Celebrity Million-Dollar Bets – Top All-Time Winners & Losers

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Photo by Michał Parzuchowski

Celebrities are well-known for making a lot of money from the music, movies, TV shows, and athletic events that they put on. They are not, however, known for doing wise things with their money, which also entertains us. Do you want to know more about how celebrities spend their money when they are at an Aussie online casino? Here we are to shed some light on this intriguing topic. Let’s talk about the most famous celebrity bets, along with their outcomes.

#1 – Michael Jordan (Loss: $1.25M in 1991)

Other than a 1993 book titled Michael & Me: Our Gambling Addiction… My Cry For Help! by Richard Esquinas, there is no other source for this fact. So believe whatever you want. However, the author states that he and Michael Jordan met in 1993 during a golf match at Aviara Golf Course (San Diego), which cost Jordan $1.25 million.

“Our matches frequently were lower than  $100,000 putts, with casual swings of up to a quarter-million dollars,” Richard Esquinas wrote. “I thought I was a disciplined gambler until Michael and I went nuts in one 10-day period in September 1991, when I went from maybe more than $200,000 in debt to $1.25 million.”

Esquinas said Jordan incurred a $626,000 debt as a result of their golf bets, then doubled down and lost again. More golf wagers finally lowered the $1.25 million debt to $902,000. Esquinas claimed he eventually settled for $300,000 because he was afraid Jordan would not give him the full amount.

#2 – Dana White (Win: $2M in May 2014)

Dana White – the head of the Ultimate Fighting Championship (UFC) and a claimed $500 millionaire – earned $2 million in three months playing $25,000-per-hand blackjack at the Palms in 2014. The Las Vegas casino retaliated by cutting his credit in half and limiting his table play to $5,000 per hand. A few months later, they decided to prohibit him from playing blackjack at the casino. The situation could have been different with top online casinos from the BestAuCasinosOnline ratings.

Two years ago, White’s blackjack credit line was similarly limited, so he boycotted the Palms and took his UFC fights, which were a fixture for The Pearl at the Palms venue, with him.  The chilly relationship was healed, according to the Las Vegas Review-Journal, when a new Palms CEO removed White’s blackjack limitations and delivered him a $5,000 bottle of his favorite wine. This time, the Palms attempted to cushion the pain by giving White a title belt that stated “Palms Undisputed Blackjack Champion.” White reacted by saying that UFC events would continue to take place at the Palms. However, just three more have been completed yet.

#3 – 50 Cent (Win: $1M on Feb. 5, 2012)

50 Cent won a million dollars in 2012 by wagering a million dollars that his local New York Giants will defeat the New England Patriots in Super Bowl XLVI. The Giants won by a score of 21-17. Interestingly, 50 Cent had previously won a large sum of money by wagering $500,000 on the Giants defeating the San Francisco 49ers in the 2011 NFC Championship game, which they did 20-17.

#4 – Phil Ivey (Loss: $2M on Feb. 7, 2010)

Phil Ivey’s lifetime felt income total $9.3 million, making him a ten-time World Series of Poker champion. That’s a lot, but putting more than a fifth of your net worth into a single event is never a good idea, especially if the favorite is to win. Drew Brees led the New Orleans Saints to a 31-17 victory over the Indiana Colts in Super Bowl XLIV. 

The Colts were favored by five points, and Ivey chose the money line, which would have resulted in a lower payoff in any case. When ChicagoNow.com declared, “Colts Not Biggest Loser in Super Bowl XLIV,” Ivey’s terrible beat became one of the finest sports headlines of the Internet age.

#5 – Charlie Sheen (Win: $1M on Dec. 6, 2008)

Actor Charlie Sheen told the New York Times in 2012 that he had a dream that Manny Pacquiao would “beat [Oscar] De La Hoya like a drum, and he did.” But when the triumph evoked no emotional response, Sheen says he stopped betting. However, betting did not abandon Sheen. At the height of his “winning,” BetUS.com offered chances of Sheen being arrested within the following three months at 5:6 and odds of Sheen being institutionalized at 25:1.

#6 – Ashton Kutcher (Win: $750k in 2013)

Surprisingly, something Ashton Kutcher did while filling in for Charlie Sheen on the TV show “Two and a Half Men” landed him alongside Sheen on our list. According to Esquire magazine, the actor headed a gambling syndicate and exploited his “stupid actor” character to make large sums of money betting on college football for half a season in 2013. This was after he was already wealthy and well-known!

“It was a lot of fun,” Kutcher said to the magazine. “Then they (the sportsbooks) figured it out.” Kutcher tried his best to explain the syndicate’s winning method when asked: “In football, you’re simply searching for numerical anomalies… It’s quite difficult. You must be familiar with a large number of data points, such as how this team performed on various surfaces and in various weather conditions. But these people are capable.”

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