The premise that the house invariably triumphs is widely accepted, and indeed, it usually does. Yet, every so often, a daring gambler possessing extraordinary skill, audacity, or wealth emerges, defying the odds and accruing immense fortunes in doing so. While casual betting is a pastime for many, there exists an exclusive cadre of individuals who have committed their lives to outwitting the system. As we delve further into their stories, we’ll explore how these remarkable people climbed to the pinnacle of the world’s most prosperous gamblers and the substantial winnings they have accumulated on their journey.
Kerry Packer
Kerry Packer, best known as Australia’s wealthiest man, made his fortune through his family’s business empire, but his high-stakes gambling is what he will forever be remembered for. Packer was famed for his daring bets, a bold blackjack strategy that often led to substantial losses.
His audacious approach to play saw him endure some notably bad runs in his gambling career. The most infamous of these was from September 1999 to July 2000, where he incurred losses of around $40 million at Crockford’s casino in London and the Bellagio in Las Vegas.
But Packer’s story wasn’t just about losses. He had his moments of victory too, the most memorable being in May 1995. In an astonishing display of blackjack strategy, he won $20 million in just 40 minutes, playing several rounds of blackjack simultaneously with each stake set at a whopping $250,000.
2. Tony Bloom
Tony Bloom, similar to many others who’ve accumulated wealth in the world of gambling, retains an air of mystery around him. He is known to have studied mathematics at The University of Manchester and ventured into poker initially as a mere hobby. This recreational activity has since brought him earnings close to $2.5 million and allowed him to participate in major tournaments like the World Poker Tour and Poker Million IX, where he finished as the runner-up. His nerveless style of play at the poker table earned him the nickname “The Lizard.” Despite his success in poker, it is not the main contributor to Bloom’s fortune. He has amassed millions through his own betting consultancy business, Starlizard. Several reports are indicating that Starlizard is among the top betting companies globally, wagering millions of dollars on soccer leagues worldwide.
3. Bill Benter
Bill Benter, a mathematical prodigy, has skillfully used his intellectual prowess to garner a fortune through gambling. His journey in the gambling world began with card counting in Las Vegas, like many other beginners. However, he later pivoted his attention to horse racing in Hong Kong. Alongside Alan Woods, another gambler, Benter developed an algorithm with an exceptional ability to predict a horse’s likelihood of winning. Although the initial years were tough and required some modifications, his model eventually started bringing in tens of millions of dollars on an annual basis. Benter’s most significant triumph was when his model precisely predicted the Triple Trio, a well-known bet in Hong Kong that involves correctly predicting the top three horses in three distinct races. Today, as a billionaire, Benter spends his time giving lectures at universities and donating to various charitable causes worldwide.
4. Edward Thorp
Edward Thorp, the man who served as an inspiration for Bill Benter to venture into gambling and the brains behind card counting, comes in a close second to Benter. Thorp utilized his mathematical expertise and technological savvy to devise a strategy that neutralized the house advantage in blackjack. His first weekend testing this technique yielded him $11,000, and its effectiveness prompted him to pen down a book detailing his methods. The 1962 publication, “Beat the Dealer,” was a smashing success, selling over a million copies. Not stopping there, Thorp went on to invent the first wearable computer – a tool that enhanced his chances of winning at roulette. His decision to channel his gambling skills into the stock market led to a massive surge in his wealth, establishing him as an incredibly wealthy individual ever since.
5. Alan Woods
Alan Woods, once an ally of Bill Benter, accrued his wealth in a manner akin to Benter. Their early ventures involved card counting, and they were even teammates at one juncture. However, their expulsion from the Las Vegas casinos led them to redirect their interest towards Hong Kong horse racing. A falling out between the two saw Woods creating his successful model, rivaling Benter’s. When law enforcement began investigating his betting syndicate, Woods found refuge in the Philippines. Unfazed by the setback, he continued his betting operations from his private property, amassing an astounding fortune of approximately half a billion dollars. Interestingly, he also established a strong partnership with Zeljko Ranogajec, a former adversary.
6. Zeljko Ranogajec
Zeljko Ranogajec, more commonly known as “The Joker,” is a prosperous individual who has built his fortune through advantage gambling. He started with a modest sum of a few hundred dollars, which he skillfully multiplied into millions at the blackjack table. Before forming his betting syndicate called the Bankroll, he partnered with Alan Woods. His syndicate primarily bets on horse racing and is reported to place wagers totaling over $3 billion each year. Even though not all these bets are won, Ranogajec continues to profit thanks to the considerable discounts and rebates he receives from bookmakers on his massive bets. Despite Ranogajec’s preference for a low-key lifestyle, his enormous wealth is less discreet. Among his assets is an apartment in One Hyde Park, known as the world’s most expensive residential building. Astoundingly, it’s reported that his syndicate’s bets make up a third of Betfair Australia’s total operations.
7. Billy Walters
Billy Walters, often hailed as one of the most successful sports gamblers in history, has openly shared that he only had a single losing season throughout his 39-year career in betting. Much like other successful bettors, Walters utilized analytical techniques to produce odds that were more accurate than those given by bookmakers, which led to him winning between 56-60% of all his wagers. According to ESPN, Walters found most of his success in betting on college-level sports, an area where bookmakers dedicated fewer resources to establishing their odds. Walters became known for placing substantial bets on these lesser-known teams, with one instance of him betting $250,000 on the NCAA Division I basketball team, Old Dominion, still vivid in an employee’s memory. However, Walters’ lucky streak came to an abrupt end when he was convicted of insider trading in the stock market. He was sentenced to five years in prison but ended up serving only four years thanks to a pardon from former President Donald Trump.
8. Dan Bilzerian
Unlike many gamblers on this list who have amassed their fortunes through sports betting, Dan Bilzerian has a predilection for poker. He’s gained quite a reputation through his ostentatious display of a luxurious lifestyle on social media, attributing these riches to his success in poker. Interestingly, Bilzerian is not known for participating in public games often. One of the few instances where his performance was recorded was when he finished 180th in the 2009 World Series Poker Event. Bilzerian claims that he now only engages in poker within the confines of secretive, private games. If his assertions hold, he could potentially make up to $50 million in just one night. Although there’s no concrete proof to back this claim, some professional gamblers deem it feasible considering Bilzerian’s knack for carefully choosing his opponents – usually affluent individuals he is certain he can outplay.
9. David Walsh
David Walsh’s initial encounter with gambling occurred during his tenure at the University of Tasmania, where he practiced card counting. It was during this time that he crossed paths with Zeljko Ranogajec, a fellow student. Their shared interest in gambling led them to Las Vegas to try their luck in blackjack. After returning to Tasmania, Walsh embarked on a project to create his software, aimed at forecasting horse race outcomes. This piece of technology turned out to be crucial for Ranogajec’s syndicate, known as the Bankroll. Ranogajec affirmed that in the early phases, it was Walsh who handled all the complex mathematical computations for the syndicate, utilizing his exceptional intellectual abilities. Walsh demonstrated his boldness by purchasing lottery tickets worth $11 million in pursuit of a $60 million jackpot, proving his courage matched his intellect. These days, Walsh spends most of his time managing an underground art museum he has established in Tasmania, speculated to have cost upwards of $200 million.
10. Phil Ivey
There is no questioning Phil Ivey’s poker expertise, a stark contrast to Dan Bilzerian. Ivey is widely recognized as one of the world’s premier poker players, a reputation backed by his numerous accolades, including a World Poker Title and ten World Series of Poker bracelets. His victories have not only brought him fame but also millions in prize money. Besides tournament winnings, Ivey has significantly increased his wealth by engaging in poker games against billionaires, such as the banker Andy Beal. According to some narratives, Ivey even managed to defeat Beal in a single match, securing a mind-boggling $16.6 million.
