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Famous Wagers And Gambles

Updated: Jan 24

By Amy D'Orazio, author of Wits & Wagers

In November 2022, the biggest gambling payout in sports history was made to a Houston millionaire known as Mattress Mack who turned a wager of $10 million into a $30 million win, betting on the Houston Astros baseball team. That was only his single-payout winnings—from other wagers he placed on the team throughout the season and in various venues, he received an estimated $75 million total. Happily he’s not the only beneficiary of his winnings; a furniture retailer, Mack’s stores offer to refund double the cost of their purchase to any customer who spent at least $3,000—if the Astros won the World Series.

And yet, despite his big win, Mack is nothing to the high-stakes gamblers of the Georgian and Regency eras. Fortunes—and family estates—were won and lost over the gaming tables. It was nearly an epidemic of gambling addiction.

The gentleman’s club White’s, established in the late 17th century as a place to indulge in chocolate, soon became a place for aristocrats and nobleman to play games of chance, like Faro or Hazard. Other clubs arose throughout the 18th century—Brook’s, Crockford’s, The Cocoa Tree, and Almack’s—for the same purpose, for the wealthy to amuse themselves and see if perhaps Lady Luck would favour them with a win.

Of course, many of these men became considerably less wealthy as a result of their misfortune at the tables. In 1719, the Duke of Richmond was forced to settle his debts by marrying his 16-year-old son to the 13-year-old daughter of the Earl of Cadogan. Lord Holland was forced to pay a sum of £140,000 pounds (worth approximately £9.1M/$11M in today’s currency) to settle his second son’s (Charles Fox’s) gambling debts. Lord Thanet lost his entire income of £50,000 pounds in one sitting. The deepest play ever recorded happened in the 1770s when £5000 were staked on one card during a game of Faro. Altogether £70,000 pounds changed hands that evening.

The massive losses being incurred throughout the aristocracy led to several attempts by the government to gain control of things. They did so by outlawing certain games of chance, such as Faro. The purpose of these laws was to prevent ‘excessive and deceitful gaming’ but their true outcome was that people could not seek redress of either debts owed or incurred in the courts. As a result, debts became a matter of significant honour; the clubs kept books naming the parties involved in debts and to renege on those debts meant losing your membership in the club as well as any standing and respect you had in Society at large. A man paid his debts of honour even before he settled payments owed to merchants, tradespeople or servants.

Outlawing certain games did nothing at all to quell the madness for wagering; those who wished to play the games found more private venues and within the clubs, wagers moved towards games of a more individual nature. As the 18th century moved into the 19th, gentlemen (and ladies, in different venues) found increasing enjoyment in wagers of anything and everything imaginable. Many of these centred on political events of the day:

Many others focused on more personal things such as marriages, births and deaths, although in 1774 it was outlawed to wager on the deaths of peers and aristocrats.

But the most entertaining to read are the outrageous wagers! Below is a list of some of the more offbeat, shocking, and sometimes tragic wagers that I read:

  • The girl in a balloon bet (Brooks’s, c. 1794): Lord Cholmondeley wagered two guineas against Lord Derby from Derbyshire that he would have sex with a woman in a balloon one thousand yards from earth.

  • The Earl of March bet that he could cause a letter to cover 50 miles in an hour. Most people assumed the bet was impossible to win as even the fastest horses could only travel 30 miles in an hour. However Lord March outwitted them all by enclosing the letter within a cricket ball, then arranging for 20 cricketers to stand in a measured circle throwing the ball amongst themselves as fast as they could. The earl won £10,500, which in today’s currency would equal £1.6M or about $2M.

  • In 1784, a Mr Boone bet a Mr Rigby at Brooks’s that 'his Prick is within an inch as long as Mr Halsy’s'.

  • In 1809 Captain Barclay was bet that he couldn’t walk one mile per hour for 1000 hours. He completed the challenge on July 12, 1809, at one point (mile 607) needing his aide to beat him awake to keep going. He lost over 40 pounds (3 stone) in the course of the challenge!

  • One member of White’s reportedly bet another that his manservant could breathe unaided underwater for twelve hours. He could not, and the servant drowned.

  • John James Heidegger wagered against Lord Stanhope that he (Heidegger) had the ugliest face in London. (He was famously referred to by the King as 'Count Ugly' or the 'Dwarf Baboon'). Lord Stanhope eventually found a woman that he deemed uglier than Heidegger but when Heidegger tried on the woman’s hat, he was determined to be uglier than the woman and Stanhope was required to pay him.

And lastly, we can thank these dedicated gamblers and gamesters for a modern culinary staple. The 4th Earl of Sandwich, John Montagu, refused to leave the game tables even to eat, and in the late 16th century instructed his butler to bring him ‘a piece of beef between two slices of bread’. The trend caught on among his fellow gamblers who summoned their own butlers to bring them ‘the same as Sandwich.’


The Honourable Algernon Bourke. The Betting Book of White’s 1743-1878

John Griswold. Ian Fleming’s James Bond: Annotations and Chronologies for Fleming’s James Bond Stories

Andrew Steinmetz. The Gaming Table.

George Otto Trevelyan. George III and Charles Fox

All images public domain

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Nov 30, 2023

Read and highly enjoyed this book. Best wishes with its further release.

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