The saying goes that the house always wins and for the most part, it does.
But every now and again, a gambler comes along with so much skill, bravery, or money that they can turn the odds on their heads and make millions of dollars in the process.
Lots of people like the occasional flutter but there are a few individuals who have made beating the bookies their life’s work.
Read on to discover how they became the richest gamblers in the world and what they won in the process.
1. Kerry Packer – $5 Billion
Kerry Packer might have become Australia’s richest man through his family’s business empire, but it’s gambling that he will always be remembered for. This is because Packer always played big.
Part of playing this way is losing huge sums of money and Packer was known to go on some astonishingly bad streaks during his gambling career.
The most famous of these was over a 10-month period from September 1999 to July 2000 when he lost around $40 million playing in both Crockford’s casino, London and the Bellagio in Las Vegas.
Fortunately for Packer, he also had the occasional hot streak. Perhaps his greatest gambling achievement came in May 1995 when he won $20 million in only 40 minutes by playing several games of $250,000 stake blackjack at once.
2. Tony Bloom – $1.5 Billion
Like a lot of people who have made their money in the gambling world, Tony Bloom is a bit of a mystery.
What we do know is that he studied mathematics at The University of Manchester and started out playing poker for fun.
Over the years this hobby has won him around $2.5 million and has seen him play in some huge tournaments including the World Poker Tour and Poker Million IX where he finished second.
It was also at the poker table that Bloom earned himself the nickname “The Lizard” for his cold-blooded style of play.
Most of Bloom’s fortune has not come from poker though. Instead, he has made millions by setting up his own betting consultancy firm, Starlizard.
Many reports say that Starlizard is one of the top betting firms in the world and that it wagers millions of dollars on soccer leagues across the globe.
3. Bill Benter – $1 Billion
Another math whizz who has used his intelligence to earn a fortune by gambling is Bill Benter.
Like a lot of young gamblers, Benter started his career counting cards in Las Vegas before turning his attention to horse racing in Hong Kong.
In partnership with another gambler, Alan Woods, Benter began building an algorithm that could predict a horse’s chance of winning with incredible accuracy.
After a few difficult years and some tweaking, his model eventually began to earn him tens of millions of dollars per year.
Benter’s most famous win came when his model correctly predicted the Triple Trio, a famous bet in Hong Kong where you must predict the first three horses to cross the line in three separate races.
Today, Benter is now a billionaire and spends his time giving lectures at universities and donating to charitable causes around the world.
4. Edward Thorp – $800 Million
Coming in one place behind Bill Benter is the man who inspired him to gamble in the first place, Edward Thorp – the man who invented card counting.
Using his mathematical and technological genius, Thorp created a way of overturning the house advantage when playing blackjack.
During his first weekend trying the technique he won $11,000 and after seeing that it was effective, he decided to publish a book explaining his techniques.
Published in 1962, “Beat the Dealer” was an incredible success with over 1 million copies being sold.
Thorp followed his book by inventing the first wearable computer. This piece of technology gave him increased chances of winning roulette.
Taking his gambling skills to the stock market saw Thorp’s wealth balloon and he has been an extremely wealthy man ever since.
5. Alan Woods – $500 Million
Alan Woods was a former partner of Bill Benter and made his money in a similar way.
They both started out counting cards, and even worked on the same team at one point.
Then, after being blacklisted from the Las Vegas casinos they turned their attention to the Hong Kong horse races.
After falling out, Woods made his own model every bit as successful as Benter’s.
However, he was forced to flee to the Philippines once his betting syndicate started being investigated by law enforcement.
Still betting from his private property, Woods amassed a huge fortune of around half a billion dollars and worked in close partnership with former rival Zeljko Ranogajec.
6. Zeljko Ranogajec – $420 Million
Known as “The Joker”, Zeljko Ranogajec is another incredibly rich person who has made money for himself by being a so-called advantage gambler.
After transforming a few hundred dollars into millions at the blackjack table, Ranogajec worked with Alan Woods before setting up his own betting syndicate known as the Bankroll.
Mainly focusing on horse racing, Ranogajec’s syndicate is said to place bets worth over $3 billion per year.
Even if many of these don’t win, Ranogajec still makes money thanks to bookmakers giving him discounts and rebates on his incredibly large bets.
While Ranogajec likes to keep himself to himself, the fortune he has built cannot be so easily hidden. He reportedly owns an apartment at One Hyde Park, the world’s most expensive apartment building.
Even more amazingly, bets placed by his syndicate apparently make up one third of Betfair Australia’s total operations.
7. Billy Walters – $200 Million
Billy Walters is perhaps one of the most successful sports bettors in history. Walters himself has gone on record saying he has only had one losing season in the 39 years he gambled on sports.
Like many others on this list, Walters used analysis to produce more accurate odds than the bookies, allowing him to win between 56-60% of all bets he placed.
According to ESPN, Walters found most of his success at collegiate level sports where the bookies invested less time and resources in calculating their odds.
Apparently, Walters used to bet huge amounts of money on these small teams with one employee recalling a $250,000 wager he placed on NCAA Division I basketball team, Old Dominion.
Unfortunately for Walters his lucky streak came to an end when he was found guilty of insider trading on the stock market.
He was sentenced to five years in prison, only serving four thanks to pardon by former President Donald Trump.
8. Dan Bilzerian – $200 Million
While most gamblers on this list have made their money through sports betting, Dan Bilzerian tends to prefer the poker table.
Most people will have heard of Bilzerian thanks to his antics on social media where he flaunts a lavish lifestyle, which he says he earned through poker.
What’s interesting is that Bilzerian hardly ever plays public games. In fact, one of his only recorded results was 180th in the 2009 World Series Poker Event.
Bilzerian maintains that he now only plays poker in underground, private games. And, if you believe him, Bilzerian can earn up to $50 million in one night.
Of course, there is no way of proving this, but some professional gamblers think it is a possibility, given that Bilzerian has a reputation for only playing against super rich people he feels sure of beating.
9. David Walsh – $200 Million
David Walsh first became involved in gambling when he counted cards during his time at the University of Tasmania.
Here he met fellow student Zeljko Ranogajec and the two of them soon decided to try their hand at playing blackjack in Las Vegas.
When Walsh moved back to Tasmania, he began building his own software to predict the outcome of horse races. This would end up being a key piece of technology for Ranogajec’s syndicate the Bankroll.
According to Ranogajec, during these early days Walsh would be the one to do all the mathematical calculations for the syndicate because of his intellectual gifts.
Walsh matched this intelligence with bravery and once bought $11 million worth of lottery tickets to win a $60 million jackpot.
Today, Walsh dedicates most of his time to an underground art museum that he has built in Tasmania.
The rumored price tag? Over $200 million.
10. Phil Ivey – $100 million
Unlike Dan Bilzerian, there can be no doubting Phil Ivey’s poker playing ability.
A lot of people see him as one of the best players in the world and he has the trophies to prove it, including a World Poker Title and 10 World Series of Poker bracelets.
These victories have come with millions of dollars in prize money, but Ivey has also made huge sums by playing poker against billionaires like banker Andy Beal.
According to some stories, Ivey is supposed to have beaten Beal out of $16.6 million in one single game.