Caleb Flynn's Double Life Built on 100,000 Lies
Hidden Killers With Tony Brueski | True Crime News & Commentary
September 23, 2026
Prosecutors did not have to speculate about motive. They had a digital archive. Over 100,000 text messages between Caleb Flynn and his mistress, sent over the course of months while he was still married to Ashley and still serving as the worship pastor at their church.
Speakers Tony Brueski, Robin Dreeke
TopicsTrue CrimeNewsNews Commentary
Tony Brueski (0:01)
This is Hidden Killers Live with Tony Brueski and Robin Dreeke.
Tony Brueski (0:09)
Let's start talking about the double life a little bit before we get to the gun.
The defense wants you to believe he was just a bad husband who made a terrible mistake. That's why they've been pitching it, because they don't have much to stand on. It's like, yeah, he's pretty much a douche, but it doesn't make you a murderer, which is true. But prosecutors brought in receipts, over a hundred thousand of them. We're talking about a mountain of text messages to his mistress sent while he was playing the devoted worship pastor at home. One of the most killing messages, Caleb types out, if I could literally kill her and not go to hell, I would do it in a heartbeat.
Robin Dreeke (0:54)
Let's talk about what happens.
Robin Dreeke (0:56)
I guess he bought himself an indulgence to get out of hell. Hey, it was a two-for-one.
Tony Brueski (1:03)
I got an indulgence I'm group on.
Let's talk about what happens when a secret life gets this dark. People make all sorts of comments about their spouses in fits of anger. Oh, I could kill him or her. I get people do that sort of shit. It's a choice of words I don't like to ever use.
Robin Dreeke (1:23)
No one I know, but anyway.
Tony Brueski (1:25)
I can say I've heard it over my life, but it's never like this. It's never.
Have I ever seen anybody take it to the level of, if I wouldn't go to hell, I would do it in a heartbeat. That's fucking dark. That's like, what? That's not a quip. That's not, I could kill him. That's a, oh, it sounds like you're plotting or are examining this a little bit deeper.
Robin Dreeke (1:52)
So the only thing holding you back from being an important bucket of goo is your fear of going to hell. So again, fear is a great motivator. And so somehow or other, he alleviated his fear or his unbridled urges overwhelmed his fear.
Tony Brueski (2:10)
It was just, there's several of them. I mean, we've got a bucket of a hundred thousand of them. We've only heard like three of them so far.
What? I mean, we don't know what's going to be in these these text messages, but a hundred thousand is a high number for text messages. That's a lot. What that to me when I heard that was this is a needy as hell man. I mean, I'm interested to see the dynamics of the back and forth in this, but I'm going to guess it's Caleb needing a lot of stuff, a lot of attention and a lot of reassurance. I mean, what was your reaction when you heard a hundred thousand texts?
Robin Dreeke (2:53)
Yeah. Like you said, it's a very needy human being. We haven't heard yet, at least from what I watched in the testimony, what started to go on sideways in this relationship. Because again, something went sideways, was it 21 or 22 where he switched jobs. I think something strange happened in there. I don't know quite what because we haven't been privy to it yet. But obviously, Ashley wasn't giving him satisfying that neediness of validation that he kept seeking. Again, this is one needy five-year-old. When he latched on to him, when he found another human being to give him that neediness and allowed him to text him, text them 100,000 times without telling them to piss off, that's very telling.
It boggles the mind, but yeah, there's people out there that are mad. I mean, if you're wondering what the definition of an energy vampire is, this is it.
Tony Brueski (3:48)
What I thought was kind of presented, it felt like from the prosecution standpoint, as they were trying to downplay, he's a bad husband, without a doubt, we can all agree that he's a bad husband.
Tony Brueski (4:00)
You mean defense, right?
Tony Brueski (4:02)
Defense, yeah. When they were trying, yes, when the defense was trying to sell that to the jury in openings, it also then jumped over to, he was setting these 100,000 texts to the mistress, but then, but then he jumped over and was texting Ashley all sorts of love notes and things, like, that makes it creepier, that makes it worse to me. The fact that he's, he's then jumping over there and like giving her praise and adoration while he's texting 100,000 times with his mistress, that shows some pretty creepy compartmentalization there for someone who's able to do that much.
Robin Dreeke (4:41)
Or maybe he's going down the road of FLDS and wanted more wives.
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