• Most Money Ever Won In A Casino Poker
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She was told the machine had malfunctioned and that the most the casino could do is give her the last prize she'd won of just over $2 and a complimentary steak dinner. She is suing the casino and IGT. There's one thing all of these players have in common. They never expected they'd win the jackpot when they placed their small bets.

Dec 12, 2018 Once, a few years ago, on a spur of the moment excursion to Maryland Live! Casino my buddy and I had quickly (4–5 hrs.) blown through our original bankrolls of $1000 and $1500. Jan 25, 2008 The most heartbreaking losses always come from naive college kids or the regular single parents but the largest loss I've ever seen was pretty entertaining. There's a regular at our Casino that owns his own company but also used to scam other casinos by having an inside man at his bank confirm credit over the phone that the player did not have. “Multiple times per week we get high rollers in who win or lose over $1 million. The most I ever saw a person lose was about $9 million in one night. While that may seem like an obscene amount of money to you or I, that’s what he budgeted himself to gamble that trip. He came knowing he may lose $9 million.

It sounds like a homework problem out of a high school math book: What is the probability of rolling a pair of dice 154 times continuously at a craps table, without throwing a seven?

The answer is roughly 1 in 1.56 trillion, and on May 23, Patricia Demauro, a New Jersey grandmother, beat those odds at Atlantic City's Borgata Hotel Casino and Spa. Demauro's 154-roll lucky streak, which lasted four hours and 18 minutes, broke the world records for the longest craps roll and the most successive dice rolls without 'sevening out.' According to Stanford University statistics professor Thomas Cover, the chances of that happening are smaller than getting struck by lightning (one in a million), being hit by an errant ball at a baseball game (one in 1.5 million) or winning the lottery (one in 100 million, depending on the game). (Read 'When Gambling Becomes Obsessive.')

So, how did it happen? On Saturday, Denville native Demauro and her friend John Capra decided to indulge their yen to bet. Their Atlantic City jaunt began innocuously enough, with Demauro, only a casual casinogoer, planting herself in front of a penny slot machine on the Borgata floor and Capra going off to try his hand at three-card poker. (See an interview with the new king of poker.)

By 8 p.m., a few hours later, Demauro had grown tired of the slots. She ventured into the poker room to collect her friend, who was losing money. He offered to show her how to play craps. Of the 14 available craps tables, they sidled up to the nearest one and waited for the three other players to finish rolling. Capra shot next, but sevened out quickly. Then, he handed Demauro the dice.

Craps is known as the world's most common dice game and it is played, with varying rules and sizes of table, in virtually every casino on the planet. Craps is a game of chance rather than skill, and with a low house advantage — around 1.4%, which makes it harder to beat than blackjack but easier than roulette — even novices can win. That is, if they're lucky.

According to the casino, Demauro started her roll at 8:13 p.m. She bought into the game with $100 and when the orange-colored dice came around to her, she rubbed her hands together and let them fly. Demauro says she had played craps only once before, and being an inexperienced better, followed Capra's advice when placing bets.

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A craps turn begins with an initial or 'come out' roll, in which the player tries to establish a 'point number' — that is, when the dice add up to four, five, six, eight, nine or 10. Once that happens, the player must roll the point again before throwing a seven, which is statistically the most likely outcome on a pair of dice. If the player rolls a seven before the point, the turn ends.

As soon as Demauro hit her point number (eight), people started betting. She says the game moved so fast after that, she couldn't really keep up. 'There are all these terms I didn't know,' Demauro says. 'People were yelling out 'Yo.' I said to John, 'What's 'yo?' I think that's an 11.'

The table filled up and a throng of spectators gathered. Demauro rolled double sixes, hard fours, snake eyes, every possible combination of the dice. Some people called out requests and Demauro managed to fulfill them. Players from the nearby blackjack table came over to watch, and then came the casino executives, or as she describes them, 'men in dark suits.' Demauro and her audience knew they would never witness anything like this again. 'There was a woman there, and we happened to catch each other's eyes,' Demauro says, 'She smiled at me, and I smiled and said, 'I don't know how to play the game.'

Although there is no official organization that keeps track of gambling world records, a number of clubs record significant dice rolls. Before Demauro's, the longest craps roll lasted three hours and six minutes — accomplished at a Las Vegas casino in 1989, with 118 rolls. And according to gambling expert and author of Beat the Craps Out of the Casinos, Frank Scoblete, the highest number of successive dice rolls was 147, thrown by a man operating under the pseudonym the 'Captain' in 2005. The average number of dice rolls before sevening out? Eight.

Given the rules of the game, there are any number of ways to achieve 154 consecutive rolls without crapping out, though all of them are highly unlikely. Unlikely but not impossible. Stanford's Cover explains: 'Let's say we have a million gamblers trying a thousand events at any one time. That's a billion different rolls of craps.' Out of a billion different games, the probability of getting an event that special is reduced to one in 1,000. 'It's not out of the realm of possibility,' he says.

Demauro declined to reveal how much money she won, but gambling experts estimate that if she made good bets, her winnings were probably in the hundreds of thousands; expert bets would have put them in the millions. Demauro and Capra spent the rest of their holiday weekend in Atlantic City, and even returned to the same craps table two nights later — but only as spectators. 'The expectations were too high,' she says. 'I wasn't ready to be the shooter again.'

Once the shock of her good fortune wears off, however, she says she'll try throwing the dice again. After all, sometimes lightning strikes twice.

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.

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.

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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.

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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.