Two years ago, Cardassar lost everything. Now they're chasing Copa del Rey glory vs. Atletico Madrid. 20h Alex Kirkland. Playoff success in baseball is a bit of a roulette wheel. As the famous saying goes, “ The brightest flame burns the quickest “. There are plenty of successful entrepreneurs who quickly rise to financial success, only to lose everything just as abruptly. Life in the fast lane is not without its speed bumps, and here are some of the people who went from rags to riches – and then vice-versa.

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Gambling legends are typically very successful bettors who’ve made millions in profits over their careers. These gamblers have incredible skills that allow them to beat the house and other players.

Given how great these gamblers are, you’d think that they would also be good at bankroll management. But this isn’t always the case because certain legends are so bad at managing their bankrolls that they’ve lost entire fortunes.

Some of these gamblers lost their money in the actual games they play. Others have blown their wealth through other means like lousy business deals or drugs.

You want to avoid repeating the mistakes of the following nine legends if you ever become a highly successful gambler.

1 – Stu Ungar

The late Stu Ungar was arguably the best Texas hold’em player of all time. He proved his skills by winning three World Series of Poker (WSOP) Main Event titles.

As if his hold’em prowess wasn’t enough, Ungar also excelled at gin rummy and blackjack. His rummy skills were so excellent that no high stakes player would compete against him.

He especially had trouble finding action after beating rummy star Harry “Yonkie’ Stein 86-0. Stein, who was widely regarded as the best gin player at the time, disappeared from the scene after this beating.

Ungar took up Texas hold’em when his gin opponents dried up. He quickly experienced poker success after winning $40k off 7-time WSOP champ Billy Baxter in 1977.

“The Kid” would earn his first WSOP Main Event victory after beating Doyle Brunson heads up in 1980.
Ungar went on to win this tournament the following year in 1981 as well.

Unfortunately, Ungar developed a bad addiction to cocaine in the mid-1980s. He was introduced to the drug by fellow poker players, who said that it would keep him awake during long nights at the table.

The Kid was broke for years before resurfacing prior to the 1997 WSOP Main Event. He stayed up all night raising the $10,000 buy-in and went on to win his third ME title.

Dubbed “The Comeback Kid” afterward, he collected a $1 million payout for the victory. Ungar split the money with his backer, Billy Baxter, but still walked away with $500,000.

Rather than using the funds to further his gambling career, Ungar instead blew most of it on cocaine and sports betting. It’s estimated that he lost around $30 million in poker and rummy winnings due to his poor money management.

He would pass away the following year at age 45 in a Vegas roach motel. The Kid suffered heart failure resulting from years of drug abuse.

2 – Archie Karas

Archie Karas started gambling as a child while growing up on a small Greek island. He shot marbles with friends to earn money for food.

Karas got into an explosive argument with his father at age 15 and left home afterward. He hopped on a cruise ship, where he continued working until the ship reached America’s west coast.

Karas started playing poker in L.A. cardrooms and hustling local pool halls. He was able to build a $2 million bankroll, which he later lost playing against poker legends like Doyle Brunson and Chip Reese.

Some gamblers would be distraught after losing such a large amount of money. But Karas was undeterred and left for Las Vegas in 1992 with just $50 to his name.

Upon arriving in Vegas, he convinced a poker friend to lend him $10,000. He turned this into $30,000 through Razz, paid his friend back, and used the remaining $20k to start the most-legendary gambling run ever.

He proceeded to accumulate a $17 million bankroll through a combination of pool and poker. Karas ran into a problem, though, because nobody would play him in pool or poker any longer.

This convinced him to start playing high-stakes craps. The run continued too as he built his bankroll to $40 million.
Unfortunately, Karas couldn’t stop gambling.

His demise began when he played high stakes baccarat, which cost him $11 million. Karas would lose the rest of his money through a combination of baccarat, craps, and poker.

What’s impressive is that he’s since gone on several other multimillion-dollar gambling runs, only to lose everything in each instance.

In more recent years, Karas has made headlines for been caught cheating in blackjack. The last instance, where he was arrested for marking cards at San Diego’s Barona Casino, landed him in the Nevada Black Book.

The Black Book is an exclusive list of gamblers who are banned from Nevada casinos. The Silver State banned Karas because he’d been caught cheating in Vegas several times before the San Diego incident.

3 – Harry Findlay

Harry Findlay is a famous sports and horseracing and bettor who has won and lost millions of dollars through gambling.

Although a very successful gambler at times, the Brit has had major bankroll management issues throughout his career.

He infamously wagered £2.5 million on New Zealand winning a 2007 Rugby World Cup quarterfinal match against France. He felt pretty good about this wager with New Zealand dominating 13-3 at halftime.

However, the French came roaring back in the second half and narrowed the score to 18-13. This convinced him to put down a smaller £18,000 live wager on France that would pay £600,000 due to the long odds.

The French completed their miraculous comeback by winning 20-18. This brought his total losses to £1.9 million, which, although not as bad as £2.5 million, was still a huge disappointment.

Despite this catastrophic loss, Findlay continued betting huge chunks of his bankroll on what appeared to be sure things. He again backed New Zealand in the 2011 Ruby World Cup over France.

This time, Findlay put down £230,000 (over half of his wealth) on the Kiwis to win. New Zealand barely pulled out an 8-7 victory. It’s rumored that Findlay has won and lost £20 million on sports and racing gambling in his life.

He believes that the £20 million in winnings may be accurate, but not the matching losses.

“The money I have lost was all down to getting involved with businessmen who sold me visions that turned out to be bulls***,” he told the Independent.

“The reality is that throughout my life of gambling, I’ve only ever had one losing year since 1989 and that was 1997.”

Findlay went on to add that “three losing months” in a row is a disaster for him. He’s thankful that his single losing year has never been repeated.

One of the financial disasters he speaks of is when he put £1.7 million towards making Coventry Stadium the center for greyhound racing.

But he never received a Bookmakers Afternoon Greyhound Service (BAGS) contract. This made it nearly impossible for him to create a successful long-term racing operation at Coventry.

He fell into a depression afterward in 2014 and was broke.

“I didn’t have the train fare to see my mum and had a bit of a breakdown,” he recalled.

Since that time, though, Findlay has made somewhat of a comeback. He’s been having success by betting small stakes on horses with his best friend.

“Glenn [Gill] is the best horse judge I’ve ever me,” said Findlay.

“He tells me what to bet and how much. To have won over £250,000 the last two years betting on small stakes is amazing.”

4 – Erick Lindgren

Erick Lindgren is a professional poker player who had a considerable amount of success in the 2000s. He lays claim to two WSOP victories, two World Poker Tour (WPT) titles, and over $10.5 million in career winnings.

“E-Dog” became a popular player on the tournament circuit thanks to his easygoing attitude. He befriended many famous poker pros and earned a lucrative sponsorship deal with Full Tilt Poker.

Lindgren is also known for winning a $350,000 prop bet with Phil Ivey, Gavin Smith, and other poker pros. The bet saw him play four consecutive golf rounds at a Vegas course.

He had to carry his own bags and shoot under 100 in every round to win the bet. Despite temperatures reaching 106 degrees, Lindgren fought off heat exhaustion and won.

Sadly, though, Lindgren had a terrible gambling problem hiding behind his poker success and sponsorship deal.
He amassed huge losses in sports betting and eventually couldn’t repay his debts.

He also borrowed money from Full Tilt that he couldn’t pay back. Amaya Gaming, which purchased Full Tilt and PokerStars in 2014, sued Lindgren to recover millions of dollars in loans.

E-Dog couldn’t afford to repay the money or his back taxes ($1.8m), so he filed chapter 11 bankruptcy. He reported assets worth less than $50,000 and debts exceeding $10 million.

In 2013, Lindgren entered a gambling rehab program in California. He’s since failed to recapture the same glory he had during his earlier poker days.

5 – Phil Laak

Phil Laak is a successful poker pro who’s won millions of dollars in cash games and has made many TV appearances.

His first major win was the WPT Celebrity Invitational in 2004. He’s won several other tournaments, including a 2010 WSOP Europe six-handed NL hold’em event. Laak has $3.7 million in overall tournament winnings.

While the 46-year-old has had plenty of success on the felt, he’s better known for his many televised appearances. Laak has appeared on High Stakes Poker, Poker After Dark, E! Hollywood Hold’em, and I Bet You.

But long before his fame and fortune, Laak went broke after making an extremely risky option trade. He wrote about the matter in a 2009 piece that appeared on ESPN.com (via BLUFF Magazine).

“I went broke one time and one time only,” he wrote. “I leveraged myself to the hilt for an option trade on the NYSE, and things went about as badly as they could have gone.”

Despite losing everything he put into this trade, Laak learned valuable lessons on bankroll management. He now finds it puzzling how fellow poker pros can continue going bust again and again.

“It mystifies me when I hear successful poker players tell how they went broke so many times,” he wrote. “[…] However, not knowing about bankroll management is not why they go broke; they go broke because they don’t have the discipline to follow it.”

Laak himself learned plenty of discipline in the aftermath of the options trade gone wrong. He’s since built an impressive bankroll that has allowed him to play in many televised high stakes cash games.

6 – Chau Giang

Chau Giang fled his native Vietnam in a small boat in the late 1970s. His first stop was Denver, Colorado, where he worked minimum wage jobs while learning poker on the side.

He eventually had enough success in small games that he could afford to move to Las Vegas. He won the 1993 WSOP $1,50 NL Ace to Five Draw tournament ($82,800) and has since earned two more gold bracelets.

Giang has over $3.5 million in live tournament cashes. But cash games are his bread and butter because he’s won tens of millions of dollars in this arena. Giang became a regular in the $4,000/$8,000 “Big Game” at Bobby’s Room (Bellagio).

He also landed a Full Tilt Poker sponsorship in January 2009 under the handle “La Key U.” This deal added even more to Giang’s net worth.

However, he eventually lost everything by playing baccarat and craps.

In the autobiography Deal Me In, Giang wrote about how Vegas’ gambling temptations were his downfall.

“Unfortunately, winning $20 million in Las Vegas and keeping $20 million in Las Vegas are two different things,” he explained.

“I was good at the large cash card games, no doubt. But those games didn’t happen every day, or even every week. Lower-stakes games now bored me.”

“They didn’t hold my attention or generate the thrill of the high-stakes game. So I sought new avenues for excitement, and unfortunately those avenues were in the casino games, where the house is heavily favored to win.”

Giang lost everything through baccarat and craps. However, he has since rebuilt his bankroll to the point where he can play up to $200/$400 live cash games again.

7 – Ryazan

“Ryazan” was one of the first true stars of the daily fantasy sports (DFS) world. He became famous in 2015 for challenging other famed pros like Martin “Papagates” Crowley and Saahil Sud to heads-up matches.

Ryazan was also highly active on RotoGrinders and other DFS forums, where he issued challenges and bragged about his big wins.

What wasn’t known at the time, though, was that Ryazan funded his bankroll with credit cards. Despite winning quite a bit, he also racked up tremendous credit card debt and didn’t pay it off immediately.

Ryazan also blew his winnings without making any estimated tax payments beforehand. This left him owing debts to both the IRS and credit card companies.

The anonymous DFS star eventually became a losing player too, which further crushed his bottom line. A 2017 RotoGrinders post from Ryazan shows how he devolved into a losing degen.

Here’s an excerpt from the post:

“I lost playing NBA for the first 3 months of 2016 (80% of my 2015 overall winnings, + what I owed for taxes for my 2015 winnings). Horrible management on my part, I know, that is not even up for discussion – I was completely horrible in that personal aspect.”

“But it didn’t stop there – when I couldn’t win on a 5K monthly deposit limit, Fanduel permitted me to wire up to $30,000 straight from my bank account, seemingly completely ignoring the Massachusetts regulation of 1K per month.”

Ryazan’s last cash is a fourth-place finish in a DraftKings MLB contest on May 2, 2017. It looks like his credit card spending, back taxes, and losses have put him out of commission.

8 – Gus Hansen

Gus Hansen has served as one of poker’s most-iconic faces for well over a decade.

The “Great Dane” got his gambling start by playing backgammon in Denmark. He later switched to poker and considered himself a professional by 1997.

Hansen became famous in the mid-2000s after becoming the first player to win three WPT titles. He’s also won the WPT Bad Boys of Poker invitational, $400k Poker Superstars Invitational, 2007 Aussie Millions Main Event.

Hansen has over $10.2 million in overall live tournament winnings. Besides his tourney success, Hansen has become notable for his TV cash-game appearances and Full Tilt sponsorship.

He was prominently featured in many Full Tilt ads. Hansen was also one of just three players who were signed to “The Professionals” team when the site relaunched in 2012.

He’s had some successful business pursuits as well, launching PokerChamps.com with two other pros in 2003. They sold the site and its software to Betfair in 2005 for $15 million.

Unfortunately, Hansen’s biggest life leak involved playing high stakes online poker. He just couldn’t solve the internet nosebleeds despite his success in other poker realms.

Hansen’s losses began accruing in 2007. He bottomed out in 2015 with $20.7 million in overall losses and has since stopped playing online.

To Hansen’s credit, he never tried hiding or lying about his loss. He once admitted: “My online numbers aren’t looking too pretty, but I can still afford a sandwich.”

He again got himself into a financial pickle after investing in Denmark’s music industry. Hansen said this “went probably as bad as my online poker career.”

The good news, though, is that Hansen is back to crushing live cash games again. He made Instagram posts in December 2018 showing himself sitting with piles of chips in Bobby’s Room’s Big Game.

9 – Brad Booth

Brad Booth is a Canadian poker pro who became famous through appearances on High Stakes Poker. He’s well known for buying in for a “cool million” on the show.

Booth has one of poker’s more-unique backstories. Rather than moving to Vegas early on, he spent time grinding in cardrooms everywhere from Calgary to the Yukon Territory.

The latter is quite interesting when considering that the Yukon is a massive rural area with just over 40,000 inhabitants. “Yukon Brad” did eventually make his way south to Vegas, where he rose to stardom.

His downfall started, though, when he became a victim of the Ultimate Bet cheating scandal. He estimated that he was cheated out of $2 million while speaking with Mediocre Poker Radio.

Booth continued playing poker after the cheating scandal and lost another $4.2 million. He believes that the Ultimate Bet losses really messed with his confidence and momentum.

Yukon Brad would turn from victim to perpetrator when he failed to repay a $28,000 loan to Doug Polk in 2012.

Booth originally borrowed $30,000 and paid back $2,200. But he later left the country, changed his phone number, and began ignoring Polk.

Brad appeared in a 2017 interview with PokerListings, where he discussed the loan and how he’s grinding in low-stakes live games. He hopes to eventually rebuild his poker career and pay Polk back the full amount.

Conclusion

Having the skills to beat gambling is only one part of being a long-term success. It’s also extremely important to be disciplined with your bankroll as well.

The nine gamblers discussed here all went off the rails at some point and lost their bankroll.

Some of them have never recovered either.

Stu Ungar, unfortunately, died broke and penniless because he could never kick his drug habit. It’s a wonder how many poker titles he could’ve won had he avoided spending so much money on coke and sports betting.

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Daily fantasy’s “Ryazan” completely disappeared from the game after financing his bankroll with credit cards. He also waited to pay taxes on his winnings, then went through a big losing streak that busted his career.

Other gamblers like Brad Booth, Erik Lindgren, and Harry Findlay are still having success on a smaller level today. But none of them have yet to come close to the peaks they achieved before mismanaging their money.

Gus Hansen and Phil Laak appear to have learned their lessons after going broke. Each is doing fairly well in the poker world today.

The best takeaway from each of these gamblers is to be disciplined and make good decisions with your bankroll. Doing so allows you to experience long-term success in gambling rather than becoming a degenerate who loses everything.

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

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

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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.

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.

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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

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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.

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.