Insane True Stories of High-Risk Gamblers

When it comes to high-risk gamblers, there are probably as many names and insane stories as there are for those that lost it big. After all, gambling is an incredibly old past-time and it’s hard to separate the fact from the legends that surround these famous personas. Still, we’ve decided to go ahead and compile a list of some our favorite gambling stories and hope that they’ll serve as inspiration for any aspiring high-risk gamblers out there.

#3 Charles Wells

Charles Deville Wells was a gambler during a simpler time, specifically in the late nineteenth and early twentieth century. That’s right: He made his fortune back when people were still shocked about this whole telephone malarkey.

Roulette was his game of choice, which, for those that have read our guide to high-risk betting, will recognize as the game that comes most highly recommended. Using the martingale system, which calls for doubling up to make up for losses, Charles Wells was able to win and win and win and win. After one of the luckiest streaks the Monte Carlo Casino had ever seen, Wells walked away with more than a million francs to his name. While everyone that witnessed his miraculous win was sure that he had rigged the game somehow, private detectives were unable to discover his method. Ultimately, he begrudgingly admitted his secret: he was just really, really lucky.

#2 Johnny Chan

Known as “The Great Wall of China,” Johnny Chan was a big name particularly in the late eighties, although he is still widely recognized and continues to play in poker tournaments to this day. While the World Series of Poker has soared in popularity and inspired many people to try their hand at poker, Johnny Chan was one of the few that not only won the championship, but won it two times in a row. That’s taking high-risk gambling to a whole other level.

#1 Kerry Packer

Kerry Packer had made a name for himself in Australia thanks to the strength of his family’s vast fortune in magazines. As is common for those that earn more money than they need to survive, Packer took up a hobby. In this case, that hobby was gambling. While his life as a billionaire has never come into jeopardy, he has made a name for himself as a man that is more than willing to put up large swaths of dough to try and seal a win. Sometimes this works, like when he walked away with almost thirty million dollars from a blackjack table. Other times, not so much, like when he lost almost twenty million dollars in one stay at the Crockfords best casino match bonuses in London. Truly, if there was ever a man that understood the life of a high-risk gambler, it would be Kerry Packer.