Ashley Flynn | A Secret Affair, 107,000 Messages, One Murder (Part 1)
Hosted by Derrick Levasseur and Stephanie Harlowe
- 1h 58m
- Transcript
Summary
Written by a model from the transcript; not yet reviewed.
In February 2026, Ashley Flynn was shot and killed inside her Tip City, Ohio home, which she shared with her husband Caleb and their two daughters. Caleb initially told investigators that a burglar broke in and killed his wife. However, police soon uncovered that Caleb was living a double life and was heavily involved in a secret, intense affair with a younger woman named Aaliyah Botner, a fellow worship leader at their church. Over a twelve-month period through a GroupMe account alone, Caleb and Aaliyah exchanged over 107,000 messages, frequently discussing their hatred for Ashley and how much they wanted her gone. The case exposes a dark narrative of betrayal, manipulation, and greed, as Caleb stood to inherit wealth and maintain his position in a thriving family business while wishing death upon the devoted wife who had supported him for fifteen years.
- Ashley Flynn's parents and family were deeply integrated into Caleb and Ashley's daily lives, providing regular financial support and including Caleb in family vacations. 10:48
- Caleb Flynn and his mistress Aaliyah Botner exchanged over 107,000 messages on GroupMe alone between February 2025 and February 2026. 1:10:24
- Ashley discovered evidence of her husband's infidelity on an iPad in October 2024, prompting her to attempt to contact Aaliyah Botner directly. 57:13
- Caleb frequently texted Aaliyah expressing his hatred for Ashley and explicitly stating that he wanted his wife dead. 1:22:01
Chapters
- 0:00Episode Introduction and Host Greeting
Hosts Stephanie Harlow and Derek Levaser welcome listeners and set the stage for the Ashley Flynn case.
- 0:43Caleb Flynn’s Career and Family Integration
Caleb’s pastoral work, business role with Richard Smith & Sons, and close ties to the Smith family are explained.
- 4:59Ashley Flynn’s Background and Marriage
Details of Ashley’s upbringing, education, marriage to Caleb, and family life are presented.
- 8:00Evidence of Infidelity and Manipulation
Text messages, social media posts, and testimonies illustrate the depth of Caleb’s deception and Aleah’s involvement.
- 10:00Financial Motives and Family Dynamics
The episode discusses how Caleb’s financial prospects and the Smith family’s support influenced his actions.
- 12:00Legal Proceedings and Testimonies
Courtroom testimonies from family members and witnesses are summarized, highlighting key points of the trial.
- 14:00Conclusion and Reflection
Hosts reflect on the tragedy, the betrayal, and the impact on the community, closing the episode.
- 29:33The Secret Affair with Aleah Botner
The hosts reveal Caleb’s affair with Aleah Botner, including the timeline and nature of their relationship.
- 48:15Affair Allegations and Moral Conflict
Hosts discuss Aaliyah’s claims of Caleb’s affair and her moral stance on the situation.
- 56:43Discovery of iPad Evidence
Ashley Flynn finds incriminating iMessage and WhatsApp exchanges on Caleb’s iPad.
- 1:10:00Aaliyah’s Manipulation and Control Tactics
Aaliyah’s attempts to control Caleb and manipulate the narrative are examined.
- 1:24:42Expressions of Hatred Toward Ashley
Caleb’s texts reveal escalating threats and hatred toward his wife, Ashley.
- 1:34:50Wrap‑Up and Sponsor Interludes
The episode concludes with sponsor messages and a brief reflection on the case.
- 1:37:46IQ Bar Snack Promotion
The episode includes a sponsor segment promoting IQ Bars, detailing flavors and health benefits.
Highlights
- 7:35
Caleb Flynn on American Idol in 2013story
In 2013, Caleb Flynn appeared on season 12 of American Idol, where he claimed on camera that music was his life and that he loved his wife more than anything in the world.
- 47:16
Aaliyah Describes the Affair's Beginninginsight
Aaliyah Botner testified that her relationship with Caleb turned romantic after he falsely told her that Ashley had cheated on him two years prior and that they were living merely as roommates.
- 57:13
Ashley Flynn discovered deleted iMessages on Caleb's iPad while he was at work, including a photograph of Aaliyah's hand with a drawn ring discussing marriage.
- 1:10:24
Investigators recovered 107,000 messages between Caleb and Aaliyah sent via GroupMe in a single year, averaging nearly 300 messages per day.
- 1:14:18
Matching Hidden Tattoosinsight
Caleb and Aaliyah got matching Harry Potter lightning bolt tattoos, but Caleb chose to place his tattoo in his armpit so his wife Ashley would not discover it.
- 1:19:08
Conversations About Deathinsight
Aaliyah testified that Caleb regularly stated he wanted Ashley to die, eventually escalating to admitting he was thinking of ways to kill her if he could avoid jail.
- 1:21:48
Text Messages Wishing for Deathdata
Recovered text messages show Caleb telling Aaliyah that he needed Ashley to die, to which Aaliyah expressed enthusiastic agreement and affirmation.
Quotes
“A secret relationship, thousands upon thousands of messages, lies, hidden accounts, deleted conversations, and a second life running parallel to the first.”
Stephanie Harlowe · 0:59 “He did not make it past the initial judge's audition. His audition was never aired and his elimination happened pretty quickly.”
Stephanie Harlowe · 9:47 “The money could be used for things like the girls' activities or music lessons, weekend trips, vacations, or other experiences the whole family would enjoy.”
Stephanie Harlowe · 17:55 “She was very manipulative, and we'll see that in the text messages.”
Stephanie Harlowe · 31:21 “She was not innocent at all.”
Derrick Levasseur · 31:24 “I never morally justified it. I just did it even while I knew it was wrong.”
Unnamed speaker · 48:29 “In October of 2024, Ashley got her first real glimpse of the relationship Caleb had been hiding.”
Stephanie Harlowe · 56:21 “The messages on GroupMe start in February, at the beginning of February.”
Stephanie Harlowe · 1:21:00 “I hate her and always will. I choose a life of solitude 100 out of 100 times over anything with her.”
Stephanie Harlowe · 1:54:03
Sponsored segments
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- Quince 1:03:42–1:06:44
- Ladder app 1:34:40–1:36:22
- Patreon 1:57:58–1:58:07
About this episode
In the early morning hours of February 16th, 2026, Ashley Flynn was shot and killed inside the home she shared with her husband, Caleb, and their two daughters. Caleb told police that someone had broken into the house, murdered his wife, and disappeared. Up until that night, Caleb’s life had been deeply intertwined with Ashley’s. They had been married for fifteen years. They were raising two daughters together. They attended church together. Caleb worked for Ashley’s father, was close with her family, and had spent years building a life that was connected to hers in almost every possible way. But investigators would soon discover that there was another version of Caleb Flynn’s life. One that Ashley did not fully see. A secret relationship. Thousands upon thousands of messages. Lies, hidden accounts, deleted conversations, and a second life running parallel to the first. And as police began pulling those two lives apart, they also began uncovering something else: the story of what Ashley had been seeing, questioning, and trying to make sense of in the months before she died.
Transcript
22,857 words · 7 speakers
Speaker names marked are inferred from speaking time and the show’s known hosts — they are not voice-verified.
Topics
- iMessage
- iPad
- C L C
- Crime Weekly
- CLC
- GroupMe
- iPhone
- Run for Christ
Page updated · transcript and summary are machine-generated