Let's be honest: we all dream of striking it rich and living that high-roller lifestyle. Hopping from casino to casino, staying in lavish suites, and betting obscene amounts of money on a single hand of blackjack or roll of dice. But the reality is, most of us are sitting here with a bank account more suited for the $5 blackjack tables (if we're lucky!). Still, a guy can dream, right? Here are the 17 biggest casino high rollers that will make you question every decision you've ever made.
Not the Miami Vice guy, this Don Johnson pulled off one of the biggest legal casino heists of all time. By negotiating absolutely ridiculous rules that flipped the house edge to his advantage, he managed to win $15 million from Atlantic City casinos in just a 4-month span in 2010.
Some of his negotiated rules included being able to double down on any hand, resplitting aces, getting rebates on losses over $500k, and even getting paid just to show up! With terms like that, it's no wonder he cleaned out the casinos.
Zhenli Ye Gon reportedly gambled $125 million in Las Vegas. This wealthy businessman had a bit of a side hustle - drug trafficking. Ye Gon is believed to have laundered hundreds of millions through Las Vegas casinos by purchasing chips, playing briefly, and cashing out with "clean" money. At one point, authorities seized over $200 million in cash from him in Mexico in what was one of the largest drug money busts ever.
Benter took an incredibly nerdy approach to beat the casinos - he actually created software models to predict horse racing winners with stats and mathematics. After getting banned from counting cards in Vegas at age 27, Benter pivoted and ultimately won over $1 billion from horse racing over 20 years. The guy turned handicapping into a billion-dollar algorithm. I can barely run the calculator app on my phone.
With an estimated net worth of between $20-30 billion at his peak, Hassanal Bolkiah is the hedonistic ruler of Brunei. Some of his rumored splurges include a $400 million personal jet, a $400 million palace, a $20,000 haircut (yeah, read that again), and owning over 5,000 cars. He would reportedly lose $1 million per day at casinos just for fun.
Simply one of the greatest and most iconic poker players ever, Phil Ivey has amassed over $30 million in live tournament winnings. But his high roller gambling doesn't stop at poker - he's been known to go on "crap tours," dropping 6-figures per craps roll and playing $200K/hand in baccarat. Ivey's idea of a fun gambling vacation is what I could only dream of after hitting a massive Powerball jackpot.
This Saudi Arabian arms dealer was at one point estimated to be worth around $4 billion. During the extravagant 1980s, he admittedly dropped $500,000 on prostitutes alone in a single year. Oh, and he also single-handedly caused a 19% dip in Hilton's quarterly profits one year from his casino losses. Khashoggi loved hitting up the high-stakes baccarat and blackjack tables in London. My biggest flex is utilizing that daily 2-for-1 happy hour deal.
The late Australian billionaire Kerry Packer might just take the cake as the most unbelievable gambler of all time. This absolute madman would play up to 7 hands of blackjack at once, with reported single-hand bets of up to $450,000. Let that sink in. He once won $33 million in a single Vegas session.
With just $50 in his pocket, Archie Karas embarked on one of the most legendary and unbelievable runs in gambling history. Playing primarily shootout-style craps, he turned that $50 into over $40 million in chips before inevitably losing it all.
The outspoken former NBA star has been extremely open about his gambling prowess...or lack thereof. By his own admission, Charles has lost around $30 million in his lifetime from gambling, mostly playing blackjack at places like the Wynn. Losing $30 million on blackjack seems like some kind of talent in itself.
Rounding out the list is this absolute madman Japanese baccarat player from the 70s and 80s. Kashiwagi reportedly wagered between $100,000 to $200,000 PER HAND while playing casino baccarat. His life took an obviously tragic turn when he was murdered in 1992, supposedly over gambling debts. I'll go ahead and put my alleged $20 slip losses into perspective now.
With the tremendous nickname "The Fat Man," this Syrian businessman definitely lived up to his reputation of going big. Al-Zayat is estimated to have lost over $42 million during a 12-year gambling bender, primarily in the high-end London casinos. He racked up so much debt that one casino sued him for millions after his checks bounced.
This ultra-wealthy Mexican textile mogul loves taking his hijinks to the Vegas Baccarat tables. Kamel Nacif has been known to wager upwards of $200,000 per hand, so why not when you're that loaded? He's also allegedly quite the hothead, throwing tantrums whenever his luck goes south.
The Hustler founder definitely fully embraces the "high roller" lifestyle. Flynt has been a staple in Vegas for decades, regularly playing $50,000/hand blackjack sessions. He's so good for business that new casino hosts will aggressively chase his action with lucrative comps. I once got a buy-one-get-one buffet voucher as a new player's signup bonus. Essentially, it's the same thing.
This legendary casino whale actually worked his way up from relatively modest means to become one of the biggest gamblers Vegas had ever seen. At his peak, he was dropping $5 million per night on underground high roller games before eventually being culled over $100 million in debt. The good news is his disastrous casino luck led to one of the first Las Vegas third-party gambling treatment programs.
This notorious high roller's rap sheet might be longer than his gambling losses. Ramon DeSage racked up $175 million in documented casino losses from the proceeds of a giant racketeering and money laundering scheme. He's currently serving over 10 years in prison, which gives me more jail time to reflect on where I went wrong in life compared to Ramon.
Here's a relative unknown but still extremely wealthy Chinese high roller who basically broke Australian casinos in the 2000s. Over the course of a legendary run, Mo Chan amassed over $10 million in winnings playing Baccarat with bets as high as $500,000 per hand. The casinos tried reining him in, so Chan simply vowed never to return to their properties again.
Rounding out this list of all-time whales is Sir James Goldsmith, an Anglo-French billionaire financier who could be considered one of the original Vegas high rollers. Back in the 60s and 70s, Goldsmith would make annual week-long trips to Sin City and gamble with million-dollar bankrolls. He was known to win (and lose) over $20-30 million per Vegas vacation before eventually getting banned from properties.
After reading about the 17 biggest casino high rollers, I need to take a nice long look in the mirror and reevaluate my life's priorities and decision-making skills. Or maybe I should just embrace the fact that I'll never experience that level of obscene wealth and ridiculous gambling losses.
Did reading about these whales' exploits make you want to take a second job to fund your gambling habit? Or just make you utterly demoralized about your life's accomplishments? Either way, it never hurts to dream...at least until the student loan bills arrive.
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