Many gamblers strive just to win meager profits. But a small percentage of players have actually managed to become rich through gambling.

Harry Kakavas, a real-estate salesman who made a fortune selling houses on Australia's Gold Coast, claims Melbourne's Crown Casino were aware he had a gambling problem but took advantage of his. During a year-long gambling streak, Terry lost a mind melting $204 million dollars at two Vegas casinos. Both gambling halls are owned by Harrah's Entertainment, Inc. And Watanabe's staggering. It's common for famous people to purchase everything from luxury cars to real estate, but certain celebs gamble away their earnings at casinos and poker tournaments. Some of Hollywood's biggest movie stars have reportedly been addicted to gambling, including Ben Affleck, Charlie Sheen, and Tobey Maguire.

The biggest winners often have the perfect mix of talent, fearlessness, and bankroll management. Unfortunately, some big winners are lacking in the latter category.

These same players have won and lost fortunes due to their inability to handle money and/or walk away. The following 7 gamblers serve as cautionary tales for knowing when to quit.

1 – Stu Ungar

Stu Ungar is best known for winning three WSOP Main Event titles. He took down this prestigious tournament in 1980, 1981, and 1997. The latter title earned him the nickname “The Comeback Kid.”

However, Ungar was proficient in more than just poker. He first became a professional gambler through gin rummy.

After standing out in the New York gin rummy scene, Ungar travelled to Las Vegas in search of action. He dominated the competition so badly that nobody would play him anymore.

Ungar was also extremely good at blackjack. He was so good, in fact, that he could count a six-deck shoe and know what the final card was.

Celebrities Who Lost It All Gambling Casinos

While Ungar was excellent at various forms of gambling, he did poorly with sports betting. He also developed a bad cocaine habit that would fester throughout the years.

The combination of sports betting and coke led to Ungar losing everything he made on the gambling tables. But he still experienced a shining moment after winning the 1997 WSOP Main Event.

Ungar split the $1 million prize with his backer, Billy Baxter. Sadly, he blew his $500,000 share on drugs and sports gambling.

Just a few months later, he died in a seedy motel of a heart attack. The heart attack was the result of years’ of cocaine usage.

2 – Erick Lindgren

Erick Lindgren was one of the biggest beneficiaries of the poker boom (2003-2006). He won multiple WSOP gold bracelets and World Poker Tour titles at the height of poker mania.

“E-Dog” also landed a sponsorship deal with Full Tilt Poker that paid him $300,000 per month. Lindgren used his wealth to bet on sports and fantasy sports.

The latter caused his sports gambling problem to surface in 2012. Fellow gamblers began complaining that Lindgren failed to cover a $100,000 buy-in into a private fantasy league.

Soon, others came forward with stories about the two-time WSOP champ owing them money. He eventually declared bankruptcy after realizing that he had no chance to cover some $12 million worth of debt.

He owed $3.8 million in back taxes to the IRS. Lindgren also owed fellow gamblers, including poker pro Andy Bloch, an estimated $6.1 million.

He’s since gone into gambling rehab multiple times and continues to play poker. But Lindgren will never be able to pay all the people whom he owes money. Of course, bankruptcy court probably took care of most of this debt for him.

3 – Terrance Watanabe

Unlike many other gamblers on this list, Terrance Watanabe has never been a professional. Instead, he’s a whale who formerly ran Oriental Trading Co.

Watanabe took over the family business in 1977 and helped it become a prominent brand. The Japanese-American businessman sold his stake in Oriental Trading in 2000 and retired a wealthy man.

He set out to be a great philanthropist in his retirement. However, he spent far more time in Vegas casinos.

Watanabe was the biggest fish in the casino and would play everything from keno to slot machines. He lost big playing these games and others.

Of course, Vegas was more than willing to offer him generous comps. Caesars, for example, created a special “Chairman” VIP level just for Watanabe.

The CEO would proceed to lose over $200 million through gambling alone. He eventually sued Caesars Entertainment in an effort to avoid paying up on a $14 million debt. The two sides settled out of court.

4 – Ryazan

“Ryazan” became one of the most-famous daily fantasy sports (DFS) pros in the mid-2000s. He won a fortune through football and other games in 2015.

Feeling good about his skills, Ryazan began challenging other noted pros like Martin “Papagates” Crowley and Saahil Sud to matches.

In fact, he used credit cards to fund his initial bankroll. Ryazan spent much of his 2015 fortune and used credit cards to reload his account.

The result was mounting credit card interest and a diminishing bankroll. His career took a downswing in 2016 that left him unable to cover the massive taxes on his 2015 earnings.

5 – Charles Wells

Charles Wells is similar to Terrance Watanabe in that he didn’t become famous for being a professional gambler. In fact, he was a conman long before his gambling ventures came to light in the 1890s.

The Englishman funded his initial gambling bankroll via a phony musical jump rope. He duped investors into giving him a collective £4,000.

Wells took the money and headed to Monte Carlo. Here, he played roulette using the Martingale system and got lucky enough to break the bank (win every chip at a table) multiple times. By the time the trip was over, Wells had earned 1 million francs.

He went back to Monte Carlo shortly after the first big win. He did even better this time, breaking the bank 17 times.

Wells became a celebrity upon returning to Britain. He even toyed with the press that he had a secret roulette strategy.

This notion was just another con. Wells simply got lucky while using an aggressive betting strategy.

The luck would finally run out when he returned to Monte Carlo for a third time. He lost everything and returned to Britain penniless.

As if this wasn’t bad enough, Wells was also arrested for fraud. He spent the rest of his life in and out of prison.

6 – Harry Findlay

A professional sports bettor, Harry Findlay has won millions of pounds through different sports and horse racing. He’s also become a celebrity in the UK due to his outspoken ways.

Findlay started drinking his own Kool-Aid in 2007. He placed a £2.5 million bet on New Zealand beating France in the Rugby World Cup.

Findlay was so sure of a win that he held a big party at the stadium. His huge bet looked like it would pay off when New Zealand led 13-3 at halftime.

Despite the big lead, Findlay hedged with a relatively small bet on France making a comeback. This wager promised to pay £600,000 if the French pulled off the miracle.

They indeed did so and dealt Findlay a massive lost. He at least salvaged £600k thanks to his halftime hedge.

This was just the beginning as Findlay continued to lose more bets over the years. He also poured money into saving Coventry Stadium’s greyhound racing program only to get burned.

Findlay is now worth far less than he used to be. He’s still a successful horse bettor but not to the same extend as previously.

7 – Archie Karas

No story beats Archie Karas’ fall from gambling grace. He managed to pull off the greatest gambling run in history only to lose everything.

Karas’ tale began in Los Angeles where he was down to his last $50. Rather than saving up money to reload, he headed to Las Vegas in 1992.

Once here, he borrowed $10,000 from a friend and won enough to build a decent bankroll. Karas proceeded to win millions of dollars through a combination of pool and poker.

By the time he was worth $17 million, nobody would play Karas in pool or poker. He resorted to playing high-stakes craps at Binion’s Gambling hall.

In 1995, Karas switched to baccarat and lost $11 million. He returned to the craps tables only to lose an additional $18 million.

Following a brief visit back to his native country of Greece, Karas began playing baccarat, craps, and poker in Vegas. All three propelled his losses until he was left with nothing.

Karas has since gone on other large runs only to lose the money. He was arrested in 2013 for marking cards at a San Diego casino.

Conclusion

All the gamblers on this list have had to think ‘what if’ when reflecting back on their careers. Each of these players was up big at some point and lost everything.

Ungar is arguably the best all-around gambler ever. But sports betting and cocaine proved to be powerful addictions that he couldn’t overcome.

Erick Lindgren once appeared set for life thanks to his poker winnings and Full Tilt sponsorship. But like Ungar, he couldn’t resist betting big on sports — much to his detriment.

Terrance Watanabe built Oriental Trading into a well-known international company. He cashed out in 2000 only to lose over $200 million of his fortune to Vegas casinos.

Ryazan was one of the earliest success stories in DFS. However, his good fortune took a downturn when mounting credit card debt and bad bankroll management caused him to go broke.

Charles Wells was a nineteenth century conman who got extremely lucky playing roulette. He pushed his luck too many times and lost everything.

Harry Findlay won millions of pounds through sports gambling. But big bets and a failed bid to help UK greyhound racing cost him his fortune.

Finally, Archie Karas won $40 million after starting with just $50. He couldn’t quit at the top, though, and ended up losing the entire amount.

Celebrities Who Lost It All Gambling Losses

You may never win as big as any of these gamblers. But if you do, heed their stories so that you can quit with some of your profits.

Celebrities Who Lost It All Gambling Winnings

Professional athletes can make millions of dollars through lucrative contracts — and sometimes billions when you add in endorsement deals — but despite their high paychecks, many end up going broke. According to a 2009 report by Sports Illustrated, 78% of former NFL players have gone bankrupt or are under financial stress within two years of retirement, and within five years of retirement, an estimated 60% of former NBA players are broke. Similar fates have befallen professional baseball, golf and hockey players as well.

Celebrities Who Lost It All Gambling Money

But where exactly do those millions go? GOBankingRates is breaking down exactly how 25 athletes lost millions of dollars, with some falling from the top of their game to financial rock bottom.

Last updated: July 28, 2020