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Harry Bensley – the man who walked around Europe in an iron mask to win a bet

Tijana Radeska
Harry Bensley

One evening in 1907 at  the National Sporting Club in London, two men had an interesting conversation debating whether a man could go around the world with a mask on his face without ever being identified.

Lord Lonsdale, known as the ‘Sporting Peer’, believed that it was possible, while an American millionaire – John Pierpont Morgan argued that it was not.

John Pierpont Morgan

John Pierpont Morgan

The conversation was overheard by local rake and adventurer Harry Bensley who accepted the challenge of proving the feat possible. Bensley was thirty-one years old at the time, was married, and had an annual income of £5000. The bet between Lonsdale and Morgan was set and the winner would get £21,000. But the challenge was not simple. There were 15 conditions that Bensley had to satisfy and in order to do so another man was paid to go with him.

First of all, to win the bet, Besley was never to be identified. He was supposed to go through specified British towns and 125 towns in 18 other countries with an iron helmet on his head weighing about two kilos. In each town, he was to get a signature from a local prominent resident so that he can provide a proof of his visit. Also, the order of the towns he would visit was pre-specified.

Other conditions were that he would leave on his journey with only a pound in his pocket and that he would earn money by selling pictures of himself. He was never to take the mask regardless of the situation he might be in. The only thing he could change was his underwear. Throughout his journey, he was supposed to push a baby carriage and also, even though he was already married, Besley was supposed to find a wife who would agree to marry him with the iron mask.

Harry Bensley, 1908

Harry Bensley, 1908


Bensley started his journey from Trafalgar Square, London on 1 January. What happened on the road could never be confirmed with certainty but there are various stories. Supposedly, he traveled for six and a half years. During his journey, he met King Edward VII at Newmarket races and sold him a postcard for £5. The king also asked for Bensley’s autograph.

There is also a story that he got arrested at Bexleyheath, Kent for selling postcards without a license after which he was ordered to take off his mask. But as charismatic as he was, Bensley successfully explained the reason for wearing the mask to the officers and he was released with only a low fine.

He managed to cross 12 countries and to receive 200 marriage offers of which he accepted none. Apparently, there was a newspaper offering a £1000 reward to someone who would reveal his identity.

When the Great War broke out in August 1914, Bensley was in Italy. He was too much of a patriotic man to peacefully prolong his journey regardless of the fact that he would lose the bet. Instead, he joined the British Army and called off the bet receiving  a consolation prize of £4000 which he gave to charity.

King Edward VII

King Edward VII


Here is another fun story from us:The unsolved mystery behind the Man in the Iron mask

Unfortunately, he was wounded and had to leave the army in 1915. As a result of the Bolshevik revolution, Bensley’s investments in Russia became worthless and he became penniless in 1917. He died in 1956 in a bedsit in Brighton.