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.
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- Online slot machines are the favorite game of most gamblers around the world. The main goal of which is to wait for a winning combination or get bonuses/bonus rounds. This game is one of those that are easy to learn, but hard to master, which automatically makes it accessible and interesting for both beginners and professionals.
- Here’s a summary of some of the biggest roulette wins ever documented: Charles Wells – 2 Million Francs (1881, Monte Carlo) Ashley Revell – $270,000 (2004, Las Vegas) Chris Boyd – $440,000 (1994, Las Vegas).
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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.
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.
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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.
In this article:
Select a preference:
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Room | Bonus | Rating | Get the Offer |
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If you haven't found the perfect bonus in the list, let's continue and let's see what else is there.
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Room | Bonus | Rating | Get the Offer |
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Room | Bonus | Rating | Get the Offer |
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Important Notice: Free Spins for UK Players
Given the restriction applied by the UK government to online gambling for real money, you can't play on all the sites that offer free spins bonuses.
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Room | Bonus | Rating | Get the Offer |
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While this might seem an unnecessary limitation, the UK legislation on gambling is your best ally to avoid frauds and be sure to play your games in a safe environment.
Also, it is your only way to be sure to get paid when you win real cash. As a UK player, you can always reach out to the UKGC for support and to seek help in case a casino doesn't behave as they should.
A Note on Geolocation
When you visit this page from the United Kingdom, you only see casino sites and free spins offers that are available in the UK .
If that describes you, the free spins casino bonuses you see here are available to UK players.
You can use the welcome spins to play online slots from the UK or go for a bonus with deposit required if you plan to secure a better casino promotion.
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On CasinoSmash, we use special geo-location filters.
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About This Page
As you should know by now, this page features the most comprehensive collection of free spins bonuses you can find in 2020 - and you don't need to take our word for it.
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In case you are new to the world of online gambling, here's a quick guide to understanding the differences between these different types of free spins bonuses.
No Deposit Free Spins on Casino Slots
This is every beginner's favourite casino bonus and the only one you get without a deposit.
A deposit-free bonus is an ideal promotion play on a new website or to try a new game.
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The Pros | The Cons |
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It's a free bonus | Not many free spins |
You don't risk anything | Limited selection of games |
You can win real money | Not a standard bonus |
Winning real cash with no deposit spins is not a walk in the park.
No deposit spins come in a very limited number (forget the 100 or 500 free spins offers), meaning you get fewer chances to hit a good win with them.
This type of casino bonus can come with hard-to-meet wagering requirements too.
Free Spins on Deposit
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Think of this as 'a fee.' A small one you need to pay to unlock some free money and bonus spins to have a go at real money slots and more.
Like the no deposit offers, these bonuses are subject to specific wagering requirements too.
The Pros | The Cons |
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A lot more free spins | Not free |
Often in combination with match bonuses | T&Cs apply |
More games available | - |
Free Spins Terms and Conditions
From the number of times I have mentioned the words 'terms and conditions', you should know this is one of the key elements to using free spin bonuses the right way.
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Term | What does it mean? |
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Withdrawal Fee | Some casinos apply a fixed fee on all withdrawals (e.g. 2% of the sum you want to cash out) |
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How to Win Real Money Online
Wouldn't it be great to win real money online with one click?
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Unfortunately, you can't expect that the free spins on this page will make you rich or that you will win cash every time you play free slots.
Although many of these bonuses let you play real money slot machines for free with the opportunity to win cash online - don't forget winning money in gambling isn't easy.
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Here's a list of simple tips that will help you to get more chances to get a positive result.
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Here's an overview of the most popular Slots you can play with real money free spins this month.
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Free Spins FAQ
Depending on your location, you can use free spins offers to win real money prizes. Each offer's terms and condition include details on how much you can win and what you need to do to cash out the money.
You can browse through this list to see all the casino sites that give you the option to win money online with free spins.
Slot machines with a high Return to Player (RTP) are those where you have better chances to win. In general, any slots with an RTP of 96% or more is the right choice.
Real money free spins are often connected to limited games, so we compiled this list of the top games to play if you want to spin to win real cash.
Since every US state adopts a different approach to online gambling, you can win real money online only if you are in one of those where real money casino games are allowed. To know what's available for you, check out this list.
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If you are in the UK, you can only win real money for free with the bonuses offered on UKGC-licensed websites. If you don't know all the sites for UK players, visit this list.
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You can play free slot games from mobile if the casino offers a mobile version of their games. Some casinos also offer extra mobile casino free spins to encourage their customers to play from iPhone and Android.
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