Top 5 Most Legendary Casino Gamblers

This is a very subjective topic. Do we go with who made the most money, who was extremely inventive in how they played the game, or perhaps some other attribute that made these top performers stand out? Of course, winning the most money is seen by almost everyone as the ‘aim of the game’, so for the most part we’ll defer to their financial success with gambling.

While all gambling is a combination of luck and skill, our top five cannot be considered the luckiest gamblers in the world, but rather the most skillful. For them, gambling is often their primary or only occupation, not considered mere entertainment, but using their wits and experience to win, win often and win big. Gambling is their business, and they mean business!

There are millions of gamblers, possibly tens of thousands of professional gamblers, but only five make it right at the top.

1. Bill Benter

Arguably the most successful gambler on the planet, Bill Benter has achieved spectacular success, becoming a billionaire playing blackjack and betting on horse races.

Benter had an exceptional knowledge of physics and mathematics which he applied to blackjack and horse race betting. He holds a degree in physics from the University of Pennsylvania. To earn some quick money, Benter tried his luck on the Las Vegas strip. His invincible card-counting skills quickly got him banned from blackjack tables at all the major casinos.

Deciding to move to Hong Kong, Benter teamed up with Alan Woods, another mathematician and gambling enthusiast. Together they created an analytical software program that could determine the odds on various horses and races. The unique software was a huge hit that earned Benter and Woods a small fortune. Benter went on to improve the software program and receives an additional $1 million every year. It’s nice to know that he is a generous philanthropist who donates to various charities in the US and Hong Kong.

2. Edward Thorp

Known by some as the “Father of Card Counting,” Edward Thorp made most of his fortune ($800 million) at the blackjack and baccarat tables. Interestingly, just like Benter, Thorp is also a mathematician.

Thorp started his career as a math professor at several well-known universities. He collaborated with Claude Shannon to build the first wearable computer to predict roulette spins in the 60s, offering a +44% accuracy rate on testing. About the size of a cigarette pack, the device involved a number of people wearing them and timing the speed of the roulette wheel’s rotation. It was all very complicated and finally failed when a minor hardware problem rendered it unsustainable.

Alongside his academic career, Edward Thorp also was a master at the blackjack and baccarat tables. Thanks to his immense mathematical knowledge, Thorp developed a theory of counting cards. Later, he went on to apply his theory to predict stock market movements. After using his fortune to invest in the stock market, Thorp’s net worth is estimated to be $800 million.

Thorp explicated his famous theory in his books – Beat the Dealer and Beat the Market (the latter became New York Times bestseller). His name has also been entered into the Blackjack Hall of Fame.

3. Andrew Black

A London-based entrepreneur, Andrew Black is also one of the chosen few who made a fortune from gambling, both by actual gambling and also by devising computer algorithms to predict betting outcomes. Black excelled at math in college; however, he dropped out of academia and took up a few jobs. At one stage he had to stop working to take care of his ailing brother. After his brother’s death, Black began working in a derivatives business, but also began to spend a lot of time gambling. When his gambling winnings exceeded his salary, he quit his job to pursue gambling full-time.

Black then got married and realized an inconsistent income from gambling was not sustainable, so he started a software company. Around the same time, Black met Edward Wray during a game of bridge. Black was working on an algorithm to predict the outcomes of horse races. Wray saw great promise in Black’s prototype and invested in his project. A few years later, Black and Wray founded Betfair, one of the biggest betting sites in the market today. Due to the company’s success, Black’s net worth is estimated to be around $670 million.

4. Zeljko Ranogajec

Zeljko Ranogajec, a.k.a. “The Joker” in the gambling fraternity, has managed to win an impressive fortune from different gambling games, including keno, blackjack, sports betting, and horse race betting, notably holding the record for the biggest win in keno, which was around $7.5 million at a New South Wales casino.

While working as a casino employee, Ranogajec learned the art of counting cards at the blackjack table. In fact, this Australian pro gambler was so skilled that all of the major casinos in Australia and Las Vegas have banned him from their blackjack tables.

In spite of his ban, Zeljko Ranogajec was inducted into the Blackjack Hall of Fame in 2001. Not being able to play, Ranogajec was later involved in multiple gambling enterprises for a time. His net worth is estimated to be around $429 million.

5. Billy Walters

Bill Walters is regarded as one of the most successful bettors in the world. He’s considered a legend in Las Vegas and has maintained an impressive winning streak spanning three decades, with a net worth of about $200 million.

Before his betting career took off, Walters made a living as a car salesman and opened up a his own car dealership business. Around this time, he became involved in sports betting.

After running afoul of the law in Kentucky as a bookmaker, Walters moved to Las Vegas with his wife. In the 1980s, he joined the Computer Group, which utilized computer analysis to determine the outcomes of sports events. Betting on sporting events is risky, complicated, and unpredictable. But it seems like Billy had found the magic key to success that helped make him a millionaire.

Billy Walters mostly placed bets on basketball, the NFL, and college football. placing wagers worth $3.5 million at a go. However, in 2017, Walters was found guilty of insider trading and served five years in prison. In 2020, former President Donald Trump pardoned him.

6. Bonus Outsider

Talking of former president… Richard Nixon. Yes, THE Richard Nixon! The former President of the USA happened to be a very talented poker player. Growing up in a strictly religious Quaker home, Nixon had no experience of card games or gambling, until he was sent from Guadalcanal Airbase to much less hazardous Green Island in the Solomon Islands as a US Navy lieutenant during WW2. He learned and got hooked on poker, and was so good at it that he brought home thousands of dollars in winnings.

This was significant as this money greatly helped fund his first run for political office, winning a California congressional seat in 1946. Now, if being a good poker player got one’s foot in the door and onto a pathway leading to the White House, perhaps Nixon deserves a mention as a gambling success story!