“I Want Her Dead” | Caleb Flynn’s Mistress Testifies

37-year-old Ashley Flynn was fatally shot in her Tipp City, Ohio, home in February 2026. Her husband, 40-year-old Caleb Flynn, has pleaded not guilty, but prosecutors allege he staged a break-in and killed Ashley to be with his mistress, 24-year-old Alleigha Botner... Closing arguments for the trial are scheduled for September 29.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:13Derrick Levasseur?

  Hey everyone, welcome back to Crime Weekly News. I am Derrick Levasseur.

• 0:17Stephanie Harlowe?

  And I'm Stephanie Harlow.

• 0:19Derrick Levasseur?

  And this week, the woman at the center of the alleged motive in the murder of Ashley Flynn took the stand. Aaliyah Botner testified about her year and a half affair with Ashley's husband, Caleb Flynn, and the more than 100,000 messages the two exchanged during that relationship. And some of those messages, as many of you guys already know, are incredibly difficult to explain away because prosecutors say Caleb wasn't just telling his mistress that he wanted to leave his wife. He was repeatedly talking about wanting Ashley dead, thinking about ways he could kill her without going to jail, and telling Aaliyah that February 16th was going to be the day he would never forget. Just hours later, Ashley Flynn was dead. So today,

• 1:03Derrick Levasseur?

  we are talking about the murder trial of Caleb Flynn, the affair prosecutors say gave him the motive, and what his former mistress told the jury when she finally took the stand. Man, and I've been seeing the clips. I'm not big in the algorithm, but I've been seeing some of the clips. I've been seeing some of the messages. And man, I even saw your video that you put up. Crazy, crazy talk. And I really can't wait to dive into this one.

• 1:29Stephanie Harlowe?

  It's crazy. This is what everybody thought Nicole Kissinger was, but we didn't have like the direct evidence to show that she was as involved. We have the direct evidence. They made Aaliyah Botner read it in court, which was a deserved form of public embarrassment.

• 1:47Derrick Levasseur?

  They prosecutors, they knew exactly what they were doing.

• 1:50Stephanie Harlowe?

  Yeah. And I don't know if this is a hot take, but I think she should be charged right next to him. So.

• 1:56Derrick Levasseur?

  You know, I would normally say that it is, but I will, I have not gone over all the details, but I will say there was one clip that I watched. And we don't have any clips today, so you'll have to go back and watch them as we're talking about them. But there was one particular clip, and I'm sure you're going to talk about it today, where he's like, read the next line. And she starts crying. And she's like, waiting, waiting, because she knows how bad it is. And she's like, I didn't mean it.

• 2:21Stephanie Harlowe?

  I didn't mean it.

• 2:22Derrick Levasseur?

  And then she says, I want her dead, or something along those lines. And it's like very direct and to the point. And apparently, this isn't the only time she said something like this. And so when you keep saying it over and over, you have to have some level of responsibility there because you're basically telling him, this is what you want.

• 2:41Stephanie Harlowe?

  Well, no, there's more. She, there's more than that even. So.

• 2:44Derrick Levasseur?

  I know. And I think a lot of people are going to agree with you. And I don't even necessarily think I completely disagree with you. As far as the charging, we'll talk about it. We'll talk about it in the episode. And then there was also a video of him like showing his house and saying, I love Aaliyah. Like, I'm home alone. It was.

• 3:01Stephanie Harlowe?

  She made him, she made him send her things to show that he was alone. Or she'd be like, oh, don't watch TV in the living room because your wife, Ashley, even though you're not talking to her, might sit in there and watch TV with you. Like, just absolutely insane. And actually, I want to announce to you and everyone, this is our next series.

• 3:19Derrick Levasseur?

  Whoa, okay.

• 3:20Stephanie Harlowe?

  Because there's a lot. There's a lot here.

• 3:23Derrick Levasseur?

  Yeah. And Caleb's a pastor, right?

• 3:25Stephanie Harlowe?

  Yeah, I guess.

• 3:26Derrick Levasseur?

  He's a pastor, was on American Idol.

• 3:28Stephanie Harlowe?

  Yeah.

• 3:29Derrick Levasseur?

  I mean, this story definitely is made for a movie, a movie plot, for sure.

• 3:35Stephanie Harlowe?

  Crime Weekly's Next Deep Dive, for sure. So.

• 3:36Derrick Levasseur?

  There we go. Crime Weekly's Next Deep Dive. Here we are.

• 3:39Stephanie Harlowe?

  Ashley Flynn, yeah.

• 3:40Derrick Levasseur?

  Ashley Flynn and Caleb Flynn. Okay.

• 3:42Stephanie Harlowe?

  If you haven't been following this case, let me just give you a quick recap of what it is. We had to go back to the early morning hours of February 16th, 2026, in Tipp City, Ohio. Ashley Flynn was 37 years old, mother of two daughters, former elementary school teacher, and a volleyball coach in the Tipp City School District. She lived with her husband, that idiot Caleb Flynn, and their children in a home on Cunningham Court. Caleb was involved heavily in their church, had worked as a worship pastor, and years earlier had even appeared as a contestant on American Idol. His five minutes claimed to fame that he didn't even really get far. But from the outside, yeah, he sucks. I hate him. From the outside, this looked like a family that was deeply rooted in their church and their

• 4:25Stephanie Harlowe?

  community, a family who had it all, you know, beautiful life. And what you need to understand is Caleb was making good money, over $100,000 a year, but working for Ashley's father's business. Okay. And here's another thing. Ashley's father was getting older, all right, and was talking about retiring. And the family had just had a meeting about like what was going to happen. And apparently, Ashley's father was going to pass down the business to Ashley and her sister, and then their respective spouses. And they would split those proceeds from the business 50/50. And it was going to be somewhere between like 300 to 400,000 a year. So on top of the 100,000 he's making by being a salesperson,

• 5:07Stephanie Harlowe?

  now he's going to take 300 to 4,000 a year each. So that would have been Caleb and Ashley's half, plus what he's making as a salesperson. And so there's money on the line here. As far as why is he just not divorcing Ashley, right? That's the question. So at approximately 2:31 in the morning on February 16th, police were dispatched to the Flynn home after Caleb called 911. And basically, he said he was sleeping on the couch because he'd been coughing and he was not trying to disturb Ashley. And then he went into his daughter's rooms, and he was watching them sleep. And then he heard two gunshots. And then he phoned

• 5:48Stephanie Harlowe?

  the garage door open. And then he found Ashley in their bedroom. She'd been shot in the head in her sleep, twice in the back of the head while she was in bed. Yeah. So Caleb's like, I was here, but somebody entered, killed my wife for absolutely no reason, and then left, made their escape.

• 6:02Derrick Levasseur?

  Didn't steal anything? Nothing?

• 6:04Stephanie Harlowe?

  Nothing, nothing.

• 6:04Derrick Levasseur?

  No, just went right to her bedroom, shot her in the back of the head twice and left.

• 6:07Stephanie Harlowe?

  Twice and then left. Okay.

• 6:08Derrick Levasseur?

  So this is an assassination.

• 6:10Stephanie Harlowe?

  And when we, when we go in this series, we'll talk about all the specifics of that.

• 6:14Derrick Levasseur?

  But this is more just topical, just kind of going over the general details.

• 6:19Stephanie Harlowe?

  Yes. So he goes in, he has a police interview, this, this, and that. Obviously, eventually, he'll be arrested because ain't nobody believed it. Nobody did. Just from everything.

• 6:30Derrick Levasseur?

  I mean, come on. Sounds believable to me. Just.

• 6:32Stephanie Harlowe?

  The 911 call, that you have police body cam footage when they come in, he's just acting weird. So now we find out Caleb had been involved in a long-term affair with a much younger woman named Aaliyah Botner. Aaliyah had met Caleb through their church, the same church that Ashley goes to and is involved in. They met in 2022. She was 20 years old. He was, I think, 37 or 38. She was working there as an intern for another worship leader. Their communication, she said, eventually became much more personal. She said he started texting her in March of 2024, being like, can I have a hug? Can I come over and give you a hug? And that's what it started. And then they were playing iPhone games. But once again, you are a grown ass man with two kids and a wife. You're

• 7:16Stephanie Harlowe?

  also a worship leader in the church. There's never any professional way to be texting a 20-year-old woman when that is your situation. But that's what's happening. And then in May of 2024, that's when their relationship turned sexual. Okay. Now, what followed was an extraordinarily intense relationship conducted largely through their phones. So investigators recovered more than 100,000 messages exchanged between Caleb and Aaliyah over roughly a year and a half. And this is like after they deleted a bunch of messages too, because she talked about how they would constantly delete their messages and use different messaging apps. Because at some point, Ashley went into Caleb's iPad, which he was deleting stuff off his phone, but it was still there on his iPad. And she saw a picture of Aaliyah's

• 7:59Stephanie Harlowe?

  hand with a ring that Aaliyah had drawn on her finger. And then the message was something like, you know, I want to be your wife. It was just so gross. And I guess.

• 8:09Derrick Levasseur?

  What was Gwen Stefani's husband's name?

• 8:11Stephanie Harlowe?

  Blake Shelton?

• 8:12Derrick Levasseur?

  No, before that. That's her husband now.

• 8:14Stephanie Harlowe?

  Oh, Gavin Rossdale.

• 8:15Derrick Levasseur?

  He got caught with the iPad too. That's how it was. The iPad got him.

• 8:19Stephanie Harlowe?

  So after that, Caleb factory resets the iPad. So the iPad's no longer an issue.

• 8:24Derrick Levasseur?

  The iPad factory resets it.

• 8:26Stephanie Harlowe?

  And then, yeah, and then they started using a different app. They weren't using iMessage anymore. But they have these conversations, and Caleb and Aaliyah are talking about being together, getting married, Caleb leaving Ashley. And Aaliyah testified that she repeatedly gave him deadlines to leave his marriage. And those deadlines would pass. I think there was something like five deadlines. She'd be like, if you don't do it by this time, we're done. But they would pass, and she'd still stay with him. Okay. But there was something else running through those conversations between Aaliyah and Caleb. And that topic that they seemed to like to talk about more than anything was Ashley, Caleb's wife, and how much they both hated her. So let's take a quick break. We'll be right back.

• 9:07Stephanie Harlowe?

  This episode is brought to you by Aura House. And I have to say something that is important to me. When decorating and putting together a house is a thing you might not expect, which is the scent, the smell of your house.

• 9:17Derrick Levasseur?

  Absolutely, because that's usually the first thing you notice when you walk into someone's house is how it smells.

• 9:21Stephanie Harlowe?

  Yeah, I mean, you're probably nose blind to your own house, but when people come in, they are not.

• 9:26Derrick Levasseur?

  No doubt, no doubt.

• 9:27Stephanie Harlowe?

  You can have the furniture, the lighting, the blankets, the whole thing looking perfect. But if the house smells weird or off, that's what people remember. Aura House is basically designed around that idea. It's a premium cold air fragrance diffuser, no flame, no heat, no wax, no water tank, and it can cover up to 650 square feet, which is huge. And that immediately appealed to me because I love candles and lighting candles and having that smell there, but candles also require supervision. You light one, walk away, forget it exists, come back later, and suddenly you're doing a mental fire safety audit of your entire house.

• 10:00Derrick Levasseur?

  Yeah, with Aura House, you can set it and it runs quietly in the background. The scent lasts for around 30 days per fill, and you can adjust the intensity or schedule it from the app.

• 10:09Stephanie Harlowe?

  And that's very much my speed. I like things that make my house feel nicer without becoming another task I have to manage. And the scent itself is really good. It's that layered, high-end hotel lobby kind of smell, the same cold air diffusion technology that a lot of these luxury spaces use.

• 10:24Derrick Levasseur?

  Yeah, you know, when you walk into like a really nice hotel and you think, oh my God, why does it smell so good?

• 10:29Stephanie Harlowe?

  Oh, absolutely.

• 10:31Derrick Levasseur?

  They're using some type of infuser, some type of, they definitely got something going on through the vents there to make it smell like that.

• 10:36Stephanie Harlowe?

  Yeah, exactly. And this is very similar to that. The oils are formulated without parabens or phthalates, and that's awesome because we want to avoid those things. Those things are in a lot of scents that you have for your house, and these ingredients are known to be toxic to dogs and cats and probably a little bit to, you know, humans as well. And that matters to me. If I'm going to have something running in my house, I want to know what's actually in it, especially with pets and kids around.

• 11:01Derrick Levasseur?

  Yeah, and if you're not sure what scent you want to pick, they actually have a scent quiz. Plus, they have different collections ranging from bright and fresh to earthy to hotel-inspired. And like, so I've seen this before where if there's a certain hotel you like and you like the way it smells, and for some reason, no matter which hotel you stay in, whatever part of the country, they all smell the same. This is the secret sauce. This is how they're doing it.

• 11:23Stephanie Harlowe?

  Yeah, they have a signature scents at their hotels. All of their scents are really good. But of course, I do have my favorites. Usually I have the one called Collins going. It's citrusy, it's clean smelling. It was inspired by W Hotels in Miami and South Beach, so I get that eternal vacation vibe in my house.

• 11:38Derrick Levasseur?

  I like it, I like it.

• 11:39Stephanie Harlowe?

  So if you're the type of person who notices the details, this is a pretty easy one to fix. Use code CRIMEWEEKLY at aurahouse.com for a discount on your first order. The link is in the description box as well.

• 11:57Stephanie Harlowe?

  Okay, so according to the messages that Aaliyah had to read out loud in court.

• 12:02Derrick Levasseur?

  Brutal.

• 12:02Stephanie Harlowe?

  Caleb repeatedly expressed his hatred for his wife. They had a name for her, so he called her a bunch of things, bitch, whore, slut. Caleb told Aaliyah that two years prior, Ashley had cheated on him. And there's no evidence of this, by the way, but he said Ashley had cheated on him and he was like, I want to leave her, but I can't because two years has passed and it's too late. Like, there's a statute of limitations under cursing.

• 12:26Derrick Levasseur?

  You didn't know that? You didn't know the rule? If you find out about an affair, but you don't leave within a two-year period, you no longer have the right to leave.

• 12:34Stephanie Harlowe?

  Are you being serious?

• 12:35Derrick Levasseur?

  No.

• 12:38Stephanie Harlowe?

  He's stupid for saying it.

• 12:39Derrick Levasseur?

  You just asked me, but you're like, are you being serious?

• 12:42Stephanie Harlowe?

  Well, I didn't know if there's some loophole rule I didn't know about, but.

• 12:47Derrick Levasseur?

  No, there's no loophole.

• 12:48Stephanie Harlowe?

  That's what he told Aaliyah, and she's like, well, I believed it. You didn't believe it. We can sit here and be like, oh, she was 20 years old, maybe she, you have Google, okay? And we know.

• 12:57Derrick Levasseur?

  Well, it's a personal choice. I mean, you can leave whenever you want. When we're talking about divorce, I mean, yeah, I don't know if there's a legal thing like, but if you have.

• 13:04Stephanie Harlowe?

  You don't even need a reason.

• 13:05Derrick Levasseur?

  No, but irrevocable differences. Like, at the end of the day, you're deciding to separate for whatever reason. You don't have, there's no statute of limitations on adultery.

• 13:14Stephanie Harlowe?

  Or she cheated on me two years ago. We tried therapy and I tried to get over it and I couldn't.

• 13:17Derrick Levasseur?

  Yeah, we tried to work, it didn't work out. If anything, it shows that I gave an effort. I tried for two years.

• 13:22Stephanie Harlowe?

  So he's full of shit. They gave Ashley all these names. The one that they used most of all was douchebag or douche. That's, yeah, Caleb said Ashley doesn't deserve to be called by her name or going to call her douchebag. So that's how they, that's how he, both he and Aaliyah referred to Ashley.

• 13:39Derrick Levasseur?

  Yeah, this is a pastor, by the way.

• 13:41Stephanie Harlowe?

  Yeah. Then he basically, in May of 2025, Caleb wrote that he, if he could kill Ashley without going to hell, he would do it. In another exchange, he said he wanted her dead. He once said, if I could kill her without going to jail or prison, I would do it. And then in August, Caleb and Ashley go on a cruise for their 15th year anniversary. And it's on that cruise that Ashley discovers messages once again between Caleb and Aaliyah. And what does Ashley do? Ashley texts the mistress, Aaliyah, and she's like, I found these messages. I'm very confused about what's happening. We should get together when I get back because we need to talk. So she's basically not even being like, you bitch, I'm going to kill you. She's saying like, I need to know, what is your, what is your side?

• 14:24Derrick Levasseur?

  I think we're both being misled here. We need to, we need to have a conversation.

• 14:27Stephanie Harlowe?

  Yeah, because Caleb's telling Aaliyah, I have nothing to do with her. We're basically just roommates.

• 14:34Derrick Levasseur?

  But they're going on the universe for vacations.

• 14:35Stephanie Harlowe?

  Mm-hmm. And, and then Aaliyah's texting Caleb and being like, oh, where is she? Is she home? I don't want you two being home together. And so that's when he's sending the videos like, see, I'm alone. I love Aaliyah, I love her.

• 14:47Derrick Levasseur?

  So embarrassing. There's so many, and I've only seen a little bit, but like, there's so many embarrassing, the mute, the video or the song, the song that they played at the court during the trial.

• 14:58Stephanie Harlowe?

  That would be the AI song? Oh, yeah.

• 14:59Derrick Levasseur?

  The AI song, oh my God, bad.

• 15:01Stephanie Harlowe?

  Yeah.

• 15:02Derrick Levasseur?

  It's bad, guys.

• 15:02Stephanie Harlowe?

  It's like, we started off as friends.

• 15:05Derrick Levasseur?

  Caleb's down bad, man.

• 15:06Stephanie Harlowe?

  But our souls connected. Oh, awful. I think he was like happy when it was being played though, because he was looking around. He's like, this is good, right? Like, this is the most views my music will ever get.

• 15:16Derrick Levasseur?

  Do you guys know I was on American Idol?

• 15:18Stephanie Harlowe?

  This is, I was on American Idol. And like, don't get me, don't get twisted. It's not like this guy can't sing. He can sing.

• 15:23Derrick Levasseur?

  I'm sure he can sing.

• 15:24Stephanie Harlowe?

  It doesn't matter. He sucks. Okay, so they go on the cruise. Ashley finds a text. She says to Aaliyah, I want to give you a chance to explain yourself. Aaliyah says, I'm too busy. And on the stand, Aaliyah was asked, why didn't you meet with Ashley? And she's like, I just couldn't face her, knowing what I was doing. No, bullshit. You couldn't face, you had no shame, you had no guilt. You just didn't want to meet that woman and tell her that her husband was talking about killing her constantly because Aaliyah could have prevented this, right? If Ashley's saying, let's meet.

• 15:54Derrick Levasseur?

  I would agree with that.

• 15:55Stephanie Harlowe?

  Yeah.

• 15:55Derrick Levasseur?

  I would agree with that.

• 15:56Stephanie Harlowe?

  So now she avoids meeting Ashley. And at that point, Aaliyah could have said, yeah, it is a little concerning, actually. He talks about killing you nonstop, but she's not going to do that because Aaliyah's also talking about killing Ashley nonstop.

• 16:07Derrick Levasseur?

  And, and for anybody who pushes back and says, well, listen, it's not her who killed, killed Ashley. She could have simply said when Caleb made a comment about wanting to kill her, hey, you know what? I don't want the woman dead. I just want you to leave her.

• 16:20Stephanie Harlowe?

  Okay, well, she did sometimes, okay?

• 16:23Derrick Levasseur?

  Sometimes, but not all the time.

• 16:24Stephanie Harlowe?

  But it doesn't matter because I'm not saying that Aaliyah is responsible for what Caleb did.

• 16:29Derrick Levasseur?

  No, no, no, no.

• 16:30Stephanie Harlowe?

  I'm saying she's responsible for what she did.

• 16:32Derrick Levasseur?

  Right.

• 16:32Stephanie Harlowe?

  Okay? So after they get back from the cruise, Caleb apologized, not to Ashley, but to Aaliyah. He was like, I'm so sorry I went on that cruise. I should never have done that to you. I'm so sorry I hurt you that way. And then Caleb told Aaliyah that he'd stayed awake until four o'clock in the morning, thinking about ways to kill Ashley without going to jail. Now, Aaliyah testified she did not believe at the time that Caleb would actually kill his wife. In response to that particular message, she told him she was not asking him to take Ashley's life. She wanted him to just finally get divorced. However, understand that Aaliyah was also saying, by the way, when you do get divorced, it's your kids or me. Because either you get full custody of those kids and they never see their mother and she's a 0% a part of our lives at all.

• 17:16Stephanie Harlowe?

  Like, I don't want to hear about her. I don't want her seeing the kids. I don't want her around. I don't want you talking to her. Or this isn't going to work. I can't have Ashley around at all. And there was no way Caleb was going to get full custody of his children during a divorce because Ashley was not a bad mother. So the only option.

• 17:32Derrick Levasseur?

  Is that she's no longer around.

• 17:34Stephanie Harlowe?

  To fulfill Aaliyah's requirements of what their relationship would look like after a divorce was to make sure Ashley was dead because there was no way that Ashley was not going to be a part of, to some extent, Caleb's life and to a full extent, her daughter's lives.

• 17:48Derrick Levasseur?

  Yeah.

• 17:49Stephanie Harlowe?

  So this is another thing where I'm saying, Aaliyah knew what she was doing. By the time that, you know, Aaliyah's like, okay, I've given you multiple deadlines. They've passed, you haven't left your wife. Finally, in January of 2026, Aaliyah said she essentially gave Caleb one final chance to leave his marriage. And that, that didn't happen. Now, here's the interesting thing. In January of 2026, Aaliyah Botner went on a solo trip to Florida by herself, just her and her dog. And during this trip, she miraculously lost both her cell phone and her, her laptop computer. She said she was kayaking in the ocean by herself and her, her cell phone just whoop, slipped out of her hand and bounced right in the water. It's gone. Then she said she boarded a flight back to Ohio from Florida and she had her laptop

• 18:33Stephanie Harlowe?

  and she put it in the bins where you put your luggage. And then when she got off the plane, she just forgot to get it. And she filed a report saying she lost it, but you know, it was gone forever, both her phone and her, her laptop. Very convenient. So then Caleb gave Aaliyah a date, February 16th. Okay? Caleb was like, it's going to happen. I'm going to tell her I want a divorce. This was the day. In messages leading into that night, Caleb told Aaliyah that his actions were going to prove that he was serious and he described February 16th as a day that he would never forget. Their final messages were exchanged at approximately 12:45 a.m. that morning. Aaliyah testified that she told him essentially that he was about to be free. Caleb responded that he was choosing her, Aaliyah.

• 19:17Stephanie Harlowe?

  And then, do you know what else Aaliyah told him to do in, in that message? She said, here's, I looked at ChatGPT, and here's how you can completely like delete your communications and how they, they will be less likely to be recovered. Like, here's how you go about deleting data and factory resetting your phone to keep the evidence of this affair from being found. So this is the night before he murders his wife. Okay? Now, I would like you to.

• 19:56Stephanie Harlowe?

  Really truly understand what some of these text messages looked like between Caleb and Aaliyah. But before I do, do you have anything to say about what we've talked about so far?

• 20:06Derrick Levasseur?

  So instead of agreeing with you, because I do agree with everything you've said as far as the behavior, the communications and the convenience of her constantly either losing devices or deleting messages. I am going to play devil's advocate, or in this case, defense attorney for Aaliyah. Okay, not saying I personally agree with this or subscribe to it, but just because I know our audience is vast and there's absolutely going to be people who are on this side of the fence. So without going too far in the weeds, let's break this down. Aaliyah, unless otherwise proven in court, which it doesn't seem like they're going that route because she's a witness in this case.

• 20:46Stephanie Harlowe?

  Well, no, see, she was asked, did you give your, are you giving your testimony? Because you've been given like immunity or anything.

• 20:53Derrick Levasseur?

  And she said no.

• 20:53Stephanie Harlowe?

  Or a deal, she said no. And the way the prosecution is going at her, because they asked her about this phone. And I think they're going to.

• 21:00Derrick Levasseur?

  Okay.

• 21:00Stephanie Harlowe?

  I think they're going to.

• 21:01Derrick Levasseur?

  Kind of like potentially allegedly, maybe like a Wendy Adelson at a later date, something like that.

• 21:06Stephanie Harlowe?

  Maybe, yeah, maybe they just need her to testify.

• 21:09Derrick Levasseur?

  Okay, so with that, with that context, understanding that she could still be potentially charged. Here's what I would say, and I'm just going to go surface level because this is a crime weekly news and we'll save it for the main, the main deep dive. But I would argue that you can say, I want so and so dead. I want to kill this person. I hate this person. I want them gone. You can say all those things. You can, you can say it multiple times a day. You can say it in many different ways, different languages. If there is no evidence to show that you helped facilitate the actual murder, where you were aware of what was happening and you contributed or tried to hide evidence that could implicate Caleb. I think it's going to be difficult to charge her only because her defense attorney is going to say

• 21:54Derrick Levasseur?

  all the behaviors that she displayed as far as covering up text messages and getting rid of electronic devices are because she knew, or at least she thought that Caleb was about to divorce her. That's what he was saying in that message. He was about to end things. And she wanted to make sure that there was nothing tying her back to that. That's again, what they're going to say. I'm not saying I agree with that. I want to hear more about this case. I want you to go through all the text messages, which I know you're going to do. So this is just my surface level reaction.

• 22:24Stephanie Harlowe?

  I mean, I won't go through all the text messages here.

• 22:26Derrick Levasseur?

  I can't wait to do a deep dive. Yeah, I can't. And my, in my opinion, I'm not even saying my opinion will change because I kind of agree with you already. I'm just giving the other side of the coin for now.

• 22:35Stephanie Harlowe?

  Here's some text messages between them. Caleb says, sorry, I'm short. I hate douche. I want to be with my girls, but I don't want to be anywhere near her because one, I hate her and two, I know it hurts you because I hate her. You know, I hate talking about her. And Aaliyah said, what do you want me to do? And Caleb said, marry me. And Aaliyah said, ah, no. And Caleb said, kill douche. And Aaliyah said, oh, man, please. You had mentioned, if only I knew what you have been through, to which I know it's awful. I relentlessly apologize for my life and for how it hurts you, but you know, I hate her. You know, I can't stand her. You know, I can't even stand talking about her. You don't hate Will. You have no problem talking to him or being around him. This is an ex of hers, Will. I'm not trying to compare our situations, but you can at least take some relief knowing I can't stand her and will never be with her.

• 23:18Stephanie Harlowe?

  I can't say that about Will. You know, I hate douche and want nothing with her. Aaliyah said, I hate her. Caleb said, I hate her more, way more. Aaliyah said, I hate her. I've never hated anyone like I do her.

• 23:27Derrick Levasseur?

  I hate that they're having like a hate competition.

• 23:29Stephanie Harlowe?

  They, all they talk about is how much they hate Ashley.

• 23:31Derrick Levasseur?

  Yeah, that's kind of what got them together is their hate for her.

• 23:35Stephanie Harlowe?

  I mean.

• 23:35Derrick Levasseur?

  Their hatred for one particular person.

• 23:37Stephanie Harlowe?

  I don't know if she even hated Ashley or had any feelings about her before. But then, you know, Caleb says, I make you hurt more than I make you happy. And I can honestly say this is what you want and what you see for your life to have, to sneak around, not be able to love publicly and to hurt all the time, knowing my situations. I want you, Aaliyah, as my wife and the mother of my kids. But what do I do? How do I escape this? And Aaliyah says, I don't know, Caleb, you have to find a way. He said, I want her dead and gone.

• 24:05Derrick Levasseur?

  What does she say after that? We don't know.

• 24:07Stephanie Harlowe?

  Well, he says, I want her dead and gone. Is it fair to ask you to live this life with me? I miss you already. And then, so they keeps going.

• 24:16Derrick Levasseur?

  Yeah.

• 24:17Stephanie Harlowe?

  So Aaliyah says Caleb, and he says, yes. And she says, what have you been doing? And he says, he's been crying. And she's like, for the last 15 minutes, because she's like scared that he's talking to his wife. So she's constantly texting him. They did the math. It was like 300 texts a day between them. Because she wants to know what he's doing at all times.

• 24:38Derrick Levasseur?

  It's insane. Well, the video tells you a lot about their relationship. That video I was describing earlier where she's like, hey, I'm just yelling through the house right now to let you know that I'm alone. I mean, this is, this is, even if there wasn't another person, even if he wasn't married, that in and of itself is like a toxic relationship that no one should be okay with. If you have to send videos to prove where you are and that you're alone, that's insane.

• 24:59Stephanie Harlowe?

  I mean, yes, obviously, but what is his idea of this? He's thinking like, I need to prove to this woman that I'm having no relationship at all with my wife.

• 25:10Derrick Levasseur?

  Yeah.

• 25:10Stephanie Harlowe?

  Or she'll leave me, right? And so Caleb's talking to Aaliyah and he's like, you know, I'm sorry, like I can't always be responding to you. If you're angry with me for not responding sooner, I'm sorry. I know it sucks. I wish we didn't have to live this horrendous life. And Aaliyah says, why cater to Ashley and what she [BLEEP] wants? I'm so done with you. I know you have murdered my heart in every hope. You're glad you took my virginity and also my heart and stomped all over it. Enjoy your marriage. I'm done. Life with you and loving you is so easy and just makes sense. I've fallen so madly in love. I don't want to settle for anything else. And Caleb says, we have to get rid of douche. I need you. You're my everything, my heart and soul, my best friend, my love, my better half. And Aaliyah said, I don't even want to say this in a joking way anymore. We need a solution, Caleb.

• 25:55Stephanie Harlowe?

  We need it to be me and you forever, no exceptions. And he says, I've never joked about it. I love you, baby. I love you so much. And she says, I love you, sweetie.

• 26:04Derrick Levasseur?

  Yeah. Why are you doing this to us? My ears. I had to take out one of my headphones. I'm cringing.

• 26:10Stephanie Harlowe?

  Well, then Aaliyah says, do you know how badly I want to say F it to any rules and any barriers and just love you with my entire heart for the rest of my life? I want to kill her, Caleb. It's so bad. And Caleb said, that makes two of us.

• 26:22Derrick Levasseur?

  Yeah.

• 26:23Stephanie Harlowe?

  Right? So these are the conversations they're having, like, she's like divorce her, divorce her. But by the way, if you divorce her, she still cannot be a part of your life in any way, shape or form. So either you get full custody of your daughters or it's still not going to work with us.

• 26:35Derrick Levasseur?

  I see what you're saying. I see what you're saying. And it's taking her words and interpreting them. And you know as well as I do, if you're on the prosecution side and you're potentially charging her at some point, you're going to say exactly what you're describing, that she was saying, hey, I want to be with you. But even if we're together, Ashley can't be around. She can't be physically present. And like you just said, reasonable deduction, there's no way she wouldn't be present and in her daughter's lives unless she was no longer physically capable of doing it. So you're, you're extrapolating out what she means here. On the other hand, the defense is going to say, never at any point does Caleb explicitly express like, I'm going to kill her. That's how we're going to do this. And she says, okay.

• 27:18Derrick Levasseur?

  It's she, that person, their defense attorney is going to argue, hey, she was saying it as out of anger, like a lot of people have said, I want her dead. I want, I hate her. I wish she was dead. I wish she was gone. I want to kill her. A lot of people have said that. It doesn't mean they actually carry through with it. And so even though Caleb was acknowledging it and agreeing with her and saying that they were going to be together and that he had to get rid of her, she always assumed it meant just divorcing her. That's what, that's what the defense will be. Not saying I agree with it, because it almost seems like Caleb's very careful with his words. He never outright says, I'm thinking about killing her. That's the only way we can be together.

• 27:59Stephanie Harlowe?

  I mean, he does. Yeah.

• 28:00Derrick Levasseur?

  He does. Oh, okay.

• 28:01Stephanie Harlowe?

  Yeah, further on in the messages, he's like, I've been, I've been up till 4 a.m. like thinking of how I can do this, how I can like.

• 28:08Derrick Levasseur?

  Okay, well, yeah, this is a deep dive. We, no doubt, I understand now why you're doing a deep dive. Because otherwise we could do a four hour crime weekly news, which I'm not opposed to if I'm being honest, because now I want to know everything. But yeah, just my, my initial reaction without having those, those details and all that extra context and the fabric of this case. My thought would be that's how you would defend against it. But I think you might be right on something here where we may cover this case with a deep dive because Caleb's currently on trial. And yet there is a potential down the road. We're giving an update because now Aaliyah's on trial. So based on what you're saying here, there's a lot of things that can be implied. Fascinating so far, though.

• 28:48Stephanie Harlowe?

  Yeah, so let's take a quick break and we'll be right back.

• 28:57Stephanie Harlowe?

  Yeah, so I mean, there's obviously transcripts. Somebody was helpful enough to place all of the messages into transcripts with times and dates. And you can see as things get closer to that February time, it's much worse. It's much worse on his behalf. And there's not really a lot of her, Aaliyah, being like, no, I don't mean that. Like, I just want you to divorce her. It's very much like pressure on him, pressure on him, pressure on him.

• 29:26Derrick Levasseur?

  End it, end it, end it. I don't care how, end it.

• 29:28Stephanie Harlowe?

  Exactly. And, you know, Aaliyah's like describing Caleb in court and she's like, he was very jealous. He was very possessive. Like, I know he hacked my Instagram. He was trying to like, he thought I liked this guy. And I, once again, red flags on both sides, right? Because Caleb should have red flags. Like, this woman's kind of crazy. I live with my wife and we have children together. There's going to be times where I have to be in the same room as her. Like, this is a crazy thing to expect from me. She should just never be in the same room and always make sure I'm texting you so you know I'm not like forming any connection with her or reuniting with her in any way. But at the same time, you said this guy's hacking your Instagram and you knew it. You also have him talking about his wife, the mother of his children, the woman he married, the woman he once loved, in this way.

• 30:13Stephanie Harlowe?

  I hate her douchebag. I can't stand her. She's the worst person ever. Is it not a red flag as a woman that a man can talk about his wife and the mother of his children in this way? So, the red flags on both sides. But either way, at this point, we have Aaliyah who's testifying for days. And yes, I do think that there's going to be some sort of charge put on her. And obviously, it can't be murder. But somebody, I was watching a video, somebody made a comparison. Like, if you can be charged as an accessory, if you just drive a car away from like, a crime, then why not now? Why is this not considered an accessory?

• 30:56Derrick Levasseur?

  I mean, it'd be simple. Because that person who's driving away is aware of the crime that just took place. The argument is going to be that she was complicit, that she didn't know.

• 31:06Stephanie Harlowe?

  But the argument is going to be, this guy told you over and over again, I want to kill her. And you did not think that that was something that needed to be reported.

• 31:15Derrick Levasseur?

  Yeah, not only did she not think it needed to be reported, she would say it as well. But maybe she felt that that was just their way of like describing things. Like, they called her a douche, but she wasn't actually a douche, like a physical douche. She was, they were referring to her that way.

• 31:28Stephanie Harlowe?

  Douchebag, yeah.

• 31:28Derrick Levasseur?

  Yeah, I want her dead. I want to kill her. Yeah, in the sense of like, I want her gone. And yet, the argument for Aaliyah will be, it was all just kind of hyperbolic. She was just saying it because she was angry and frustrated. She never intended or wanted Ashley actually dead.

• 31:46Stephanie Harlowe?

  Well, here's the thing. This is the night before he murders her. They're talking. And Aaliyah says that, well, basically Caleb is talking to her and he's like, where are you? She's like, I'm at a party with a friend. And he says, I bet your party's going to be super cute. You do everything so well. And Aaliyah said, thank you, don't wait up for me. And Caleb said, you know, I can't do that. And Aaliyah said, I don't like that. I have stuff going on in the evening tomorrow. I'm going to be anxious the whole time, thinking about your stuff and all the things going on. I'm just so anxious. Caleb said, I know this will be tough. I've already made the first step and talked to her now. It's her family, then you and Josh publicly, then Jordan. It's happening. Thank you for everything today. She said, you're welcome. Get some sleep and sleep in. He said, all right, I'll talk to you as soon as I get a photo.

• 32:31Stephanie Harlowe?

  And then Aaliyah said, you're about to be free. Caleb said, I choose you, Aaliyah. You're more than enough. Good night. And Aaliyah said, good night, praying now. They always talk about God, by the way, while they're talking about wanting to kill this woman, they're always praying about it.

• 32:42Derrick Levasseur?

  The irony.

• 32:43Stephanie Harlowe?

  Yes. And Caleb's like, thank you for praying, thank you, I'm praying for you as well. Good night. And then the next day, Aaliyah says, hey, I know you said not to text first, but real quick, when you get that burner, you will have to text this number. I can only receive iMessages with my old number. Let me know when you receive this. I won't text on here anymore. Caleb, I just saw the news. Someone told me to pray for Mrs. Flynn. What is going on right now? Were you behind this? What is going on? Is this for real? So, it looks like she found out on the news that Ashley was killed. And then she's asking Caleb, were you behind this? So, there is, I guess.

• 33:19Derrick Levasseur?

  She knew.

• 33:19Stephanie Harlowe?

  Maybe something to be said. But the fact that you saw Ashley Flynn was murdered and you're asking him, were you behind this? You could say that that's her alibi, is like, I didn't know he was going to kill her because I'm surprised. Or she could just be playing it up so that it looks better. Or the fact that you even knew the second you heard that he could be behind it, meant you realized he was serious when he was saying those things to you.

• 33:44Derrick Levasseur?

  All those things you just said, depending on the audience you presented to, can be something that they'll latch on to. So, I'm not going to sit here and debate it because all three possibilities are in play. And it's all going to be about presentation. And if they decide to charge her, how they take the same facts and present it one way while the defense is going to present the same exact facts another way. It's going to be what the jury believes more.

• 34:09Stephanie Harlowe?

  So, she later deleted that message exchange because according to her testimony, she was afraid police would see it and discover their affair.

• 34:16Derrick Levasseur?

  Yeah.

• 34:17Stephanie Harlowe?

  But listen to this. Later that same day, Aaliyah went to Ashley's parents' home. Okay? Aaliyah went to Ashley's parents' home and she encountered Caleb there. So, this is before Caleb gets arrested, after Ashley's murdered. And she testified that Caleb hugged her and said something that immediately struck her as strange. She said, it didn't happen the way we thought it would, did it? Okay? So, why are you, after he kills Ashley, why are you going to Ashley's parents' home to see him? And he said, it didn't happen the way we thought it would, did it? Okay? So, then, four days after Ashley's murder, the FBI goes to Aaliyah and they interviewed

• 34:59Stephanie Harlowe?

  her because they had received information about the affair because Ashley had told some of her friends. And she said, to the first time, when she's talking to the FBI, she lied and said she didn't really know Caleb that well. And she said she didn't believe Caleb had killed Ashley. And during a later interview, that's when her position changed, right? Because now they've got information, like, yeah, we know you're having an affair with him. But the first time the FBI went to her, she lied.

• 35:23Derrick Levasseur?

  Yeah, the 100,000 text messages, didn't give it away.

• 35:26Stephanie Harlowe?

  So, yeah, that's basically where we're at now with this. But Caleb has pleaded not guilty, believe it or not.

• 35:35Derrick Levasseur?

  They always do.

• 35:36Stephanie Harlowe?

  I find it very, why? Why? Because the defense, his defense is like, yeah, he was having an affair. Yeah, he said he wanted to kill her multiple times. But that doesn't mean he did it.

• 35:47Derrick Levasseur?

  Yeah, yeah. No, I mean, listen, it's pretty straight up why they do it this way. They always are going to plead not guilty because there will be a trial. And as you know, and I know, and our audience knows, not all guilty parties are found guilty. So, the only chance of him ever seeing freedom again would be pleading not guilty and hoping he gets off on a technicality at trial. That's the only chance he has.

• 36:13Stephanie Harlowe?

  Going to trial means all those messages are read out loud.

• 36:16Derrick Levasseur?

  Otherwise, he's going to prison for the rest of his life.

• 36:18Stephanie Harlowe?

  Going to trial means those horrible songs that you made are played in court. So, not only are all of these things going to obviously do nothing besides make the jury and all of us be like, wow, not only did he kill his wife, but he's like, a horrible, awful person. And now we get an inside view. And now you're throwing Aaliyah under the bus because now the world knows what she did.

• 36:41Derrick Levasseur?

  Yeah.

• 36:42Stephanie Harlowe?

  I almost wonder if his defense is going to try to like, do some fancy thing, like, Caleb was manipulated by Aaliyah. See how much she pressured him? See how it was relentless?

• 36:52Derrick Levasseur?

  Would it shock you, any type of defense at this point? It would not at all?

• 36:56Stephanie Harlowe?

  I think it's a good defense. I don't believe it. He still had his own free will and his free choices.

• 37:00Derrick Levasseur?

  And he would have been the one who physically carried out the murder. You know, this reminds me of a case that it's not as egregious, but it's a case that we should probably look into when we're doing our deep dive and try to compare the template, would be Michelle Carter. Are you familiar with that case?

• 37:15Stephanie Harlowe?

  Michelle Carter Conrad Roy.

• 37:16Derrick Levasseur?

  There you go. So, Michelle Carter out of Massachusetts. For anybody who's not familiar with it, I'll give you the 32nd version.

• 37:21Stephanie Harlowe?

  I did a two-parter on my channel. It was horrendous, horrendous.

• 37:24Derrick Levasseur?

  Michelle essentially pushed and pressured Conrad into killing himself to the point, I remember one thing where he was trying to kill himself. He got in the car and she's like, get back in. So, she definitely forced him to kill himself. And she was ultimately charged with manslaughter and convicted of manslaughter.

• 37:40Stephanie Harlowe?

  As she should have been, in my opinion.

• 37:42Derrick Levasseur?

  And so, that case, I will say right now, is much more, was an easier case to prosecute because the evidence was overwhelming. This is a little bit more of a gray area, although I do see some similarities potentially. And maybe we can explore that during the deep dive. That's the one case that comes to mind as you were kind of going over some of the details of this, of this, of this particular case.

• 38:04Stephanie Harlowe?

  I mean, you know for sure, we'll explore that during the deep dive. I'm very familiar with that case. But yeah, Aaliyah Botner needs to be charged with something. Okay? Like, something. Because.

• 38:17Derrick Levasseur?

  We've got to have like an idiot charge.

• 38:18Stephanie Harlowe?

  There's some sort of responsibility you have to have when you realize, because it's all you talk about every day, that this man genuinely hates his wife to such a degree where he's like, if I could kill her and get away with it, I would.

• 38:30Derrick Levasseur?

  I would.

• 38:31Stephanie Harlowe?

  I really want to kill her. I've been, I've been up till 4:00 a.m. thinking about ways I could kill her. I really got to hate her so much. She's the only thing that's stopping me from getting what's most important in my life, which is you, my true soulmate, a 20-year-old girl that I met at church.

• 38:44Derrick Levasseur?

  Not good. I'm looking forward to the deep dive. Was that all we're going to cover on the case here?

• 38:49Stephanie Harlowe?

  I would say so, yes.

• 38:50Derrick Levasseur?

  Okay. So, we're going to switch it up to a more positive note because for our Patreon members, this is the part of the month where we acknowledge you guys. We have our Patreon account. We have our Partner in Crime tier where everybody who's a member of Partner in Crime, at the time when their birthday month comes up, we give them a little shout out at the end of the episode as our way of saying thank you. Thank you for being part of the channel. Thank you for being part of the community. You guys are what makes this, this whole thing run. And so, as per usual, Stephanie has to take it a step further. It's not just birthday shout outs. She's got to give you a full horoscope breakdown. So, Stephanie. Take it away.

• 39:29Stephanie Harlowe?

  All right. So we have actually only one Libra. Okay.

• 39:34Derrick Levasseur?

  Oh, my word. Only one?

• 39:36Stephanie Harlowe?

  The rest are Virgos. So our Virgos are Jen Branner, September 7th, Tiffany Bolton, September 11th, Christie Rebekchi, 919, September 19th, Rebecca Cornwell, September 20th, Amy Aikman, also September 20th, and Jennifer Phelps, also September 20th.

• 39:54Derrick Levasseur?

  Damn, three on 920.

• 39:55Stephanie Harlowe?

  Yeah, you guys have some birthday twins there. So Virgos are the lovable perfectionists of the Zodiac. They're smart, observant, dependable, organized, usually the person silently fixing everyone else's problems while pretending that they're fine. They notice everything, which is great when you need someone detail oriented and thoughtful, and slightly less great when they're noticing the one typo in your text, your crooked picture frame, and the fact that you're doing literally everything wrong. So at their best, Virgos are loyal, practical, caring, hardworking, incredibly helpful. At their worst, they can be over thinkers, control freaks, chronic warriors, and just a tiny bit judgmental, mostly because they genuinely believe there's a correct way to do something. And unfortunately for the rest of us, they've already found it. And I can feel them on that.

• 40:39Stephanie Harlowe?

  So we have one Libra, and that's Cassidy Mansell. That's September 27th, Libra. My daughter Neve is also a Libra, so I'm very familiar with the Zodiac sign. Libras are the charming diplomats of the Zodiac. Social, thoughtful, romantic, stylish, usually very good at making everyone else feel comfortable. They love balance, beauty, good conversation. They're very like much aesthetic people. It's all about the aesthetic and they absolutely hate conflict, which is wonderful until they spend three business days deciding where they want to eat because they don't care. You pick. But they actually don't want to eat where you decided you want to eat. So at their best, Libras are fair, affectionate, easygoing, generous, great at seeing both sides of a situation. They're good mediators. At their worst, they can be indecisive, very people pleasing,

• 41:24Stephanie Harlowe?

  conflict avoidant, and just a little too committed to keeping the peace, even if that means smiling sweetly while privately building a full legal case against you in their head and building resentment. But those are our birthdays. Happy birthday to everybody born in September, and especially to our Patreons born in September.

• 41:41Derrick Levasseur?

  Absolutely. And if you want to join Patreon, you can check it out. It's in the description box below. There are different tiers to choose from, and we have live discussions in there. We have monthly giveaways. We have our, our monthly live where we go on and just get in the chat room with you guys and we answer your questions. We also do cameos every month as well, where you can ask a question or a request. We answer you directly. So there's a lot of different options there. You can check it all out over on our Patreon page. We also have Crime Weekly Plus. If you're not interested in all the extra stuff, all the birthday shout outs, if you want it, if you're just an audio listener and you're listening right now, Crime Weekly Plus gives all the episodes ad free. Same thing for Patreon. They're all ad free. You can get the episodes

• 42:24Derrick Levasseur?

  early and ad free. And you also get our monthly bonus episode, which we just recorded this month's bonus episode. It's an audio only episode. And if you're on Patreon or on Crime Weekly Plus, you will get that as well. Guys, Caleb Flynn, Ashley Flynn, I'm looking forward to covering this one. I know a lot of you are talking about it. Yes, the case is horrific and there's a lot to discuss, but there's also a bigger conversation to be had about culpability, accountability, right? Making comments like this, having these discussions. At what point does a reasonable person understand that the person on the other end of that phone could actually carry through with the behaviors that they're expressing? And what is your criminal, or I should say,

• 43:07Derrick Levasseur?

  legal responsibility in those matters? Do we just completely pass it off as, you know, ignorance? Or do we have to start holding people accountable to not only serve as a message, but a deterrent in the future? Interested in covering it? Can't wait to hear your thoughts on it. We will be back later this week with Jade Benning, part four. It's the fourth and final part. I'm looking forward to seeing how this one plays out. I have seen some things online, but I'm interested to hear how it all came to fruition as far as where we are today. Until then, please, everyone stay safe out there and we will see you soon.