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7 Billionaires and Millionaires Who Won Big in Gambling

Extremely wealthy gamblers are often called whales. This term refers to the large amounts of money that these gamblers bet along with their potential to bring casinos huge profits. Gambling establishments know that they can win serious money off whales. But sometimes, they also lose big to these gamblers too.

A number of millionaires and billionaires have beaten the house for large wins. These ultra-rich bettors have won fortunes off fellow poker players too. Keep reading to learn about seven billionaires and millionaires who earned big payouts through gambling.

1 – Kerry Packer Crushes the MGM Grand in Baccarat

Kerry Packer (1937-2005) was a media mogul who became one of Australia’s most influential men. But when he wasn’t running his company, Packer loved engaging in high stakes gambling sessions.Considering that he had a A$6.5 billion fortune at the time of his death, the Aussie was able to play for some massive stakes.In 1995, he was wagering $250,000 per blackjack hand at the MGM Grand. Packer’s big bets afforded him a high roller treatment like none other. MGM management cleared out eight blackjack tables and roped off the entire area. Doing so allowed Packer to move seamlessly from table to table when placing wagers.

It’s unclear why he needed eight tables, rather than simply playing up to seven hands on a single table. But the reason might have been that it gave him more privacy. Whatever the case may be, the setup definitely worked for Packer. He walked out of the MGM Grand with $20 million in profits that day.

Packer didn’t always win, though, and was just as legendary for his huge losses. He reportedly lost $28 million at London’s Crockfords casino in 1999.He played for nearly a month at the casino before finally quitting after his losing streak didn’t stop. But even a $28 million losing night couldn’t cripple the multi-billionaire.

Case in point, Packer once saw a Texas Oil tycoon bragging about his $100 million net worth at a Vegas casino. He pretended to be impressed by the man’s wealth. But then Packer took the oilman by surprise by offering to flip a coin for his $100 million fortune. Not surprisingly, the oil tycoon declined the bet.

As for Packer’s business ventures, he owned a controlling interest in Australian Consolidated Press and Nine Network television (both merged to form Publishing and Broadcasting Limited). Packer is also well known for founding the World Series Cricket in 1977. This sports organization is now known as the Australian Tri-Series.

2 – Tobey Maguire Wins Big in Poker

Tobey Maguire ($75 million net worth) cemented his Hollywood legend after starring in the Spiderman trilogy from 2002-2007. Unbeknownst to fans, Maguire’s real superpower was playing poker. He participated in an underground poker ring that featured other high-profile Hollywood stars like Ben Affleck, Matt Damon, and Leonardo DiCaprio.
These games also featured a crooked hedge fund manager named Brad Ruderman. Ruderman’s former clients sued him for $35 million in investment money that he lost in the poker games and spent elsewhere. The FBI began investigating Ruderman, at which point they uncovered the Hollywood poker ring. This ring took place at locations like the Beverly Hills Four Seasons and Viper Room on Sunset Boulevard.

Maguire was only found to have won $300,000 off Ruderman. But a report by RadarOnline brought up the possibility that he may have won $30-$40 million overall. An unnamed source said that Maguire averaged around $1 million in profits over a three-year period. “That means he could have made up to $30 to $40 million from these games,” said the source.

California law prohibits gamblers from playing in underground poker clubs. Of course, none of the famed actors were prosecuted for this light crime. As for Maguire, he’s never quite recaptured the stardom that he experienced from being Spiderman. But he has starred in movies like Brothers (2009) and The Great Gatsby (2013) since then.

3 – Newcastle Owner Mike Ashley Earns Quick Roulette Profit

Mike Ashley is worth $3.8 billion thanks to his sporting goods chain, Sports Direct, and ownership of the Newcastle football (soccer) club. He likes using his massive wealth to engage in high stakes gambling.One such session took place at London’s exclusive Mayfair casino in 2008. Ashley stepped up to the roulette table and started placing a series of bets, all dispersed around his lucky number, 17. He reportedly bet £480,000 total during the 15-minute session and won an £820,000 profit. He told the dealer, “That’ll do me, thanks very much,” before leaving the table.

The betting series that Ashley made is called a “complete,” were one bets on every combination of a specific number. “His chips surrounded the number in every possible combination, and when he won the crowd went wild and clapped and cheered,” a gambler said.

Ashley publicly displays his love of the number 17, which he wears on his Newcastle jersey whenever attending games. Regarding his Sports Direct chain, this business now features over 100 shops around the UK. Ashley used some of his profits to buy Newcastle United in 2007 for £135 million.

4 – Ben Affleck Gets Banned for Counting Cards

Ben Affleck was involved in the high stakes poker ring with Tobey Maguire. And his love of gambling extends beyond just poker, because he’s also a very skilled blackjack player. He so skilled, in fact, that he was banned from the blackjack tables at the Hard Rock Casino. Affleck won a six-figure sum while counting cards at Hard Rock.Casino management approached him and politely informed Affleck that he was “too good” for their blackjack games. As you may know, card counting isn’t illegal. But most American casinos have the legal right to refuse service to any player.

This even includes A-listers like Affleck, who was winning enough money to where the casino felt threatened. But Hard Rock didn’t ban him from their casino entirely. They invited him to play any of their other games, such as baccarat, craps, or roulette. He declined, though, because he was mainly interested in using his advantage to win money.

Of course, with a $60 million net worth, it’s not like the Batman vs Superman actor needs the money. So he gave away a six-figure amount to the Hard Rock the staff through tips.

In an interview with Vanity Fair, Affleck discussed how he became interested in card counting and worked to become an expert. “I knew with blackjack that there’s a way you can improve your odds,” he said. “And so I started trying to learn. “And then I just got to a point in my life where I’m like, ‘If I’m going to do something, I’m going to try and do it really well.’”

The only thing that Affleck seems to be missing with regard to going pro is covering techniques. Multiple reports suggests that he was being obvious when spreading his bets during favorable counts, which is why it was easy for the Hard Rock to make him as an advantage player.

The cover is blown on Affleck’s card counting skills, but he can always fall back on his acting career. He’s starred in plenty of movies, including Armageddon (1998), Reindeer Games (2000), Pearl Harbor (2001), Daredevil (2003), Runner Runner (2013), and Batman v Superman: Dawn of Justice (2016).

5 – Cary Katz Earns Multiple Big Scores in Poker Tournaments

Cary Katz has made a fortune in the student loan industry. He’s also made enough money through poker that he could be considered a pro. Katz has over $17 million in live tournament winnings. His first cash came back in 2004, and he’s continued generating a steady stream of poker results ever since.Katz’s poker career has especially been helped by the rise of high roller tournaments within the past several years. He’s won some of these events and has earned big cashes by final tabling other tourneys. His first big poker payout occurred at the 2013 PCA $100k Super High Roller, where he finished fourth place and earned $543,800. He followed this up by taking second in the same event in 2014, which earned him $653,000.

Here are some of the other big cashes that Katz has accumulated since then:

2014 WSOP $1 million Big One for One Drop – 8th place, $1,306,667
2015 Super High Roller ($25k buy-in) – 1st place, $500,000
2016 Aria Super High Roller 8 ($50k) – 1st place, $615,621
2016 Monte Carlo One Drop Extravaganza (€1 million) – 5th place, €1,750,000 ($1.93m)
2016 Super High Roller Aria Super High Roller 14 ($100k) – 1st place, $733,000
2018 PCA $100k Super High Roller – 1st place, $1,429,340
2018 Triton Poker Super High Roller Series (HK$1 million) – 2nd place, HK$13,920,000 (US$1.77m)

When he’s not crushing high rollers, Katz is running the College Loan Corporation, which he founded in 1999. The College Loan Corporation handles around $20 billion in student loan debt every year, making it America’s seventh-largest student loan company.

Little is known about Katz’s net worth. But given that he once owned a $22 million mansion in Las Vegas, he’s likely worth hundreds of millions of dollars or even billions.

6 – Dana White Makes the Palms Tap Out in Blackjack

Dana White ($500 million net worth) has been running the Ultimate Fighting Championship (UFC) and staging mixed martial arts promotions since 2001. Perhaps being around UFC fighters has rubbed off on his gambling skills, because White put the Palms casino in a armbar.This story begins with the UFC head man playing blackjack at the Palms throughout the 2000s. He was consistently one of the Palms’ most-loyal high rollers and regularly bet up to $25,000 per hand. He also dined at their expensive steakhouse, N9NE, on a regular basis and would leave servers up to $10,000 tips.

The relationship between White and the Palms seemed really solid until 2012, when he began dominating their blackjack tables. He won $2 million during one visit, which caused the Palms to halve his credit limit. Unhappy with the move, White pulled all future UFC events from the property and took his blackjack play to Caesars Palace. He commended Caesars at the time, noting that they’ll “let you play” without lowering limits.

The Palms eventually missed White and his UFC promotions. They sent him a $5,000 bottle of Domaine de la Romanee-Conti Montrachet wine to win him back — and it worked. White responded by playing blackjack and staging fights at the Palms once again. He continued his winning ways, earning $5 million in one session.

This brought up another issue, though, where White wasn’t even given bags to carry his winnings. He instead had to recruit friends to help him carry the fortune out in trash bags.

“I’m like, are you serious? We’re going to get killed,” White said. “They don’t have some kind of suitcase where they put the money in. ‘You just beat us, here you go.’ That’s really the attitude. “They just stack it all up there and go ‘thanks, have a great night.’ We’ve had trash bags, we got to the point we started bringing our own bags.”

Despite this incident, both sides parted amicably. The Palms gave White a championship belt that read “Undisputed Blackjack Champion” and “WINNER BY TKO.” “Thanks to the Palms Casino for my Championship Blackjack belt,” White posted on Instagram. “Thanks to President Todd Greenberg and all the staff. It was fun whoopin ur ass.”

7 – David Einhorn Wins Big in High Roller Poker Tournament

It’s often said that there are parallels between successful poker players and investors. And David Einhorn is living proof of this. Einhorn is one of the world’s most successful investors, laying claim to a $1.52 billion net worth. He’s also a pretty good poker player, as evidenced by the big cashes that he’s tallied.Einhorn’s first large poker tournament payout came in 2006, when he finished 18th in the WSOP Main Event. He collected $659,730 and got a lot of screen time on ESPN’s coverage of the 2006 WSOP Main Event. His next big poker windfall came at the 2012 WSOP $1 million Big One for One Drop. Einhorn took third place and collected a $4,352,000 prize.

He was eliminated by the eventual champion, Antonio “The Magician” Esfandiari. Einhorn went all-in with Ks-9c, only to be called by Esfandiari’s superior Kc-10s hand. The flop came out 9d-10h-6h, which kept The Magician in the lead. A turn card of 3h and river of Qs didn’t help Einhorn’s cause, and he was eliminated in third.

Afterward, Einhorn announced that he was donating his entire $4.35 million payout to City Year, which is a nonprofit that focuses on education. Einhorn is the president of Greenlight Capital, which bills itself as a “long-short value-oriented hedge fund.” Started in 1996, Greenlight Capital is now worth a collective $5.5 billion.

Conclusion

Casinos take their chances when playing against whales. And the seven players that I’ve discussed here all burned casinos or other gamblers at some point. The late Kerry Packer lays claim to the biggest win, when he won $20 million from the MGM Grand. Packer was playing eight blackjack tables at once and betting $250k when he earned his massive amount.Dana White also hit the house hard by winning $2 million and $5 million in separate blackjack sessions. White played so well that the Palms had to refuse his play twice. Ben Affleck is another famed player who was banned from the blackjack tables. His card counting skills were so good that the Hard Rock asked him to leave.

Mike Ashley didn’t get banned from the roulette tables after winning big at the Mayfair casino. But he did get lucky enough to take £820,000 from the luxurious London gambling venue. Sometimes high rollers win money against each other, rather against the house. Tobey Maguire, Cary Katz, and David Einhorn are all instances of poker players who’ve won millions of dollars. Maguire is especially notably, because he’s rumored to have earned between $30m and $40m from an underground poker ring.

As long as millionaires and billionaires continue betting big, there’ll always be huge winners. That being said, you can expect more of these fascinating tales in the future.

Joey Richardson