There are many reasons for gambling, aside from the thrill of potential wins. For some, it’s about the positive experience of playing their favorite online casino games, or the excitement and the pleasure of discovering a new title. For others, it’s the comfort of returning to an old favorite or the relief of switching off the troubles of the outside world and enjoying an hour or two of online fun.

When you gamble for real money, however, you can’t always be a winner. Even the best gambler in the world has had more than a few games that didn’t end the way they wanted it to. After all, a huge part of gambling is luck. No matter how hard you work on your strategy, there is always that one element that can tip the scales. 

However, there are a handful of famous high rollers who have been fortunate enough to have luck on their side. These players of both land-based and online casino games have gone on to become some of the most successful and richest gamblers of their time. Read on to learn about the most successful gamblers of all time.

1. Archie Karas

Archie Karas, born Anargyros Nicholas Karabourniotis in Greece in 1950, is probably the most famous gambler in the world with an unprecedented streak of good luck.

Karas arrived in the U.S. at age 17 and worked in a restaurant in Los Angeles, next door to a bowling alley and pool hall. Soon he became an expert pool player, showing exceptional manual dexterity. So, how did he go from a skilled pool player to one of the best gamblers in history? 

He discovered that he loved winning bets more than playing pool and, looking for new challenges, tried his hand at the card-playing hall on the bowling alley premises. He had a natural ability for playing poker. He was not only good with the cards but had an inborn confidence and bravado. Those who watched him play said that he was a fearless gambler. But as Karas himself put it, one day he could drive a Mercedes, and the next day he’d be forced to sleep in it.

Karas headed for Las Vegas with just $50 in his pocket, convinced an acquaintance to lend him $10,000 at 50% interest, and what followed was the longest winning streak in the history of gambling. It’s since been called “The Run” and involved a combination of luck and exceptional skill. While Karas tried his luck at most of the popular casino table games, he favored poker and razz. By 1995, he had turned his original $50 into $40 million in winnings.

2. Nick Dandolos

Another Greek-American who has made a name for himself among high-roller gambling legends is Nicholaos Andreas Dandolos. Soon after “Nick the Greek” arrived in Chicago around 1902, he decided to become a gambler. Combining a natural ability for playing cards and dice casino games while also studying other players and various techniques, he became a force to be reckoned with at the casino tables. In fact, he won so frequently that card club owners even tried to recruit him as an employee to keep him away from their tables.

Nick, also a fearless gambler, would bet large amounts on the roll of a dice poker game, winning or losing in a single day as much as $100,000 (about $6.5 million in value today). He soon became a legend in Chicago clubs and across the U.S.

At the pinnacle of his career, casino owners set up a showdown between Nick and successful gambler Johnny Moss. The poker contest lasted an incredible five months and paved the way for what would eventually become the World Series of Poker. The players took breaks only to eat and sleep and to keep the audience’s attention; the two men were challenged with variations of the game. Eventually, after losing $4 million, Nick got up from the table and conceded defeat.

3. Phil Hellmuth

Undoubtedly, one of the top gamblers in the world, Phil Hellmuth, nicknamed the “Poker Brat,” has become a household name for poker enthusiasts. While he may be widely known for his aggressive playing style and sometimes questionable casino table etiquette, he is also a poker tournament master and there is no denying that he is one of the best professional gamblers of the modern age. He has won 15 World Series of Poker (WSOP) bracelets, and his successes have led him to author the poker strategy book, “Play Poker Like the Pros.”

If you’re thinking about starting to play the card game or you’re a regular online poker player, his book has some interesting insights into the world of professional poker and will give you an understanding of the game’s fundamentals. Hellmuth has also made poker tutorial videos that you can access online. You’ll see that despite being known as the “poker brat,” he shows an unusual amount of emotion when talking about the game. He says he does this to prevent these emotions from manifesting while he plays.

4. Phil Ivey, Johnny Chan, Doyle Brunson

In joint fourth place on the list are Phil Ivey, Johnny Chan, and Doyle Brunson, having each won 10 WSOP bracelets. Only Hellmuth has more accolades than this.

Phil Ivey

Interestingly, Phil Ivey has not only achieved amazing success in poker — he also won $11 million playing baccarat in 2012. However, he was caught using a technique known as “edge sorting” and was never awarded his winnings. “Edge sorting” is when a gambler decides if a face-down card is likely to be low or high by observing, learning, and exploiting subtle, unintentional differences on the backs of the cards being dealt.

Doyle Brunson

Doyle Brunson was a Texas Hold’em legend who became one of the world’s richest poker players before his retirement in 2018. Before his retirement, he is reported to have earned more than $6.1 million in live poker tournaments. However, he isn’t just known for his poker prowess — he is the author of the book “Super System: A Course in Power Poker,” which, apart from being an extremely interesting read, is widely regarded as one of the best poker strategy books on the market.

Johnny Chan

Another Poker Hall of Fame legend, Chinese-American Johnny Chan, has made more than $10 million dollars in tournaments — a fraction of what he’s earned in cash games and brand endorsements. But Chan is quick to point out that he’s put an enormous amount of work into achieving poker success, including quitting smoking, exercising, eating healthy, and learning to keep his temper under control. This discipline paid off numerous times throughout his career, including when he became the World Series of Poker Main Event Champion in both 1987 and 1988. 

5. Chris Moneymaker

He’s the winner of the Main Event in the World Series of Poker in 2003 — and he’s aptly named Chris Moneymaker. Moneymaker made history by being the first player to win his entry into the WSOP by playing poker online. Interestingly, he entered the 2003 WSOP Main Event through a $39 online satellite, which is said to have led a huge influx of players to online poker sites in what is known as the “poker boom.” Moneymaker has since penned his autobiography, “Moneymaker: How an Amateur Poker Player Turned $40 into $2.5 Million at the World Series of Poker.” Moneymaker continues to rack up winnings today and has won more than $3.5 million throughout his career. 

6. The MIT Blackjack Team

Many names on this list have had impressive successes at the poker table, but gambling encompasses a wide range of casino table games and other games of chance. A list of some of the best gamblers in history wouldn’t be complete without a mention of the impressive yet controversial success of the MIT Blackjack Team. They were a group of students that made a name for themselves counting cards in the 90s and winning millions because of it. 

Despite its controversial nature, the MIT Blackjack Team’s incredible success in card counting is a legendary chapter in the world of gambling. In 1979, a group of MIT students attended a short-term course called “How To Gamble If You Must” to learn about blackjack. This is where they learned about card counting and soon after tried their luck in Atlantic City. 

While their initial attempts didn’t yield much success and led to their disbandment, a chance meeting between one of the original members and another skilled blackjack player rekindled their aspirations, ultimately giving rise to a team that would take full advantage of an Atlantic City regulation prohibiting casinos from banning card counters. Playing mostly on weekends, this team, which remained strong for close to a decade, took the Atlantic City casinos for millions, and their story has been the subject of numerous books and movies. 

Have Fun Playing and Applying Your Strategy at Borgata Online

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