One evening in 1907 at the National Sporting Club in London, Pierpoint Morgan and Lonsdale were arguing whether a man could walk around the world without being identified. Bensley, a notorious "playboy" and womaniser with a substantial private income, overheard the conversation and offered to test the proposition on their behalf. The outcome of the exchange was that Lonsdale bet Pierpoint Morgan the, then extravagent, sum of USD 100,000 that Bensley would complete a pedestrian circumnavigation while satisfying 15 additional conditions, including:

• Bensley was never to be identified;
• Bensley was to finance himself, starting off with just GBP 1;
• Only a change of underclothes was allowed as baggage;
• He was to complete the journey wearing an iron mask from a suit of armour;
• He was to push a perambulator (baby buggy) the entire journey; and
• On the journey he was to marry a wife without her seeing his face.

There is some dispute as to to what extent Bensley had actually complied with the terms of the wager when, in August 1914, he found himself in Genoa, Italy, claiming to have completed 30,000 miles of the journey and having only seven countries remaining on his itinery. That month, World War I broke out and Bensley abandoned his journey, returning to fight for his country. Invalided out of the army in 1915, Bensley's fortune was ruined in the Bolshevik revolution, leaving him destitute. After a sequence of low status jobs including cinema doorman and inspector at a amunition factory, he died in a bed-sitting room in Brighton.

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