On this episode of the Sofa King Podcast, we do some mobster-style true crime and talk about the kingpin of Boston, Whitey Bulger. In the 1970s and 80s, Bulger ran the Winter Hill Gang and was the head of the Irish Mob in the Boston area. This was a title he earned through several wars with the Irish, a deal with the Italians, and a whole lotta bodies. His story was so wild that Martin Scorsese based Jack Nicholson’s character from The Departed on him. Johnny Depp also played him in Black Mass. Whitey was part of MKUltra, supported the Irish Republican Army, and turned his job as an FBI informant on its ear, corrupting the local feds. He managed to escape capture by globe-trotting with his girlfriend for 16 years.

Born to two immigrants from Canada, James “Whitey” Bulger was a typical Southie kid from Boston. His father was a longshoreman who lost his arm in an accident and could no longer work. While Whitey’s siblings all did well in school and walked the straight and narrow, he turned to the streets. He was in a gang called the Shamrocks by the age of 14, and in his time with them he was arrested for assault, forgery and armed robbery. Once out of jail, he spent some time in the military but spent as much time in the brig as he did serving his country.

At 26 years old, he got arrested for armed robbery while jacking a truck. In prison, he volunteered for the MKUltra project once he found out he’d get paid to take drugs. It didn’t go so well as the LSD took its toll, but eventually he got out. Once free, he found himself in the middle of a war between Irish gangs. He killed the wrong guy, like you do, and escalated things until the Italian mob got involved and settled a peace.

This was the birth of the Winter Hill Gang. From there, he raised in the ranks. He did it all. Extortion, theft, armed robbery, murder, anything you can think of that a mafia does, you can bet Whitey did it. Some say his mob was even responsible for the Gardner Museum Heist. Eventually, he became an FBI informant, though he prided himself on serving them weak information in return for favors. In time, he had his two FBI handlers accepting bribes and giving him tips and covering from every crime he committed. In fact, when the entire leadership of the Winter Hill Gang was arrested, Whitey was spared by the FBI and took control of the gang.

He ran Boston with a strange code that he had, and he was racist, using terrorist tactics to try and stop desegregation of schools in the 1960s. Eventually, the DEA and local police figured out that the FBI was covering for him, so they build their own case. Whitey’s FBI guys tipped him off, however, and he went on the run for a whopping 16 years. At one point, he even beat Osama Bin Laden on the top 10 most wanted list. So, how did his girlfriend’s boob job help get them caught? Where were they living? How many murders did he get sentenced for? What brutal end did he face at the hands of other mobsters while an old man in jail? How did his own plans to die on the lamb lead to an abandoned mine shaft in Arizona? Listen, laugh, learn.

 

 

Visit Our Sources:

https://en.wikipedia.org/wiki/Whitey_Bulger

https://www.youtube.com/watch?v=_9j5I6h8Q-0

https://www.nytimes.com/2018/10/30/obituaries/whitey-bulger-dead.html

https://archive.nytimes.com/www.nytimes.com/interactive/us/bulger-timeline.html

https://themobmuseum.org/notable_names/whitey-bulger/

https://www.cnn.com/2018/10/31/us/james-whitey-bulger/index.html

https://www.nbcnews.com/news/us-news/whitey-bulger-juror-regrets-conviction-after-receiving-dozens-letters-crime-n1137871