Listen to the latest episode now!
Oct. 7, 2026

I Choose You: The Caleb Flynn Case

I Choose You: The Caleb Flynn Case

Ashley Flynn kept notes on her phone about school registration and laundry and appointments, and one about teaching her 2 girls how to pray. In September of 2023, she wrote one about her marriage, and she said she hoped Jesus would intervene. Her husband led worship at their church, and he once made it to Hollywood Week on American Idol.

 

Caleb Flynn on American Idol Season 12

Caleb Flynn is sitting down for one of those American Idol interviews, the little packages they cut into the show so you feel like you know somebody before they sing a note, and he's a worship pastor from Ohio. This is Season 12.

At one point he tells them he's kind of a crybaby. Then he says Ashley is the one who encouraged him to try out, and he says he loves his wife more than anything.

He made it all the way to Hollywood Week before they cut him.

Who Was Ashley Flynn of Tipp City, Ohio

Tipp City is a little town north of Dayton, and that's where Ashley grew up. After high school she went down to Lee University, a Christian school in Tennessee, and that's where she met a music ministry student from a small Minnesota town called Braham, and his name was Caleb Flynn.

They got married in 2010. They had 2 girls.

Ashley taught Bible classes for LifeWise Academy and subbed in the Tipp City schools, and she coached 7th grade volleyball and volunteered at her church, Christian Life Center.

She kept notes on her phone, and if you scrolled through them you'd find things like school registration and laundry and appointments, and one note about teaching her girls how to pray.

Caleb Flynn's Worship Career and the Move Home

Caleb started out leading worship at a church in Vandalia, Ohio, and later the family moved to Spartanburg, South Carolina, where Caleb ran worship at a church called Free Chapel, and he stayed there about 6 years.

They moved back home in 2021.

Caleb went to work as a sales VP for Ashley's family's company, making about $200,000 a year, and he also led worship at Christian Life Center, which was Ashley's church.

The Secret Affair With Alleigha Botner

The church brought on a young intern near the end of 2022. Her name was Alleigha Botner, and she was in her early 20s. Caleb was about 36.

Ashley knew the marriage was in trouble. She wrote a note on her phone in September of 2023 saying the marriage had no intimacy and no respect and no fondness and no appreciation, and she wrote that she hoped Jesus would intervene.

Alleigha told the jury it started small, with Caleb asking if he could come over for a hug, and then he told her he had feelings for her, and she said that in May of 2024 it turned sexual. When Ashley went away to teach Bible camp, Caleb and Alleigha spent those nights together. They called it marriage weeks. They gave it a name.

They deleted stuff whenever they got nervous, and they still averaged about 300 messages a day. You end up with about 107,000 messages. That's a lot of messages.

The messages got ugly. In May of 2025 Caleb wrote that if he could kill Ashley and not go to hell, he'd do it in a heartbeat. Months before the killing, he told her he'd stayed up until 4 a.m. thinking of ways to kill Ashley without going to jail. Alleigha sent ugly things too, including one saying she wanted to kill Ashley.

The Anniversary Cruise and the Deadlines

The Flynns took a 15th anniversary cruise. That was August of 2025, and that's where Ashley found the messages.

Ashley reached out to Alleigha herself and asked her to meet, and Alleigha told the jury she never went because she couldn't face her.

Alleigha kept pushing. It's all right there in the texts if you go through them, where she'd give him a deadline and he'd miss it, and they'd fall out and then get right back to texting, until the last deadline passed in January and they stopped talking completely.

Alleigha told the jury that on Valentine's Day she told Caleb she had a date with another guy, and she said that same day Caleb told her he'd already asked Ashley for a divorce.

That same week, Ashley was excited about throwing a Galentine's get-together for her daughters.

The Night of February 15 in Tipp City

Alleigha opens ChatGPT on the evening of February 15 and asks whether messages can be permanently deleted, and she texts Caleb screenshots of the answer. That's a bad plan.

Caleb's been sick. He saw a doctor and came home with a steroid and an inhaler, and he's been saying the cough is why he isn't sleeping in bed with Ashley.

Ashley's phone goes on the charger around 11:20.

Caleb texts Alleigha shortly after midnight, and he writes, "It's happening." Later he sends, "February 16th, day I'll never forget." He also writes, "I choose you."

You can follow the rest of the night on Caleb's devices. Sometime before the 911 call, ChatGPT and GroupMe come off his iPhone. His Apple Watch logs some steps around 1:20. The watch starts moving again at 2:18. It counts 105 steps. His AirPods connect, and the sound on his phone keeps flipping back and forth between the AirPods and the speaker for several minutes, and then the phone unlocks and Caleb calls for help at 2:31 in the morning.

Ashley Flynn's Death and the Bodycam Video

Caleb told the dispatcher somebody broke into the house and shot his wife.

Officers found Ashley in bed, shot twice behind her right ear. She was 37. Her birthday was 8 days away, and her girls were asleep in the house.

On the bodycam video you can hear Caleb sobbing and fighting to breathe, and he throws up, and outside he says the girls are sleeping and they don't know.

Caleb told police he'd been on the bottom bunk in his daughters' room because of the cough, and he heard a shot, and he said he found the side garage door open and the handgun he kept in his truck's console was gone.

Evidence of a Staged Break-In

A state crime scene agent went over that garage door, and the handle was broken, and the deadbolt and the soft wood of the frame had no damage from anybody forcing their way in, and his conclusion was that somebody staged it.

There was also a refrigerator right up against that door, so if you came in that way, you'd have had to push it. At trial, the defense asked the lead detective if anybody ever weighed it. Nobody had, and somebody should have.

The Flynns had a security camera that could have caught an intruder in the garage. It went offline on January 26. Nobody knows why.

Police arrested Caleb on February 19, before any lab results came back.

Investigators brought in an ATF dog and searched the woods and the storm drains, and they put vehicles up on lifts to look underneath. The gun never turned up. Nobody knows where it went.

The Caleb Flynn Murder Trial

If you were on that jury, you listened to Alleigha read her own texts out loud for 2 days, and you heard Ashley's sister say the girls were heartbroken when they found out about the affair.

The cough came back up. The jury saw crime scene photos of the girls' room, and the bottom bunk was piled with stuff, and an investigator said it looked like you could only fit a small child on it. And Alleigha testified Caleb told her he'd been on the couch.

Caleb's lawyers pointed out that nobody found the gun, and there was no gunshot residue evidence and no eyewitness and no confession.

The prosecutor told the jury in his closing that Caleb said he was sleeping, and his devices say he was awake and moving.

The defense rested without calling a single witness, and Caleb never testified.

The jury got the case on Tuesday, September 29. They needed about 2 hours. They came back guilty on all counts, aggravated murder included, and Caleb cried while the verdicts were read.

Caleb Flynn's Sentence of Life Without Parole

Caleb was back in court that Thursday for a short hearing, and when the judge asked if he had questions, his voice cracked and he started crying again.

Ashley's family was there on Monday for the sentencing. Ashley's sister told Caleb, "I do forgive you."

Ashley's brother-in-law read a letter from one of the girls. "Mommy was the perfect person," she wrote. Caleb sobbed in his orange jumpsuit.

Ashley's mom read a letter from one of the girls too. It said Caleb had the best life ever, and he decided to throw it away for a girl who was half his age. Then it said, "And by the way, I don't plan on coming to see you."

Caleb read a statement, and he said he failed his vows to Ashley, and then he said, "As I stand here before God, who is my ultimate judge, I am not lying when I say I did not kill my wife."

Judge Jeannine Pratt called his actions abhorrent and gave him life without parole. The gun and the tampering counts stack on more prison time. His lawyer says they will appeal. Ashley's family is raising the girls now.

After the verdict, the prosecutor said it was time for everybody to focus on Ashley, and her family asked that you remember Ashley for how she lived. One of the notes on Ashley's phone was about teaching her girls how to pray.