Organized Crime
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9 Utterly Bizarre Facts About Famous Gangsters

Updated July 23, 2021 397.5k views9 items
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Gangsters: You love to hate 'em (or love to love 'em) in the movies. Wiseguys and mob bosses living on the fringes of society are a staple of American cinema, and let’s face it - who doesn’t love a good mafia 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. 

  • Charlie Luciano Got An STD On Purpose To Dodge The Draft

    Photo: Remo Nassi / Wikimedia Commons / Public domain

    Charlie “Lucky” Luciano was one of the lawless kings of his time and remained so even after his 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. One story about how he dodged the draft in World War I is perhaps the most bizarre.

    At 19, 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 the clap should do the trick and allow him 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, his young friend Bugsy Siegel convinced him and pointed him in the direction of a lady of the evening.

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

  • Photo: New York Police Department / Wikimedia Commons / Public domain

    Benjamin “Bugsy” Siegel was larger-than-life and is perhaps the second most well-known figure in the 20th-century American underworld. As the guy who created the idea of Las Vegas as we know it, Siegel’s exploits up until his demise in 1947 were the stuff of movies. 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 particularly 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. This, 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 - even for a man who was as showy as Vegas itself.

  • John Dillinger Once Escaped Prison Using A Block Of Wood

    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 incarcerated, Dillinger managed to escape custody, passing armed guards with the help of his own weapon: a block of wood carved to look like a gun

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


    #7 of 10 How 10 Notorious Criminals From History Actually Got Caught#5 of 13 Things We Just Learned About Historic Prison Escapes#7 of 12 12 Historical Figures You Didn't Know Had STDs

  • Al Capone Accidentally Shot Himself In The Groin

    Photo: Miami Police Department / Wikimedia Commons / Public domain

    By and large, Capone is considered a historical tough guy. However, there was at least one time when that rep backfired. According to contemporary news reports. Capone was getting out of a car when the gun he always carried on his person discharged and he shot himself in the groin. (Apparently, that wasn't the only time he accidentally shot himself, either - his caddy says Capone had another accident with a piece 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 outlaws, shooting yourself in the groin proves you’re still human.