Inside the Mind of Thru-Hiking's Most Devious Con Man (Outside)
As I learned about Caldwell’s exploits, I wondered if there was something about the outdoor community and our sympathy for such wanderers that may make us especially easy marks. When we see a man with a trail-worn Gore-Tex jacket and a decade-old Dana Designs backpack, we instinctively trust him. We can’t help but envy his authenticity, his freedom. He’s not just a weekend warrior—he’s living the life we want. Or at least, that’s how it seems.
For six weeks, I texted Caldwell at a number that Trent had given me, but he never responded. Then, on June 27, he finally sent me a text along with a photo of himself sporting a blue flannel shirt while lounging on a rolled-up fleece in a pine forest. When we spoke on the phone a couple days later, I could hear birds chirping. At first he told me he was in northern Arizona. Later, he claimed he was near the popular Barr Trail on Pikes Peak. “I know Pikes Peak,” he said, “I can hide on this mountain for a long time.”
He agreed to speak with me because he hoped that, by coming clean in public, he wouldn’t be able to take advantage of anyone ever again. “There has got to be a reason why I’m here,” he said. “There’s got to be. It can’t be to keep scamming people.”