

Anna Bjornsdottir, who had acted on U.S. television under the name Anna Bjorn, had lived near Bulger in Santa Monica, California.

While back in Iceland, she saw a news report about the FBI hunt for Bulger. She recognised him as her quiet retiree neighbour knew from home and called the authorities. Bulger was subsequently arrested with Bjornsdottir claiming a $2 million reward.

This FBI Ten Most Wanted Fugitive poster shows reputed Boston mobster James "Whitey" Bulger. (Photo by FBI/Getty Images)

3. Police found a bizarre treasure trove of items in Whitey's apartment after his arrest

When Bulger and his girlfriend Catherine Greig were finally apprehended, police found an astonishing array of items in their Santa Monica apartment.

They included 30 different firearms, $822,198 in cash, 10 pairs of white trainers, 27 pairs of women’s sunglasses, a skull ring, a skull belt, various cat mugs, a 14-carat diamond Claddagh ring, books about the second world war, books about cowboys, books about Alcatraz a portrait of a poodle, two cat statuettes and a mug shaped like a beady-eyed rat.

There was also a punching-bag mannequin Bulger left by his window, so people would think someone was home, complete with a tan wide-brimmed hat. The items were later sold at auction.

2. Whitey was no Robin Hood

Bulger cultivated an image of himself as a Robin Hood character for the Irish community of Boston. The story went that he was a criminal that had his own code of conduct: he didn’t kill women, he didn’t deal drugs and he wasn’t a rat. None of which was true.

Bulger was convicted of killing one woman and accused of murdering another in gruesome circumstances. 26-year-old Deborah Davis was strangled to death and buried by Neponset River in Quincy. Whitey was accused of the murder and of ordering her teeth be removed to make identification harder, but the jury issued a “no finding” verdict in her case.

1. Bulger hated Johnny Depp’s performance in Black Mass

Though Jack Nicholson’s character, Frank Costello, from Martin Scorsese’s The Departed was inspired by Bulger, Johnny Depp is so far the only actor to play Whitey in the film Black Mass.

Depp wore heavy prosthetics, stained teeth and adopted a Boston accent for the role which earned critical praise despite the film’s other shortcomings. Bulger was not impressed. He did not meet with Depp to consult the role and let his feelings be known through his lawyer Hank Brennan, who compared the actor’s performance to his work in Alice in Wonderland.

"Johnny Depp might as well have been playing the Mad Hatter all over again as far as James Bulger is concerned," Brennan said. "Hollywood greed is behind the rush to portray my client, and the movie missed the real scourge created in my client’s case, the real menace to Boston during that time and in other mob cases around the country – the federal government’s complicity in each and every one of those murders with the top echelon informant program."