What I Found on the 365-Mile Trail of a Lost Folk Hero

A few days later, The Peekskill Blade printed a facsimile of this odd answer, just as the Old Leatherman wrote it. What did it mean? There were debates. Some thought the Old Leatherman must have been writing his birthday, in the European style: “15/3/42” — or March 15, 1842. (This would have made him 42 years old.) Some, drunk on the mythology of the Old Leatherman, took it at face value, as evidence that he was 15,342 years old. Decades later, the researcher Allison Albee offered this speculation: “One guess being as good as another, perhaps the Leather Man, understanding neither the question nor the meaning of Mr. Darrow’s figures, showed his own peculiar method of writing one, two, three, four, five.” Or maybe it was some kind of inscrutable code.

This, to me, is the perfect Old Leatherman story: an absurdly specific data point with no clear explanation. We know plenty of facts about him: his height (roughly 5-foot-7), the weight of his suit (60 pounds), the length of his homemade hatchet blade (9¼ inches). And yet the man himself was, is, and probably always will be a mystery. This is what I love, what keeps me circling back to him, over and over. The Old Leatherman is an engine of infinite interpretations — a story about stories. He gave us so little, and in doing so he gave us so much. In the 19th century, he was a perfect blank screen onto which society could project its fears and fantasies. And he remains so today. This is the real Old Leatherman’s loop, the one that we all walk, every second, on every level, eternally: the loop between reality and meaning, what we know and what we imagine.

The Old Leatherman’s last loop came in March 1889.

For months, it had been clear that something was wrong. The Old Leatherman was sick. In the later photos, you can see it: his bottom lip is swollen, marred by a “raw sore.” This was almost definitely mouth cancer, almost definitely from the tobacco that he liked to either chew or to smoke in his homemade pipe. (The Old Leatherman would often stoop down in front of post offices and general stores to pick up cigarette butts people had thrown in the dirt.) When he ate, he covered the sore with a special patch of leather. One house he stopped at for breakfast belonged to a doctor, and the Old Leatherman allowed him to examine his lip. The doctor gave him some ointment.

But things got worse. The sore deepened into a hole that eventually ate away half of the Old Leatherman’s jaw. He could hardly eat. He had to soak his food in coffee, then drink it, and some of it would come pouring right through his face. His walking got slower and slower. He began to lose weight. Still, he kept going.

Finally, people along his loop decided to try something drastic. In Middletown, Conn., residents set up a sort of sting operation. When the Old Leatherman stopped for a meal, as he always did, at the house of Amy Guy, she sent a messenger two miles up the road to his next stop, the Fisher house. When the Old Leatherman showed up there, he encountered a group of strangers: the police chief, the town physician, representatives of the Connecticut Humane Society. They “arrested” him, benevolently, and got him into a carriage. According to one of the Fishers: “He went with no reluctance and seemed to understand why — though the conversation was carried on by signs mostly.”