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

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. 

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Trent, who is in her 40s, hadn’t had much luck with online dating, but this guy seemed promising. He was smart and good-looking and she especially liked that he was outdoorsy. After exchanging a few messages, she gave him her number. When he called that evening, he introduced himself as Jeff Cantwell. He said he was born on Kodiak Island, Alaska, and had recently moved to Colorado Springs, where he was training to be an arborist. Most guys Trent had spoken to from dating sites were gross, bringing up sex during a first phone call. “Jeff didn’t do that,” she says. “He wanted to know about my favorite flower.” They ended up talking for ten hours. 
Two days later, Trent and Cantwell met for burgers. The connection they made on the phone seemed to deepen in person. They talked about Pikes Peak, which he claimed to have climbed over 200 times, and he also told her how he had lost his parents in a car crash when he was 18. When the bill came, Cantwell paid. A few days later he came over and made spaghetti with meatballs for Trent and her two daughters.
Over the next week, they texted and talked every day. To Trent, it seemed like they grew closer with each conversation. She asked if he had ever been married, and Cantwell revealed more about his history of heartache and loss. During the car accident that killed his parents, his fiancée, and his five-month-old baby were also killed, he said. He enlisted in the army and deployed to Afghanistan, where he was the victim of a severe knife attack. He apparently found some consolation in nature, however. He showed Trent tattoos on his calves that he said he earned for completing hiking’s so-called Triple Crown—the Pacific Crest Trail, the Continental Divide Trail, and the Appalachian Trail.

(Courtesy of Jeff Caldwell)

That weekend, when Cantwell said his bank card had stopped working, Trent lent him a couple hundred dollars. She trusted him. On Monday morning, when she let him borrow her blue Audi A4 to go get a new bank card, she figured he wouldn’t be gone long. About 30 minutes later, however, Cantwell texted that he’d need to go to the branch in Denver, more than an hour away. He asked if he could use the credit card she left in the car to get gas. Trent gave him the go-ahead, but now she was getting nervous. She didn’t remember leaving her card there.
Cantwell’s behavior grew stranger that afternoon. He claimed the bank in Denver had already closed by the time he got there. “I’ll have to sleep in the parking lot,” he told Trent. She knew something wasn’t adding up, but she didn’t want to believe the worst. “I thought we had a connection,” she says.
When Cantwell’s texts became increasingly erratic that night, Trent finally called the El Paso County Sheriff’s Department. They used Cantwell’s cell-phone number to identify him as 44-year-old Jeffrey Dean Caldwell, a Virginia native who’d been locked up in three states for seven felonies, including burglary, writing bad checks, and attempted escape. Most recently, he’d been paroled in September 2016, after serving time in Colorado for identity theft. But in April, shortly before he met Trent, he had stopped reporting to his parole officer.
Still, Trent couldn’t quite convince herself that the man she’d met had such a dark side. “Can I hear your voice one more time?” she begged him in a text. Part of her wanted to trick him into returning the car. Part of her still believed the man she’d fallen so hard for had to exist somewhere. “I don’t want you to go to prison. We have to figure out a way out of this. Can we leave the state?”
Caldwell did call her one last time, but when she started sobbing, he hung up. “I’m sick in the head,” he texted her. “Write to me in prison.”

The cops put out a warrant for Caldwell’s arrest, but he wasn’t known to be violent and no one expected he’d be locked up any time soon. “These con men are transient and move around a lot without any way to track where they are,” says Lieutenant James Disner of the Larimer County Sheriff’s Office, which had arrested Caldwell almost a decade ago. “I have been successful in a few of these types of cases, but only by reaching out to the communities they prey on.”
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, 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. On his Couchsurfing account, he used the name John McCandless, the same middle and last name as Christopher McCandless, the charismatic wanderer profiled by Jon Krakauer in Into the Wild.

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.
At the end of each con, he would apparently be wracked by regret, sending messages to victims that often began with him sounding apologetic and self-pitying, then switching to angry and entitled. “You were a means to an end. Adios,” he wrote one woman. “No crime done, just sniveling broads.” The moment the authorities caught Caldwell, he would confess everything.
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.

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