Biggest Casino Winners: Celebrities Edition
Hollywood’s Biggest Casino Winners and Their Legendary Wins
The Rich Getting Richer 💸
In a world where celebrities get paid absurd amounts just to show up at an event and sip a cocktail, you’d think they wouldn’t need to test their luck at a casino. And yet, some of Hollywood’s finest can’t resist the thrill of the game—and, let’s be honest, the flex of winning big.
Whether they’re hustling at the poker table or making the blackjack dealer sweat, these famous faces have proven that sometimes, the house doesn’t always win.
Dana White
It’s not every day a casino bans someone for winning too much, but when you’re Dana White, you don’t exactly play small. The UFC president, who already has more money than he knows what to do with, went on a blackjack rampage at The Palms in Las Vegas, raking in $2 million over three months in 2014. The casino was so rattled they cut his betting limit and eventually banned him from playing altogether.
Dana White gets a strange call from the Palms Casino telling him he is banned after winning $2,500,000 pic.twitter.com/wDqQAalrPZ
— Historic Vids (@historyinmemes) January 3, 2025
How did The Palms make amends? By sending him a championship belt that read “Palms Undisputed Blackjack Champion.” Classy.
Tobey Maguire
Before the internet started debating whether he’s the best Peter Parker, Tobey Maguire was busy cleaning up at underground poker games. The Molly’s Game saga exposed Hollywood’s most elite, high-stakes poker scene, and Maguire was reportedly one of its biggest winners, allegedly pocketing up to $36 million.
Tobey Maguire playing poker pic.twitter.com/GyBtGdKcH0
— Ade (@twilighttzone9) January 28, 2022
Sure, he had to settle a lawsuit for $80,000 after winning money from a Ponzi schemer (oops), but let’s be real—if you walk away from illegal poker games with millions and only one lawsuit, you’re doing something right.
Ben Affleck
Ben Affleck doesn’t just play poker well—he plays blackjack so well that casinos have had to kindly escort him away from their tables. Back in the early 2000s, Affleck made casino news headlines by winning a staggering $940,000 playing blackjack at the Hard Rock in Vegas, tipping dealers and staff with thousands like a true high roller.
rediscovered a photo of my mom playing poker at a table with ben affleck and matt damon pic.twitter.com/7P7gQgst7x
— angie (@hotsoggi) January 2, 2025
Celebrity rumors claim he’s been politely “asked” not to play at certain Vegas casinos due to his ahem impressive card-counting skills. But hey, if the man is good at math, let him live.
Drake
Just last month, Drizzy hit up a casino—specifically Crown Melbourne in Australia—and walked away with $700,000. Drake is known for betting big and winning big so it’s no surprise he’s casually cashing in six or seven figures here and there.
700k for lunch pic.twitter.com/hqcBXRPFcH
— Drake Direct (@DrakeDirect_) January 29, 2025
Paris Hilton
If you thought Paris Hilton’s talents were limited to DJing and saying “that’s hot,” think again. The hotel heiress reportedly won $50,000 at a Las Vegas casino one night after casually deciding to play blackjack. Unlike her peers, she didn’t even have a strategy—just sheer luck and vibes. She then spent her winnings on designer handbags because, well, what else would Paris Hilton do?
Throwback Thursday to Chris Moneymaker playing poker with Paris Hilton!!♦️♠️🤠👑 pic.twitter.com/A5lO2JeAgv
— WPT Global (@wpt_global) October 13, 2022
So, what have we learned today? That sometimes, even celebrities feel the rush of a good gamble, and every now and then, they walk away with more than just a comped suite and a free drink. Whether it’s a bet platform or an online casino, the thrill is just a click away. And hey, even if you don’t win $2 million like Dana White, at least you won’t get banned from playing.
(Probably…)
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