9 Utterly Bizarre Facts About Famous Gangsters

Kate Gardner
Updated July 23, 2021 428.4K views 9 items

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

    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.

  • Bugsy Siegel May Have Tried To Fix His Hairline Using Magic
    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.

  • Al Capone Accidentally Shot Himself In The Groin

    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. 

  • Prohibition Kingpin Arnold Rothstein Never Drank Alcohol
    Photo: Chicago Daily News archives/Staff Photographer / Wikimedia Commons / Public domain

    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 the father of the mob 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. 

  • At Only Three Years Old, Arnold Rothstein Tried To Off His Brother

    Rothstein’s childhood contains an even stranger anecdote. He 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 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. 

  • Mickey Cohen Was A Devoted Dog Dad
    Photo: United States Department of Justice / Wikimedia Commons / Public domain

    Mickey Cohen was Los Angeles’s pint-sized Capone. He took over Los Angeles’s scene following the demise of his mentor, Bugsy Siegel. Cohen hopped in and out of jail, returning to his home city following each release to continue his unlawful activities. 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. 

  • Al Capone's Friends Called Him Snorky
    Photo: Chicago Bureau (Federal Bureau of Investigation) - Wide World Photos / Wikimedia Commons / Public domain

    One of the most notorious figures in American history, Al Capone cut a swath through Chicago up until his trial in 1931 for tax fraud (interestingly enough, Capone was never convicted of murder). Capone’s story 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 nickname 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 considering Capone’s cruelty, it seems like an odd choice - and one that also hasn’t graduated to Capone’s silver screen presence. Maybe the next biopic will name-drop his nickname of choice.

  • Meyer Lansky Inspired A Member Of The Wu-Tang Clan
    Photo: Al Ravenna, World Telegram staff photographer / Wikimedia Commons / No known copyright restrictions

    Meyer Lansky, another one of Siegel’s and Luciano’s cronies, managed to avoid the fates of his counterparts. He was never jailed, despite the US government chasing him, and managed to live until he was 80 years old. Unlike Luciano and Siegel, he tended to avoid showboating and celebrity. It’s most likely why he was able to live to such a ripe old age. However, he did receive one odd tribute.

    One rapper affiliated with the group Wu-Tang Clan goes by the stage name Myalansky in honor of the man. It’s hard to say whether Lansky would’ve liked having a member of the Wu-Tang Clan named after him, but it’s a surprising tribute to one of the underworld's quietest members.