What Caleb Flynn’s Phone and Apple Watch Revealed the Night Ashley Died

SPEAKER_1 (0:01)

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

Tony Brueski (0:08)

This time, we're going to be talking about in our next segment, the sheer arrogance of Caleb Flynn's digital footprint. Because I think that, I mean, it's been in our face the whole time. But it is just really stunning that this buffoon, with that, come on, there's a large brain here. There's a lot of space. There's a lot of depth.

Robin Dreeke (0:31)

There's a lot of place to go. There's a big walnut up there. That's about it.

SPEAKER_1 (0:33)

It's a big walnut.

Tony Brueski (0:35)

Maybe this could be looked at someday, and it might get me in trouble. I shouldn't put that in writing. But it didn't. It's absolutely mind-blowing that in today's world, the guy actually thought he could plan a brutal murder via text message and then just delete his way out of it. Oh, hello, girlfriend says, according to ChatGPT, you just press delete there. Oh, wait, it doesn't work that way.

Let's talk about how his own cell phone became the ultimate star witness for the prosecution and why killers still think they can somehow outsmart the technology. Bob Motta, Defense Attorney, is with us along with Robin Dreeke, retired FBI Special Agent, Chief of the Counterintelligence Behavioral Analysis Program and Master Class Instructor.

It always blows my mind when we see these sort of cases where someone leaves the massive, glowing, digital trail of their crimes. Guns gone, they somehow got that to not be found and never left the house. But hey, all this is here, never thought they're going to look at that. What is it about the psychology of a guy like Caleb that makes him so incredibly arrogant that he actually believes he can outsmart the cops, the FBI and modern technology? As a defense attorney Bob, you've dealt with a lot of people who think they can outsmart things. What the hell is it with some of these people that they just seem to, I'm going to do better than they're going to, no matter what.

Bob Motta (1:56)

Tony is Forrest Gump's mom, always used to say, stupid is a stupid dog.

I mean, look, I don't know, man. Maybe the dude's a total Luddite. You know what I'm saying? Just a complete and total Luddite. He doesn't understand technology at all. You got the sense from Aliyah that she understood that this guy was pretty thick when it came to tech. He's like, all right, man, there's this thing, they call it the cloud, right? So when you delete your shit, you've got to make sure that you go up and check your settings in the cloud. And he's like, is that where God lives?

Tony Brueski (2:38)

By the angels? Are the angels working in the cloud?

Bob Motta (2:42)

He did not, he just did not get it. And for whatever reason, I just think he's just a really, really, for as large as his eight head is, he's just a stupid, stupid man.

Robin Dreeke (2:56)

If you all ever saw Land of the Lost, the walnut brain, there it is.

Holy shit. He's got a walnut for a brain, there it is.

Tony Brueski (3:11)

You have the mountain of cell phone data, the text messages, the location pings. I mean, everything is there being tracked, including his movements that night, including her movements that night. I mean, there's digital shit everywhere. Does he think these things are just like the old Casio watch from the eighties with the calculator on and the most they're gonna do is addition and subtraction?

Bob Motta (3:34)

He reminded me of my father. My father uses his iPhone for three things.

Robin Dreeke (3:39)

He has an excuse, he's old.

Bob Motta (3:42)

But this guy has an excuse. He spent like every free waking moment of his life that he was with his wife and kids trying to pretend like he was a good husband and father.

Robin Dreeke (3:53)

400 texts a day with some stranger.

Bob Motta (3:57)

300 texts a day is not a fucking affair that's a full-time job, bro.

Robin Dreeke (4:02)

I like that.

Bob Motta (4:03)

He was not doing much death scrolling, you know, I'm going to do scroll for a few. Like this guy had no idea about the tech. He was way too busy trying to plot his new life and trying to figure out how to end his old one. And he just wasn't getting into his, as Robin likes to say, the granular part of this plan in terms of how do I get rid of all the evidence? Like that was the one part that just didn't really run.