Five Famous Historical Gamblers

Five Famous Historical Gamblers


Nearly everyone likes a flutter, with some famous figures from back in the day being no exception. The Tip Top Fox dusts off the books to bring you five famous historical gamblers

Above image is the 44″x33″ oil painting Party Pooper by artist Michael D’Antuono

While not quite the world’s oldest profession – many would consider that to be prostitution – gambling has rather a long and chequered past. The earliest records, according to David Schwartz’s Roll the Bones: The History of Gambling (2013), date the existence of Chinese gambling houses back to the first millennium BC (around 1,000-1 BC). Playing cards first appeared in China around the 9th Century AD.

Interestingly, modern-day poker can trace its origins back to either a domino-based card game played by a 10th Century Chinese emperor, the 16th Century Persian card game As Nas or the 17th Century French card game Poque, depending on which historian you read.

There have been plenty of famous figures during this long time period who have been partial to a punt. The Tip Top Fox compiled a list of five famous historical gamblers we think you may find interesting:

1. The Earl of Sandwich

John Montagu, the 4th Earl of Sandwich

The sandwich might well be the most popular lunch choice in the Western world today and was popularized in England in 1762 by John Montagu (1718-1792), the 4th Earl of Sandwich.

Legend has it Montagu was an avid gambler and card player who played long sessions at his home and did not like to leave the table even to eat. Instead, he would ask servants to bring him “slices of meat between two pieces of bread” so he could pick it up easily and eat while continuing to play, and not get greasy fingers all over the cards.

Montagu’s card partners and contemporaries soon started asking for “the same as Sandwich” and thus the sandwich was born.

It is likely that Montagu got the idea for his sandwich from European travels in his younger years. In 1737 he spent two years traveling. Montagu visited several European countries including Greece, where mezze platters were common and he certainly could have drawn inspiration.

It is rumoured that after a particularly good night gambling, Montagu – who was also Lord of the Admiralty – decided to fund Captain Cook’s voyage to the Pacific. Cook subsequently discovered Australia and the Sandwich Islands (modern-day Hawaii) – named in Montagu’s honour. 

Though Montagu enjoyed many card games of the times, his favorite was Euchre – a trick-taking card game played with a deck of either 24, 28, or 32 cards – which he played during his time in the Navy. Also known for his great endurance while playing cards, Montagu often playing for over 24-hours straight.

With military decisiveness and a royal bankroll, if Montagu were alive today he would probably be an avid poker fan.

2. Richard Nixon

March 16, 1962, LIFE magazine front cover of Richard Nixon

Many occupants of the White House have been partial to a hand of cards, with Abraham Lincoln, Ulysses Grant, Theodore Roosevelt, Franklin Roosevelt, Lyndon Johnson, Harry Truman and Barack Obama just some of the past US presidents to have had a passion for poker.

It is perhaps the 37th president of the United States, Richard Nixon (1913-1994) – serving from 1969 until 1974 – who is the most well-documented of these however.

More famous for the Watergate scandal than anything else, Nixon showed that the ability to lie well can make for a handy transferable skill between poker and politics.

While Nixon’s most famous quote is probably “Well, I’m not a crook. I’ve earned everything I’ve got.” it didn’t stop the calls for his impeachment. He resigned from the presidency on August 9, 1974. A lot of what Nixon did earn himself prior to his career in politics, however, came from the poker tables, according to Jonathan Aitken’s biography Nixon: A Life (1996).

Poker and Politics

At age 29, Nixon served as a lieutenant in the US Navy in the Pacific during World War 2, stationed at Green Island. It was here he was first introduced to poker by friend James Stewart after watching his fellow officers play five-card stud and draw poker.

Intrigued by the game, Nixon asked Stewart some strategy advice, with the latter telling him to fold around 80 percent of his hands and stay in only when confident of having the best hand. Despite a religious Quaker background that frowns on gambling, Nixon was a quick learner. Aitken credits the future president as winning roughly US$6,800 by the time his service concluded in July 1944. That would be worth just over $100,000 by modern standards.

“He was the finest poker player I have ever played against,” stated friend and fellow Navy officer James Udall in a 1970 LIFE magazine article. “I once saw him bluff a lieutenant commander out of $1,500 with a pair of deuces.”

While Nixon earned his nickname ‘Tricky Dicky’ during his run for the US Senate in 1949 rather than at the card tables, it is Nixon’s skills at poker that first bankrolled him to enter the world of politics. Nixon used his poker winnings to partially finance his run for California congressman in 1946, where he defeated Democratic rival, Jerry Voorhis, to serve from 1947 to 1950. Something to consider for anyone looking to get into politics themselves perhaps? Let us know how you get on.

3. Wild Bill Hickok

James Butler ‘Wild Bill’ Hickok, 1837-1876

You can’t mention famous gamblers throughout history without a visit to the Wild West, a time and place synonymous with poker and the start of the games’ growing popularity.

One of the more famous gunslinging poker players of the time was James Butler Hickok, more commonly known as Wild Bill (1837-1876). Hickok’s moniker stems from the fact he used his father and late brother’s name, William, as an alias during the early part of his career.

Born and raised on a farm in northern Illinois, Hickok lived a colourful life; he served as a soldier and army scout, and worked as a frontiersman, lawman, actor and professional gambler over his 39-years.

A great deal of Hickok’s infamy came from the man himself. In an interview with journalist George Ward Nichols – widely regarded as the creator of Hickok’s legend – Hickok claimed to have killed over 100 men in his gunslinging career, although only seven are actually confirmed.

The majority of these came during his career as a lawman. It was his first confirmed kill that kickstarted his reputation as a gunfighter and gambler.

The Wild West

Shortly after his service in the Union army in July 1865, Hickok was plying his trade as a gambler in Springfield, Missouri. This is where he got into a dispute over unpaid gambling debts with local gambler Davis Tutt. The two faced off in the town square in a quickdraw duel, reported to be the first of its kind, where Hickok shot and killed Tutt. After claiming self-defense, Hickok was subsequently acquitted of murder at a trial by jury on August 3, 1865.

However, It was Hickok’s death in Deadwood, Dakota, in 1876 that truly cemented his legend. This saw him popularised as one of the “heroes of the West” in the dime novels of the late 19th and early 20th centuries.

Hickok’s end came during a poker game at Nuttal & Mann’s Saloon No. 10 at the hands of Jack McCall. A reputation like Hickoks’ did not come without a few enemies and he usually preferred to sit facing the door. However, with the only seat available in the game facing the opposite way Hickok had no choice but to take it. Despite asking twice to switch seats with a fellow player, Hickok was refused.

McCall, who subsequently claimed the murder was in revenge for Hickok’s killing of his brother while working as a lawman in Abilene, had reportedly been beaten at poker by Hickok the previous day. With his back to the door and embroiled in a hand, Hickok failed to notice McCall’s approach. Hickok was shot in the back of the head, dying instantly.

Hickok’s final hand saw the gunfighter holding two pairs, black aces, and eights. This is called the ‘dead man’s hand’ in popular poker parlance as a result.

4. Fyodor Dostoevsky

Portrait of Fyodor Dostoevski by Vasili Perov, painted in 1872

Proving that gambling is not all fun and games is our next entry, and that is Russian intellectual heavyweight Fyodor Dostoevsky (1821-1881). The Moscow-born novelist and journalist is considered one of the greatest psychological novelists in world literature.

With his sizeable catalogue of work translated into over 170 languages, Dostoevsky is widely regarded as having had a profound influence over modern literary criticism, existentialism and Freudianism.

While that may be the case, it’s the man’s vices that interest us for this article. Probably best known for writing Crime and Punishment (1866), it is his 1867 novella The Gambler where Dostoevsky really bares his soul.

The Gambler

Inspired by Dostoevsky’s own real-life gambling addiction, the 191-page novella charts the rise and fall of tutor Alexei Ivanovich. The tutor’s life begins to spiral out of control when introduced to roulette by love interest Polina Alexandrovna.

Based in the fictitious town of Roulettenberg – you can see where this is going – it’s a sordid tale of one mans’ fall into the depths of addiction. The vast majority of characters are in debt and playing each other off for money. It’s a lot more complex than that, exploring the psychological aspects of addiction, obsession, money, and loss. It’s a great read if you can wade your way through it.

While the central theme of the novella is gambling, it is depressingly autobiographical stuff from Dostoevsky. It reflects both his addiction to gambling in the form of roulette and his extramarital affair with the author Apollinara (Polina) Suslova, whom he named the character Polina after.

Writing to his brother Mikhail in September 1863, Dostoevsky talks about losing the value of 35 Napoleons (a gold coin worth around 20 francs back in the late 1800s) at the roulette tables.

“And I believed in my system … within a quarter of an hour I won 600 francs. This whetted my appetite. Suddenly I started to lose, couldn’t control myself and lost everything. After that I … took my last money, and went to play … I was carried away by this unusual good fortune and I risked all 35 napoleons and lost them all. I had 6 Napoleons d’or left to pay the landlady and for the journey. In Geneva I pawned my watch.”

Malcolm Jones, Introduction to Notes from the Underground and The Gambler (1991), Oxford University Press.

It was roughly 1 franc to 2 dollars back then, so that’s around US$1,400 in the 1860s, which would be worth around $43,900 today – a bit of a punt for one night at the gaming tables, and then Dostoevsky pawned his watch…

5. Nick Leeson

Nick Leeson on on the cover of Time magazine, March 13, 1995

There’s nothing more exciting than gambling with someone else’s money. If you win, you win, if you lose, some other sucker foots the bill. At least, that’s what happened in the case of former stockbroker Nick Leeson.

Bankers have had a short shrift since the 2008 financial crash. Leeson can top that, and could be considered something of a trend setter, effectively bankrupting Barings Bank (formerly the UK’s oldest merchant bank) back in 1995.

Leeson’s story was that big he wrote a book about it, Rogue Trader: How I Brought Down Barings Bank and Shook the Financial World (1996), which subsequently became a 1999 UK box office flop with Ewan McGregor starring as Leeson.

After leaving school in Hertfordshire, England, at age 18 in 1985, Leeson began a career in banking, starting off as a clerk for Coutts private bank. Leeson switched to Morgan Stanley in 1987, working in the Futures and Options office, before moving to Barings in 1989. After stints in both Hong Kong and Jakarta, Leeson moved to Singapore in 1992. Here he took on the role of general manager of the newly opened Future and Options office at just 25 years of age.

Lucky Number Eight

This is where it all went pear-shaped. In his role as both manager, and chief trader (roles usually held by two separate people) Leeson created an error account, initially for a colleague to hide a trade that went bad. This became the infamous five eights account – 88888 – eights being considered a lucky number in Asia. Leeson began making unauthorised trades on this account.

At first, things went well, with Leeson running like Jesus and spinning the account up to £10m by the end of 1993 – accounting for roughly 10% of Barings’ annual trade. This made Leeson Barings’ golden goose and earned him the complete trust of his bosses. A six-figure bonus followed, and buoyed by his early success, Leeson continued to trade on the account. However, things did not quite work out to plan and by the start of 1994, the account was down £2m.

By December 1994, the 88888 account was stuck £208m – close to 50% of Barings’ total operating capital. Barings began to run out of liquidity. However, Leeson managed to play off his reputation to hide the fact until it all went horribly wrong. On January 16, 1995, in an attempt to win back his losses utilising the Martingale strategy – where a gambler doubles his bets after a loss in the hope of a win that then yields a net profit – Leeson placed a short straddle on the Tokyo Stock Exchange not moving significantly overnight.

Unfortunately for Leeson, on January 17, the Kobe earthquake hit and Japan’s stack exchange tanked. Desperate to bet his way out of trouble, Leeson took an even bigger risk, betting that the Tokyo Stock Exchange would recover – it didn’t. Now £827m in the hole (~US$1.4bn) Leeson wrote a note reading “I’m sorry” and fled Singapore. Eventually arrested in Frankfurt, Leeson was extradited back to Singapore, subsequently serving six and half years in Changi Prison. Now that’s what we call a gamble.

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