In his 89 years of life, James “Whitey” Bulger mostly did whatever the hell he pleased—and usually got away with it. The notorious Boston gangster held his hometown in his clutches as the leader of the Winter Hill Gang. He was involved with everything from racketeering, extortion, murder, narcotics, and money laundering. He was eventually charged with the murder of 19 people (that we even know about) after being on the lamb for 16 years.
His story was told (not very well) in the Johnny Depp movie Black Mass (the book is much better!) The character of “Costello” in The Departed (played by Jack Nicholson) was inspired by the story of Whitey Bulger.
(Spoiler alert) He wound up killed by a younger version of himself on his first day at a prison in West Virginia. His whole life he railed against rats and snitches—but it turns out he was one of the biggest FBI informants in the 70s & 80s which shielded him from the law.
His legacy of mayhem and murder continues in the culture of Boston and the number of supposed “good guys” who were complicit in his crimes will blow your mind.
Trigger warnings: Murder, violence, sexual assault, and Margo’s frequent attempts at a Boston accent.
The main sources for this episode:
- Whitey Bulger Wikipedia
- NY Times
- The Mob Museum
- Boston Globe
- NBC News
- NBC News Boston
- Boston Magazine
- “Whitey: The United States of America v. James J. Bulger” directed by Joe Berlinger
- “The Irish Mob” (Amazon Prime)
- “Manhunt: Kill or Capture”
- Black Mass by Dick Lehr and Gerald O’Neill
- Black Mass (film) directed by Scott Cooper
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