Famous Figures from History Who Were Also Gamblers

15th Apr 2020, 11:13:45 PM

Gambling, in some form or other, has been around for almost as long as we humans have. Dice and other artifacts related to gambling from at least 3000 B.C. have been found on archeological digs in the region of Mesopotamia, which is often considered the birthplace of civilisation.

And who can say that early Homo Sapiens weren’t above betting their favourite lump of rock on who would be the one to bring down the woolly mammoth?

Obviously written records don’t date that far back so we’ll never know. But there is plenty of evidence that big money has been changing hands over games of chance for a long, long time.

Here we’ll take a look at some famous historical figures who were also the high rollers of their time

The Ancient Romans


Gambling was so popular in the Roman Empire that the first of our Gamesters, the Emperor Augustus (the first of the Roman Emperors) banned it completely, except for one week of the year, Saturnalia.

That ban didn’t extend to him and his companions though And when he wasn’t busy expanding his empire or enforcing the Pax Romana, he loved nothing more than to roll the bones with his buddies.


Caligula is infamous for his depravity and cruelty. He would torture and execute people at random. He is rumoured to have murdered his own mother and slept with all three of his sisters and was just an all round nasty piece of work.

He was also an inveterate gambler who turned the royal palace into what was basically a massive casino. Worse still, he was a well-known cheat.

So why did people keep playing with him? Well, would you refuse a game of cards with a man who ordered philosophers to be executed with red-hot pokers inserted in their anuses just because he found the subject boring

Caligula - High Rolling Psychopath


His successor, Claudius, was a much more level-headed individual. He improved Roman bureaucracy, built roads, aqueducts and canals all over the empire, and restored Rome's finances after the ravages of Caligula.

He presided at public trials and never tired of issuing new laws and edicts. And if he had to murder a few senators to maintain his position, modern historians are of the opinion he should be forgiven.

But he still found time for his favourite pastime, dice. He even wrote a book about it. “Where did he find the time?”, we hear you ask. Wherever he could, including a portable gaming table in his chariot, according to the historian Suetonius.


Many other emperors were struck with the gambling bug, but we’ll leave you with Nero. Most famous for allegedly playing his fiddle while Rome burned, he is also suspected of setting the fire himself to clear space for a new palace.

What most people don’t know was that he was also an inveterate gambler, willing to bet 400,000 sesterces on a single roll of the dice. We don’t know exactly how much that is in today’s money. But it was certainly enough to be considered extravagant behaviour, even for an Emperor.

The Ruins of Nero’s Palace

Other Gambling Heads-of-State

Louis XVI and Maria-Antoinette

Marie-Antoinette and her husband Louis XVI were famous for their extravagant lifestyles. And gambling addictions. While the common people of France were starving, they lived it up at their luxurious, custom-built Palace of Versaille.

Here they would gambling the nights, and the state finances, away with the nobles of their court. Until the French Revolution that is. This was one couple who literally lost their heads over gambling! 

King Henry VIII

Henry VIII is remembered in the history books mainly for having 6 wives, and creating a whole new church to make this possible. That’s because the Pope refused to grant him a divorce from his first wife, Catherine of Aragon.

Although his behaviour was tyrannical in many ways, he was a very democratic and enthusiastic gambler. He never pulled rank during a game and would play with all-comers, nobility and commoners alike. And there was no shortage of partners!

Despite being the self-proclaimed “Best Gambler in England”, he was actually terrible and nearly always lost. This might be another reason behind the Reformation.

Once the Catholic church was outlawed, Monasteries were disbanded. Their land and considerable wealth seized by the Crown. A good portion of this bounty was used to pay off the king’s massive gambling debts.

King Charles II

Charles II was almost the complete opposite of his predecessor, Henry VIII. Known as the “Merry Monarch” because of his love for wine, women and song, he saw nothing wrong with his subjects having a good time as well. This was something that Henry VIII and the ministers of his newly-established Church of England seriously (to the point of death) disapproved of.

Even though he shared Henry’s passion for a flutter, the resemblance ends there. Charles was a shrewd gambler who knew how to bet the odds. And with 12 illegitimate children to support, he needed those winnings. 

The Merry Monarch - King Charles II

Richard Nixon

There are gambling stories about almost all the American Presidents. George Wahington, the first president of the U.S.A kept a detailed betting journal. In it he recorded his wins and loses. Ever prudent, the journal reveals that he was a cautious gambler who never staked big money, and managed to break even most of the time.

And other presidents from Ulysses S. Grant to FDR were all well-known for their shrewdness at the poker table. This is not surprising really. That’s because being a President is all about taking calculated risks.

But Richard Nixon deserves a special mention because gambling got him into the White House in the first place. A hustler from his teen years, when he ran a carnival Wheel of Fortune, Nixon didn’t just play poker with his army buddies when stationed in the South Pacific.

He actually opened an illicit casino and bar. It was the money he made from this plus his winnings that funded his first Presidential bid. And people were surprised by Watergate, go figure.

Barack Obama

The tradition of Poker playing Presidents has fallen off in recent times. Ford, Carter, Reagan, Bush Sr, Clinton, Bush Jr - not one of them felt the call of the felt.

And then came Obama. Although his media handlers tried to keep it out of the press, Obama had a reputation in Washington and beyond as a shrewd, cool-headed player. And while he never played for very high stakes, his poker playing abilities helped push him into the presidency.

Literary Figures

The world of literature has its fair share of gamblers. In his lifetime, Hemingway was as famous for his passion for “manly” pursuits like huntin’, fishin’, drinkin’, and gamblin’, as he was for his books.

Ian Fleming spent as much time in Casinos as James Bond, his fictional hero. And Dostoyevski, author of the novel “The Gambler” among others, was just that, a gambler.

Roald Dahl

But it may surprise you to know that beloved children’s author Roald Dahl (Charlie and The Chocolate Factory, The Big Friendly Giant, etc)  was also a betting man.

So much so that he taught his children to play blackjack ‘as soon as we could count' according to his daughter Lucy Dahl. He even smuggled her into the Ritz Casino in London when she was only 16 so she could try her luck. They won.

René Desescartes

Descartes was a 16th century mathematician, philosopher and metaphysician who is credited with being the father of modern philosophy. But his first ambition in life was to be a professional gambler.

According to letters he wrote during his youth, his only ambition was to make a living from gambling. Once he had finished his military service and the Law studies his family pushed him into, that is. And he tried, he just wasn’t very good at it. Happily for him, he was very good at Maths and Philosophy and could support himself and his lifelong passion for gambling (badly) from the money his published works made.

And Others


Michelangelo, the painter and sculptor, is a household name thanks to masterpieces like the Sistine Chapel and the Statue of David. But in his time, Michelangelo was a familiar name in the tavernas of Italy thanks to his love of wine, card playing and making wagers of all kinds.

You won’t find much written about this aspect of his character in Art History books. But it has led to claims that he created at least two works of art as the result of bets.

The first is a little-noticed profile carved into the walls of the Palazzo Vecchio in Florence. Local legend has it that Michelangelo carved it with his hands tied behind his back because a friend bet him he couldn’t.

The second is the much more controversial theory that Michelangelo actually painted the Mona Lisa after he lost a drunken card game with Leonardo Da Vinci. And if that’s not enough, it also states the Mona Lisa is really a man in drag!  

Lucien Freud

Although Lucien Freud is not quite the household name that his grandfather, Sigmund, is. But he is still one of Britain's most highly regarded contemporary painters nine years after his death in 2011.

He was also a prodigious gambler. In his book “Breakfast with Lucien” journalist and close friend of the artist describes how a younger Lucien would regularly run up losses in casinos and racetracks around the country.

And, since at the time he was struggling to make a living, he would have to pay off these debts with paintings or special commissions. At other times he borrowed money or sold valuable paintings from his own collection.

At one point he was even banned from all racetracks in the country as a bad debtor. But since his main gambling passion was horse-racing, the artist would wear various outlandish disguises to be able to attend a meet.

Portrait of Lucien Freud – Famous Gambler

Lucien Freud was a self-confessed gambling addict. Strangely enough, when he became successful and his paintings started selling for six figures or more, his gambling addiction evaporated.

Apparently it was the rush of losing more than he could possibly pay rather than winning that kept him coming back for more. Once he could afford to settle his gambling debts immediately, the activity lost its appeal. I wonder what his grandfather would have to say about that!

Tobey Maguire

The young actor is most famous for playing the nerdy Peter Parker in Sam Raimi's Spider-Man trilogy. Peter spends most of his time when not being the heroic Spider-Man, agonizing over how his actions and choices would affect others.

Allegedly, the real Tobey Maguire is nothing like his on screen character. In fact, according to a new book by  Houston Curtis, card cheat-turned-TV producer, he’s the exact opposite. Player X, the sleaze bag in the 2018 film Molly’s Game, was not, as previously believed, an amalgamation of various actors but a portrayal of Tobey.

In the film, Player X took great delight not just in winning by fair means or foul, but also in humiliating his opponents and destroying their lives. And, if Houston Curtis is to be believed,  the fiction is not far from the fact. Which is probably why you haven’t seen Tobey on the big screen for a while, and nor are you likely to in the future.

This list could go on and on but as we don’t have enough space to list all the famous gamblers in history, why don’t you check this out, a list of all the amazing casino games we have available online here at 777slotsbay.com. Enjoy!

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