Incredible Facts About Whitey Bulger: One Of The Most Notorious Gangsters In US History

James Joseph “Whitey” Bulger Jr. was an Irish-American crime boss and head of the Winter Hill Gang in Boston, Massachusetts. He was at large from the 1970s until the mid-1990s, where he went into hiding while evading conviction. After fleeing Boston in 1995, Bulger was placed on the FBI’s “Ten Most Wanted Fugitives” list until his capture in 2011. He was found guilty of federal racketeering, extortion, conspiracy, and the murder of 11 individuals with the judge claiming that the “scope, callousness and depravity of your crimes are almost unfathomable.” Now, let’s take a look at some of the lesser-known facts about Whitey Bulger’s dedication to a life of crime.

Learn what was so shocking about his connection with the FBI

He Was Found Dead In Prison In October 2018

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On Monday, October 29, 2018, James “Whitey” Bulger was transferred from Oklahoma to United States Penitentiary, Hazelton in West Virginia. The next morning, he was found dead at 8:20 AM inside the prison.

According to a spokesperson for the US attorney for the Northern District of West Virginia, the FBI will be conducting an investigation into his death. Although no further information has been released at this time, it has been assumed that his death was the result of a murder.

His Only Known Son Died At The Age Of 6


In 1966, Bulger and his girlfriend Lindsey Cyr had only been dating for a few months before she became pregnant. Bulger was not thrilled about the pregnancy, so Cyr had her ex-boyfriend named as the father on the birth certificate. In 2010, Cyr told the Boston Globe that Bulger kept his son a secret to protect him from his father’s many enemies.

After the boy became ill due to a severe reaction to aspirin, Bulger sat by his bed for three days until he passed. Bulger was reportedly “out of his mind” after his death.

He Was An FBI Informant

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Even before becoming the boss of the Winter Hill Gang, unbeknownst to his even his closest associates, he was working as an FBI informant. Bulger took advantage of his brother William’s position in the Massachusettes State Senate and childhood friends in the police force in order to help bring down the Patriarcas, a New England crime family.

By doing this, not only did it put him on good terms with the FBI, but it also helped him build an even more powerful crime network of his own.

He enjoyed a prison that everyone else feared.

He Hated His Nickname “Whitey”

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While most well-known and feared mobsters have some sort of nickname, it turns out that Bulger hated that “Whitey” was his. The name was given to him as a reference to his white-blonde hair that he had as a child, something he didn’t exactly take pride in.

He preferred to be called by his real name, Jim, although he didn’t mind his other nickname “Boots,” which came about for his love to wear cowboy boots.

He Volunteered For LSD Testing In Prison

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While imprisoned in Atlanta for a bank robbery conviction in 1957, Bulger volunteered to be a drug test subject for the psychedelic substance LSD for a reduced prison sentence. In a so-called effort to find a cure for schizophrenia, doctors began testing LSD on prisoners, a substance not very well known at the time.

After being injected with the drug, Bulger later claimed that he experienced insomnia and nightmares as a result of the of the experiment.

He Was Honorably Discharged From The Military

In his youth, Bulger served nearly four years in the United States Air Force where he worked as an aircraft mechanic and earned his high school diploma. Although this was well before he became the crime boss that gained him notoriety, he was never far away from trouble.

During his service, the young Bulger was arrested for going AWOL and arrested again for rape charges. However, he was never convicted or sentenced on either charge and received an honorable discharge in 1952.

He Actually Liked Alcatraz

While already in prison for armed robbery, Bulger was sent to the no longer functioning Alcatraz Island off San Francisco in 1959 after allegedly planning a prison escape in Atlanta.

After his capture in 2011, Bulger discussed to an author and historian about his fond memories on “the rock.” He claimed that “If I could choose my epitaph on my tombstone, it would be ‘I’d rather be in Alcatraz.” He even visited the prison again as a tourist while on the run!

What they found inside of his apartment proved that he was indeed Whitey Bulger.

His Old Apartment Was Put Up For Rent

While on the run from the authorities, Bulger and his girlfriend Catherine Greig lived as Charlie and Carol Gasko in a seaside apartment in Santa Monica, California. Bulger even described his time in California as a “16-year honeymoon.” The couple’s neighbors described them as being quiet and polite and would even help them with their groceries from time to time.

After Bulger’s arrest in 2011, his apartment was put up for rent in 2014. Must be interesting to live where one of the most wanted men in America did for some time.

He Was Lured By His Landlord Into Being Captured

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Bulger’s life on the run came to an end in 2011, where he was caught in Santa Monica after being in hiding for 16 years. A tipster informed the FBI that he was living with his girlfriend in an apartment complex under the alias of Gasko and pretending to be retirees.

The FBI convinced the building manager to lure Bulger into the garage of the apartment, telling him that the lock on his storage had been broken. In the garage, he was surrounded by the FBI and apprehended, eventually proclaiming “You know who I am; I’m Whitey Bulger.”

What They Found Inside His Apartment Was Shocking


The couple lived on the third floor of a 28-unit building of one and two-bedroom rooms close to the ocean in Santa Monica. When law enforcement searched his apartment, they knew for sure that they had finally caught Bulger. Inside, they found 30 guns, more than $822,000 in cash, ammunition, knives, and other incriminating evidence.

His girlfriend Catherin Greig was also captured and plead guilty to conspiracy to harbor a fugitive, conspiracy to commit identity fraud and identity fraud. She was sentenced to eight years in prison.

There’s a reason he was able to evade the police for so long.

His Acts Of Violence Were Obscene

Whitey Bulger was known to be so violent and ruthless that people wanted to stay as far away from him as possible. On one occasion, he lured in a girl into her own mother’s apartment and strangled her to death just because she wanted to break up with one of his associates.

He was also no stranger to torture, subjecting his victims to extended periods of torture before executing them. He would then bury them in one of the many shallow graves he had established throughout the city or throw them in the river.

He Was A Master Of Disguise

Considering how many years he successfully evaded the police, it’s safe to say that Bulger was very skillful in covering his tracks and fooling people with fake identities. After fleeing from Boston in 1995, he was even stopped by a police officer in Wyoming who believed his identification card and allowed him to continue on.

For the 16 years that he was on the run, he was spotted all over the world. He was even spotted in California seeing the film The Departed, a film based loosely on his own crimes.

Believe it or not, the community of South Boston didn’t despise him. Keep going to see why!

He Wasn’t The Only Famous Person In His Family

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While Bulger may have been the most notorious of his family members, he wasn’t the only one to gain state-wide prominence. Coming from a family with five other siblings, his younger brother William Bulger chose to live his life in the opposite direction of crime.

Instead, he went into politics and served as the president of the Massachusetts State Senate for an entire 18 years. After his time with the Senate was done, he went on to lead the University of Massachusetts,

He Had A Deep Sense Of Community In South Boston

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While his crimes and acts of violence are utterly contemptible, strangely enough, Bulger was known for his dedication to his community and fellow citizens in South Boston. According to local media reports, he was celebrated by many for keeping drug dealers out of the community.

He was also known to help people with their groceries, walk the elderly across the street, along with numerous other small acts of selflessness to help the innocent citizens of the community.

Even when Bulger didn’t need any more money, the unthinkable happened.

He Was A Meticulous Planner

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When you’re as well-known as Bulger, and not in a good way, it helps to be as organized and careful as possible when it comes to planning. This was something that Bulger made had mastered over the course of his career.

He knew where he stashed all of his bodies, was sure to remove their teeth, and once even helped dig up the remains of three bodies buried in a private home before the house was sold. He also stashed cash all over the United States in preparation for the possibility of a necessary escape.

He Ran Away And Joined The Circus

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When he was just 10 years old, Bulger was already demonstrating his “do what I want” attitude when he ran away and briefly joined the Barnum & Bailey Circus. Barnum and Bailey, now known as the Ringling Bros. was an American travelling circus that was the self-proclaimed Best Show On Earth, running from 1871 to 2017.

You can imagine if Bulger had stayed behind with the clowns and acrobats, he may have ended up leading a semi-normal life as a carny.

He “Won” The Lottery

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At a certain point, there wasn’t much that Bulger wasn’t capable of doing to make things go his way. In 1991, a man named Michael Linskey bought a winning Massachusetts lottery ticket for $14 million from a liquor store that Bulger owned. Of course, Bulger wasn’t just going to let a winning ticket walk out of his own doors without payment.

So, he “convinced” Linskey to say that he and Bulger had bought the ticket together. Saying no to Bulger wasn’t a very smart move, so the winnings were split up between Linskey, Bulger, and other associates.

You won’t believe the FBI record that he broke!

He Had A Soft Spot For Animals

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For a man that was either a part of or personally killed dozens of people, it’s a bit surprising to learn that Bulger actually had a soft spot for animals. For most killers like Bulger, there really ins’t a difference, but for him there was.

While on the run in Grand Isle, Louisiana, Bulger reportedly wept after a puppy was shit as a mercy kill that had been badly injured. He showed his soft side again while in the Cajun Bahamas fishing and threw back every fish he thought was too small to be killed. Who would have thought?

He’s Been Portrayed Numerous Times In Movies

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With a life story like Bulger’s, it would be strange if Hollywood hadn’t sunk their claws into it yet. But of course, they have, and more than once! His career as the head of the Irish mob in Boston and role as an FBI informant were the inspiration behind Jack Nicholson’s character Frank Costello in Martin Scorcese’s 2006 film The Departed.

Then, in 2015, Johnny Depp did a frightening portrayal of him in the biographical crime drama Black Mass, a film that really brought Bulger’s story to the public’s attention.

He Broke An FBI Record

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While during his 16 year period on the run, Bulger managed to become the second most-wanted man on the FBI’s Ten Most Wanted Fugitive list, only behind Osama bin Laden. As if that wasn’t impressive enough, in 2008, the FBI doubled the reward for his capture, raising the bounty to $2 million.

At the time, this was the record amount offered for a bounty in the United States. Even though he was still no longer the crime boss he once was, he was still clearly giving the FBI an incredibly hard time.