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Caleb Flynn Called Feb. 16 a Day She'd Never Forget - WHY?! artwork

Caleb Flynn Called Feb. 16 a Day She'd Never Forget - WHY?!

Hidden Killers With Tony Brueski | True Crime News & Commentary

September 28, 2026

Hours before Ashley Flynn was found dead, Caleb Flynn was telling Alleigha Botner that February 16 would be a day she would never forget. Botner testified that she believed the promised action was a divorce.

Speakers Tony Brueski, Alleigha Botner, Eric Faddis, Robin Drake

TopicsTrue CrimeNewsNews Commentary

SPEAKER_1 (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 Robin Drake.

Tony Brueski (0:17)

She gave him deadlines in October, November, December, and one last shot on January 11th. He blew every single one of them because he's Caleb Flynn. And then she cut him off. Then came Valentine's Weekend, and 40 hours after she told him she had a date coming up in March, Ashley was dead. We're going to be walking through what happened the weekend of the crime, in her words, and what a jury is supposed to do with it. We're going to start off with the day after Valentine's Day in a church in a hallway after the service.

Caleb and his mistress meet up, and there's a bit of a discussion that goes on in the hallway. Here's what happened.

SPEAKER_3 (1:02)

What did the two of you discuss?

Alleigha Botner (1:05)

He explained to me how he already had talked to her, and he told her that he was divorcing her. Who's her? That Ashley. And he said that she's not happy, but that he was going to do it.

And I said, you know, I won't believe you. You've said this so many times, and it's never happened. And I asked him, I said, are you still willing to leave her knowing that there'll be a chance that I don't, I won't ever be with you again.

SPEAKER_3 (1:36)

How did he respond to that?

Alleigha Botner (1:38)

He cried and asked me why, why I don't want to be with him again. And I told him that I don't trust him and that I'm moving on with my life.

SPEAKER_3 (1:50)

What did you tell him in a text message on February 14th regarding your future plans?

Alleigha Botner (1:55)

That I had a date coming up in March.

SPEAKER_3 (2:03)

What did, how did he respond to that information?

Alleigha Botner (2:09)

He was upset.

SPEAKER_3 (2:13)

Did he ask you not to go on the date?

Alleigha Botner (2:15)

No.

SPEAKER_3 (2:19)

What did you say would happen if he didn't act quickly in regards to even your relationship?

Alleigha Botner (2:32)

That I would never, I would never want to do it again.

Tony Brueski (2:37)

Of course, he didn't ask her not to go on the date because he doesn't do anything directly like that. It's always passive aggressive. It's always some sort of coercive controlled narcissistic nightmare that how he lives his, his life. She doesn't believe him and he cries two days later, Ashley is dead.

Is about to lose her enough for a jury to believe he killed his wife?

Eric Faddis (3:04)

It's certainly some evidence of that. It's not in and of itself, certainly not enough. But, but, you know, the jury wants to know what would be a reason this person would do this, especially based on their past course of dealing with the individuals involved in this saga. And could it be that, you know, he got sort of desperate, he got scared and insecure and saying, hey, if she's going to leave me, I got to do something drastic.

And the most drastic thing could be freeing him from his current tether to his wife in a, you know, ungodly way of homicide. And then saying, hey, look, no, now I'm all yours. You can believe me, you can trust me, I'm committed to you. And so certainly could that, combined with other pieces of evidence, provide a compelling motive to this jury? I think it absolutely could.

Robin Drake (3:52)

Yeah, it could be the door that's broken in the wrong way that they showed on the other day.

Or the non-verbals of pulling the trigger twice and saying he had a handgun in the car and his wife was shot twice in the head as he's pulling. You know, these are all these little clues. But to Eric's point, you know, I think it's the preponderance of all the data that's coming in that doesn't point anywhere else but this. I mean, it's just, you know, I think the defense is doing the best they can and they lined out, you know, that they're not denying he's a horrible human being, that he was cheating on his wife and all these things because you can't deny any of it because of this.

Tony Brueski (4:32)

And he had a plan after he heard, you know, she's going on a date and she's getting frustrated and there's a deadline. Well, he sprung into action with all this.

SPEAKER_3 (4:43)

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