11 Most Tragic Gamblers in History

You’ve likely heard of Oriental Trading, which is one of the largest companies in the direct selling industry. Terrance Watanabe, a Japanese-American businessman, played a big role in Oriental Trading’s rise to prominence. In 1982, he took a controlling stake in the family business and build it into a wholesaling giant that sold over $300 million annually.

Watanabe sold Oriental Trading in 2000 for an undisclosed amount. Up until this point, he’d always concentrated on business over pleasure. But Watanabe changed his ways after earning a fortune from the sale of Oriental Trading. He began playing a variety of casino games, including slot machines, keno, and roulette.

Watanabe differed from many high rollers, who usually play games with low house edges like blackjack and baccarat. He instead enjoyed games with a large house edge, much to the delight of casinos. They showered him with comps as he gambled heavily in their casinos throughout the early and mid-2000s. Watanabe certainly didn’t beat the odds either as he lost a vast fortune.

The Nevada Gaming Commission fined Caesars $225,000 for allowing Watanabe to use illegal drugs on their property and also make “inappropriate sexual advances towards Caesars employees.” He and the casino settled out of court afterward for an undisclosed amount.

Akio Kashiwagi was a Tokyo property developer who hadan exorbitant amount of wealth. He claimed$1 billion in assets and also made $100 million annually. This fortune allowed him to become one of the biggest whales in Atlantic City and Vegas casinos.

“The Warrior” commonly wagered between $100,000 and $200,000 per hand while playing baccarat. He usually bet on credit and settled his debts with casinos afterward. Given Kashiwagi’s reputation, he was commonly granted huge credit lines worth $1 million or more. He was also given the chance to negotiate special deals with casinos, such as one he made with President Donald Trump and his Trump Taj Mahal casino in 1991.

Trump cut him off at $10 million in losses, which angered Kashiwagi. He left the casino with his remaining $2 million bankroll and failed to settle the debt afterward. The Warrior would never pay back his losses since he was murdered in his Japan home near Mount Fuji in January 1992. His body was found riddled with 150 wounds from a samurai sword.

Art Schlichter had a legendary college football career as quarterback of the Ohio State Buckeyes. He led the school to an undefeated regular season in 1979 and previously held the Buckeyes’ record for total offense. Unfortunately for Schlichter, he developed a serious gambling problem while he was in college. He bet heavily on horse races and sports, which caused him to lose several thousand dollars before he even graduated from Ohio State.

Things didn’t get any better after he was drafted fourth overall by the Indianapolis Colts in the 1982 NFL Draft. Expected to be Indianapolis’ quarterback of the future, he lost his starting job to the unheralded Mike Pagel early on in his career. Schlichter seemed more focused on gambling, which caused him to fritter away a $350,000 signing bonus before his rookie season was over. The NFL had a strike in 1982, which Schlichter used to use increase the amount of time he spent on gambling.

He would never play another down in the NFL again. But Schlichter continued making headlines for his gambling problems. He eventually started conning friends and families into giving him money, which he gambled away. In 2011, he pleaded guilty to theft and other charges and was sentenced to 10 years in prison.

Hollywood producer David Milch is famous for creating NYPD Blue (1993-2005) and Deadwood (2004-07). The former Yale English literature professor is lauded for his unique writing style and elaborate plots. Unfortunately, Milch has also become well known for having a serious gambling problem. A 2016 Hollywood Reporter feature details how he lost an alleged $100 million through gambling.

Milch’s downfall appears to be horseracing, because he became a regular at California’s Santa Anita (closed in 2013). One source told the Hollywood Reporter that Milch would wager “thousands and thousands of dollars” and“bet every race.” The legendary producer stopped paying his debts at one point and was sued. Court documents show that he lost $25 million from 2000 to 2011 alone.

He was also revealed to have had $17 million in tax debt, which forced him to agree to a payment plan with the IRS. Milch has since surrendered multiple mansions and other properties in an effort to pay off his debts. He’s also been put on a $40 allowance by his wife to prevent him from gambling. This is shocking when considering that he’s made tens of millions of dollars for his work on NYPD Blue, Deadwood, and Hill Street Blues.

Safa Abdulla Al Geabury is a Swiss businessman who lays claim to an Islamic art collection that’s been valued at over $1 billion. He used his vast amount of wealth to take out a large marker at London’s Ritz Club in 2014. Al Geabury proceeded to gamble away £2.2 million and refused to settle the debt afterward.

Al Geabury argued that he was a compulsive gambler who was taken advantage of by the Ritz. The London casino countered by arguing that Al Geabury signed an agreement stating his gambling problem was under control. Justice Simler eventually sided with the Ritz Club on grounds that Al Geabury provided inconsistent testimony. The judge also said that the defendant failed to provide compelling evidence that he had a gambling disorder at the time.

The art collector still refused to pay up, though, which led to another court appearance. Al Geabury refused to show up and claimed that he didn’t have enough money to make the trip to London. The judge finally had enough and sentenced him to 10 months in jail for contempt of court. The judge added it was obvious Al Geabury could afford to pay the £2.2 million debt, but simply refused to do so.

Gladys Knight is well known for her music career, which saw her win seven Grammy Awards from the 1960s to 1980s. The “Empress of Soul” earned a fortune that allowed her to play some of the highest stakes allowed in baccarat and blackjack. Knight never had much luck at the tables and lost $40,000 per night. In total, she estimates to have blown over $6 million through gambling.

What’s interesting about her case, though, is that she was never stressed about the losses. Instead, Knight had a gambling problem so bad that she sometimes forgot her obligations. Case in point, she forgot to take her son to school after staying out all night gambling and drinking. This motivated her to begin attending Gamblers Anonymous meetings and eventually giving up her habit. While Knight’s tale may have initially started out tragic, it’s good to hear that she’s now on the right path.

Leonard Tose made a $20 million fortune through a trucking company. He used this money to purchase the NFL’s Philadelphia Eagles for $16.1 million in 1969. This is a small amount compared to what NFL franchises are worth today. But back then – when the league wasn’t as high profile as it is today – the $16.1 million purchase price was a record.

Tose owned the Eagles from 1969 to 1985. He was only forced to sell his team for $65 million after accumulating heavy gambling losses. He racked up a $25 million debt at various casinos around the United States. Tose tried suing the same casinos for $500,000 each on account that they encouraged him to drink and continue gambling. Tose lost these court battles and was ordered to pay his debts. He eventually ended up broke and evicted from his mansion.

Real estate developer Harry Kakavas a earned a fortune worth over $1 billion by selling homes on Australia’s Gold Coast. Rather than using his wealth to make more money, Kakavas spent most of his fortune in casinos. The pathological gambler is estimated to have lost $1.5 billion in just over a year.


It’s easy to see why Kakavas lost so quickly when considering that he often made baccarat bets worth $300,000 per hand. After losing a massive amount in Australian casinos, he took his play to establishments in Las Vegas and Macau. Kakavas’ luck wasn’t much better at these casinos as he continued losing heavily. He once dropped $164 million during a single session in May 2006.

Perhaps Kakavas might have dug himself out of the hole had he continued focusing on his lucrative real estate career. But he instead spent the next several years trying to sue various casinos. Kakavas claimed that these gambling establishments provided him lavish comps in order to continue taking advantage of him. He predictably lost these lawsuits and failed to recover his money.

Pete Rose is arguably the best baseball player of all time. He still holds Major League Baseball record for the most hits (4256), games played (3,562), and singles (3,215). But rather than being celebrated for his athletic talents, Rose is much better known for his gambling scandal.

“Charlie Hustle” didn’t lose a massive portion of his fortune like most of the other people on this list. Instead, he committed a cardinal sports sin by gambling on baseball. Rose managed the Cincinnati Reds up until 1989, at which point the MLB opened an investigation into allegations that he gambled on the sport. Rose denied the claims for years. But the MLB found enough evidence to support allegations that he bet both for and against the Reds. It’s especially damning that he may have bet against Cincinnati. After all, he could’ve used his managerial position to influence results.

The league dropped potential criminal charges against Rose in exchange for him signing a permanent ban agreement.He eventually admitted in 2004 that he did bet on games as the Cincinnati manager. But he adamantly denies ever wagering against the Reds. Whenever the truth may be, Rose remains banned from baseball and unable to enter the Hall of Fame.

Jimmy White is one of the greatest snooker players of all time. He’s a six-time World Championship finalist and continues to play the game at age 56. Unfortunately, White lost a large amount of his snooker winnings by gambling on casino games and sports. He estimates have blown £2 million on gambling.

White told the Sun that he gambled to the point where he didn’t even care about wins and losses. Instead, he simply enjoyed the action. However, “The Whirlwind” finally became fed up with his gambling problem after splitting up with his wife, Maureen, and realizing how much time he wasted at sportsbooks.

Another catalyst for White’s change is that his friend and fellow snooker doubles partner, Alex Higgins, was also struggling with gambling addiction. White has since been able to kick his problem. He also stopped his partying ways, which he estimates cost him another £200,000.

A gambling tragedy can be viewed differently depending upon the perspective. Archie Karas would be considered a tragic story by many people. But Karas, who admittedly doesn’t care much for money, has never had a problem with his gambling addiction – even after blowing $40 million.

Karas’ story is quite amazing when considering that he started one of the greatest gambling runs of all time with just $50 in his pocket. He borrowed $10,000 from a poker buddy in 1992 and proceeded to run this amount up to millions of dollars through a combination of pool and poker.

Karas was on such a hot roll that pros began refusing to play him in poker and pool. By this time, he’d accumulated a $17 million fortune and could’ve easily retired from gambling. Instead, Karas switched to house-banked games in order to continue finding action. He got lucky in craps and ran his bankroll up to $40 million by 1995.

He continued betting high stakes on a combination of craps, baccarat, and poker. Karas’ losing streak continued as his bankroll eventually reached zero by 1996. Amazingly, he’s had several multi-million dollar runs since then. But Karas has always lost the money at some point or another. In 2013, he was arrested for marking cards at San Diego’s Barona casino. This got him blacklisted from Nevada casinos, where he’d been caught cheating multiple times before.