A Brief History Of London's Wackiest Wagers

A Brief History Of London's Wackiest Wagers
Image: Shutterstock

For centuries, Londoners have unable to resist the thrill of a good gamble. From grisly animal fights in working-class pubs to ridiculous high society wagers that function as a form of conspicuous consumption for the super-rich, this city has seen it all. Here are some of the downright wackiest.

The Drowned Servant

London's exclusive gentlemen's clubs have always been hotbeds of hedonism, and that includes a whole lot of ridiculous wagers. But it was at White's, the oldest and probably the poshest of them all, where perhaps the most breathtakingly stupid and tragic bet of all time was set when one member challenged another to see if his manservant "could breathe unaided underwater for 12 hours". Reader, he could not.

Image: The Gaming House, A Rake's Progress by William Hogarth. An early depiction of White's

The Man In The Metal Mask

Here's another ridiculous bet from clubland, this time courtesy of the now-defunct National Sporting Club. The story goes that American financier John Pierpont Morgan and Hugh Cecil Lowther, the 5th Earl of Lonsdale spent an evening here in 1907 arguing whether or not a man could walk around the world without being recognised. Harry Bensley, a notorious rake, overheard their conversation and volunteered himself for the task.

However, Bensley's great-grandson contests that his ancestor was obliged to take part as a forfeit for outstanding gambling debts. That might explain a bizarre twist in the wager: Bensley would have to wear an iron mask and push a pram for the entirety of his travels. Bensley duly left Trafalgar Square in this get-up the following year, and rumours of his exploits including an arrest, hundreds of marriage proposals, and a possible encounter with the King abound. Sadly, the accuracy of such tales are questionable, and there's no concrete evidence that Bensley ever left England.

The Bloody Boozer Bet

Of course, betting isn't just for toffs; London's pubs have a rich, if sometimes gruesome, history as places for the working class to have a flutter. The Queen's Head in Piccadilly was one such den of iniquity, hosting 'ratting' contests — a cruel sport which involved betting on how many rats a dog could maul within a specific time frame. The pub, which dates back to 1736, is still around today and still displays a photo taken at one such contests today.

England's Ugliest Man

Known in some quarters as the 'Ugly Count', Swiss-born aristocrat John Heidegger was renowned for his, ahem, unconventional looks. So vile was his visage that the man himself didn't believe that there was anyone uglier in all of London. However, Philip Dormer Stanhope, 4th Earl of Chesterfield took up the challenge to prove him wrong. The earl eventually found a woman who he deemed uglier than Heidegger. However, when the latter tried on the former's hat, he was declared the winner.

A portrait of John Heidegger byJean-Baptiste van Loo (1684-1745). Image via Wikimedia Commons

The Twins And The Artist

Ok, so this one isn't a weird wager per se, but it'd be remiss of us not to mention the Kray twins in an article about London's gambling culture. And this story's a real doozy. It begins with the late artist Lucian Freud, a notorious gambler who was eventually banned from the racetracks due to his debts.

For a time, his addiction was fed by none other than the Kray twins — according to the painter himself, he once owed these notorious East End gangsters half a million pounds. The twins had fed his gambling addiction for some time, but he was only able to pay them back incrementally, and once even cancelled an exhibition for fear of retribution.

A recent biography includes an anecdote from Freud's friend, Lord Rothschild, who recalled the artist saying "If I don’t give them £1,000, they’ll cut my hand off.’  Thankfully, the painter's illustrious friends were able to stump up the cash and his digits remained intact.

The Bet That Built An Empire...

William Crockford had a humble start in life. Born to a fishmonger in Temple Bar in 1776, he initially inherited his father's profession. However, he had a knack for numbers and odds calculation, and by his mid-twenties he'd become a professional gambler. By 1827, things had really taken off for Crockford and — as the story goes — it was all down to a single bet.

During a single game of Hazard, a popular dice game of the Regency era, Crockford allegedly won an eye-watering £100,000 (that's over £1.6 million in today's money). He used the money to found his gambling empire: the notoriously fancy Crockford Club which played host to many an aristocrat and socialite, including the Duke of Wellington.

50 St James's Street, the former premises of Crockford's. Image via Wikimedia Commons

...And The One That Brought London To A Standstill

In 1809, a young Londoner named Theodore Hook bet his friend Samuel Beazeley that he could turn any house in London into the capital's most-talked-about address for a week. To achieve this, he wrote thousands of letters under the name of Mrs Tottenham requesting that goods, visitors and other forms of assistance be sent to her home of 54 Berners Street in Westminster.

And thus, the Berners Street Hoax was born. On 27 November, Mrs Tottenham received a dozen chimney sweeps, several fishmongers and cakemakers, and even a man with a "large organ" (no innuendo intended). The commotion tempted even more onlookers, including such luminaries as the Mayor of London and the Archbishop of Canterbury.

Last Updated 02 June 2021