Celebrity Million-Dollar Bets – The Top 10 All-Time Winners And Losers

Posted on: August 30, 2022, 02:51h. 

Last updated on: August 30, 2022, 08:40h.

Celebrities are known for earning huge amounts of money from the music, movies, TV shows, and sporting events they entertain us with. However, they are not necessarily known for doing smart things with that money, which also entertains us. Here are our picks for the most famous bets placed by celebrities, along with their outcomes.

Michael Jordan golf
Michael Jordan, who is most certainly not to the game of golf what he was to the game of basketball, may or may not have lost more than $1 million betting on a golf game in 1991. (Image: golf.com)

10. Michael Jordan
Loss: $1.25M
Venue: Golf

There is no source for this other than a 1993 book titled Michael & Me: Our Gambling Addiction . . . My Cry For Help! by a San Diego businessman named Richard Esquinas. So believe what you will. But the author claims that he and Michael Jordan faced each other in a 1993 golf match at Aviara Golf Course in San Diego that cost Jordan $1.25M.

Our matches frequently came down to $100K putts with occasional swings of upwards of a quarter-million dollars,” Esquinas wrote. “Personally, I felt I was a controlled gambler until Michael and I went berserk in one period of approximately 10 days in September 1991, when I went from potentially more than $200K in debt to $1.25M ahead.”

Esquinas claimed Jordan fell $626K in debt from their golf wagers, then doubled down and lost again. The $1.25M debt eventually was reduced to $902K by still more golf wagers. Esquinas claimed he finally settled for $300K because he feared Jordan might not pay him the entire amount.

UFC President Dana White
Ultimate Fighting Championship President Dana White is banned from the blackjack table at the Palms Casino. (Image: lowkickmma.com)

9. Dana White
May 2014
Win: $2M
Venue: Blackjack

In 2014, Dana White — the Ultimate Fighting Championship (UFC) president worth a reported $500M — won $2M over three months playing $25K-per-hand blackjack at the Palms. The Las Vegas casino responded by halving his credit and limiting his table play to $5K per hand. They decided to ban him from blackjack at the casino a few months later.

Two years earlier, White’s blackjack credit line was similarly limited, and White responded by boycotting the Palms and taking his UFC fights, a staple for The Pearl at the Palms venue, with him. (The Hard Rock hosted the Ultimate Fighter 16 Finale on Dec. 15, 2012.)

But the icy relationship was thawed, the Las Vegas Review-Journal reported, when a new Palms chief executive eliminated White’s blackjack limits and sent White a $5k bottle of his favorite wine (2001 Domaine de la Romanee-Conti Montrachet).

The Palms tried to soften the blow this time by sending White a championship belt reading “Palms Undisputed Blackjack Champion.” White responded by stating that UFC events would still be held at the Palms. However, to date, only three more were.

Rapper 50 Cent
Rapper 50 Cent puts his money where his mouth is when it comes to his hometown football team. (Image:economictimes.indiatimes.com)

8. 50 Cent
Feb. 5, 2012
Win: $1M
Venue: Super Bowl XLVI

In 2012, 50 Cent won a cool mil by betting a cool mil that his hometown New York Giants would take the New England Patriots in Super Bowl XLVI. The Giants pulled off an upset win, 21-17.

A year before, 50 also won big by betting $500K on the Giants beating the San Francisco 49ers in the 2011 NFC Championship game, which they did 20-17.

Phil Ivey poker
Poker champ Phil Ivey reportedly bet more than a fifth of his lifetime felt earnings on a single football game. (Image: moneycasino.org)

7. Phil Ivey
Feb. 7, 2010
Loss: $2M
Venue: Super Bowl XLIV

Ten-time World Series of Poker champ Phil Ivey’s lifetime felt earnings total $9.3M. That’s a lot, but betting more than a fifth of your worth on a single event is never advisable, even if you’re betting on the favorite to win. Super Bowl XLIV belonged to Drew Brees, not Peyton Manning, and the underdog New Orleans Saints smashed the Indiana Colts, 31-17. The Colts were favored by five points, and Ivey bet on the moneyline, which would have been a smaller payout anyway.

Ivey’s bad beat made for one of the best sports headlines of the Internet era when ChicagoNow.com pronounced: “Colts Not Biggest Loser in Super Bowl XLIV.”

Charlie Sheen
Charlie Sheen has been known to take “winning” to another dimension. (Image: Getty Images)

6. Charlie Sheen
Dec. 6, 2008
Win: $1M
Venue: Boxing

In a 2012 interview with the New York Times, actor Charlie Sheen said he had a dream that Manny Pacquiao would “beat [Oscar] De La Hoya like a drum, and he did.” But when the win elicited no emotional response whatsoever, Sheen said he gave up betting.

Betting didn’t give up on Sheen, however. In 2011, at the height of his “winning,” BetUS.com offered odds of Sheen getting arrested in the next 3 months at 5:6 and of Sheen being institutionalized at 25:1.

Ashton Kutcher
After he made it big, Ashton Kutcher claimed he used his ‘dumb actor’ image to front a sports betting syndicate. (Image: giantfreakingrobot.com)

5. Ashton Kutcher
Wins: $750k
Venue: College football

Oddly, something Ashton Kutcher did while replacing Charlie Sheen in TV’s “Two and a Half Men” lands him alongside Sheen on our list. In 2013, the actor told Esquire magazine that he fronted a gambling syndicate and used his “dumb actor” persona to win huge sums of money betting on college football for half a season.

This was after he was already rich and famous!

“It was pretty fun,” Kutcher told the magazine. “Then they (the sportsbooks) caught on.”

When asked to explain the syndicate’s winning strategy, Kutcher did his best: “In football, you’re basically looking for numerical anomalies … It’s really complicated. You gotta know a lot of data points — how this team played on various surfaces, in different weather — a lot. But these guys could do it.”

Ben Affleck
Actor Ben Affleck plays a hand of blackjack with TV host Maria Menounos in this undated photo. (Image: denverpost.com)

4. Ben Affleck
Wins: $940K
Venue: Blackjack

According to the New York Post, actor Ben Affleck won $140K while playing blackjack with his pal Matt Damon at the Hard Rock Las Vegas and “gave away every one of his chips to casino staffers — tipping his dealers, waitress, and door boys as much as $5K.” A year later, Affleck reportedly won $800K at the same casino “while playing three simultaneous hands at $20K a pop.”

In April 2014, a cloud of suspicion formed over those earlier wins when the Hard Rock Las Vegas caught the future Mr. J-Lo counting cards. Because he was a celebrity, he was only banned for life from the casino’s blackjack table. (Standard practice is a ban from the casino itself.)

Affleck told Details magazine at the time: “There were a number of casinos that said, ‘Hey, you can’t play blackjack here. We know you count cards. But, you know, you’re welcome to come, do whatever you want, see a show, have dinner. We’ll comp ya. Play roulette, we know you don’t play craps. But hang out, we still want your presence and business.'”

Card counting — a method of using probability to predict the next hand — is not technically illegal. But it does not make you popular with casino managers if you’re caught.

“I mean the fact that being good at the game is against the rules at a casino should tell you something about a casino,” Affleck said. “There’s a lot of hospitality, backslapping, when they think you’re gonna come in and dump money, and if they think you might leave with some money, it’s like, ‘You know what? Why don’t you try craps or roulette?'”

Charles Barkley gambling basketball
NBA great Charles Barkley claims he has lost $10M gambling during his life but doesn’t have a problem. (Image: nbahoopsonline.com)

3. Charles Barkley
Loss: $2.5M
Venue: Blackjack

Charles Barkley most certainly did not follow his success as a basketball star with even greater success as a gambler. In a May 2006 interview with ESPN, the basketball Hall of Famer admitted losing $2.5M during six hours of blackjack one night a year earlier. He never identified which casino.

Barkley has admitted to losing a million dollars more than 30 times in his life and estimates his lifetime losses at $10 million.

“It’s stupid,” the former Philadelphia 76ers and Houston Rockets star told ESPN. “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’m not going to quit.”

In 2008, Wynn Las Vegas sued Barkley for $400K in gambling markers it extended him the year before. He paid off the debt as well as $40K in attorney fees.

Floyd Mayweather boxer
Boxing great Floyd Mayweather is one of the most daring (some would say reckless) sports gamblers in history. (Image: Instagram)

2. Floyd Mayweather, Jr.
Feb. 2, 2014
Loss: $13M
Venue: Super Bowl XLVIII

Boxing great Floyd Mayweather is alleged to have lived up to his nickname, “Money May,” in 2014. According to several internet sources, he bet $10.4M on the Denver Broncos to win the Super Bowl and $2.6M for them to lead at the half. These bets were so big, Mayweather allegedly had to place them with seven different agencies.

As most football fans remember, the Seattle Seahawks triumphed 43-8 over the Broncos, so Mayweather’s bet would have been lost. That’s if he ever placed it. The Las Vegas native, who is worth a reported $565M, never copped to placing it.

Between 2012 and 2015, Mayweather did post screen shots of his betting slips on his Instagram and Twitter accounts. Not surprisingly, most were for his winning bets. From there, we know he won $1M by betting $1.1M on the Oregon Ducks to beat the Arizona State Wildcats on Oct. 18, 2012. He also won $600K by betting $815K on the Denver Broncos to defeat the New York Jets by more than 7.5 points on Oct. 12, 2014. And a May 21, 2015, bet on the Golden State Warriors over the Houston Rockets netted him $200K before taxes.

Mayweather’s most notorious sports win would have been the payday he pocketed for placing $400K on himself to beat Conor McGregor in their Aug. 26, 2017, light middleweight bout. According to ESPN, Mayweather visited the M Resort to split the money between a bet on himself winning at -200 odds and the bout ending in under 9.5 rounds.

However, the frazzled sportsbook required time to sort out the legality of fighters betting on themselves. (The Nevada State Athletic Commission has no rules against it. However, fighters obviously cannot bet against themselves.) Mayweather reportedly got tired of waiting to place the bet and left the casino.

Pete Rose
Pete Rose’s wagering got him banned from baseball, and made him ineligible for its Hall of Fame, for life. (Image: Getty Images)

1. Pete Rose
Bets: Somewhere between $104k-$520k
Venue: Baseball

When then-Cincinnati Reds manager Pete Rose wagered on 52 games in which his own team played in 1987, the bets ($2K-$10K) were small compared to the others on this list. Yet they were the most famous and costliest celebrity bets of all time. They led to Charlie Hustle’s lifetime ban from the sport and made him ineligible for election to the Baseball Hall of Fame.

“I bet on my team every night,” Rose told ESPN Radio’s Dan Patrick and Keith Olbermann in 2007. “I didn’t bet on my team four nights a week … I bet on my team to win every night because I love my team, I believe in my team.”