'Crying' Pastor Murder Case ROCKED by Affair & $100K Life Insurance

Ashley Flynn's family trusted her husband Caleb and they loved him like he was one of their own. But as they began piecing together what he said happened the night that Ashley Flynn died, they say the story just didn't add up. Today Ashley's family took the stand, her mom, her dad, her sister and her brother in law and they told the jury what they knew about Caleb. The man they say Ashley Flynn loved more than anyone else in the world. What they say changed after they learned about his alleged affair and the questions they say they still don't have answers to. We're on the case presented by law and crime, I'm Chris Stewart. Today some of the people who are closest to Ashley and Caleb Flynn took the stand. These mom, her dad, her brother in law and her sister and all of them said the same thing. They loved Caleb Flynn, they saw him as family and they trusted Caleb Flynn and when he told them that someone busted into their house in the early morning hours of February 16th and killed Ashley Flynn, they believed him. But then you have information about an affair that came out and we learned a good bit today about this mistress who is on the witness list in this case and that's what it appears some questions started. Questions like why didn't the dogs bark inside the Flynn house? These were dogs that were known to go crazy when people came into the home. Why didn't they start barking if an intruder came in and why would someone break in and walk past everything in the house? Remember this happened in Tip City, Ohio, a quiet community north of Dayton. People get targeted in Tip City, Ohio, Ashley's sister said, why would someone break in and kill a woman as she sleeps in her bed and not harm the two children in the room next door and not harm the husband who claimed he was not sleeping in that bed. He was either on the couch or sleeping with his daughters when all of this happened. And would a man so devout to his Christian faith do something so horrific? And then we got to talk about money because Caleb worked for Ashley Flynn's family business. It was started by her dad, it's this flooring business and they outfit churches. And this was a business that was doing really well. And there were a lot of really good things lined up for Ashley or sister, her brother-in-law and Caleb Flynn. And there were also some important questions that came up today during the cross-examination by the defense of Ashley's sister, which we'll talk about a little bit more here in a moment. If Caleb Flynn was having an affair, why didn't anyone see this coming? So I want to get into some of the biggest moments today. And Lawn Crimes, Anjane at Levy host of Crime Fix, she is going to be joining us here in a moment because she is in the courtroom each day for this trial and she can tell us things that we just can't see on the cameras that are streaming it on Lawn Crimes in court TV. And she's also had a good look at the jury and when you think about how emotional the testimony was today, like, how is the jury seeing all of this? And she'll tell us a little bit more about that. But I want to get into this testimony because it is really important. And there were a couple moments that really just hit you in the chest today. But there was one that Ashley Flynn's mom, Jill Smith said. She told the jury about an incredibly emotional moment, the phone call that she received around three o'clock in the morning on February 16th of this year from her son-in-law, Caleb Flynn. And I thought, "What's the world?" And so I answered it and Caleb said, "She's gone." I thought, "Who, what do you mean who's gone?" He said, "Ashley, she's gone." And I said, "What do you mean?" He said, "Someone broken and father." And now one of them said, "Caleb, I'll be right there." He said, "You can't come. The police are here." And I said, "Caleb, I'll be right there." And I hung up and I started getting really busy. So I laid down on the bathroom floor and I can't remember the tile was so cold and I could get up. It seemed like forever, but I don't know, maybe five minutes. And so as soon as I got up, I called Todd and thankfully he answered. And I told him, "Caleb just called and said, "Someone broke in and murdered Ashley." And he said, "Joe, what are you talking about?" And I repeated myself and I said, "He said, "Someone broke in and murdered Ashley." I said, "Like, guys, go over there. I've got to go right now." So I said, "Call your later." So I hung up. You got dressed. And I got in the car and drove over there. And at this point, I knew it wasn't crying because I thought, "There's just no ways. There's no way." "Why I don't want you right?" I threw up in the corner and I saw all the flashing lights and I knew it was true and all the other case. And it was the detective morgue who came up to me first. And he said, "I'm so sorry, Mrs. Smith." And I said, "Is it true?" And he said, "Yes." And Caleb came out. And what did you do when it came out? We hugged each other. And he said, "What are we going to do, Jill? What are we going to do?" And I said, "I don't know. I said, "I'm in shock." And then Jill told the jury what Caleb said happened that night. And this is the one that he would tell investigators hours later. "But before he was seen by the N.T., I asked him, "Can't it what happened?" And he told me, "What did he say happened?" And he said, "They went to bed and he was gulping." So, as I asked him to sit on the couch, so he would sit down on the couch, then he said, "He heard the dogs' callers shaking." And he said, "Then he heard a list of coughing." So he went into the girls' room and he lay down with Ava. And then he heard a gunshot. And he said, "He froze." And then he went in to check on Ashley. And he took her foot, said, "Ashley, baby." And she didn't respond. Ashley, he kept taking her foot, asked the baby. And she didn't respond. So then he turned on the light and saw that she had been shot. And he called 911. But then Jill told the jury something else, something that happened the next morning. She went back into the house to get Caleb's daughters just 10 and 12 years old. And she described what she saw inside the house. He said, "You go straight to the bedroom, go anywhere else to get the girls." So I walked in and I got Ava, I woke up Ava. You walked straight into the girls' bedroom and where was Ava? She was on the bottom bunk. Who was with you guys? I don't think anybody. I mean Caleb may have been behind me, but I don't remember anybody. And did you get Ava? Yes, I got Ava. I got a pillow, a blanket, and Ava. How did she appear when he brought her alphabet? I'm sorry. How did she appear at that time? She was zoned. I mean, both girls were absolutely out of it, sleeping, tired. And then the moment that may have been the hardest thing the jury heard all day. He walked in and said, "Do the girls know?" And I said, "No." And so he sat on the couch in between the two girls and told them, "Why does he have that?" He said, "Someone broke in the house, and her mommy." And she didn't have it. And the girls just started screaming, crying, and they were crawling all over him, saying, "No, no daddy." Alyssa just sat up on the side of the couch and she said, "I don't know how, and I don't know why, but I know God's going to plan, and He's going to work this for good." And then Ava said, "Mommy's with her best friend, Jesus, in heaven." She always talked about her best friend, Jesus, and now she's with him in heaven. And how did it happen after that? We just all cried. So that was Jill Smith. that Ashley's mom and the defense did not cross examine her. Not one question. Then came up Kayla Kite. This is Ashley's sister, and she told the jury that Kayla was family to her she considered him a brother. And on that particular day, did you tell the police that they arrested the wrong guy? 100%. Yes. I did. Why were you against it on that day? I trusted Kayla with everything I had in me. So I remember hearing rumors that there was an affair and I was like, that's I was so mad because it was tarnishing his reputation. I was so mad because I knew I just knew in my heart that he was completely innocent. I really believe that with all my heart. But Kayla is an important witness, not just because she was Ashley's sister, but she's also a CPA and she ran the books for the business that Kayla worked at, the one that was started by her dad, Richard Smith and sons, this commercial flooring and church furnishing company. And Kayla worked there. He was a salesman and he was pulling in about $200,000 a year, which is really good. And Caleb stood to gain a lot with what he had going with this family business. And what were the projections for the next year that you presented to the defendant? Yeah. So I took the numbers and I took the structure that dad was going to give us. And I was showing again, I said, boys in the future, if it continued to grow, you could make upwards of, you know, up to three to four hundred thousand dollars if we keep going that way. And it was a little different than that? Yes. I remember Matthew, you know, like you looked back as Kayla was behind us and we were like, are you seeing these numbers? Because we were getting excited about the future of what the possibility was. And because he wasn't saying much and he just said, yes, yes, I see. But there is a moment that really caught the attention of everyone in the courtroom. And it was when the defense asked Kayla about what Caleb Flynn's daughters were told. And what the oldest daughter said when she learned of the affair was shocking. What was their reaction to understanding that there was an affair with someone that they personally do? They were shocked, they were upset for their vomit because they said, she loved daddy more than anyone else in life. So why did daddy not love her as much? Then after the morning break, the state called Ashley's dad Todd Smith. Not only was he Caleb's father-in-law, he was his boss. He owned the family business. He hired Caleb and he said Caleb was a hard worker that they worked really well together. When they would go on job sites together, they called themselves the 18 because it always went so well. But on the morning that his daughter was killed, Todd was actually in another country. He had driven 16 hours to Quebec, Canada because he was going snowmobiling with some friends. And then we loaded up everything on the truck and the trailer and we drove, we drove back. It's the longest ride in my life. What did you do during that part, right? Through, I called Jill, I'll be a hundred times just to see what the world's going on. And then she started to tell me the story of what happened and I said, I said, I mean, all I could think about, nothing in that story means anything, nothing makes sense to me. Well, I would somebody break in, go in and get into the truck, go walk in there, shoot my daughter, and then learn how. If it was a burly, I would take going around the whole house. How it didn't make sense is those dogs, and they know me sleep in there with Ashley and Caleb. When we pull up to the house, they are barking and going crazy. And then when we get in the house, they're going crazy and we're having fun and jumping with it. I thought, how in the world, I always thought that those dogs would be one of the best defenses about against anything in that house because they were, you could be in the coldest seconds, almost that are starting to bark. And I thought, how in the world did that happen and those dogs not go to the man's. And it just didn't make sense to me, nothing of that makes sense to me. And then one key moment, Todd Smith told the jury what he did on the 15-hour drive home. And then I even googled, I said, can a Christian man snap and shoot his wife and kill his wife? I did a good one that because I thought, hmm, and then I'd call Jill one of the calls and I said, he just said, I don't, nothing makes sense. I said, this really doesn't look good on Caleb and she said, don't even go there. And at that time, I had to suppress it and totally forget it because my wife's well-being worth way more than any feeling or thoughts that I have. I didn't want to put her through anything else so I was sorry, I can set it to her. The final witness of the morning, another member of law enforcement, Captain Tony Smith of the Tip City Police Department, and he brought two facts to the jury that we hadn't heard yet. What is a superboard? A superboard is a service one can pay for, it was located and the two records on Caleb's credit card from September of 2025 through January of 2026 and in my research and that's a report, it's a service you pay for, it deals with Instagram data. So you pay and you input a user account or a handle from Instagram and then weekly, I believe it's weekly, they'll send you a report with in and all activity associated with that Instagram account. So what you like, who stuff you like, who likes your stuff, what are theirs that they like and then friends, new friends and friends lists. So you hear them talk about Snoop report, it's a paid service that tracks someone's Instagram activity, who they follow, who they like, who likes them and who they're connecting with. Captain Smith told the jury that Caleb Flynn was paying for this service, 699 a month starting in September of 2025. The last charge came in January of 2026, which is weeks before Ashley was killed. And then we have to talk about a life insurance policy. Joining us now, host of crime fix here on long crime, Anjenet Levy, who's been in the courtroom throughout the trial of Caleb Flynn. A lot to get to, Anjenet, let's start with Ashley Flynn's mom. She takes this stand. This was incredibly emotional. We've seen her in the body cam video, comforting Caleb Flynn. What stood out to you about her testimony this morning? Well, you know Chris, it was just heart wrenching, you know, she was emotional from the start. This is still so fresh for this family, Ashley was murdered just in February. We're now in September. And just listening to this mom, you know, who's had probably just a fantastic life. She has her two daughters, who she sees every week. They live close by. They're a close knit, tight family. And they just have this, you know, Valentine's Day lunch with Todd Smith, you know, her husband. And days later, she gets this call from Caleb Flynn that an intruder has come in and shot her daughter. And it just, it's so crushing for her. What did the jury look like to you during all of this? The jury was engrossed in this testimony. I mean, they were paying very close attention. They were just all staring at Jill Smith, listening to her every word, hanging on her every word. I didn't see, I don't think a whole lot of note taking because I think that everything she said would really stick with you. And you wouldn't really need to maybe take notes about what she was saying because she's speaking from the heart. It's not technical. It's not clinical. You know, and another thing that really stood out to me about Jill Smith's testimony was the fact that they loved Caleb Flynn. They welcomed him into her, their family. They loved him as a son. Of course, Caleb Flynn wants to see his children in Jill Smith. And her husband were trying to care for them so that he could get some rest. And she was hopeful that him wanting to see them was a sign that maybe he was feeling better or had gotten some rest. And she noticed that they were anxious and were upset after they returned from this walk around the pond with their father. So, you know, I've been kind of wondering, was that pond ever searched for a gun? uh, you know, what that would be quite the hiding place. So I wonder if we'll hear anything about that. - And this is where we get into some of the, um, financial incentives perhaps, a potential money motive for this case. She's the bookkeeper for the family business. And it does seem like there was a lot of money on the line in the future for Caleb Flynn in this marriage to Ashley Flynn. - It really does sound like that, you know, there was this testimony that Todd Smith, the owner of the company, wanted to gift the company. He wanted to retire and just consult for the company and he wanted to gift it to his daughters and have them run it. Basically have Caleb run it along with Caleb's brother and law, Caleb's husband, Matthew. And Caleb was making $200,000 a year at the time of Ashley's murder. That's what he made last year, just a little over $200,000, when you take into account a medical benefit as well. And there was a projection that they had kind of discussed in 2025. She, Caleb had run the numbers. And she had come up with the fact that if they really hustled in these numbers held and they did a good job running the business, they could make anywhere from $300,000 to $400,000 a year. And that would be their salary. That would be Caleb and Matthew's salary running the business. Ashley would handle the social media and do some outreach to potential customers. And Caleb would keep her job working as the bookkeeper. And I'm sure the prosecution will say, well, if he took out, if he murdered Ashley, then he would become co-owner of the business, not just a sales guy whose wife owns the company, he would maybe become even more financially set. So I thought that was very interesting to hear all of that unpacked, just how much he would benefit financially. There was also a $100,000 life insurance policy that Caleb Flynn had on Ashley Flynn. And they also had a bank account that had $85,000 in it. So there was a lot of money on the line. And you have to wonder if he were to divorce Ashley. Would he have been able to stay working for the family business if he left her for a younger woman, this Aliyah Botner, who is from everything we understand, a much younger woman. And she was somebody in the church. And Caleb said she knew her from the church, to walk by and say hello to her. So yes, it was very interesting. And the defense, I think, is also Chris. I think we should touch on this. I think they're trying to lay the groundwork to say that the family and law enforcement colored the girl's view of their father. They tried to tame them and basically turn them against their father. So I think they're basically trying to plant those seeds ahead of the testimony of the two daughters in case they say some really damning things about their dad. Right. And you bring up a good point because in Caleb's testimony, Ashley's sister, and as the cross examination was going on, and Caleb's attorney was asking about what the girls know. And it was like, what was the moment when these girls find out, not only are they dealing with the death of their mom in just a terrible, terrible way, but then they find out about this affair. And the girls are 10 and 12 years old, very young, but also old enough to understand some of the things in the world. And the 12-year-old makes a very interesting statement when she finds out that Aliyah Botner, who's this worship leader at the church, is the person who her dad was having an affair with. Take us through that moment. It was stunning. That the older daughter, who was 12 years old, when they told her that their father had been having this affair with Aliyah Botner. And she and Caleb were in the music group in the church. That the older daughter said, I'm not surprised. Can you imagine that? Your daughter says, I'm not surprised that dad is having an affair with this woman. The other daughter was so upset and couldn't believe that Daddy didn't love mommy more than this other person. I'm paraphrasing the testimony here. But you just shatter your daughter's world, your daughter's view of you. Little girls often just look up to their fathers. I know I was one once a little girl who looked up to my dad. He was just the best man in the world. And when you learn something about your father that makes you realize they're fallible and something certainly like that, it can shatter the image that you have of your father. Well, and it's just like they said that the girls had said something along the lines of like, their mom didn't love anybody else on earth more than she loved their dad. And it's like that's just like the type of line that hits you in the chest. And then you just think about what those statements could be like on the stand. On a Leah Botner, as we kind of like take a look at her and we'll see if she's expected to testify. We'll see if she ends up being called. But before we went to lunch, a member of the Tip City Police Department talked about having to go collect some evidence from a Leah Botner's office, which is at the church where Caleb Flynn was also formerly a pastor. A Leah Botner's like a worship leader. So she would sing in like the church band and all of that. And it seems like detectives had a really hard time finding some of the materials that they would need related to this woman who Caleb Flynn was having an affair with. Yes. Yes, her work laptop. She apparently lost it. And she had gone on a vacation to Florida. This is what Captain Smith said. She had gone on a vacation to Florida in January of 2026 the month before the homicide and dropped her phone in some water. So phone's toast, right? But we don't know if her phone-- we don't know if we're going to hear later that maybe it was hooked up to a cloud or something like that. But the laptop, it sounds like, has not been recovered. And that was her work laptop. And it sounds like she was actually employed by the church. So the Christian Life Center. So that's an interesting little bit there. What was on that laptop? And how did it just kind of vanish? These electronics-- I don't know about you, Chris-- but my electronics are kind of like my right and left arm. You know, my second right and left hand. Without a doubt. Yeah. To lose those. Yeah. To lose those. I mean, I try to put them down and forget about them sometimes. But you know, you use those all of the time. So it seems rather convenient. I think the defense will grill her about the loss of those items, the convenient loss of those items. I think that the defense, when she takes the stand, which we anticipate, will go after her very aggressively on cross-examination. And we know that they have those text messages that the prosecution talked about in opening statements more than 100,000 that were over the course of a little more than a year involving this affair with Caleb Flynn and Alia Bottner. It's also interesting, like, the defense is the only ones to this point who have brought up her name in court multiple times. Like, they did it yesterday multiple times. Today, they keep inserting her into the narrative that they're laying out in front of the jury, which is just kind of interesting. And because that's certainly, you know, the prosecution's talked about the affair, but the defense really brings that up. What do you make of that part of it? I think that the defense wants this woman out there-- let's just put her out there. The prosecution has been more measured and has not put her name out there. Her name is on the witness list. But the defense is like, just put it all out there. I think they're just like, if you're going to rely-- I think this is their position. If you're going to rely on this woman, who they seem to really are looking-- it seems like they're really looking forward to cross-examining her because they keep bringing her up. They're like, if you're going to rely on this woman, who I think they think is a flawed character, a damaged character in all of this, then they're like, bring it. I think that's where they're coming from. And you know, there was an interesting thing, Chris, that I think we should discuss. They talked about-- every family member has talked about these family vacations that they would always go on. And there was a family vacation in October of 2025. That was the only family vacation that Caleb Flynn never went on. He did not attend that family trip. And everybody said that was highly unusual. He said that he was sick and didn't go on the trip. So I think that's going to become incredibly relevant in the timeline leading up to this homicide. What are we seeing in the October 2025 trip? What does it mean? Right. And yesterday, just at the end of the day, they had a detective say that he had searched a search warrant on the Leah Botner's Venmo account, along with other social medias, which was certainly interesting as well. Lastly, Angelette Todd Smith, this is Ashley Flynn's dad. And I can say, as a dad, you just-- man, does it hitch in the chest, just seeing a father talk about the death of his daughter on the stand. But also, this was someone who, from the beginning, his mind went to a place where maybe he didn't even want it to go. His wife didn't want his mind to go in that direction, which was believing that Caleb Flynn could have done this. But it seems like from the jump, maybe before anybody else, He just found pieces. the Caleb Flynn story, not adding up. We know that they had two dogs. He said that the dogs would have gone crazy if there was an intruder in the house, and that wasn't part of Caleb's story. How did he play in the room? Just, 'cause it was a motion, I'm watching it, and I'm feeling emotional watching him on the stand, but just what was it like being in the room with Todd Smith on the stand? - You know, I think it was again very emotional as it was with watching the other family members. It's a bad talking about losing his little girl. He said that he had an incredible relationship with Ashley. He had these two, you know, perfect daughters, essentially, that he had felt that God blessed him with. And he said he had, he had talked to Ashley every week, and you know, just talked about what a good person she was. And I think that, you know, the jury, sitting there listening to him, talk about the loss of his daughter, you know, is very impactful, but it's going to really come down to the evidence in this case. You know, I think it's interesting when you hear about the family dynamic, and hear how close this family was, or at least how close they thought they were. Todd Smith talked about Caleb, you know, being a great fit at the family business, and how he and Matt and Caleb would go out to job sites, and they called themselves the A team, because they worked so well together. But little did they know that this man they believed was, you know, a beloved family member. Somebody they treated like a son, held a dark secret that he kept from everyone. So I think that it's just really devastating to watch. So the prosecution's gonna have to tie this all together in the end, all these little bits and pieces of evidence coupled with the family dynamic testimony to really paint a picture of why this killer, even without a murder weapon, has to be Caleb Flynn and no one else. - Yeah, but you're interesting to hear, like, what more of the prosecution can do to try and fill in that hole when it comes to the gun, because they just, they don't have it at this point, even after all of this time, and Jeanette Levy, host of Crime Fix, in the courtroom for the Caleb Flynn trial. Thanks for taking the time to be with us, as always, we appreciate it. - Hey, guys, real quick, this is a story that goes back a good ways. We've been covering it for months. There's a lot of layers to it. And if you want to see the Bodycam video for yourself, here are the 911 calls. See the court documents related to this case. You can head over to Long Crime Plus. Right now we have a special offer. promo code OTCFALL will get you the first three months of Long Crime Plus for just $299 a month, which is 50% off the regular monthly price. After the lunch break, the state brought the DNA evidence and the results were striking. Item 5.1, the swabbing of the doorknob, did you make any conclusions based on that case, on that file? - Yes. - And what was that conclusion? - That resulted in the single source profile and that DNA profile is consistent with Caleb Flynn. The estimated frequency of occurrence of that DNA profile is rare than one in one trillion unrelated individuals. Ashley Flynn, Jill Smith, Alyssa Flynn, and Abe Flynn were excluded from that sample. So that resulted in a mixture, DNA profile, with one major. The major is consistent with Caleb Flynn, with an estimated frequency of occurrence of the major profile was rare than one in one trillion unrelated individuals. Ashley Flynn, Jill Smith, Alyssa Flynn, and Abe Flynn are not the major contributor and then the remainder of the mixture contains DNA. That's not of sufficient quality for comparison to a standard from any individual. This sample was presumptive positive for blood and it results in the single source profile that DNA profiles consist of a Caleb Flynn. The estimated frequency of occurrence of the DNA profiles rare than one in one trillion unrelated individuals. Yes, this sample resulted in a mixture that mixture had two major contributors. Those two major contributors are consistent with Ashley Flynn and Abe Flynn. The estimated proportion of the population that can't be excluded as a possible major contributor to those profiles is rare than one in one trillion. Caleb Flynn, Jill Smith, Alyssa Flynn, are not major contributors. So, based on the slide before, was there any DNA found from anyone other than Caleb Flynn or any of the people who were living in that house? There was no DNA found that wasn't attributed to a standard that was submitted in the case. And then on cross examination, the defense went after what was found on an arm rest console in Caleb's truck. Going to item number eight, the arm rest in the available, you indicated that this was a mixture correct? Yes. OK, tell us what a mixture tells you as the DNA analyst. A mixture just means there's more than one person DNA present, so there's multiple contributors to that sample. Now, since this is Mr. Flynn's pickup truck, you would anticipate that his DNA would be of his own pickup, correct? Yes. But that doesn't exclude foreign people from it either, correct? Correct. So, there could be being that it's a mixture, another person, other than your standards of Caleb Ashley, Jill, Alyssa, and Eva, could have left DNA on that particular arm rest console with release button. Yes, so there is additional data in that mixture that I can't make comparisons to. And I can't say who that DNA belonged to. But an unknown individual, you don't have a standard for unknown individual, by definition, correct, because they're unknown. Yeah, I only have the standard better submitted. Additionally, item number 23, the exterior master that moved your handle. That also, you identified as a mixture correct? Yes. And the major contributor on that one was actually Alyssa, correct? I thought it's consistent with the length of length, right? And the Caleb Ashley-- excuse me-- if you say Caleb Flynn, Ashley Flynn, Jill Smith, Eva Flynn, are not the major contributor, correct? That's correct, OK. However, that doesn't exclude a foreign person by virtue of the fact that this is a mixture correct. So there is additional data in that sample that I can't make comparisons to. So that, again, would be an unknown person who may have touched that particular better of your handle. I can't say anything about that minor data. But you know it was there. Yeah, I know it's there. That will do it for on the case presented by Law and Crime. I'm Chris Stewart. We'll see you next time. [MUSIC PLAYING]