Terrance Watanabe said he bet more than $825 million and lost nearly $127 million of it in Caesars Palace and the Rio casinos in 2007, believed to be the biggest losing streak in Vegas history. Woman lost out on thousands of dollars after big casino mistake. Cynthia Obie from Maryland said she lost out on thousands of dollars after the casino staff took down her Social Security number wrong.

High rollers are typically wealthy people who can afford to gamble far more than the average person. The upside to betting so much is that these gamblers sometimes experience massive wins.

The downside, though, is that high rollers can also take heavy losses. Some casino players have actually become legendary for losing so much. I’m going to discuss 11 wealthy people who lost big to the house. These losers come from all walks of fame and fortune, including businessmen, professional athletes, and actors.

Akio Kashiwagi is a late Tokyo real estate investor who became famous for his extravagant gambling sessions at Atlantic City and Las Vegas casinos. He operated the Kashiwagi Shoji Company, which dealt in both Tokyo real estate and other investments. “The Warrior,” as he was known in gambling circles, claimed to earn $100 million per year and have $1 billion in assets. The exact nature of Kashiwagi’s wealth is unknown. He simply listed his profession as “business” when dealing with casino officials.
Kashiwagi regularly played baccarat for between $100,000 and $200,000 per hand. He often bet on credit and negotiated repayment deals with casinos after losing sessions. Kashiwagi was such a big gambler that casinos would commonly grant him $1 million lines of credit or more. He developed a reputation as one of the gambling world’s biggest whales in the early 1990s. One of the most famous stories involving Kashiwagi saw him make a special deal with Donald trump at the Trump Taj Mahal casino. Kashiwagi was going to play baccarat until he either won or lost $12 million.

Dennis Gomes, former president of the Trump Taj Mahal, told the New York Times that Kashiwagi was a “top 10” gambler. He added that the businessman would “sit at the baccarat table and bet $100,000 a hand for 80 hours.” Kashiwagi’s high-roller days came to an end when he was murdered in Japan near his to Mount Fuji home. His body was riddled with an estimated 150 wounds from a samurai sword. The murder has never been solved to this day, and he died while owing the Taj Mahal $4 million, and the Las Vegas Hilton $5 million in gambling debts.

Terrance Watanabe is a Japanese-American businessman who inherited a fortune from a family business. His grandfather moved to the US in 1932 and started the Oriental Trading Co. By 1982, Terrance tooka controlling stake in the business and guided Oriental Trading to new heights. The company was pulling in $300 million in annual revenue at the peak of his career.
By 2000, Watanabe sold the business for an undisclosed fortune. Up until this point, he had largely brushed off fun and entertainment like gambling. But he quickly made up for lost time by diving into the casino gaming world. Watanabe played a variety of casino games, including baccarat, blackjack, keno, roulette, and slots.

Casinos referred to him as a “house player,” because he chose games that carried large house edges. This is rare among most high rollers, who commonly choose skill-based games that give them a better shot to win. Playing these games certainly didn’t help Watanabe’s bankroll as he lost most of his fortune through gambling. He dropped $120 million in 2007 alone.

These accusations led Nevada gaming regulators to fine Caesars $225,000 for not responding “appropriately to allegations that Mr. Watanabe was using illegal drugs on company property and was making inappropriate sexual advances toward Caesars employees.” The two sides eventually settled out of court for an undisclosed amount. Watanabe has since kept out of the public eye and presumably no longer plays for high stakes.

Harry Kakavas created his wealth by selling houses on Australia’s Gold Coast. He accumulated enough money during his real estate career to gamble as much as $300,000 per round. Kakavas’ dedicated most of his action to Melbourne’s Crown Casino, where he lost $30 million. These gambling losses depleted his wealth and left him owing millions of dollars to banks, friends, and lawyers.
James Packer (son of Kerry Packer), who was Crown’s CEO, would lure Kakavas to his casino by offering lavish comps. Packer even sent a private jet to ferry and Kakavas to and from his Gold Coast home. The Crown also supplied him with $50,000 in “lucky money,” which was a small gift in comparison to the millions of dollars that they stood to win.

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And win the Crown did as Kakavas lost at an alarmingly high rate. One session saw him lose $2.3 million in just 28 minutes. Kakavas claimed that the Crown was taking advantage of his compulsive gambling and took them to court in 2010. His lawsuit centered on Crown’s obvious attempts to keep him gambling. The Victorian Supreme Court ruled that it’s not the law’s place to protect gamblers from themselves. According to the Monthly, the decision was somewhat surprising as Kakavas’ legal team presented a very good case.

4 – Kerry Packer

Kerry Packer is a late Australian Media tycoon who owned a majority interest in the Nine Television Network and publishing company Australian Consolidated Press. Both would later merge to create Publishing and Broadcasting Limited (PBL). Packer used his business acumen and family fortune to build a net worth of A$6.5 billion by the time of his 2005 death. His vast wealth allowed him to play for stakes that other gamblers could only dream of.
He once lost £13.6 million during a three-day baccarat stint at Vegas’ Bellagio. As reported by the Telegraph, this brought his gambling losses to £27.4 million for 2000 alone. A source told the paper that Packer “was soon down between £11.6 million and £13.6 million and then coming out of the weekend he didn’t recover.”

Packer’s affinity for gambling high stakes created many legendary stories. He’s said to have loaned the actor George Hamilton £125,000 so that he could afford to split aces. In another tale, a Texas oil rig owner was bragging about his $100 million net worth. Packer said “I’ll toss you for it,” which shut the oilman up.

Charles Barkley is one of the most-successful basketball players of all time, having been an 11-time NBA All-Star, 5-time All-NBA First Teamer, and NBA MVP (1993). But as good as Barkley was on the basketball court, he’s been equally as bad with gambling. Speaking with ESPN’s Trey Wingo in 2007, Barkley admitted that he lost $10 million through gambling. He also fessed up to losing $2.5 million in a six-hour blackjack session.
A year later, he refused to acknowledge that he had a gambling problem when speaking with TNT co-host Ernie Johnson. “It’s not a problem. If you’re a drug addict or an alcoholic, those are problems,” he said in 2008. “I gamble for too much money. As long as I can continue to do it I don’t think it’s a problem.”

The Wynn Las Vegas filed a civil complaint against Barkley shortly after this exchange. The Vegas casino claimed that the “Round Mound of Rebounds” failed to pay up on a $400,000 marker. Barkley admitted that he made a mistake in not honoring the debt and quickly repaid the Wynn. He also took a different tone when speaking on TNT’s pregame show. “I’ve got to stop gambling…I am not going to gamble anymore,” he said. “For right now, the next year or two, I’m not going to gamble… Just because I can afford to lose money doesn’t mean I should do it.”

6 – Charlie Sheen

Charlie Sheen has had a topsy turvy acting career. In 2011, the former Two and a Half Men star was dismissed from the show, and Warner Brothers studio altogether, following a number of strange incidents. He demanded a 50% raise for each episode of Two and a Half Men while simultaneously launching an anti-semantic rate. He also had other well-publicized problems, such as alcoholism, drug addiction, and the hiring of prostitutes.
Sheen’s sports gambling problem may be the least of the drama surrounding his life. But it was still an issue nonetheless in the mid-2000s. His sports betting came to light during 2006 divorce proceedings. Ex-wife Denise Richards cited Sheen’s gambling addiction as one of the primary reasons for seeking divorce.

In a 2012 interview, Sheen claimed to have kicked his betting habit. “I don’t bet anymore. I’m a retired gambler,” he explained. “Not a recovering gambler. Big difference. “I’ll still look at the lines. I’ll be like, yeah, that’s a blowout, that’s a 40-point blowout. Easy, right? I’ll watch the game. “It’s 40-point blowout the other way, and I can just walk away. I don’t have some dude calling, like, ‘Hey, yeah, so tomorrow, huh?”

Zhenli Ye Gon is a Chinese-Mexican businessman who was busted for selling chemicals used to make methamphetamine. Police raided his Mexico City mansion and found $205 million worth of cash. It’s no wonder how Ye Gon was able to become one of the biggest high rollers ever when considering how money he had lying around.
Ye Gon was born in Shanghai and maintained residences in China, Mexico, and Las Vegas. The latter afforded him the ability to gamble whenever he was in town. The US Drug Enforcement Administration uncovered that Ye Gon lost $120 million while playing at various Vegas casinos.

He bet up to $150,000 per hand in baccarat. The black-market trader was such a big whale that the Venetian Resort Hotel & Casino gave him a Rolls-Royce as a consolation prize. Of course, giving away the $300,000 Rolls-Royce was worth it when considering that Ye Gon likely lost tens of millions at the Venetian.

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8 – Michael Jordan

Michael Jordan is widely regarded as the best basketball player of all time. He won six NBA championships, earned six NBA Finals MVPs, and is a 5-time NBA MVP. During his famed career, Jordan created plenty of gambling related headlines. In 1993, he was seen in Atlantic City casinos the night before a playoff game against the New York Knicks.
Jordan still made it back in time to help his Chicago Bulls beat New York the following day. But he was a loser on the tables, dropping $165,000 in Atlantic City. Of course, this was nothing compared to the $1.25 million that Richard Esquinas claimed MJ owed him. The San Diego businessman said that he’d won the money off Jordan in a golf game.

“His Airness” was such an avid bettor that it’s even rumored his first retirement in 1993 was due to a secret gambling suspension. Whatever the case may be, Jordan’s penchant for gambling hasn’t disappeared. He can still be found on North Carolina golf courses making large bets with other players. MJ can easily afford his big gambles, though, when considering that he has over a $1 billion fortune and is the primary owner of the Charlotte Hornets.

Karas is the only person on this list who became rich through gambling. In fact, Karas is a true rags-to-riches story. He grew up in poverty on a small Greek island. Karas left home as a teenager and eventually ended up working on a cruise ship. Once the ship landed in America, he quit his job and embarked on a gambling career in the LA area. Karas experienced many highs and lows, winning as much as $2 million.
But he later lost all but $50 in the LA poker scene. Rather than taking time to gather himself, Karasdrove to Las Vegas in hopes of starting another run. He borrowed $10,000 from a fellow poker player and eventually turned this small loan into $17 million dollars through a combination of pool and poker.

His losing streak continued as he couldn’t buy a win in craps, poker, or baccarat. The end result was blowing his entire $40 million fortune by 1996, which amounts to $65 million when adjusted for inflation. What’s impressive about Karas is that he’s never stopped gambling. In fact, he’s gone on other big runs that’ve seen him win millions of dollars. Karas always seems to lose all this money, though, and never banks any profits. Of course, this makes sense when considering that he’s gone on record as saying that he doesn’t care about money.

Gladys Knight is known as the “Empress of Soul” for her beautiful voice and outstanding music career. She’s experienced success both with Gladys Knight & the Pips as well as a solo artist. Knight has also won seven Grammy Awards that were spread out from the 1960s to 1980s. But one thing that the Midnight Train to Georgia singer hasn’t won at, though, is gambling.
Her gaming habits became news when it was revealed that she lost up to $40,000 per night in baccarat and blackjack. Knight estimates that she’s lost around $6 million total. She was introduced to blackjack by a friend and continued playing table games for over a decade. Knight was so wealthy that she didn’t care about all of the money she was losing.

Instead, Knight realized her gambling problem after forgetting to take her son to school. She’d been drinking and gambling so long that she completely neglected her son that morning. Luckily, Knight began attending Gamblers Anonymous meetings and eventually kicked her habit.

11 – Safa Abdulla Al Geabury

Safa Abdulla Al Geabury is a Swiss businessman who allegedly owns an art collection worth over $1 billion. This fortune became the center of a dispute between Al Geabury and London’s Ritz Club casino. The story began when he took out a £2 million marker to gamble with in 2014. He lost the entire amount during a high stakes roulette session and never settled the debt.
Aside from refusing to pay up, Al Geabury also claimed that the Ritz Club tried taking advantage of him. He signed a self-exclusion from the casino in 2009, only to rescind this after claiming that his problem was under control. Justice Simler didn’t buy any of Al Geabury’s arguments and said that his testimony “was riddled with inconsistency.” The judge added that Al Geabury never established “any gambling disorder at any material time [in 2014].” Justice Simler also pointed out that Al Geabury had a $1 billion net worth and could’ve easily paid the £2 million debt.

Al Geabury refused to show up to a later court appearance and was then ordered to spend 10 months in jail. The judge found him in contempt of court for “doing nothing to comply.” Al Geabury argued that his wealth was exaggerated and he couldn’t afford to pay the marker. He even claimed that he couldn’t afford to fly from Switzerland to London for court. All of these arguments fell on deaf ears, though, as he was still held responsible for the debt and forced to spend months in jail.

Casino gaming is supposed to be about thrills and entertainment. But it can quickly turn bad when one gambles too much and spirals out of control. This especially becomes a problem when one has a seemingly endless cash flow. Terrance Watanabe, Harry Kakavas, Archie Karas, and Safa Abdulla Al Geabury actually gambled themselves into financial ruin.

Other magnates like Kerry Packer, Charles Barkley, Charlie Sheen, Michael Jordan, and Gladys Knight were rich enough to where their losses weren’t too impactful. But the sheer amount of money that they lost caused their stories to go public.

Akio Kashiwagi’s story is entirely unique and tragic. The Tokyo real estate mogul wagered as much as $200,000 per hand and racked up millions of dollars losses.

Kashiwagi refused to pay his debts and was found murdered by samurai sword just months later in early 1992. He was rumored to have ties to the yakuza, which could’ve played a role in his mysterious death.

Archie Karas is another interesting story, because he actually used skill-based gambling to become wealthy. However, Karas never called it quits and proceeded to lose his entire $40 million fortune.

In summary, some gamblers’ big losses are manageable, because they’re so wealthy. But high rollers go far beyond what they’re capable of losing and proceed to blow their entire fortune.