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40 Biggest Historical & Celebrity Gamblers

40 Most Famous Gamblers of All Time: Historical Figures and Celebrities Who Loved to Gamble

Gambling is as old as civilisation itself, and for the lucky few (now famous gamblers), it has proved to be more than a lucrative pastime and more of a bona fide occupation. The gambling history teaches us that famous gamblers were anyone from expert mathematicians and kings to composers and farmers, rising to gamble fame solely due to their wit, talent and, well, luck.

In honour of these daring tricksters and talented players, we've taken a look back through the ages and put together a list of 40 most famous gamblers of all time.

Bear with us for the names you may or may have not yet heard of:

Emperor Claudius

Despite Romans' notorious (or famous) reputation for being big on gambling, there was hardly anyone who enjoyed gambling as much as Emperor Claudius. History says he did not concern himself much with the state, so he spent most of his time drinking and excessively gambling. Some records say his love for gambling verged with obsession, as he even had a specifically furnished carriage with a topple-proof board that would allow him to gamble on the go.

Emperor Claudius was the most famous gambler of the time and the man of the hour who organised all types of games, from gladiatorial fights to chariot races. Claudius not only organised the games but attended them dearly. His most significant gambling legacy is the book he wrote on Roman games and dice!

King Henry the VIII

Often referred to as "England's Number 1 Gambler," King Henry VIII was known for enjoying dice, Table (a version of Backgammon), and Betting Queek (a checkers-related game).

When Henry VIII came to the throne, the streets of London were bursting with a then-new three-card game called "Bragg" which many believe poker was derived from. Henry loved it, together with Fox & Geese: a game of pursuit and Greek: a checkers based game, both of which were super popular at the time.

A famous gambler in his own right, King Henry VIII used to gamble both for fun and money; at one point, he accumulated a total loss of £3,250 which was an enormous sum at the time. But, that wasn't the most surprising risk The King took: playing dice, Henry bet and lost the Jesus bells of the old St. Paul Church! He lost them over a single toss of the dice, making this loss one of the most significant in the history of gambling. Sir Miles Partridge who won the bells, was soon convicted of treason by Henry and hung at Tower Hill for everyone to see.

The King of England was also known to widely ban gambling, except for himself; he also worked closely with London bookmakers whom he never prosecuted for gambling as they enabled him to place bets. To this day, King Henry VIII holds a spot in the Hall of Fame of famous gamblers, despite his infamous losses.

King Charles II

Another king makes for one of the most famous gamblers in history. This was King Charles II, the king who re-established English monarchy in 1660. As a matter of fact, Charles II even wrote a book about his gambles, although one that focuses on both his political movements and gambling games. However, to depict King Charles as a gambler in any negative context would be plainly wrong.

What made King Charles II a gambler was his aptitude for knowing how to avoid risk and manoeuvre his enemies. He did enjoy playing cards but didn't lose anything playing. The biggest gamble of his life was seeking an alliance with Louis XIV after the French conquest. Unfortunately, this alliance proved to be a fatal gamble as it ruined Charles's political credibility at home.

The majority of his Protestant subjects saw Louis as a threat to the religion of Protestant Europe, so he spent the rest of his reign trying to limit this damage.

King Louis XIV

King Louis XIV, also known as the Sun King or Louis the Great, was an admirer of a good life that, among other things, included gambling. In fact, gambling is said to have remained one of the greatest pleasures of court life during the reigns of Louis XIV to Louis XVI. Gambling parties were a regular fixture of court life, with the royal family even having their personal gambling items. 

King Louis XIV turned the royal court into an irresistible combination of the employment agency, marriage market, and entertainment, making Paris the capital of aristocratic Europe. Being in court meant enjoying the best opera, theatre, gambling, music, sex and hunting which, at the time, was the most important.

John Montagu

A rather famous gambler and a dedicated one, John Montagu served as the First Lord of the Admiralty and the British Secretary of State. He was known for never leaving the table during a game, not even to get a meal. In fact, he is the sole reason we have sandwiches today! 

During one game, he asked for a snack while he played - a piece of beef between two slices of bread (not to get his fingers greasy), and that's how things went down. As his title was the 4th Earl of Sandwich, his friends used to ask for "the same as Sandwich" when they wanted a snack during a game. Grabbing a snack later just became "a sandwi­ch".  

Wolfgang Amadeus Mozart

Apparently, the dominant fun to entertain yourself with during the mid-18th century was, indeed, gambling – in one form or the other. Although a prolific musician at the time, Wolfgang Amadeus Mozart was one of the top gamblers of the time. He was known for his unwillingness to economise – regardless of what it meant economising on. Mozart was a part of the Viennese aristocracy, most of who shared a gambling addiction. He loved living lavishly and, to maintain a high standard of living, he would often raise stakes and gamble endlessly. Apart from the love for gambling itself, he also gambled to maintain his connections in aristocratic circles and to secure future projects.

Another famous gambler and composer at the time, Gioachino Rossini was even more prominent in his love for gambling than Mozart. He loved gambling so much that he created a casino in his opera house that had ballet performances during intermission.

Giacomo Casanova

Giacomo Casanova was many things, a true renaissance man some would say; his interests spanned from being a writer and violinist to dabbing into professional adventurism, law, mathematics, and business. Still, the two constants of his life, ones he preferred the most were women and gambling.

Unlike other famous gamblers of his time, Casanova had professional gambling training in his teens, mostly by big professional gamblers and cheats who navigated him towards mastering all relevant tricks and curves of gambling. He was proficient in games like faro and piquet early on, and the games helped him earn money quickly when he needed it.

Upon convincing King Louis XV to start the first lottery in France, Giacomo Casanova moved to Paris. He was then in his 30s. The lottery was initially intended to raise money for the Paris military school, but it turned into a very profitable venture that earned them both about 300,000 francs.

René Descartes

An esteemed French scientist, mathematician and philosopher, René Descartes was very much into gambling, too. He was also known as the "The Father of Modern Philosophy".

Interestingly, unlike most top gamblers who just ended up gambling, Descartes was hoping to take it up as a profession. Upon finishing military service and law school in Paris, he started to gamble professionally. However, professional gambling did not really work for him, so he turned to science and philosophy. Go figure! He kept gambling as a hobby though and sure built a reputation of one of the most successful players, thanks to his intellect, calculations, and mathematical skills.

There are no exact records on what games he enjoyed the most, but it is well known that he applied maths to every game he played.

famous gamblers

Michel de Montaigne

A very prominent philosopher of the French Renaissance, Michael de Montaigne, was primarily famous for writing the Essays and is considered the father of Modern Scepticism. Other than his neck for philosophy, he was also known as his love of gambling. In fact, Montaigne was considered a passionate gambler who enjoyed a strong reputation in the French Society of the 16th century.

Claude Monet

Claude Monet, a French painter who lived and worked in the 19th century, turned to gambling as a young, struggling artist. Actually, he first managed to earn money by selling his drawings to locals. Soon after, he moved to Paris and became very interested in gambling due to the expensive nature of his painting hobby. Monet mainly played table games at the casinos. The rumour has it that Monet won more than $13,000 in a casino game, which allowed him to quit his job and focus entirely on painting. However, there are no firm data confirming it was so.

Fyodor Dostoyevsky

The father of Russian prose, Fyodor Dostoyevsky, left an incredible literary legacy under his name. Other than enjoying the status of a prominent and respected writer of the time, Dostoyevsky was known as a top gambler in certain circles. In fact, his novel "The Gambler" is based on his personal experience! Some historians say that Dostoyevsky used his risk-taking personality and gambling addiction as inspiration for his novels. The legend has it that the last section of "Crime and Punishment" was written in a rush and before the anticipated deadline, as Mr Fyodor had a gambling debt to pay off. There are no firm records to confirm this, though.

Gerolamo Cardano

Gerolamo Cardano was an Italian Renaissance physician, mathematician, astrologer and gambler. He wrote over 200 works on medicine, physics, mathematics, religion, philosophy, and music. But, Cardano may in fact be best known for his gambling which led him to formulate elementary rules in probability. He used throwing dice to understand the basic concepts of probability.

His book, Liber de ludo aleae ("Book on Games of Chance"), examines the first systematic treatment of probability. It was written around 1564, and published in 1663, making him one of the founders of probability theory. The book contains a section on effective cheating methods.

John "Doc" Holliday

John "Doc" Holliday was one of the famous, successful gamblers from the American Old West. Although a dentist and a gunfighter by primary profession, Doc loved gambling and was known in the gambling circles. His friendship with Wyatt Earp and his participation in the famed Gunfight at the OK Corral also contribute a lot to his image.

His intelligence made him a "natural" at gambling which ultimately became his means of support. Holliday soon moved from being just an active gambling participant to being a poker and Faro dealer. Historians describe him as a "dentist whose necessity had made a gambler", and an incredible gambling talent.

Speaking of the Old West, we should mention the lesser known history of ladies who enjoyed gambling. One of them, a woman that went by the name of Lottie Deno, even hung out with Holliday, possibly joining him for a game of poker. Read more about these fascinating women in our piece about famous female gamblers.

Edward Thorp

Edward Thorp is, among other things, an American author, mathematics professor, hedge fund manager, and blackjack researcher. He is best known for developing a programme for calculating probability in Blackjack. Thorp's understanding of probability paid off to him in more ways than one; due to his phenomenal skill of calculating probability, Thorp is considered one of the most successful living hedge fund managers, yielding an average 20% return on his investments.

Amarillo Slim

Out of all famous gamblers throughout the history of gambling, most consider Amarillo Slim to be the biggest gambler in the world. Slim started out as a Texas poker player who joined forces with Puggy Pearson and Doyle Brunson; however, he soon got independent and became one of the most successful gamblers around and the most famous pro bettor in the world.

The mainstream media caught Slim's gambling ingenuity not on the poker table but his exploits away from it. He quickly earned considerable fame for making extravagant bets like saying he could beat a racehorse in a 100-yard dash – which he eventually did. Slim was a master bettor who wasn't afraid to raise bets on all sorts of things, from beating table tennis pro with Coke bottles or a pool champion using a broom handle. Even celebrity gamblers agree that the gambling community won't probably see one like Slim ever again.

Puggy Pearson

Famous gamblers knew him as "Puggy", but his real name was Walter Clyde Pearson. He was known as a cigar-chewing poker legend who wasn't afraid to challenge anyone as an opponent. In fact, he owned "Rovin' Gambler," a 38-foot diesel Imperial Holiday Rambler motorhome, worth $200,000, painted with a dare: "I'll play any man from any land any game that he can name for any amount that I can count.", with the small font under it, reading "providing I like it.".

Puggy was a member of the Poker Hall of Fame, the 1973 World Series of Poker champion and a member of the gambling community who played in Las Vegas' highest-stakes poker games over 25 years. A true high roller, Puggy was admired by his peers and feared by Vegas gamblers and biggest gamblers in the industry.

Pearson is attributed for introducing Las Vegas to the "freeze-out" style. This style is specific for the following:

  • It is intended for tournament poker
  • All players start with the same amount of chips
  • Gradual player elimination throughout the game results in the winner winding up with all the chips

The "freeze-out" style/format has been included into all major poker tournaments as well as the World Series of Poker.

Historians consider Puggy's contribution to poker colossal as he is believed to have turned poker into a respectful form of gambling.

Amarillo Slim

Bill Benter

One of the most famous names in professional gambling, Bill Benter built a name for himself both inside and outside of the gambling industry. Benter began his career with a physics degree which later led him to software development used to analyse horse racing data. The software turned out to be such a success that Benter won close to $1 billion. For things to be even better, he donated most of that money charity.

Bill Benter is also credited for his contribution in creating the world's first software-assisted gambling. Other than that, he was known to use his knowledge in math and physics to count the cards at the blackjack tables. 

If you thought gamblers don't influence other gamblers, you were mistaken; Edward Thorp's book helped Benter perfect his method of counting cards and occupy the position of one of the famous Vegas gamblers. After beating the casino for 7 years straight, Benter was banned from the most famous Las Vegas Casinos which inspired him to move to Hong Kong.

Today, Bill Benter is rumoured to make around $100 million annually. He has remained a donor to the charity and is known as a big-hearted philanthropist.

Alvin Clarence Thomas - Titanic Thompson

More of a hustler, less of a gambler, Titanic Thompson usually struck bets that he expected to win. His real name was Alvin Clarence Thomas, and he got among successful gamblers by winning all kinds of different proposition bets. As mentioned, most of them were devised by him, but there were others he was challenged into doing – and still won.

When Thompson had sufficiently honed his skills, he became a travelling hustler and a "road gambler", gambling (and winning!) his way from location to location.

Minnesota Fats, a celebrated pool player who was included in "the hustling game" by Thompson's partners, considered Titanic a real mastermind, "the greatest action man of all time".

Thompson's one and biggest weakness by his own admission was betting on horses, i.e. horse racing. Titanic lost millions of dollars in failed horse bets throughout his life.

Why the nickname, though? In his own words, Thomson talked about his nickname in a story published in Sports Illustrated in 1972 which he co-authored.

He said: "In the spring of 1912, I went to Joplin, Missouri, just about the time the Titanic liner hit an iceberg and sank with more than 1,500 people on board. I was in a pool room there and beat a fellow named Snow Clark out of $500. To give him a chance to get even, I bet $200 I could jump across his pool table without touching it. If you think that's easy, try it. But I could jump farther than a herd of bullfrogs in those days. I put down an old mattress on the other side of the table. Then I took a run and dived headfirst across the pool table. While I was counting my money, somebody asked Clark what my name was. "It must be Titanic," said Clark. "He sinks everybody." so I was Titanic from then on."

Billy Walters

Billy Waters is possibly one of the most successful gamblers of our time and, surely, the name that deserves its spot among the most famous gamblers ever.

Virtually unheard of but Billy Waters had a winning streak in Las Vegas that lasted over three decades! He is widely regarded as one of the most successful sports bettors in Las Vegas, and in the world.

Today, Walters is a retired gambler but remains an entrepreneur and a philanthropist. His net worth is $100 million.

Phil Hellmuth

Phil Hellmuth, a thorn in the side of many a poker player around the globe, is known for being among the best gamblers of all time. He currently has 15 World Series of Poker bracelets and holds the record for having the most cash finishes at the WSOP, too (a hundred and counting). His nickname is "the Poker Brat" as a result of his often-arrogant attitude towards other players and an over-competitive personality.

Encouraged by his father, Hellmuth started gambling upon enrolling at the University of Wisconsin. Showing a neck for gambling from the get-go, Hellmuth beat everyone from his classmates in the student union to doctors, business people, and all other wealthy players who would play him. Once he realised he could make a living out of gambling, he dropped out of college and left for Las Vegas. Today, he is among the biggest Vegas gamblers to have ever played.

Phil Hellmuth has written over ten books on gambling, has his own Poker Brat clothing line, and is known to give money to charity regularly. "I've always given a lot of money to charity personally, and for me, it's part of a well-spent life."

John Daly

Sport and gambling (i.e. betting) often end up mixing and matching; most sportspeople try gambling at least once in their life but rare are those who turn it into an additional career.

A renowned golfer John' Wild Thing' Daly is a two-times Major winner who never shied away from controversy. It is estimated that this Wild Thing had wildly lost a net $55m on gambling.

Described by many as "larger than life character", Daly would habitually take up all spots on a blackjack table, always playing 7 hands and betting $15,000 on each. Other than sports betting, Wild Thing was also known for indulging in high-stake slots that cost him, no more, no less, than $5,000 per pull.

At an occasion, Daly admitted it wasn't before he took a look through his tax records that he realised the extent of his losses. Still, in true Wild Thing style, he said he had "a lotta fun" and doesn't regret anything.

Nick Dandolos - Nick the Greek

Although born to money, Nick the Greek became famous for his legendary gambling career. At only 18, he moved from Greece to the United States where he, soon after, got into horse betting in Chicago. Early in his gambling career, he won over $500,000, but he almost immediately lost it all shooting dice and playing cards.

In his declining years, Nick was almost broke. Still, Nick the Greek was one of the first members of the Poker Hall of Fame. It is estimated he won and lost over $500 million throughout his life.

Phil Ivey

With an impressive 10 World Poker Series bracelet awards under his belt, Phil Ivey is the youngest player in history to have won his 10 bracelets by the age of 38.

Known as 'the Tiger Woods of poker', Ivey has been admitted into the prestigious poker hall of fame. With a net worth of over $23 million, he held the status of the biggest online cash winner ever – well, at least until 2011. By just playing online poker, Ivey won around $20 million, which put him right among the biggest gamblers in the world.

However, not all information about Phil Ivey render fully clear. Namely, gambling at Crockfords Casino in London back in 2011, he won around $12 million by playing punto banco. The casino refused to pay him and accused him of cheating, i.e. playing his partner using a trick. He was found guilty by the court as well. Still, there is no sufficient available information to explore this situation further.

Brian Molony

Brian Molony is one of those famous professional gamblers who are more infamous than they are famous.

He is a compulsive gambler, and it is not rare that he makes headlines for his gambling ways. To indulge his love for gambling and, consequently, fund his regular trips to the casinos in Atlantic City, Molony embezzled over $10 million from his employers at the Canadian Imperial Bank of Commerce. He was arrested in April 1982 when his theft was uncovered which came as another brutal hit for the man; namely, just a day before going to jail, Molony had lost around $1 million at Caesars Casino. He spent two and a half years in prison.

Molony's story was the basis for the movie Owning Mahowny while a book "Stung" was written and published based on his life.

Phil Hellmuth

Lawrence Revere

Lawrence Revere had a degree in mathematics from the University of Nebraska, was a casino pit boss, professional blackjack player and a celebrated author who got famous for his book Playing Blackjack as a Business. Revere had multiple aliases, including Paul Mann and Leonard "Speck" Parsons.

Developed with Julian Braun, Revere's promoted card counting strategies detailed in Playing Blackjack as a Business:

  • The Revere Point Count
  • The Revere Five Count Strategy
  • The Reverse Plus-Minus Strategy
  • The Ten Count Strategy

Revere Point Count is still considered a benchmark strategy.

Playing Blackjack as a Busines only gave the single-deck version while Revere sold the multi-deck version that is, to this day, sold at large. This professional blackjack player turned author also sold high-level strategies referred to as Revere Advanced Point Count (RAPC.) These days, they are not as popular due to their unnecessary complexity – although they are still valid and in use today.

As he worked both sides of the game at once (casino and player), Revere was considered a controversial figure and a master of avoiding detection by casinos. He trained many of the early counters, some of whom use his strategies to this day.

Mike A. Caro

Mike A. Caro is an American professional poker player and casino executive, pioneer poker theorist, and author of poker books. To this day, he acts as a consultant to many casinos, providing odds.

In 1978, Caro contributed 50 statistical tables to Doyle Brunson's Super/System and wrote that book's chapter on draw poker. He helped develop Poker Probe, the first commercial PC program for analyzing poker situations.

Mike A. Caro is the founder of the world's first permanent poker school, Mike Caro University of Poker, Gaming and Life Strategy. He was an early predictor that real money online poker would work.

Caro is the author of a number of books about poker, most of which Caro made video versions of. The famous poker tells "Weak means Strong" and "Strong means Weak" was coined by none other than Caro. The saying means that players will try to fool other players by acting the opposite way of their true poker hand.

In 1984 at the World Series of Poker Caro demonstrated Orac (Caro backwards), the world's first serious attempt at an AI poker player, a poker-playing computer program that he had written. Orac was a success and most poker professionals were surprised at how well it played.

James Butler Hickok - Wild Bill Hickok

James Butler Hickok, a participant in the US Civil War and a big fan of settling disputes with a duel, became synonymous with the wild west which got him a nickname "Wild Bill".

Wild Bill was big on a gamble, making poker his game of choice. Being a war hero, he made a lot of enemies. This is why his poker games were always lined with a request to sit with his back to the wall throughout the game. That way, he could keep safe and keep his eye out for potential enemies. Unfortunately, the man died from what he had anticipated would be his death – a shot in the back.

In a game that was too good to miss out on, Hickok didn't have a wall to sit against. Instead, he had his back turned to the entrance of Nuttal & Mann's Saloon No. 10 – his favourite saloon in town, and a place where the game was held. During the game, Jack McCall, a local vigilante, and a man who had been offended by Wild Bill the day before shot him at point-blank range in the back of the head. Hickok died on the spot. He fell on the floor in the middle of the hand that had an ace and an eight. Since then, this pair of cards has become known as "the dead man's hand".

In 1979, 103 years after his passing, James Hickok was inducted into the poker hall of fame. He was recently brought back to life in an HBO's suitably named show, Deadwood by Keith Carradine.

Kerry Packer

The King of Whales and an Australian media magnate, Kerry Packer carried this nickname for a reason. In gambling circles, he was known as one of those top gamblers with an easy hand who would routinely bet $450,000 on Blackjack and leave a seven-figure tip to waitresses and hosts of the casinos he visited.

Casino legends say that he once wagered nearly $25 million across four roulette tables and lost it. However, there is no sufficient information to confirm this.

Chris Moneymaker

Chris Moneymaker won the Main Event in the World Series of Poker in 2003, and, in doing so, positioned himself among the most famous gamblers of the world.

He won his entry into the WSOP on the internet, which resulted in a massive inflow of players to online poker sites for the period of the so-called "poker boom." Chris Moneymaker's autobiography, Moneymaker: How an Amateur Poker Player Turned $40 into $2.5 Million at the World Series of Poker says it all actually, so – if you'd rather read about the man first-hand, read it.

Moneymaker is still an active poker player who enjoys gambling and, well, makes money. To this day, he has won over $3.5 million in his career.

Don Johnson

No, not the actor – although the two are often confused. Don Johnson from our list is a businessman and gambler who became one of the most successful gamblers around by winning over $15 million playing Blackjack. He is known for not counting cards and playing fair, but still thinking like a smart player.

In 2011 and 2012, he ran against the three Atlantic City casinos and made gambling history. Johnson insisted on blackjack rules that gave the house an insignificant edge of only 0.26%. Following, negotiated a loss rebate deal that turned a casino's edge into the player's. A move of such type is called a "positive expectation bet."

Johnson's success in the casino world is admirable, and he enjoys status among celebrity gamblers.

The MIT Blackjack Team

You probably know this story by now – a group of students from MIT counted cards and took casinos for millions. The MIT Blackjack Team has been winning money from the casinos since 1979.

The MIT Blackjack Team is known to use:

  • Traditional card counting techniques
  • Shuffle tracking techniques
  • Ace tracking techniques

They are believed to have an edge over the casino in the 2% to 4% range.

Doyle Brunson

Known as Texas Dolly, Doyle Brunson's legacy in the poker world is legendary. Although now retired (he retired in 2018), Brunson is a well-respected individual in the gambling world, not only for his wins but for his manner of playing. Texas Dolly is a member of a club that only includes four people which says enough about his status. 

Doyle is a two-times winner of the World Series of Poker and the author of multiple poker books. His most famous book is Super/System. Like Phil Ivey, Brunson has a total of 10 WSOP bracelets.

James Butler Hickok - Wild Bill Hickok

Stanford Wong

If you are looking for a fantastic book that'll teach you how to get an edge at Blackjack, go for Won's tome, Professional Blackjack. Being a well-known and respected gambling expert, Wong has turned his last name into a verb in the advantage play community. "Wong" is a technique of counting cards as an observer, without placing a bet. You place a bet only you have an edge over the casino due to the count. 

But, guess what? Wong's name isn't really… Wong. It's John Ferguson, but he uses Wong as a pseudonym to stay ahead of casino security.

Richard Nixon

Although thought of as a highly flawed individual by many, Richard Nixon sure deserves a spot among the most successful gamblers. Believe it or not, Nixon used his poker winnings to fund his political campaigns which, supposedly, secured him votes in the gambling community. Jokes!

Nixon never won the World Series of Poker or any major poker tournaments, but did keep his habit of gambling alive and thriving for years. 

Terrance Watanabe

A former millionaire but an apparently unlucky bloke, Terrance Watanabe now holds the record of having the biggest losing streak in Las Vegas history. In 2009 alone, this poor chap lost nearly $127 million at the tables and is now involved in a legal battle with Harrah's over $14.7 million that, allegedly, had loaned him this sum. 

Watanabe claims he spent most of his time at the casino intoxicated as that the casino made sure to keep him in an inebriated state while playing there. He says he was even given pain medication by the casino to encourage him to carry on gambling.

Archie Karas

An American of Greek origin, Archie Karas, is one of the biggest casino legends of all times. His popularity primarily stems from him winning and losing vast amounts of money. Karas earned more than $40 million from 1992 to 1995, making the longest winning streak in history with only $50 wager. After 1995, Karas went on a losing streak but remained a popular and well-respected player in the community.

Akio Kashiwagi

Akio Kashiwagi was a real estate investor and a top gambler based in Tokyo whose love for gamble took him across the Pacific Ocean quite regularly.

Kashiwagi would frequently sit on a plane and go to Las Vegas and Atlantic City with the idea of spending gigantic amounts of money at local casinos. Unfortunately for Kashiwagi, in 1990, he left Donald Trump's casino with a $10 million loss.

Alan Woods

A supreme mathematician and an exceptional gambler, Alan Woods is often described as the godfather of horse racing software. In fact, alongside Bill Benter, he co-created one of the most effective software-assisted horse racing tools. 

Alan's gambling career started with counting cards in Blackjack. He then moved to Hong Kong to work on the software with Benter. After the partnership of the two ended, he teamed up with Zeljko Ranogajec in Manila and made millions of dollars from Blackjack and horse racing. Woods, unfortunately, died of appendiceal cancer back in 2018. At the time of his death, his net worth was estimated to over $670 million.

Gonzalo García Pelayo

Gonzalo Garcia-Pelayo is known as the first person to successfully prove casino roulette wheels were biased, and also among the first to exploit the roulette wheel to his advantage successfully. 

After spending months and years on studying the wheel with the help of his son Ivan and his daughter Vanessa, they had officially started playing in 1991, using the knowledge gathered. They quickly accumulated over $700,000, which lead many casinos in the area to ban them from playing. They were even sued by one casino, but Spain's Supreme Court ruled in their favour.

When Gonzalo headed to Las Vegas, he and his family were already recognised as the people that overcame the roulette wheel. Many casinos banned them from playing. But, even so, the Pelayo family accumulated over $2 million before deciding to retire. Gonzalo's wheel reading led many casinos to fix the mistakes potentially influencing the way the roulette wheel spins.

Gonzalo ultimately wrote a book "The Fabulous Story of The Pelayos" detailing the family's triumph over the roulette wheel. The Pelayo family was also the inspiration for Breaking Vegas: The roulette assault documentary that played on The History Channel.

Gonzalo García Pelayo

Zeljko Ranogajec

Zeljko Ranogajec is one of the biggest gamblers in the world. He is known to spend $1 billion every year on various gambling activities, his favourite being sports betting. Ranogajec is currently estimated at a net worth of more than $900 million.

Zeljko Ranogajec was introduced to the world of gambling early on. He studied at the University of Tasmania and the University of New South Wales only to later drop out and focus on his gambling career entirely. One of the things that makes Zeljko one of the biggest gamblers in the world is his photographic memory which is giving him a significant advantage in card counting. That didn't last long, however, so he moved to Horse racing instead with Alan Woods. The two made millions together.

Final Thoughts

High rollers and gamblers overall are born risk-takers, a specific group of people who see things a bit differently than the rest (of us). Pairing business shrewdness and gamblers' intuition, you get these mythical creatures who wander around casinos, typically drawing attention to themselves only when they win… or go bust. Even so, we love hearing stories of the most successful gamblers in the world and exploring their approaches to various types of casino games! There's something about this group we can't get enough of. Hope you loved our 40 picks!

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