It has long been argued if winning at gambling relies more on chance or aptitude, yet we can’t overlook the fact that, from time to time, a gambler comes along with the right combination of daringness, expertise, and resources that allows them to beat the odds and amass serious wealth in the process.

If you are curious about the biggest winners in the gambling world, keep reading. Below are six of the wealthiest players, their road to success, and their record-breaking wins.

Edward O. Thorp ($800 Million)

Edward Thorp is acclaimed for his innovation in the game of card counting and put his mathematical and technology competencies to work, engendering a strategy to rise beyond the house edge in blackjack. His first attempt was profitable, allowing him to take away a win of $11,000. In 1962, he went on to make public “Beat the Dealer”, unveiling his technique in detail.

Thorp kicked his gambling skills up a notch by building the world’s first computerized device to fit on the body. This enabled him to make more profitable bets in online roulette games. His success in this arena propelled him even further – into the stock market and, subsequently, a life of consistent wealth.

Zeljko Ranogajec ($441 Million)

Zeljko Ranogajec, renowned for his aptitude in advantage gambling, accomplished greatness through horse racing and playing blackjack with real stakes. Boasting a total wealth of $610 million AUD (equivalent to over $450 million USD in 2021), he was given the exclusive honor of induction into the Blackjack Hall of Fame in 2011.

After earning his degree in tax, finance, and banking at the University of Tasmania, Zeljko adopted a curious passion – card counting. Soon after, the Australian casinos barred him from their premises and he moved to the US to pursue his newfound talent. When his luck ran out and he was again banned from Vegas, he returned home and made a fortune through horse betting.

Alan Woods ($500 Million)

Having established himself as a leading professional gambler, Alan Woods’ legacy remains influential today. His extraordinary wealth of AU$670 million (~$500 million) at the time of his passing in 2008 is still among the highest of any gambler in the world.

Beginning his studies in mathematics at the University of New England in Australia, Alan soon found himself leaving behind the textbooks and turning to games of chance. His attempt at the poker machines only netted limited profit, but it was his foray into the card game bridge that allowed him to acquire the card counting skills possessed by more experienced players.

Over the course of three years, Alan established himself as a professional blackjack gambler before retiring and becoming part of a team with Bill Benter.

Bill Benter ($1 Billion)

Bill Benter, who is certainly considered the world’s most successful bettor, has built up an incredible reputation in the horse betting scene. He initially gained recognition for his proficiency in blackjack, but it was when he teamed up with Alan Woods that he truly rose to fame. Together, they developed a highly accurate algorithm which allowed for precise predictions on a horse’s potential to win a race.

Following the bumps in the road and making improvements to their framework, Benter’s system eventually produced yearly revenue in the tens of millions.

Bill’s well-known success story originated with his accurate prediction of the Triple Trio in Hong Kong, a bet in which the 3 horses to finish first must be chosen correctly from three separate races.

Tony Bloom ($1.7 Billion)

Tony ‘the Lizard’ Bloom is well-known for his keenness in poker and sports gambling. Stepping into the limelight, he has earned a great fortune through various business opportunities, but his gaming skills remain undoubted sources of his financial success.

From gambling to property investment; the charismatic Bloom has been a presence throughout numerous fields. His involvement in the World Poker Tour further attested his passion for modern card games, eventually leading to him founding his very own gambling websites.

Kerry Packer ($5 Billion)

Kerry Packer sits atop the ranking of Australia’s affluent persons due to the expansive business enterprise of his family. Nonetheless, it is his gambling investments that characterize his remembrance, chiefly as Packer was never a stranger to taking risks.

Taking on big risks can lead to heavy losses, something Packer learned firsthand during his time spent as a high stakes gambler. Though there were triumphs throughout the journey, there were also some devastating setbacks.

During a period of ten months, from September 1999 up to July 2000, one of his biggest financial downturns happened when he lost an estimated amount of $40 million at both Crockford’s casino in London and the Bellagio in Las Vegas.

Packer’s incredible gambling success was highlighted in May of 1995 when he rocketed to the top of the charts in a mere forty minutes, holding a staggering $20 million.

Honorable Mentions

Apart from these professional gamblers and bettors, there are also some other recognized players in the gambling and betting scene, such as:

• Phil Ivey
• Sam Farha
• Amarillo Slim
• Billy Walters
• Dan Bilzerian

Gambling, though no shortcut to financial prosperity, has enabled a few to make a significant additional income. Yet, it remains a business for those that take it seriously, and not just for instant riches.