Why Caleb Flynn Chose Murder Over Leaving Ashley

Tony Brueski (0:01)

This is Hidden Killers Live with Tony Brueski and Robin Dreeke.

Tony Brueski (0:08)

Let's keep talking Caleb Flynn, shall we? Let's talk about Caleb himself to figure out to what was actually going on in his massive forehead, leading up to the murder. It's one thing to have a toxic affair and complain about your spouse, but it's entirely different, terrifying leap to actually plan and execute the murder of your wife, just to get out of a marriage. Really need to break down the psychology of the guy who can play the normal husband at home while secretly texting his mistress about how to get away with killing his wife. A lot of people have messy affairs and they vent about their spouse, but Caleb took it to a dark fantasy level that goes far beyond what most do. When we look at the behavior and those texts in the months leading up to the murder, what was the psychological tipping point that made him finally decide to cross that line? That's, I think, the question a lot of us have to discuss. Bob Motta, defense attorney from Defense Tyreys, and Robin Dreeke, retired FBI special agency for the Counterintelligence Behavioral Analysis Program. Bob, I'm going to go to you. What do you think it was for him in this relationship? Was there a moment where he said, I'm going to do it?

And if there is, what was it?

Bob Motta (1:20)

I don't think so. I don't think it's a point. I think it was a squeeze.

Because if you look at the text messages, they're going back to early 2025 So this was, we know it was an 18 month relationship in terms of when it started in earnest with the flirtatious text. So the real question for me is, he is out kicked his coverage in terms of...

Tony Brueski (1:52)

It's a good analogy.

Bob Motta (1:53)

Yeah. He's a 38 year old balding guy, failed American idol dude who had a dream.

Tony Brueski (2:02)

Yeah.

Bob Motta (2:03)

I had a dream. I was going to be a professional singer. Those dreams were dashed. He's left to being a singer in the church there, which I'm sure was somewhat fulfilling for him, not nearly what he had cooking up in his mind.

I'm not a star. So, you know, and he meets this young, what was she? 22 at the time?

Robin Dreeke (2:27)

20 at the time.

Tony Brueski (2:27)

20 initially, so he's 24 now, yeah.

Bob Motta (2:30)

Yeah. And you know, I think that he gets the sense that he's going to be able to hook her, you know, and I think that she sees him as an opportunity to change the arc of her life, you know, and I think that they were both seeking very different things out of that relationship. And I have come to the conclusion in my own mind that she was very much running that relationship, much like I felt with Lori Vallow and Chad Daybell. Chad just didn't have the wherewithal and mental acuity to be able to outsmart her.

And, you know, she had a goal in that relationship as well, which she was going to use him to get to. And in this situation, you know, because I kept saying to Ali, I'm like, are they having the real talks because if he divorces, the money, the job goes away. You know, he's going to have to pay child support. There's a lot of problems that are going to arise in terms of whatever she's thinking her life could be with him that are no longer going to be a part of his life. In fact, divorces are like, and it kind of goes back to our first segment a bit in terms of the reality of what was going on because out of 107,000 texts, we probably heard a thousand, right? So there's a shit ton more context there. And I'm assuming that had the defense been able to find anything that would have been more of a smoking gun in terms of Ashley, that they would have brought it out. You know, so what they have, I think is what they have. Now, I was never clear whether or not you could get into the WhatsApp and the GroupMe stuff. I don't know if that was all included.

Some of it was, but she had lost her phone and her computer. So I don't know, but trying to figure out his psychology is so hard because I just think that the guy was like, wow, I got a hot chick. You know, and it's like he's sitting around saying shit to her that he doesn't necessarily believe. He hated his wife. I don't really think he hated her. I think that he was, you know, Allison rejects the small head of the ITIS theory of defense. But I'm like, this dude, this dude was thinking with his dick all day.