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A Hiker’s Trail of Lies

Couch-surfing con man Jeff Caldwell preys on the kindness of the outdoors community.

A Hiker's Trail of Lies - episode art


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This 2018 episode tells the story of Jeff Caldwell. Jeff has lived for decades as a couch-surfing con man preying on the kindness of the outdoors community. He spins tales of hikes he’s never completed and exploits the sympathy of his marks with sad stories of his past to rip them off. But after meeting Melissa on an dating site, Jeff’s lies finally catch up with him.

Editor's Note: This episode was originally published in September 2018.


[00:00:01] Michelle: This week on The Perfect Scam.

[00:00:03] He cleaned out my credit card and my bank account completely. And then took my car.

[00:00:08] It's kind of in the last decade or so that he really sort of fashioned himself into a full-on outdoorsy, you know, fleece wearing, hiker type to sort of gives him credibility in this community and, and help him, give him an entree to meet other people that eventually he would, he would betray.

[00:00:29] Michelle: Welcome back to AARP's The Perfect Scam. I'm Michelle Kosinski. This week's episode is about a nice wholesome, outdoorsy guy you could have met out there on the hiking trail. Rugged, handsome, little beard going, flannel wearing, craft beer loving, I mean how could you not trust him, right? Well, as you might have guessed, this guy was anything but trustworthy. A long, rocky trail of lies was more his thing. And you'll hear about the Colorado woman who hatched a plan to take him down once and for all. This is a chance to hear one of our stories you might have missed. As we get ready for a new season with all new scams coming very soon, sit back and take this one in. From deep in The Perfect Scam archives, episodes 20 and 21, hosted by Will Johnson. Enjoy.

[00:01:23] For AARP - The Perfect Scam, I'm Will Johnson. I'm joined, as always, once again by my cohost, Frank Abagnale.

[00:01:30] Frank Abagnale Hey, great to be here.

[00:01:31] Will Johnson: Nice to have you here again, Frank. And we have another scam story we will share in just a few minutes, but first, I want to ask you about a topic that I don't think we've talked about much, the various technologies where we're able to talk to our devices. A lot of security concerns going on there.

[00:01:43] Will Johnson: Yeah, very scary. Uh, when talk about those type of devices, you have to ask yourself, how is it activated, how does it work? It works on voice. So with a minor twitch from a hacker, I could listen to everything you say in your house, and when you look about all of these devices in your house; your Samsung TV, your remote control to the TV, uh, your refrigerator that tells you when you're getting really uh, low on milk, and even your security cameras that you have around your house because you think when I go away I can get on my iPhone, I can look at my house, see what's going on around my property; all those are access points for hackers. And uh, the reason is that people who develop these types of technologies, never go, what I call, through the follow-through final step and that is to ask the question, how would someone use this in a negative way? They're just more concerned about how do I get it to market, how fast can I get it to market, and they never go to that final step. So most of my uh time now is spent working with technology companies as an advisor, and those are good companies. They come to me basically to say we've developed this; how would you beat it? Where is the flaw in this system, because before we put it out in the marketplace, we want to know how someone would manipulate it or get around it.

[00:02:57] Will Johnson: You know, I just don't walk around my house saying my Social Security number anymore.

[00:03:00] Frank Abagnale: No. But there are a lot of things you do say, and uh, and especially...

[00:03:03] Will Johnson: There sure are, there sure are.

[00:03:06] Frank Abagnale: Especially if you might be an attorney working a very important case...

[00:03:09] Will Johnson: Right, so right, so it's not necessarily that the hackers will know what you're having for dinner, but there could be loftier security issues at hand.

[00:03:17] Frank Abagnale: Yes.

[00:03:18] Will Johnson: Oh my. What a world. I really enjoy the smart speaker we have in our house, but it does freak me out sometimes, and my wife's name is somewhat similar to the name of the speaker of the device that we have, so she will sometimes all of sudden just come on and say, you know something and, and it's alarming.

[00:03:35] Frank Abagnale: It is. It's a little scary. It's a little bit too much technology.

[00:03:38] Will Johnson: It is, no, it's way too much.


[00:03:41] Will Johnson: All right, Frank, from high tech to low tech we're going to get into this week's story, and we're going to tell our listeners about a serial scammer who made his mark in the outdoor community.

[00:03:54] Will Johnson: Not long ago, as we were looking into more stories for our podcast, we came across a really interesting article for Outside Online, all about a thru-hiker, a mountain man, an outdoor guy who also turned out to be a con man, pretending to be someone he's not, taking on guises in order to gain people's trust, and then take advantage of them. The article is written by Brendan Borrell. He first came across the story on a website called Mountain Project.

[00:04:19] Brendan Borrell: Yeah, well actually I'm, I'm a rock climber and I was checking on this uh climbing website called Mountain Project which has some forums, and uh I saw an unusual post from a woman named Melissa Trent who was frantic because she had, someone had just taken her car, it was a brand new Audi...

[00:04:38] Melissa Trent: And people all through Colorado Springs were warning about this guy. There were pictures of him and all of these victims saying yes, it's real, he's a con man.

[00:04:47] Will Johnson: Will: But all that comes much later. The story begins when Melissa comes across Jeff Caldwell's profile on a dating site.

[00:04:54] Brendan Borrell: He had uh posted a profile on um, a website called Plenty of Fish. His username was "Love to Hike 1972," and he advertised himself as the outdoors type, and Melissa was, was a single mom and uh she thought he was pretty cute. She wasn't super outdoorsy, but she liked that he was outdoorsy. She'd, she'd been turned off from dating websites before because guys were a little bit creepy and they would ask, you know, they would say sexual things really early on and he was actually a very um, a very kind guy.

[00:05:29] Melissa's in her 40s. She's been divorced for five years, lives in Colorado Springs with her two daughters. She isn't brand new to dating sites, and she liked Jeff right away.

[00:05:37] Melissa Trent: We started talking and we had a really good conversation through messaging, and he seemed really well spoken. You can tell a lot in people's texting, and he seemed well spoken, articulate, um, we had several things in common, and he wasn't, he didn't come on too strong, aggressively, like the conversation stayed very, very platonic, and I really liked that. And um, actually I think the second day that we started talking, we moved to the phone and we talked like 12 hours that day.

[00:06:12] Will: Wow, like in one conversation?

[00:06:13] Melissa Trent: Yes between texting and calling, um, it was a continuous um, I think it was like 10 to 12 hours that we were on the phone.

[00:06:21] Will: All right, so that's a clear indication there are some sparks. So there was something going on.

[00:06:25] Melissa Trent: Yeah, yeah.

[00:06:26] Brendan Borrell: He was a good-looking guy and he told me as he got more good looking with age, he, he claimed he was a little bit awkward when he was younger. Um, but as he got more good looking with age, he found that he could uh people really trusted him and, and uh that he could do almost anything.


[00:06:43] Will Johnson: But what Melissa doesn't know and comes to find out, is Jeff is not what he appears.

[00:06:48] Will Johnson: He'd been up to this for decades, uh at least various stages or elements of cons, right?

[00:06:56] Brendan Borrell: That's right. I mean, I mean from what I understood going back to his childhood is, is he came from a broken home and, and he became a bit of a trickster just to survive, you know, going around to neighbors' houses and begging for handouts and sort of telling stories that, that would make him friends and, and help him um, survive. And he never uh sort of left that, that, that became a pattern for him over the rest of his life, and so you know he, he pretty soon after he turned 18, he, he started uh getting into trouble with petty thefts and stealing from friends, and it's kind of in the last uh, decade or so that he really sort of fashioned himself into a full on, you know, outdoorsy, you know, fleece wearing uh Patagonia wearing, uh hiker type, you know, getting, getting tattoos for the various long distance trails, the Appalachian Trail and the Pacific Crest Trail, which he never actually fully hiked, um, but just to sort of give him credibility in this community and, and help him, give him an entree to meet other people that eventually he would, he would betray.

[00:08:05] Will Johnson: He was really good at, at telling stories of adventure that were totally bogus.

[00:08:10] Brendan Borrell: Yeah. I mean he, he, he did sort of puff himself up as having all these amazing adventures. You know, he told one woman that he was this uh ski instructor from Vail, uh then when they went out cross country skiing, he could barely stand up on his skis. I mean, he, you know, and again, he, he claimed he had hiked these long distance trails, but when people would go out with him, uh he would make it a few miles and then he'd be huffing and puffing and turn back.


[00:08:41] Will Johnson: After talking for four or five days, Melissa and Jeff decide to meet up in person.

[00:08:46] Melissa Trent: During that first meeting there were no big red flags. Um, he told me during that first meeting um, that he, that I asked about his, where his parents, you know where he was from and his parents, and he told me that his parents had died in a car crash when he was 18, and, and that was really the only thing that was a little bit you know, farfetched, but people's parents do die.


[00:09:13] Will Johnson: There is actually more to Jeff's story that he isn't telling Melissa yet; the version that Brendan Borrell knows includes not just Jeff's parents, but also a wife and a young child.

[00:09:24] Brendan Borrell: You know, part of his, his play was to elicit sympathies from his victims, and so he had this sob story about um, growing up in Kodiak, Alaska, of course a remote place, famous for grizzly bears and so on, um, but that he had uh gotten married, uh at a young age and had a um, had a young child and um, was driving in a car with his parents and they got in a car accident, and you know his wife, his child, and his parents were all killed.


[00:09:57] Melissa Trent: The next day, I asked him, 'cause we, we went out the next day, and I asked him if he had ever been married. And he, he kind of looked down and you could just see the, you know, just his face change, and I was like, what's wrong? And he was like, well, the part of the story that I didn't tell you yesterday is that when my parents were killed in the car crash, my fiancé and 5-month old daughter were also in the car.


[00:10:24] Will Johnson: Over the next two weeks, Jeff spends more and more time with Melissa and her kids.

[00:10:27] Melissa Trent: He actually stayed at our house, and the reason was, was because he claimed that the couple that he was staying with at the Airbnb um, were fighting all of the time in front of him, and it made him really uncomfortable, and so he was like, I think I'm just going to cut this short and try and find a hotel. And so I was like, well you can stay with us for a couple of days until you can find a place. And so he came on Thursday and stayed Thursday night, Friday night, Saturday night, and Sunday night.

[00:10:55] Brendan Borrell: You know, he came over and he made spaghetti and meatballs for the kids and he said, "I want to show the kids that I'm a great guy." And this all happened extremely fast. This was you know a, over a period of a week to 10 days, you know he, he hooked her and um, it's kind of shockingly fast to me, but I guess she was in a place where she was really um, you know, looking for someone, and he, he, he charmed her.

[00:11:21] Melissa Trent: We really liked each other, we had a lot in common, and he even, there was one day where my daughter asked if she could go um, if her and her friend could go to the mall, and he asked me, he, he came into the room and said, "Hey, how would you feel if I drove them to the mall? And I was like, why? And he was like, "'cause it'll give us time, you know to bond, and I can bosh the radio and they're really start to like me." And I was like, that's amazing. I can't believe, you know, cause he knows that in order to have a relationship with me, he's got to like my kids and they've got to like him, and I just loved that he was making that effort. Our third date, he came over, he brought food, he cooked the dinner for the kids, he got a menu of what they liked so that he made sure that he was cooking food that everybody liked. I mean he was; it was just amazing.


[00:12:07] Will Johnson: This is where the story really starts to shift into a another realm, and for the first time, Jeff mentions money.

[00:12:13] Brendan Borrell: And then one day he, he, they were out, and he said his bank card had stopped working.

[00:12:17] Melissa Trent: He claimed to be a veteran and you know he got VA benefits, and he said that his VA benefit had gone in for the month, but it had frozen his account. He was like, "This is the third time this has happened. For some reason whenever they deposit it, it freezes my account," and he, and I was like, "Oh my gosh, that's weird." And then he was like, "So can you just give me, you know can you, can I borrow you know like 100 bucks just to get through the weekend and then I'll pay you back on Monday?" And I said, sure. So, when he got there that afternoon, I asked him, you know, I wanted to go to Garden of the Gods and just walk around, and he was like "No, let's go to Cripple Creek and go gambling."

[00:12:50] Will Johnson: These are various areas around where you live.

[00:12:53] Melissa Trent: Yes, yes, around the, the Colorado Springs area. And um, Cripple Creek is a big gambling spot for people. It's about maybe 20, 30 miles away. And I had never been. And I was like oh, okay. And so we went, and we went to the casino and we went in and um, we went to the ATM so that I could get out 100 bucks to give him for the weekend. And when we were standing at the ATM, he was like, "Can you make it 200, and that way we can use 100 to gamble tonight, and then I still have 100 for the weekend?" So I was like, okay. And then he made a big production and turned around, so he didn't see my pin or anything, and I took the money out and I handed him the cash. And so we did that. We, we stayed in that casino for about 10 hours. We made that 100 dollars stretch for like 10 hours and then when the money was gone, we left. So the next morning, it was Monday morning, and this is the day that he's supposed to pay me back, and he had told me he would pay me for all the gas going to the casino, you know, he had borrowed 200 but he was going to give me 300 back. And so he borrows my car to go to the bank and about 30 minutes later, he messages and says, "We have a problem." And I'm like, "What's the problem?" And he said that the Colorado branch of his bank would not issue him a new debit card. He was going to have to go to Denver to get the debit card. And he was like, "Can I use your car to go to Denver?" And I was like, "Ah, I don't know. I mean like how long is, how long are you going to take?" He's like, "I'll be, you know, I'm going to go up there and I'll be right back. I should be back by noon."

[00:14:18] Will Johnson: You like this guy enough; he's been like around that there are zero red flags.

[00:14:22] Melissa Trent: Yeah, the only red flag and it, and I, and I noticed it as soon as he said it, when we were at the casino, um, he was talking to another guy. We were playing um, I don't remember what we were playing, but um, oh, Blackjack, and there was another guy at the table, and they were talking about Alaska, 'cause the other guy had spent some time in Alaska. And Jeff made a comment about his mom and he said, "My mom is Inuit." And that struck me, because my mother has been dead, at the time had been dead for about 12 years, and I would have never said she IS Inuit. I would have said she WAS Inuit. But I thought to myself, well, that's odd. Why would he use his mother in the present tense if she's dead, but then I was like, you know, everybody deals with things differently, you know, like that was how I explained it, like maybe to him you know he, I don't know. That, but that was the only red flag that I had.

[00:15:15] Will Johnson: So, he goes off to Denver, uh to the bank supposedly, in your car.

[00:15:20] Melissa Trent: He said that he needed gas for the car to go to Denver. So he asked me if he could use one of the credit cards in my car to get gas. And I said, "What credit card?" And he was like, "There's two credit cards here." And he described them to me, and one of them was my credit card, and the other one was my bank card. And I was like, "How are those in the car?" And he's like, "I don't know. They're just here." So again I gave him the benefit of a doubt and I told him that he could use one of the cards.

[00:15:45] Will Johnson: So, but in your mind at this point, he's going off to Denver.

[00:15:47] Melissa Trent: Yes, he's going off to Denver.


[00:15:53] Will Johnson: So Jeff heads down the road in Melissa's car with her bank cards, telling her that he'll be back later that day.

[00:15:58] Melissa Trent: And then at 2 o'clock he messages me and says, "Oh my gosh, traffic is terrible. I just got here." And I was like, "Okay, well hurry up and get back. I need my car." And he's like, "No problem." And then I didn't hear from him again. And I started getting really nervous, and about 5 o'clock I, I, you know I was messaging him and messaging him and around 5 o'clock he messages back and says, "Chill out. I'm in the parking lot." And I was like, "What parking lot?" And he said, "The bank parking lot." And I was like, "In Denver?" And he said, "Yes." And I said, "I need my car and I need my car right now."


[00:16:32] Melissa Trent: And then that was the last thing I heard from him. And so finally at about 8 o'clock that night I called the police, and I reported it.


[00:16:42] Will Johnson: So, when you had that conversation around 5, it sounds like maybe you knew something was up a little bit?

[00:16:47] Melissa Trent: Yes, because he was so aggressive. He was just like, "Chill" I mean I had never seen that side of him. He was like, "Chill out!" And he was like, "I'm in the parking lot." And then, you know, no communication after that. And that was so weird because he had always been... I mean we had been corresponding and texted for a couple of weeks, and he was always, you know, would always text me right back. And so I talked to some friends and told them the situation and they were like, you have to call the police. I mean this guy's obviously not up to good. And so the police came, and I told them everything, and the police really didn't think that, that he had stolen the car. They were like, "Ma'am, you gave him the keys." Like, you know, that's not a stolen car. And I was like, "I know, but he was supposed to be back here at noon, and I haven't heard from him since 5 o'clock." So the police took all of the information, and they actually called him, and he messaged them back at 3 o'clock that morning and said, "I've already talked to her. I've already told her that I'll be back tomorrow. I've just got to stay here to get this card. I'll, you know, as soon as the bank opens, I will get the, the um, the new debit card and then she'll have her car back by noon tomorrow." And so the police reported that to me in the morning and said, "He'll be back, don't worry..." blah, blah, blah. Well, I continued to message him throughout the day, and he claimed that the person that issued the new debit card wouldn't do it until 3 o'clock, so he had to stay there until 3 o'clock. I knew this was not true, and so I told him, I was like, "Take a picture. If you're sitting in that bank, take a picture." And he was like, "Are you out of your mind? If I take a picture, I could get arrested. You can't take a picture in a bank." And I said, "Then walk outside and take a picture." And he blew up at me, like "Are you questioning me? Do you not believe me?" And all this stuff, and I was like, "No, I don't believe you. I just, I want proof that you're at a bank and I want some assurance that you're going to be back here." And so supposedly he got the new credit card and was on his way back to the Springs at around 4:30 and then it started to rain, and he messaged and said that he was halfway between Denver and the Springs and that he didn't feel comfortable driving in the rain, and that um, he was turning back and going back to Denver.


[00:18:58] Will Johnson: It's around this time that Melissa finds the blog with other people complaining about Jeff. She decides to post her own experience with him, and this is when the writer, Brendan Borrell comes across the story.

[00:19:09] Will Johnson: So Brendan Borrell comes across your blog, your, your post on the blog, and gets interested. He's sort of like, you know, this is, seems like maybe an interesting story, he's a writer.

[00:19:18] Melissa Trent: Yes.

[00:19:19] Will Johnson: And he gets in touch with you and then eventually he gets in touch with Jeff himself on the run in your car.

[00:19:24] Melissa Trent: Yes. Exactly.

[00:19:27] Brendan Borrell: Basically I, I started texting him and his number wasn't, wasn't working and um, and then one morning I woke up uh, and I, I had a text message from him and I think he had, he had asked me why Outside magazine, right, was interested in him and he was very skeptical of me. He thought maybe I was, I'd been hired by the, the, his last victim, Melissa Trent, or else I worked for the cops. And uh so he was very reluctant, but as, as I sort of, I'd already begun to background him and I learned um, through my research that his mother had recently died, for instance, and um, when I told him this he, he asked me, I think sort of had developed a trust um, and he realized perhaps that he could get something from me, and also just that he did seem to have a deep need to talk about himself. And, and he was very, very transparent, which actually, you know, it made me sympathetic to him. So we began texting and, and after a while I was like, let's talk on the phone, and you know, I actually had to pay to get his phone restored so that we could chat.

[00:20:37] Will Johnson: So Jeff's now on the run in Melissa's car, texting with Brendan. And remember those bank cards he borrowed?

[00:20:43] Melissa Trent: He cleaned out my credit card and my bank account completely. Yeah, he took everything. And then took my car.


[00:20:52] Melissa Trent: Wednesday night, the cops came back, and they knew, they found him.

[00:20:57] Will Johnson: Wait, they didn't find him, they didn't actually find him, but they found out about him?

[00:21:01] Melissa Trent: Who he was, yes, they knew who he was. 'Cause he had given me a fake name. That's why, when I googled first, nothing nefarious came up about him. Um, but they found the real, he, he told me his name was Jeff Cantwell.


[00:21:18] Will Johnson: And I'm back with Frank Abagnale. The story begins with Melissa talking about how he was well spoken, articulate, and, and texted well. I guess that doesn't always, it's not always the litmus test we need.

[00:21:30] Frank Abagnale: I got really interested in this story because to be honest with you, and I hate to say it, it sounds like you're telling my story.

[00:21:36] Will Johnson: Frank, I'm glad you said it, because I was going to bring it up, but I was a little nervous and I didn't want to, I didn't want to align you with this, with this gentleman.

[00:21:44] Frank Abagnale: No, because, uh, it's just like hearing my story, only he was a lot older than me. Um, and uh, you know, I was this guy who, back then, you know, well dressed, thought of himself as a good looking young guy, and thought that I could convince people of a lot of things, about being a pilot, being a doctor, and I remember one incident of uh, going to rent a car in Italy, a little Fiat, and the lady said to me at the rental car company, "When will you bring this back?" I said, "Tomorrow," and then I kept it for six months. And I was driving through Sweden, and I pulled into a little town called Clippon, and it was a Shell gas station, a young boy came out, probably about 18, he saw the pilot's uniform hanging in the back, and he said, "Oh, you're a pilot." And he spoke great English. I said, "Yeah," so I started talking to him. He said, "Where are you going?" I said, "I'm going to Stockholm." Well, we got into conversation, he changed the oil in the car for me, and he said, "Hey, why don't you come home to my house for dinner?" I said, "Well how will your parents feel about that?" "Oh no, they're, they'd be fine, they'd love to have you." And I kept thinking to myself, I'm his age, but he thinks I'm 28 or so, and I'm actually his age. So I went home and ended up staying at his home for about 3 or 4 days and went out, he introduced me to a girl, and I went out to a dance with them. And then one evening I was out in the Fiat and got in a car accident and the Fiat was destroyed. So the next day I asked him, um, "Do you know any car dealerships?" and he said, "Yes, so my family is friends with the man who owns the Volvo dealership." So I said, "Well I might have to get a new car." So he took me by, and I asked a Volvo dealer if I might, if I could take it for a spin and try it out and of course, I was friends with the family, so he said, absolutely. And I got in the car and that car ended up back down in France, which six months later then they had to come back and get it. I think when you do those things it's all about one day to another day. You're just living day to day and you're saying, how am I going to survive the next day, and you don't really think about, and it's very bad, but you don't really think about well, what's this do to the people that, you know, you trusted you, you took this car, you stole this car from this man. It's all about you and, you know, what am I going to do to help me move on along? And, and, and there isn't this real conscious involved, and I think when I look back on it, that's what was so scary that you would do that. And what, and what I have found is that a lot of times back when I look back at people who were interviewed after having met me and, and whether I was posing as a pilot or the doctor, you know, I'd say, well you know, those people kind of talked really badly about me, and yet I really never did anything to them. I didn't really steal anything from them. On the contrary, I gave them a lot of things. Took them to a lot of dinners, gave them gifts, uh, but then I realized that people are much more about they were deceived. It wasn't that you didn't steal anything from them, they believed you to be somebody you weren't. They thought you were their friend, and you actually weren't their friend, and they're more upset about being deceived than if you had stolen $500 from them. So, I think there's a lot to this guy's story that he's just going along in life from scam to scam, day to day, this is what he knows how to do, and he doesn't have any emotional attachment to the people he's stealing from. He just thinks, how is this getting me through another day, and he only cares about, about himself. And unfortunately, at a very young age, I was that way and uh I was able to change my life, otherwise I would have ended up living the rest of my life that way.

[00:25:11] Will Johnson: All right, Frank, uh we will return to the story of Jeff Caldwell and we can find out what happens and what Melissa does as uh things are clearly taking a turn for the worse.


[00:25:23] Will Johnson: Welcome back to The Perfect Scam and part two of our Thru-Hiker Scam story. I'm your host, Will Johnson, joined, once again by my cohost, Frank Abagnale. Frank, thanks for being here.

[00:25:30] Frank Abagnale: Hi, Will, great to be with you.

[00:25:32] Will Johnson: If you come across somebody on a dating site you like, not you, but somebody, one of our listeners, and you're interested in them and maybe want to get together with them, I mean, can you do background checks on, so what are the services that are out there that you're aware of that people can, I mean obviously you can google somebody.

[00:25:50] Frank Abagnale: Yes. There's nothing you can't find out today about someone. That's what I mean; the resources that are available at someone's fingertips today and all of the services that are available to do background checks on individuals, this is why I'm very surprised when I get a lot of emails from young ladies that say to me, "I was dating..."

[00:26:06] Will Johnson: Or men.

[00:26:07] Frank Abagnale: Men, or that were dating these people for six months to find out they were married. So you know, you then say to them, "Well, during the six months, did you ever go to their apartment?" "Well, no." "Did you ever call their home phone?" "No." "Did you ever call them at work?" "Well, no, it was always just their cell phone." Those things should raise, again, red flags where it would be very simple to go find out, do they really work here? Are they really who they say they are? Did they really graduate from this university, whatever it is the story they gave you? And again, there's nothing wrong with being skeptical. It's, it's actually an asset. You know, someone who's skeptical is simply making sure that they're doing the right thing and they're dealing with the right people. There's nothing wrong with that. I'd rather deal with someone in business who's a little bit skeptical than somebody who just takes everything they hear with a grain of salt and go forward.

[00:26:55] Will Johnson: So we don't necessarily need to hire a private investigator if we're interested in dating somebody, but you can look them up.

[00:27:00] Frank Abagnale: You can look them up and find out a lot about anybody very quickly.


[00:27:03] Will Johnson: All right, let's find out what happens with Jeff Caldwell and Melissa Trent as he was on the run in her car with her credit cards. Writer Brendan Borrell working on his next story for Outside Online has gotten in touch with Jeff and is exchanging messages with him.


[00:27:18] Will Johnson: So that must have been a little bizarre speaking to like a fugitive, somebody on the run.

[00:27:22] Brendan Borrell: Yeah, definitely it, it, it raised some ethical questions for me, for sure, because he was, he was asking for things, and it was, I think sort of we drew the line with, you know, we can pay to communicate with this, with this person but we can't help him stay on the run and that, you know, at some point he, he had asked me, "Oh can you, you know, I'm going to turn myself into my parole officer, I promise. Can you just pay for me to have a, a good hotel room tonight?" And I said, "I can't do that." And um, the cops actually call him while he was driving Melissa's car and they...

[00:27:55] Will Johnson: And he picks up.

[00:27:55] Brendan Borrell: He tells them, "I'm going to bring the car home in a couple of days."

[00:27:57] Will Johnson: Oh my gosh.

[00:27:58] Brendan Borrell: And at this point they're not really willing to, you know, go after him too far, it's, it's, you know, it's only been a 24 hours and so they give it a little bit more time, but then eventually, you know, a warrant is out for his arrest, and he just, you know he's gone AWOL and he refuses to come back. And he keeps telling Melissa, "I'm going to come back, I promise," and um, you know he doesn't cut ties with her, but, you know, for a month he was just hanging out in Colorado, not that far.


[00:28:26] Will Johnson: Brendan's not the only one communicating with Jeff. So is Melissa, but her strategy is to reel him in and hopefully get her car back and Jeff behind bars.

[00:28:35] Will Johnson: Did you eventually message or talk to him again as he was driving around in your car?

[00:28:41] Melissa Trent: Yes. We stayed in contact for about two weeks.

[00:28:44] Will Johnson: Wow. And what was that like? I mean here's someone who has completely ripped you off, stolen your money, stolen your car, and you're still communicating.

[00:28:53] Melissa Trent: Yes. I was trying, he thought that the police were not going to do anything, because the police had basically told him, you know, we know you didn't steal her car, just bring it back, and then the police never contacted him again. And so his thinking was, you know, they, they, they haven't, they don't consider the car stolen, and so he felt like he still had leverage over me.

[00:29:13] Will Johnson: So you wanted to make it seem like things could be okay, just bring back the car.

[00:29:16] Melissa Trent: Yes.

[00:29:17] Will Johnson: That you, that there wasn't a warrant, that everything was, you know you could, you could, like you could work it out?

[00:29:21] Melissa Trent: Yes, exactly, and he kind of, I think on sometimes he would believe me, but he just wasn't sure, and he kept telling me, send me money. He kept saying that he was out of gas, and that he just needed me to wire him like $50 so that he could get gas and bring me the car.

[00:29:36] Will Johnson: And did you do that?

[00:29:36] Melissa Trent: And I kept... no. I kept saying "I'm not sending you any money," um, "tell me where you are, and I'll come get the car." And he was like, "No, I don't believe that you're going to come alone, I need to bring the car to you so that I could make sure everything is cool before we can do the exchange." And so we were just, you know, I told him, "That's not going to happen, you know, I'm not sending you anymore money." And so, he would get frustrated with me, and he would go like, you know, several days without contacting me, and then he would message again.


[00:30:09] Melissa Trent: It all came to a head like almost exactly two weeks after he had stolen the car. Um, I agreed to wire him money, and he said, "You have to send it Western Union, you can't send it MoneyGram." And I said, "Why?" He was like, "Just do what I say. You have to send it Western Union." And so I got the idea that I would tell him that I had sent it Walmart to Walmart, because if I sent it Walmart to Walmart you have to go to a Walmart to pick it up. So I had myself and two other people staked out at different Walmarts, and um, when I told him that I had sent it Walmart to Walmart, he said, "Okay, well I'm about two hours away, so I've got to get there." So we waited. And right, I had been there for about two hours and my phone was running out of battery, and I couldn't let it run out of battery cause I had to be able to communicate with the other people at the other Walmarts, so I ran back to my house to get my charger, and while I was there, Jeff messaged me and said, "I'm at Walmart, but I gotta go to another one because this one's um, their, their machine is down for money." And I called the Walmart that I had been at, and their machine was down.


[00:31:20] Will Johnson: Had, were you, did you tell the police, obviously this is sort of like your own vigilante justice. Had you, were you scared, were you worried? Did you think about what you would say if you saw him?

[00:31:27] Melissa Trent: No, I was, I mean I didn't tell the police. We were going , what we were going to do was if we saw the car, we were going to block the car in with our vehicle, and then, and then call the police and have them come and arrest Jeff. That was the plan. He slipped through because, you know, he was at the Walmart that I was at, and then he went to another Walmart, and but it wasn't any of the Walmarts that we were stationed at, and he rea--, the guy told him, "This is a fake number, this isn't even a real receipt," and Jeff blew up. And that's when I admitted to him, you know, I am not, I was like, he was like, "You never sent me money!" And I was like, "You're right I never sent you money. I'll never send you another dime." And it kind of came to a head. He realized then that the whole time we had been talking, I had never intended to um, you know, to get back together with him or make things right or anything. And that was the last time we ever talked was that day.


[00:32:19] Will Johnson: But finally on July 1st, 2017, Melissa and Brendan get the news that the police have found Jeff in South Dakota.

[00:32:26] Brendan Borrell: Coming out of a bar one, one evening, um, a little bit drunk, he said he crashed in the car, he crashed out in the car. He had seen some cops and he was like, oh, you know, he crashed out in his car cause he didn't want to get caught drunk driving, but then the next day when he went in for a coffee, uh, they, they had run his license plate and they, they fingered him.

[00:32:44] Melissa Trent: As soon as he got out, he told them the truth. The car was stolen and who he was, and that he told them that he was glad that it was over.

[00:32:52] Will Johnson: And he is arrested and eventually brought back to Colorado Springs?

[00:32:57] Melissa Trent: Yes, he stayed in South Dakota for about three weeks until they could get him back to Colorado Springs.

[00:33:02] Will Johnson: And you got your car back, I assume?

[00:33:04] Melissa Trent: Yes. It was in bad shape. Um, he had gone on a craft beer tour around Colorado, and I had actually made a fake profile on the dating site that we met, so I had kind of been in contact with him through that fake profile.

[00:33:21] Will Johnson: For yourself.

[00:33:22] Melissa Trent: He thought he was talking to another girl.

[00:33:23] Will Johnson: Oh my goodness. So you, okay, all right. And uh just to see if you could attract his attention or...

[00:33:30] Melissa Trent: I wanted to see where he was. If he was in the Springs, I wanted, or if he was in Colorado, I wanted to set up a date with him and then it would be me.

[00:33:37] Will Johnson: So you set up a fake profile and then contacted him on the dating site and said, "Hey, I'd like to meet you?"

[00:33:42] Melissa Trent: Yes, exactly.

[00:33:44] Will Johnson: And he responded to that?

[00:33:45] Melissa Trent: He did, he responded, and we chatted, and he would tell me, like "Oh, I'm in Cortez, Colorado," and he told me, "I'm going on a beer fest."

[00:33:52] Will Johnson: And, and that was true? He was really, he went on a craft beer tour.

[00:33:57] Melissa Trent: He, yes, that's what he called it, and when I got my car back, there were stickers from every single craft beer place that he had visited around the state.

[00:34:06] Will Johnson: Well one thing you can do when you're on the run is go visit craft breweries.

[00:34:10] Melissa Trent: Yes, exactly.

[00:34:12] Will Johnson: Oh my goodness. Well, and there's plenty of those in Colorado, there's a lot of good craft beer, right?

[00:34:15] Melissa Trent: Yes. Yes, we have, it's a big thing here in Colorado.

[00:34:18] Will Johnson: Right, right, right.

[00:34:19] Melissa Trent: And the car was, I mean he had literally lived in the car, and he kind of had it separated into sections. The front was where he had all of his personal papers, um, everything, like birth certificates, um, court documents, everything. Um, and then he also had like his toiletries up there. And then the middle section, the back seat, that was where he slept. He had like foam laid out, and he had sleeping bags and pillows, and then in the trunk, that's where he had um, his camping gear, there was rotting food, pots and pans, that kind of stuff in the trunk of the car.

[00:34:55] Will Johnson: There's sort of a, a sense of um, why did he do all this because, I mean to me, I had that question. Obviously, he was able to get a little cash from you, but that wasn't going to go a long way. He now had a, a car to get around in, but he wasn't, it wasn't like he was driving far away. He could have almost like stayed in your house for a few more nights.

[00:35:14] Melissa Trent: I think that he was just tired. He felt like he was never going to be able to get ahead, nobody was ever going to give him a decent job, and that he was tired, and he kept saying, you know conning people and lying is no life. I hate living this way. And I think that he really wanted to get arrested on purpose because you have, you know, you have everything taken care of. You've got room and board and meals and, you know, you're not, you know everybody in, in jail is bad, so you're not like the bad guy. That's what I think. That's the only thing I can figure, but he figured he would have, you know, a really good summer before that happens.


[00:35:51] Brendan Borrell: You know he can go through the motions of, of being a person or being in a relationship but he, you know, he's missing some, some deep way of making a connection with people and, and he seems to um, freak out whenever he gets too close to somebody honestly.

[00:36:06] Will Johnson: Along the way did you end up feeling some, some empathy for this individual?

[00:36:10] Brendan Borrell: You know I was; I was warned about this. I, I talked to um, uh sort of an expert in, in con artistry, and uh I mean it's, that this is, this is their deal. This is how they work is eliciting sympathy and eliciting empathy, and it's like you talk to the person and yes, you feel sorry for their predicament, but then when you, you look through their history of emotional um, violence that they've inflicted on people and the hurt that they've caused, and the fact that it's something that's been repeated year after year after year for 20 years, like when they say, you know, I'm going to turn over a new leaf, I'm, you know, this is, this is a, a new starting point. I'm going to, I'm not going to do this anymore, you, like I don't feel any sense, like I would never trust this person.


[00:37:01] Will Johnson: As I hear this story and we talk about it more, you get the sense that you don't know what his motivation is or what's driving him or bringing him down or what kind of past he's had, but there's an unhinged nature to a lot of what he's doing.

[00:37:16] Melissa Trent: Yes. Exactly. I mean really the only thing that I know about his past is what Brendan dug up and put in the article.

[00:37:23] Will Johnson: Will: When you got your car back and it's, and it's in that condition and you, and, and he had been pretty aggressive, and he had stolen money from you, after all that, uh, I can't imagine you had any good feelings, or not good feelings, but any sort of sense of forgiveness or empathy for this guy. What were you, what were you feeling?

[00:37:40] Melissa Trent: I was very, very angry.

[00:37:42] Will Johnson: Jeff lied to you, took advantage of your relationship, stole your car, your credit card. It sounds like an emotional roller coaster for anyone. As you look back on the experience with a bit of distance now, what are your feelings about Jeff and what happened? Is it harder for you to trust people in general or meet new people?

[00:37:58] Melissa Trent: It is harder to trust people, but I'm not sure that that's a bad thing. Obviously, I was too trusting, and I should have never put myself or my kids in that situation to begin with that early on. So I've learned a lot from it. And really, I feel sorry for Jeff. I, you know, I, I think, I believe that there's good and bad in everybody. And something happened to him that, that made him take this path.

[00:38:26] Will Johnson: Jeff was sentenced in June of this year. He plea-bargained and is now living in a halfway house in Colorado. His sentence is for six years.

[00:38:35] Will Johnson: What would you say to Jeff? He's a, he's a, I mean there's lots of words that I imagine could be used by you or other victims to describe him, but is there anything you could, you would say to him if you saw him today?

[00:38:50] Melissa Trent: Yeah, I mean, one of my best friends, we talk about this all the time, like I would say to him that had he just been honest with me from the beginning, I'm a very open-minded person, and had he been honest with me about his past and been honest about, you know, the life that he was living, I probably would have, you know done anything to help him and save him from that life and turn it around. And, you know, he didn't have to do what he did. It, you know, it certainly did not have to come to that at all.


[00:39:24] Will Johnson: Brendan Borrell sees Jeff as someone who took advantage of a community where people are likely to help out a stranger. But Jeff's crimes were always relatively minor. The question for him remains, why lead such a life for so little payoff?

[00:39:37] Brendan Borrell: I mean the thing about the, the outdoor community especially is there is this um, you know, sense of kindness and, you know, people who are traveling, it's like, you know, you want to help somebody out that you see on the street and it's, you know, Caldwell, you know, began where, you know, he, he was looking for, you know, he was looking for relationships and he was looking just for food, and uh this became a, a strategy for him that, that somehow worked, and he never really went beyond that. He never went beyond just the, the quid pro quo of what can you do for me? Um, I'll be nice to you if you give me something. You know the actual things that he was convicted of were never, you know, more than a few hundred dollars. The, the biggest uh, theft was, you know, charging $800 on someone's credit card at a, at an outdoor gear store, um, and certainly there was, there was more than that, but he never really like fully took advantage of people. He just would always take enough to survive or what he needed for the next couple weeks, um, which was, which was, which was interesting to me.


[00:40:46] Will Johnson: And I'm back with Frank Abagnale. Frank, uh, Melissa mentions at one point in this story, I'll go back to the beginning of this uh, this episode, and she mentions blocking his car in potentially and calling the police after. I wouldn't recommend anybody necessarily do that. She was going to drastic steps at this point to find her car and maybe get her credit cards back.

[00:41:08] Frank Abagnale: I would say that she did the right thing in trying to track her car down, but once she found her car, that's where she should have called the police and let them handle it. You don't want to start getting yourself in a situation because someone like this sometimes could turn out to be also someone that's violent, so you, you let the, let law enforcement handle that. So I would have pulled up, saw the car across the street, notified the police, kept my eye on it in case he came out, but I wouldn't have tried to block him in and do that 'cause you never know what someone might do.

[00:41:36] Will Johnson: When, when he's on the run in Melissa's car, the writer, Brendan Borrell uh begins texting, uh with, with Jeff Caldwell and communicating uh that way. Um, and, and it's a really fascinating dynamic. I was kind of reminded of, of you being on the run and Carl Hanratty, not his real name, but in, in the movie, and having a relationship with the person who's running after you. The writer wasn't trying to track down Jeff, in some ways he was, but he was more approaching it as a journalist. But there was this odd relationship.

[00:42:09] Frank Abagnale: Yeah, and I think uh, I think Jeff, Jeff kind of uh, was, his ego, he liked the fact that this writer was uh asking him questions and following up with what he was doing. I think that was just feeding his ego, so he didn't look at him as a threat or worrying that he was going to track him down or, or arrest him.

[00:42:29] Will Johnson: He eventually talks about going on a, when he's off in her car, he doesn't talk about it, Melissa explains that he went on a brewery tour, too, so there is some uh, whether it's ego or psychology there that just seems, as you said, sort of going day to day, maybe not...

[00:42:45] Frank Abagnale: Yeah, and again, that's all it is. I mean this is somebody who's living this out day to day and always thinking about what am I going to do the next day? But by the same token, while all this is going on, they're living their life and going out. They like touring breweries, so he went to look at breweries. I mean...

[00:43:00] Will Johnson: Life is normal.

[00:43:00] Frank Abagnale: Yeah, life is normal to them, and they're just going on and then they'll need money again, they'll try to figure out how the next scam to get that money.

[00:43:06] Will Johnson: I want to thank Brendan Borrell uh writing, in this case, for Outside Online magazine, also Melissa Trent telling us the story of Jeff Caldwell. Thanks to you, Frank Abagnale.

[00:43:14] Frank Abagnale: Thank you.


[00:43:17] Will Johnson: All right, well up next, we are joined by Kathy Stokes. She heads up The Fraud Watch Network here at AARP. Nice to see you.

[00:43:24] Kathy Stokes: Thanks for having me, Will.

[00:43:25] Will Johnson: All right, so Kathy, uh tell us what we've got going on? There's a, a current scam involving the AARP and we hate to hear that.

[00:43:32] Kathy Stokes: Yeah, yeah.

[00:43:32] Will Johnson: We don't like it at all.

[00:43:33] Kathy Stokes: No, we don't like it at all, and we found out quickly and we're trying to communicate it to as many people as we can, but there are scammers out there and they're either using telephone or email, and they're contacting people saying that they have won the AARP Sweepstakes and all they have to do is send some money in so that they can claim their prize.

[00:43:51] Will Johnson: All right, classic.

[00:43:52] Kathy Stokes: Classic.

[00:43:53] Will Johnson: A bunch of red flags.

[00:43:53] Kathy Stokes: A bunch of red flags.

[00:43:54] Will Johnson: And it's a, so they, they've won money, and it, you said it's a phone call.

[00:43:58] Kathy Stokes: It's a phone call, it can be an email as well.

[00:44:01] Will Johnson: Okay. So tell us more. How much have they won, supposedly?

[00:44:04] Kathy Stokes: In the case of the one that I have from one of our um, members, she actually sent it to us, that her letter was saying that she won 4.3 million dollars, and it came with...

[00:44:15] Will Johnson: That is not a small amount of money.

[00:44:17] Kathy Stokes: It came with a, our AARP logo on it, it has a Federal Reserve System logo on it, and it had all kinds of uh pieces attached to it. One was from Bank of America, um, and it looks like the other one has a, has a BBB seal on it. Um, it makes sure to tell the person that the total cash prize of 9.8 million dollars was shared among three lucky winners. Um, and for security reasons, this is really important, you're advised to keep your winning information confidential until your claim is processed, and your money remitted to you in whatever manner you deem fit to claim your prize.

[00:44:59] Will Johnson: Now I'm, I am surprised, I have to say, by the amount of money that they're offering, because you hear about sweepstakes, but that's just a, a huge sum.

[00:45:06] Kathy Stokes: We actually um, foiled one recently.

[00:45:09] Will Johnson: Wow. Do tell.

[00:45:10] Kathy Stokes: We had a, our Connecticut state office has The AARP Fraud Watch Network activities going strong there, and they have a relationship with a regional bank, and they went into the bank to do a presentation about how to prevent becoming a victim of scams, and the teller that was in the, in the bank that day was listening as she was doing her work, and it caught her ear and maybe 15 minutes after that presentation, a man comes up with a letter that he had received that was the Publisher's Clearing House that he had won millions of dollars and all he needed was to deposit this check for $9,437 that would cover the costs and the fees associated with it...

[00:45:52] Will Johnson: To get his stuff.

[00:45:53] Kathy Stokes: To get his prize. And she said, "I think that's a scam." And she started talking about what she had heard in the presentation, and he absolutely refused. He said, "Nope, this is my money." She had to get a manager involved. It took them about a half an hour, but they finally convinced him...

[00:46:07] Will Johnson: Good for her.

[00:46:07] Kathy Stokes: ...that it was a scam.

[00:46:09] Will Johnson: The frontlines, that's where it happens.

[00:46:11] Kathy Stokes: The frontlines.

[00:46:11] Will Johnson: And she heard it from an AARP seminar, in the bank.

[00:46:13] Kathy Stokes: In the bank.

[00:46:14] Will Johnson: And as you know, we did a whole episode about a fake Publisher's Clearinghouse letter.

[00:46:17] Kathy Stokes: Yeah.

[00:46:18] Will Johnson: And as we know, they will not send a letter asking you to send in money to claim your prize.

[00:46:22] Kathy Stokes: Yes, that is a BIG red flag.

[00:46:24] Will Johnson: All right. So, uh we digress. Back to the sweepstakes, AARP is not running any sweepstakes.

[00:46:29] Kathy Stokes: Well, AARP does run sweepstakes. But we do it in a much different way. Um, we will never tell you you've won a sweepstakes if you've never entered an AARP sweepstakes. If you have entered one and won, you will notified. You will have a specific person to follow-up with to uh to claim your prize.

[00:46:48] Will Johnson: Okay. So it could happen that you win some money through an AARP sweepstakes, but you will not get a call or an email or rather a letter out of the blue saying you've won a bunch of money and you need to send in money.

[00:46:58] Kathy Stokes: Right, and we'll never ask you to keep it confidential.

[00:47:01] Will Johnson: Right. Another red flag.

[00:47:02] Kathy Stokes: Yeah.

[00:47:02] Will Johnson: All right.

[00:47:03] Kathy Stokes: We actually heard from some colleagues over at the National Consumers League that they're being used this way, too. And so they're trying to communicate to their folks, we're trying to communicate to ours, and trying jointly to, to get the word out and maybe because the IRS Tax Scam is really being tamped down, people are getting more and more aware of that, that that's kind of a, a lost cause right now, and so they're looking for other ways to um, authenticate what they're doing, so they're looking at public interest groups.

[00:47:33] Will Johnson: Well yeah, they do move on to the...

[00:47:34] Kathy Stokes: Yeah, they do move on.

[00:47:36] Will Johnson: All right, well really important that you mentioned this one. Thanks for bringing it to our attention and please keep us posted on anything else you might hear about.

[00:47:42] Kathy Stokes: Will do.

[00:47:42] Will Johnson: All right, Kathy Stokes with The Fraud Watch Network here at AARP.

[00:47:47] Will Johnson: And a reminder to our listeners; for more information and resources on how to protect yourself from becoming a victim of a scam, visit AARP's Fraud Watch Network website, Thanks to my team of scam busters; Julie Getz and Brook Ellis, and audio engineer, Steve Bartlett, and audio mastering done by Julio Gonzales. For AARP - The Perfect Scam, I'm Will Johnson.

[00:48:20] Michelle: Everyone loves to hear about how a con man operates, right, how they manage to get by from scam to scam. It seems like Jeff was already at the end of his decades' long hiking trail of deception, and was relieved to be there. It remains to be seen if his next path in life is the straight and narrow. Thanks for joining our excursion into the scam files, and we can't wait to bring you our new season with more outrageous scams than you can shake a hand-whittled hiking stick at starting July 24th. We will see you then.



AARP’s Fraud Watch Network can help you spot and avoid scams. Sign up for free “watchdog alerts," review our scam-tracking map, or call our toll-free fraud helpline at 877-908-3360 if you or a loved one suspect you’ve been a victim.

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