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AI Love Song for Mistress Played at Murder Trial Is Most Excruciating Watch in Recent Memory

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Cite

Koebler, J. (2026, September 25). AI Love Song for Mistress Played at Murder Trial Is Most Excruciating Watch in Recent Memory. 404 Media. https://www.404media.co/caleb-flynn-ai-love-song-for-mistress-played-at-murder-trial-is-most-excruciating-watch-in-recent-memory/

Dated when The Aporia collected the article, usually within hours of publication. Check the original for its exact date and byline.

404 Media · collected 2026-09-25 · by Jason Koebler

Quick Summary

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 by AI on 2026-09-26, from this article's own text only (the story summary below draws on all the coverage).

AI analysis

Story summary

Caleb Flynn, a former "American Idol" contestant from Ohio, was found guilty of murdering his wife Ashley Flynn on September 29. The verdict came after a nine-day trial where prosecutors presented evidence including AI-generated love songs and over 100,000 text messages between Flynn and his mistress Alleigha Botner, who testified that she believed he killed his wife to be with her. Investigators used a high-powered magnet in storm drains and searched under vehicles and through attic insulation but did not find the missing gun allegedly used by Flynn. Ashley was shot while sleeping on February 16, and prosecutors say Flynn staged the scene to look like an intruder had broken in. The jury deliberated for just two and a half hours before returning a guilty verdict; Flynn now faces life in prison without parole.

Written for “Caleb Flynn American Idol Murder Trial” on 2026-11-01, grounded in this article and the 31 other(s) covering the same event.

Story

📰 Caleb Flynn American Idol Murder Trial
Crime & Law · 32 article(s) covering the same event. Compare every outlet's account →

Compared with similar articles

This article reads unscored and hedges 6% of its claims. Each row says how that neighbour differs.
The Guardian
Hedges 5 of 34 claims Outlet record 66/100
“The articles describe different aspects of the same trial but do not focus on the same specific incident or outcome.”
Toronto Star
Hedges 3 of 56 claims Outlet record 64/100
“While both articles discuss Caleb Flynn's murder trial for his wife's killing, Article A focuses specifically on a particular incident during the trial involving AI-generated love songs played in court, whereas Article B provides an overview of the entire trial and its progression.”
NBC News
Hedges 1 of 37 claims Outlet record 60/100
“Article A describes a part of Caleb Flynn's murder trial where an AI-generated love song is played, while Article B reports on the jury reaching a verdict in the case.”
New York Post
Hedges 2 of 15 claims Outlet record 66/100
“The articles discuss related events in the same murder trial but describe different aspects: one focuses on an AI love song played during court proceedings, while the other reports on a disturbing photo found on the victim's phone weeks before her death.”
CBS News
Hedges 3 of 61 claims Outlet record 66/100
“The articles cover different phases of the same case: one discusses a song played during proceedings while the other mentions closing arguments.”
How this article was measured signals, leaning charts, publisher record, byline, topics and claims

Signals How these are calculated →

Claims extracted
34
sentences that state something as happening or true
Uncertain
6%
2 of 34 hedged ("reportedly", "may", "according to")
Leaning
not political
takes no side on a contested political question
Publisher signals
95/100
404 Media's corrections and hedging, across everything collected from it. Not a measure of accuracy.
Outlets on this story
32
Crime & Law
Same framing elsewhere
1
articles that frame the event the way this one does
Analyzed 2026-09-26 · how these are computed

How this is being covered How these are calculated →

Article leaning vs. publisher reliability
Source leaning vs. consistency

Publisher

404 Media · 177 article(s) · 0 correction(s) detected
No corrections detected for this publisher. That may mean careful reporting, or simply that nothing has been checked.

Who wrote this

Jason Koebler
25 article(s) here · 1 carrying a prediction
🔮 But if you're in the EU or UK, you might be in luck and can object to that use of your data, as some users have pointed out.
2026-10-28 · assertive framing · Objection, your honor
🔮 “But there’s a lot of work associated with maintaining software so there may be a lot of instances where the software may not be reliable enough to use—I don’t know how many companies are going to be adopting these clones.”
🔮 In fact, with a small amount of Googling and/or clicking around social media, it is easy to find out everything you would ever need to know about the robot and what happened here.
🔮 Hill's decision will not set a binding precedent and there are several other cases throughout the nation considering the legality of warrantless ALPR searches.
🔮 Humoring the idea that LLMs are or could be conscious is a third-rail topic among many people who study and criticize AI.
🔮 “We will not add facial recognition to our devices,” Flock CEO Garrett Langley said in a recent video.
2026-09-29 · assertive framing · Surveillance Finds a Way
🔮 As Flock continues to be the center of a nationwide conversation about automatic license plate reading cameras, the company has said that it doesn’t, and won’t, do facial recognition: “We will not add facial recognition to our devices,” Flock CEO Garrett Langley said in a recent video.
🔮 “You may,” the judge says.
🔮 Last week, Meta executives announced that its much-hyped AI agent, Muse, had a new feature: It could call businesses for you to do things like make a restaurant reservation or a haircut appointment.
🔮 “Millions of people around the world will soon consider large models ‘hoovering up’ all their work to be an astonishing theft of unprecedented proportions,” an internal Microsoft document cited in the case read, adding “almost no one intended for content they created to be used in this fashion, nor are they compensated for its use.”
Also by Jason Koebler
Objection, your honor
2026-10-28 · 404 Media
The Staples Gift Card Heist
2026-10-19 · 404 Media
Nothing else under this byline is closely related to this article, so these are simply their most recent.
All 25 articles by Jason Koebler →

Topics

Cleveland Flynn GrayKey Notes iPhone

Subjects

Flynn PERSON · 9× Wilhelm PERSON · 4× Caleb PERSON · 1× Caleb Flynn PERSON · 1× Cleveland ORG · 1× Joseph Wilhelm PERSON · 1× Nathan Fielder PERSON · 1×

Narrative

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.
framing: assertive · carried by 1 article(s) · first seen 2026-09-26
🔮 “You may,” the judge says.

Claims (34 extracted, 2 hedged)

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 asserted
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. asserted
what → spend → minutes
It simply must be seen to be believed: asserted
It → see → ?
When the songs mercifully end, the court goes silent for several seconds. asserted
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. asserted
he → ask → testimony
“I’ve spent a lot of time on my own and in Cleveland. asserted
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. asserted
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. asserted
I → have → it
“I don’t know if I’m ready to listen to this yet. asserted
I → know → this
I’m sorry,” she responded. asserted
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. asserted
it → send → phone
I don’t want it to be erased.” asserted
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. asserted
melody → mess → times
I tried to sing it with passion and AI took it and went a little extreme.” asserted
AI → try → it
“It’s OK,” she said. asserted
she → ’ → ?
The AI-generated songs were found after Wilhelm used both Cellebrite and Graykey to try to break into Wilhelm’s phone. asserted
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.” asserted
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
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