The Pastor's Secret: The Murder Case Against Caleb Flynn — Case by Case — "48 Hours" Podcast

[00:00:00] Speaker 1: in 2013 tip cd ohio music pastor caleb flynn auditioned for american idol the person that [00:00:15] Speaker 2: inspires me to be informer i guess would say uh would say the lord well he also credited his wife [00:00:22] Speaker 1: 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 i love her well 13 years and two children later caleb flynn was found [00:00:36] Speaker 3: guilty of her murder we the jury in this case being duly impaneled and sworn find the defendant caleb c flynn guilty of aggravated murder as charged in count one of the indictment prosecutors [00:00:51] Speaker 1: allege 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 nine 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 flynn was sentenced to life in prison without parole on monday october 5th 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 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 [00:03:02] Speaker 4: yeah such such should have been such an idyllic life it appeared from the outside that you know the small town growing up like that two beautiful daughters it's just the community is definitely [00:03:13] Speaker 1: feeling a loss um 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 [00:03:34] Speaker 4: 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 two hundred thousand dollars a year and you know there was 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 caleb said she showed caleb a spreadsheet of the potential of the company the growth that 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 that caleb was the sole beneficiary of a hundred thousand dollar insurance policy on his [00:04:19] Speaker 1: wife's life uh it wouldn't be the first time that we heard of an insurance policy possibly you know [00:04:27] Speaker 4: feeding into a motive definitely this wasn't a gigantic one like in some cases but it was significant [00:04:33] Speaker 1: right right okay so let's give people sort of a sense of the timeline um going back to the day of ashley's murder around 2 30 a.m in the morning of february 16th caleb calls 9-1-1 to report that an intruder broke into his home uh they actually played that uh call in court i want to play some of that [00:04:51] Speaker 5: for the listeners to hear somebody broke into my home somebody broke into my room looking at my wife my wife she's got two shots to her head there's blood everywhere oh my god oh my god oh my god [00:05:04] Speaker 1: listen i mean this does sound like a man who has stumbled upon an incredible scene he's he's very emotional you've listened to a number of 911 calls uh in your career i'm sure what's your take on his [00:05:19] Speaker 4: demeanor oh first of all he's quite the the waterworks of the crier um he actually made a reference to that earlier 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 and he was weeping all through the trial another very important part of that uh that i noticed is he 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 to be able to determine the amount of shots and a messy crime scene like that it's uh these are crocodile tears as far as i'm [00:05:59] Speaker 1: concerned oh that is such a great point you know she's there in a pool of blood like how would he [00:06:04] Speaker 4: know two shots it's not something you check for when you're trying to save your your dying wife or your [00:06:10] Speaker 1: 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 um so many details and i gotta 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 [00:06:54] Speaker 4: they've got plenty to work with a trial oh they had tons to work with here and mario it's the evidence was just not consistent with his story this man expected us to believe that at a an opportunist a homicidal opportunist broke into his garage went 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 he's probably never seen a cop show on tv because he just made so many so many errors there that uh in in trying to recreate what he thought was going to be a you know 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 the they found particles on the wrong side of the door anyone breaking in from the outside that that this was clear signs of a [00:08:11] Speaker 1: staged uh home invasion if it had been in a home invasion i mean what would they have seen the door would have been bent it pushed in in a different direction what else would investigators be looking for to prove that someone else had been in the house first of all it's it's the entire house becomes [00:08:29] Speaker 4: a crime scene the outside becomes a crime scene you know they did tape it off i saw the uh 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 it's none of it adds up to an investigator or i'm sure to anybody listening to the show that uh that has any kind of of reasonable uh you know knowledge of what happens at a uh at a home invasion nothing adds up here to me [00:09:03] Speaker 1: you know 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 i'm a parent if i'm feeling under the weather the last person i'm gonna cuddle up with is my kid and risk getting them sick so right away i thought that doesn't make any sense at [00:09:32] Speaker 4: all i'm with you exactly and you can look at the bed because the body one camera picked up the picture of the bed there's stuffed animals strewn across it you know 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 the word contrived comes to mind you know yeah he thought maybe laying in the on the couch where his wife asked him to go supposedly for coughing in the bedroom would have been too obvious that a bad guy passed him and shot the way it's just such a so contrived [00:10:05] Speaker 1: and we should tell people that the flynn girls are now uh they're 12 and they're 10 and they're being taken care of uh by their grandmother and their aunt but you do see photos of the kids room and it's tight it's kid-sized bunk beds like a grown a grown man i was gonna say grown ass man a grown man [00:10:25] Speaker 4: 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 you know delay it's just it's ridiculous um so i will say you know [00:10:40] Speaker 1: it is the ridiculous nature of the story that is is having me sort of giggle a little bit but this is a 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 that in the days after their mother was shot i want to play a little of that sound here [00:11:06] Speaker 6: i asked her why she was nervous and without telling me what she said what did you do next i marched her down to her dad and said she she's afraid to tell the truth tell her to tell the truth what did he say [00:11:24] Speaker 1: 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 um it's unsettling so i wonder if there's more to take [00:11:39] Speaker 4: from what the grandmother had to say this is such a horrible thing for these poor kids to have gone through you know of course i would have been curious to say to see what they have would have said during an interview or if they were put on the stand i'm glad they weren't no nobody no child should have to relive something as 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 uh you know 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 know 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 you know his knowledge of them [00:12:38] Speaker 1: so herman we've had you on the show before to talk about cases where there's nobody found right no body cases that those are tough in this case you know 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 [00:12:58] Speaker 4: like caleb oh definitely it takes a lot of the guesswork out 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 and it's circumstantial evidence so it's one less thing for the uh for the prosecutors to have to replace this case had tons and tons of of uh circumstantial evidence including 107 000 messages that come into play because they 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 actually 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 uh the center console there i i really wish that they had found that gun you know obviously it didn't matter in the big scheme of things but he 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 it's it's easy and um it's very difficult for police officers to find you know the hiding spots that nobody knows about they're not tearing the house apart from you know all over the place so let's talk about the [00:14:21] Speaker 1: additional evidence uh that investigators found that was inconsistent with caleb's testimony [00:14:28] Speaker 4: 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 this 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 you know technology on those drones they tried a 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 they thought that they were walking into and no disrespect to these officers it's a 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 his initial story and his initial report and they'd have to because what if what if he's telling the truth you can't let a uh the [00:15:46] Speaker 1: 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 can see [00:15:56] Speaker 4: 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 doodle that are walking around that would just completely disregard and sleep through a door getting kicked in in a house guns going off and anything else it's just [00:16:25] Speaker 1: ridiculous they'd be all over the place and you mentioned the text messages there's and we're going to get into that in a little bit but there's a lot of sort of digital evidence the 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 [00:16:53] Speaker 4: it's crazy to me that yeah you're right that that's something that he just definitely i think he just doesn't understand the concept of an investigation of what's going to happen here of how much scrutiny is going to be put on all of these these pieces of information from an investigative standpoint now [00:17:10] Speaker 1: 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 want to talk a little bit about what the footage showed but also kind of why it's important in some of these cases to [00:17:39] Speaker 4: have the jury actually go to the crime scene the jury view is we call it a field trip sometimes uh there's nothing that can replace having a jury stand where the incident happened you know there's just a different perspective there that you're not going to get from body cam video 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 where the crime actually happened the proximity to the bedroom to the garage door where the children were sleeping you know it's just it's such a a vital part of this case i think for the jury to really understand [00:18:17] Speaker 1: where this falls apart but what the body cam footage does give you is what was happening in [00:18:21] Speaker 4: the moment and what do we see oh i'm i'm addicted to body cam videos it's like me reliving parts of my 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 an aside the garage door had also been open and i think you know 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 you know ties to somebody going through a traumatic series of events or somebody that's just done something that's really horrific it's it's hard to read he cries this guy you know he cries at the drop of a hat caleb was really sobbing and 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 waterworks there [00:19:36] Speaker 1: so now i want to talk about motive and we talked a little bit about money but really what the prosecution argued was that uh he wanted out of his marriage that caleb was 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 [00:19:55] Speaker 4: have been a pretty passionate affair as well yep 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 a passionate affair going on [00:20:06] Speaker 1: 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 [00:20:27] Speaker 7: about numbers the years in between said love has a limit said love's not that clean [00:20:40] Speaker 5: but age never mattered when it was you and me we were proof that forever was something you feel not see [00:20:53] Speaker 1: okay so clearly music is his love language um this is sort of a baffling moment in court um in fact some people in the room were trying to hold back laughter like i said this this doesn't necessarily isn't necessarily evidence connected to the actual crime but it was still significant [00:21:12] Speaker 4: 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 it's a good move by the prosecutors they they would have known that the everybody's eyes are going to be rolling and you're suddenly listening to these lyrics it's uh it's deplorable you know just the theatrics behind this botner addressed the song in her testimony and i [00:21:38] Speaker 8: think we have some of that to play here i think that this song was was rich to show how much you [00:21:50] Speaker 1: cared about me to be right now baby nothing 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 didn't really matter because ashley does discover that he's having an affair they the couple they are on a cruise to celebrate their 15th anniversary and she reads text messages and that's how she finds out which must have been devastating uh for her um herman how were prosecutors able to connect [00:22:36] Speaker 4: caleb's infidelity though to ashley's murder so caleb and alia sent over a hundred thousand 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 you know that they were in an intense passionate affair and it's important to note that this is cheating and the messages show that you know 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 text caleb i want to get this right quote i want to kill her caleb end quote to which he responds quote that makes two of us end 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 end quote it reminds me of there's an expression in the fbi that you know the e in email stands for evidence and that's 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 [00:24:22] Speaker 1: mean they just stopped short of i did it i mean it literally like 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 uh too late right um so she actually reads the text messages from just hours before the events on february 16th she read them in court i want to play some of that sound [00:24:54] Speaker 8: i said you're about to be free he said i choose you alia you're 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 [00:25:08] Speaker 4: you are more than enough but um 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 [00:25:21] Speaker 1: october the 5th caleb was sentenced to life in prison without parole uh now during the sentencing hearing her sister kayla kite had a few words uh for caleb and i want to play some of that sound [00:25:36] Speaker 6: a man i used to call my brother when ashley died and we learned you were responsible we were as shocked as anyone we trusted you we believed in you we honestly would have laid down our lives for you and i want you to know something else i do forgive 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 by filling my heart with hatred and bitterness i'm i'm always so impressed by people who have the [00:26:14] Speaker 1: ability to forgive when it's not like he's taking ownership in any way um i agree a hundred percent i don't forgive i i would find it very hard to um we also heard from her father who spoke directly to the judge [00:26:31] Speaker 9: saying this you are when we while we choose forgiveness for our own hearts we still desire absolute justice perhaps because of the violent nature of her murder compounded by a lack of responsibility confession or remorse we as a family ask you to sentence 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 a friend and a loving mother and the consequences should match [00:27:07] Speaker 1: the lifelong impact of his loss a loving mother and perhaps um some of the most heart-wrenching testimony came from a statement uh from one of the flynn girls the letter was written and then read in [00:27:23] Speaker 10: 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 with all her heart she was my best friend and then he chose to kill the only mother i ever had i miss her so much so so so much [00:27:52] Speaker 1: 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 watch [00:28:03] Speaker 4: him cry during this and that's probably the the most appropriate those those had to be real because anybody who's a father or parent listening to those words from their own daughter that it's right out of the twilight zone as far as torture is concerned 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 [00:28:27] Speaker 1: carrying that for the rest of their life my my hope is and it seems like they have a strong family structure around them and that will probably help tremendously it will never fill the void but it certainly appears as if these young girls are very well loved um this was a good conversation herman it's always great having you join us thank you thank you appreciate it we will be back next week with another episode of case by case for our 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