Caleb Flynn’s Mother Called Him a Leader — She Never Wrote Ashley’s Name
Hidden Killers With Tony Brueski | True Crime News & Commentary
October 9, 2026
Before Caleb Flynn was sentenced to life without parole, his parents filed letters asking the judge for mercy. His mother listed his accomplishments as too numerous to mention and wrote that he has repented to his Lord. His father said Caleb is not a stereotype of a criminal.
Speakers Tony Brueski, Shavaun Scott, Robin Drake
TopicsTrue CrimeNewsNews Commentary
SPEAKER_1 (0:01)
This is Hidden Killers Live with Tony Brueski and Robin Drake.
Tony Brueski (0:07)
Another aspect of this that came to light at sentencing, mom and dad, everything about the Caleb Flynn case was pointed backwards to the affair, to the messages, to the night the alleged staged burglary took place after prosecutors say he shot Ashley in her sleep. But after the guilty verdict, the question shifted forward. Who is this guy and how did he get built? Two letters filed by Flynn's parents before his sentencing may be the closest thing to an answer. His father, Mike, told the judge his son's actions were not consistent with who Caleb has always been. His mother, Kim, asked the court to consider his 38 years before what she called his recent poor choices.
That's a way of putting it. And wrote that Caleb had repented to his lord. Neither letter mentions Ashley Flynn by name, neither mentions their granddaughters. Shavaun Scott is with a psychotherapist and author to help unpack what these letters reveal about the family system behind the man and what they mean for the two girls still inside of it. Along with us, Robin Drake, retired FBI Special Agent, Chief of the Counterintelligence Behavioral Analysis Program and master class instructor. So both these letters, we've looked at them, they do the same thing, Shavaun. They build a version of Caleb, the servant, the leader, the pastor's kids, the man, the correction officer, praised because they raised such a nice, polite young man. That gets in the letter. And they hold it up like, that's, that reveals the person and everything the jury needs to see, even though they just convicted him of murder. His mother lists his accomplishments as too numerous to mention. His father says he's not the, and I love this, stereotype, two words, of criminal. Couldn't do a spell check, a bridge too far. A jury deliberated for two and a half hours after hearing 107,000 messages to his mistress. And this is how a family like this process is what happened.
How does this type of family system function?
Where the image of the person is more real than what the person actually did, the imagined image. Actually explain how someone like Caleb Flynn, does this explain how he gets built? Do these two letters do all the heavy lifting for us?
Shavaun Scott (2:38)
Yeah, yeah, I think it says a lot. And it's really this family narrative built on mythology.
And obviously, he has pulled off this self, this image, the family bought into it. He's not been held accountable because probably every time he did something naughty and was going to get in trouble for it, he'd cry and the tears would work. And, you know, or the other fallback here that we hear so much of, confess your sins and you're forgiven, it's all gone and it's all erased and that's, that's the way they're looking at it.
But yeah, they're not in reality and this is a family system that would produce a kid like this. You know, we, we always had the idea in years past that narcissistic people were from abusive backgrounds. And we know better now that sometimes that may be true, but in many cases they've been indulged, and they've been put on a pedestal as little children and told how wonderful they are. And they learn to play a role and manipulate that way and to integrate that sense of, oh, I'm special and I'm better than everyone. And that's what you see in these parents' letters. That this affair, which they don't even really address, but the horrible things that were said, this isn't the real him. This is just a little blip here, a little mistake. And he's asked for forgiveness, and so it's all gone now. It's erased. Because that's another thing with the concept of forgiveness. People interpret, you know, again, just like love, it's a word for a lot of complicated things. Forgiveness is the same way. And for some people, forgiveness means it's erased, it's gone. So there's no accountability, there's no consequences, because he's asked for forgiveness. And I think it's a healthier way to look at it, that you can ask for forgiveness. And people may see that then as, I'm not gonna spend time in my head ruminating about you and hating you. I'm just not gonna waste my life doing that. But that doesn't mean that I don't hold you accountable.
And I think his parents do it the first way, while he's forgiven, and so it's all gone as if it never happened.
Robin Drake (4:55)
So, yeah, I'm still trying to understand, and I think I got it, why, when you read those letters, just like when you watch them all in the courtroom, whether it's the parents or Caleb too, you're not emotionally connected to these people.
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