The saying goes that the house always wins; this is mostly true. But now and then a player comes along with so much skill, courage, or money that he can turn the odds on their head and make millions of dollars. Many people enjoy the occasional win, but a few have made beating bookmakers their life’s work.
1) Kerry Packer – $5 billion
Kerry Packer may have become Australia’s richest man thanks to his family’s business empire, but he will always be remembered for his gambling and that’s because Packer always played big, as you can now in Ignition Online Poker.
Part of his game included losing huge amounts of money, and Packer was known to go on some surprisingly nasty streaks during his playing career.
The most famous of these was during 10 months from September 1999 to July 2000, when he lost about $40 million gambling at casinos in Crockford, London, and the Bellagio in Las Vegas.
Luckily for Packer, he also had an occasional hot streak. Perhaps his biggest gambling achievement came in May 1995, when he won $20 million in just 40 minutes by simultaneously playing multiple $250,000 blackjack games.
2) Tony Bloom – $1.5 billion
Like many people who make their money in the world of gambling, Tony Bloom is an enigma. He studied mathematics at Manchester University and began playing poker for fun.
Over the years, this hobby has earned him about $2.5 million and allowed him to play in some major tournaments, including the World Poker Tour and Poker Million IX, where he finished second.
It was at the poker table that Bloom earned the nickname “The Lizard” for his cold-blooded playing style.
However, most of Bloom’s fortune did not come from poker. Instead, he made millions by creating his own betting consulting firm, Starlizard.
Many reports claim that Starlizard is one of the best bookmakers in the world and that it bets millions of dollars on football leagues around the world.
3) Bill Benter – $1 billion
Bill Benter is another mathematician who used his intelligence to make a fortune through gambling.
Like many young gamblers, Benter began his career counting cards in Las Vegas before focusing on horse racing in Hong Kong.
Partnering with fellow gambler Alan Woods, Benter began building an algorithm that could predict a horse’s chances of winning with incredible accuracy.
After a few difficult years and some tweaking, his model eventually earned him tens of millions a 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 a billionaire and spends his time lecturing at universities and donating to charities worldwide.
4) Edward Thorpe – $800 million
One place behind Bill Benter is the man who inspired him to gamble, Edward Thorpe – the man who invented card counting.
Using his mathematical and technological genius, Thorpe created a way to overturn the house edge 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 methods.
Published in 1962, Beat the Dealer was an incredible success with over 1 million copies sold.
Thorpe followed his book by inventing the first mobile computer. This technology gave him an increased chance of winning at roulette.
Using his stock market gambling skills resulted in Thorpe becoming rich, and he has since become an extremely wealthy man.
5) Alan Woods – $500 million
Alan Woods was a former partner of Bill Benter and made money in a similar manner.
They both started out counting cards and even worked on the same team at one point.
Then, after being blacklisted from Las Vegas casinos, they turned their attention to horse racing in Hong Kong.
After the falling out, Woods made his own model as successful as Benter’s. However, he was forced to flee to the Philippines once his bookmaking syndicate began to be investigated by law enforcement.
While still betting from his private property, Woods amassed a massive fortune of nearly half a billion dollars and worked in close partnership with former rival Zeljko Ranogajec.
6) Zeljko Ranogajec – $420 million
Known as “The Joker”, Zeljko Rangajec is another incredibly rich man who has made money for himself by being a so-called edge player.
After turning a few hundred dollars into millions at the blackjack table, Ranogajec worked with Alan Woods before creating his own betting syndicate known as Bankroll.
Focusing primarily on horse racing, the Ranogajek syndicate is said to bet more than $3 billion a year.
Even if many of them don’t win, Ranogajec still makes money thanks to bookmakers giving him discounts and discounts on his incredibly large bets.
While Ranogajec likes to keep a low profile, the fortune he has built cannot be hidden. He reportedly owns an apartment at One Hyde Park, the most expensive apartment building in the world.
What’s even more surprising is that bets placed by his syndicate appear to account for one-third of Betfair Australia’s total business.
7) Billy Walters – $200 million
Billy Walters is perhaps one of the most successful sports players in history. Walters himself stated that he had only one losing season in 39 years of betting on sports. Like many others on this list, Walters used analysis to get more accurate odds than bookmakers, allowing him to win between 56 and 60% of all bets he placed!