The Mysterious Identity Of The ‘Old Leatherman’ Urban Legend

It’s March 1889, and the grim business of an inquest into a man’s death is underway in Sing Sing, New York. Two doctors, Joel D. Madden and Charles S. Collins, report their findings on the cause of death. They cite “lupus, or ‘wolf’ cancer” as the cause of death and note that this affliction “made frightful ravages in his mouth, almost destroying the lower jaw.” This unfortunate man’s life did not end at home in his bed, for he owned neither of those things. Instead, he died alone in a crude, makeshift shelter on a farm belonging to one George Dell near the village of Briarcliff Manor, New York.

The Old Leatherman

Although he was a well-known character who tramped along the roads of Connecticut and New York State for many years, his real name was a mystery: he was known only as “The Old Leatherman.” A carpenter called Henry Miller was the person who found the vagabond’s lifeless body. 

Miller told the inquest, “I went out for a walk with my wife on Sunday morning last, my wife expressed a wish to see the retreat of the Leatherman, so we went there. As we… [were] entering the hut, we… [thought] the man was asleep, but a second glance saw that he was dead.”

Leather suit

The farmer, Dell, was another who testified at the inquest. He said, “[The Old Leatherman] frequently stopped on my farm for a little over five years last past, in a rude structure he made in the woods for a shanty or a hut.” Dell also noted, “I thought he was a Frenchman. I asked him a few words in French and he answered promptly in French.”

Dell also explained the origin of The Old Leatherman’s name. “When I first saw him, 28 years ago, he wore then the same suit or one similar to it, and made of small pieces of leather, mostly boot legs sewed together with leather bands.”

An eccentric life

A second local farmer, Walter L. Whitson, gave evidence at The Old Leatherman’s inquest. He told the court, “The last time I saw him he looked ill and did not have the large bag. He was a mystery to me. I never knew him to work anywhere. He was about 60 years old.” 

But it wasn’t just Whitson who’d found mystery in the eccentric life of The Old Leatherman. People far and wide across New York and Connecticut felt just the same way. His lifestyle had been truly extraordinary, following a set routine that he repeated without fail over many years.

The Old Leatherman’s routine

This was his routine: he would walk a 365-mile circuit which took him precisely 34 days to circumnavigate. Connecticut History.Org described the route in a 2022 article. He made a “clockwise trip through southwestern Connecticut and adjacent sections of lower New York State.”

The piece continued, “The trips took him through Danbury, New Fairfield, Watertown, Middletown, and New Canaan, into Westchester, New York, back to Danbury and again to New Fairfield.” It had been in 1857 that The Old Leatherman first came to wider attention, although sure evidence of his repeated circuits is only available for the last six years of his life. But he’d wandered through New York and Connecticut for 33 years.