If prostitution is the oldest profession, gambling is certainly the oldest hobby—In fact, there have been many famous gamblers through history. Most ancient civilizations show signs of just how far back playing games for money goes. Games of chance played on tiles were discovered dating back from Ancient China while the oldest six-sided die was found in Egypt, proving they liked a punt over there as well.

Here’s a rundown of ten of the most famous gamblers through history (And even a surprising meal we got from them!)

Tiberius Claudius Caesar Augustus Germanicus (Emperor Claudius)

(10 BC – 54 AC)

The Romans were such big fans of betting you can even find scenes of Romans wagering on animal fights carved into ancient pottery.

And no Roman was more into gambling than Emperor Claudius. As the uncle of Caligula, he was decreed emperor by the Praetorian guard after the infamous ruler was assassinated. Even though he was technically in charge, he didn’t really have much to do, so he spent his free time drinking and gambling.

He was so obsessed with it; he even had a carriage specifically outfitted with a topple-proof board so that he could continue playing with his buds on the go.

Emperor Claudius organized and attended all types of games, from chariot races to gladiatorial fights. And he was all for the spectacle. He once set up an almost 20,000 strong mock battle in the harbor at Ostia when a misguided orca got stuck in the bay. The navy was instructed to attack the whale, losing a ship in the process.

Oh, and he literally wrote the book on Roman games and dice—Talk about famous gamblers through history!

John Montagu

(1718 – 1792)

Many hundreds of years later we get to John Montagu, who served as the British Secretary of State and the First Lord of the Admiralty during his lifetime.

He was such a dedicated gambler, that he would rarely leave the table during a game. He’d sit at the table so long, that he would often miss meals. On one occasion he asked for a piece of salt beef between two pieces of toasted bread (so that he wouldn’t get the grease from the meat on his fingers). Did we forget to mention, that John Montagu had a title? He was the 4th Earl of Sandwich.

The Earl’s friends would later ask for “the same as Sandwich” and the snack later got shorted simply to the sandwich. Who knew we had card games and gambling to thank for sandwiches?!

Giacomo Girolamo Casanova de Seingalt

(1725 – 1798)

A true renaissance man: professional adventurer, writer, librarian, law clerk, violinist, mathematician and businessman—You could probably guess, he was also a famous gambler through history. Giacomo Casanova was many things, but the two things that stayed constant throughout his life were womanizing and gambling.

Trained by professional gamblers and cheats during his teen years, he had plenty of ups and downs during his gambling career. Early on he bet on games such as faro and piquet to earn money quickly when he needed it.

In his 30s he moved to Paris, where he convinced King Louis XV to start the first lottery in France. It was designed to raise money for the military school in Paris, but it turned into a very profitable venture for both of them, earning them each about 300,000 francs.

Queen Marie-Antoinette


Staying in France, only a few years later we find the original party girl, Ms. Maria Antonia Josepha Johanna, better known as Queen Marie-Antoinette. The last French Queen was a huge fan of gambling.

At the time, aristocrats were forbidden to engage in trade, so gambling was one of the only honorable ways to make some extra cash. The Queen’s own mother taught her to gamble while still in the Austrian court. And she was good at it.

Marie-Antoinette took part in plenty of extravagant behavior; hunting in the Bois de Boulogne, spending heavily on clothing and sleigh racing, but her favorites pastime was probably playing and wagering on cards.

The Queen hosted nightly games but as her debts started to mount, King Louis XVI decided to put an end to it. She begrudgingly consented, but only on the agreement that she was allowed to play one more game. Being the bad-ass she was, she pushed it as far as she could and allowed the final game to go on for three solid days.

Wolfgang Amadeus Mozart

(1756 – 1791)

As you can see, there clearly wasn’t much to do during the mid-18th century. And almost everyone ended up taking part in gambling in one form or another.

Another intrepid gambler was Mozart. Although a prolific musician at the time, he never did secure a permanent court term. So, in order to maintain a high standard of living, he needed plenty of extra cash.

He also taught music lessons to children and gambled to keep up appearances. This allowed him to move in aristocratic circles and to secure future projects.

Another composer at the time, the Italian Gioachino Rossini took it just one step further and created a casino in his opera house. He even sent the ballet dancers to perform in his casino during intermission.

James Butler Hickok

(1837 – 1876)

Jumping over the pond to the infamous town of Deadwood, South Dakota where murder was rampant and justice sparse. In this bizarre settlement in the mid-1800s you’d find “Wild Bill,” James Butler Hickok, who became synonymous with the wild west.

Born in Illinois, he worked as a lawman in the frontier territories and played his part in the US Civil War, making his name as a gunfighter and a scout.

A big fan of settling disputes with a duel, which he obviously always won, he was also big on a gamble. Poker was his game, but he made a lot of enemies as a war hero, and for this reason he insisted on sitting with his back to the wall when he was playing, so that he could keep his eye open for possible enemies.

On a fateful night in 1876, this position wasn’t possible, but the game was too good to miss out on. So, he took a seat with his back to the entrance at his favorite saloon in town, Nuttal & Mann’s Saloon No. 10 and started playing poker. During the game a local vigilante, Jack McCall, who had been slighted by Hickok the previous day, entered the bar and shot him at point-blank range in the back of the head.

Wild Bill died on the spot, in the middle of the hand, dropping his cards on the floor: an ace and an eight, which since then has become known as “the dead man’s hand”. He was later buried in the same plot as Calamity Jane.

In 1979, James Hickok was inducted into the poker hall of fame, 103 years after his passing. These days you can see him brought back to life by Keith Carradine on HBO’s appropriately named show, Deadwood.

Franklin D. Roosevelt

franklin d roosevelt fireside chats

American President Franklin Delano Roosevelt (1882 – 1945) delivers one of his Fireside Chats in the 1930’s.


FDR will go down in history as one of the most successful presidents in US history. But did you know he was a huge fan of gambling? As with our previous subjects, Franklin D. Roosevelt was a bit fan of Poker. But unlike many others on this list, he was never a big fan of high stakes.


A few times a week he would organize a game with his associates on the second floor White House study. The very room where he would sit to give his famous ‘fireside chats’. In fact, during these talks you can actually hear the clickety-clack of poker chips which he used to sooth himself during the popular radio broadcasts.

His poker table would often be filled with well-known makers and shakers of the day, including a weekly lunch and game with no other than Mark Twain.

One of FDRs best known federal programs, the New Deal, was apparently named after a new hand of poker rather than a new agreement, as many currently believe.

As mentioned before, he may have loved the thrill of the game, but he hated the idea of playing for high stakes. No matter how much his friends and associates pleaded, he refused to up the stakes above an ante of a dime. During a particularly bad run Attorney General Robert Jackson only lost $2.30 over a week.

His favorite games were seven-card stud with one-eyed jacks wild and Woolworth’s (where fives and tens were wild).


Frank Sinatra

frank sinatra famous gambler through history

Frank Sinatra Playing a Game of Cards


This one may come as no surprise to you, but Old Blue Eyes was a huge fan of a casino. A leader of the Rat Pack and the original cast of Ocean’s Eleven, much of his time was spent in the Sin City. He first performed in Las Vegas at the Desert Inn in 1951.

As a cultural icon, he actually helped to create the glitzy image of Las Vegas as a cultural institution, with regular performances at the Sands. From Vegas to Tahoe, he has a go at every table in Nevada.

By 1960 he wanted to his own piece of the pie and started his very own casino, Cal Neva. The casino was on the shores of Lake Tahoe and attracted the likes of Lucille Ball, Joe DiMaggio, Lena Horne and Marilyn Monroe.

On his passing, the lights of the Strip were dimmed as a final tribute.


Charles Bukowski


An American icon, Bukowski’s writing epitomized L.A.’s 1970’s ‘everyman’ more than anyone else of the period.

His work often focused on the risk of gambling, both literally and in life. Books like “Ham on Rye”, Post Office” and “Hollywood” all touched on this topic. He even had a poem called “Gamblers”.

In his own life Bukowski spent a decade as a filling clerk, he then decided to take a chance on life and become a handicapper at the Hollywood Park racetrack. Unlike everyone else on this list, his game of choice was horseracing. Despite what you might assume, Bukowski was incredibly risk adverse. He never placed a bet on a gut feeling, but rather on well researched statistics.

He once said, “If you don’t gamble, you’ll never win”. Bukowski stated that he had no desire for a speech at his funeral other than to say he was “successful on betting on horses”.


Kerry Francis Bullmore Packer


Probably one of the lesser known individuals on our list, but none-the-less one of the most interesting. Kerry Packer encompassed everything it means to be a gambler.

Packer was a successful Australian media mogul, best known for establishing the World Series Cricket. There are countless stories of his crazy antics.

One of the best-known stories includes a toss of coin. While playing at the Stratosphere Casino, Packer was approached by a Texan oil tycoon who tried to get him to play a game of poker.

When he refused the Texan stated, “I’m worth $60 million!”, Packer quipped back, “head or tails?” suggesting a $120 million dollar wager. The Texan realized he’d more than met his match and politely backed down.

Other stories have him losing $28 million over a week in London (the biggest recorded loss in English history) and getting a payout of $33 million during one night at the MGN in Vegas.


These are some of the famous gamblers through history who made the cut, but many more could have been included. It just goes to show that some of the greatest minds, richly-talented souls and most influential people in history were as partial to a flutter as the rest of us.

Arthur Crowson

Arthur Crowson writes for GambleOnline.co about the gambling industry. His experience ranges from crypto and technology to sports, casinos, and poker. He went to Douglas College and started his journalism career at the Merritt Herald as a general beat reporter covering news, sports and community. Arthur lives in Hawaii and is passionate about writing, editing, and photography.

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