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In the Headlines: Caleb Flynn · Deadly Divas True Crime Podcast

• 0:11
  SPEAKER_00: Hey, True Crime Divas and Dudes.
• 0:14
  SPEAKER_00: Tina here, and welcome back to another In the Headlines episode of your favorite True Crime podcast, Deadly Divas.
• 0:22
  SPEAKER_00: And don't worry, Sarah's gonna be back for our usual Friday episodes.
• 0:27
  SPEAKER_00: But I'm here today to talk to y'all about a case that I just have not been able to stop thinking about.
• 0:34
  SPEAKER_00: It has gotten me completely enraged.
• 0:37
  SPEAKER_00: And that is the ongoing murder trial of Caleb Flynn.
• 0:41
  SPEAKER_00: Now, for any of you who may not be familiar with the case, I want to start out with some background.
• 0:47
  SPEAKER_00: Caleb Flynn is currently on trial for the murder of his wife, Ashley Flynn.
• 0:52
  SPEAKER_00: Long before Caleb Flynn was sitting in front of a judge in an Ohio courtroom, though, he was standing in front of the judges on American Idol.
• 1:01
  SPEAKER_00: Caleb actually appeared on season 12 in 2013 and made it to Hollywood.
• 1:06
  SPEAKER_00: He was eventually eliminated, but at the time he talked openly about his faith and his wife, Ashley.
• 1:13
  SPEAKER_00: He said Ashley had encouraged him to audition and told the cameras, I love my wife more than anything.
• 1:21
  SPEAKER_00: And now, 13 years later, Caleb Flynn is on trial for her murder.
• 1:27
  SPEAKER_00: Caleb and Ashley met while attending Lee University, a Christian college in Tennessee.
• 1:33
  SPEAKER_00: They married, had two daughters now 10 and 12 years old, and built a life heavily centered around their faith and church community.
• 1:40
  SPEAKER_00: Caleb worked at the church as a music pastor and worship leader.
• 1:44
  SPEAKER_00: Ashley was also deeply involved in their church community, where she served as a mentor and Bible study leader.
• 1:51
  SPEAKER_00: Outside of church, she worked as a teacher and volleyball coach.
• 1:55
  SPEAKER_00: And eventually, Caleb went to work for Ashley's family's business.
• 1:59
  SPEAKER_00: Her father, Todd Smith, owned a successful flooring and furnishing company and eventually brought Caleb into the business.
• 2:07
  SPEAKER_00: By 2025, testimony showed Caleb was making about$200,000 a year there.
• 2:13
  SPEAKER_00: Ashley's father eventually planned to pass the company down to his two daughters, meaning Caleb also had a potentially very lucrative future tied directly to Ashley's family.
• 2:25
  SPEAKER_00: And they were all very close.
• 2:27
  SPEAKER_00: Not only did they work together, they vacationed together and even attended mission trips as a family unit.
• 2:33
  SPEAKER_00: From the outside, this looked like a close-knit Christian family.
• 2:38
  SPEAKER_00: Then came February 16th, 2026.
• 2:42
  SPEAKER_00: At around 230 in the morning, Caleb called 911 from the family home in Tipp City, Ohio.
• 2:49
  SPEAKER_00: Ashley had been shot.
• 2:51
  SPEAKER_00: She was found lying in bed with two gunshot wounds to the back of her head.
• 2:56
  SPEAKER_00: Their two daughters were sleeping inside the house.
• 2:59
  SPEAKER_00: Caleb told police that an unknown intruder had broken in, shot Ashley, and escaped.
• 3:06
  SPEAKER_00: Police initially treated him as a grieving husband.
• 3:09
  SPEAKER_00: Body cam footage shows Caleb crying, collapsing, and appearing completely distraught.
• 3:16
  SPEAKER_00: But just three days later, Caleb Flynn was arrested and accused of murdering his wife.
• 3:22
  SPEAKER_00: He has pleaded not guilty.
• 3:24
  SPEAKER_00: And before we get into the trial, I want to say two things.
• 3:28
  SPEAKER_00: First, Caleb has not been convicted.
• 3:31
  SPEAKER_00: He is presumed innocent unless and until a jury finds him guilty.
• 3:36
  SPEAKER_00: Second, there is absolutely no way I can include everything that has happened in this trial in and in the headlines.
• 3:43
  SPEAKER_00: There have already been days of testimony covering body cam footage, forensic testing, DNA, firearms, financial records, search warrants, family testimony, crime scene evidence, and literally tens of thousands of messages.
• 4:02
  SPEAKER_00: So this episode is not meant to be a complete trial recap.
• 4:06
  SPEAKER_00: I am just giving you the evidence that I think is the most compelling so far.
• 4:10
  SPEAKER_00: The stuff that has made me repeatedly stop and say, what the actual fuck?
• 4:15
  SPEAKER_00: So let's get into that.
• 4:17
  SPEAKER_00: We definitely need to start with Aaliyah Bottner, Caleb's mistress.
• 4:22
  SPEAKER_00: She met Caleb through church while she was in her early 20s and he was in his late 30s.
• 4:27
  SPEAKER_00: Their relationship eventually became sexual and lasted around a year and a half.
• 4:32
  SPEAKER_00: And investigators recovered approximately 107,000 messages between them.
• 4:39
  SPEAKER_00: That is a crazy number, y'all.
• 4:42
  SPEAKER_00: 107,000.
• 4:45
  SPEAKER_00: At one point, they were communicating around 300 times a day.
• 4:49
  SPEAKER_00: They moved between messaging apps, they met privately, they traveled to places where they were less likely to be recognized, and they even got matching Harry Potter lightning bolt tattoos.
• 5:03
  SPEAKER_00: Which is so crazy to me, y'all, because how are you going to get a matching tattoo with your literal mistress while you are still married?
• 5:11
  SPEAKER_00: The audacity is crazy.
• 5:14
  SPEAKER_00: And Caleb obviously knew that because while Aaliyah's tattoo was on her arm and easily visible, he put his in his armpit where Ashley would be much less likely to see it.
• 5:26
  SPEAKER_00: And according to Aaliyah, Caleb talked about Ashley constantly, but not in a loving way.
• 5:34
  SPEAKER_00: He regularly said that he hated her.
• 5:37
  SPEAKER_00: He talked about wanting her out of his life at least weekly.
• 5:42
  SPEAKER_00: And Aaliyah estimated that he talked about Ashley dying about once a month.
• 5:48
  SPEAKER_00: And the jury has now seen messages attributed to Caleb saying things like, I want her dead and gone.
• 5:56
  SPEAKER_00: And I want her gone so bad.
• 6:00
  SPEAKER_00: In another exchange, when Aaliyah asked what she could do for him, he responded, kill her.
• 6:07
  SPEAKER_00: And one of the most disturbing messages prosecutors presented, Caleb wrote that he had stayed awake until four in the morning, literally trying to think of ways to kill her and not go to jail.
• 6:20
  SPEAKER_00: He also said that if he could kill Ashley without going to hell, he would.
• 6:25
  SPEAKER_00: Like, hello?
• 6:27
  SPEAKER_00: If hell exists, I've got news for you, buddy.
• 6:30
  SPEAKER_00: Wishing your wife dead this often is probably not helping your case with the admissions department.
• 6:37
  SPEAKER_00: They are definitely keeping your seat nice and toasty down there.
• 6:42
  SPEAKER_00: And that's before we even get to what prosecutors say actually happened to Ashley.
• 6:47
  SPEAKER_00: Anyway, of course, the defense has a very obvious response to this.
• 6:51
  SPEAKER_00: They say that people say horrible things, and saying you want someone dead is not the same as actually killing them.
• 6:58
  SPEAKER_00: And sure, that's true.
• 6:59
  SPEAKER_00: But these weren't one or two random, angry text messages.
• 7:03
  SPEAKER_00: According to Aaliyah's testimony, this was a pattern that went on throughout their affair.
• 7:08
  SPEAKER_00: The same general ideas repeated over and over.
• 7:13
  SPEAKER_00: I hate her.
• 7:14
  SPEAKER_00: I want her gone.
• 7:16
  SPEAKER_00: And I want her dead.
• 7:18
  SPEAKER_00: That is a lot more compelling than saying something once in the heat of the moment after a big argument.
• 7:25
  SPEAKER_00: And Caleb wasn't the only participant in these conversations.
• 7:28
  SPEAKER_00: Aaliyah was not just an innocent bystander.
• 7:32
  SPEAKER_00: At one point, she even texted Caleb and said, I want to kill her, Caleb.
• 7:38
  SPEAKER_00: And Caleb replied, That makes two of us.
• 7:42
  SPEAKER_00: In another exchange, Caleb told Aaliy, Please hire someone to take Ashley out.
• 7:48
  SPEAKER_00: I need you in my life.
• 7:50
  SPEAKER_00: I need you.
• 7:51
  SPEAKER_00: And Aaliyah's response to that was so tempting.
• 7:56
  SPEAKER_00: At another point, Caleb wrote, We have to get rid of her.
• 8:01
  SPEAKER_00: Not I, we.
• 8:03
  SPEAKER_00: So yeah, Aaliyah was not just sitting there passively listening while Caleb talked about wanting his wife gone.
• 8:09
  SPEAKER_00: Not that that's not disgusting and unacceptable in and of itself, but she was a willing contributor.
• 8:16
  SPEAKER_00: Nobody, and I mean nobody, would ever feel comfortable talking to me about hiring a hit man to take somebody out or to kill them.
• 8:26
  SPEAKER_00: Why?
• 8:27
  SPEAKER_00: Because I'm not evil as fuck.
• 8:29
  SPEAKER_00: You have to be a sick and evil human being just to entertain this, in my opinion.
• 8:36
  SPEAKER_00: But to add to the conversations, and as a woman discussing another woman with two young daughters who has done utterly nothing to you, that is absolute depravity.
• 8:47
  SPEAKER_00: Now, to be fair, she later also told Caleb directly that she did not want him to kill Ashley and that he needed to divorce her instead.
• 8:56
  SPEAKER_00: So I'm not saying the evidence proves she was part of the murder plot, but some of these texts are completely disturbing.
• 9:04
  SPEAKER_00: And let's all keep in mind that texts are only one side of the story.
• 9:09
  SPEAKER_00: Who knows what they were discussing in person that we don't know about?
• 9:13
  SPEAKER_00: Just some food for thought.
• 9:15
  SPEAKER_00: Moving right along, Aliyah also testified about Caleb's gun.
• 9:19
  SPEAKER_00: She said Caleb personally showed her where he kept a handgun in the center console of his truck.
• 9:26
  SPEAKER_00: Immediately after Ashley was killed, police searched his truck.
• 9:30
  SPEAKER_00: The center console was open, and that gun was gone.
• 9:35
  SPEAKER_00: Investigators searched the house, garage, attic, and the surrounding area and even brought in a firearm detection canine, but that gun has never been found.
• 9:46
  SPEAKER_00: Now we get into the lengths Caleb and Aaliyah went to hide their relationship.
• 9:51
  SPEAKER_00: Aaliyah said they discussed using burner phones and that Caleb planned to buy one with cash to prevent a paper trail.
• 9:57
  SPEAKER_00: They also discussed deleting their messages.
• 10:00
  SPEAKER_00: Aaliyah sent Caleb information about how to delete communications and what could potentially be uncovered during a divorce that would be damaging.
• 10:08
  SPEAKER_00: And yes, people having affairs obviously have reasons to hide messages that have nothing to do with murder.
• 10:14
  SPEAKER_00: But when those hidden conversations also include repeated statements about wanting your wife dead, and then she actually ends up murdered, yeah, that doesn't look great at all.
• 10:25
  SPEAKER_00: We also heard some pretty interesting digital evidence.
• 10:28
  SPEAKER_00: A digital forensics expert testified that Caleb's browsing history during the relevant period had been deleted and that he had been using incognito mode.
• 10:37
  SPEAKER_00: And Group Me, one of the apps Caleb and Aaliyah used to communicate, along with Instagram, was uninstalled from his phone on February 16th.
• 10:45
  SPEAKER_00: That is definitely interesting timing.
• 10:48
  SPEAKER_00: So now let's talk about the weekend that Ashley died.
• 10:52
  SPEAKER_00: Aaliyah testified that Caleb had been promising for months that he was going to leave Ashley.
• 10:58
  SPEAKER_00: October, then November, then December, and finally in January when he still hadn't kept his promise, Aaliy said she was basically done believing him.
• 11:08
  SPEAKER_00: Then on February 14th, Valentine's Day, Caleb reached out again.
• 11:13
  SPEAKER_00: Aaliyah told him that she had a date with another man, and that upset him a lot.
• 11:19
  SPEAKER_00: Once again, Caleb told her that he was finally gonna leave Ashley.
• 11:24
  SPEAKER_00: And that same day, he texted Aaliyah, I'm free, but then immediately added, we shouldn't text or leave trails.
• 11:33
  SPEAKER_00: Then came February 15th, the night before Ashley was murdered.
• 11:37
  SPEAKER_00: Caleb texted Aaliyah, it's happening.
• 11:41
  SPEAKER_00: Tomorrow's a big day.
• 11:43
  SPEAKER_00: I choose you, I'm free.
• 11:46
  SPEAKER_00: And most damning actions will come tomorrow, February 16th.
• 11:52
  SPEAKER_00: Then February 16th arrives, and Ashley Flynn is tragically shot twice in the back of the head.
• 11:59
  SPEAKER_00: Aliyah testified that she woke up expecting to hear that Caleb had finally left his marriage.
• 12:05
  SPEAKER_00: Instead, someone sent her the news that Ashley was dead, and even she thought that timing could not just be a coincidence.
• 12:13
  SPEAKER_00: And before I go on this rant, y'all, I have got to cross my T's and dot my I's.
• 12:20
  SPEAKER_00: Caleb has not been convicted of murdering his wife, but after seeing the evidence so far, in my opinion, which I'm allowed to have, he is guilty as sin.
• 12:30
  SPEAKER_00: And I am so fucking tired of cases where a man wants another life with his mistress and somehow his wife ends up dead.
• 12:39
  SPEAKER_00: It is a tale as old as time and it is infuriating.
• 12:44
  SPEAKER_00: Just get a divorce.
• 12:47
  SPEAKER_00: If you hate your wife, if you love somebody else, if you want out for literally any reason, just get a divorce.
• 12:56
  SPEAKER_00: Murder is not the solution.
• 12:58
  SPEAKER_00: Women are not objects, they are not disposable, they are not toys.
• 13:04
  SPEAKER_00: You don't just get to murder a human being because you got tired of her and want a new one to play with because you are a fucking psychopath.
• 13:13
  SPEAKER_00: Like, I am pissed.
• 13:16
  SPEAKER_00: Anyway, let's move on to Caleb's intruder story.
• 13:20
  SPEAKER_00: Investigators testified that the scene did not look like what Caleb described.
• 13:25
  SPEAKER_00: Caleb pointed to a garage side door as the apparent point of entry, and that door was damaged.
• 13:32
  SPEAKER_00: But investigators testified that the damage did not look like a typical forced entry.
• 13:38
  SPEAKER_00: The deadbolt was unlocked, there were no typical pry marks, and some of the wood debris was inside the garage rather than outside.
• 13:46
  SPEAKER_00: Basically, if someone had actually forced their way in, you would expect to see some more obvious damage showing the door had been pushed or pried from the outside.
• 13:55
  SPEAKER_00: Prosecutors actually had the entire door and frame brought into the courtroom for the jury to inspect.
• 14:02
  SPEAKER_00: An FBI tool mark examiner also tested tools recovered from Caleb's garage, including a claw hammer.
• 14:09
  SPEAKER_00: Test marks from that hammer were described as consistent with some of the marks on wood chips from the damaged door.
• 14:17
  SPEAKER_00: Again, not a great look for Caleb.
• 14:19
  SPEAKER_00: And the rest of the scene wasn't helping his intruder theory either.
• 14:23
  SPEAKER_00: An investigator with the Ohio Bureau of Criminal Investigation spent roughly 12 hours processing the house.
• 14:30
  SPEAKER_00: He testified that there were no obvious signs of a struggle, and Ashley was found lying on her side in bed.
• 14:37
  SPEAKER_00: Based on her position and the blood evidence, he believed she may have been asleep or at least lying still when she was shot.
• 14:43
  SPEAKER_00: And his ultimate conclusion was that the homicide had been staged to look like a burglary.
• 14:48
  SPEAKER_00: Police also searched extensively for this unknown intruder.
• 14:52
  SPEAKER_00: I mean, they pulled out all the stops.
• 14:55
  SPEAKER_00: They used drones, thermal imaging, tracking dogs, and officers on foot canvassing the neighborhood, but they couldn't establish a trail showing someone fleeing away from the property, and nearby surveillance also didn't reveal an obvious intruder escaping either.
• 15:11
  SPEAKER_00: And then there were the family dogs.
• 15:14
  SPEAKER_00: Ashley's father, Todd, testified that their golden doodles would bark if someone was simply out in the cul-de-sac.
• 15:20
  SPEAKER_00: So when he heard Caleb's story that a stranger had entered the home in the middle of the night, he immediately questioned why the dogs hadn't gone absolutely nuts.
• 15:29
  SPEAKER_00: And he also testified about something that is just heart-wrenching.
• 15:34
  SPEAKER_00: Right after he got the news about his daughter, and while he was trying to process this, he googled whether a Christian man could snap and kill his wife.
• 15:44
  SPEAKER_00: I mean, this was the man who had welcomed Caleb completely into his family.
• 15:49
  SPEAKER_00: He gave him a job that paid very well and planned a future that also financially benefited him in a big way.
• 15:56
  SPEAKER_00: He included Caleb in family vacations and treated him like his own son.
• 16:02
  SPEAKER_00: Yet even Todd was already questioning whether Caleb's story made sense.
• 16:07
  SPEAKER_00: The financial piece here is very interesting too.
• 16:10
  SPEAKER_00: Caleb was earning around$200,000 a year through Ashley's family's business.
• 16:16
  SPEAKER_00: Ashley's sister testified that their father eventually planned to hand the company down to his two daughters.
• 16:21
  SPEAKER_00: If the company kept growing, each family could potentially earn somewhere between$300,000 and$400,000 a year.
• 16:30
  SPEAKER_00: And the jury actually heard Caleb talk about exactly what he believed leaving Ashley could cost him.
• 16:37
  SPEAKER_00: In one message, he listed what he was willing to sacrifice for Aaliyah, his daughters, his roughly quarter million dollar salary, a place to live, and the church where he served.
• 16:49
  SPEAKER_00: In another, he wrote that leaving Ashley meant ruining my daughter's lives, and yet I will still do it.
• 16:58
  SPEAKER_00: And a few days later, he again said he was willing to lose his job, salary, house, and daughters.
• 17:04
  SPEAKER_00: So Caleb clearly understood that leaving this marriage would blow up pretty much his whole life and completely shatter his poor daughters.
• 17:15
  SPEAKER_00: And yet he was willing.
• 17:17
  SPEAKER_00: There was also a$100,000 life insurance policy on Ashley with Caleb listed as the beneficiary.
• 17:24
  SPEAKER_00: And I actually don't consider that super suspicious because it's pretty typical for married couples to get life insurance on each other, and it's just one policy.
• 17:33
  SPEAKER_00: But the prosecution is definitely using it to their advantage.
• 17:36
  SPEAKER_00: The bigger point they are trying to make, it seems, is that divorce potentially threatened much more than Caleb's marriage.
• 17:44
  SPEAKER_00: His relationship with Ashley's family, his job, his future in the company, his reputation in the church, and possibly how much time he spent with his daughters.
• 17:54
  SPEAKER_00: He had a whole lot to lose if divorce became a reality.
• 17:59
  SPEAKER_00: The prosecution's theory is essentially that Caleb wanted Aaliy in a new life without losing everything else.
• 18:05
  SPEAKER_00: He wanted his cake and he wanted to eat it too.
• 18:08
  SPEAKER_00: The defense says that theory is exactly that, a theory.
• 18:13
  SPEAKER_00: They point out that the murder weapon is still missing.
• 18:16
  SPEAKER_00: Nobody saw Caleb shoot Ashley.
• 18:18
  SPEAKER_00: There's no video of him doing it.
• 18:20
  SPEAKER_00: There's no forensic test that proves Caleb fired a gun that night.
• 18:24
  SPEAKER_00: And Aliyah herself admitted that when the FBI first interviewed her, she lied about the affair.
• 18:30
  SPEAKER_00: She testified that she was terrified of losing her job and destroying her reputation.
• 18:35
  SPEAKER_00: Eventually, she admitted the relationship.
• 18:38
  SPEAKER_00: And the defense will absolutely use that against her credibility.
• 18:42
  SPEAKER_00: And they should.
• 18:43
  SPEAKER_00: But prosecutors also have those roughly 107,000 messages.
• 18:49
  SPEAKER_00: So the jury is by no means relying entirely on Aliyah's memory or interpretation.
• 18:55
  SPEAKER_00: They are seeing Caleb's words for themselves.
• 18:58
  SPEAKER_00: And that is what makes this evidence so compelling.
• 19:02
  SPEAKER_00: So where does that leave us right now?
• 19:05
  SPEAKER_00: We've got a secret affair, more than 100,000 messages, repeated talk about Ashley dying, and Caleb admitting he had thought about how to kill her without going to jail.
• 19:15
  SPEAKER_00: We have a missing gun that his mistress says he kept in the same truck console investigators later found open.
• 19:23
  SPEAKER_00: We have burner phone discussions, deleted communications, a message saying we shouldn't text or leave trails, and apps used to communicate as well as browsing history magically disappearing from his phone on the day Ashley died.
• 19:38
  SPEAKER_00: Then, after months of promising he would leave Ashley, suddenly texts that said, it's happening.
• 19:46
  SPEAKER_00: Tomorrow's a big day.
• 19:47
  SPEAKER_00: I choose you.
• 19:49
  SPEAKER_00: I'm free.
• 19:50
  SPEAKER_00: Actions will come tomorrow, February 16th.
• 19:54
  SPEAKER_00: And on February 16th, Ashley is dead.
• 19:57
  SPEAKER_00: And let's also not forget, investigators say the supposed break-in looked staged.
• 20:03
  SPEAKER_00: That is a hell of a circumstantial case for this jury to consider.
• 20:07
  SPEAKER_00: But like I said earlier, this is only a fraction of what has come out in court.
• 20:11
  SPEAKER_00: There are entire days of testimony I have barely touched.
• 20:15
  SPEAKER_00: There is forensic evidence we could spend hours discussing, and none of it makes Caleb look innocent, let me tell you.
• 20:23
  SPEAKER_00: But of course, the trial isn't over.
• 20:25
  SPEAKER_00: The defense still has its opportunity.
• 20:28
  SPEAKER_00: More evidence may come out that changes how some of this looks.
• 20:32
  SPEAKER_00: Right now, it's looking like jury deliberations probably won't begin until very late September into early October.
• 20:39
  SPEAKER_00: But rest assured, I am going to be watching for that verdict like a hawk.
• 20:44
  SPEAKER_00: So I'll keep y'all updated.
• 20:46
  SPEAKER_00: Until next time, beat Evas, not Deadly.