What Caleb Flynn Begged His Mistress to Do About Ashley

Eight months before Ashley Flynn was killed, Caleb Flynn sent his girlfriend a request. Alleigha Botner read it aloud in his murder trial, along with her answer, and it's the message this episode is built around.

Retired FBI behavioral analyst Robin Dreeke and 25-year FBI veteran Jennifer Coffindaffer join me for three clips from Botner's second day on the stand. June 12, 2025: the request, her reply, and his "I've never joked about it." July 4: "please take her out," "I'd have a smile on my face the whole time," and "not even for a second" when she asks whether he'd miss Ashley's parents, the same people he worked for every day. August 22: the 4 a.m. message about "ways to kill her and not go to jail," and the part that didn't make the headlines, that he'd driven past her apartment half a dozen times and sat across the street from her job weeping.

Caleb Flynn is charged with aggravated murder in the February 16, 2026 shooting of his wife in their Tipp City, Ohio home. Prosecutors say he shot her while she slept and called 911 claiming an intruder had broken in. His lawyers say the state is trying an affair, not a murder.

The panel works the line between a man who vents and a man who decides, and where in these three clips he crosses it, if he does. Parts two and three cover what she did with those messages and what the defense did to her on cross-examination.

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This publication contains commentary and opinion based on publicly available information. All individuals are presumed innocent until proven guilty in a court of law. Nothing published here should be taken as a statement of fact, health or legal advice.

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