During Caleb Flynn's murder trial, prosecutors played two versions of an AI-generated love song he created for his mistress using software called ElevenLabs. Forensic investigator Joseph Wilhelm testified that the audio files were discovered on Flynn’s iPhone with GrayKey technology and noted they were in different musical keys, one upbeat and the other melancholic. The unusual use of AI in a serious legal setting caused an awkward moment in court when attendees tried to suppress laughter while listening to the automated renditions.
Written locally by qwen2.5:14b on 2026-09-26,
using this article's own text rather than the other coverage of the
same event (that is the story summary below).
Story summary
Caleb Flynn, a former American Idol contestant, is on trial for allegedly killing his wife, Ashley, in February 2023. Prosecutors claim that Ashley was shot twice in the head while sleeping at their home in Tipp City, Ohio, and that Caleb staged the scene to look like an intruder attack. During the trial, jurors were shown gruesome photos of Ashley's body, including images showing hair, brain matter, blood, and gunshot wounds. The defense has failed to locate a crucial 9mm handgun alleged to be Flynn’s weapon, leading investigators to search underground areas with high-powered magnets without success.
Flynn displayed emotional distress in court, breaking down and exhibiting physical tics as graphic evidence was presented. His former mistress, Alleigha Botner, testified that she believed Caleb murdered Ashley and read chilling text messages exchanged between them discussing divorcing his wife or abandoning their children for the affair. The defense argues these texts refer to divorce rather than murder, attempting to cast doubt on the prosecution's case.
Written for “American Idol Contestant Murder Trial” on 2026-10-05,
grounded in this article and the 11 other(s) covering the same event.
We debated for a long time about whether to write about the following video, which comes from a murder trial in which a man named Caleb Flynn is accused of killing his wife.
asserted
man → debate → wife
The crime is very serious, and very sad, and yet the following video demonstrates something about where we are as a society.
asserted
we → follow → society
The trial has received national attention and has been streaming live.
asserted
trial → receive → attention
Toward the end of the proceedings Thursday, the prosecution played two versions of an AI love song that Flynn, a former American Idol contestant, generated for his mistress.
asserted
Flynn → play → mistress
Investigators found the AI song files as well as lyrics for the song in Flynn’s Notes app after using the forensic tool GrayKey to break into his phone.
asserted
Investigators → find → phone
“We found audio files on Caleb’s iPhone that seem to have been AI generated and related to his relationship with [his mistress],” Joseph Wilhelm, a forensic investigator testified.
asserted
Wilhelm → find → mistress
“They’re in two different keys.
asserted
They → ’re → keys
One’s like a happy or upbeat sad song if that makes any sense, and one
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that → ’ → sense
I think one’s in a minor key, one’s in a major key, but I’m not a music professional.”
asserted
I → think → key
“Permission to publish, your honor?,” the prosecutor says.
asserted
prosecutor → publish → Permission
“You may,” the judge says.
uncertain
judge → say → ?
What follows feels like it should be from an I Think You Should Leave skit or a Nathan Fielder bit.
asserted
You → follow → skit
Everyone in the court spends the next few minutes trying not to laugh during what is, again, a murder trial.
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what → spend → minutes
It simply must be seen to be believed:
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It → see → ?
When the songs mercifully end, the court goes silent for several seconds.
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court → end → seconds
The judge then says: “We’re going to break for the day.
asserted
We → say → day
It’s 10 after 4 [p.m.] We will reconvene tomorrow.”
asserted
We → ’ → 4
Earlier in the day, Flynn’s mistress was asked to read various text messages he wrote her into the public testimony.
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he → ask → testimony
“I’ve spent a lot of time on my own and in Cleveland.
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I → spend → Cleveland
I finished the lyrics to our song.
asserted
I → finish → song
Although it may mean nothing to you, I wanted to give them to you.
uncertain
I → mean → you
I have the music which is completely different to what you’ve heard to this point and I was going to record it but I know there will be no way I would ever be able to actually sing it again,” Flynn wrote.
asserted
Flynn → have → it
“Do you want to hear the song I wrote for you with an AI voiceover,” Flynn also wrote.
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Flynn → want → voiceover
“I have this software called ElevenLabs where I loaded the song on piano and sent it with my computer microphone to which I can pick an AI voice to sing it better.
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I → have → it
“I don’t know if I’m ready to listen to this yet.
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I → know → this
I’m sorry,” she responded.
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she → ’m → ?
“Send me the song and I’ll save it to my phone and I’ll listen when I’m ready, even if it’s a month from now.
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it → send → phone
I don’t want it to be erased.”
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it → want → ?
It messed up the outro as it’s supposed to be done and the vocals aren’t exactly how I want it, it was a little rock-ier at times but the melody is correct.
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melody → mess → times
I tried to sing it with passion and AI took it and went a little extreme.”
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AI → try → it
“It’s OK,” she said.
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she → ’ → ?
The AI-generated songs were found after Wilhelm used both Cellebrite and Graykey to try to break into Wilhelm’s phone.
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Wilhelm → generate → phone
Ultimately Wilhelm used Graykey’s Magnet tool to unlock and examine Flynn’s phone, which gave him a “full file system extraction.”
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which → use → extraction
Wilhelm then obtained Flynn’s messages, the AI audio files, cell phone location history, sleep data from Flynn’s Oura Ring, heart rate data from an Apple Watch, learned that Flynn deleted an app called “AI music song generator” days before the murder, and AirPod connection and disconnection information.
asserted
Flynn → obtain → murder
The Aporia
