‘Crying’ Pastor’s BIG Money Question: Who Gets Wife’s Insurance Now?

"I am not why I'm not a white wife." It is one of the most shocking cases we have ever covered, and the fallout from Caleb Flynn's murder of his wife Ashley is far from over. "Did you really even think about how much pain you would bring your own two daughters?" By the way, Ashley Flynn was the best thing that ever happened to you. "You had the best life ever." Caleb Flynn is starting his new life chapter as a prison inmate in a maximum security facility. His daughters, they are living with Ashley's family, but the convicted killer's family appears to still be by his side, and there's a life insurance policy that needs to go somewhere. We have the new court filings laying out a new layer of drum in a case that has left so many people stunned. We're on the case. Presented by Longcrime, I'm Chris Stewart. Caleb Flynn went from a one-time American Idol contestant and pastor, husband, father, to Ohio inmate number 8865687, and we are learning some new information about his life behind bars, but also for the people he left behind because there is a life insurance policy that has a payout of more than $100,000 that has to go somewhere. We have new court filings that claim a life insurance company is asking a judge to determine where the money is going to go. This was a policy that Caleb took out on Ashley back in 2016, long before his affair with that woman, Alia Botner, and Caleb is the sole beneficiary of this life insurance policy. So where does the money go? Because legally, he can't get it as a convicted killer. What about his kids? What about Ashley's family? Could his family get it? Well, all of this doesn't appear to be that simple. Now, we're going to talk about that part of the story here in just a moment, but I want to get into where Caleb Flynn is now and frankly, how he got there. My wife, she got two shots to her head. That's the 911 call that started everything in this case. February 16th, tip city, Ohio, north of Dayton on Cunningham Court, quiet cul-de-sac in this quiet community. It was after midnight, Caleb Flynn calls 911 and he is hysterical because he says that someone broke into their house and shot his wife twice in the head while she was sleeping in her bed. Is she breathing at all? I don't think so. Caleb Flynn body camera video shows was hysterical when police got on scene. Are you able to tell me her information? Yeah, I know this is really difficult, okay? Thank you. What's your name? Caleb. I'm sorry, okay? You can call family, by the way. They just can't come in this house. They're not going to be able to come like near the house or anything like that. I'm going to call it mom. My parents will be in Minnesota. Okay, before you do that, can you do me a favor? Okay. What's her first and last name? Ashley. What's her last name? Flynn. Okay, that's a little why you then. Hey guys, before I get back to this episode of On the Case, need to switch gears here real quick. Running a business is tough enough, but why make it harder doing things manually or relying on dozens of apps that don't talk to each other? That's where our sponsor Odu comes in. Odu is an all-in-one business management platform with a full suite of integrated apps that seamlessly connect all your operations from sales and accounting to manufacturing and even shipping. Odu can automatically generate professional sleek looking sales orders, invoices and vendor bills, and it can automatically assign sales teams, send email updates through each sales stage and even use AI to pull reports that help with your decision making for manufacturing. Their apps can sync inventory with real-time production and purchase updates so you never run out of stock. And when it comes time for accounting, that is also fully automated. Odu can create invoices, track expenses, and even summarized data with AI to save you hundreds of hours. In the best part, you can choose your apps and even build custom workflows so it's all fully tailored to your business's needs. Take your business to the next level by consulting with an Odu expert today for free at odu.com/OTC. Three days after Ashley's murder, police arrested Caleb Flynn. They said his story just did not add up. An evidence that trial showed that Caleb Flynn was lying. He said someone broke into their house, but evidence, according to investigators, showed that the door that he said the intruder came through was actually damaged from the inside. And that was just a piece of the story that prosecutors told. We also learned that Caleb Flynn was having an affair and it was one that went back to March of 2024 with a woman named Alia Botner, a worship leader at his church who was roughly half his age. The two of them shared more than 100,000 text messages during the affair and they were nasty. They called Ashley Flynn nasty names, even calling her the spawn of Satan. And remember, these are people who identified very much with their faith. I want to kill her Caleb. You said that? Me. That was part of Botner's testimony on the stand. And this affair, it was a lot to take in at trial. Not to mention, of course, the AI generated music that was played for the courtroom that Caleb wrote for Alia. Early mornings, late nights, jokes in our head. The first time I saw you, room disappeared. I love it for a sight, even though I was scared. Yeah, it's hard to forget that. Botner was never charged in connection to Ashley's murder. She was house sitting for her pastor on the night that Ashley died. The night before the shooting, Caleb texted Alia Botner that he chose her. She testified that she thought he was talking about a divorce and leaving Ashley for her, but a jury determined that Caleb Flynn was talking about killing his wife. We eat the jury in this case being duly empaneled and sworn. Find the defendant Caleb Seiflin guilty of aggravated murder as charged and count one at the indictment. Caleb stuck by his story, though, still is to this day. He says an intruder killed his wife, law enforcement never found the murder weapon on October 5th and Ohio judge sentence Caleb Flynn to life in prison without the possibility of parole. Caleb's two daughters, they're 10 and 12 years old. They were inside the house at the time of the shooting and they now live with Ashley Flynn's sister. Caleb Flynn still stands by his innocence. He's appealing as guilty verdict. It seems like his parents are still in his corner. They told a local TV station after the trial. They felt that his defense did a bad job that we didn't get the truth. The jury, of course, saw it the other way. And the fact that Caleb Flynn's family is still by his side that could make some civil issues complicated, which we'll talk about here in just a moment. And obviously there is a lot to this trial that we can't get to just in this episode. We have a lot of the evidence that was shown at trial, a lot of the testimony, a lot of the coverage that we had of this trial from earlier this year that you can check out over a long crime plus, head over to the court TV case files. We have one there for Caleb Flynn with a ton of information. And on the app, long crime plus, you get to also watch shows both from long crime and court TV add free. And we do have a fall sale. I want to mention that ends today, the day that we're recording this on Wednesday. And for the last day, you can use my promo code OTC fall to get 25% off an annual long crime subscription and enjoy a full year of true crime commercial free just 4499 for the year. So head over to longcrimeplus.com and subscribe today. But let's get to this issue now related to this life insurance policy. So banner life insurance just filed these documents in Ohio court asking for a judge to figure out who is going to get Ashley Flynn's life insurance policy. It lists Ashley's sister, Ashley's brother-in-law, who is also raising the two Flynn children, Ashley's parents, and then the children of Ashley and Caleb. And it also names Caleb's parents and Caleb's brother as defendants in this case. Now Ashley's sister, Kayla Kite, and she testified at trial. She is now the guardian of the Flynn daughters. And she has applied, according to these documents, to be the administrator of her sister's estate. The document also says that Caleb's mom has power of attorney for her son, who of course is now a prisoner of the state of Ohio. The insurance company says in March of 2016, this life insurance policy was taken out for Ashley. And this is the letter that the company sent to Caleb once that policy was in place. Four days after Ashley's death in February of this year, Kayla, her sister contacted Banner Life Insurance with the intent to claim the more than $100,000 in the policy. Now, if Ashley had died and Caleb was not responsible, he would be the person who would be able to claim the insurance money because he's the sole beneficiary on the policy. But Ohio has what's called a slayer statute, which means a convicted killer cannot get the money from a victim's policy. The Life Insurance Company says that all the people named in the document, both Ashley's family and Caleb's family, have quote, an actual or potential interest in the proceeds. The insurance company is also asking the court that they be allowed to deposit the payout, which is $100,759.77 with the clerk of court. I'm gonna bring in Elizabeth Voulie, head of legal affairs here at Longcrime to help break down kind of the legal issues here and help us sift through that legal ease here in just a moment. But before I get to that, I also wanna talk about what we've been learning about Caleb Flynn and what he has been up to since his conviction. Now, after that conviction, before he was sentenced, he was deemed a violent offender of the state of Ohio. - Mr. Flynn, as a result of being convicted of aggravated murder and the four other murder charges or murder convictions, you are required to give a duty to register as a violent offender, 'cause those are qualifying offenses. As a violent offender, it is presumed that you must enroll in the violent offender database for a period of 10 years. As a qualifying offender, you must provide information to the sheriff of the county and the residents that you will maintain at the time of enrollment. You must enroll annually and you must notify the sheriff if any change of address within three days. Prosecutors may file to extend an offender's enrollment duties beyond the 10 year period and specified circumstances. - Now, since he is serving life in prison without the possibility of parole, it really could be more symbolic that he has been added to a database for violent offenders in Ohio, which means if he were ever to get out of prison, he would have to notify the state of where he's living very similar to a sex offender. Now Flynn has filed a notice of appeal and he is not going with private counsel this time in his attempt to overturn his conviction. A public defender has been appointed to oversee that process. The name of that attorney is Jacob Cytle. Flynn is currently living at a maximum security prison in Ohio, the Toledo Correctional Institution. It's more than two hours away from where he once lived in Tip City. This maximum security facility has more than 1200 inmates at capacity and it is driving distance from where Caleb Flynn once lived. But when I think about this case, I also think about the victim impact statements that were made at his sentencing and specifically the one that was written by his oldest daughter, read by his mother-in-law. - You made me feel like an idiot thinking that I could trust you. But God has been working through me and I have changed. Also, our family has never been stronger. And through all of what you put me through, God is gonna work something out for good. And by the way, I don't plan on coming to see you. Flynn. - So let's dive into this. The head of legal affairs. For us here at Long Crime, Elizabeth Ulyh joins me today. Thanks as always for doing this. You're good to see you. So how might, you know, reading through this court document, how does the court figure out who might get this life insurance policy? - Yeah, thanks for having Chris. So it's a really good question. So here, you know, when the terms of who's going to be the beneficiary or not clear cut originally they were clear cut, right? Because Caleb Flynn was deemed the sole beneficiary. Obviously this layer statute comes into play and complicates that. So really what happens is now that this has sort of been submitted to the court or the insurance company is trying to submit it to the court. What courts look at is, you know, many different factors, what state law dictates, what the language of the policy states, you know, because a lot of time specific policies will have, not just list one beneficiary, but if they, you know, if there's a situation where a beneficiary is disqualified like here, there's usually an order of other people that will come after. So, you know, is that the, the defendant's children, is it the estate, is it other members of the family that will be the beneficiary? So that's really the biggest thing that courts look at is what's the language of the policy as well as, you know, what the state law dictates and, you know, other evidence that's submitted. - So when you look at the details of this case and it's horrible, you know, Ashley Flynn was this mom, they have two young kids. Those girls are now being raised by Ashley's sister and Ashley's brother-in-law. I think as the public, you would look and say, like let's make sure those girls have the resources that they need, but at the same time, and we haven't heard from the Flynn family and what they plan, what they plan to do, but in terms of this, this document, it lists Caleb Flynn's parents, his mom now has power of attorney, and his brother, because he only has one sibling, as people who could have a shot at getting this money, like how might Caleb Flynn's family like have that type of access to this money, you know, at the same time when you have Ashley Flynn's family, 'cause I know he's the sole beneficiary, so I guess my question is like, how does that factor in that there was only one person on this life insurance policy that was taken out in 2016 that it was Caleb Flynn and Caleb Flynn alone? - Yeah, it's really interesting. And also the caveat too is that he's the sole beneficiary and he's also the policy holder. So he's the one that purchased the actual policy, you know, at the time his wife was a homemaker, he purchased the policy with her consent, and that's actually pretty common, especially with married couples where, you know, maybe one person's at home with the children and then the other person's working. So typically the way that it happens is if a beneficiary is disqualified, a lot of times it will next look at who the policy owner is and revert to that, but in this case, it's him. So sort of cancels each other out. And now, you know, what the insurance company has done is basically provided this and filed this interpleeter to ask the court, hey, you guys basically do get out here. They're anticipating that all these parties are gonna try to, you know, make claims to the actual insurance proceeds. And I think the way that the courts look at it is, you know, again, what the language of the policy states, you know, if it's going to his state and him being the beneficiary, you know, that would potentially mean who's managing his estate. So, you know, whether it's his mother is the power of attorney who's been deemed the, you know, executor of the estate, all of that. It's really centralized on what the language of the policy says, but then also what roles are his family taking when it comes to the actual estate. - And you think of these slayer statutes? And I'm sure they differ from state to state, but, you know, I remember in like the Nick Reiner case is that's been playing out in California. You know, he wants access to a trust, but of course he's accused of killing his parents. In this case with Caleb Flynn, he's been convicted of killing his wife. What do you see when you look through the slayer statute and Ohio and how it factors in the vest? - Yeah, it's interesting that you brought that up because that's one of the first things I thought of, you know, the slayer statute is very common. All around 47 states, so nearly all states have some version of a slayer statute. And there's a lot of overlap with this and Nick Reiner, obviously, with some caveats, as you mentioned. But basically, you know, the language of the Ohio slayer statute states very clearly. If you've been convicted of murder, manslaughter, you are not able to financially benefit from that crime. In this case, what makes one of the things that is made really clear is that there has been a plane and clear conviction Caleb Flynn was convicted of murder, so that would disqualify him from being able to financially benefit. And so that language is really plain on its face. And then the California statute, it's a little bit different. That's what's governing the Nick Reiner matter right now. You know, it has language about if you feloniously and intentionally commit a crime, you know, you're not able to pursue family trusts and proceeds in that way. So the wording of the two is a little bit different, but I think the Ohio statute is really clear that there's been a conviction of murder, you're disqualified, hence why all of this has now come into play. And you know, if the slayer statute wasn't activated, the insurance company probably wouldn't have needed to file an inter-pleter, but when situations like this happen, it's actually pretty common that they do that. - Well, and it also, it seemed to like pretty, and you know, when you're doing with insurance companies, it's rare, I feel like you're like, oh, that makes sense. But like in this case, you know, the insurance company pretty much saying like, look, we have this more than $100,000. This was the policy Ashley Flynn loses her life. And the insurance company is, it seems like pretty much is saying like, let's give the money to the court, let the court decide, but for us as an insurance company, we've kind of fulfilled legally our responsibility to the policy holder, even though the policy holder was Caleb Flynn, but just in terms of Ashley Flynn, here's the amount of money it had, and then putting this money forward. It seems like it's a pretty straightforward, at least from the insurance company's part of it, pretty straightforward what they're doing here in these documents. - Yeah, it's really straightforward, and it's actually very much standard operating procedure. So, you know, in cases where there's a clear beneficiary, Slayer Statute doesn't come into play. The insurance company would need to do this. They would just allocate the money, however, it's listed in the policy here, because the Slayer Statute comes into play. That's when insurance companies file an interpreter to basically tell the court, okay, you guys basically handle this. These funds that are being contested, we want to deposit that directly with the court and allow the parties to basically duke it out. And one big thing and one key reason why insurance companies do that is because they also get a discharge from that. So once they deposit the funds and give full discretion to the court to decide who should be getting the proceeds here, they are protected from liability. Because also insurance companies are not judges. They can't unilaterally decide who's going to be awarded the insurance proceeds when there's complications like this. So that's when they appoint the court to be able to do that. And they also know if they were to act as a judge and give the proceeds to one family versus the other, lawsuits would result, one family who didn't get the proceeds would sue or vice versa. So to avoid all of that when situations like this happen, insurance companies almost always often file an interpreter to basically tell the court, okay, you guys basically take it over from here, we're depositing all these contested funds and hopefully be getting the protection from liability that they're seeking. - And we'll see what happens next on that part of it. I mean, Caleb Flynn at this point, he's been appointed a public defender. He says he's going to appeal, he's filed a notice of appeal, he used a private attorney for his murder trial, but in terms of the appeal process, he is serving life in prison without the possibility of parole, the jury decided it. What exactly does the appeal look like? Is it necessarily saying, hey, we found evidence that he didn't do it? Like what would a successful appeal look like for Caleb Flynn? And I know that's a high bar and you know, there's nothing that has been brought forward to this point that would make you believe that anything was wrong with this trial. - Yeah, it's a great question. So with the appeals process, it's a very new on specific process, a lot of times people retain special counsel called the Pellet Council because they're more knowledgeable in terms of what documentation you have to file, what are the standards for the motions. A lot of times people will pursue an appeal stating that evidence that should have been presented the first time a trial that proves their position was not made available and it should have. Sometimes they'll point to ineffective assistance of counsel, saying that maybe their counsel had not argued a point that they should have or missed something. Really, I think the most successful appeals that I've seen just on all cases is a key piece of evidence that should have been introduced that was not or that was available the first time around or a key piece of evidence that becomes known and available to all the parties after the conviction. A lot of times that really is what persuades judges, but as you mentioned, it is a very high bar. It's, I don't know the exact percentage success rates of appeals but it's not super high, it's a high bar and there's a lot that Pellet Council has to prove to show that the conviction that was made should be overturned. Especially in a case like this where it's a matter of public interest, this is violent crime, it's murder of very high stakes, so it's going to be a tough process, I think. And it feels like those appeals, it doesn't happen overnight. I mean, you know, like Alec Murdoch, like in his case, I mean, that was years ago that he was convicted and then now of course there's major developments there where he's going to end up getting a new trial, but I also think of like Carmelo Anthony who has several attorneys working on his behalf and that case out of Texas, as he tries to appeal his verdict. I mean, it feels like in the appeals process that without a doubt, if there's some piece of information that comes out that we didn't know about with Caleb Flynn in one day, it's like, oh my gosh, this guy was innocent the entire time not saying that that's going to happen, but that would happen years down the line. Yeah, precisely, one, because as we all know, courts are very backlogged, so that's one practical reason and also two, it takes time, there's a lot of motion practice that has to happen with an appeal. There's a high bar in terms of demonstrating why you are entitled to an appeal, why the initial conviction was incorrect, what evidence was made available now, you know, what judges or counsel should have looked at, that maybe was not looked at. So I think one just practically, it takes a long time, just because of the court system and how inundated the court system is, and then also to just because of all of the motion paperwork that has to be filed and, you know, the different pieces of evidence and aspects of the case you have to prove, so I think it's going to be a while. And then one more question I have for you is it's kind of related to the private counsel versus public defender part of it, because Caleb Flynn had Patrick Mulligan was his defense attorney for this trial. This was someone who he retained after he had been arrested for the murder of Ashley in February. And, you know, attorneys are very expensive. I mean, you know how much attorneys, attorneys can cost no matter what the issue may be, how in a case, more generally speaking, when someone is convicted of a crime like Caleb Flynn, or he's not going to work ever again, he's going to be in a prison, you know, it's not like you're going to sue Caleb Flynn because, you know, Caleb Flynn, if he doesn't pay you for your services, like, you know, what more can be done, he's in prison for the rest of his life. Typically, in these type of murder cases, how do attorneys get paid? Yeah, so typically, you know, when you have a defendant that has some sort of already available income or passive income, a lot of times they can make arrangements with their appellate counsel and legal counsel to have them be paid beforehand. But when that's not a possibility, a lot of times people look to their family, friends, sometimes, you know, people will put up money, you know, we see a lot of examples of people putting up bail money or legal funds or things like that. Also, you know, when people can't afford to pay directly on their own or to solicit family members or friends to help them out, they'll go the route of a public defender. And that's really what it was designed for, is that the idea that everyone's entitled to a fair trial, to a potential appeal, if they feel an appeal is warranted and they want to pursue that. And just because someone's financial status may not be high, doesn't mean that they're not afforded the right to counsel. So a lot of times with filing appeals, you know, they'll be able to seek the assistance of a public defender. And then the way that they get paid is obviously or through, you know, their public employee, government funding, things like that. - Yeah, and we'll see what happens next in this case. Certainly, now you have a civil side of it figuring out, you know, this life insurance policy and what may happen next involving Caleb Flynn. Elizabeth Voulay, thank you as always for taking the time to be with us. Here, on long crime and on the case, it's great to have you. - Thanks so much, Chris, great to be here. That will do it for on the case presented by long crime. I'm Chris Stewart. We'll see you next time. (upbeat music)