The saying, “it takes all sorts,” is especially true when it comes to gambling. Casinos attract all types, from the more glamorous patrons like millionaires, politicians and celebrities to a less savory crowd of criminals and cheats. Of course the high profile exploits of some gambling criminals turned them into celebrities too. In this article, we’ll highlight some of the most famous (and infamous) gambling criminals to ever step foot in a casino or card room.
Best known as a bank and train robber, this famed historical outlaw was also an avid gambler. A fan of both faro and poker, James played in both saloons and on boats and more than once was rumored to stop in mid-chase to play a game. To this day, an aggressive player prone to bluffs (aka a thief) is still commonly referred to as a “Jesse James.” A non-suited 4 and 5 in the hole is also frequently called a Jesse James because he was assassinated with a Colt .45.
A bookie, a businessman, a gangster and a gambler, millionaire Arnold Rothstein was at the heart of the 1919 “Black Sox” World Series scandal. He personally arranged for the White Sox to throw the game, since he had already bet against them. Rothstein is unique in this crowd because for the entirety of his life he was an East Coast man. He still managed to get himself into gambling trouble without ever setting foot in one of Las Vegas’ crime-run casinos. Rothstein met his end after he lost $320k in a three-day poker tournament in 1928. He refused to pay the debt, claiming the game was fixed, and later paid a much larger debt when the game’s winner put a hit out on him.
We’ll keep Siegel’s bio short and sweet, since most Las Vegas fans are already familiar with this gambling icon. This gambling mobster transformed Las Vegas when he helmed the construction and opening of the Flamingo, then the largest and most glamorous casino in Sin City. But Perhaps Bugsy’s biggest gamble was ever coming to Las Vegas at all; he lost big when he was assassinated in 1947. Rumor has it that his ghost still haunts the halls of the modern Flamingo.
Regarded by some as one of the “good guys” in the Wild West, Holliday nevertheless killed several men and accumulated a long list of criminal charges in his relatively short life. Originally an educated dentist, Holliday eventually dropped his respectable career in favor of card sharking. Holliday’s equally notorious friend, Wyatt Earp, summed him up best when he said, “Doc was a dentist not a lawman or an assassin, whom necessity had made a gambler.”Frank Lawrence “Lefty” Rosenthal
Lefty Rosenthal is one of Las Vegas’ most modern gambling criminals. In his Vegas heyday, Rosenthal secretly controlled much of the Strip, overseeing operations at the Stardust, Fremont (of Fremont Street fame), Hacienda and Marina casinos. Whispers of Rosenthal’s mafia ties were abundant, though he was never successfully charged. One of Rosenthal’s many enemies attempted to kill him in a car explosion in 1982, but Rosenthal left the city alive—albeit unwillingly—when he was Black Booked in 1988. Rumor has it that a disguised Rosenthal snuck back into Vegas several times before his death in 2008.