Who are the biggest celebrity gamblers?

What is it about the gambling exploits of others that peaks our interests?

Casino take downs like Don Johnson in Atlantic City. The behemoth amounts gambled by whales like Packer, Khashoggi and the Sultan. Always fascinating reading.

Throw bona fide celebrity status into the mix and our interests are certainly not dulled. Here’s a list of very well known celebrities known to love a big punt.

Michael Jordan

In an interview with Ahmad Rashad, Jordan addressed gambling addiction rumours stating that he didn’t have a gambling problem but a rather a, “competition problem.”

Gambling was just a bi-product of the competition addiction. There was plenty of it on all manner of things – golf, poker, blackjack, basketball (speculated but denied by Jordan). He was even known to bet with team mates on whose luggage would appear first at baggage claim.

His bets on the golf course were the stuff of legend, including one during a round at Sunningdale with Gary Lineker and his mate and former European tour pro ‘Queeny’.

On the first tee Queeny asked Jordan if he’d care to have a wager on the round, which Jordan did of course. ‘So how much would you like to play for?’ asked Queeny. To which Jordan, after a long and considered puff on his cigar, replied, ‘Whatever makes you feel uncomfortable, man.’

John Daley

Over a 16 year period from 1991 to 2007 John Daley gambled a lot. Blackjack sessions betting $15,000 a hand and playing all 7 hands at the table were his jam. He admits to one session that lasted 2 days.

He knew that he had lost a lot of money over that time, but it wasn’t until he went through tax records to tally exact losses that he realised just how much. “I was shocked. I though it might have been 20-25 but I had no idea it was 55-57 million. It’s crazy”. 

Incredibly, Daley has no regrets. “I should say I regret it but I did it you know, I move on from it. I had a lot of fun doing it.”

 

Ben Affleck

Ben Affleck is a rare commodity. A celebrity known to gamble big money and often. But known to win more often than not.

One of the earliest reports of Ben Affleck’s gambling activities dates back to 2001 when he and then-girlfriend Jennifer Lopez visited the Hard Rock Hotel & Casino in Las Vegas. Affleck reportedly won $800,000 playing blackjack over 2 days during this trip. Hard Rock subsequently banned him from their casino – a badge of honour for a legit advantage player.

In 2004, Affleck participated in the California State Poker Championship and won the No-Limit Texas Hold’em event, taking home $356,400. This victory showcased Affleck’s poker skills and brought attention to his involvement in the poker world. That involvement has continued with regular tournament appearances, many of them successful. His poker chops have won the praise of pros like Phil Hellmuth.

Floyd Mayweather Jr.

Floyd’s gambling style is less about skill and more about bravado. He’s famous for placing enormous bets on sporting events and sharing images of his betting slips on social media – bets that often reach seven figures.

In 2014, Mayweather made headlines when he claimed to have bet $10 million on the Denver Broncos in Super Bowl XLVIII. However, after the Broncos lost to the Seahawks Mayweather later stated that he didn’t actually place the bet, claiming it had been more of a publicity stunt.

Mayweather frequents Las Vegas where he enjoys rounds of blackjack and poker. You can just see casino VIP concierge services racing to the airport when Floyd is expected in town.

Tobey Maguire

Tobey Maguire of Spider Man fame was known to be part of exclusive and high-stakes poker games that took place in Los Angeles and occasionally in other locations. These games, sometimes referred to as Molly’s Game were organised by Molly Bloom, who ran high-stakes poker games that attracted celebrities, business tycoons, and professional poker players.

In 2011 Bloom published a memoir detailing her experiences running these games, which formed the basis of the  movie Molly’s Game. One of the regulars at her games was a person identified in the memoir and movie only as Player X (played by Michael Cera). Player X was an obnoxious personality with a ruthless desire to crush his opponents regardless of consequences. Player X has since been confirmed to be Tobey Maguire.

Tobey Maguire faced legal scrutiny related to his involvement in these underground poker games (don’t think the revelation that he was a prize S.O.B helped his career much either). The actor, along with other players, was sued for winnings that were allegedly derived from illegal gambling activities. Maguire reportedly settled the lawsuit by paying a significant amount, although the exact details of the settlement were not publicly disclosed.

Alan Iverson

Alan Iverson enjoyed one of the all-time NBA careers with honours including the league MVP in 2001, 11 time All-Star, 1997 Rookie of the Year and being names 3 times in the All NBA First Team. It’s a career that earned him over $200 million in salary and endorsements. But within 2 years of his final year playing with the Philadelphia 76ers, Iverson was reportedly broke thanks largely to his gambling habits.

He has been banned from multiple casinos in Las Vegas and Atlantic City (wonder if they waited until he was broke before banning him?). He now suffers the ignominy of making internet lists like, the top 5 richest NBA players who are now broke.

Shannon Elizabeth

American Pie made Shannon Elizabeth famous. Her skills on the poker table have kept her in the spotlight – for all the right reasons.

Elizabeth had a notable performance in the 2005 WSOP Main Event. She finished in 25th place out of a large field stacked with poker talent, demonstrating that she had more than just casual interest and could compete at a high level in professional poker tournaments.

Charles Barkley

Barkley has openly acknowledged his affinity for gambling and has referred to it in interviews and public discussions. No point denying it when misadventures are being reported in the papers. Like in 2008, when he was forced to pay a significant fine after being caught in a Las Vegas casino attempting to avoid repaying a $400,000 gambling debt.

Losses by his own admission are massive. Biggest single session loss: $2.5 million after 6 hours of blackjack. Number of $1 million plus losing sessions: 30. Lifetime net loss position: $10 million (give or take).

At least there have been some wins along the way.

Leonardo DiCaprio

Leo is too preoccupied chasing young ladies to worry about spending too much time gambling, and perhaps isn’t a justifiable inclusion on this list. But he was a Molly’s Game regular back in the day.

Unlike fellow actor Maguire, Leo’s playing style was more social, less sociopath.

Tiger Woods

Tiger gets a mention in most conversations about celebrities with a propensity to gamble big. He’s a regular at Vegas known for playing blackjack at $25,000 per hand. Big bets to be sure. But relative to his vast wealth, arguably quite conservative amounts to wager.

According to Forbes, as at October 2023 the world had 4 billionaire athletes. Tiger was one of them, so his gambling needs to be put in perspective. So too should Michael Jordan’s who tops the group of 4 with a net worth of $3 billion.

Charlie Sheen

What do you get if you cross the biggest pay check on television, the mother of all substance abuse problems, a pathological belief you’re always winning at everything and a fondness for spending time in Vegas? Probably significant gambling losses.

Sports betting was Charlie’s go-to, with weekly wagers in the tens of thousands and one reported wager of $1 million. Details will always be hazy. After all, in his ‘rock star from Mars’ hey day Charlie was, in his own words, ‘bangin’ seven-gram rocks and finishing them because that’s how I roll, because I have one speed, one gear – GO!’

Phil Ivey

Is Phil Ivey a celebrity who gambles, or a gambler whose gambling exploits have earned celebrity status? Probably the later. But he still deserves a place on this list.

Ivey has won 10 World Series of Poker (WSOP) bracelets, showcasing his dominance in various poker variants. His bracelet victories span different games, including No-Limit Hold’em, Pot-Limit Omaha, Seven-Card Stud, and more. He has also made it to the final table of the WSOP Main Event three times (2003, 2009, and 2012), demonstrating his consistency and prowess in the most prestigious tournament in poker.

But it’s Ivey’s play on hight-stakes cash games after tournaments end that are legendary, winning astronomical amounts from ultra high net worth amateurs wanting to test their skills against the best.

He has also inflicted pain on casinos. He once won £7.8 million playing baccarat at Crockfords Casino in London using a technique known as edge sorting.