Show full transcript 0:57 Toyota, let's go places. 1:00 You know that thing where you get an amazing pair of shoes 1:03 at a really great price and want to tell everyone about it? 1:06 Yeah, so do we. 1:07 Here at Designer's Shoe Warehouse, 1:09 we'll give you something to brag about, 1:10 like the latest styles from brands you love, 1:13 or the trends everyone's obsessing over, 1:15 or shoes that make you feel like, well, you. 1:18 So go ahead, show off a little, 1:20 find shoes that get you at prices that get your budget. 1:23 Head to your DSW store or DSW.com today. 1:26 Okay, DSW, let us surprise you. 1:34 In 2013, Tipsy D, Ohio music pastor Caleb Flynn 1:38 auditioned for American Idol. 1:41 The person that inspires me to be an informer, 1:44 I guess would say, would say the Lord. 1:47 Well, he also credited his wife, Ashley Flynn, 1:50 for giving him the push he needed to try out. 1:53 I love my wife more than anything. 1:56 She is very, very pretty. 1:58 Just, oof, I love her. 2:00 13 years and two children later, Caleb Flynn was found guilty of her murder. 2:06 We, the jury in this case, being duly impaneled and sworn, 2:10 find the defendant, Caleb C. Flynn, guilty of aggravated murder, 2:15 as charged and count one of the indictment. 2:18 Prosecutors alleged that on the morning of February 16, 2026, 2:22 Caleb fatally shot his wife in their home and staged a home invasion to cover it up. 2:27 The nine-day trial revealed body cam footage from that day, bullet casings from the murder 2:32 weapon, and revealing testimony from Caleb's lover, a member of the family's church, 2:39 much younger member. 2:40 The jury took just over two hours to find Caleb guilty of nine charges in total. 2:46 This includes three counts of murder, two counts of felonious assault, and three counts 2:51 of tampering with evidence. 2:52 Flynn was sentenced to life in prison without parole on Monday, October 5th. 2:58 I'm 48 hours correspondent Ann Marie Green and this is Case by Case. 3:02 So returning to the show today is 48 hours consultant Herman Weisberg. 3:08 Herman is a private investigator, former NYPD detective and the managing director of Sage 3:13 Intelligence Group, where he oversees investigations. 3:17 Herman, it's great to have you back. 3:18 Thanks for joining us. 3:19 Great to be here. 3:20 Thanks for having me, Ann Marie. 3:21 Let's start things off, Herman, by talking about the Flynn's, just who they were. 3:26 You know, Ashley's death was devastating to her family. 3:30 She left behind a sister, Kayla Kite, her mother, Jill Smith, her father, Todd Smith. 3:35 She was also a mother. 3:37 She left behind two girls ages 10 and 12. 3:40 So Ashley grew up in Tip City. 3:43 She ended up staying there basically most of her life. 3:45 If she met Caleb when she went away to college in Cleveland, Tennessee at Lee University 3:51 and then the two got married the same year that Ashley graduated, that was 2010. 3:55 Ashley went on to become a substitute teacher and volleyball coach in the very school system 4:01 where she graduated from. 4:03 I think this is almost sort of like a Norman Rockwell sort of thing, right? 4:07 Small town girl goes off to college, marries her college sweetheart, comes back to her 4:11 hometown and becomes this teacher that has this, you know, impact on all these kids. 4:17 The Tip City school system posted something when she died on Facebook and it sort of gives 4:21 you a sense of the kind of lasting impression that she had. 4:24 They wrote, she was known for her beautiful smile, warmth, kindness, and the positive 4:29 impact she had on so many both in and out of the classroom and on the court. 4:34 Yeah. 4:35 Such should have been such an idyllic life. 4:37 It appeared from the outside that, you know, the small town growing up like that to beautiful 4:43 daughters. 4:44 It's just the community is definitely feeling a loss. 4:47 And I think also what sort of adds to kind of the betrayal, I think, is that Caleb was 4:55 close to Ashley's family. 4:56 He worked in the family business. 4:59 They welcomed him in. 5:00 Ashley's father had a flooring and furnishing company. 5:03 Caleb was a salesman there. 5:04 Running a business together, I would imagine that they're all pretty close knit family. 5:09 It can raise tensions as well, especially when it comes to money, but Flynn reportedly 5:14 was doing pretty well. 5:15 He was, as a salesman, he was making about $200,000 a year, and I know there's a nice 5:21 future there. 5:23 Ashley's father was preparing to retire, and he planned for Ashley, her sister Kayla, 5:27 and their spouses, including Caleb, to inherit the business and continue it. 5:31 In court, Kayla said she showed Caleb a spreadsheet of the potential of the company, the growth 5:38 that was supposed to occur, and he definitely took an interest like in this, as he should 5:43 have. 5:45 This also shouldn't be ignored that Tip City Police testified that Caleb was the sole 5:49 beneficiary of $100,000 insurance policy on his wife's life. 5:53 It wouldn't be the first time that we heard of an insurance policy possibly, you know, 5:59 feeding into a motive. 6:01 Definitely. This wasn't a gigantic one, like in some cases, but it was significant. 6:05 Right, right. Okay, so let's give people sort of a sense of the timeline. Going back to the day of 6:10 Ashley's murder, around 2.30 a.m. in the morning of February 16th, Caleb calls 9-1-1 to report 6:18 that an intruder broke into his home. They actually played that call in court. I want to 6:23 play some of that for the listeners to hear. Listen, I mean, this does sound like a man 6:39 who has stumbled upon an incredible scene. 6:43 He's very emotional. 6:45 You've listened to a number of 9-1-1 calls in your career. 6:49 I'm sure. 6:50 What's your take on his demeanor? 6:53 First of all, he's quite the waterworks of the crier. 6:57 He actually made a reference to that earlier in his audition tape. 7:02 He called himself a cry baby. 7:03 So he definitely was aware of that. 7:05 He said he got it from his mom and dad. 7:07 but he was weeping all through the trial. Another very important part of that that I 7:13 noticed is he mentions two shots you know it's just such an unusual thing to say 7:19 into a 911 call and what kind of examination did he do to his wife's body 7:24 to to be able to determine the amount of shots and a messy crime scene like 7:29 that so these are crocodile tears as far as I'm concerned. That is such a 7:34 Great point, you know, she's there in a pool of blood. Like how would he know two shots? 7:38 Something you check for when you're trying to save your your dying wife or you recently assaulted wife 7:45 So in that same 911 call Caleb said that he was lying in his daughter's bedroom 7:51 When he heard the gunshot 7:52 He said that he got up and he noticed his garage side door was open as well as the central call 7:57 Console on his truck where he keeps his gun 8:00 According to Caleb, he returned to the house and he finds Ashley in a pool of blood in the 8:06 bedroom with, as we heard, two gunshot wounds. 8:11 So many details and I got to tell you prosecutors love when suspects give a detailed version 8:21 of what happened because for every point, if they can kind of like discredit that point, 8:27 They've got plenty to work with at trial. 8:30 Oh, they had tons to work with here, Anne-Marie. 8:33 The evidence was just not consistent with his story. 8:37 This man expected us to believe that an opportunist, a homicidal opportunist, broke into his 8:46 garage, went into the center console of his truck, took out a loaded firearm, entered 8:53 murdered a house, went right to the master bedroom, like he knew the place, murdered 9:01 a sleeping woman, and then left without committing any other crimes. 9:05 It just does not add up at all. 9:07 This is a guy that apparently he is definitely not a listener to your show, or he's probably 9:13 never seen a cop show on TV because he just made so many errors there that in trying 9:20 to recreate what he thought was going to be a reasonably perfect crime. During the trial, 9:27 they actually brought that garage side door into court just to show that the handle was broken off, 9:32 but the door did not have damage consistent with the break-in. They found particles on the wrong 9:39 side of the door. Anyone breaking in from the outside, this was clear signs of a staged 9:45 a home invasion? If it had been a home invasion, I mean, what would they have seen? The door 9:53 would have been pushed in a different direction. What else would investigators be looking for 9:58 to prove that someone else had been in the house? First of all, the entire house becomes a crime 10:05 scene. The outside becomes a crime scene. You know, they did tape it off. I saw the 10:08 body worn camera footage. Everything gets examined. You're looking for fingerprints. You're 10:14 looking for a method of exit as well as a method of entry. 10:18 This whole thing was so contrived and so horribly done, 10:23 none of it adds up to an investigator 10:26 or I'm sure to anybody listening to the show 10:28 that has any kind of reasonable knowledge 10:33 of what happens at a home invasion. 10:36 It's nothing adds up here to me. 10:38 You know, even sort of the claim 10:40 that he was lying in his daughter's bedroom, 10:42 also immediately that felt odd to me before even knowing what the evidence 10:47 indicated because he says that he leaves the bedroom with his wife because he's 10:51 sick he goes out to the couch and eventually ends up in his daughter's 10:54 room if you're a parent I'm a parent if I'm feeling under the weather the last 11:00 person I'm gonna cuddle up with is my kid and risk getting them sick so right 11:05 away I thought that doesn't make any sense at all. I'm with you exactly and 11:10 And you can look at the bed, because the body of one camera picked up the picture of 11:13 the bed, there's stuffed animals strewn across it, you know, in a way, let me tell you, I 11:17 have a daughter, I would never mess with her stuffed animals on her bed to lay down while 11:21 I'm sick to go in there. 11:23 This whole thing, again, the word contrived comes to mind, you know, he thought maybe 11:28 laying in the, on the couch where his wife asked him to go supposedly for a coughing 11:34 in the bedroom, it would have been too obvious that a bad guy passed him and 11:38 shot the wife. It's just such a so contrived. And we should tell people that the Flynn girls are now 11:44 they're 12 and they're 10 and they're being taken care of by their grandmother and their aunt. But 11:49 you do see photos of the kids room and it's tight. It's kids sized bunk beds. Like a grown 11:57 a grown man. I was going to say grown ass man. A grown man is not going to fit comfortably in 12:03 that room. A coughing grown-ass man is not going to go into his little daughter's bedroom 12:07 and wake them up and delay. It's just ridiculous. So I will say, you know, it is the ridiculous 12:16 nature of the story that is having me sort of giggle a little bit, but this is a horrible 12:23 thing to use your children kind of as your alibi, right? So the kids were not expected 12:29 to testify. Ashley's mother Jill Smith did take the stand and mentioned that one of the 12:34 daughters seemed nervous in the days after their mother was shot. I want to play a little of that 12:40 sound here. I asked her why she was nervous. And without telling me what she said, what did you do next? 12:46 I marched her down to her dad and said she's afraid to tell the truth. Tell her to tell the 13:01 I mean, it is reasonable that a child would feel very nervous at this time. 13:09 Their mother has been shot. 13:10 It's unsettling. 13:12 So I wonder if there's more to take from what the grandmother had to say. 13:19 This is such a horrible thing for these poor kids to have gone through. 13:23 you know of course I would have been curious to say to see what they have 13:27 would have said during an interview or if they were put on the stand I'm glad 13:30 they weren't no but no child should have to relive something as hard no one 13:34 should have to relive something as horrible as this and kids can testify 13:38 against their parents but the courts obviously try to avoid that you know 13:42 it's protect them I've testified a lot it's extremely stressful I don't care 13:49 who you are how many times you've done it so to put two little girls 13:52 through this to make them relive these traumatizing events. I'm glad it didn't happen. But you 13:57 know you have to wonder if Caleb took into consideration their age and all the other 14:02 stuff just so he can pretend that he was in their room during the shooting. I think he 14:07 definitely took advantage of their age and you know his knowledge of them. 14:17 So Herman we've had you on the show before to talk about cases where there's nobody found 14:22 right? No body cases. Those are tough. In this case, you know, Ashley Flynn is there. There is a body. 14:29 What they don't have is the murder weapon. But having the body, does that make it a little 14:35 easier to convict someone like Caleb? Oh, definitely. It takes a lot of the guesswork out. And 14:43 when you're missing a big component of a case like this, of an investigation like this, 14:47 you need to replace it with something and it's circumstantial evidence. So it's one less 14:51 thing for the prosecutors to have to replace. This case had tons and tons of circumstantial 14:58 evidence, including 107,000 messages that come into play because they had the body. 15:04 A cause of death was very clear. Multiple gunshot wounds to the head. It's an advantage 15:10 that you don't have with a nobody case. According to the coroner, for example, 15:14 Ashley was shot at close range, so that's important. And while they weren't able to 15:19 find a gun and I'm sure they wished that they searched more because it was some place to be found. 15:25 They were able to match the casings and the bullet wounds. They were consistent with Caleb's 15:32 gun that was taken from the center console there. I really wish that they had found that gun. 15:39 Obviously it didn't matter in the big scheme of things, but he didn't really leave the house 15:44 at that point. When you're hiding something in your own home that you know very well that 15:48 lived in for a while, it's easy. And it's very difficult for police officers to find the hiding 15:56 spots that nobody knows about. They're not tearing the house apart from all over the place. 16:00 So let's talk about the additional evidence that investigators found that was inconsistent with 16:06 Caleb's testimony. And like I noted before, everything was inconsistent with his, as far as 16:13 I'm concerned, they're looking for signs of a possible break in and they just weren't there 16:17 there, because there was no burglary that had occurred. An hour after the police first 16:22 got to the scene of the crime, they deployed a drone to try to find suspects. Anybody fleeing 16:27 the scene, they're probably using heat-seeking technology on those drones. They tried a police 16:32 dog to see if they could track down any suspects. They definitely took this, and they didn't 16:37 rule out the possibility that this was a home invasion at the time, because these 16:41 responding officers, that's what they thought that they were walking into. And no disrespect 16:47 to these officers. It's a small department. But I could tell you, I think in the testimony 16:52 of one of them, they had never experienced a murder in this small town. So they're also 16:58 dealing with a church leader, you know, with somebody of respect, somebody crying 17:02 their eyes out on this thing, somebody with two little girls. I'd like to think 17:05 that most police officers responding to a scene like this aren't automatically assuming 17:10 I mean, the husband is a homicidal person. 17:14 So, you know, I could understand why they went out of their way going with his initial story 17:20 and his initial report. 17:22 And they'd have to because what if he's telling the truth, you can't let the perpetrator of 17:27 this get away. 17:28 Right. 17:29 And so there were a lot of little things that they sort of didn't add up. 17:32 And I mean, these are little things, but like they have two dogs. 17:35 You know, and you could see those two dogs, beautiful golden, I'm a dog guy, golden 17:39 doodles, I think they are. They're very alert. This is not dogs don't malfunction dogs bark 17:46 when something's going on and a burglar breaking in kicking down a door and all of this. There's 17:51 not two. I don't think. Tell me if I'm wrong in the comments here, folks, but I don't think 17:56 there's two golden doodle that are walking around that would just completely disregard 18:00 and sleep through a door getting kicked in the house. Guns going off and anything else. 18:04 It's just ridiculous. 18:06 They'd be all over the place. 18:08 And you mentioned the text messages. 18:10 There's we're going to get into that in a little bit. 18:12 But there's a lot of sort of digital evidence. 18:16 The the other digital evidence is. 18:20 His Apple watch, I guess he kept it on. 18:24 And I mean, these things keep track of all of your movement. 18:28 He said he was asleep this entire time. 18:31 The watch said otherwise. 18:32 The old Apple watch evidence, it's crazy to me that, yeah, you're right, that's something 18:38 that he just definitely, I think he just doesn't understand the concept of an investigation 18:43 of what's going to happen here, of how much scrutiny is going to be put on all of these 18:47 pieces of information from investigative standpoint. 18:50 Now the jury in this trial actually toured the Flynn home. 18:53 It's called a jury view. 18:55 If you follow the Clancy case, you will recall that the same thing happened in that 19:00 case as well. 19:00 Well, their authorities also flagged to the jurors that they did not see any evidence 19:05 of forced entry. 19:07 They got another glimpse of the Flynn home in court via the body cam footage that was 19:12 entered in as evidence. 19:14 But I want to talk a little bit about what the footage showed, but also kind of why 19:18 it's important in some of these cases to have the jury actually go to the crime scene. 19:23 The jury view is, we call it a field trip sometimes. 19:27 There's nothing that can replace having a jury stand where the incident happened. 19:32 You know, there's just a different perspective there that you're not going to get from body cam video. 19:37 You know, Martin Scorsese could have directed this film and you're not going to get the same effect as you will when you're standing, 19:43 where the crime actually happened, the proximity to the bedroom, to the garage door, where the children were sleeping. 19:51 It's such a vital part of this case, I think, for the jury to really understand where this 19:58 falls apart. 19:59 But what the body cam footage does give you is what was happening in the moment, and what 20:03 do we see? 20:04 Oh, I'm addicted to body cam videos. 20:08 It's like me reliving parts of my previous career. 20:11 I noticed a lot of things. 20:13 The truck center console was open. 20:15 That's where Caleb claims he kept his gun, which, by the way, that's very irresponsible 20:19 gun ownership to leave a loaded gun. You got a 10-year-old and a 12-year-old daughter in there, 20:23 but that's just an aside. The garage door had also been open. And I think, you know, the biggest 20:29 thing that you can get from that body cam footage was just Caleb's mental state when the police 20:35 officers were present, the way he was acting. He looked like a mess. He was crying hysterically. 20:41 I couldn't understand what he was saying. He wasn't making sense at some point, 20:44 which is all, you know, ties to somebody going through a traumatic series of events 20:48 or somebody that's just done something that's really horrific. 20:53 It's hard to read. 20:54 He cries. 20:55 This guy, you know, he cries at the drop of a hat. 20:58 Caleb was really sobbing and even fell to his knees 21:02 on his porch as Ashley's mother arrived at the home 21:05 that night. 21:06 It was difficult to watch. 21:07 It's really frightening how devastated he seemed 21:10 in this footage and just put on the waterworks there. 21:20 So now I wanna talk about motive 21:23 and we talked a little bit about money, 21:24 but really what the prosecution argued was that he wanted out of his marriage that Caleb was having 21:30 an affair, a year-long affair with a 21-year-old intern, Aliyah Botner, in 2024. He was 38 at 21:37 the time, by the way. It seems to have been a pretty passionate affair as well. 21:42 Yep. Aliyah was around the same age that Ashley was when they got married. 21:47 This case takes a big turn right there when there's a passionate affair going on simultaneous. 21:52 I mean, this doesn't really go to the evidence, it's not sort of significant evidence in terms 22:00 of the crime. 22:01 But there were some AI-generated love songs that were created, a product of this passionate 22:07 affair. 22:08 Some of it was played in court, I want to play some of it now. 22:38 Okay, so, clearly music is his love language. 22:43 This is sort of a baffling moment in court. 22:45 In fact, some people in the room were trying to hold back laughter. 22:49 Like I said, this doesn't necessarily, isn't necessarily evidence connected to the actual crime, but it was still significant. 22:57 Oh, I'm not a music expert, but I like music. 23:00 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. 23:09 They would have known that the everybody's eyes are going to be rolling and you're suddenly listening to these lyrics 23:16 It's uh, it's deplorable 23:18 You know just the theatrics behind this 23:21 Partner addressed the song in her testimony, and I think we have some of that to play here 23:39 So, you know, this is an intense relationship. The couple even got matching Harry Potter lightning 23:45 bolt tattoos. Just as an aside, everyone knows when you get a tattoo, couples tattoos often 23:52 is an indication that things are going to go badly down the road. I'm just saying. 23:56 There's plenty of people with couples tattoos and it's all worked out for them, but sometimes 24:00 it doesn't. Caleb actually put the tattoo in his armpit in the hopes that his wife would never find 24:04 it. Didn't really matter because Ashley does discover that he's having an affair. The couple, 24:09 they are on a cruise to celebrate their 15th anniversary and she reads text messages and 24:16 that's how she finds out, which must have been devastating for her. Herman, how were prosecutors 24:22 able to connect Caleb's infidelity, though, to Ashley's murder? So Caleb and Aliyah 24:27 sent over a hundred thousand messages in the year prior to Ashley's death to each other. 24:31 These messages were extremely telling. 24:34 Aliyah shared many of these exchanges on the stand. 24:37 Prosecutors had her read them for that impact that comes from her voice telling that they 24:43 were in an intense, passionate affair, and it's important to note that this is cheating. 24:49 And the messages show that there's no way around it at that point. 24:52 I mean, Aliyah had initially deleted these messages 24:56 and the FBI questioned her and she lied about it initially. 25:00 The tech show Aliyah asking Caleb to leave Ashley 25:04 and threatening to leave the relationship 25:05 if he didn't follow through on leaving her. 25:08 Caleb refused, citing his family and his reputation. 25:12 At some point, Aliyah texts Caleb, 25:14 and I wanna get this right, quote, 25:17 I want to kill her Caleb and quote, 25:20 to which he responds, quote, that makes two of us, end quote. 25:24 Then about six months before Ashley's death, 25:27 Caleb wrote again to the young woman saying, 25:31 quote, I was up until 4 a.m. last night crying, 25:35 literally trying to think of ways to kill her 25:37 and not go to jail, end quote. 25:40 It reminds me of, there's an expression in the FBI 25:42 that the E in email stands for evidence 25:45 and that really comes into play here. 25:47 this is just gold for a prosecutor. 25:51 Hours after Ashley's death, 25:53 members of their church met at Ashley's parents' house. 25:55 And according to Alia, when she arrived, 25:58 Caleb hugged her and he said, 26:02 it didn't happen the way we thought it would, did it? 26:07 This is extremely telling, very spooky stuff. 26:10 Yes, I mean, those text messages, 26:12 I mean, they just stopped short of I did it. 26:15 I mean, it literally, like just, right? 26:17 Literally two days before Ashley's murder Caleb texts, Aliyah. I'm free 26:22 I'll tell you all but to be careful for us both shouldn't text or leave any trails 26:31 Too late right 26:33 So she actually reads the text messages from just hours before the events on February 16th 26:40 She read read them in court and we want to play some of that sound. I 26:43 Said you're about to be free 26:44 He said, I choose you, Aliyah. You're more than enough. Good night. I said, good night 26:51 praying now. He said, thank you, praying for you as well. Good night. 26:55 Very romantic. You know, you are more than enough. But we know according to prosecutors 27:01 that about two hours after that text, Caleb Flynn shot Ashley twice in the head and then 27:06 he staged a home invasion. 27:09 So in a hearing on Monday, October the 5th, Caleb was sentenced to life in prison 27:13 without parole. Now during the sentencing, hearing her sister, Kaila Kite, had a few words for Kaila, 27:23 and I want to play some of that sound. 27:25 The man I used to call my brother. When Ashley died and we learned that you were responsible, 27:32 we were as shocked as anyone. We trusted you, we believed in you, we honestly would have 27:38 laid down our lives for you. I want you to know something else. I do forgive you. I 27:44 have forgiven both of you and Leah, not because what happened should be ever excused 27:48 or forgotten, and certainly not because there shouldn't be severe consequences. 27:52 I forgive you, because I refuse to allow what you did to destroy another part of my life by filling my heart with hatred and bitterness. 28:00 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. 28:09 I agree 100%. I don't forgive. 28:13 I would find it very hard to. 28:16 We also heard from her father who spoke directly to the judge saying this. 28:20 We are when we, while we choose forgiveness for our own hearts, we still desire absolute 28:27 justice for ourselves. 28:29 Because of the violent nature of her murder compounded by a lack of responsibility, confessional 28:36 remorse, we as a family ask you to send him to the fullest extent of the law. 28:41 He took our daughter, a sister, a granddaughter, an aunt, a cousin, a teacher, a coach, a friend, 28:52 and a loving mother, and the consequences should match the lifelong impact of his loss. 29:00 A loving mother and perhaps some of the most heart-wrenching testimony came from a statement 29:08 from one of the Flynn girls. 29:09 The letter was written and then read in court. 29:13 Mommy was the perfect person, the absolute perfect person. 29:18 What did she ever do to make you hate her so much? 29:22 She loved you and she cared for you. 29:25 She took care of you. She loved you with all her heart. 29:30 She was my best friend. 29:33 And when you chose to kill the only mother I ever had, 29:36 I miss her so much. So, so, so much. You have no idea."
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