A lot of times, when you search Google or Bing for information about “gamblers,” you’ll find sad tales of gambling addicts who lost every penny they had. Some of them even took their own lives. And those are stories that need to be heard, to be sure. But it’s also important to talk about the other side of the story. Some gamblers are successful. Some of them are even examples of extreme success.If gambling is one of your hobbies, you might do well to pay attention to the similarities between successful gamblers.

That’s one of the reasons I wrote this post. I wanted to see what successful gamblers did that other gamblers don’t do. I’ve tried to cover a wide variety of gambling success stories below. I’ve included blackjack players, poker players, and sports bettors. And just as a little preview, here’s one thing I learned about all winning bettors: They’re unafraid of risk, and they do their best to bet when the odds are on their side. Read on for more.

1- Edward O. Thorp

Edward Thorp GamblerI didn’t realize it until I started writing this post, but Edward Oakley Thorp is still alive. He was born in 1932, so he’s 86 years old. He’s known for his gambling career, but like most gamblers, he has a variety of experiences and life details to share. He’s a math professor and a hedge fund manager. He’s written books. He specializes in applying probability theory to gambling in general and to blackjack specifically.And that’s what he’s best known for as a gambler. He wrote a slim book called Beat the Dealer, which is the 1st book to demonstrate mathematically that blackjack is a winnable game. Beat the Dealer could be considered the 1st book about card counting, and I’ve seen Thorp referred to as “the father of card counting.” Card counting isn’t new, by the way. Thorp did his mathematical research into the concept in the 1960s, in fact. He had to use an IBM 704 for his computations, and it required programming to pull off.

Thorp went on to apply that research to actual blackjack games in Nevada casinos. He started with a $10,000 bankroll. He won $11,000 during his 1st weekend of playing blackjack in Reno. Even then, Thorp knew that the casinos would frown on this practice, so he was not only one of the 1st card counters, he was one of the 1st card counters to use a disguise.

It didn’t take long before gamblers started hearing about this advantage technique. In fact, Thorp became a celebrity of sorts right away. He published Beat the Dealer in 1966 to wide acclaim. In fact, it sold over 700,000 copies, putting it on the New York Times best seller list. Thorp is also famous (albeit less famous) or inventing and using a wearable computer in a casino. At the time, it probably wasn’t illegal, although it certainly is illegal now.

Blackjack and card counting have come a long way over the last few decades, but it’s certain it wouldn’t be where it is without the groundbreaking work of Ed Thorp. And Beat the Dealer is still in print, by the way.

2- Billy Walters

Billy Walters GamblerBilly Walters is probably the most successful sports bettor in Las Vegas, but he isn’t successful at everything. Sure, he’s won at sports betting consistently for 3 decades. But he’s been less successful as an investor. He was arrested and convicted of insider trading. He was sentenced to 5 years in prison and had to pay $10 million in fines.He got started gambling early—he bet paper route money on the Yankees to beat the Dodgers in 1955 when he was just 9 years old. He lost. In fact, he continued to be a net loser as a gambler into the 1980s. He claims to have lost over $50,000 gambling by the time he was 25. He turned things around in the later 1980s, when he was in his 30s. He found a biased roulette wheel and won $3.8 million on it. He eventually became part of a team of gamblers who won over a million dollars in the late 1980s.

Walters is best-known, though, for launching “The Computer Group.” For 39 years, this group has consistently won at sports betting. In fact, they’ve only had a single losing year. They bet on basketball and football. Walters is so well-known that he has to place his bets using runners. The bookmakers won’t take his action if they know it’s him placing the bets. He claims that in a good year he earns over $50 million on sports betting.

More recently, Walters got into trouble for making $43 million in profits on private information—insider trading. He had an in at the company, Thomas C. Davis, who was feeding him information from 2008 to 2014. This info helped him avoid losses and make profits.

In 2017, Walters, was convicted of making $43 million on private information of Dallas-based dairy processing company Dean Foods. Walters’s source, company director Thomas C. Davis employing a prepaid cell phone and sometimes the code words “Dallas Cowboys” for Dean Foods, helped him from 2008 to 2014 realize profits and avoid losses in the stock, the Federal jury found. He gained $32 million.

He’s now serving prison time in Pensacola. He should be released in early 2022. All of which just goes to show that it takes more to succeed in life than just succeeding at gambling. Walters is a good example of the power of persistence and single-minded pursuit of a goal, though.

3- Nick Dandolos

Nick Dandolos GamblerIf you’re of a certain age, you’ll know Nick Dandolos by his more famous epithet—Nick the Greek. He was a professional gambler who loved high stakes. The stories about Nick the Greek are now legend.Nick the Greek came from a wealthy family and had a philosophy degree from Greek Evangelical College. He came to the United States with a $150/week allowance, which at the time was a significant amount of money. He started out in the U.S. living in Chicago, but he moved to Montreal to bet on the ponies.

He’s probably most famous for the size of his bets, both the ones he won and the ones he lost. He won half a million betting on horses before moving back to the Windy City. He proceeded to lose every penny of it playing craps and poker. He was such a colorful character, though, that he attained celebrity status. People just wanted to watch him gamble.

He’s most famous for his heads-up poker game with Johnny Moss, which lasted for over 5 months, with only rare, occasional breaks. This match is often cited as the 1st “World Series of Poker.” He lost $2 million to Moss before finally telling him “Mr. Moss, I have to let you go.” As an old man, Nick the Greek was almost penniless. He stayed in action, though, playing $5 limit 5-card draw. It’s estimated that he won and lost over $500 million in his lifetime.

4- Don Johnson

Don Johnson GamblerHe’s probably my favorite gambler on the list. In 2011, Don Johnson—no relation to the actor—won over $15 million playing blackjack in Atlantic City. He didn’t even have to count cards. He was well-known already as a high roller when desperate Atlantic City casinos were practically begging whales to come play. Johnson used his leverage and the casinos’ desperation to negotiate a blackjack game which had almost no house edge.More importantly, he negotiated a 20% rebate on his losses over $500,000. He beat Tropicana for $6 million. He then beat the Borgata for $5 million. He wasn’t finished.He then took Caesars for $4 million. Johnson was wagering 6 figures per hand, too.

Tropicana and the Borgata still welcome his action, although they no longer honor the blackjack agreement they had with him. Caesars, on the other hand, don’t welcome Don Johnson any more. That’s a sign of a successful gambler, by the way—when a casino won’t let you play there any more.

5- Chris Moneymaker

Chris Moneymaker GamblerCould you ask for a better name for a famous, successful gambler than “Moneymaker?” I can’t think of any. Chris Moneymaker is best-known for winning the World Series of Poker in 2003. He was the 1st poker player to qualify for the event by playing poker on the internet. This was the beginning of the Poker Boom.Before he won the World Series of Poker, he was an accountant. He bought into a satellite tournament on PokerStars for $86. No one knew who he was at the time, but it didn’t take him long to get noticed. The prize for 1st place that year was $2.5 million.

He became an instant celebrity. Moneymaker’s win at PokerStars, by the way, was part of a marketing strategy. The executives at PokerStars knew that if they gave away enough seats to the World Series of Poker, they had a good chance of getting one of their players into the top spot. And it worked. PokerStars is now the largest online poker site in the world.

You can read more about Chris Moneymaker in his memoir, Moneymaker: How an Amateur Poker Player Turned $40 into $2.5 Million at the World Series of Poker. Moneymaker continues to play poker, and he’s won or placed in several other large tournaments (including multiple WSOP events) with 6-figure prizes. In fact, since winning the WSOP, he’s won at least another $1.1 million.

6- Stanford Wong

Stanford Wong GamblerIf you’ve noticed multiple blackjack personalities on this list, it’s probably because I really like blackjack. Stanford Wong is another blackjack expert, although that’s just his pen name. His real name is John Ferguson. He’s famous for his 1st book, Professional Blackjack, as well as a whole mess of additional blackjack books he’s written since then.He also created a computer program which analyzes blackjack odds. It had the clever name of Blackjack Analyzer. He owns his own publishing company which specializes in gambling books—Pi Yee Press.

Wong books available from his publishing company include:


  • Professional Blackjack
  • Blackjack Secrets
  • Basic Blackjack
  • Professional Video Poker
  • Optimal Strategy for Pai Gow Poker
  • Casino Tournament Strategy
  • Betting Cheap Claimers


Current Blackjack News is an ongoing newsletter aimed at serious blackjack players. Wong has been publishing this newsletter since 1979.  You can also buy multiple software programs to improve your gambling from Wong and his publishing company. He’s been playing blackjack since the mid-1960s. He’s so well-known in the professional blackjack community that he has his own advantage technique named after him, “wonging.”

A card counter who waits and watches for an opportunity to get into a good deck before playing is engaged in wonging. Some casinos don’t allow players to enter a game in the middle of a shoe. This is a countermeasure meant to thwart Wong’s followers from using that technique to get a bigger edge. Like many professional blackjack players, Wong also ran his own team of advantage gamblers, although they specialized in taking advantage of +EV casino tournaments. Anthony Curtis, of Las Vegas Advisor, played on his team at one time.

Wong now promotes dice control in craps. I’m skeptical that this is really a thing, but I’ve read some well-respected gambling experts and writers claim that they’ve seen it work. The idea is that even if you can’t completely control the outcome of a roll of the dice, you only have to influence it a little bit to turn the odds in your favor.

7- David Sklansky

David Sklansky GamblerHe’s one of my favorite poker writers, and I’m in the middle of his book DUCY right now. He’s had a fascinating career as a gambler, and like many successful gamblers, he’s also become a successful gambling author. Unlike many professional gamblers turned writers, though, Sklansky actually has a knack for writing well.He’s won 3 different World Series of Poker events, although they were years ago. He spends less time playing in the World Series of Poker than he does in cash games, though. I saw him playing in the high limit room at the Bellagio one time.

Among other things, his immunity to tilt is part of what makes Sklansky a famous and successful gambler. When my buddy Todd and I were playing at the Bellagio, Todd tried hard to get me to go harass Sklansky until he tilted. I suspect I wouldn’t have been able to get near him, even if I had been drunk enough to take Todd up on his dare. He’s won over $1.3 million in poker tournaments, but I suspect he’s won much more than that playing in ring games. He lives in Las Vegas, which makes sense for a professional gambling expert.

Anyone would be wise to read the book he co-wrote with Mason Malmuth about Gambling for a Living. I knew nothing about Texas holdem strategy when I read it, but after I finished that section of the book, I won $6000 in the 1st online Texas holdem tournament I’d ever played in. True story. That doesn’t mean you’ll see the same results. But there are a lot of great insights in that book.


So you wanted to read about successful gamblers, and there you have it—7 profiles of gamblers who have succeeded. I can’t say that they’re all role models in every respect. In fact, I flat out recommend that you DON’T engage in insider trading like Billy Walters did. He’s an old man. It’s awful that he’s going to live so many of his remaining years behind bars. And he could have prevented that, too.On the other hand, you can learn a lot from most of the names on this list. For one thing, they all learned to put themselves into situations where they could gamble with a mathematical edge. They were all also willing to take the risks necessary to succeed as gamblers.

Most importantly, none of them ever gave up, even when things weren’t going well. I had a boss who told me one time that the world belonged to monomaniacs. When it comes to gambling, I suspect he was right.

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