11 Gamblers Who Should’ve Quit While They Were Ahead

Few gamblers ever reach the point where they’re making millions of dollars, but those who do often become legends within their respective games.

These same gamblers can accumulate fortunes that will leave them set for life. And if they’re smart, they’ll eventually walk away from gaming and enjoy their money.

Not all pros ride off into the sunset and live happily ever after.

Unfortunately, some blow their fortunes through various means.

The following 11 gamblers were all highly successful at one time or another. However, they’ve pushed their luck and have either gone broke or suffered through other hardships.

1 – Tom Dwan

Tom Dwan has one of the best online poker origin stories ever. He received a $50 birthday gift from his father, which funded his initial online poker account.

From here, he went on to build a multimillion-dollar bankroll and become a big high-stakes online star.

He’d become such a star that, by 2009, he began issuing challenges to fellow high-stakes pros. “Durrrr” offered 3:1 odds ($1.5 million against $500k) that he could defeat anybody over the course of 50,000 hands.

He found two takers in Patrik Antonius and Dan “jungleman12” Cates. Dwan was actually getting the better of Antonius when their match fizzled. But Cates has won over $1 million off Dwan in their challenge, which they may never finish.

Durrrr took on rising poker phenom Viktor “Isildur1” Blom heads-up the same year. Blom proved too much for Dwan, winning $5 million in their series of heads-up games.

Despite the massive losses, Dwan regained his composure and ran his bankroll up to $8.2 million by April 2010. It took him just over three years to go from being a new high-stakes player in 2007 to crushing the game.

Unfortunately, durrrr would suffer a huge downswing by losing $3.5 million from April to June 2010. By the time Black Friday hit (April 15, 2011), he’d lost $6 million of his original $8.2 million in winnings.

The combination of his declining graph and Black Friday convinced Dwan to dedicate himself exclusively to the Macau live scene. Macau’s high-stakes games are a hush-hush affair.

Many rumors have surfaced that Dwan owes the Triads money, although it’s unclear if these are jokes or to be taken seriously. Regardless, Dwan is unlikely doing anywhere near as well financially he was in the late 2000s.

2 – Charles Wells

Charles Wells didn’t initially make his money from gambling but rather by conning people out of their savings. He fabricated invention ideas and got people to invest in his phony projects.

By the early 1890s, he conned people with a promise to invent a musical jump rope. Investors gave him £4,000, which he was supposed to use on the invention.

Wells instead took the funds and went on a gambling trip to Monte Carlo in 1891. What ensued was one of the luckiest gambling strikes of all time.

He began playing roulette and winning heavily. Wells broke the bank multiple times, meaning he won all of the available chips at several tables.

He left Monte Carlo a very rich man with what amounted to millions of dollars at the time. He’d return a second time and push his luck again.

This trip proved even more lucrative than the first, as Wells broke the bank a reported 17 times. Upon returning to England, he was an instant celebrity who was thought to have some secret trick to beating roulette.

During interviews, Wells went along with the idea that he had a secret roulette strategy.

What people didn’t know is that he simply used the Martingale system.

The Martingale system is where one doubles bets after each loss. Apparently not satisfied with his massive winnings, Wells conned investors with another invention idea. He put this money towards a giant yacht and sailed it back to Monte Carlo for a third gambling trip.

The Martingale system would finally fail Wells because he lost all of his money. He was immediately arrested after coming back to England a penniless man and spent years in prison.

3 – Erick Lindgren

Erick Lindgren was one of the most successful poker pros during the mid-2000s boom years. He won two WSOP gold bracelets and two World Poker Tour (WPT) titles during the height of his success.

Lindgren also earned a lucrative sponsorship deal from https://www.gamblingsites.org/history/full-tilt-poker/ Full Tilt Poker that paid him millions per month. This poker site even issued him big loans on top of the huge monthly salary.

But what Full Tilt and others didn’t realize is that Lindgren had a major sports betting problem. Although successful at poker, he was terrible at both sports gambling and daily fantasy sports.

Creditors blasted him on poker forums for not repaying his debts in the early 2010s. Full Tilt, which accidentally lent Lindgren an extra $2 million, sued him for refusing to give the money back.

Here’s a running tally of Lindgren’s known debts:

  • $2.5 million to Stars Group (owns Full Tilt now)
  • $3.8 million to the IRS
  • $5 million (estimated) to other players
  • $1.1 million to Andy Bloch (loan)

E-Dog is unlikely to pay the vast majority of these amounts back — if anything. He’s filed for bankruptcy twice in order to protect himself from creditors.

The good news is that he’s checked himself into gambling rehab multiple times to help with his problem, but Lindgren is very unlikely to ever reach the same perch he had during the poker boom.

4 – Archie Karas

Archie Karas lays claim to what’s quite possibly the best gambling story of all time. In 1992, Karas was broke after a bad poker run and had just $50 to his name.

Rather than getting a job and trying to rebuild his savings, the Greek-born gambler took his remaining $50 and drove to Las Vegas. Here, he convinced a poker friend to lend him $10,000.

Karas then began building a large bankroll through a combination of pool games and poker. He was eventually unable to find any more pool action do to his high skill level, which forced him to focus on poker.

Karas, who wasn’t considered one of the game’s elite players, was on such a hot run that he dominated notable pros like Doyle Brunson and Chip Reese. After running his bankroll up to $17 million, he could no longer find poker opponents either.

Archie turned his attention to the craps tables at Binion’s Gambling Hall. This situation was different, given that he was now playing a house-banked game where he couldn’t gain an edge.

Nevertheless, Karas’ luck continued as he built his bankroll to $40 million. He had so much money at this point that he hired his brother as a security guard when transporting cash around casinos.

Karas’ run would finally go cold by 1995 when he proceeded to lose $11 million in high-stakes baccarat. He then went back to the craps tables in an effort to recapture his magic, which cost him another $18 million.

At one point, Karas took a break and went back to his native country of Greece. He returned to Vegas with a renewed focus, although it wouldn’t help him regain his winning ways.

Archie proceeded to lose the remainder of his money playing baccarat, craps, and poker. Amazingly, Karas has said that losing this entire fortune didn’t bother him.

He’s a gambler at heart and wasn’t going to stop playing just because he was losing. Archie has since had a few more multimillion-dollar runs, but he’s always managed to lose everything at some point.

5 – Billy Walters

Unlike some gamblers on this list, Billy Walters never experienced a major downswing. In fact, he’s only suffered one losing year in over four decades of gambling.

Walter’s rise to success began when he joined a group of fellow pros called the “Computer Team.” They used computer technology in the early 1980s — a point when many people didn’t even know PCs existed — to make winning sports bets.

In 1986, the Computer Team also used their skills in roulette at Atlantic City’s Golden Nugget Casino. They employed their technology to record roulette results and look for biased wheels, or those that favor certain numbers due to wear and tear.

The team found a faulty wheel and wagered on the biased numbers again and again.

They were finally banned by the Golden Nugget, but not before winning $4 million.

Walters has since become one of the greatest sports bettors of all time. He’s won a number of notable bets, including a $3.5 million wager on the New Orleans Saints in Super Bowl XLIV and a $2.2 million bet on USC in 2007.

Unfortunately, earning millions of dollars in sports gambling wasn’t enough. Walters conspired with former Dean Foods CEO, Thomas C. Davis, in an insider-trading scandal.

He talked Phil Mickelson into trading Dean Foods stock because the professional golfer owed him $2 million. Mickelson was able to make $1 million and pay Walters part of the debt before the scandal broke.

The Securities and Exchange Commission (SEC) caught on to the scam and busted both Davis and Walters. The latter is now serving a five-year prison sentence after his 2017 conviction.

6 – Phil Ivey

Phil Ivey was once bulletproof in the poker world. He couldn’t seem to lose throughout the 2000s, capturing ten WSOP gold bracelets and a number of other tournament titles.

As if this wasn’t enough, he won over $20 million in online poker profits. Taking on internet legends like Dwan and Blom, he came out on top more often than not in many of these games.

But his golden story began taking a downturn in 2011 when Full Tilt ran into trouble following Black Friday. Ivey was receiving both sponsorship money and a return on his investment in the site — both of which ceased at this point.

He stopped playing in the WSOP and online so that he could focus on a lawsuit against Full Tilt. Ivey had lost his edge by the time he returned to the virtual felt in 2012. He proceeded to lose several million dollars and eventually stopped playing online.

He’s still a great poker player, as proven by his multiple high-roller tournament titles in recent years. But he seems more focused on business ventures and other forms of gambling these days.

Case in point, he won a combined $21 million from Crockfords Club (London) and the Borgata (Atlantic City) through punto banco. He was using a little-known advantage play technique called edge sorting, which involves looking at card edges to predict their values.

Much like blackjack card counting, edge sorting seems like a valid gambling method. However, Ivey made special requests that pushed the boundaries of legal advantage play.

Here’s a look at what he and his accomplice, “Kelly” Sun, asked of casinos:

  • Mandarin Chinese-speaking dealer (so Sun could secretly communicate with them)
  • Purple Gemaco deck (had flawed edges)
  • Cards rotated 180 degrees (easier to see flawed edges)

Crockfords withheld $12 million in winnings from Ivey, leading him to sue them. The Borgata, meanwhile, sued Ivey to recoup nearly $10 million that they paid him.

Judges in both cases sided with the casinos because they felt that Ivey used questionable tactics to win. At the time of this writing (mid-2019), Ivy is dragging his feet on repaying the Borgata.

7 – Harry Findlay

Harry Findlay is a professional bettor who has become a celebrity in the UK. His gregarious personality and large winnings have helped him become one of the most famous gamblers of all time.

Findlay experienced lots of success in his early betting days, winning millions of dollars. He used a portion of these earnings to wager £2.5 million on New Zealand winning a 2007 Rugby World Cup match against France.

New Zealand took a 13-3 lead at halftime, which made it seem like Findlay winning was a foregone conclusion. However, he decided to hedge his bet with one that would pay £600,000 when France made a late comeback.

The French won the match, meaning that Findlay “only” lost £1.9 million, but this loss was still a massive hit to his bankroll.

British tabloids have claimed that Findlay has won and lost £20 million through gambling.

He agrees with the winnings but disputes the £20m in losses.

Much like Walters, he claims to have rarely had a lengthy losing streak. But Findlay does admit to blowing millions when he tried saving the Coventry Stadium’s greyhound racing operation.

He’s since rebounded to a degree by winning some money through horse racing, but these profits are a far cry from the millions he used to win.

8 – Gus Hansen

Gus Hansen is another poker player who benefited greatly during the poker boom. He became the first player to win three WPT titles, doing so from 2003 to 2004.

Hansen also made out when he and two partners sold Poker Champs to Betfair for $15 million in 2005. He collected a $5 million profit from this deal.

The “Great Dane” furthered his fortune as one of the main faces of Full Tilt Poker. He often appeared in their ads as a suave gambler.

Unfortunately, most people no longer remember Hansen for his Full Tilt ads or tournament titles. He’s instead synonymous with being one of the biggest online poker losers of all time.

He started playing the online nosebleeds in 2007. What ensued was a consistent downward graph that bottomed out at $21 million when he stopped playing online in 2015.

The good news for Hansen is that he can still play the game and regularly gets staked at the “Big Game” in Bobby’s Room. The downside is that he could be a lot richer had he quit playing online earlier.

9 – “Ryazan”

“Ryazan” was one of the first major winners in daily fantasy sports (DFS) in the early going. He not only had a high rate but was also willing to challenge other famous pros like Saahil Sud and Martin “Papagates” Crowley to heads-up matches.

Ryazan was also notable for frequenting DFS forums like RotoGrinders, where he commonly talked up his winnings and skills.

He failed to mention is that credit cards were the primary source of his bankroll.

His winnings were somewhat counteracted by the credit card interest he owed.

As if this wasn’t bad enough, he also spent or lost most of his earnings from 2015. He was therefore left without enough money to cover his taxes that were due in 2016.

Ryazan’s downfall continued when he tried becoming a successful NBA bettor. He detailed his troubles through a 2017 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.”

Ryazan hasn’t cashed in a DFS contest since May 2, 2017, when he took fourth in a DraftKings event. He’s likely left the daily fantasy world for good.

10 – Brad Booth

Brad Booth was one of the most successful online and live high-stakes poker players during the boom years. He’s especially well known for his appearances on the GSN show High Stakes Poker.

Booth was a likable player who had an interesting backstory. He grinded in poker rooms throughout the Yukon Territory (pop. 40,000) during his early days with the game.

“Yukon Brad” would eventually move to Vegas, where his skills translated well over to the Big Game. Booth won millions of dollars by playing at Bobby’s Room and various online sites.

But one of these sites, UltimateBet, would be his undoing. Booth was cheated out of an estimated $2 million in the mid-2000s.

Russ Hamilton, one of UltimateBet’s investors, used a “god mode” program that let him see hole cards from Booth and other opponents. Yukon Brad spent years afterward seeking justice, which never came.

He lost another $4 million playing online poker. Booth cited the UltimateBet scandal as causing him to lose his confidence and second-guess his decisions.

Booth has unfortunately turned into a heel in recent years. He’s borrowed money from various pros — including $30,000 from Doug Polk — and has failed to repay his loans.

The Canadian poker pro still grinds in low-stakes games and wants to pay everyone back. But it’ll be tougher now that he doesn’t win nearly as much.

11 – Mike Matusow

Mike Matusow had a rough introduction to the gambling world. He started out playing video poker in Vegas casinos so much that he suffered repetitive strain in his arm.

Still a teenager, Matusow continued sneaking into casinos and even stole money from his mom to fund his habit. Luckily, he attended gambler’s anonymous meetings and eventually found poker in 1989.

Taught by a pro named Steve Samaroff, Matusow would go on to become one of the game’s most famous players. His loud-mouthed nature and winning ways have made him a camera-friendly pro.

“The Mouth” has won four WSOP bracelets to date along with over $9.5 million in tournament cashes. He was another player who, at one time, had a lucrative Full Tilt sponsorship.

Unfortunately, Matusow has battled substance abuse throughout most of his adult life. He even spent six months in jail in 2005 after giving ecstasy and painkillers to an undercover cop.

Things have gotten even worse for Matusow these days. He suffered a spinal contusion in 2014 and was temporarily paralyzed.

Matusow finally regained the ability to walk and play poker by 2017. Unfortunately, he lost his home and other possessions while unable to play the game for so long.

He’s made a comeback after winning over $100,000 in online cash games and participating in recent WSOPs. Matusow has won some money in tourneys lately, but nothing like he used to during his heyday.

Conclusion

Winning millions of dollars doesn’t guarantee one wealth and prosperity, especially in the gambling world. Some of the players on this list have won big, only to lose everything due to bad bankroll decisions and/or other problems.

Charles Wells, Erick Lindgren, Archie Karas, Brad Booth, Harry Findlay, Gus Hansen, Tom Dwan, and Ryazan all lost their money through poor money management. Dwan and Hansen are the only ones who seem to have maintained some level of wealth, in spite of their struggles.

Mike Matusow also lost his gambling fortune. However, he claims that this stems from a back injury, which left him unable to play poker for years.

Other gamblers like Billy Walters and Phil Ivey have suffered in non-financial ways. Walters is sitting in a prison cell after an insider-trading scandal. Ivey has spent more time in courtrooms than at poker tables in recent years.

Some of these gamblers still have the skills to make a comeback and get on the path to success again, but it’s unfortunate that they couldn’t have simply maintained their previous winning ways and avoided all the drama.

Michael Stevens: Michael Stevens has been researching and writing topics involving the gambling industry for well over a decade now and is considered an expert on all things casino and sports betting. Michael has been writing for GamblingSites.org since early 2016.