They say that the house always wins, but ask the richest gamblers in the world and they will tell you that at some point in their lives, they beat the house and walked out with some of the biggest winnings in gambling history. 

Make no mistake, these people are not amateurs – they are, or were, experienced gamblers who were willing to take risks, and their risks paid off.

Regardless of their chosen game, they knew it well. They were cunning and skilled, they started with vast amounts of money to gamble, and they kept playing until they won life-changing amounts. 

Kerry Packer, Tony Bloom, Bill Benter, Edward Thorp and Alan Woods – who were these people, and how did they become good enough to walk away with millions of dollars from the gambling table? 

What did Zeljko Ranogajec, Billy Walters, Dan Bilzerian, David Walsh and Phil Ivey do that gave them an edge and allowed them to beat the house, sometimes time and again?

Many gamblers participate for fun. Secretly, though, it’s fair to say that all gamblers hope to walk away with enough money to make a difference in their lives. 

These sorts of winnings don’t happen very often, but read on to find out about some of the most impressive gambles in history.

You never know, you may learn a thing or two for your next session at the casino. 

Kerry Packer

Kerry Packer lived large – he often gambled large sums of money and lost, but this didn’t slow him down. Between September 1999 and July 2000, Packer gambled away $40m in casinos in Las Vegas, London and Australia. 

He bided his time, and the tides changed. When he got on a hot streak, it was a really hot one, and in May 1995, he won an eye-watering $20m in just 40 minutes playing a few blackjack games simultaneously. 

Packer was an Australian media mogul, a powerful man who had a controlling interest in the Nine Network. He owned Australian Consolidated Press and had an interest in World Series Cricket.

Born in 1937, he struggled in school because of dyslexia but was an avid sportsman, playing rugby and cricket. He was also well-known for his boxing skills. 

After his father died, he inherited $100m, which he went on to invest in various businesses. 

Packer was known for taking on some of the richest and best gamblers in Las Vegas and casinos in Europe, and he often bet millions of dollars. He wasn’t afraid to lose, and he had faith that sooner or later, his luck would change. It did, and he went down as one of the biggest gambling winners in history, winning approximately $5bn in the course of his life.

Tony Bloom

Born Anthony Grant Bloom in 1970, this Englishman has always been a bit of a mystery. Very little is known about his life. It appears that he studied at the University of Manchester, and it may be around that time that he started playing poker for fun. 

His first big win was in the Australian Poker Championship in 2004. He walked away with $320,000. He went on to win several tournaments, and in 2005 he scooped more than $350,000 in the No Limit Hold’em VC Poker Cup. 

It is difficult to calculate how much he has won over the years, but poker enthusiasts say that it could be as much as $1.5bn. His tournament winnings alone are nearly $4m, making his winning some of the richest gambles ever.

Bill Benter

This American gambler was also a math whizz, and he used his aptitude to rake in big bucks on gambling tables. 

Born in 1957, Bill Benter knew from an early age that he had a gift that most people do not possess. He was highly gifted in math and physics, and he decided to take his skills to Vegas where he got a job as a card counter. 

The story goes that he improved his gambling skills by reading a book by Edward Thorp, another avid gambler who went on to rake in millions (more on him later). 

Benter met Alan Woods, another expert gambler who specialized in horse races, and the two became a force to be reckoned with. Together, they moved to Hong Kong in 1984 where they decided to create a formula for choosing winners. 

Using his math genius, Benter created a statistical model that he believed could lead to successful predictions, and they used this software to win more than $600,000 in 1988. In 1999, they pocketed $3m in profits. 

Benter has made most of his money from his mathematical model, which experts believe earns him tens of millions of dollars every year. He is predicted to have earned approximately $1bn in gambling and continues to place bets that bring in big wins. 

He is now a visiting math professor at Southampton Management School, and he is also a philanthropist and founder of the Benter Foundation. 

Edward Thorp

Edward Thorp wrote the book that Benter read to become an expert gambler, and he has shared his gambling expertise in various other books that are popular in the gambling community. 

Thorp made significant waves in the gambling industry by leading computer-aided research in blackjack. 

Born in Chicago, Thorp moved to California, and as he grew older he discovered that he had an aptitude for the sciences. He would create original experiments, and it led to scholarships for his chemistry and physics knowledge. 

In the course of his life, he made more than $800m, which he invested in the stock market and went on to become a very wealthy man. 

Alan Woods

Remember him? He partnered with Bill Benter and together they went to Hong Kong, created a system, went on to successfully predict many horse races and made lots of money. 

Just like Benter, Alan Woods started as a card counter but was eventually blacklisted in Vegas. After Woods and Benter won fortunes in Hong Kong, they fell out and parted ways. Woods went on to become a highly successful gambler in his own right. 

At some point, he settled in the Philippines but was forced to flee when the authorities started to investigate his gambling activities. 

He is one of Australia’s most famous gamblers, and after a lifetime of successful gambling and total winnings at around $500m, he died of cancer in 2008. 

Zeljko Ranogajec

Zeljko Ranogajec is also known as the Joker and he claims to be an advantage gambler. He set up a gambling syndicate known as the Bankroll after he transformed a few hundred dollars into millions playing blackjack. 

Today, he is largely focused on horse racing, and it is estimated that his syndicate places bets worth more than $3bn every year. 

Ranogajec has a diversified portfolio. Apart from horse racing, he also makes money from discounts offered to him by bookies because of his large bets.

Although he is a private man about whom not much is known, his wealth often gives him away, and he is to reputed have won more than $420m and to own an apartment in the most expensive building in the world. 

Billy Walters

Billy Walters’ game is sports betting and it has made him one of the richest men in modern gambling history. According to Walters, he has only lost one gambling season in the course of his life. It is estimated that he wins between 50% and 60% of all the bets he places. 

Walters decided to focus on college sports, which are often overlooked by bookies. Because of his track record, lots of people believe in him, and he has placed bets as big as $250,000 for his clients. 

Unfortunately, he found himself behind bars, sentenced to five years for insider trading, but he was pardoned by Donald Trump after only serving four. Walters has won more than $200m.

Dan Bilzerian

Dan Bilzerian’s expertise is poker, and he is well-known for his social media antics and extravagant lifestyle. He claims that everything that he has comes from poker, but despite his public persona, he never plays in open tournaments.

He says that he prefers to play in private against other rich poker players and has allegedly made millions of dollars like this. According to him, he can make as much as $50m in one night.

In his one public appearance, he came 180^th in the World Series of Poker tournament of 2009. He has won over $200m.

David Walsh

David Walsh started as a card counter, but not in Las Vegas. He was working in casinos in Tasmania when he realized that he had a knack for gambling. 

Walsh did, however, eventually come to Vegas. Here, he met and became friends with Zeljko Ranogajec and they decided to play blackjack together. 

He eventually went back home, where he decided to develop software that could predict winners in horse races. This software would eventually become instrumental in Ranogajec’s syndicate, the Bankroll. 

Apart from his highly mathematical mind, Walsh is also known for taking big risks. He once bought lottery tickets worth $11m to try to win a $60m jackpot. 

He still lives in Tasmania, where he runs his underground art museum. It is estimated that Walsh has won $200m.

Phil Ivey

Phil Ivey is considered one of the top poker players in the world today, and his matches are public for all to see. He has won lots of trophies and awards, including one World Poker Tour title and 10 World Series of Poker bracelets. 

Although most of his wealth comes from winning tournaments, he has made a tidy sum playing against billionaires. According to one unconfirmed story, he won $16.6m playing against banker Andy Beal. It’s suggested that Ivey has won approximately $100m.

It takes a combination of wealth, smarts, resilience and risk-taking to become one of the richest gamblers of all time. Remember, as much as you want to emulate the rich gamblers discussed here, you should never bet on money that you cannot afford to lose.