5 Most Insane Bootleggers Of Prohibition


Credit: Douglas Miller/Getty Images

Happy Repeal Day! On December 5, 1933 at 5:32 EST, the state of Utah ratified the 21st Amendment, providing the three-fourths majority needed to officially end Prohibition in the United States. (Yes, you should thank Utah of all states whenever you enjoy a beer.)

Everyone knows that Prohibition was a horrible idea that unleashed lawlessness, political corruption and violence, creating some of the most notorious and violent criminals in American history. Here are just a few of the craziest bootleggers of the Prohibition era.

1. George Remus


Photo via PBS

A lawyer who broke the law and became known as “King of the Bootleggers,” Remus even served as the inspiration for F. Scott Fitzgerald’s character Jay Gatsby. By buying bonded whiskey used for medicinal purposes, and then hiring people to hijack it, Remus made $40 million in less than three years, nearly a billion in today’s currency.

He eventually went to jail for violating Prohibition. When he got out, he murdered his wife for starting a relationship with a government agent. Being a lawyer, he successfully defended himself by arguing temporary insanity, and then successfully argued that he shouldn’t be thrown in an insane asylum… by using the prosecution’s own case.

2. Charles Luciano


Photo via Biography

Charles “Lucky” Luciano is widely credited as the father of modern organized crime, splitting the New York mafia into five families. During Prohibition he teamed up with Arnold “The Brain” Rothstein and other characters from “Boardwalk Empire.” By 1925 he was making $4 million per year in profit, and he eventually became so powerful that the Office of Naval Intelligence commuted his prison sentence in exchange for Sicilian mafia contacts during World War II.

3. Al Capone

The original Scarface, Al Capone is probably the most notorious criminal of the Prohibition era. Most famously, he’s responsible for the St. Valentine’s Day Massacre, in which two of his henchmen impersonated police officers and murdered seven of his rivals. He probably would’ve gotten away with even more crimes, had it not been for those pesky tax evasion charges… and complications from syphilis.

4. Dean O’Banion


Photo via deanobanion.com

A New York-based Irish gangster, Dean O’Banion was crazy enough to steal from Charles Luciano and other more powerful mafia members. That didn’t work out so well for him: He got murdered at his flower shop after ignoring a “back off” from Al Capone about a powerful mafioso’s gambling debt.

5. William McCoy


Photo via Time

He spawned the term “the real McCoy,” because his liquor was never diluted. But since it was so high-quality, McCoy made enemies out of both the U.S. government and other bootleggers. Eventually the Coast Guard caught him on his boat, but only after a machine gun firefight. He was basically a modern-day pirate, rum and all.

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