Meet The Real Life Gangster Behind Johnny Depp's Latest Film

To be fair, James “Whitey” Bulger sounds like a total f*cking lunatic.
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Matt Allen
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To be fair, James “Whitey” Bulger sounds like a total f*cking lunatic.
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Johnny Depp has done it again, this time using his unique acting talents to bring to life the notorious gangster James “Whitey” Bulger. The film Black Mass is already being heralded as a cinematic triumph and Depp’s portrayal is touted as being the key reason for this anticipated success.

The lead role required someone who could get across a character who is evil, twisted, cruel and capable of extreme violence; stopping at nothing to become the number one crime boss of Boston. So who is James “Whitey” Bulger and why is his story worthy of the silver screen treatment?

By the age of just fourteen, Bulger had joined a well-known South Boston gang known as the "Shamrocks" and was quickly making a name for himself. Even at this young age, he was arrested and charged with assault, forgery and armed robbery and was eventually sentenced to a juvenile prison.

Upon being released in 1948, he joined the military, however not even the hard discipline here could straighten him out and after involvement in several assaults and going absent without leave, he was unsurprisingly discharged.

With nothing left to support him, Whitey again turned to crime. Lengthy prison time followed after being sentenced again for armed robbery and truck hijacking. Nine years were served behind bars before his eventual release. It was straight out of prison and straight back into a life of crime for Bulger. He found work as a bookmaker and loan shark, dealing with a man called Donald Killeen. Killeen was the boss of a feared Irish mob gang and in 1971, his younger brother bit off the nose of Michael Dwyer, a member of the rival mob. A war broke out as a result which led to numerous killings throughout the Boston area. It was during this war that Bulger took his first life.

The gang war ended and as a result of the truce Whitey had worked his way into the position of being able to control the entire South Boston criminal underworld. Over the years that followed, Bulger began to tighten his grip on the city by sanctioning the killings of anyone who he deemed to have stepped out of line. He was not afraid to get his hands dirty and his own personal murder haul was nearing double figures.

By this point, everyone knew where they stood with Bulger. You either conducted business with him his way or he wouldn't hesitate to use violence. His belief was that if someone deserved a beating then they may as well be dead. He was now very well known to the FBI. Rather than look to arrest Bulger, they instead made him an informant and his intelligence was pivotal in bringing down the Italian Mafia Patriarca crime family. Informing on a rival family played straight into Bulgers hands. He had eliminated the opposition and gained protection from the authorities. A stroke of genius that had other criminals saying that Whitey could even teach the Devil a trick or two.

During the 1980s, Bulger began to realise that bookmakers and loan sharking was all well and good but if he wanted to make real money then that lay in the business of drug trafficking. He summoned drug dealers from in and around Boston to his headquarters and would inform each dealer that he had been offered a substantial sum in return for that dealer's assassination. He would then demand a large cash payment not to do so. With his foot in the door of this new enterprise, Whitey enforced strict rules over the dealers who were paying him protection and he set about putting all heroin dealers out of business. He wanted to clean Boston of that drug. Do not be fooled as this wasn’t a noble quest. He realised that those on cocaine and other drugs were still able to socialise and put money into his other business; heroin however had the opposite effect. He saw these people as a waste of time with nothing to profit from.

There was to be no selling of drugs to children and those dealers who refused to play by his rules were violently removed from the neighborhood. It was in the 1990’s that his empire had taken off and it was believed that his drug racketeering alone had made him over thirty million dollars. With his financial peak also came several FBI investigations. No longer an informant and the head of all criminal activity in the region, Bulger had no choice but to go on the run.

After sixteen years at large and twelve years on the Worlds Most Wanted Fugitives list, Bulger was arrested in California in 2011. The jury convicted him of 31 out of 32 counts of racketeering charges as well as the jury convicting him of the murders of 11 victims, although his actual toll is believed to be so much higher. He was sentenced to two terms of life imprisonment plus five years and so came to an end one of the most infamous names in gangland history.

James “Whitey” Bulger is now 86 years old and refused to meet or have anything to do with Depp throughout the process of the making of the film. Depp has said that he did reach out to Whitey but that “knowing he wasn’t the most ardent fan of the book Black Mass, I always knew that it was unlikely to pan out.” It is no surprise that, now that the film has been released, Bulger’s anger has only grown.

Johnny Depp referred to Whitey Bulger as having a kind heart, this has caused a lot of controversy as you can imagine. He later explained that he was only trying to see the mobster as “a human being and not only as a man in that business” but families of Bulger’s victims were offended and are still outraged with the films release.

Bulgers name is now back in the papers. Even serving two life sentences and knowing that he will never be a free man again, Whitey continues to show signs of the young man who made criminal history with his notorious, violent and often cruel antics.

@Mr_Mallen