Even Caleb Flynn's 12-Year-Old Saw It Coming

SPEAKER_1 (0:02)

This is HiddenKillers With Tony Brueski.

Tony Brueski (0:10)

Thanks for joining us. The word failure, I don't know that it is a ample enough word to describe Caleb Flynn. After seeing the testimony from the people who wrapped their arms around him, brought them into their lives, helped him, assisted him, gave him a path forward when his own ventures failed miserably as they seem to have consistently done.

He still felt it appropriate just to turn around to all those people who opened up their homes, their arms, their trust, their families, their daughter, too. And shit all over it.

This from the worship leader, Caleb Flynn. If you're watching this in prison, Caleb, I don't think they're watching you that close. And you're crying a lot. You know, maybe it just overtakes you. Maybe it overtakes you so much that, you know, you find an exit ramp. Because, you know, I feel like you're kind of a waste of tax dollars. And by that, I mean, it's a waste to spend whatever it is, $3.95 a day on your food.

Take that as you will.

Here's an accounting of what went on in the Caleb Flynn trial and the heartbreak, the frustration, the, I think, just viscerally deep disappointment that so many people around Caleb Flynn have because of his alleged actions. And again, all this, you know, is allegedly guilt or innocent until proven guilty, blah, blah, blah. Todd Smith brought his son-in-law into the family business for a simple reason. It just felt fair. Never a good reason to bring somebody into a business, by the way, to make it fair. You want to bring somebody in because it's advantageous. There's things they can offer your company.

But it just felt fair. His other son-in-law was already working there. Caleb Flynn had moved up to Tip City from South Carolina with a sales job that, in Todd's own words, really wasn't going anywhere. So, as a lot of parents do, they swoop in and they rescue. And I get it. I'm a parent too. I can be guilty of that at times. And it's one thing when they're young and little. It's another when they're in their 30s and there's children that are dependent on them and your daughter is in the same house as that buffoon.

And she thinks it's love. Because he told her it was. And he's very good at manipulating people. And your dad to her, your grandpa to these kids, you're like, it's hard not to step in sometimes. I'm not saying you should or you shouldn't. I'm just saying, I get it. And sometimes it works out. Sometimes those family folds, those businesses, those we're all going to be on the same team. Maybe you're a complete failure over here on your own. But under this umbrella, maybe you can thrive. That happens. I mean, it does. By 2025, that job was pulling more than $200,000 a year for Caleb. So he goes from utter failure to 200K a year. According to Ashley's sister, Kayla Keyt, who handled the books on top of that, Todd and Jill Smith had started handing out the inheritance early so they could actually watch their kids enjoy it. Check for $800 or 850, land it in the mailbox every single month with one instruction, go buy something nice for your family. Plus, the Smiths covered the lodging on all the family vacations. Caleb, my friend, you have great in-laws here. And not because they're just giving you money, but because they truly care about you. They care about your well-being and the family's well-being and their daughter's well-being. Now, that's not a reason to stay in an unhappy marriage for the benefits or the perks. But surely, the exit ramp from that relationship is not killing the daughter of the people that are giving all these things to you and everything that she's giving to you, her love, her affection, her children, her trust, her life. You know, all you can do is get on the phone really like this and make a really bad plan. And for the love of God, you're going to murder somebody. Come on, watch an episode of Dateline once. Have the slightest clue on how to stage a crime scene.

SPEAKER_1 (5:39)

Come on.

Tony Brueski (5:42)

You couldn't even. That that itself was a bridge too far for you, Caleb. But allegedly, back in August 25, Kayla sat down with Caleb and Ashley and laid out a spreadsheet. It showed that if sales kept trending up in the company, that company could easily pay him $300,000 to $400,000 a year down the road. And eventually, the entire business was going to be a gift. Todd planned to hand it over to his two daughters, 50-50, keeping nothing for himself except a consulting fee. Now, that's one side of the story. Prosecutors say the other ledger was sitting right on his phone. Prosecutor Paul Watkins told the jury, Caleb sent a message to another woman saying, I was up until 4 a.m. last night crying, literally trying to think of ways to kill her and not go to jail. He would underwrite, if I could literally kill her and not go to hell, I would do it in a heartbeat.