The Kings of Gambling: History’s Most Successful High Rollers

Gambling has existed, in one form or another, since time immemorial. When we make such a sweeping statement, it is no empty claim: archaeological evidence suggests that even the earliest caveman indulged, with the first dice-like objects, made from bones, dating back 40,000 years.

Gambling paraphernalia has turned up in the ruins of Pompeii too, as noted on the website – some of it loaded for cheating, providing a fascinating and all-too-human glimpse into this lost civilization. Even in mythology, the ancient world and its outcomes turned on gaming, with Zeus, Hades, and Poseidon splitting the universe according to a simple yet eternal mechanism: the throw of a dice, as explains.     

Yet, some of history’s gamblers have done better than others. In this article, we take a look at the most successful high rollers of all time.

Phil Ivey

Today, gambling is more accessible than it has ever been before, thanks to the advent of online play and the many bonuses that are out there, both of which have helped to bring prices down. Indeed, the latter has proven so popular among this new wave of players that there are now entire sites dedicated to sharing the best offers and promotions currently active, such as

However, even the most brilliant aspiring poker player is unlikely to match the successes of Phil Ivey, who has been crowned champion of the World Series an incredible 10 times. Widely (and validly) considered to be the best player in the world, the 43-year-old California native has too many tournament wins to even begin to list them here.    

Yet, it’s not only poker where Ivey reigns supreme – in 2012, he also won $11 million during a baccarat game in London. Today, this most successful of gamblers has an estimated net worth of over $100 million.

Billy Walters

Despite coming from the humblest of beginnings, Billy Walters is sports betting royalty. Widely considered to be the most successful sports bettor of all time, he has claimed wins at all of the most popular Las Vegas casinos.  

Walters’ winning streak has endured for over 30 years now, which means his successes cannot be explained away as simple luck. So how did the orphaned child from Kentucky develop such an incredible skill set? He’s never yet let on, and is famed for keeping his cards close to his chest.  

Like Ivey, Walters is reputed to be worth over $100 million as a result of his many victories.

Don Johnson

Don Johnson is a businessman through and through, whether it comes to cutting a real-estate deal or negotiating terms with Atlantic City casinos. It’s this latter skill set that allowed him to win over $15 million playing blackjack – without any card counting necessary.   

Between 2011 and 2012, Johnson made a run against the three Atlantic City casinos, insisting on blackjack rules that gave the house only a small edge (roughly 0.26 percent). He also managed to arrange a loss rebate deal, which limited how much he might lose.

That being said, his safeguarding actions were entirely unnecessary, and he walked away with record wins, and a record sum to boot.

Would you ever consider trying to replicate these successes for yourself, or are you someone who prefers to play it safe?  

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