Professional gambling isn’t usually viewed as a happy profession. Even when players are highly successful, they sometimes blow their fortunes later through other forms of gambling and/or bad decisions.
But this isn’t to say that every pro gambler ends up in misery. In fact, some professionals have retired rich and happy.
I’m going to cover seven such gamblers who made a fortune before retiring from their respective games. Some of these former pros still gamble occasionally, but they no longer do it on a full-time basis.
Haralabos Voulgaris (a.k.a. H-Bob) is quite possibly the most successful NBA bettor of all time. He developed a system in the early 2000s that allowed him to take advantage of inefficient halftime totals.
Voulgaris noticed that sportsbooks were failing to account for variables that led to higher fourth-quarter scoring. He began taking the “over” again and again on second-half totals, which helped him win millions of dollars.
He also studied various NBA coaches and learned how Eddie Jordan, Byron Scott, and Jerry Sloan managed games. This knowledge helped him further pad his immense winnings.
However, sportsbooks have a way of catching on when sharps develop a highly successful system. Such was the case with H-Bob, who suddenly started seeing his results go downhill.
Bookmakers figured out his halftime system and began making adjustments accordingly. This forced Voulgaris to go back to the drawing board and find a new winning strategy.
He did exactly this by hiring a mathematician who helped him develop a betting algorithm. This program was so successful that Voulgaris could use it to accurately predict how games would go on a per-possession basis.
He even began using the algorithm to successfully predict how long players would last in the league. One NBA team took notice of his incredible knowledge of the game and asked him to consult on their player acquisitions.
Voulgaris’ dream was always to transition out of sports betting and into an NBA front office, but this opportunity with the unnamed team didn’t result in the gig he was looking for.
H-Bob did fulfill his dream in 2018, though, when Mark Cuban and the Dallas Mavericks hired him as their director of quantitative development. He’s now using the same skills that helped make him a sports gambling success to improve the Mavericks’ roster.
Hac “Trex313” Dang and Di “Urindanger” Dang played online poker during the game’s golden age in the mid-2000s. The brothers, who shared an account, managed to win over $10 million in profits at Full Tilt Poker before retiring.
They took on some of the greatest high-stakes legends to ever play the online game, including Phil Ivey, Patrik Antonius, Tom Dwan, and Ilari Sahamies. But they eventually got tired of the grind and wanted to pursue a different challenge.
The Dang Brothers definitely found this challenge upon opening a restaurant called Chasin’ Tails in 2012. This Virginia-based joint offers different types of Cajun seafood dishes.
Much like with poker, they’ve had a lot of success with Chasin’ Tails and have transformed it into a chain. The Dangs actually used some of their winning poker techniques to build up the restaurants, including studying many aspects of the industry.
But their journey to this point was far from smooth. They struggled shortly after opening and received a lot of bad reviews.
According to ARL Now, they particularly had trouble in the winter of 2013. Following a successful summer, customers stopped coming in.
Seafood restaurants naturally struggle more during the cold weather. But Chasin’ Tails also hurt themselves by taking over an hour to prepare certain dishes and hiring the wrong general manager.
“We tried to do whatever we could to make customers happy,” said one of the brothers. “We took responsibility. It was our fault. It’s our job to make the experience as good as possible.”
They were able to save the restaurant in the spring, though, when customers began filtering through the doors. The crew also reduced the wait time on meals to a more acceptable 20 minutes.
The Dangs said that they were motivated to improve after reading a number of negative Yelp reviews.
“Great food and very cool set up,” one customer wrote in May 2012. “Worst service I have had in years.”
“Overall, the food is good,” another customer wrote in the same month. “The downside is the service. Our server was very nice, but he placed our order and then entered the witness relocation program.”
Lucky for the Dangs, those days are long behind them. They now feature a thriving restaurant chain that’s been successful enough to continue expanding.
Don Johnson was a relatively unknown gambler until 2011 when he dominated Atlantic City casinos to the tune of $15 million.
Johnson, who previously worked as a state gaming regulator and developed horseracing software, was seen by casinos as a recreational high roller. While he had the money to play high stakes, gambling establishments didn’t view him as a threat.
What they didn’t realize, though, is that Johnson is a mathematical whiz who knew exactly how he could gain an advantage over the house.
Atlantic City casinos were in the midst of a huge recession and desperate to attract big-time gamblers like Johnson. They, therefore, let him negotiate for better blackjack rules, rather than typical high-roller comps like a penthouse suite and limo transportation.
One specific concession they allowed him included a 20% loss rebate on losses totaling over $500,000. This rule let him recoup up to $100,000 after a bad session.
Johnson also asked that he receive a free bet anytime the dealer made a mistake. Considering that he was betting up to $100,000 per hand, this rule offered a lot of value if the dealer messed up.
When it came time to play blackjack, Johnson did everything he could to throw off the dealer. He turned the game into a party by bringing an entourage of friends and hiring porn stars to pose as their girlfriends.
The end result included $15 million in profits from 2010 to 2011. He especially victimized the Tropicana, winning $6 million off them.
Johnson can never play the game again with the same edge he had for obvious reasons. No casino will ever underestimate him again.
But he’s likely not too worried about this considering that he’s already won far more money than most gamblers could ever dream of. He’s taken a portion of these winnings to enjoy life, including partying with everybody from Bon Jovi to Pamela Anderson.
Dan Colman got his start in the poker world by playing online under the screen names “riyyc225” and “mrGR33N13.” He gained minor fame early on by becoming the first internet grinder to win $1 million in hyper-turbo tournaments in a single year.
2014 would truly be his breakout year, though, as he began racking up several notable live tournament cashes. These results include winning the EPT Grand Final ($2.13 million) and the WSOP Big One for One Drop ($15.3 million).
The latter victory is what put Colman on the map and gave him a stage to express his seemingly radical poker views. He was apathetic after winning the One Drop and later wrote a scathing post directed at the game.
Here’s one excerpt from his post:
“First off, I don’t owe poker a single thing. I’ve been fortunate enough to benefit financially from this game, but I have played it long enough to see the ugly side of this world.
It is not a game where the pros are always happy and living a fulfilling life. To have a job where you are at the mercy of variance can be insanely stressful and can lead to a lot of unhealthy habits. I would never in a million years recommend for someone to try and make it as a poker pro.”
Colman wrote this at a time when the game was still looking for ambassadors to pump poker up and help ignite a second boom. He was, therefore ridiculed by many within the poker community afterward.
But this didn’t keep him from continuing to play the game. He earned plenty of six-figure scores in the aftermath of his magical 2014 campaign.
Colman previously said that he didn’t see himself playing the game forever. He looks to have stopped playing professionally, considering that he hasn’t cashed since 2017.
Even if Colman never cashes again, he’ll be remembered as a legend with nearly $30 million in live earnings to his name.
Fedor Holz is a German poker phenom who’s had more success than any young player in history. Despite being just 26 years old, he’s already earned $32.5 million in live tournament winnings.
Holz had his first major score in the 2014 PokerStars World Championship of Online Poker, where he collected $1.3 million for first place. He eventually parlayed these winnings into the greatest high-roller tourney run in history.
From late 2015 until the end of 2016, he won over $17.5 million through live events. This run was highlighted by a victory in the 2016 WSOP High Roller for One Drop ($4.98 million).
Holz has since announced his retirement from the game. But he still plays poker — and plays it well. Case in point, he took second place in the 2018 WSOP Big One for One Drop ($6 million).
Nevertheless, he only plays around “5%” the volume he used to. Now extremely wealthy, Holz is instead focused on running “Primed Mind.”
Located in Vienna, Austria, this startup company is based on developing “creative systems that will expand human potential.” They’re working on technologies to help people perform at their highest level.
They’ve since developed a Primed Mind app that works to enable users to visualize their success and properly set goals. Primed Mind is useful for people from all professions, not just poker.
Joseph Jagger was an English engineer who used his skills to win what amounts to millions of dollars through roulette. His gambling tale began in the 1870s when he deduced that certain roulette wheels may offer biased results due to wear and tear.
He hired six clerks to visit Monte Carlo and record roulette results in hopes of finding a biased wheel. He used their data to figure out that one wheel favored a certain set of numbers.
Jagger traveled to Monte Carlo himself and began betting on these numbers. According to Victor Bethell’s 1901 book, Monte Carlo Anecdotes and Systems of Play, Jagger won £120,000. This amount would be worth £12 million today when adjusted for inflation.
He might have won more money if casino staff hadn’t caught on to his winning ways. They switched the wheels around at one point, causing him to take on heavy losses.
Jagger was eventually able to find the biased wheel again and keep winning. But the casino used the same tactic a second time, at which point Jagger could no longer find the wheel.
He still left Monte Carlo a very rich man and became the first-known roulette advantage player. Jagger also wisely quit while he was ahead and never played the game professionally again.
Gonzalo García-Pelayo is a Spanish music producer and film director who became a roulette pro in the 1990s. Possibly inspired by Jagger and other roulette winners, Pelayo decided to look for biased wheels in Casino Gran Madrid.
He recruited his family members to help him record roulette results there. They found a biased wheel and milked it for hundreds of thousands of dollars in profits.
Casino Gran Madrid eventually became suspicious, which prompted the Pelayos to hit the road and start beating other European casinos. They eventually won over $1 million before European gambling venues began networking and warning each other about this advantage roulette team.
The Pelayos took their act to Las Vegas for one grand finale. They were able to run their overall winnings up to an estimated $2 million before they started taking heat from the Vegas casinos.
At one point, Gonzalo passed out from a combination of exhaustion and stress. This incident convinced the family to head back to Spain and retire with their fortune.
Unfortunately, roulette wheels are so well-designed today that it’s very difficult to pull off the same feat as Pelayo and Jagger. But these legends show that the game can be beaten with the right wheel.
Many gamblers dream of getting rich through casino games. But even if every gamble did somehow realize these dreams, few would be able to exit with their profits.
A successful poker player might lose their winnings in the craps pit, or a winning sports bettor might blow their money on high-stakes baccarat.
But the seven gambling legends discussed on this list have had no such problems. In fact, they’ve all successfully retired and have moved on to other pursuits.
Thanks to all of these former pros, you can see that not all successful gamblers end up broke. Some of them even use their fortunes to succeed in other pursuits.
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