In the thru-hiking community, he called himself Mr. Breeze. On dating website Plenty of Fish, he was "lovetohike1972." But to those who've encountered Jeff Caldwell over the past two decades, he's perhaps best known as a con man who gains a person's trust only to exploit it, apparently without difficulty. "I saw how easy it was to be charmed by him," writes Brendan Borrell, who profiles Caldwell in Outside. A "troublemaker" as a teen, Caldwell bounced between foster families before falling in with outdoorsy friends at 18. They were his first victims. He'd nab a checkbook here, a camera there, keeping up the habit even after several stints in prison. But as he moved around the country, the hiker came to target women in particular. He'd gain their trust—telling "useless" lies for "self-aggrandizement"—then make off with cash, credit cards, and a vehicle.
Communicating with Borrell while on the run for alleging stealing a woman's car, Caldwell is vague about his motivations, but he suggests he enjoys manipulating women, even those he claims he truly loved. "They keep offering to help, so you say 'OK.' It's so comfortable," Caldwell says. "I am a nice person, but I have that evil person that's also there." Following his arrest in July—as a repeat offender, he could face 25 years if convicted—Caldwell tells Borrell he might simply feel more at home behind bars. "I'm glad this is over, actually ... I do feel bad for everything," he says. Perhaps that's the truth. Or perhaps Caldwell's Facebook profile, edited by an alleged victim after she found his password, is more accurate. "I am a conman," it reads. "I befriend people posing as a nice, hiking fellow. I steal from them then disappear." Read the full piece for a psychologist's take. (Read more con man stories.)