organized crime 9 Utterly Bizarre Facts About Famous Gangsters

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Gangsters: you love to hate 'em (or love to love 'em) in the movies. Wiseguys and crime lords living on the fringes of society are a staple of American cinema, and let’s face it - who doesn’t love a good gangster movie. But the real people who inspired our favorite movies were even stranger than fiction. From a Prohibition king’s troubling childhood jealousies to the founder of modern Las Vegas’s poor attempts at hair-related voodoo, these men proved throughout history that the best story to tell is always the true one. Here's a list of weird stories about your favorite famous gangsters. 

Charlie Luciano Got An STD On Purpose To Dodge The Draft


Charlie Luciano Got An STD On ... is listed (or ranked) 1 on the list 9 Utterly Bizarre Facts About Famous Gangsters
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Charlie “Lucky” Luciano was one of the kings of organized crime, and remained so even after his arrest, trial, and eventual deportation. Various biographers have struggled to sum up his life, and in doing so numerous colorful stories of varying levels of truth have cropped up about the man. The story about how he dodged the draft in World War I is perhaps the most bizarre:

At nineteen, Luciano was petrified that his finances would be lost should he be shipped overseas. In an attempt to dodge the draft, his friends advised him that a hearty case of syphilis should do the trick and allow him to to stay at home. At first Luciano strongly resisted the idea, telling his friends in no uncertain terms what they could do to themselves; eventually, he was convinced and his young friend Ben Siegel pointed him in the direction of a prostitute who gave him the clap. (Other sources say it was chlamydia or gonorrhea.)

And so Luciano avoided the war, though at a painful cost.


Bugsy Siegel is listed (or ranked) 2 on the list 9 Utterly Bizarre Facts About Famous Gangsters
Photo: New York Police Department

Benjamin “Bugsy” Siegel was one larger-than-life gangster, and is perhaps the second most well-known figure in 20th-century organized crime. The guy who created the idea of Las Vegas as we know it, Siegel’s exploits up until his violent demise in 1947 were the stuff of a gangster on the silver screen. As with Luciano, many biographers have tried to capture his story, and various accounts of the man have cropped up over the years. One anecdote from the pulpy biography We Only Kill Each Other stands out as a particular weird story:

Siegel was obsessed with his looks, and as a result worried when his hairline began to thin. Reportedly, he once cut off a lock of another man’s hair, went home, and burned the hair in some sort of attempt to use magic to get his own hair to thicken. It, of course, did not work. Siegel’s hair continued to thin as the other man’s stayed thick.

This particular story has never cropped up in any of the film or television shows that feature Siegel as a character, most likely because it’s almost too bizarre for even a man who was as showy as Vegas itself.

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John Dillinger is listed (or ranked) 3 on the list 9 Utterly Bizarre Facts About Famous Gangsters
Photo: Freebase/Public domain

The weirdest legend about the life of John Dillinger has already been put onscreen in nearly every biopic centered on the famous bank robber. While being held in prison, Dillinger managed to escape custody, passing armed guards to easily escape with the help of his own weapon: a block of wood carved to look like a gun. (Other sources say it was made out of a potato.)

It’s almost too good to be true - after all, how did so many people manage to be fooled by what was essentially a theatrical prop? Still, Dillinger was able to escape federal custody somehow, and if there’s an alternate explanation, most real crime gurus don’t want to hear it. Dillinger’s mad escape is better than fiction and has secured itself a place in American folklore. 

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Al Capone Accidentally Shot Himself In The Groin


Al Capone Accidentally Shot Hi... is listed (or ranked) 4 on the list 9 Utterly Bizarre Facts About Famous Gangsters
Photo: Miami Police Department

By and large, Capone is considered a historical badass. However, there was at least one time when that badass rep backfired. According to contemporary news reports. Capone was getting out of a car when the gun he always carried on him discharged and he shot himself in the groin. (Apparently, that wasn't the only time he shot accidentally shot himself, either - his caddy says Capone also shot himself with a gun stored in his golf bag.)

Of course mistakes happen to everyone. Who hasn’t tripped over their own feet or embarrassed themselves? Still, when you’re one of history’s most famous gangsters, shooting yourself in the groin proves you’re still human. 


Arnold Rothstein is listed (or ranked) 5 on the list 9 Utterly Bizarre Facts About Famous Gangsters
Photo: via Wikipedia

Savvy TV viewers might already be fairly knowledgeable about Arnold Rothstein courtesy of Michael Stuhlbarg’s work on Boardwalk Empire, but for those of you who are new to the mobster game, Rothstein is considered to be the father of organized crime as we know it. Known as the Big Brain, Rothstein is perhaps most infamous for fixing the 1919 World Series. Most notably, he was also a king of Prohibition and was behind a great deal of New York’s bootlegging empire in the Roaring Twenties. 

But interestingly enough, Rothstein himself was a teetotaler, refraining from ever drinking alcohol. Instead, his drink of choice was milk. He drank a huge quantity of milk. He also frequently suffered from stomach trouble, leading biographers to wonder if perhaps the man was lactose intolerant. It’s strange to think that a man famous for planting the seeds of organized crime in the country was such a stickler for propriety, yet Rothstein always was above the law in terms of imbibing. 

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Arnold Rothstein Tried To Kill His Brother When He Was Only Three Years Old


Arnold Rothstein Tried To Kill... is listed (or ranked) 6 on the list 9 Utterly Bizarre Facts About Famous Gangsters
Photo: via YouTube

Rothstein’s childhood contains an even stranger anecdote. The future crime lord suffered from extreme jealousy as a child, believing that everyone loved his brother more than him. When his mother took his siblings out of the city to visit relatives, Rothstein’s father found him sobbing in a closet that everyone loved his brother and no one loved him.

It was also reported in the biography Rothstein that his childhood jealousy nearly bubbled over into violence. Rothstein’s father apparently once also found Rothstein hovering over his brother’s bed with a knife, with full intention to do harm to his brother. While nothing happened, it’s enough to send a chill up the spine imagining a young Rothstein on a mission to do away with a perceived threat. Though not famous for being a violent man, this surely was a sign of notoriety in Rothstein’s future.


Mickey Cohen is listed (or ranked) 7 on the list 9 Utterly Bizarre Facts About Famous Gangsters
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Mickey Cohen was Los Angeles’s pint-sized Capone. He took over Los Angeles’s crime scene following the death of Cohen’s mentor, Bugsy Siegel. Cohen hopped in and out of jail, returning to his home city following each release to continue his crime spree. While lesser-known than some of his contemporaries, he was just as vicious as they were, ruling the LA scene with an iron fist.

He was also a devoted father to his dog, Toughie. The dog was perhaps even more beloved than Cohen’s wife. Cohen was so devoted to his pup that he even built a miniature version of his own bed for the dog to sleep on. The dog proved to be as hardy as his owner - when a bomb took out part of Cohen’s house, Toughie was unharmed, as were Cohen and his wife. 

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Al Capone is listed (or ranked) 8 on the list 9 Utterly Bizarre Facts About Famous Gangsters
Photo: Freebase/Public domain

Al Capone: the name itself is synonymous with organized crime. The most famous figure in America’s history of organized crime, Capone cut a bloody swath through Chicago up until his trial in 1931 for tax fraud (interestingly enough, Capone was never convicted of murder). Capone’s likeness has been captured in books, film, and television, with the frightening mantle of “Scarface” thrown around due to three scars on his face from a bar fight he had with an insulted woman's brother.

However, Capone never liked the name Scarface. In fact, most of his friends called him “Snorky." Now, Snorky was slang for a well-dressed gentleman, so it's not a bad name, but set next to Capone’s violence and cruelty, it seems like an odd choice of nickname, and one that also hasn’t graduated yet to Capone’s silver screen presence. Maybe the next biopic will name-drop his nickname of choice.

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