Billionaire Gamblers Who Lost Their Fortunes

It’s easy to assume that if you’re a billionaire, you can handle any gambling loss. After all, what’s a few million dollars when you’ve got billions in the bank? However, as these high-rollers have shown, high-stakes wagers can take a serious toll—even when you’re used to the finer things in life. If you’re curious about other legends who have taken massive risks, check out this list of top billionaire gamblers who made headlines for their eye-popping wagers.

Below, we’ll dive into the stories of four famous (and sometimes notorious) billionaire gamblers and see how their love of risk led to colossal losses.

Terrance Watanabe – The Biggest Casino Loser in History

Terrance Watanabe inherited his fortune from the family business, Oriental Trading Company, which he eventually sold. With that windfall, he headed straight for Las Vegas, where he became one of the city’s most recognizable high-stakes players. His game of choice? Baccarat, with occasional forays into slot machines.

In 2007, Watanabe famously lost $205 million across two casinos—Caesars Palace and The Rio—a sum so staggering it’s often cited as the largest losing streak by a single gambler in Vegas history. Later, he sued the casinos, claiming they encouraged him to gamble while intoxicated. Whether or not that’s true, his legendary loss is a prime example of how even the wealthiest people can be overwhelmed by an unchecked gambling habit. While some high-rollers rely on gambling strategies to curb losses, Watanabe’s downfall shows what happens when limits get pushed too far.

Zhenli Ye Gon – The Drug Kingpin Who Gambled Hundreds of Millions

When authorities raided Zhenli Ye Gon’s mansion in Mexico, they discovered $205 million in cash, the largest drug-related money bust in history at the time. Ye Gon, a Chinese-Mexican businessman, allegedly built his fortune by smuggling chemicals used to manufacture methamphetamine. He then funneled hundreds of millions into Las Vegas casinos like The Venetian, where baccarat was his preferred game.

While Ye Gon’s story may not be your typical “self-made billionaire turned gambler,” it underscores how massive fortunes—no matter how they’re earned—can be lost in the blink of an eye. 

Akio Kashiwagi – The Japanese Tycoon Who Bet Big and Paid the Price

Japanese real estate magnate Akio Kashiwagi was known for sitting down at the baccarat table and casually betting $200,000 per hand. His intense style of play earned him VIP treatment at casinos in Atlantic City and Las Vegas, but it also attracted massive debts. One particularly famous case involved a reported $12 million debt owed to Donald Trump’s casino—an amount that supposedly went unpaid.

Tragically, Kashiwagi’s high-stakes lifestyle ended when he was found murdered in his Tokyo home in 1992, stabbed over 100 times in what many believe was a Yakuza-related killing. While there’s no conclusive evidence directly linking his gambling debts to the crime, his story remains a chilling example of what can go wrong when you’re dealing with enormous sums of money and even larger personal risks. 

Kerry Packer – The Billionaire Who Won and Lost Millions

Australian media mogul Kerry Packer owned companies like Channel Nine and Australian Consolidated Press, which helped make him one of the richest men in the world. True to form, he took his big-money mindset straight to the casino floor. Legend has it he once walked away from a single gambling session $33 million richer—only to lose $28 million on another night at the MGM Grand in Las Vegas.

Unlike some of the other billionaire gamblers we’ve discussed, Packer had enough financial cushion to absorb these staggering swings. He was also known for his over-the-top generosity, such as tipping dealers with million-dollar chips and covering strangers’ losses for fun. For him, gambling seemed more like a sport than a make-or-break obsession. Still, his epic wins and losses reveal just how risky high-stakes wagers can be, no matter how deep your pockets are.

For more fascinating insights into these kinds of lives, you can explore the inside lives of billionaire gamblers and discover how quickly fortunes—and fates—can change.

Final Thoughts

It’s clear that money alone doesn’t shield anyone from the highs and lows of gambling. Terrance Watanabe showed us the perils of an unchecked habit, Zhenli Ye Gon demonstrated that questionable money can vanish as quickly as it appears, and Akio Kashiwagi tragically illustrated the darker forces that can swirl around big-time gamblers. Then there’s Kerry Packer, who stands out for riding the roller coaster without ever truly jeopardizing his fortune.

Regardless of who you are, the biggest lesson is that high-stakes gambling comes with serious risks—financial, legal, and personal. So whether you’re betting $200,000 per hand or trying your luck at the slots, keep your wits about you. Even for billionaires, the line between thrilling success and catastrophic loss is razor-thin.