Iron Man: The Weird Wager of Harry Bensley, Who Walked 2400 Miles in a Helmet

It was as odd a sight as London had ever seen. On New Year’s Day in 1908, a crowd in Trafalgar Square gathered to observe a man wearing a helmet in the style of a medieval knight. In front of him was a perambulator, or baby carriage, that was devoid of any infant. Emblazoned on his shirt were the words masked, as though it weren’t obvious, and walking ’round the world. A sign sprouting from the top of his mask had the same inscription.

“Goodbye!” he shouted to those congregating, the words muffled by his headgear. “See you in 10 years!”

As he had explained to press, the man was about to embark on a bizarre journey in which he was determined to walk through hundreds of cities around the world while pushing the carriage. He declared he had been handed specific stipulations for completing the task, including that no one ever discover his true identity and that he be given no money or other means of support.

If he were to complete the walk, he would receive $100,000 (roughly $3.2 million today). While this was better than no reason at all, it still invited a host of questions. Who was paying him? And why? How could he prove he had traversed the globe? What would he do for money? Most importantly—who was he?

The answers would be forthcoming. But as one might expect, the man in the iron mask would prove a highly unreliable narrator.

1. The Wager
2. A Well-Traveled Lie

The Wager

The story began in 1907, when a self-proclaimed playboy in his early thirties named Harry Bensley walked into the posh National Sports Club in London’s West End and happened to overhear an animated conversation. Walking closer, he discovered that the two men speaking were American financier John Pierpont (J.P.) Morgan and the impressively wealthy Hugh Cecil Lowther, the 5th Earl of Lonsdale.

According to Bensley, he was friendly with Morgan and saw that Morgan and Lowther were in a lather over whether it would be possible for a man to navigate different cities in different countries on foot, pushing a baby carriage, and without ever being identified. The talk seemed to be heading toward no satisfactory conclusion when Bensley piped in.  

“This wager was laid by a friend of mine, a well-known American millionaire, as the outcome of an argument that took place at a club in Pall Mall,” Bensley said later. “He declared that no Englishman would walk around the world masked and pushing a perambulator. After hearing the conditions I at once made up my mind to accept the wager myself.”

There were several other conditions, all bizarre. Bensley could have 1 pound (roughly 100 pounds or nearly $130 USD today) in seed money but would otherwise have to support himself without accepting gifts or gratuities of any kind. He would have to don a helmet when out in public to avoid being recognized. He must push the baby carriage and have an escort. He had to travel to 169 cities and towns in the UK and 125 cities in 18 other countries. He had to find a wife during his travels. And to prove his feat, he’d secure signatures from the mayor or other official of each area he visited.

Bensley—though no one knew it was Bensley—set off January 1, 1908, with plans to journey through England before venturing off to Scotland, Canada, Japan, and beyond. Context for his journey appeared in newspapers, though one didn’t have to read a story to be struck by the sight of a man in a helmet pushing a stroller. Everywhere Bensley went, curious crowds gathered, some desiring photos which were distributed by his assistant, a man known only as Mr. Allen.

Their visits proved newsworthy. When they arrived in Penzance in April 1908, The Cornishman newspaper wrote: “The arrival in the town of such strangely equipped individual aroused no little interest, and a representative of The Cornishman waited upon him at the Golden Lion Hotel, where host Tom Martin is looking after his comforts … The Man in the Iron Mask is a well set-up individual, and his conversation betrays that he is man of considerable education and culture.”

His calves, the reporter added, “seemed equal to a long journey.”

The attention was the solution to Bensley’s biggest problem: money. For as little as a penny, he sold postcards, photos, and pamphlets, all bearing his likeness. The baby carriage acted as a place to hold his inventory. And business was brisk: At some stops he sold 600 to 800 mementos, enough to keep him solvent for food and lodging.

There were certainly inconveniences. At 4 pounds, 5 ounces, the helmet was an unnatural accessory that must have proven taxing. He removed it for eating, though if he had to be around others he would dine behind a screen. A room was also safe harbor, or so he thought: Once, a maid hid under his bed in the hopes she could catch a glimpse of the man with his mask off. (She was not successful.)

The greatest danger for Bensley’s anonymity turned out to be the law. He once sold a postcard to a curious child in Bexleyheath without giving it a second thought and without realizing the area he was in prevented commerce on the street without a proper license. He was hauled in before a judge and explained his situation. The court amiably allowed him to keep his mask on while being arraigned.

At the end of 1908, Bensley estimated he had walked 2400 miles, averaging 10 miles per day. Incredibly, he had even found a wife, who joined up with him on his trek. He had planned to head to Scotland next; to hit all the countries needed would take years.

While some newspapers had covered Bensley’s trip in earnest, others thought it too odd to regard with any sincerity. Shortly after his departure, a correspondent for The Province in Vancouver observed that “of course the man in the helmet is only advertising the baby carriage, the helmet, or himself. I don’t know which, but I know it’s one or the other.”

The unnamed columnist was on to something.

A Well-Traveled Lie

In January 1909, just one year into Bensley’s wager, he proceeded to detail what some had already suspected. There had been no wager in the West End club, no argument between Morgan and Lowther, and no $100,000. It was all simply a ruse.

Bensley had been serving time in prison for bigamy when he began reading about the man in the iron mask, a French prisoner circa the late 1600s whose identity had never been uncovered and who later served as inspiration for the Alexandre Dumas novel The Man in the Iron Mask. Bensley, who was not the man of means he sometimes portrayed himself as, settled on the idea of boasting of a wager in order to visit various towns and peddle his postcards for a profit.

Even his marriage was a sham—sort of. “One of the conditions … stipulated that I should find a wife ‘on the road,’ ” he said. “I already had a wife, and intended getting her to join me as soon as I could provide a suitable conveyance for her use.”

Bensley was able to entice investors for his scheme, securing money to begin printing postcards and purchasing a helmet, which he obtained at a theatrical costume shop. His escort “Mr. Allen” was merely someone who was helping to fund the enterprise.

How long Bensley was planning to continue this is unclear. But he did disclose why he stopped after just 10 months. “The strain began to tell upon me,” he said. “My eyes ached and suffered with racking pains in my head. On several occasions I fainted by the roadside, and sometimes I was even confined to my bed for two or three days at a stretch.”

Walking every day for miles had worn Bensley down. His condition concerned his wife, Kate, who insisted he stop the stunt. “I should have liked to have continued with it,” he said, “but circumstances were too strong for me.” Upon departing Wolverhampton in December 1908, he returned home, boasting he had supported himself and his wife and assistant for nearly a year on postcards and other paper ephemera alone.

At some point, however, Bensley appeared to have a change of heart regarding his fictional wager. He later resurfaced to declare he had been traveling right up through 1914 and that he had but a scant few miles to go on his estimated 30,000-mile path when the journey was aborted due to the outbreak of the first world war. J.P. Morgan, he said, paid him 4000 pounds, or roughly $420,000 today, as a kind of consolation prize.

There was a considerable problem with this story. Morgan died in March 1913, making it impossible for him to settle up on a bet unless Bensley had employed a spiritual medium. This version also ignores Bensley’s earlier confession. Given the times and how slow news was to travel, it’s possible he hoped that people may have missed his 1909 disclosure.

Indeed, they did. Subsequent stories about Bensley right up and on through his death at age 80 in 1956 repeated the broad strokes of the “wager” and his international walk credulously. His descendants later shared a version of the story Bensley himself related to them just before his death in which Bensley agreed to the wager, but not voluntarily. Instead, they said, he had lost too big a hand in poker and was forced into the situation to settle his debt. As it’s no more believable than his first explanation, it’s likely Bensley’s 1909 telling is the closest there is to the truth.

Bensley’s stunt prompted some copycat behavior. Danish journalist Marius Bernstarf Schroder declared he would travel the world while wearing handcuffs 22 hours a day; a pair known as Dianelli and Zenarchi stuffed themselves in a barrel, vowing not to emerge unless necessary while they were shuttled around; others were pushed around in wheelbarrows. All were said to be part of a wager.

As for Bensley, he likely never left the UK. Equally dubious is whether he ever met Morgan or Lowther. And rather than having a fortune, it appears he worked odd jobs after settling down in Essex.

Bensley imposed one additional condition on himself for the wager: He could don only one pair of underwear the entire trip. It’s a wonder he lasted as long as a year.

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