Top 10 Most Reputable Historical Gamblers


Historically, gamblers haven’t all been deadbeats, outlaws, criminals and derelicts nor are they today. In this day and age, more and more people of all walks of life are gambling as both a form of entertainment and as a way to make fast, easy cash. From celebrities playing Texas hold’em to business men playing the stock market, gambling is more popularized in its many forms than ever before, and can now be seen 24 hours, 7 days a week on the Poker Network, for example. But this isn’t an article about gamblers today, but about notable, reputable gamblers of yesteryear. Gamblers who have made a name in the history books, gamblers who in their time and place in society were considered important members of their communities and were well-known for a great deal more than just for gambling. Of those, here are the top ten:

10. John Montague



John Montague lived in England lived from 1718 to 1792. He was a British statesman who held many important and prestigious stations in both military and political offices. Montague doesn’t have the best reputation, but it is said that most of the history written about him was written by his political enemies.

Apparently Montague, the 4th Earl of Sandwich, would ask his servants to bring him slices of meat between two slices of bread during his long hours at the card table. This habit became well known amongst his gambling friends and thus the ‘sandwich’ was born.

Montague was well educated, a Cambridge graduate, and held a number of important posts in his life; however, it is the invention of the sandwich that earns him a spot on this list. (Hogarth’s “Gaming House” painting from, read ‘Hunger and Aces Make Culinary History‘ for more history of the sandwich.)

9. John Aspinall


John Aspinall was in the Marines and was schooled at Oxford. It was there that Aspinall began to grow interested in gambling. In fact, he enjoyed it so much that he missed his finals to attend the races at Ascot and put his entire term’s grant on the nose of a winner at short odds.

He bought Howler, a dilapidated 18th century country mansion near Canterbury, with his winnings in 1956. The estate had 9 acres of gardens and parkland that was to become his first zoo. Funds from his own gambling and the casino business allowed him to build up a private collection that included rhinos, bongo antelopes, Kowalski’s horses and leopards. Here he developed his philosophy of treating animals with respect. He gathered about himself a devoted team of like-minded keepers and even sold some of his jewelry and other possessions in a time of financial duress to pay to feed his animals. Although perhaps not specifically being remembered as a reputable member of society in the military or in politics, Aspinall’s reputability came in the form of his love and advocacy for animals that went down in history.

8. Michael de Montaigne


Another well-known person from history who was a gambler was also one of the most influential writers of the French Renaissance, Michael de Montaigne. He lived between the years 1533-1592 and was considered more of a statesman than an author during the time of his life. He is considered the father of what we call Modern Skepticism today. His influence was far-reaching to philosophers and great writers like Ralph Waldo Emerson, René Descartes, Blaine Pascal, and perhaps even William Shakespeare. Montaigne influenced many by his writing, particularly his book, Essais that contains, to this day, some of the most widely influential essays ever written.

7. Jerome Cardan


The scientist Jerome Cardan who lived from 1501-1576 was an Italian Renaissance mathematician, physician, and gambler. He is best known for his achievements in algebra. He was an accomplished gambler and chess player too. He even wrote a book about games of chance in his book, Liber de ludo aleae (Book on Games of Chance). The book contains the first systematic treatment of probability as well as a section on effective cheating methods. He invented many other things as well: the combination lock, the gimbal, and the Cardan shaft, which is used in vehicles to this day. His other research helped to develop the first high-speed printing press. He also made several contributions to hydrodynamics and he published two encyclopedias of natural science.

6. René Descartes


Another respected scientist and philosopher from the history books who enjoyed gambling was René Descartes who lived from 1596 to 1650. Originally Descartes decided to make a career out of gambling after law school and the military. This career choice didn’t last very long, but he continued to gamble throughout his life.

He has been dubbed the “Father of Modern Philosophy.” Descartes came up with the famous statement, “I think, therefore I am.” Not only a forerunner in philosophy, Descartes is also considered the “Father of Modern Science.” (Image: portrait by Frans Hals.)

5. Charles the II



Charles II restored the English monarchy in 1660. He lived a robust life of gambling and was known as the “merry king.” Games of chance became a focus of life in his court. The love of gambling spread not only throughout England but accompanied the later Colonists to North America (where they found out that the indigenous people had their own games of chance, too). (For more information about Gambling in the North American colonies, read’s “Gambling: Apple-Pie American and Older than the Mayflower.”)

4. Casanova de Seingalt


Today when we think of the name ‘Casanova’ we tend to think of a reckless, wild irresponsible womanizer; however, Casanova was a distinguished man of European society during his time (the 1800s).  Casanova de Seingalt was an avid gambler, as well as a lawyer, adventurer and author. At the age of 21, Casanova set out to become a professional gambler but soon changed to other professions later claiming that he lacked the prudence to “leave off when fortune was adverse, nor sufficient control over myself when I had won” (or, as Kenny Rogers would say, “know when to hold’em, know when to fold’em”).

Casanova played lotteries, faro, basset, piquet, biribi, primero, quinze, and whist among the nobility and the high clergy. He was also very religious, a devout Catholic who believed in prayer. Casanova’s contemporaries thought he was an extraordinary person- he was one of the most prominent people of his time. Prince Charles de Ligne once said that Casanova was the most interesting man he’d ever met saying, “there is nothing in the world of which he is not capable.”

3. Wild Bill Hickok


The nickname implies another reckless character indeed, and in some ways that may be so, but the American Legend Wild Bill Hickok was as respected in his time as ‘wild.’ Hickok had a reputation as an honorable man; he was a war hero, scout and lawman who spent the majority of his life protecting others from crime and injustice.

At the same time, he was an avid gambler and he was a fanatic about gambling, particularly about draw poker. Once he knew he was being duped he’d pull out his Colt and knife and challenge the person by saying, “take the pot.” Tragically, Hickok was killed when he joined a poker game and a group of conspirators who had planned his death had him shot. It is said he developed many enemies when he joined General Jim Lane’s “Red Legs” who were a vigilante group whose purpose was to abolish slavery in the south. He was shot in the back of the head with a .45 caliber revolver and when Hickok toppled backward in his chair and his cards dropped to the floor it included a pair of aces and a pair of eights and became known as the famed ‘Dead Man’s Hand.’

2. Fyodor Dostoevsky



Of all the gamblers to go down in history, Fyodor Dostoevsky has to have been one of the greats. One of the most influential novelists in Russian history, Dostoevsky was an avid gambler who wrote the two famous novels, Crime and Punishment and The Gambler. According to legend, Dostoevsky wrote the last section of Crime and Punishment in a matter of days in order to secure an advance from his publisher in order to settle his gambling debts. He loved games of chance mainly and found great inspiration for his novels and stories from the effects and psychology of addiction and risk that he experienced from his life as a gambler.

1. Claude Monet


Claude Monet’s used his winnings to quit his job as a messenger and to focus on painting, becoming the founder of French Impressionism. In 1891 he won about $13,450 in the French lottery and that was the winning ticket not only for Monet, but for the world. Perhaps if Claude Monet had not made that bet long ago, the world would be minus some of the greatest pieces of art ever painted.

by Natalie Jaro

Other Articles you Might Like
Liked it? Take a second to support on Patreon!


  1. The Biggest And Best Gambler of all time by far is none other than Stu “The Kid” Ungar!!!!!!!!!

    if you don’t know, than now you know!

  2. The composer Niccolo Paganini was a notorious gambler and was in so much debt that he had to pawn his famed Guaneri violin to fess up to his debts. Thankfully a wealthy patron and admirer of Paganini donated his violin to him so he could continue with his career

  3. Nice list. But I see a typo XD "and can now be seen 27 hours, 7 days a week on the Poker Network" 27 hours?