At Outside, Brendan Borrell profiles thru-hiking scam artist Jeff Caldwell, a man who started his life of crime by stealing from his friends. Later, using an outdoorsy trail persona, lies, and rugged good looks, he preyed on lonely single women and the elderly, robbing them not only out their money, but also of their belief in the basic goodness of humanity. Clearly unable to stop himself, Caldwell even started to groom Borrell as a mark during their correspondence for the piece.
Caldwell’s victims typically fell into one of two communities: elderly people and women, whom he often found by participating in Facebook and Meetup groups for hikers, by using the website Couchsurfing.com, and by hanging around trailheads, hostels, and outdoor gear stores. By the time he met Trent, he had been traveling across the West, presenting himself as a free-spirited outdoor archetype, for over a decade.
A pattern emerged with each of Caldwell’s cons, too. He’d scope out a victim, share his tale of woe, then enthrall her with his adventures (“31 wolves talking to each other!”) and quixotic pursuits (“I’m buying land. 155 acres. You can come stay with me. . . putting up a yurt”). Next, he’d give her a sentimental gift—say, an Alaska shot glass or an Appalachian Trail patch—and send her selfies from the mountains. Finally, he would orchestrate a personal crisis that ranged from the plausible to the bizarre, and finish it off by asking for a small loan or else he’d just steal what was lying around. The con might be over within days. In a few cases, he was able to stretch out such a relationship for years.