Crime | October 21, 2017 9:00 am

Meet Hiking’s Most Devious Con Man

Jeff Caldwell lured hikers with his tales of adventures, then he ripped them off.

Jeff Caldwell spent two decades luring hikers, couch surfers, and other women through his tales of adventure. But then, he would make up a personal crisis, and exploit their sympathy to rip the women (they were almost always women) off. Outside spoke to Caldwell while he was still on the run, and wrote up an intimate look at his life as a serial scammer.

Melissa Trent, a single mother in Colorado Springs, Colorado, was one of Caldwell’s victims. She met him through an online dating site, and they seemed to have a deep connection. He told her that his parents, fiancé and new-born had all been killed in a car accident and that he had enlisted in the army and was deployed to Afghanistan. Trent trusted him. But then, he asked to borrow money, and later, her car. He never returned. Trent called the police, and they used his phone number to identify him as 44-year-old Jeffrey Dean Caldwell (he had told Trent his name was Jeff Cantwell). He was a Virginia native. He’d been imprisoned in three states for seven felonies, writes Outside, including burglary, writing bad checks and attempted escape. He was paroled in September 2016 after serving time for identity theft.

Outside writes that most of his victims were elderly people and women. He found them in Facebook and Meetup groups for hikers, using Couchsurfing.com, or he would hang around trailheads, hostels, and outdoor gear stores. When he met Trent, he had been traveling the West for over a decade, presenting himself to his victims as a “free-spirited outdoor archetype).

He also almost always did the same routine. He would nab his victim with his tale of woe, but then entice her with his tale of adventure and his big plans. Then he would give her a gift and send selfies from the mountains. Finally, he would make up a personal crisis and ask for a small loan, or he would steal. His relationships varied between a few days to a few years.

Outside was finally able to track him down, and he was willing to speak on the phone. He told the organization that he hoped if he came clean publicly, he couldn’t keep taking advantage of people.

“There has got to be a reason why I’m here,” he said to Outside. “There’s got to be. It can’t be to keep scamming people.