Red carpet to roulette wheel: The celebrity casino regulars of 2026
Million-dollar baccarat hands, World Cup bets posted for millions to see, and Hollywood poker games laid bare in a federal courtroom. 2026 has been quite a year for famous faces at the tables.
Casinos have always pulled in the rich and famous, but this year gave them plenty of new reasons. A World Cup on North American soil, a record-breaking World Series of Poker and a high-profile tax trial all put celebrities back in the casino headlines.
Some of the names below you'll know well. Others are newer to the game – from reality TV royalty learning what a flop is, to a UFC boss who now bets seven figures on the turn of a single card.
OLBG shares who has been making waves and the stories behind them. One thing worth keeping in mind as you read: These are people who can afford to lose a million dollars. The rest of us can't, and shouldn't try.
1. Dana White — the million-dollar baccarat boss
Nobody famous bets bigger, or more openly, than the UFC chief. In late September 2026, he won a single $1 million hand of baccarat at Park MGM in Las Vegas.
The story behind it is pure Vegas. YouTuber SteveWillDoIt asked White to find a casino that would take a $1 million hand. Park MGM said yes, on condition that White also put up $1 million and the pair never backed the same side. Steve lost his hand. White won his.
White said it was only the second time he'd risked $1 million on one hand. The first, at the Bellagio, went the other way. Not easy, even for him.
It tops off quite a run of table-game headlines:
- June 2025: A $1.2 million baccarat win at Fontainebleau Las Vegas, playing hands of around $300,000
- September 2025: A “60 Minutes” segment showed him betting $400,000 a hand at the Bellagio and climbing out of a $1.24 million hole
- Early 2024: By his own account, he won $26-$27 million from Caesars Palace over roughly three months
White also says some Las Vegas casinos now refuse him the limits he wants. That's a rare badge of honor for any player.
2. Drake — hip-hop's high roller (and his famous curse)
Drake is still the face of celebrity gambling, and 2026 has been his wildest year yet. He bets on Stake, the crypto casino he's partnered with since 2022, and shares the slips with millions of followers.
The big one came at the World Cup final on July 19. Drake put $1.5 million on Argentina to beat Spain in normal time, chasing a return of more than $5.1 million. It was 0-0 after 90 minutes, and Spain won 1-0 in extra time, so the bet went down.
If that sounds familiar, it should. In 2022, he lost $1 million backing Argentina in regulation time against France, and Messi's side went on to lift the trophy on penalties. Talk about history repeating itself.
His 2026 in brief:
- Lost: $1 million on the New England Patriots in the Super Bowl
- Won: About $231,000 profit on a $770,000 bet that Canada would beat South Africa at the World Cup
- Lost: $1 million on Conor McGregor, days before the World Cup final — Max Holloway won by first-round TKO, according to Revolt
- Lost: $1.5 million on Argentina in the World Cup final
Online, it's got a name: The "Drake curse," the running joke that anyone he backs is doomed. It's not all one-way traffic, mind. On his Kick return in December 2025, he landed a $1.1 million roulette payout on his lucky number 11.
3. Kevin Hart — Hollywood's High Stakes Poker regular
Kevin Hart has gone from celebrity cameo to a genuine fixture of televised high-stakes poker. He headlined two seasons of PokerGO's High Stakes Poker in 2026 alone.
Season 15, released in January, opened with Hart and Señor Tilt fighting over a $424,500 pot. In episode two, he made a sharp $35,000 river call for a $121,500 pot, but also couldn't find the fold in two expensive spots.
He was back for Season 16 in May, in a 500/1,000 no-limit game with DraftKings co-founder Matt Kalish and Andrew Robl. It started badly. His ace-king, pocket jacks and top pair all lost big pots in a single episode, before he clawed some back with jacks, trips and an ace-high bluff. That's poker — even a good hand is no certainty.
Hart's appetite for action doesn't stop at cards. His poker rivalry with Monkey Tilt founder Sam Kiki has spawned a planned $500,000 head-to-head golf match.
4. Neymar Jr. — from the World Cup to the WSOP
Neymar's love of poker is no secret, but this summer's timing raised a few eyebrows. Brazil was knocked out of the World Cup by Norway on July 5, and Neymar announced his retirement from international football. Six days later, he was at a poker table in Las Vegas.
On July 11, he entered a $10,000 six-handed event at the World Series of Poker. The WSOP welcomed him on social media and let him pose with the Main Event bracelet, but he busted without reaching the money.
Not everyone back home was impressed. Earlier in the year, while missing games for Santos, he'd already mocked critics who said poker was a distraction, joking about playing "a little poker on the phone."
With his international career over, his long-stated plan to play poker seriously after football looks closer than ever.
5. Timothée Chalamet and Kylie Jenner — Hollywood's poker power couple
Hollywood has a new poker power couple. Timothée Chalamet has long been a fan of the game, and partner Kylie Jenner has become one of its most high-profile converts.
In March 2026, Jenner fronted a Vanity Fair cover story and a viral "hot girl poker" tutorial. She said she caught the bug about two years earlier on a trip with friends, and now hosts regular games at her Hidden Hills home with Chalamet and his circle. Her favorite opponents, she said, are the ones who bet big.
Don't mistake her for an easy touch. At a Cartier poker night celebrating Chalamet's 2025 Oscar nomination — with Tobey Maguire, Kevin Hart and Kid Cudi at the tables — a GQ editor reported that Jenner beat Chalamet heads-up and was among the toughest players in the room.
The high-stakes crowd has noticed. High Stakes Poker record-holder Sam Kiki publicly offered Jenner a $500,000 seat at his table, and told her to bring Chalamet.
6. Tobey Maguire — the Spider-Man of the card room
Tobey Maguire is widely regarded as Hollywood's most formidable private-game player, and the real figure behind the ruthless "Player X" in Molly's Game. He usually keeps out of the spotlight, but 2026 dragged his poker life into a courtroom.
In January, Maguire gave evidence at the federal tax trial of Supreme Court lawyer and high-stakes player Tom Goldstein. He told jurors he hired Goldstein in 2020 to collect a $7.8 million poker debt from Texas billionaire Andy Beal.
Beal paid up in June 2020, and Goldstein earned a $500,000 fee. Goldstein was later convicted on 12 of 16 counts and sentenced to six years. Maguire faced no allegations himself.
The trial gave a rare look at just how big Maguire's games run, far beyond anything you'll see on a casino floor.
7. Caitlyn Jenner and the Celebrity Poker Tour crowd
The fastest-growing celebrity scene in Las Vegas is the Celebrity Poker Tour (CPT), played at the PokerGO Studio inside ARIA. Its third season has pulled in athletes, rappers and reality stars by the dozen.
Caitlyn Jenner made her poker debut at CPT Invitational XIII in September. She joked that she was a professional, then admitted she'd only played a couple of times and had a lesson the day before. Her feature table included former NBA guard Nate Robinson and creator Tana Mongeau.
The title went to streamer N3on in his first-ever tournament. He beat more than 50 celebrities for $15,000 and a seat in the $26,000 Super Main Event at WSOP Paradise. Beginner's luck? Possibly. Poker is like that.
Other 2026 regulars include Super Bowl champions Skyy Moore and Antoine Winfield Jr., UFC champions Henry Cejudo and Aljamain Sterling, and rappers Waka Flocka Flame and Ray J.
8. Charles Barkley — still candid, still betting
Charles Barkley is still the most honest gambler in sports. He's told Shannon Sharpe he lost around $25 million over his lifetime, and has joked that he wants some of his ashes scattered in a Las Vegas casino.
Moderation only goes so far. On a truTV hockey broadcast, Barkley revealed a sizeable bet on the Toronto Maple Leafs and suggested he needs a bookie for bets too big for his FanDuel account.
His openness about the losses, from a notorious $2.5 million blackjack session to a $400,000 casino marker dispute with Wynn Las Vegas in 2008, keeps him a folk hero among Vegas regulars. And it's a useful reminder that even the biggest names lose, and lose big.
Fame doesn't beat the house
The celebrity casino scene looks very different from a few years ago. The quiet VIP salons are still there, but now they share the stage with livestreamed baccarat hands, bet slips posted to Instagram and poker games broadcast on PokerGO.
From Dana White's seven-figure baccarat and Drake's World Cup heartbreak to Kevin Hart's televised swings and Kylie Jenner's poker nights, the lesson is the same one every punter learns sooner or later. Fame and fortune give you no protection from the cards. For every spectacular win, there's a loss just as big. They just don't always make the headlines.
Please gamble responsibly and only bet what you can afford to lose. If gambling stops being fun, free support is available from GamCare and GambleAware.
This story was produced by OLBG and reviewed and distributed by Stacker.
