Hosted by Kendall Rae
Written by a model from the transcript; not yet reviewed.
This episode covers the murder trial of Caleb Flynn, who was convicted of killing his wife, Ashley Flynn, in February 2026. The host details the day-by-day court proceedings, highlighting the prosecution's case which centered around Caleb's long-term affair with church worship leader Aaliyah Botner, lucrative financial motives linked to his father-in-law's business, and over 100,000 text messages discussing a desire to murder Ashley. The defense argued that the investigation was flawed, rushed, and relied heavily on circumstantial evidence without a physical murder weapon or direct forensic ties.
The episode examines key testimony from family members, law enforcement, forensic experts, and the mistress herself, who admitted to exchanging graphic messages about wanting Ashley dead. Digital analysts revealed compelling health tracking data and phone activity contradicting Caleb's claims that he was sleeping during the murder. Ultimately, the jury found Caleb guilty on all counts, and he was sentenced to life in prison without parole, bringing a definitive measure of justice for Ashley's family.
A commercial pitch for Dell's latest laptops and accessories.
Promotion for the new CBS comedy series "Eternally Yours."
Kendall Rae welcomes listeners and sets the stage for the episode.
Kendall Rae summarizes the tragic murder and introduces the trial focus.
The third day features emotional testimony from Ashley's family members.
Recounting the first day of trial, including the 911 call and initial evidence.
The host promotes eco‑friendly diapers, highlighting their absorption and chemical‑free qualities.
Kayla explains how Ashley’s daughters reacted to the affair, revealing their heartbreak and support system.
Aaliyah explains her alibi on the night of the murder and the phone activity that supports it.
The prosecution reads excerpts from the 107,000 messages between Caleb and Aaliyah, exposing threats and plans.
Captain Tony Smith reveals Caleb’s financial ties to Ashley’s life insurance and his monitoring of Aaliyah’s Instagram.
Aaliyah details how her relationship with Caleb evolved from professional to sexual, including key dates and events.
The episode opens with an introduction to the case and the hosts’ overview of the Ashley Flynn murder trial.
Aaliyah reacts to the disturbing messages, expressing disbelief and disgust at Caleb’s admissions.
The conversation escalates to threats of violence and discussions about potential murder plans.
The final messages before the murder outline plans, doubts, and the last exchange between Caleb and Aaliyah.
Aaliyah’s attempts to contact Caleb and the discovery of a deleted DM set the stage for the murder’s execution.
Caleb describes his movements, sleep patterns, and the moment he heard gunshots, providing a timeline for the prosecution.
The defense focuses on Aaliyah’s emotional volatility, credibility, and alleged lack of investigation.
Investigation of the Blink camera system and testimony from neighbors and detectives highlight gaps in evidence collection.
Explicit Messages About Murderstory
Aaliyah Botner reads verbatim messages where Caleb explicitly states that if he could kill Ashley without going to jail or hell, he would do it.
Staged Break-In Evidenceinsight
A BCI special agent testifies that the damage to the side garage door was inconsistent with a forced entry and likely inflicted while the door was open.
Contradictory Health and Step Datadata
A digital forensics analyst presents heart rate and step counter data from Caleb's watch and Oura ring showing activity during the time he claimed to be asleep.
Uncovering 100,000 Incriminating Messagesdata
The prosecution reveals massive digital evidence showing constant communication between Caleb and his mistress, including daily expressions of hatred toward Ashley.
Caleb's Initial Police Interviewsstory
Audio from Caleb's police interviews on the day of the murder is played, detailing his suspicious claims and inconsistent timeline of events.
Guilty Verdict on All Countsdata
After less than three hours of deliberations, the jury returns a guilty verdict on all counts against Caleb Flynn.
“And on top of that, the story that her spineless husband, Caleb Flynn, tried to tell to get away with her murder is absolutely fucking pathetic, if you ask me.”
“The evidence absolutely did not support Caleb's intruder story.”
“The prosecution said that there are two competing explanations for what happened here.”
“The defense's position that investigators failed to consider other possibilities and that their theory, the state's, was pure speculation rooted in hollow circumstantial evidence and convenience.”
“I had to call at 3 o'clock in the morning with my wife.”
“And I even Googled, I said, can a Christian man snack and shoot his wife and kill his wife?”
“of Ashley's $100,000 life insurance policy.”
“I mean, it soon became incredibly clear that their relationship, Aaliyah and Caleb's, was riddled with toxicity.”
“On August 22nd, 25, I said, 'It would change everything, Caleb.”
“Make sure you are sure about your decision tomorrow and where in your to-do list are you packing your things?”
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. This episode is sponsored by: Quince: Find the fall pieces you’ll reach for most at Quince. Download the Quince app for app-exclusive offers, or go to quince.com http://quince.com. Get free shipping on your order and 365-day returns. Freestyle: Get 30% off your first 3 months of a Freestyle diaper subscription at freestyle.world/TCKR http://freestyle.world/TCKR with code TCKR. That's a full month of premium diapers delivered to your door for just $49/month for your first 3 months. Nutrafol: Right now, Nutrafol is offering my listeners $10 off your first month’s subscription and free shipping when you visit nutrafol.com http://nutrafol.com and enter promo code KENDALLRAE. Hiya Health: I’ve worked out a special deal with Hiya. Receive 50% off your first order on any of their products. To claim this deal you must go to hiyahealth.com/TCKR http://hiyahealth.com/TCKR. This deal is not available on their regular website. SKIMS: Shop my favorite loungewear and pajamas at SKIMS.com http://skims.com. After you place your order, be sure to let them know we sent you! Select "podcast" in the survey and be sure to select our show in the dropdown menu that follows. Check out my foundation: Higher Hope Foundation: https://www.higherhope.org/ Watch my documentaries: 530 Days: https://www.youtube.com/watch?v=CjUWkmOjNLk Apartment 801: https://bit.ly/2RJ9XXr True Crime with Kendall Rae podcast: Apple Podcasts: https://apple.co/3rks84o Spotify: https://spoti.fi/3jC66pr Shop my Merch! https://kendallrae.shop https://kendallrae.shop/ Check out my other podcasts: Mile Higher (True Crime) @milehigherpod YouTube: https://bit.ly/2ROzJcw Instagram: http://instagram.com/milehigherpod The Sesh (Current events, a little true crime, pop culture, and commentary) https://bit.ly/3Mtoz4X @the_seshpodcast Instagram: https://bit.ly/3a9t6Xr *Follow My Social!* @KendallRaeOnyt Instagram: http://instagram.com/kendallraeonyt Facebook: https://bit.ly/3kar4NK True Crime TikTok: https://bit.ly/3VDbc77 Personal TikTok: https://bit.ly/41hmRKg REQUESTS: General case suggestion form: https://zfrmz.com/yg9cuiWjUe2QY3hSC2V0 Form for people directly related/close to the victim: https://zfrmz.com/HGu2hZso42aHxARt1i67 Join my discord to chat with other viewers about this video, it’s free! https://discord.com/invite/an4stY9BCN C O N T A C T: For Business Inquiries - [email protected] Send me mail: Kendall Rae 8547 E Arapahoe Rd Ste J #233 Greenwood Village, CO 80112
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