This diabolical hiker romanced and robbed women, luring them with his outdoorsy appearance and tales of wilderness adventure. In role-playing a "good-guy" and "outdoorsman," he successfully suckered dozens of victims through similar means: sob stories, scares, going on the lam, and eventually breaking their hearts. He violated the trust of a tight-knit community of outdoor enthusiasts, scammed dozens of people, and tried to lie his way into a life that doesn't exist.
Through an in-depth interview with Outside magazine, the (mostly) true story of Jeff Caldwell and his career as a con man and wanderer has now fully come to light. Though it turns out he may actually be a real outdoor enthusiast, he's most definitely a con artist and a pathological thief.
His Tactics Targeted Women Who Loved Outdoors Adventure
Jeff Caldwell created a very effective formula for luring women and conning them. He always came off as pleasant and courteous, outdoorsy and adventurous. Victims recalled him being very conversational. Eventually, as he got to know the women, he'd weave in a tale about the sad life he had led, embellishing or modifying true events. He'd follow it up with his dreams for the future and optimistic plans for his life of adventure. Then he would present his victim with a gift of some kind, small and sentimental, often accompanied with selfies of himself in the mountains to reinforce his outdoorsman persona.
Once he had won a woman's trust, Jeff would convince her that he needed to borrow cash, credit cards, or other items of value. If she said no, he just stole whatever he'd asked for and bailed. He would stick around anywhere from a few days to a few years to get what he needed.
His Sign-Offs To His Victims Were Pretty Brutal
Despite initial success drawing women in, Jeff Caldwell had a hard time connecting with people on a real emotional level in the long term. After he stole his victims' things and went on the lam, the women would be devastated and try to win him back. One victim, Melissa Trent, admitted that getting her stolen car back was almost secondary to just wanting to hear his voice again. But his lack of feeling is evident through the texts he sent after his victims found out that they had been conned.
"I’m sick in the head. Write to me in prison."
"You were a means to an end. Adios."
"No crime done, just sniveling broads."
He Lied About Completing Hiking's "Triple Crown"
In 2015, Caldwell told the American Long Distance Hikers Association that he had completed the "Triple Crown" of long-distance hiking, a feat which includes the Pacific Coast Trail, Appalachian Trail, and Continental Divide Trail. The Association gave him their thru-hiker scholarship, and flew him to their annual meeting in Portland, Oregon. But not only did he take advantage of the organization, he also took the opportunity to swindle $500 from an elderly couple at the event.
Jeff Was Arrested Many Times, But Always Violated His Parole
Caldwell was arrested and put in prison for the first time as a teenager, but spent the next few decades of his life in and out of jail. Almost as soon as he got out, he'd get caught for something else and go right back in. The second time he was arrested was in 1997 (he wrote a bad check for $10.16), and he was given the chance to do a quick three months in prison instead of a longer parole sentence. He chose parole but he violated the terms and was put back in jail three times.