Caleb Flynn’s Messages Met His Interrogation in Court

Tony Brueski (0:00)

This is The Big Breakdown, a long look back at some of the biggest stories we're covering for you at the Hidden Killers Podcast and True Crime Today. This is Hidden Killers Live with Tony Brueski and RobinDreeke.

Tony Brueski (0:18)

Oh my goodness, it's been a week. It's been a week watching the Caleb Flynn trial, seeing Alleigha on the stand, hearing more and more about the depravity of Caleb and his just horrific feelings towards his wife. Ashley Flynn was shot twice in the head while she slept, and prosecutors say the man who did it was her husband, who then told 911, an intruder broken. The jury already knew he'd been calling his wife douche for a year. On the second morning of his girlfriend's testimony, they heard what came next. He stopped saying he wanted Ashley dead and kind of started saying, how?

Joining me to break down all of this, and we're going to go through some of the testimony, the damning testimony. Robin Dreeke, retired FBI special agent, chief of the counterintelligence behavioral analysis program, master class instructor, and Jennifer Coffindaffer, retired FBI special agent. Let's begin with a clip of Caleb, where he's talking about, this is being read by Alleigha.

This is where it kind of goes from, I wish she was dead, to Adelson type territory. Let's take a look and then we'll discuss on the other side.

SPEAKER_3 (1:38)

I said on June 12th, 25, I need you.

Robin Dreeke (1:42)

Next message.

SPEAKER_3 (1:44)

Caleb said please hire someone to take Douche out. I need you in my life. I need you.

Robin Dreeke (1:49)

Next message.

SPEAKER_3 (1:52)

I said, so tempting.

I can't live without you. I've had this thought so often lately. How do we figure this out?

Robin Dreeke (2:04)

Next message.

SPEAKER_3 (2:06)

I said, I genuinely can't picture my future any other way.

Tony Brueski (2:10)

Next message.

SPEAKER_3 (2:11)

It makes me sick imagining it with anyone else.

Tony Brueski (2:14)

Next message.

SPEAKER_3 (2:18)

He said, Oh my gosh, I love you.

Caleb Flynn (2:30)

50,171.

SPEAKER_3 (2:40)

I said, on June 12th, 25th, life with you and loving you is so easy and just makes sense. I've fallen so madly in love. I don't want to settle for anything less.

Robin Dreeke (2:50)

Next message.

Caleb Flynn (2:51)

Number one, do you?

SPEAKER_3 (2:54)

He said, we have to get rid of Douche. I need you. You're my everything.

Robin Dreeke (2:59)

Next message.

SPEAKER_3 (3:00)

My heart and soul, he said.

Robin Dreeke (3:03)

Next message.

SPEAKER_3 (3:04)

He said, my best friend, my love, my better half.

Robin Dreeke (3:07)

Next message.

SPEAKER_3 (3:09)

I said, I don't even want to say this in a joking way anymore. We need a solution, Caleb. We need it to be me and you forever and no exceptions.

Robin Dreeke (3:16)

Next message.

SPEAKER_3 (3:17)

He said, I've never joked about it.

Robin Dreeke (3:20)

Next message.

SPEAKER_3 (3:21)

He said, I love you, baby. I love you so much.

Tony Brueski (3:25)

That's going to be the moment in the mini-series where it cuts to the commercial break on Lifetime, where it's like, I was never joking about it.

That's how it's going to go. They're talking about love and life and how much it's going to be great, and God, and Douche, and how they're going to kill somebody. It's a cacophony of all the emotions right there. How seriously do you take that hire someone to take Douche out? This feels like grooming to me, which it is, of slowly just kind of inserting this idea out there. He's not getting super specific, but hire someone to take Douche out is certainly an escalation from, I wish she was dead. Jen?

Jennifer Coffindaffer (4:17)

Yeah, you know, it's an evolution. We can see it in the text messaging, the thousands that exist. You can just see how it climaxes, and ultimately so sadly ending up in Ashley's, with Ashley being dead, I believe.

But nevertheless, her culpability, I think, is really only limited to her absolute immorality, and we just don't have overacts that line up with some of the words that are said.

Robin Dreeke (4:49)

Yeah, I could tell you, because, you know, I've been following you on X with this, and Bob, obviously, and he's kind of surprised. I might be even jumping ahead, Tony, I apologize, but I'm really curious on this culpability of her, because I've really, these couple of last cases we followed on, I've been watching on court TV, you know, understanding the context of both sides has been really paramount on this, because when you're sitting there just listening to the prosecution go into her side of, you know, just saying what she said and all these clips are listening to was one thing, like, oh my God, it was all him grooming her. And then when you listen to defense, give the context that her text messages were twice as much as his in that hundred thousand. And she said, yep. And then you listen to how she was pressuring him. You're getting this whole other side, which made me say, oh, shit, why isn't she being charged with something? Or why didn't they do more here? Because that's my question to you, Jen. So when you're looking at this from that optic, why do you think they didn't look at her more at the onset or even maybe now, just from what we're learning, just from the testimony she's been given?