The Pastor's Secret: The Murder Case Against Caleb Flynn

In 2013, Tip CD, Ohio Music Pastor Caleb Flynn auditioned for American Idol. The person that inspires me to be an informer, I guess, would say the Lord. While he also credited his wife Ashley Flynn for giving him the push he needed to try out. I love my wife more than anything. She is very, very pretty. Just woof. I love her. Well, 13 years and two children later, Caleb Flynn was found guilty of her murder. We, the jury in this case, being duly empaneled and sworn, find the defendant Caleb C. Flynn, guilty of aggravated murder, as charged and count one of the indictment. Prosecutors alleged that on the morning of February 16th, 2026, Caleb fatally shot his wife in their home and staged a home invasion to cover it up. The 9-day trial revealed body cam footage from that day, bullet casings from the murder weapon and revealing testimony from Caleb's lover, a member of the family's church, much younger member. The jury took just over two hours to find Caleb guilty of nine charges in total. And this includes three counts of murder, two counts of felonious assault and three counts of tampering with evidence. And was sentenced to life in prison without parole on Monday, October 5th. I'm 48 hours correspondent Anne Marie Green. And this is case by case. So returning to the show today is 48 hours consultant, Herman Weisberg. Herman is a private investigator, former NYPD detective, and the managing director of Sage Intelligence Group, where he oversees investigations. Herman, it's great to have you back. Thanks for joining us. Great to be here. Thanks for having me, Anne Marie. Let's start things off, Herman, by talking about the flints, just who they were. You know, Ashley's death was devastating to her family. She left behind a sister, Kayla Kite, her mother, Jill Smith, her father, Todd Smith. She was also a mother. She left behind two girls, ages 10 and 12. So Ashley grew up in tip city. She ended up staying there basically most of her life. She met Caleb when she went away to college in Cleveland, Tennessee at Lee University. And then the two got married, the same year that Ashley graduated, that was 2010. Ashley went on to become a substitute teacher and volleyball coach in the very school system where she graduated from. I think this is almost sort of like a Norman Rockwell sort of thing, right? Small town girl goes off to college, marries her college sweetheart, comes back to her hometown and becomes this teacher that has this, you know, impact on all these kids. The tip city school system posted something when she died on Facebook and it sort of gives you a sense of the kind of lasting impression that she had. They wrote, she was known for her beautiful smile, warmth, kindness, and the positive impact she had on so many, both in and out of the classroom and on the court. Yeah, such should have been such an idyllic life. It appeared from the outside that, you know, small town growing up like that to beautiful daughters. But the community is definitely feeling a loss. And I think also what sort of adds to kind of the betrayal, I think, is that Caleb was close to Ashley's family. He worked in the family business. They welcomed him in Ashley's father had a flooring and furnishing company. Caleb was a salesman there. Running a business together, I would imagine that they were all pretty close knit family. It can raise tensions as well, especially when it comes to money. But Flynn reportedly was doing pretty well. He was as a salesman, he was making about $200,000 a year. And you know, there's a nice future there, Ashley's father was preparing to retire and he planned for Ashley, her sister Kayla and their spouses, including Caleb to inherit the business and continue it. In court, Kayla said she showed Caleb a spreadsheet of the potential of the company, the growth that was supposed to occur and he definitely took an interest like in this that is as he should have. It's also shouldn't be ignored that tip city police testified to Caleb was the sole beneficiary of $100,000 insurance policy on his wife's life. It wouldn't be the first time that we heard of an insurance policy possibly, you know, feeding into a motive. Definitely. This wasn't a gigantic one, like in some cases, but it was significant. Right, right. Okay, so let's give people sort of a sense of the timeline. Going back to the day of Ashley's murder, around 2.30 a.m. in the morning of February 16th, Caleb calls 911 to report that an intruder broke into his home. They actually played that call in court and want to play some of that for the listeners to hear. I mean, this does sound like a man who has stumbled upon an incredible scene. He's very emotional. You've listened to a number of 911 calls in your career. I'm sure what's your take on his demeanor? First of all, he's quite the water works and the cryer. He actually made a reference to that early in his audition tape. He called himself a crybaby, so he definitely was aware of that. He said he got it from his mom and dad, but he was weeping all through the trial. Another very important part of that that I noticed is he mentions two shots. You know, it's just such an unusual thing to say into a 911 call and what kind of examination did he do to his wife's body to be able to determine the amount of shots and a messy crime scene like that? These are crocodile tears as far as I'm concerned. That is such a great point, you know. She's there in a pool of blood. Like, how would he know two shots? It's not something you check for when you're trying to save your dying wife or you recently assaulted wife. So in that same 911 call, Caleb said that he was lying in his daughter's bedroom when he heard the gunshot. He said that he got up and he noticed his garage side door was open as well as the central call console on his truck where he keeps his gun. According to Caleb, he returned to the house and he finds Ashley in a pool of blood in the bedroom with as we heard two gunshot wounds. So many details and I got to tell you prosecutors love when suspects give a detailed version of what happened because for every point, if they can kind of like discredit that point, they've got plenty to work with a trial. Oh, they had tons to work with your Aunt Maria. The evidence was just not consistent with his story. This man expected us to believe that an opportunist, a homicidal opportunist, broke into his garage, then into the center console of his truck, took out a loaded firearm, entered a house, went right to the master bedroom like he knew the place, murdered a sleeping woman and then left without committing any other crimes. It just does not add up at all. This is this is a guy that apparently he is definitely not a listener to your show or to his, he's probably never seen a cop show on TV because he just made so many, so many errors there that in trying to recreate what he thought was going to be a reasonably perfect crime. During the trial, they actually brought that garage side door into court just to show that the handle was broken off, but the door did not have damage consistent with a break-in. They found particles on the wrong side of the door, anyone breaking in from the outside, this was clear signs of a staged home invasion. If it had been a home invasion, I mean, what would they have seen? The door would have been bent, it pushed in a different direction. What else would investigators be looking for to prove that someone else had been in the house? First of all, the entire house becomes a crime scene. The outside becomes a crime scene. They did tape it off. I saw the body-worn camera footage. Everything gets examined. You're looking for fingerprints. You're looking for a method of exit as well as a method of entry. This whole thing was so contrived and so horribly done. It's not, none of it adds up to an investigator or I'm sure to anybody listening to this show but has any kind of reasonable knowledge of what happens at a home invasion, which nothing adds up here to me. Even sort of the claim that he was lying in his daughter's bedroom, also immediately that felt odd to me before even knowing what the evidence indicated because he says that he leaves the bedroom with his wife because he's sick, he goes out to the couch and eventually ends up in his daughter's room. If you're a parent, I'm a parent. If I'm feeling under the weather, the last person I'm going to cuddle up with is my kid and risk getting them sick. So right away, I thought that doesn't make any sense at all. I'm with you, exactly, and you can look at the bed because the body-worn camera picked up the picture of the bed. There's stuffed animals strewn across it in a way, let me tell you, I have a daughter. I would never mess with her stuffed animals on her bed to lay down while I'm sick to go in there. This whole thing, again, the word contrived comes to mind. He thought maybe laying in the. on the couch where his wife asked him to go. Supposedly for coughing in the bedroom, it would have been too obvious that a bad guy passed him and shot the way. It's just such a so contrived. - And we should tell people that the Flynn girls are now they're 12 and they're 10 and they're being taken care of by their grandmother and their aunt, but you do see photos of the kid's room and it's tight, it's kid-sized bunk beds, like a grown man, I was gonna say grown-ass man, a grown man is not gonna fit comfortably in that room. - A coughing grown-ass man is not gonna go into his little daughter's bedroom and wake them up and delay, it's ridiculous. - So I will say, it is the ridiculous nature of the story that is having me sort of giggle a little bit, but this is a horrible thing. To use your children kind of as your alibi, right? So the kids were not expected to testify. Ashley's mother, Jill Smith, did take the stand and mentioned that one of the daughters seemed nervous in the days after their mother was shot. I wanna play a little of that sound here. - I asked her why she was nervous. - And without telling you what she said, what did you do next? - I marched her down to her dad and said, she's afraid to tell the truth, tell her to tell the truth. - What did she say? Of course, baby, you're supposed to tell the truth. - I mean, it is reasonable that a child would feel very nervous at this time. Their mother has been shot. It's unsettling. So I wonder if there's more to take from what the grandmother had to say. - This is such a horrible thing for these poor kids who have gone through, of course I would have been curious to see what they would have said during an interview or if they were put on the stand. I'm glad they weren't, no child should have to relive something as horrible, no one should have to relive something as horrible as this. And kids can testify against their parents, but the courts obviously try to avoid that. It's protect them. I've testified a lot. It's extremely stressful, I don't care who you are, how many times you've done it. So to put two little girls through this, to make them relive these traumatizing events, I'm glad it didn't happen. But you have to wonder if Caleb took into consideration their age and all the other stuff just so he can pretend that he was in their room during the shooting. I think he definitely took advantage of their age and his knowledge of them. (upbeat music) - So Herman, we've had you on the show before to talk about cases where there's nobody found, right? No body cases, those are tough. In this case, Ashley Flynn is there, there is a body. What they don't have is the murder weapon, but having the body, does that make it a little easier to convict someone like Caleb? - Oh, definitely. It takes a lot of the guess workout. And when you're missing a big component of a case like this, of an investigation like this, you need to replace it with something in a circumstantial evidence. So it's one less thing for the prosecutors to have to replace. This case had tons and tons of circumstantial evidence, including 107,000 messages that come into play. Because they had the body, a cause of death was very clear, multiple gunshot wounds to the head. It's an advantage that you don't have with a nobody case. According to the coroner, for example, Ashley was shot at close range, so that's important. And while they weren't able to find a gun, and I'm sure they wish that they searched more because it was someplace to be found, they were able to match the casings and the bullet wounds. They were consistent with Caleb's gun that was taken from the center console there. He, I really wish that they had found that gun. Obviously, it didn't matter in the big scheme of things, but he didn't really leave the house at that point. When you're hiding something in your own home that you know very well that you've lived in for a while, it's easy. And it's very difficult for police officers to find the hiding spots that nobody knows about. They're not tearing the house apart from all over the place. So let's talk about the additional evidence that investigators found that was inconsistent with Caleb's testimony. And like I noted before, everything was inconsistent with his, as far as I'm concerned, they're looking for signs of a possible break in, and they just weren't there because there was no burglary that had occurred. An hour after the police first got to the scene of the crime, they deployed a drone to try to find suspects. You know, anybody fleeing the scene, they're probably using heat-seeking technology on those drones. They tried to police dog to see if they could track down any suspects. They definitely took this, and they didn't rule out the possibility that this was a home invasion at the time because these responding officers, that's what they thought that they were walking into. And no disrespect to these officers, small department, but I can tell you, I think in the testimony of one of them, they had never experienced a murder in this small town. So they were also dealing with a church leader. You know, somebody of respect, somebody crying their eyes out on this thing, somebody with two little girls. You'd like to think that most police officers responding to a scene like this aren't automatically assuming the husband is the homicidal person. - Right. - So, you know, I could understand why they went out of their way going with his initial story and his initial report, and they'd have to because what if he's telling the truth? You can't let the perpetrator of this get away. - Right, right, and so there were a lot of little things that this sort of didn't add up. And I mean, these are little things, but like, they have two dogs. - You know, and you could see those two dogs, beautiful golden, I'm a dog guy. Golden doodles, I think they are. They're very alert. This is not, dogs don't malfunction. Dogs bark when something's going on, and a burglar breaking in, kicking down a door and all of this. There's not two, I don't think, tell me if I'm wrong in the comments here folks, but I don't think there's two golden doodles that are walking around that would just completely disregard and sleep through a door getting kicked in and a house, guns going off and anything else. It's just ridiculous, they'd be all over the place. - And you mentioned the text messages. There's, we're gonna get into that in a little bit, but there's a lot of sort of digital evidence. The other digital evidence is his Apple watch. I guess he kept it on. And I mean, these things keep track of all of your movement. He said he was asleep this entire time. The watch said otherwise. The old Apple watch evidence, it's crazy to me that you're right, that's something that he just definitely, I think he just doesn't understand the concept of an investigation of what's gonna happen here of how much scrutiny is gonna be put on all of these pieces of information from an investigative standpoint. - Now the jury in this trial actually toured the Flynn home. It's called a jury view. If you follow the Clancy case, you will recall that the same thing happened in that case as well. Their authorities also flagged to the jurors that they did not see any evidence of forced entry. They got another glimpse of the Flynn home in court via the body cam footage that was entered in as evidence. But I wanna talk a little bit about what the footage showed, but also kind of why it's important in some of these cases to have the jury actually go to the crime scene. - The jury view is, we call it a field trip sometimes. There's nothing that can replace having a jury stand where the incident happened. There's just a different perspective there that you're not gonna get from body cam video. Martin Scorsese, he could have directed this film and you're not gonna get the same effect as you will when you're standing where the crime actually happened. The proximity to the bedroom, to the garage door, where the children were sleeping. It's such a vital part of this case, I think, for the jury to really understand where this falls apart. But what the body cam footage does give you is what was happening in the moment. And what do we see? - Oh, I'm addicted to body cam videos. It's like me reliving parts of my previous career. I noticed a lot of things that the truck center console was open, that's where Caleb claims he kept his gun, which by the way, that's very irresponsible gun ownership to leave a loaded gun. You got a 10 year old and a 12 year old daughter in there, but that's just on his side. The garage door had also been open. And I think the biggest thing that you can get from that body cam footage was just Caleb's mental state when the police officers were present the way he was acting, he looked like a mess. He was crying hysterically. I couldn't understand what he was saying. He wasn't making sense at some point, which is all ties to somebody going through a traumatic series of events or somebody that's just done something that's really horrific. It's hard to read. He cries, this guy, he cries at the drop of a hat. Caleb was really sobbing and even fell to his knees on his porch as Ashley's mother arrived at the home that night. It was difficult to watch. It's really frightening how devastated he seemed in this footage and just put on the water works there. So now I want to talk about motive. And we talked a little bit about money but really what the prosecution argued was that he wanted out of his marriage that Caleb was having. having an affair, a year-long affair with a 21-year-old intern, Alia Botner in 2024. He was 38 at the time, by the way. It seems to have been a pretty passionate affair as well. Yeah. Alia was around the same age that Ashley was when they got married. This case takes a big turn right there when there's a passionate affair going on simultaneous. Yeah. And so this is, I mean, this doesn't really go to the evidence, it's not sort of significant evidence in terms of the crime. But there were some AI-generated love songs that were created, a product of this passionate affair. Some of it was played in court. I want to play some of it now. It was you and me. We were proved that forever was something you feel not see-one. Okay. So, clearly music is his love language. This is sort of a baffling, moment in court. In fact, some people in the room are trying to hold back laughter. Like I said, this doesn't necessarily, isn't necessarily evidence connected to the actual crime, but it was still significant. Oh, I'm not a music expert, but I like music and I'm not a prosecutor, but I can see that this being used to show how intense the affair was, it's a good move by the prosecutors. They would have known that the everybody's eyes are going to be rolling and you're suddenly listening to these lyrics. It's deplorable, you know, just the theatrics behind this. I'm going to address the song in her testimony and I think we have some of that to play here. So, you know, this is an intense relationship. The couple even got matching Harry Potter, Lightning Bolt tattoos. Just as an aside, everyone knows when you get a tattoo, couples tattoos. Often is an indication that things are going to go badly down the road. I'm just saying. There's plenty of people with couples tattoos and it's all worked out for them, but sometimes it doesn't. Caleb actually put the tattoo in his armpit in the hopes that his wife would never find it. It didn't really matter because Ashley does discover that he's having an affair. The couple, they are on accrues to celebrate their 15th anniversary and she reads text messages and that's how she finds out, which must have been devastating for her. How are prosecutors able to connect Caleb's infidelity, though, to Ashley's murder? So Caleb and Alia sent over 100,000 messages in the year prior to Ashley's death to each other. These messages were extremely telling Alia shared many of these exchanges on the stand. Prosecutors had her read them for that impact that comes from her voice telling that they were in an intense, passionate affair and it's important to note that this is cheating and the messages show that there's no way around it at that point. Alia had initially deleted these messages and the FBI questioned her and she lied about it initially. The text show Alia asking Caleb to leave Ashley and threatening to leave the relationship if he didn't follow through on leaving her. Caleb refused, citing his family and his reputation. At some point, Alia texts Caleb, and I want to get this right, quote, "I want to kill her Caleb," and quote, "to which he responds," quote, "that makes two of us," and quote, "then about six months before Ashley's death," Caleb wrote again to the young woman saying, quote, "I was up until 4 a.m. last night crying, literally trying to think of ways to kill her and not go to jail," and quote, it reminds me of an expression in the FBI that, you know, the e in email stands for evidence and that really comes into play here, this is just gold for a prosecutor. Hours after Ashley's death, members of their church met at Ashley's parents' house, and according to Alia, when she arrived Caleb hugged her and he said, it didn't happen the way we thought it would, did it? This is extremely telling, very spooky stuff. Yes, I mean, those text messages, I mean, they just stopped short of I did it. I mean, literally, just right, literally two days before Ashley's murder, Caleb texts Alia, I'm free, I'll tell you all, but to be careful for us both shouldn't text or leave any trails, too late, right? So she actually reads the text messages from just hours before the events on February 16th. She read them in court. I don't want to play some of that sound. I said, you're about to be free. He said, I choose you, Alia, here more than enough, good night. I said, good night praying now. He said, thank you praying for you as well, good night. Very romantic, you know, you are more than enough, but we know according to prosecutors that about two hours after that text, Caleb Flynn shot Ashley twice in the head and then he staged a home invasion. So in a hearing on Monday, October 5th, Caleb was sentenced to life in prison without parole. Now during the sentencing, hearing her sister, Kayla Kite had a few words for Caleb and I want to play some of that sound. And I used to call my brother when Ashley died and we learned you were responsible, you were a shocked as anyone. He trusted you, we believe in you, we honestly would have laid down our lives for you. I want you to know something else I do forbid you. I've forgiven both you and Alia, not because what happened should be ever excused or forgotten and certainly not because there shouldn't be severe consequences. I forgive you because I refuse to allow what you did to destroy another part of my life, but feeling my heart but hatred and bitterness. I'm always so impressed by people who have the ability to forgive when it's not like he's taking ownership in any way. And I agree on a percent, I don't forgive. I would find it very hard too. We also heard from her father who spoke directly to the judge saying this. You are, when we, while we choose forgiveness for our own hearts, we still desire absolute justice for us. Because of the violent nature of her murder, compounded by a lack of responsibility, confession or remorse, we as a family ask you to send us him to the fullest extent of the law. He took our daughter, a sister, a granddaughter, an aunt, a cousin, a teacher, a coach, a friend and a loving mother, and the consequences should match the lifelong impact of his loss. A loving mother and perhaps some of the most heart-wrenching testimony came from a statement from one of the Flynn girls, the letter was written and then read in court. Mommy was a perfect person, the absolute perfect person. What did she ever do to make me hate her so much? She loved you, and she cared for you. She took care of you. She loved you as I per heart. She was my best friend, and you should have secured the only mother I ever had. I miss her so much, so, so, so much, you have no idea. I mean, I don't know what the long-term plan was for Caleb after this, but he certainly was not thinking about the devastating impact on his daughters. No, and you know, you'll watch him cry there in this, and that's probably the most appropriate. Those had to be real, because anybody who's a father or a parent listening to those words from their own daughter, that's right out of the twilight zone as far as torture is concerned on such huge impact, and how you could do something like this that would so obviously impact their own children for such selfishness. They're going to be carrying that for the rest of their life. My hope is, and it seems like they have a strong family structure around them, and that will probably help tremendously, it will never feel the void, but it certainly appears as if these young girls are very well loved. This was a good conversation, Herman, it's all great having you join us. Thank you. Thank you. Appreciate it. We will be back next week with another episode of Case by Case, four-hour continuing coverage. You can check the Case by Case feed wherever you find your podcast. You can also watch episodes of Case by Case on the 48-Hours YouTube channel or by searching Case by Case on Paramount Plus. Be sure to rate and review and let us know which cases you're following and which cases you'd like us to follow. It was a gruesome discovery off a dirt road in Georgia. Hunters had found a body. Was it immediately clear to you that this woman had been murdered? Yes. But who was this mystery woman in the woods? That looks like Mindy. 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