Known for its glitz and glam, gambling has always attracted larger-than-life personalities – people who simply thrive on risk, strategy and the tantalising promise of fame and fortune. Throughout history, high rollers have captivated our imaginations with their sheer audacity, skill and sometimes even their luck.
But who are they?
Stick with us while we delve into the stories of some of the most famous gamblers in history, showcasing their incredible feats and the legacies they’ve left behind.
The Maverick of the Poker World: Doyle “Texas Dolly” Brunson
Doyle Brunson, otherwise known as “Texas Dolly”, is a towering figure in the world of professional poker. Born in Texas in 1933, Brunson’s early dreams of becoming a professional basketball player were dashed when he experienced a devastating career-ending injury. He ended up turning to poker and he was an absolute natural.
Brunson’s achievements in the world of poker are unparalleled. He has won ten World Series of Poker (WSOP) bracelets, including back-to-back Main Event titles in 1976 and 1977. His book, “Super/System”, published in 1979, completely revolutionised the way poker is played and studied, providing deep insights into the game’s strategy.
Amassing millions in tournament earnings during his career, Brunson was known for his fearless style of playing as well as his uncanny ability to read his opponents. Even later in life, in his 80s, Brunson has remained a formidable presence at the poker table, inspiring generations of players with his skill and tenacity.
The Notorious “King of the Gamblers”: Nick “The Greek” Dandolos
Nick Dandolos, otherwise known as Nick “The Greek” in the gambling world, is a legendary figure in the world of gambling. Born in Greece in 1883, as his nickname suggests, Dandolos moved to the United States in his twenties, and it wasn’t long before he made a name for himself as a high-stakes gambler. His gambling exploits spanned many different games, including baccarat, poker and craps.
Most people will know Dandolos for his marathon poker match against Johny Moss in 1949. Organised by Benny Binion, a successful casino owner at the time, the match lasted an incredible five months with Dandolos and Moss playing continuously.
The standoff ended with Dandolos reportedly losing millions. He departed from the engagement by famously remarking, “Mr. Moss, I have to let you go”, an acknowledgment of Moss’s superior skill and play.
Despite his losses, Dandolos’s charisma and larger-than-life personality made him a beloved figure in gambling circles. Today, he’s remembered not only for his exceptional skill in the world of gambling, but also for his generosity, as he often donated his winnings to charity.
The Ultimate Blackjack Risk Taker: Don Johnson
After his incredible winning streak in 2010-2011, Don Johnson’s name became synonymous with blackjack. As a seasoned gambler and professional bettor, he took on three Atlantic City casinos and ended up walking away with more than $15 million in winnings.
Johnson certainly wasn’t merely lucky. He used his immense knowledge of blackjack and negotiated with casinos to achieve favourable rules, including things like rebates on losses and higher betting limits. Johnson was able to turn the odds in his favour by exploiting these advantages and employing a disciplined betting strategy.
His victories against the casinos led to major changes in blackjack rules in an attempt to prevent similar exploits. Indeed, Johnson’s story highlights the importance of skill, strategy and negotiating in the world of gambling.
Bold in Baccarat: Phil Ivey
Phil Ivey is frequently regarded as one of the greatest poker players of all time, but his gambling prowess extends far beyond poker. In 2012, Ivey made headlines with his extraordinary winnings earned at baccarat, a game he had rarely played at high stakes in the past.
Along with a partner, Ivey won about $20 million from just two casinos in London and Atlantic City by using a technique called edge sorting. This technique involved identifying subtle defects in the cards in order to gain an advantage. Ivey always maintained that his tactics were legitimate, the casinos disagreed and refused to pay his winnings which led to lengthy legal battles.
Despite the controversy, Ivey’s success in the unlikely game of baccarat showcases his keen observational skills and strategic thinking. His story highlights the fine line between strategy and so-called cheating in the gambling world.
The Card Counting Wizard: Edward Thorp
Although he’s not quite a traditional high roller, so to speak, Thorp’s contributions to the world of gambling are nothing short of monumental. As a mathematics professor, Thorp is best known for his pioneering work in card counting, a strategy that revolutionised blackjack.
In the early ‘60s, Thorp developed a card-counting system that allowed players to gain a statistical advantage over the house. His groundbreaking book, “Beat the Dealer”, published in 1962, provided an in-depth explanation of his method, and it quickly became a best-seller.
Thorp is an icon in the gambling industry, because not only was he wildly successful, but he also dramatically influenced the industry as a whole. His work led to significant changes in blackjack rules and increased scrutiny of card counters. Indeed, his story highlights the power of mathematical strategy in gambling and its potential to outwit even the most sophisticated casinos in the world.
A Daring Casino Owner: Kerry Packer
Last but not least, Kerry Packer is known as not only one of the wealthiest men in the world, but also an incredibly audacious gambler. An Australian media mogul, Packer was known for high-stakes bets and big personality. Indeed, his exploits are the stuff of legends.
His favourite games were blackjack and baccarat, and you can play these at sites like Bella Vegas casino, too. Packer was notorious for wagering millions of dollars in single sessions and in one famous incident occurred in Las Vegas he reportedly won $20 million in just one night, prompting the casino to permanently close his account.
Packer was also known for his generosity. He’d often tip casino staff and fellow gamblers large sums of money.
Packer’s gambling style was characterised by a combination of his generous spirit and bold risk-taking, making him a revered figure in gambling circles all over the world and through time.
