Caleb Flynn's Phone Was Empty and He Had a Reason For It

Tony Brueski (0:01)

This is HiddenKillers Live with Tony Brueski and Robin Dreeke.

Tony Brueski (0:09)

Well, if you've been following along in the Caleb Flynn case over the last few days, you probably found some of the things we've talked about. Welcome back to the Shitshow. There's a lot. Last few days, we've of course been talking about Leah Botner, the lover, the mistress. And all of her messages as they went through 107,000 text messages and reading them aloud. Then after that, well, they decided to show some more video of Caleb Flynn. This time more fun interactions, this time with the police, this time at 428 in the morning, sitting across from Detective Mike Morgan.

Didn't quite know exactly what they were going to ask him yet. Had to have his story ready to go. Had to have it make sense. You know, things that Caleb's not good at. That's what we're going to be getting into today on the program. I'd love for you to drop your thoughts, your questions in the comment section. Substack YouTube, the places to do that. Joining me to help break all of this down as always, Robin Dreeke, retired FBI special agent, chief of the Counterintelligence Behavioral Analysis Program and master class instructor. I've been simmering on this case all weekend. I've been watching more stuff and it just keeps, I don't know, it's getting worse and worse every time I dive into it. And one of the things, I want to get your reaction to this, because it's not in our clips here today, but it's something that I just, I knew about it. I don't know why it didn't resound with me stronger until I just did it in a monologue a few minutes ago. It looks like it didn't turn out, it didn't happen the way we thought it would.

That was a line from Caleb to her, when they're at mom's house, Ashley's mom's house, the dead woman's mom's house, his wife's house, the woman who he's having the affair with is there, and he's whispering, looks like this didn't happen the way we thought it would.

I mean, what the hell are your thoughts on that one, Robin? Is that just like, does he think they're both in on this? Or does he think he's throwing a ruse her way that, wow, this, look at the convenience. Somebody happened to come in and murder her, did us a favor. You know, like, how do you read that?

Robin Dreeke (2:34)

Double entendre.

I really, I took it to read both ways, like an insider thing that only they would know at the same time, maybe hinting at what he did. It's really hard to know what was going on in his mind. And when he decided to move away from divorce and into the world of killing, and I think that statement right there said it as well, because that's not the way we thought it was gonna turn out, because maybe that wasn't the way he was planning on it. I really, because he's such a milk toast, because he is so anti-confrontational, because he likes to crawl up in a ball on the floor and cry when things don't go his way, and his mommy's there to bail him out, I really wonder at what point he was really thinking about confronting, not just his wife, but really his father-in-law. To me, this wasn't about Ashley as much as it was about confronting the father-in-law and the brother-in-law and saying, I don't want your money, I don't want your daughter, and I'm going to walk away from this all to go with this 22-year-old. I really think that thought was too hard for him to absorb because he's so anti-confrontational that he took the, in his own mind, the coward's way out. I think I'll just kill my wife by shooting her in the back of the head while she's asleep. Yeah.

I really think, because we haven't seen him play things forward. We do this all the time on the show, and that's what people with massive empathy do and someone to kill someone doesn't have empathy. So there's somewhere else on that psychopathy scale, right? We play things forward. I do it with my kids all the time. I do it with people in my life all the time. I do it with myself all the time. And we were just doing it today, you know, about your wife's wonderful art channel for kids. You know, where you take an action or you imagine an action and then you say, all right, let's fast forward this a couple of steps and see what the result will be. See what the, see what the, what will happen if I do just this, run these hypotheticals in your mind. So that way you can, before you do something good or stupid, you can back it up and say, all right, now let's run this hypothesis and run that one forward. And so we run in multiple things and then you can logically choose a path forward that makes the best sense for everyone involved. He doesn't do that. He just acts, at least from what we've seen, from what's been testified so far, he's just, he's just in the moment or maybe about one step ahead with about one marble rolling around upstairs.