True Crime with Kendall Rae
True Crime with Kendall Rae

Caleb Flynn Found GUILTY... Deep Diving The Ashley Flynn Murder Trial

October 8, 2026

AI Summary

5 min read

On February 16, 2026, Ashley Flynn was shot twice in the head while she slept in her bed in Tipp City, Ohio. Her husband Caleb, a music pastor and former American Idol contestant, called 911 at 2:31 AM claiming an intruder had broken in through a side garage door, stolen a handgun from his truck’s center console, and killed her while he was sleeping in their daughters’ bedroom. The story unraveled almost immediately. By February 19, Caleb was arrested. By late September, a jury took less than three hours to convict him on all counts, including aggravated murder. The trial revealed not just a staged crime scene, but a year-and-a-half-long affair, over 100,000 messages between Caleb and his mistress, and a trail of digital evidence that contradicted every part of his account.

The affair and the motive

The prosecution’s case rested on a simple argument: Caleb killed his wife to be with his mistress, Aliyah Bottner, a worship leader at their church, Christian Life Center. He also stood to lose his $200,000-a-year job at Ashley’s father’s commercial flooring company if they divorced, and he wanted to maintain his standing in the church and avoid losing custody of their two young daughters. The affair had been sexual since May 2024, and the two communicated constantly through encrypted apps like WhatsApp and GroupMe, deleting messages daily out of fear of being caught.

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What you'll learn

  • 1 (01:06) **Episode Introduction & Case Summary** - Kendall Rae introduces the episode as a day-by-day breakdown of the Caleb Flynn murder trial, following her original case coverage from July 2026.
  • 2 (07:21) **Opening Statements: Two Competing Explanations** - Prosecution and defense lay out their narratives, with the state arguing Caleb killed Ashley to be with his mistress and keep his job, while the defense claims the affair doesn't prove murder.
  • 3 (17:48) **Day One: Scene Visit & First Witnesses** - Jurors visit the Flynn home, then hear the 911 call and testimony from first responders describing the scene and Caleb's initial story.
  • 4 (22:57) **Day Two: The Staged Scene & Lack of Foreign DNA** - Testimony focuses on the side garage door being staged from the inside, the absence of a foreign DNA profile, and the defense's pushback on forensic gaps.
  • 5 (33:50) **Day Two Continued: The Search for the Murder Weapon** - Detective Adam Bernard details the extensive but fruitless search for the murder weapon, while the defense highlights the lack of a purchase record for Caleb's gun.
  • 6 (39:50) **Day Three: Family Testimony & The Financial Motive** - Ashley's mother, father, and sister provide emotional testimony, revealing the strain in the marriage, the shocking 3 a.m. phone call, and the financial stakes of Caleb's job.
  • 7 (59:31) **Day Three Continued: Financial Records & No Foreign DNA** - Tip City PD Captain Tony Smith reveals Caleb's snooping on his mistress's Instagram and the life insurance policy, while more agents confirm no foreign DNA was found.

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Guests on this episode

Caleb Flynn

Show Notes

In February 2026, 37-year-old Ashley Flynn was found shot to death inside her home in Tipp City, Ohio, after her husband, Caleb, called 911 claiming an intruder had broken in. But months later, Caleb was standing trial for Ashley’s murder. Over several days of testimony, jurors heard about a secret affair, thousands of text messages, a missing gun and evidence prosecutors said showed the supposed break-in had been staged. Now, a jury has found Caleb guilty of murdering his wife. In this episode, we take a deep dive into the evidence presented at trial, the arguments from both sides and the final verdict itself. 

If you’re unfamiliar with the case of Ashley Flynn, please check the back catalogue for my original episode from July 9th, 2026.

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