Organized Crime 9 Utterly Bizarre Facts About Famous Gangsters  

Kate Gardner
334.1k views 9 items

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
Photo: via Wikimedia

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: Metaweb (FB)/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.