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History's High Rollers: The Top 7 Biggest GamblersBy GamblersPick Apr 07, 2020Experience the thrill of gambling through history's biggest gamblers. We share tales of massive high rollers, whales, and richest gamblers.
There's something thrilling about gambling. The excitement, strategy, and prospect of winning bigkeep billions of gamblers coming back for more.
Even if you've never won a huge windfall, you've likely heard stories of some of the world's biggest gamblers and their earnings. And it's stories like these that keep the hope alive.
But not all high rollers are successful. They say you have to play big to win big and some of these whales did exactly that.
Are you ready to learn more about the biggest wins, losses, and most impressive highrollers in gambling history?
Put on your poker face and let's get started!
1. Kerry Packer
An Australian media mogul, Kerry Packer had the funds to support his gambling habit and he wasn't afraid to show it. Packer was most well known for establishing the World Series Cricket which might explain his affliction to sports gambling.
While Packer had his fair share of large winnings, he also incurred some major losses. One of his most notable and painful hits came after gambling nearly $25 million on four roulette tables and losing everything. It was also common for him to bet nearly half a million dollars on a single blackjack hand.
Not only is Packer known as one of the biggest gamblers in history, but also one of the most generous with his winnings. It was reported that Packer left waitresses seven-figure tips after a good night at the casino.
2. Terrance Watanabe
It's all in the name. Terrance Watanabe was exactly that -- a wannabe. A former millionaire, Wantanabe holds the record for the biggest losing streak in Vegas history!
In 2007 alone the high roller lost almost $127 million at the casino tables of Caeser's Palace and the Rio. But Watanabe struggled to accept his shortcomings. He's currently in a legal battle with Harrah's for nearly $15 million.
Watanabe claims the casino fed him too many drinks and even slipped him pain medication to trick him into playing and gambling all of his money away.
3. Edward Thorp
Switching gears from some of the biggest losers to some of the biggest winners, introducing Edward Thorp. Some argue that Thorp is a genius. He is, after all, a successful math professor and author of a book on how to count cards.
Thorp's book entitled Beat the Dealer explains how to use mathematics to beat the house and improve your odds at the blackjack tables. Before writing the book, Thorp tested his methods in Las Vegas, Reno, and Lake Tahoe where he won $11,000.
Card counting is illegal and casinos are constantly on the lookout for violators. It's reported that Thorp actually wore disguises to keep the casinos on their toes and avoid detection.
But Thorp didn't use his knowledge just at the card tables. He was also quite successful when gambling on backgammon, roulette, and Baccarat.
4. Billy Walters
Some people chalk up years of winning to a lucky streak. The same can't be said about this successful gambler. Billy Walters is one of the most successful sports betters in history, consistently raking in big wins for over 30 years.
Walters bet on major league sports including the NBA and NFL but also enjoyed trying his odds at college football. His talent even helped him score a $3.5 million win on Super Bowl XLIV.
Another reason so many gamblers look to Billy Waters for inspiration is because of his not-so-successful beginnings. Growing up in Kentucky, Walters was raised by his grandmother after his father died and his mother abandoned him at the age of two. It was the classic rags-to-riches story.
Sadly, even a 30-year long winning streak isn't a guarantee. At one point, Walters spent five years in prison for insider trading.
5. Archie Karas
No biggest gamblers list would be complete without the mention of Archi Karas. Arguably the best gambler of all time, Karas has had plenty of ups and downs along the way.
Archie's love of gambling and winning money began when the Greek-American was waiting tables in the States. He played coworkers and customers in a variety of money games and quickly learned he had a knack for gambling.
This hobby turned into a love for poker, where Karas earned nearly $2 million. He quickly lost his millions and was left with just $50 to his name.
Most well-known for his Vegas winning streak of the 1990s, Karas took that $50 and turned it into $40 million! This streak went down in the history books as the largest and longest winning streak of all time.
Unfortunately, as most famous gamblers seem to do, Karas lost his earnings over the course of a few more years. He racked up countless losses in dice, poker, and baccarat.
Karas' bad luck continued and in 2013 he was arrested for marking cards at a California casino.
6. Phil Ivey
When it comes to being the poker king, only one man deserves the title -- and that's 10-time World Series of Poker winner Phil Ivey.
But poker isn't Ivey's only claim to fame as one of the biggest gamblers of all time. Ivey also won $11 million playing baccarat in London. The problem was, his earnings may not have been legitimate.
Ivey was accused of being involved with an edge-sorting scheme. Edge sorting involves studying the deck and looking for inconsistencies and identifiable markings on the backs of the cards. Players use this information to predict whether or not the faced-down cards are high or low.
The casino where Ivey earned his biggest winnings refused to pay due to suspicion of cheating.
But the London casino wasn't the only one that took issue with Ivey's techniques. The Borgata in Las Vegas also accused Ivey of edge-sorting and the courts later ruled in favor of the casinos.
7. Chris Moneymaker
With a name like Moneymaker, it's no wonder this high roller goes down in history as one of the biggest gamblers of all time.
Chris Moneymaker is most well known for winning the Main Event in the World Series of Poker in 2003. What makes his story unique is the fact that Moneymaker gained entry to the elusive competition on the internet. The poker phenom went on to turn his $40 entry fee into a $2.5 million haul.
Moneymaker's entry into the Series and his impressive win transformed the game of online poker. He also went on to write a book about his experience entitled Moneymaker: How an Amateur Poker Player Turned $40 into $2.5 Million at the World Series of Poker.
It's interesting to note that Moneymaker's buy-in fee was actually $86 not $40 as the book title suggests -- a detail that the author claims he forgot.
In total, Moneymaker has raked in over $3.5 million and continues to earn money playing poker to this day.
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