Harry Bensley and a Very Bizarre Wager

Updated on July 2, 2018
Rupert Taylor profile image

I've spent half a century (yikes) writing for radio and print—mostly print. I hope to be still tapping the keys as I take my last breath.

This is the story of a bet involving a billionaire, an aristocrat, and a playboy, which sounds like the start of a bad joke. The billionaire was John Pierpont Morgan and the aristocrat was Hugh Cecil Lowther, the Fifth Earl of Lonsdale, known as the “Sporting Peer.” The playboy will come into the picture shortly.


A Gentlemen’s Club

In 1907, Morgan and his lordship were at the National Sporting Club in London. This venue had been set up by Lord Lonsdale and a few friends to promote the sport of glove boxing and drag pugilism away from unseemly ruffians who engaged in bare-knuckle fighting.

Bouts took place after dinner and in complete silence except for the sound of boxers whacking each other senseless.

However, fighting aside, the club was also a place for playing games of chance, often for vast amounts of money. And, on the night in question the two wealthy men were at a card table.

Lord Lonsdale.
Lord Lonsdale. | Source

Misfortune at the Card Table

Now it’s time to meet Harry Bensley. He is variously described as a playboy, an adventurer, a rake, and a rogue. When not acquiring these unsavoury descriptions of his character, Bensley was engaged in business with Imperial Russia; a relationship that is said to have yielded and annual income of £5,000 (about half a million pounds today).

On the evening that gives this yarn its start, Bensley was at the National Sporting Club and playing cards with Morgan and Lonsdale, two men whose pockets were very much deeper than his.

Apparently, Harry Bensley, gambled everything he had, and more, on one hand and lost. He was forced to admit – horrors – that he couldn’t cover his bet. “One just doesn’t do that in a gentlemen’s club old chap.”


A Wager Is Made

Seeking a face-saving way out for Bensley, Morgan, and Lonsdale created a challenge.

Lord Lonsdale believed it was possible for a man to walk around the world with his face completely covered and so be unrecognized. J.P. Morgan said it couldn’t be done. They agreed to put up £21,000 (worth nicely over than two million pounds in today’s money) to see who was right.

Another version of the story has it that Morgan and Lonsdale were arguing quite vehemently that a man could or could not walk around the world without being recognized. Bensley, overhearing the noisy exchange, volunteered to put the theory to the test.

Harry Bensley was the man who was to retrieve what was left of his tattered honour by undertaking the journey. The rules of the trip were set up:

  • Bensley was to wear a 2 kg (4.5 lb) iron helmet from a suit of armour so that he could not be identified;
  • He was to walk through 162 British communities in a specified order and then through 18 foreign countries;
  • He was to push a perambulator containing his only baggage, a single change of underwear;
  • He was given one pound to start with and had to finance the journey by selling picture postcards of his exploit along the way;
  • A minder had to accompany him to ensure there was no cheating; and,
  • He was to find a wife without her seeing his face or hearing him talk.

The nature of this outlandish agreement suggests that copious quantities of Dom Perignon might have been involved, but the historical texts are silent on this matter.

The helmeted Harry Bensley hits the road.
The helmeted Harry Bensley hits the road. | Source

The Adventure Begins

On January 1, 1908, Harry Bensley set off with his baby carriage and escort from London’s Trafalgar Square.

In Newmarket, he encountered King Edward VII and sold him a postcard for £5. In another town he was arrested for selling postcards without a licence.

By 1914, he is said to have completed his British tour and to have covered a dozen countries in Europe. He is also said to have received more than 200 marriage proposals and to have refused them all.

You may have noticed the insertion of the conditional “he is said to have.” That’s because there is some dispute about how much of the contract with J.P. Morgan and Lord Lonsdale Harry Bensley fulfilled. There are conflicting accounts of the Bensley odyssey and the only photographic evidence of his hike appear to have been taken in southern England.

There are stories of the man in the iron mask turning up in Canada, Japan, New Zealand, and China. These have to be taken with a granary of salt.

The Adventure Ends

The journey came to an end in Genoa, Italy, in August 1914. Austrian Archduke Franz Ferdinand and his wife Sophie had been assassinated in Sarajevo. Complex international alliances were triggered and the world descended into the bloodbath of The Great War.

Harry Bensley returned to Britain, his quest uncompleted, to enlist in the army.

It’s said that J.P. Morgan gave him a consolation prize of £4,000, which Harry then donated to charity. But, this is not possible because Morgan died in 1913. Perhaps the benefactor was Lord Lonsdale or the executors of Morgan’s estate.

Bensley fought for his country for a year before being seriously wounded and invalided out of the services. There was worse to come.

The Russian Revolution of 1917 wiped out all his investments and left him penniless. No longer the man-about-town, gambling with earls and billionaires, Harry Bensley took employment as a cinema doorman and, later, warden of a hostel.

He died destitute in 1956 at the age of 80.

A well-earned retirement for Harry’s boots?
A well-earned retirement for Harry’s boots? | Source

Bonus Factoids

It’s been suggested that the two plutocrats, far from setting up a frivolous prank, were out to punish and humiliate Harry Bensley for welching on his bets. If that’s the case, the plan backfired because Harry became something of a national hero.

There are photographs of Harry and his pram with a woman who is holding a child. It’s believed the woman was called Mabel and that the child is Harry’s. But, Harry did not marry Mabel; although he did marry a woman called Kate. That marriage may well have occurred before Harry took off on his trek, hence his serial refusals of wedlock while on the road.

A London newspaper is believed to have offered £1,000 to anyone who could reveal the true identity of the man in the iron mask. A hotel chambermaid, eager to collect the reward, hid under Harry’s bed but she was discovered before he took his helmet off and was ejected.

In October 1705, 20-year-old Johann Sebastian Bach walked from Arnstadt to Lubeck in Germany to hear the great organist Dietrich Buxtehude play. It was a journey of 470 km (290 miles) each way.


  • “Harry Bensley the Man With the Iron Mask and His Links to Thetford.” Sam Bellotti, Eastern Daily Press, February 16, 2018.
  • “Harry Bensley – The Man in the Iron Mask.” Ben Johnson, Historic U.K., undated.
  • “Historians Uncover Adventure of Man in the Iron Mask.” Kelly Egan, The Ottawa Citizen, August 14, 1999.
  • “Walk This Way.” Jackie Cosh, The Norfolk Journal, September 2004.
  • “What IS the Truth About the Man In The Iron Mask?” Tony Rennell, Daily Mail, January 2, 2008.
  • “The Man in the Iron Mask, Harry Bensley.” The Official Harry Bensley Web Site, undated.


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    • Miebakagh57 profile image

      Miebakagh Fiberesima 

      18 months ago from Port Harcourt, Rivers State, NIGERIA.

      Thanks, Rupert for another interesting story. It is unfortunate that H. Bensley could not complete the journey and take the whole bet. However, joining the army and becoming a hero is worth a man's effort.


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