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Can you imagine how many gamblers have won and lost money throughout history? We’re not just talking about hundreds or even thousands of people. Hundreds of millions of people, probably even billions, have gambled something to try to win.

Since you are putting up money to win money, poker is considered by many to be gambling. Although, in the long run, the more skillful players will win the most money. Online poker sites offer all the popular games such as Texas Hold’em, Omaha, and 7-Card Stud, plus additional variations like Razz, H.O.R.S.E, and Badugi. He took investors for £400, claiming to fund a musical jump rope, but he used that money for a fabulous time in Monte Carlo. While there, Charlie took a crack at roulette. Somehow, Wells managed to play the game clean and remarkably won over a million francs during an 11-hour marathon. The man gained worldwide fame from his gambling exploits.

Almost all of these gamblers have failed. With so many to choose from, making a list of the 10 most successful gamblers in history might sound like a herculean task.

As it turns out, there are fewer success stories than you might think. Here are my picks for the 10 most successful gamblers in history.

1 – Edward Thorp

Edward Thorp is a math professor who literally wrote the book on card counting. Beat the Dealer was the first book about card counting that mathematically demonstrated that you could beat the house edge in blackjack by tracking the ratio of high cards to low cards left in the deck.

He personally used his card counting techniques in Lake Tahoe, Las Vegas, and Reno, starting with a bankroll of $10,000 provided by his friend Manny Kimmel. Their first weekend at the tables, they won $11,000.

Thorp was also one of the first card counters to use disguises to prevent casinos from backing him off.

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Keep in mind that he developed these card counting techniques in 1966, when a computer less powerful than your cell phone took up an entire room in a university somewhere. There were no personal computers to rely on.

He’s also known to have won at baccarat, backgammon, and roulette, using various other advantage techniques, some of which are now illegal.

2 – Billy Walters

Most people think of Billy Walters as the most successful sports bettor in the history of sports betting in all the popular Las Vegas casinos. He’s been winning sports bets consistently for 30+ years, which is certainly enough of a winning streak that it can’t be accounted for by a “lucky streak.”

His has a true rags-to-riches story, too. He grew up poor in Kentucky, and he was (more or less) orphaned before he was two years old. His grandmother had to raise him, as his father died and his mother ran off.

Not everything about his story is rosy, though. He was also convicted of insider trading and is serving five years in prison.

3 – Phil Ivey

When you’ve won 10 World Series of Poker bracelets, like Phil Ivey has, you can start to stake your claim at being the best poker player in the world. According to the Wikipedia page about Ivey, multiple sources have called him the best.

I don’t even have the time to list all of his poker tournament wins. There are just too many of them.

More interesting to my readers, probably, is the tale of how Phil Ivey got involved in an edge sorting scheme to make money. In 2012, Ivey won over $11 million playing baccarat in London.

But Crockfords, the casino where he was playing, refused to pay him because they caught him using an advantage play technique called “edge sorting.” The casino called it cheating, but Ivey claims that he was just making intelligent use of an imperfection in the playing cards in use.

Ivey had a similar experience with the Borgata, too. Litigation ensued. The courts ruled in favor of the casinos, agreeing that edge sorting constitutes cheating.

Who knows what Ivey will get into next?

4 – Chris Moneymaker

You gotta love someone with the last name of Moneymaker who goes on to win the Main Event in the World Series of Poker, which is what Chris Moneymaker did in 2003. It was a huge cultural event, because he won his entry into the WSOP on the internet. This resulted in a huge influx of players to online poker sites during the so-called “poker boom.”

You can read more about Chris Moneymaker in his autobiography, Moneymaker: How an Amateur Poker Player Turned $40 into $2.5 Million at the World Series of Poker.

One interesting note about the title of his autobiography, though. Moneymaker actually bought into the satellite tournament for $86, not $40. He just misremembered the details.

Moneymaker still plays poker and has continued to rack up winnings. He’s won over $3.5 million in his career, which includes the $2.5 million from his win at the WSOP.

5 – Don Johnson

Please don’t confuse this Don Johnson with the actor, who I love, but who isn’t a gambler (at least as far as I know).

The Don Johnson I’m referring to here is a businessman and a gambler who won over $15 million playing blackjack, and he did it WITHOUT using the counting cards technique in blackjack.

His run against the three Atlantic City casinos in 2011 and 2012 is historic now. It’s important to note that even though he wasn’t counting cards, Johnson was thinking like an advantage player. He insisted on blackjack rules that gave the house a small edge of only 0.26%.

He then negotiated a loss rebate deal with the casino that turned that small edge for the casino into an edge for the player. His losses were limited, which means that he didn’t risk much money compared to his potential win. Such a move is called a “positive expectation bet.”

It would be hard to duplicate Johnson’s success, as casinos are probably more sophisticated now, thanks to his large win.

6 – The MIT Blackjack Team

While I’m on the subject of blackjack, let’s include this group of students from MIT who counted cards as a team and took the casinos for millions. The MIT Blackjack Team isn’t a new organization either. They’ve been winning money from the casinos since 1979.

Prospective teammates had to pass a test, then they were thoroughly trained. Before being allowed to play with the team’s money, they had to demonstrate perfect play for the management of the team.

Besides traditional card counting techniques, the MIT Blackjack Team uses shuffle tracking and ace tracking techniques. It’s estimated that the techniques used by the team give them an edge over the casino in the 2% to 4% range.

They did not, however, invent the concept of team play in blackjack. Ken Uston is known for starting one of the first blackjack teams.

They even made a movie about the MIT Blackjack Team. It’s called 21 and stars Kevin Spacey. It’s an extremely loose adaptation of actual events, though.

7 – Doyle Brunson

Texas Dolly, which is Doyle Brunson’s nickname, retired in 2018, but his poker exploits are legendary. I’ve read that he invented Texas hold’em, although I don’t believe that’s actually true. He’s won the World Series of Poker twice, and he’s written multiple poker books, the most famous being Super/System.

Like Phil Ivey, who’s profiled earlier on this page, Brunson has a total of 10 WSOP bracelets.

Brunson is a member of a club that only includes four people.

If you’ve never read it, Super/System is definitely worth checking out, even though much of the language is dated.

8 – Stanford Wong

You’d be hard-pressed to find a better book about getting an edge at blackjack than Wong’s tome, Professional Blackjack. He owns his own publishing company, Pi Yee Press, and he’s a well-known gambling expert. Wong isn’t his real name, though, his real name is John Ferguson. He uses a pseudonym to stay one step ahead of casino security.

His last name has become a verb in the advantage play community. “Wonging” is when you count cards as an observer and don’t place a bet until you have an edge over the casino because of the count. It’s easy to understand why someone whose very name has become a verb used to describe a gambling technique would make a list of most successful gamblers in history.

9 – Richard Nixon

Richard Nixon was (obviously) a highly-flawed individual, but it’s hard to imagine leaving him off a list of most successful gamblers.

Even though he never won the World Series of Poker or any major poker tournaments, he’s a huge success story because he used his poker winnings to fund his political campaigns.

In the United States, becoming president is probably the pinnacle of success.

10 – Phil Hellmuth

My favorite poker player is Phil Hellmuth who has won 15 WSOP bracelets. His nickname is “the Poker Brat.” The first poker strategy book I ever read, in fact, was called Play Poker Like the Pros.

He’s also made several instructional poker videos.

My favorite thing about watching Hellmuth play is how emotional he gets. I read somewhere that he claims that he externalizes those emotions so they don’t come out in play. In other words, it only looks like he’s on tilt.

Conclusion

That’s my list of the 10 most successful gamblers in history, but you might have some gamblers you like better for your own reasons. If that’s the case, please feel free to pony up a name or two for consideration in the comments below.

Unbiased, “No Stones Unturned” Reviews by Industry Experts.

Ranked for Safety, Secure Payouts and Quality of Service.

You might want to read our comprehensive reviews.

So, you’re interested in finding the best online gambling sites available? Well, if so, you’ve definitely come to the right place!

Welcome to LegitGamblingSites.com, where our team of experts continuously researches and reviews online gambling sites from all over the internet in an effort to weed out unsafe, unethical sites and pass along the best options to our readers.

No matter what criteria you’re looking for, we’ve got recommendations for you. You can search by the country you live in, the sport you want to bet on, the type you’re looking for, or even more specific criteria like payout speed and real money wagering.

If it involves placing bets online, we have tips, strategies, and trusted online gambling sites that deal with that topic.

Our experts have determined that the websites listed above are the top gambling sites on the internet. However, the rankings and recommendations may change depending on what activities or factors that you prioritize most.

For example, we can provide the best online gambling sites available to US customers, legit places to bet on baseball, or the top online casinos at which to play slot machines.

While all of our trusted sites are both safe and reliable, some are better for specific activities than others. After all, a company that excels at live sports betting may not be your best option for playing poker or bingo.

It’s all about finding the best fit. That’s why we take the time to organize our website based on each particular variable, so you always get the best gambling sites for the activity in which you’re interested!

Best Online Gambling Sites by Location

When it comes to gambling online, sometimes the rules and legality of it all can be confusing. Depending on where you’re located, there are different laws that dictate which types of wagers are allowed, banking methods you can utilize, and websites you may be able to access.

Organizing our guides and recommendations by location makes it a breeze to identify legit online gambling sites that service your area!

We advise our readers to check out our location-specific pages to educate themselves on the legal status of online gaming and what options they may have.

In the United Kingdom, gambling is licensed and regulated, which makes finding safe gaming sites easy for residents there.

On the other hand, the United States has confusing online gambling laws. It’s illegal to operate an online gambling site or process transactions involving betting sites if you’re a banking institution, but it’s still legal for individual residents to play online. For this reason, people in the US must find reliable offshore gaming sites to give their business to.

You may find specific information about laws, regulations, and jurisdictions by following these links:

Our Lists of Best Online Gambling Sites for…

Best Gambling Sites by Type

Perhaps you have a specific type of online gambling site that you’re looking for, and you would prefer to focus on that particular niche. Rather than waste time with information that isn’t related to what you’re looking for, you can visit a page 100% dedicated to a single variety of gambling online. We’re always developing more pages, and we already have options like political betting and high-stakes gambling sites.

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We also organize the top online gambling sites by individual sports and leagues. On the following pages, you’ll find recommendations including the highest-quality gambling sites, helpful gambling tips, detailed resource guides, and articles breaking down various strategies to help you win more often. The more knowledge about a sport that you have at your disposal, the easier it will be to spot mispriced odds and earn money.

Best Betting Sites by Sports League

If you’re not concerned with specific types of online gambling sites or individual sports, you may want to maximize convenience by focusing on your preferred payment method. We provide lists of recommendations that cater to each of the most accessible means of banking.

Depending on your location, you may be required to utilize specific payment options. Otherwise, you may just be looking for legit gambling sites that accept banking types with the fastest payout speeds. Whatever the case, we’ve got you covered.

Why These Are the Best Online Gambling Sites

Quite a bit of work goes into vetting online sportsbooks and casinos to ensure we only pass along the most reliable, legit online gambling sites to our readers. There are numerous variables that are researched which impact both our recommendations and reviews. Here are some of the fundamental factors that we take into account:

• Safety and Legitimacy – There are tons of scammers and rogue gambling sites on the internet. Our purpose is to weed those out and only pass along safe, reliable, legitimate online gambling sites to our readers.
• History/Reputation – We also consider a site’s past performances when forming our recommendations. Websites with a history of dissatisfied customers or that have previously landed on blacklists are avoided.
• Quality Customer Service – The sites we pick have customer service sections with several contact methods. They also must actively monitor their communication channels and respond to issues in a reasonable amount of time.
• Variety of Wagers – Whether you’re sports betting or playing casino games, the more variety, the better. Not only will you avoid boredom, but you’ll also be able to pinpoint the exact scenarios on which you want to bet. This is particularly helpful when betting on sports.
• Multiple Banking Options – Our experts also prioritize gambling websites that accept numerous banking options. This gives you more control of your payout speeds and allows you to work around pesky banking laws that disallow specific methods, such as credit cards in the US.
• Ease of Use /Website Quality – A site worth recommending should have a straightforward sign-up and deposit process, be easy to navigate, and be well designed to maximize customer experience. Graphics quality becomes more important when engaging in live sports betting and playing certain slot games.
• Reasonable Payout Speeds – Rogue sites often manipulate payout speeds as a way to discourage you from withdrawing funds in hopes that you’ll grow bored and gamble the money away. Payout speeds are a significant factor in spotting legit gambling websites.
• Bonuses and Loyalty Programs – Most sites offer bonuses for signing up and making an initial deposit. These free plays and extra cash can add up to a significant amount. Loyalty programs reward players based on how much they wager and how often. The more you gamble, the more significant the gifts.
• Good Odds/Payout Percentage – Gambling is all about math and is frequently determined by the finest of margins. The recommendations we provide offer great odds on their games and competitive payout percentages.

If you’d like to learn more about the importance of finding safe online gambling sites and how we determine if a website is legitimate, please enjoy the articles linked below:

Real Money Gambling

You’re not really gambling until there’s real money on the line! Playing the free games for a few minutes can be interesting, but nothing gets the blood pumping and the adrenaline flowing like having legitimate action on the game. And you know what comes with real money risks? Real money rewards!

With the incredible convenience of online gaming, suddenly you have the potential to hit the jackpot at any moment. You could be standing in line at the store or lounging on your couch, and the next thing you know, your life is changed forever! The only way to win is to play the game.

When it comes to real money online gambling sites, there are options available for every game, sport, and currency type you can imagine. Tens of billions of real dollars are wagered online every year, a number that increases each year. Isn’t it time for you to get in on all the fun?

Online Gambling Guides

While we are definitely passionate about finding the top online gambling sites for our readers, our assistance doesn’t end there. We also spend countless hours researching strategies and creating guides to help you succeed in whatever wagering activities you enjoy. We break down the underlying concepts that dictate gambling, provide tips for maximizing your winning percentage, and write strategy guides for various casino games and sports betting.

Casino Guide

Before diving in and playing in the casino, you should consider reading our casino gamblers’ guides. We break down both the rules and the odds for various slot and table games. Our writeups also include the best possible playing strategies to maximize your chances of winning.

Additionally, we’ve broken down notions such as casino bonuses and the house edge, which play an instrumental role in determining if you will win or lose over the long term. Gambling online can be a fun, mindless way to pass the time if that’s what you’re looking for. But if you are playing to win, with dreams of jackpots in your head, you’ll want to first get acquainted with the information our experts have prepared for you.

Sports Betting Guide

Our best online gambling sites might be great, but they won’t do you much good if you don’t know how to place your bets, which is why we’ve put together various guides to help you better understand how to bet on sports.

Our gamblers’ guides are especially beneficial for those that are interested in sports betting. Wagering on sports can be a confusing proposition with all of the unique terminology and types of bets. Furthermore, the majority of casual bettors think the object of placing sports wagers is merely picking winning teams. We’ve organized all of this information so that you can talk about and make sports gambling picks with the best of them!

Through our guides, you’ll learn about betting with value in mind, determining real probability, and calculating implied probability based on the odds. We also break down the many unique types of sports bets, including tips for approaching each variation. Most importantly, we offer guides explaining how critical bankroll management is and teach readers how to finance a bankroll and organize a staking plan.

Other Popular Guides

We also have dedicated pages for a variety of other online gambling topics. If it involves wagering money on some game or event, we’ve got you covered. It doesn’t matter if you like playing online scratch cards or prefer to spend your day in a competitive poker tournament; there’s something for everyone to learn.

When you’ve completed reading all of the resource articles that catch your attention, you’ll have a solid foundation on which to build your gambling career. Experiencing success through gambling starts with acquiring knowledge and developing a full understanding of what’s going on and what you can do to improve the likelihood of winning. So, take the time to get acquainted with the guides that cover whichever games or wagers you’re going to try. You’ll thank us later.

Popular Gambling Blog Articles

Our team of experts is continuously paying attention to current events and writing blog articles on a vast range of topics and ideas. We make picks for most upcoming sporting events, break down in-depth gambling strategies, and share our opinions on a variety of subjects. This is where you can find an ever-changing stream of fresh content to keep you interested and in the know.

Make sure to keep checking back here to find the newest blog posts. These articles are typically written on topics the writers are very passionate or knowledgeable about, and so they’re a great opportunity for you to pick up expert advice without having to pay some shady handicapping service. Plus, sometimes they’re really funny!

The Importance of Responsible Gambling

Gambling can be a gratifying hobby and form of entertainment, but that doesn’t mean it’s without risk. Certain personality types have adverse reactions to the rush that online gambling provides, which can lead to compulsive behaviors and problem gambling.

Thankfully, there are strategies for managing your money and staying responsible when gambling that can help you avoid the pitfalls of addiction. Understanding the ideas behind bankroll management and how to develop an effective staking plan will exponentially increase your chances of staying a responsible gambler.

To those already struggling with a gambling addiction or who know someone who is, we’re here to help you as well. In our “Gambling Responsibly” guide, we cover where to get help when experiencing problem gambling. We also share advice on how to help a friend who may be experiencing these issues.

We are all here because we enjoy the gambling. Whether it’s handicapping the game or playing blackjack that gets our juices flowing, we all experience an absolute thrill from making the right pick and winning some money. But that thrill requires a lot of discipline and responsibility. Just like anything else, moderation is key. If you aren’t capable of regulating your bad habits, your best bet is to avoid the topic altogether.

Frequently Asked Questions

Why does location matter when choosing a gambling site?

Online gambling laws vary from place to place. Depending on where you’re located, the requirements a website must adhere to when accepting customers may change. For example, gaming websites housed in the United Kingdom must be licensed and heavily regulated by the gaming commission in their country. These sites will not accept players from the United States.

How do I know when a site is legit?

Legit gambling sites typically share several key attributes.

1. They process payout requests quickly
2. They are not included in any industry blacklists
3. They provide several timely payout options
4. They promptly respond to customer service issues
5. They are licensed and regulated in a thorough gambling jurisdiction
6. You find them on our list of recommended sites

Is gambling online legal?

The answer to this question depends on where you live. However, in most parts of the world, an individual that’s gambling online is not breaking the law by doing so. Even when there are laws on the books, they aren’t enforced. In the United States, there are laws against operating an online betting site, and banks can’t process transactions with known gambling organizations, but the individual bettor is within their rights to gamble online using offshore websites.

Is online gambling fair?

Yes, as long as you’re playing on a legitimate gambling site. Websites that are under government regulation have their software tested to ensure the games are random and fair. Most games are governed by random number generators which decide which cards or symbols are dealt. These are kept under strict controls and cannot be altered without permission from the regulatory body.

Is it possible to cheat at online gambling?

No, not without hacking the software. If you do that, expect your account to be frozen and for the authorities to be alerted to your location well before you ever cash out any of the stolen funds.

How do I keep my information and gambling accounts safe?

First, make sure you’re only using reliable gambling sites that have been researched and vetted by experts. Next, decline the option to have your computer or mobile device save your password for quicker logins. That way, someone with access to your computer or phone can’t just log in and withdraw your money. Use a creative password with lots of upper and lowercase letters, numbers, and symbols. Don’t use pet names, kid’s names, or predictable words.

What’s an offshore gambling site?

Offshore gambling sites are casinos or sportsbooks that are available to US customers but aren’t located within the United States’ jurisdiction. Because operating online gambling websites is illegal in the US, these websites are not licensed or regulated by the government. Most offshore gambling sites that accept US citizens are based in the Caribbean and are held to the rules and regulations in their particular jurisdiction.

Can I play on my mobile device?

Yes, the majority of online gambling sites are compatible with mobile devices. It’s also becoming more popular for websites to create their own apps, making access to their games more convenient and helping them to run smoother. Some gambling sites are still behind in this regard, but it’s not common.

I was just offered a bonus. What’s a rollover?

Many of the entry-level bonuses come with significant strings attached, usually in the form of rollovers. Rollovers are a requirement for the amount of money you must wager before being allowed to withdraw money. So, if you accept a $100 bonus with a 25x rollover, you’ll need to place a total of $2,500 in bets before having the ability to request a payout. The higher the rollover, the more unlikely you are to win enough to meet the requirement before losing your bankroll. This is one of the many factors we consider when selecting the best online gambling sites recommended above.

Do online gambling sites use real money?

Yes! Many will allow you to play for free as well, but the sites that you’ll find here mostly deal in real money. You have to bet real money to win real money!

Are the gambling sites that you recommend licensed and regulated?

They are! We do our best to make sure all of our recommended sites maintain their licenses. It is possible for a place to let their gaming license lapse, depending on their jurisdiction, but it’s extremely rare.

What does “payout percentage” mean?

The payout percentage is the number of winnings a game or machine is programmed to return based on a percentage of the amount wagered. The higher the payout percentage, the more favorable the odds are for the player.

Why do online gambling sites require personal information when signing up?

Any reputable online gambling operation has rules to follow, namely that you’re of age to be playing. Depending on the jurisdiction, gamers must be either 18 or 21 years old to bet.

I’m new to online gambling; where’s the best place to start?

What’s the benefit of gambling online rather than in a land-based casino?

1. Convenience – you can play any game or place any bet from anywhere
2. Better odds – without all the overhead and upkeep that comes with running a building, online gambling sites can offer better odds and still make money
3. Variety – online casinos can offer more types of slots and table games than even the most massive brick-and-mortar spot could ever dream of having the floor space for

How can I tell that a gambling site is a scam?

1. They change their terms and conditions
2. They have negative customer reviews complaining about slow payouts or unfair treatment
3. They make up rules to avoid paying out customers. For example, accusing players of being professional gamblers or cheating
4. You find them on industry blacklists

Do I have to download any software?

It’s not typically required, but there are times when you may. Some online gambling sites and poker rooms offer downloadable software that speeds up the processing time and creates a more stable gaming experience. If you’re opposed to this, there are numerous no-download slot sites at your disposal as well.

Which regulatory jurisdictions are the best?

• Alderney
• Antigua and Barbuda
• Gibraltar
• Isle of Man
• Kahnawake
• Malta
• Panama

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Why can’t I access certain online gambling sites in other countries?

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What’s the best way to win money gambling online?