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The world of casinos is very interesting and has attracted many famous stars in Hollywood and other parts of the world. Starting with Ben Affleck and blackjack up to Dana White earning $2 million in Blackjack in 2014, risk-taking is in celebrities’ blood. This trend has only been more so encouraged by the increased uptake of online casinos whereby stars such as 50 Cent who famously made a million bucks from a single sports bet can do so from the comfort of their extravagant homes. Submerging into details of these passion-light, fantastic stories, we get a firm impression that the warmth of passion to gambling never faded among the stars, the elites, where fortunes can be made or lost within the twinkle of an eye.

Michael Jordan

The following are some of the numerous bets that have been made, famously one in 1991 when Michael Jordan is understood to have lost $1.25 million in a sequence of three rounds of golf towards millionaire Richard Esquinas of San Diego. According to Esquinas’s 1993 book, Michael & Me: Our Gambling Addiction . . . My Cry For Help!, the two competed intensively and frequently betting with each putt staking as high as $100,000 and sometimes oscillations between the two reaching the level of a quarter of a million. Indeed, Esquinas described a particularly hectic time during September 1991, where he transmuted the possible debt of over $200,000 into a gain of $1.25 million. To the latter – he said that such incurred Jordan $626,000 in debt from their wagers, doubled down, and again lost. Subsequently, the debt got decreased to $902,000 with the help of further golf bets, and feeling that Jordan may not be able to pay the amount in full, Esquinas agreed to settle it to $300,000.

Dana White

In May 2014, UFC President, Dana White, estimated to be worth $500 million banked $2 million in 3 months wagering $25,000 per hand on Blackjack at the Palms Casino in Las Vegas. In response to it, the casino reduced his credit line in half and restricted the table play to $5000 per hand before prohibiting him changing his luck on Blackjack. This was not the first time that White had such restrictions put to him; he had earlier on in the year seen his credit line restricted in the same way, and in retaliation boycotted the Palms and moved UFC fights, a major agenda for The Pearl at the Palms, to the Hard Rock Hotel & Casino. 

However, this strained friendship became less sour when a new Palms chief executive erased White’s blackjack constraints and gave him 2001 Domaine de la Romanée-Conti Montrachet, his favorite wine, which costs $5000. Nevertheless, the Palms tried to temper the recent loss by giving White an actual championship belt that says “Palms Undisputed Blackjack Champion” on it; White noted, however, that UFC fights would still go on at the Palms, but to this date, only three more have occurred there.

50 Cent

In the February 5, 2012, bet, 50 Cent risked $1 million to stake his New York Giants to beat New England Patriots in the Super Bowl XLVI. Not surprisingly, a final of 21-17 in favor of the Giants was served. The above was not the first time that 50 Cent was to succeed in the online casino bets, the previous year, in 2011, he dared to bet 500,000 just to ensure the Giants stampeded the San Francisco 49ers in the NFC Championship 20-17 bet.

Phil Ivey

On February 7, 2010, ten times world series of poker champion Phil Ivey lost lots of money, $2 million to be precise, on Superbowl XLIV. Nevertheless, Rennick messed up when he wagered a 21% of his worth in one event though he had a lifetime earnings of $9.3 million. Ivey placed his money on the favorite Indianapolis Colts, while the New Orleans Saints that were led by Dustin Keller took the day with 31-17. The Colts were the favorites in this match and Ivey placed a moneyline bet which would have given him a relatively lower return had the Colts won. His substantial loss garnered major attention, leading ChicagoNow.com to famously headline: “Colts Not Biggest Loser in Super Bowl XLIV.”

Charlie Sheen

This actor of ‘Two and a Half Men’ fame was able to win one million dollars on the boxing match between Manny Pacquiao and Oscar De La Hoya by betting on the former, on December 6 2008. As reported in the New York Times Sheen himself mentioned in a recent interview that he has a dream of Pacquiao that the Filipino icon would “beat De La Hoya like a drum” which became reality. 

But the win did not make Sheen happy, therefore, he detached from betting for good. Nevertheless, the world of betting did not overlook Sheen. When the rebel comedian was almost at the pinnacle of his popular “winning” phase in 2011, BetUS.com had set the odds of Sheen getting arrested in the next three months at 5:6 while the possibility of him being institutionalized was predicted at 25:1.

Ashton Kutcher

In 2013 actor, Ashton Kutcher, who replaced the unbalanced Charlie Sheen in ‘Two and a Half Men,’ told Esquire magazine that he was running a gambling syndicate. That famous half-Swedish ‘dumb actor’ successfully gambled on college football for 500 000 dollars during half a season although he already was a millionaire and well-known in Hollywood. 

Speaking about the incident, Kutcher said it with certain excitement as far as the process was fun until the sportsbooks figured it out. When explaining the syndicate’s strategy, Kutcher highlighted the complexity involved: Football, you are looking for numerical quirks. Basically You have to know a lot of data points on how this team has played on various terrains, weather, and all sorts. But, these guys could do it.

Ben Affleck

Ben Affleck for instance was said to have walked away with $940,000 from merely playing Blackjack in the Hard Rock Las Vegas within the two seasons from 2000 to 2001. The New York Post has it that Affleck was initially dealt a $140,000 win while on the table with his friend Matt Damon; he later gave all his chips to casino workers; dealers, waitresses, and door boys to be precise, each of whom received up to $5,000. 

One year later, he scored another $800,000 at a $20,000 per hand, on three hands at the same casino. In an interview to the Details magazine, Affleck said that several casinos barred him from playing blackjack since he was counting cards, but they were happy to invite him to use their other services. A system of choosing which hand will appear in the next play, depending on the probability, is not prohibited but is not welcomed by casino managers. Affleck commented on this, noting the irony:” Since it is actually forbidden to be good at it and a casino is a casino, one cannot help but make certain conclusions.” He noted that they are friendly when you’re losing their money but turn quite unfriendly if you might start winning, saying one should rather play such games as craps or roulette.

Charles Barkley

Charles Barkley, Basketball Hall of fame player once revealed that he once lost 2.5 million in blackjack in six hours according to an interview with ESPN in May 2006, without identifying the casino. Barkley has said he has lost a million dollars more than thirty times, taking his total gambling losses to 10 million dollars. On gambling, Barkley was quoted in ESPN, “It’s stupid, it’s a bad habit, I have a problem, But, the problem is when you can’t afford it, I can afford to gamble. I didn’t kill myself when I lost two and a half million dollars, I like to gamble, and I am not going to quit”. During that year, Wynn Las Vegas sued Barkley for $400,000 gambling debts with an additional $40,000 in attorney fees.

Floyd Mayweather, Jr.

Floyd Mayweather, a greatly renowned boxing communicator, is nicknamed “Money May” and it appears this title was merited when he supposedly placed a bet of $10.4 million on Denver Broncos and an extra of $2.6 million on them to be leading at halftime during the Super Bowl XLVIII. It was also alleged that seven diverse agencies were used to place those massive bets. Nonetheless, when the Seattle Seahawks triumphed in the match against the Broncos with a score of 43-8, if Mayweather bet on the Broncos, he would have lost big time, with the said amount, which he never admitted to doing in the first place. 

Mayweather boasted his fortune estimate at $565 million between 2012 and 2015 where most of his posts were his winnings. For example, he struck the jackpot of $1 million risking $1.1 million on the Oregon ducks to win over the Arizona state wildcats on October 18, 2012. He also earned $600,000 when he wagered $815,000 on the Denver Broncos to trounce the New York Jets by more than 7.5 on October 12, 2014, and realized $200,000 before taxes based on the basketball bet on Golden State Warriors and Houston Rockets on May 21, 2015. But some complications came when Mayweather tried to bet on himself since the legitimacy of fighters betting on themselves was a controversy that posed a challenge to the sportsbook since they used a lot of time to determine the legal nature of the activity. Day finally got annoyed with the delay and left the casino without making this bet.


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