Inside the Mind of Thru-Hiking’s Most Devious Con Man

The purpose of this article is to warn others about potential con men, not to sensationalize the con. For more than two decades, Jeff Caldwell has lured in hikers, couchsurfers, and other women (and they're almost always women), enthralling them with his tales of adventure. Then he manufactures personal crises and exploits their sympathy to rip them off. The writer corresponded with Caldwell while he was still on the run, and came away with an intimate look at the life of a serial scammer who's found his easy marks in the outdoor community.

On a Thursday in late April, Melissa Trent, a single mother in Colorado Springs, Colorado, logged into her account on the dating website Plenty of Fish and had a new message from a user called “lovetohike1972.” “I can’t believe a woman as pretty as you is on a site like this,” he wrote.

Trent clicked open the man’s account. The photos showed a smiling, clean-shaven guy in a Marmot puffy with chunky glasses and shaggy hair curling up from under a baseball cap. Trent thought he looked cute. There were shots of him atop Pikes Peak, hanging out with thru-hiking buddies at a hostel in Seattle, and climbing into a tractor in Montana. “I love adventure,” he wrote in his profile. “Anything in the outdoors.” His interests included hiking, biking, skiing, craft beer, and the occasional toke.

A pattern emerged with each of Caldwell’s cons. 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.

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