True Crime All The Time - Thomas Montgomery Replay

Episode Date: December 29, 2025

We are taking this week off for the holidays, but wanted to put something out in case anyone needed a TCATT fix. This is a fascinating 2022 episode that has always stuck with us. The level of deceit and horrible decisions in this one is off the charts. Thomas Montgomery is currently incarcerated for murdering his 22-year-old coworker, Brian Barrett. Both men were involved with a girl they met on the internet, and Montgomery became enraged with jealousy to the point where he murdered Brian in cold blood.Join Mike and Gibby as they discuss the case of Thomas Montgomery. The more facts that were revealed in this case, the stranger they became. This is a story of elaborate catfishing by multiple parties and shows how bad things can go when people pretend to be someone else online. The story was the subject of an excellent documentary called TalhotBlond.You can help support the show at patreon.com/truecrimeallthetimeVisit the show's website at truecrimeallthetime.com for contact, merchandise, and donation informationAn Emash Digital productionSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

everyone and welcome to the true crime all the time podcast. I'm Mike Ferguson. With me as always, but today only in spirit is Gibby. We're taking this week off. We announced that ahead of time, but we decided we wanted to have an episode out for everyone to listen to. So we're going back into the vault and putting out an episode that we did all the way back in 2022. And it's one of my favorite lesser-known true crime stories. And it's the story of Thomas Montgomery. I think I am fascinated by it so much because, you know, it involves catfishing, a love triangle,

people pretending to be someone they're not, that ultimately ends up in murder. So we hope everyone is enjoying their holidays, has a happy new year, and we'll be back with you next Sunday night with a brand new episode and the first episode of 2006. Enjoy. All right, buddy, are you ready to get into this episode of true crime all the time?

I'm ready. We are talking about a case that I've been wanting to do for a number of years. And it's a case centered around a man named Thomas Montgomery. Thomas Montgomery is currently incarcerated for murdering his 22-year-old coworker. Brian Barrett. The murder of Brian Barrett is a case that involves an extremely twisted web of lives and shows really how kind of normal everyday people can feel compelled to do disturbing things if they are dissatisfied with their lives. And the reason why this case has been on my radar for such a long time is that I watched a true crime doc on it many, many years ago. It's kind of one of the

the first true crime documentaries that I really remember seeing. And there's a love triangle, there's catfishing involved. This is just a story that's fascinated me for a very long time. In 2005, Thomas Montgomery began chatting with a young woman online. He told her he was an 18 year old Marine who would soon be sent to Iraq. But here's the problem, Gibbs. Thomas Montgomery was actually 46 years old, married, and had two teenage children. So he was lying out of the gate.

Yeah. And why am I expecting Chris Hanson to jump out from behind a curtain and, you know, ask this guy what the heck he's doing? Yeah, yeah. He lived in Cheek, Tawaga, New York. Now, Thomas was a former Marine. He obviously was not 18 years old. He never saw active combat during his time. in the military. He developed a struggle with alcohol abuse after he left the military,

but he stopped drinking when he became a husband and father. He had spent the past 12 years working as a machinist at a place called Dinabray, a factory in Clarence, New York. He wanted the career change, but knew starting over would mean a big decrease in pay. So he decided to stay there to support his family. And I think a lot of people go through that. I went through that myself in my 40s. You know, at a certain point, you think, man, I've been doing this job for a long time. I need something different. But that same kind of thing jumps out at you. Okay. If I go into a different career, I'm going to have to work my way up from the bottom again. I'm not going to just start out making what I'm making now. Yeah. Is it worth the risk? Is it worth the risk? Yeah.

For a lot of people, it's not. So in the mornings, Thomas clocked in, worked on components for power tools. After work, he walked his dog. He took his daughters to the local swimming club. Thomas enjoyed playing online poker and participating in the Dinah Bride, Yucer tournament. He and his wife, Cindy, had been married for 16 years. He had a loving family.

This guy taught Sunday school, and he was pretty well liked by his neighbors. He was even vice president of his daughter's swim club. Now it was said that some people at work thought Tom was awkward. But, you know, really other than that, there weren't complaints about this guy. So it seems to me gives, like, is though he had a pretty good thing going on. Yeah. Right? Did marriage kids?

Good job. People seem to like him. Other than the fact that he was chatting with a young girl online telling her he was 18 years old. But Tom's marriage was straightforward. struggling due to problems with impotence. I mentioned this documentary that I saw years and years ago. It's called Tall Hot Blonde. And it's really good. I don't know if it's streaming anywhere right now. I couldn't find it, actually. But Tom told the documentary team. I mean, I had a desire. But there was times I just couldn't do anything because it was like I put so much pressure on myself that maybe doing this,

we could get back together. But, sex in a relationship is only part of it. Communication is the other part. Tom spoke with the ministers at his church and they told him to practice communication with his wife. Tom admitted that he was never really able to see his wife Cindy's perspective on things. He said, I wasn't disappointed in her. I was more disappointed than how my life was. I mean, I had great kids. I had a great wife, but it seems like I felt guilty because I wasn't satisfied. I wanted something else. Basically saying that it wasn't enough. He needed something more. Yeah, but he's also saying it should have been enough. Yeah. Is what I'm getting from him. Great kids, great wife. It should have been

enough, but for some reason, it wasn't. So Thomas turned to the internet for entertainment. I mentioned he played cards online. He liked to play Texas hold them and poker on a gaming website called Pogo. He also liked to talk to people in chat rooms. Good old chat rooms. Are there still a thing? I don't know. I know they used to be pretty big back in the day.

Yeah, back in the day for sure. In 2010, Thomas Montgomery spoke with ABC 2020. He told them that he felt as though he was stuck in a dead-end job. that was slowly sucking the life out of me. You know, there's a lot of people that would describe their job like that. Yeah, I was sitting here thinking, man, I think a lot of people are probably going to identify with that statement. Yeah.

You know, unless you just happen to have a job that suits you to a T, at some point in time, you're bound to think, man, this job stinks. It's sucking the life out of me. You know, it is called a job. Yeah. He and his wife weren't as close as they once were. And he said he found solace in the internet. He said, I found it easier to talk to the people online than I could to my own wife.

I think the internet's a big escape for a lot of people. Yeah, I absolutely agree. I think where people can get in trouble is what type of escape are they using it as? You know, I've made no mistake. I escape to video games. I love video games. It's kind of what decompresses me. Now, if you're escaping your marriage by finding other people to talk to on the internet and starting up, you know, flirty conversations and stuff like that, well, you're heading down a path that could lead to disaster. Yeah, for sure.

Thomas's username online was Marine sniper. He chose his name as an homage to the six years he served in the military. But he also decided to invent an alternative version of himself. And he called this version Tommy. Tommy was an 18 year old Marine. He had bullet scars, red hair, was six foot two and 190 pounds. And right off the bat, this makes me think of a Brad Paisley song where he talks about, you know, a guy down in his mom's basement, reinventing himself on the internet. Have you ever heard that song? No. He says I'm six foot five. I live in Malibu. Oh, okay. I've got six pack abs. Yeah. When this guy's really like five foot two and no six pack abs. No six pack abs. But much like a job application or a resume, you got to, you got to pad it a little

bit. A little bit. You know, if you're five nine, magically you become six three. If you're 46, somehow magically you become 18 and fit. Yeah. When in reality you are not. If you're going to go on the internet and pretend, who's going to go on there and pretend to be themselves, the way that they currently are, especially given the fact that this guy wasn't happy with what he had going on.

So it does make sense to me. I'm not saying it's right, but it makes sense to me that he would, you know, kind of reinvent himself or invent kind of a different persona. He's not happy with his own. In May 2005, Thomas using the username Marine Sniper met an 18 year old girl in a Pogo chat room who used the username Tall Hot Blonde Big 50. So apparently he was playing Blackjack in a game room, tall hot blonde said hello to them

that began talking. she told Tom he was in the wrong room because it was a kid's room. He panicked and told her that he was 18. So apparently he decided to keep pretending, right? This is what he would later say, that he was the same age as this girl. He told ABC, I kept thinking, well, we're never going to meet. I'll just play the game with her. The two began chatting regularly.

And what really started off as flirting quickly turned, into an online relationship. Thomas learned that tall hot blonde was named Jessica or Jesse and that she was a senior in high school in West Virginia. All right. So he told ABC, he decided that he would just play the game with her. I think that's pretty euphemistic when you're talking about a 46 year old talking and starting an online relationship with a senior in high school.

Yeah, it's different than just saying I'm going to play some poker. Yes, you're not playing poker. You're playing, not even playing. You know, you're doing something that you shouldn't be doing. Now, Tall Hot Blonde sent Thomas photos of herself. Some of them were described as provocative. She also sent photos of her playing sports and later photos of her high school graduation. Now, she's sending photos.

It's only natural, right, that she's going to want to see what Tommy looked like. Yeah. So Thomas sent her a picture, a real picture of him from his time at Marine boot camp. But for some reason, I guess she didn't know that the picture was 30 years old. Maybe he doctored it up a little bit. I don't know. I was a little dubious of this because it's pretty easy, you would think, to tell the difference between a picture from 2010 and a picture from 1980. I think it probably would in most cases.

Now, if you did a little Photoshop and maybe made the background look a little more up to date or something like that, I'm sure it's possible. As time passed, Thomas became more invested in the relationship that he was having online than the relationships that he had in his personal life. And there's a real danger. And I think that happens to quite a few people. Jesse also seemed to return his feelings. They sent each other gifts. They talked on the phone. They wrote each other letters.

In one letter, Jesse told him, I love you always and forever, Tommy. Yeah, they're really building a relationship here. Yeah. We use the word relationship. And it is, but it's also kind of gross, too, if you, you know, and for sure, in my opinion, when you know the players. Yeah. when you know that he's 46 years old. Yes.

Tommy told Jesse that his mother died of cancer when he was just 12 and his father was a military veteran. Tommy said that when he was 17 years old, he raped a cheerleader. It's a really strange thing to say to someone that you're starting this relationship with. Yeah, I thought that was, it was weird to offer up that information. Now, he said, because of that, he felt hopeless. so enlisted in the military.

He had finished boot camp and would soon be deployed to Iraq. Jesse told Tommy that she was proud of him, even if he had made mistakes. Tommy said that she was the best thing that ever happened to him. So apparently Jesse took this news of rape fairly well. Because I don't believe that most people starting out in a relationship would take it that well. And now he's telling her that, um, you're the best thing ever happened to me. Even though he's been married, he's got kids, this online relationship is the best thing that's

ever happened to him. Now, is it really or is he playing the game, you know, kind of living the fantasy life and that's what you have to say. Because my whole thought, Gibbs, is that he's never going to meet this girl. He can't meet this girl in real life. No, because then she's going to see it's just been a big facade. So he's playing a part online. He's essentially catfishing this girl, right? Yeah. You'd have to say that.

Tom explained to the tall, hot, blonde producers why he made up the stories about Tommy the Marine. He said, I always wanted to be a combat Marine, always wanted to go to war. I don't know. Maybe I'm crazy or stupid or something, but I always wanted to test my skill against somebody else. And doing that with Jesse, let me live that life that I knew I was never going to live. So fantasy. Yeah, fantasy and lies, which sometimes are one and the same. Yeah. But what I always wonder is does this person who's pretending to be something they're not realize that there's somebody real on the other

side and that they're messing with them? I always wonder that. So he said that he's going to be to Iraq. He's got to weave that in. So what Thomas did is he began to pretend to be Tommy's father, Thomas Sr. after Tommy was supposedly deployed to Iraq. Right. Since Tommy had limited internet access, Tom Sr. sent messages between the two and asked Jesse to send him any mail she had for Tommy so that he could ship it to a wrap. They also continued speaking on the phone. Jesse and Tommy spoke on the phone from 630 to 640 a.m. And from 330 to 3.30 to 3.40 p.m.

Probably the time the real Tommy was driving to and from work. Actually, it could have been because no doubt, he's got to keep this under wraps. He can't let his wife find out. He can't have, you know, his kids walk in. him while he's playing pretend fantasy. Yeah. At one point, Tommy told Jesse that he was going to kill himself in Iraq. And she made him promise that he wouldn't do it.

One time Thomas and Jesse got into an online argument. He accused her of sending pictures to other people online. Jesse sent him an apology letter along with a pair of underwear and a key to my heart chain. So Tommy forgave Jesse, but apparently Tom Sr. did not. Okay. It's, it's kind of so bizarre. Right. Because they're both the same person. At one point, Jesse asked him why he wouldn't let it go. And Tom Senior responded, because you will hurt him and he's an idiot and will believe you're lying ass. It's like he's in a play, but he's the only actor. And he's playing all the parts. Exactly. in December 2005, Tommy proposed to Jesse. And Jesse responded by saying, yes, I will marry you, Tommy. Won't be long till it's Jessica Blair Montgomery.

So this is about seven months of online chatting. Right. They've never met in person and they're agreeing to marry each other. Let's get married. Let's get married. And maybe I'm old fashioned. Maybe I'm out of the loop. It could actually happen that way today.

I have no idea. haven't been on a date in like 28 years. I think it's happened, but I just think wouldn't you actually want to physically be in the same room with this person and make sure that, you know, they are who they are and they don't have some weird habit or annoying thing they do or, you know, I mean, you can hide behind the internet pretty well, right? Oh yeah. I mean, I want to go to blockbuster on Friday, pick out a movie. Oh, sorry, that was back when I used to actually date. Yeah, that, that's That's the old. They don't do it that way anymore.

No, no, no, no. Let's go see a movie, get dinner. We call it now Netflix and chill. But you're not even together. No. You're watching the same thing on Netflix talking over the phone. Yeah. So when Jesse actually accepted this proposal, reality kind of hit for Thomas Montgomery.

He told 2020, I was panicking. The lies kept getting more and more. Thomas, male, Jesse, point. that he is and she mailed him underwear and engraved dog tags that read Tom and Jesse always and forever. I'm not sure why this girl keeps sending underwear in the mail. But again, not been on the date in 28 years. She's just sending underwear left and right. She is. So apparently Jesse had planned their life together. How it was going to go once they got married, once he returned from Iraq. Thomas decided that things had gone too far. And the best thing to do would be to quote,

unquote, kill Tommy. Okay. Tommy's not real, but we got to kill him all. Right. Thomas wanted to say that he died in a routine patrol, but he couldn't go through with it because of how serious the relationship was. By this point, Gibbs, he and Jesse were having virtual sex. Okay. So online sex couldn't, uh, couldn't end the relationship. Didn't feel right about it. No, but he felt okay having virtual sex with a high school senior. Yeah. At 46 years old.

He had zero problems with that. Or did he have problems with it, but he just didn't want to let it go. Yeah. You know, interestingly, he told 2020 that this sex was happening between Jesse and Tommy, right? like when he was talking to the 2020 show, he wouldn't actually say that he was involved. Is it how he justified it. Maybe in his mind because these are two 18-year-olds or however old,

Tommy's 18. These are two young kids, young adults. He's a 46-year-old, middle-aged pervert with kids and a wife. Now, he did say that the sex made him feel dirt. but he felt that he was in too deep to end the relationship. He said, if I was smart, I would have just ended it, but it was like a drug that I needed every day. So it didn't make him feel that dirty.

No, but he has to say that. Sure. Or maybe it did, but he still couldn't end it. Because I think it could be both. Yeah, I feel dirty about it, but I like it too much and I'm not going to end it. Yeah, I was addicted to it. In real life, Thomas Monk. Montgomery was constantly talking about Jesse at work. I mean, he gives he was telling people he was going to leave his wife. He was going to move in with her. I mean, if he's saying this at work, is he really just playing a game? Yeah. I mean, that's really where you're outside of the fantasy mode at that point, right? If you're talking about this to coworkers, you're making it real. Yeah. He started making plans for the new year. He hit a piece of paper at work that said,

On January 2nd, 2006, Tom Montgomery, 46 years old, ceases to exist and is replaced by an 18-year-old battle-scarred Marine. He's moving to West Virginia to be with the love of his life. Was this like one of those motivational things you read every day or? Or like the start of a checklist or yeah, something. He was writing his feelings, right? He was frustrated because he knew. he could never really turn into Tommy. And he wrote, I wish I would know the exact time I would change to new Tom to prepare for it.

Just like this relationship, it's unreal. Yeah, I think this guy's spiraling out of control. I mean, I wasn't happy with it from the very beginning. Because you know, if I even had an inkling that some 46-year-old man was talking to my high school senior daughter, which I have one who's a senior right now, it would hit the fan. Yeah. Because I think it's disgusting. It is.

You got to wonder what his wife was doing. Or what she was thinking. Yeah. I think what was apparent from the research was that she didn't know exactly what was going on. She didn't know what he was doing, but she knew something was up. She could tell that he wasn't himself. He wasn't acting the same. And I think that's true for a lot of partners.

When their partner is cheating, a lot of times they can tell. Maybe not exactly what they're doing, but something is different. They're just not engaged in a relationship like they used to be, right? Yeah, or they're losing weight. They're buying new clothes. You know, that could just be, hey, I want to get in shape. Or it could be, I want to look good for somebody new. Yeah.

You've heard, you know, I've heard that. from time to time from people. Yeah, or, you know, their cell phone or... They hide their cell phone. Hide their cell phones. Wipe it, lock it. I mean, there's all kinds of different things you can, you can think of. The truth came out in March 2006.

One of Thomas's daughters was using the computer when Jesse sent a message. And the daughter told Cindy, who eventually found the letters, the photos, and the gifts from Jesse. I can't imagine this guy's daughter is seeing this message come across. Oh, and then Cindy finds out about it and she goes a hunt and then there's the letters. There's the underwear that we mentioned. I'm assuming he kept it in a box or whatever he kept it in. That's going to be a rough day when you open that up and find all of this stuff.

Yeah. Obviously, Cindy was upset. She was disgusted. She wrote in a note to Tom. What I cannot believe is that you are living out some bizarre fantasy as father and son. If you want to separate, we can. But to continue to lie to me and the kids while she is sending your son, in quotes, gifts in the mail is not acceptable.

Well, she's exactly right. Yes, she's exactly right. She actually, you know, toned it down a little bit from what I would have expected her to say. but Tom and Cindy continued living together. Tom moved into the basement though. Cindy felt like she had to tell Jesse the truth. So what she did was she mailed a family photo and a letter. And the following that I'm going to read is an excerpt from the letter. Jess, in closed, you will find a picture of my family. Let me introduce you to these people. The man in the center is Tom, my husband. There is no Tommy. He is taking. He is taking. He is taking. advantage of you, you need to be much more cautious with your safety. You will only be hurt by a man who has mastered the art of manipulation and lies. Do not trust words on a computer. So now you have to think of Jesse getting this letter, this photo, finding out that Tom is not the 18 year old Tommy. In fact, a 46 year old guy, a husband, father of a,

to she's got to be horrified but i'm not sure she was a hundred percent sure who to believe tommy or this woman who's sending me you know this photo so in april of 2006 she decided to message beefcake 1572 beefcake yeah which as i know is very close to what you used to go by in your online persona but this beefcake was Tommy's friend who also used Pogo and Beefcake confirmed that Tom was lying to her. Beefcake was 22-year-old Brian Barrett. Brian was a part-time employee at Dinabraid and a student at Buffalo State College. He was working at the factory to help pay for college. He wanted to teach industrial arts. Brian was a talented high school athlete and he coached Little League in soccer. He was said to have been a very

quiet and honest person. Sounds like he was a good guy all the way around. Yeah. Yeah, it really does. So Brian began chatting with Jesse. He tried to make her feel better about the whole situation. But unlike Tom, Brian never lied about his age or his career. And Jesse ultimately began an online relationship with Brian.

That 18 to 22 is a much smaller gap in age. Yeah, it's not one that's going to, you know, want to make you throw up in your mouth. Right. Like the other one. But I mentioned it, right? Brian and Thomas were co-workers. And Brian didn't keep this relationship with Jesse secret from Thomas Montgomery. And neither did Jesse. Jesse managed Tom. She said, he's honest. He wasn't a liar like you were. He's closer to my age. And so what happened was Tom and Brian developed a rivalry over Jesse so much so that their co-workers at Dinabrade began to notice the tension between these two guys. So you got a 46-year-old married guy with kids, jealous over a 22-year-old guy,

trying to have a relationship with an 18-year-old girl that the 46-year-old wants to have. Yeah. Jesse sent Brian the same photos that she sent Thomas. She also sent him cards and letters saying she loved him. And Thomas just got to the point where he was overcome with jealousy. And at one point, he messaged Jesse saying, Brian will pay in blood. He's thinking this really serious and hard. But this is the same guy that was thinking of a way to get out of this earlier, you know. Oh, he thought about it for a minute, I think. He told ABC or 2020 or whatever it was. Right.

This is what I thought about doing. This is what I should have done. done, but I didn't. Yeah, because the sex was too good. The, the idea of having whatever you want to call it a relationship with this young girl was just too enticing to him because he was a scumbag. And I don't feel bad saying that because I do think that is such a scummy thing to do. And while technically, you know, it's not illegal. Right. They're both adults. I still think it's scummy. I don't like it. I mean, she's still old at school. I don't care.

The age is just too, it's too much for me. But now this is pretty ominous, right? This is threatening. Brian will pay him blood. As more time passed, Thomas's anger only increased. He sent threatening and nasty messages to Jesse.

One message said, you are nothing and will be nothing but a lying whore. You said he's taking it hard. and I'd have to back that statement up. He's also, you know, being very nasty. Yeah. Jesse and Brian decided to spread the word throughout the chat rooms that Marine sniper was actually, by this time, a 47-year-old man.

They accused Tom of being a predator. And this really sent Thomas over the top, made him furious. He told Jesse that half the company thought he was a predator and parents didn't trust him anymore. He messaged Jesse, you can say goodbye forever to me and Tommy, which I think she thought, many people have thought to mean that he was considering ending his life. You know, he didn't like that they put that out there, but it's the truth. He knew what he was doing. He knew it wasn't right. Yeah, age difference aside, because I know a lot of people will probably get on me saying, well, what's wrong with it? It's legal. They're both. You're both. You're

of age, but he wasn't being himself. Right. He wasn't being truth. Right. He was saying he was 18. I mean, that's to me is the, the, even the more scummy part of the whole thing. But the other thing that kind of jumps out at me is imagine getting so worked up over somebody who you've never met in person.

Yeah. You tricked into believing that you were 18. And then once she found out that you weren't, she moved on. And you got up. said over it because she found out that you were lying about your age. Right. Now, though, she and Brian are telling people at work and you can argue whether or not that's a smart thing to do, most people would not be happy. No. About that. Now, you could say he had it coming, but he's not going to be happy about it and he wasn't. At one point, Tom threatened to go to West Virginia

and hurt Jesse if she didn't leave him alone. The guy's got a lot of threats. too. Yeah. Jesse stopped messaging him, but then she told Tom that her mother wanted to speak to him. Jesse's mother asked Tom to leave her daughter alone, and Tom said he would if Jesse left him alone. So again, Jesse stopped messaging Tom for a while, but then she initiated contact again. Jesse told Thomas, if Tommy existed, I would still be holding him every night and sharing

dreams with him every night. I ate to be with Tommy. This is one of the weirdest stories we've ever done. It really is. And I'm telling you right now, it's only going to get more strange. You know, as we go along, this is a girl who's being threatened

by a now 47-year-old man. Yeah. But she's initiating contact and saying, oh, if Tommy only existed. Yeah. If he was only the person he said he was. Then we could be to,

We'd be together right now. And Tom would respond with messages like, I wish I could be that 19 year old Marine for you. Thomas claimed he tried to end the relationship, but Jesse talked him into staying. So there are some more messages between the two. I want to read some of them because I think they provide a little bit of insight, you know,

as to what was going on between these two individuals. Marine sniper said, I have to leave honey. Jesse said, why, Tom? Because I can never have you as I want you. Don't go. Why, Jesse, you can get on with your life then. I have no life.

He said, honey, yes, you do. My grades are dropping. I hate softball. I fight with my ma all the time. So there's nothing really bombshelly in there, but you can just kind of get a sense of this is probably happening every day. Right. These messages going back and forth.

Jesse promised Tom she would stop talking to Brian. But she didn't. She continued their relationship and she tried to hide from Thomas. But Brian encouraged her to post about him and her profile and that he would do the same. So in late summer 2006, Thomas found out Jesse was talking to Brian again. So he messaged Brian. I can't believe you chose her over our friendship. You wanted her.

You got her. just tell her to leave me alone. I'm also somewhat flabbergasted that this 47-year-old man is duking it out with this 22, who probably now 23-year-old young man. Right. Over somebody, neither one of them have met up in person. Yeah. The idea of this girl, Thomas began acting strangely.

He told Jesse he was, quote, training for war. He started exercising. running five miles a day, he was making threats to people at work, which I think as always happens, starts to make your coworkers nervous. Tom was spending so much time on the computer that he was barely sleeping. And his messages to Jesse became extremely disturbing. They ranged from sexual messages to declarations of love to threats. He threatened to post her address online so that people could

go find her. This guy is losing it. I mean, you can literally see him spiraling. Yeah. Out of control. Again, over a girl that he has never met. I have to keep saying that. Brian was set to visit Jesse for the holiday, but she told him not to. She told Thomas that she wanted to be with him and that she would break up with Brian. Thomas agreed if she never lied to him again. But then Jesse broke up with Thomas again and started up her relationship with Brian. This is so bizarre. It's bizarre. But you know what it's making me think of?

Like the 10th grade. Yeah. You know, we date for a week. I break up with you. I start dating your friend. I break up with him. I go back to dating you. But these are adults.

One of them is 47 years old. Yeah. And at this point, Jesse's in the middle of it now. stirring the pot too. Oh yeah. Yeah, I think that's safe to say. Just as we talked about Thomas, you know, saying that he should have walked away. He could have walked away, but he didn't. You could say the exact same thing about Jesse. She could have just stopped talking to him. Yeah. But it's like she just kept rekindling, starting things back up and messing with him.

And at the same time, messing with Brian. But when she broke up with Thomas, again and started dating Brian, Thomas was devastated. He was already jealous. Now he was extremely jealous. But what seemed to be the final straw was when Brian decided to visit Jesse. Brian was taking a trip to North Carolina and he wanted to stop in West Virginia on his way home. At the last minute, Jesse asked Brian not to meet her. But Thomas already knew about this supposed meeting and he was furious. After trying to get Tom to forgive her for a few days, Jesse stopped messaging him. Tom messaged Jesse on September 13, 2006 at 133 a.m. saying, you are a. And that's all you will ever be. Jesse responded by saying, I'm leaving now. And Jesse didn't respond

to his subsequent messages. He called her on the morning of September 15th and screamed her and Jesse hung up on him. And Brian Barrett was murdered later that day. So at 10, 16 p.m., Brian clocked out of work. He was shot as soon as he entered his truck. In the late hours of the 15th, Tom messaged Jesse, you waiting for your boyfriend. At 2.15 a.m. on the 16th, he messaged her, come on, your boyfriend Brian won't mind you talking to me. Brian's body wasn't found until the morning of September 17th. When a coworker saw his truck in the parking lot, he had been shot in the neck and left arm at close range.

He was hit by 30 caliber bullets in what was called a sniper style shooting. People heard gunshots and several witnesses saw someone in the area. The Erie County Sheriff's Office believed Brian was shot by a man wearing a ski mask and camo. So we have Thomas Montgomery who always wanted to be a Marine sniper. He's working out, Gibbs. He's exercising. Right.

He's planning something. And police quickly learned about the link between Thomas Montgomery and Brian Barrett. They found threats from Thomas to Brian and Jesse. But police couldn't find Thomas right away. And they worried that he was going to. to West Virginia to find Jesse and hurt her. Detectives found Jesse's number on Brian's phone. A New York officer spoke to Jesse on the phone and sent word to the police department in

West Virginia to send an officer to Jesse's address. The police made it their main priority to locate Jesse and make sure that she was safe. All right. It's a good thing. You've got a credible threat to this girl's life. Sure. You want to protect her. an officer got her address and went to the house the next day.

A middle-aged woman named Mary Shiler answered the door. She said she was Jessie's mother and said that Jesse wasn't home. The officer called Lieutenant Ron Kenyon, who had spoken with Jesse on the phone to confirm she had a relationship with Thomas and Brian and warned her that she was in danger. The officer in West Virginia questioned Mary Shiler, and she was acting very nervous. eventually, Mary confessed that she was pretending to be her daughter online. Gibbs, she was the person behind the tall, hot, blonde username. This is the catfish of all catfishes.

Yeah. The catfishing all around except for the victim, Brian. Right. This is double catfish and Brian is the one that paid the price. And he was the only one who was acting as the person who he really was. He's the only one being truthful. Mary told the police that she had been using Jesse's pictures without her knowledge. Police found hundreds of pictures of Jesse on Mary's computer.

Many of the pictures looked as though they had been taken without Jesse even knowing. Mary was also sending pictures of Jesse to several men. It wasn't just Thomas and Brian. So really not the mother of the year, is she? No. And so as harsh as I was, on Thomas Montgomery, I'm just as disgusted by this Mary woman. Okay, you want to pretend to be somebody you're not online?

Okay. I guess if that's what you want to do, but you're going to use pictures of your real daughter. Unless she doesn't even know you've taken the pictures. And are you sending her underwear to men in the mail? What are you thinking? And what does Jesse think of her mom? And when all this comes out, I guess we'll have to, we'll have to talk about that a little bit. And at the end of the day, what do you think what's going to happen when you eventually had to actually meet?

Well, here's my thought. My thought is when people start this type of stuff, they just never think it's going to get as out of control as it ultimately can. It's never going to get to the point where they're actually going to have to meet somebody or, you know, something like. that. But things can spiral out of control very quickly, and obviously they did in this case. The police searched Brian and Mary's computers and gathered hundreds of pages of messages. They wondered why Thomas would kill Brian if he wasn't ever going to have a real relationship with Jesse. So New York detectives were still trying to tie Thomas to Brian's murder. Co-workers spoke with the police and said that

Tom had been speaking badly about Brian. He had been acting very strangely. Tom told one coworker, he wouldn't be stupid enough to leave shell casings behind if he killed someone. He had also asked his co-workers what time Brian got off work. So his comments at work, I said, it made his coworkers anxious, nervous. Sure. And they told police. They thought he was capable of violence. Tom had also been bragging about his online relationship since the beginning, since it started in 2005. Well, that's true. He had no problem talking about this at his work. Eventually, Tom was located and questioned about the murder. He told the police that he couldn't talk until he got his lunch from his car because his peaches would go back. You know what?

Police don't give a you know what about? Yeah, your peaches. Your peaches. Tom said he went to a restaurant and he got home between 10 and 10. 10 p.m. on September 15th. But Tom's wife said he got home about a half hour later than that. And Tom's phone record showed that he was near Dinabrade when Brian was killed. You know who you should not expect to back up your alibi? Your wife that you're cheating on. Yeah. Who's not happy with you in the slightest?

Right. Thomas Montgomery was arrested at home on November 27, 2006, and charged with second degree murder, he pleaded not guilty and was held without bail. It took the police two months to make an arrest because it took a long time to interview Mary, to look through all the computers, to put all this evidence together. But eventually, they did put a lot of evidence together against Thomas. The one problem they had was that they couldn't find the murder weapon. So I mentioned this very strange comment. that Tom had made about the peaches and his lunch were going to go bad.

Police found a peach pit next to Brian's truck and they tested it for Tom's DNA. A leather case with dog hair on it was found in the same area. Tom had a dog. Jesse's underwear was eventually found in Tom's house. The police also found a picture of Tom's gun cabinet showing a 30 caliber rifle. But when they searched the house, it was missing. after Tom was arrested. He stopped eating. He lost a significant amount of weight. He found sleeping pills in someone's cell and he took 25 pills in an apparent attempt to end his life.

Tom's attorney looked into an insanity defense, but the psychiatrist told him there wasn't enough evidence to support a claim of insanity. John DeFrank's Erie County Deputy DA told the New York times in January 2007. The uniqueness of this case is that everybody appeared to be misleading everybody else and the whole situation which resulted in a violent death

was unnecessary. Like we said, Gives, this guy told the paper, ironically, the only person telling the truth here was the victim. Yeah. Prosecutors wanted to charge Mary Shiler with anything that they could, but they ultimately

came to the conclusion that although what she did was morally wrong, she didn't actually break any laws. Prosecutor Ken Case told ABC 2020, shame on her. She not only didn't do anything about it, I think she provoked it. Unfortunately, in New York State, you have to do a little something more to be criminally liable. Yeah, I mean, it's a shame because she does have some responsibility in this. She does. But. how could she have known that this guy was going to kill Brian? Well, that's true. She didn't.

Now, if she would have said, hey, if you get rid of Brian, we'll be together. Yeah. Or anything along those lines, then obviously they could have, you know, charged her with something. Tom claimed he had an alibi and that his wife and kids would back him up. But like we've already said, right, Cindy told the police that, no, Tom was not at home when the shooting occurred. Tom spoke on the phone with his daughters and told them that if they didn't testify,

he would lose his trial. But Tom wanted to protect his daughters from the trial. So he began talking with his attorney about making a plea deal, probably pretty smart. Oh. Once you find out that your wife's not going to back you up, no guarantee that your daughters are going to get on the stand and back you up. They can't be real happy with you. No.

You've ruined their life. Yeah, you ruin the whole family. So on August 20th, 2007, Thomas Montgomery pleaded guilty to first degree manslaughter, a reduced charge. Thomas admitted that he shot Brian three times with his 30 caliber rifle. When the judge asked if he intended to kill Brian, Thomas said no until his defense attorney nudged him. And then Thomas admitted that he did intended. He also admitted to planning.

the murder. I don't know who Thomas was trying to fool. I mean, he shot Brian three times. Of course he was attempting to kill him. I don't know what other argument you could make. One shot, maybe say I was showing him the gun and it accidentally went off. It's not going to accidentally go off three times. And why would you have a gun at the workplace at all? But you know, Gibbs as many cases as we've done. People try to say stuff that doesn't make. You know, gives as many cases as we've done. people try to say stuff that doesn't make any sense, but they're grasping at straws. And then it's almost as if the light bulb goes off at some point and they realize what I'm saying makes no sense. I'm not getting out of this. So I might as well, you know,

fess up, tell the truth. But I did think it was kind of funny that at first he said no, but then his defense attorney nudged him and said, no, no, you got to say. You got to say you, you, uh, you did it because it's part of the plea deal. Brian's parents agreed to the plea deal once they learned that Thomas would be in jail for at least 20 years, which apparently was a longer sentence than he might have received if he was convicted of second-degree murder. On November 27, 2007, Thomas Montgomery was sentenced to 20 years in prison with five years of supervision.

He attempted to withdraw his guilty plea, but the judge denied. his motion. And we see that in so many cases. People, you know, entering a guilty plea, making a plea deal, and then later trying to get out of it. I don't know what he thought he would be getting out. I don't know what better deal he thought he was going to get to this. Go to trial. Yeah, they had a ton of evidence against him. If you think about the computer evidence alone, the messages, the cell phone putting him at dinabra. at the time of the murder, no way is he getting acquitted.

It just wasn't going to happen. Now, maybe he found out that he could actually get convicted of second degree murder and end up with a lighter sentence than 20 years. And he wanted to try that route. But then you're taking a big chance, right? Huge risk. That you get first degree and maybe end up spending the rest of your life in prison. Tom argued that he was put in special observation because of mental health.

health concerns, once he was able to use a pen and paper again, he wrote a petition to file for new counsel and said he had an automatic right to new counsel. His new attorney said that Tom's motion to take back his plea proved that he didn't understand the basic elements of a plea deal. Tom's first attorney was removed from the case in October of 2007. According to John Neutcher Reno, his second attorney, Tom said that his first attorney, John Malloy, told him that he could take the plea deal off the table at any time. According to the union son and journal, Brian's father, Dan Barrett, said at the sentencing hearing, my wife and I don't understand how this could happen to our family. We don't understand how such evil could exist in the world.

To gun down a boy over simple jealousy does not make sense. sense. We were hoping for more. But to be honest with you, we were prepared to take the 20 if we had to, which obviously we did. We were glad to see that the judge didn't prolong this any longer and give Montgomery more rights than my son ever got. You talk about some grieving parents. Right. And in the wake of that, or while still grieving, having to make a decision in conjunction with the prosecution maybe, are you willing to go along with this plea deal? It's tough stuff. It is. And obviously you can tell from his comments, they weren't thrilled with it, but a guaranteed 20 versus maybe a shorter sentence on second degree, I think you have to make

that decision. Yeah, I agree with you. I think you have to take that and say, at least we've got him locked in for a while. We know where he's going to be for the next 20 years. Yeah. Brian's family filed a wrongful death lawsuit against Thomas, Dina Braide, and Mary Shiler. Thomas's attorney announced his intentions to appeal the sentence and said that Thomas had been receiving treatment for depression before his arrest and his internet relationship didn't help this depression. The prosecutor responded by saying he's a stone cold calculating killer who put three bullets in an unarmed kid. and let his body sit in his truck until it was discovered by a stranger. I think that sums it up pretty well. I think so too.

To be honest with you, I didn't understand Thomas's attorneys talk about his depression and okay, we all suffer from depression. Right. From time to time. It's a pretty common thing. I get it. This internet relationship, and I'm using that in quotes, didn't help the depression. What's that got to do with the fact that your client murdered a young man?

This was just pure jealousy. Yeah. He knew what he was doing. He knew right from wrong. This is nothing like our Patreon episode where the killer had quite a long history of documented mental illness. I'm viewing these as very, very different. In 2007, Thomas told the Guardian that he wasn't the killer. He claimed Brian was getting calls from people who disliked him.

He also mentioned that he was happy when Jesse and Brian started their relationship because Brian was more appropriate for her age. Yeah, okay. This guy is talking out of his ass. Absolutely, yes. You know, his wife, if you remember, called him a master manipulator. Yeah. I think he was.

I think he's still trying to work it. And I think he's working it, you know, through the guard. Mary's husband Tim divorced her, not a shocker. No. And the real Jesse cut off all contact with her mother. Not a surprise. Not a shocker either. Tim Shiler told the tall, hot blonde producers that he feels Mary is responsible for Brian's death.

He didn't learn the full truth until Mary had to go to New York to testify before a grand jury. He didn't know that she was using Jesse's photos until Jesse told him. Jesse found out what happened when she Googled her mother's name after her friends made some comments to her. Probably made both Tim and Jesse sick to her stomach. Yeah, I think they were devastated because he told outlets. He had his whole life planned out with Mary. He thought they had a loving marriage. Obviously, he was wrong.

And I still go back to how devastated Jesse must have been, must still be, to find out that her mother did this using her pictures as bait to mess with guys on the internet. And some of the pictures Jesse didn't even know we're taking of her. And we mentioned that some were called provocative. Yeah. So I don't know exactly how bad they were, but taking pictures of someone while they're not looking, they might be in a position that is provocative.

They wouldn't want to have their picture taken if they knew that someone was taking it. I could see how that could happen. I don't get it. It's sickening, but I can see how Mary being so close to her daughter could have snapped pictures when she wasn't looking. Mary told Guardian journalist Nadia Lobby that she joined Pogo to relax and kill time. She said that she realized she accidentally used Jesse's screen name. She was sent to a teen chat room and never made an effort to correct the mistake.

She said she didn't mean to make anyone fall in love with her. She was happy with her marriage. And she didn't know how to stop Brian from flirting. Well, maybe not send him pictures of your daughter. Yeah, I think that would be one way. She called Tom a child who needed someone to show him they cared. She said she didn't stop talking to Tommy because she worried if she stopped messaging him, he would really take advantage of an 18 year old.

This is as much BS as Thomas Montgomery. And I mentioned Chris Hansen earlier. This really reminds me, you know, if you think back to those old to catch a predator. the things that some of those guys said when Chris Hansen revealed himself, it was like none of it made sense. None of this makes sense. It's just all an effort to try to make yourself not look so bad. But you can't do it because what you did was so horrible. And you said, don't send pictures.

How about don't mail underwear? Yeah, that too. if you're not trying to get someone to fall for you. Mary granted one formal interview to BBC and said, it was stupid. It should have never happened. I just never thought it would go anywhere, that it would end,

fall off, and that would be the end of it. And that actually makes sense. I could see where that was the thought in the beginning. But as it progressed, and as we laid it out, at some point, Mary kept provoking things.

Well, she crossed the line, like you said, sending pictures of her daughter. Yes. Sending underwear, probably her daughters, having virtual sex, pretending to be her daughter. All of that horrible. Yeah. But at any point in time, at many points in time, as we laid it out, she could have stopped replying. Yeah.

Sometimes when things had ended, she. initiated the contact. Yeah, he actually tried to end it a few times, supposedly. So, yeah, according to him. Yeah. So she could have just deleted him. She could delete her whole profile that she said wasn't even right to use anyway, right? She started using her daughter's profile and realized it and but continued on. Why not just delete it? Or just don't message the guy anymore. Yeah. But it's like she couldn't help herself. She had to start things. back up. She enjoy the intention as much as he enjoyed the attention. I believe, I believe that's true. Cindy divorced Thomas Montgomery. His daughters have chosen not to speak to news outlets about the case.

Some of the people most affected by this whole situation were Brian's parents. Dan and Deb Barrett, Deb told the tall, hot blonde producers, even people at Dinabray, if they would have just stepped up to the plate and said, There's a problem here at work that we feel you should be aware of. Then we would have been able to have the opportunity to talk to him. As I said, Brian never complained about anything. So he never said, geez, this guy's giving me a hard time. Thomas Montgomery is currently housed in the Wyoming facility in New York State. So Montgomery has a parole interview next year, 2003.

His earliest possible release date. is January of 2024. That's not that far away. No. And even if he gets denied, he'll be released in November, 2026 at the latest. So I believe he's 63 years old right now. Yeah.

So he'll get out at the very latest he'll be 67 years old. Yeah. But like I said in the beginning, Gibbs, this is a case that I've been wanting to do for a long time. There were so many, you know, interesting aspects, not one catfish, but two catfishes going opposite way.

Yeah. And we can't forget about this young man, Brian Barrett, who got caught up in it and became the victim of a murder. Yeah, she pulled him into it. Yeah, she did. She did. And then I believe she stoked the flames. Yeah. Now, ultimately, Thomas Montgomery made the decision.

sure to take this man's life and I think he's a horrible human being but I'm I'm not real big on this merry woman I don't know how she sleeps in night no she may not have been able to be held criminally responsible but in my book she falls into the POS category I'm just going to say it yeah for sure and I feel horrible for what happened to Brian and I feel horrible for his parents yeah But this is a case and a really unfortunate example of just how easy it is to lie to people when someone is hiding behind a username and, you know, carefully selecting a profile picture. I think it should also serve as a reminder and a cautionary tale to everyone that children and even adults need to be extremely careful when dealing with strangers online. Yeah. You never know just exactly who you're chatting with. This is Stranger Danger at a higher level. At a different level, right? Yeah. It's not getting into people's cars, but it's being taken for a ride by maybe a master manipulator.

Yeah. Sitting behind a keyboard telling you all the things you want to hear. Grooming you. And potentially grooming you. Yeah. But that's it for our case on Thomas Montgomery. We've got some voicemails, Gibbs. You want to check those out? Let's hear them. Hi, this is Callum. It's trust me from Pennsylvania. I would love to hear you guys do the story of Pamela Hup.

What a twisted, twisted tale. This woman killed so many people and tried to make it look like she didn't do anything, all to get insurance money. I love you guys. Keep your own sense. thicken. The good old insurance money scam. Yeah, that that is a fascinating case. You know, the problem that you and I always have is we don't really like to do cases after they've come out with some big documentary or in this case, it was the series with Renee Zellweger. So I kind of

push things down the list after they, they come out. But we'll definitely do that case because it is fascinating. It really is. Hi, my name is Chantal. My name is Shantelle. And I'm a from Australia. I just wanted to call and just say that I really enjoy listening to your podcast. My mum actually first introduced me to the podcast by Sawyer. She started listening without her. She's not very happy about that because every time when she wants to listen to it with me, I'm like, oh, thank you to listen to that episode. Well, I just want to say again, I really enjoy listening to your podcast. I listen to it everywhere as much as I possibly can. My friends see me listening to that.

something they know I'm listening to crime, which I'm not sure if that's good, but yeah, it also makes me quite aware, I guess, because as a teenager, like, trying to explore the world. You have to be aware of, like, there's dangerous people and all that does. We won't

get much into that. I actually have a suggestion for you guys. Eisen Millat, he was a famous Australian zero killer. He used to kill hitchhackers and backpackers in the late 80s to early 90s. My dad actually knew one of his victims, so that's sort of a connection there.

Well, anyways, for now, keep your own time ticking. Oh, that was awesome. So I would say this. Be nice to your mom. Re-listen to them with your mom. Yes. Do that. You got to do that. And Ivan Malat is a big timer. He is. And he's definitely on the list. I'm not sure when we'll tackle that case, but it's a biggie for sure. Here's a little fun fact for you guys. Did you know that Daniel Rowling, the Gainesville Ripper, did all of his mutilations and killings and decapitation that takes K Bar and ice? Well, now you know, stay safe and keep your own time ticking. See you.

I don't know, Gibbs. It's been so long since we did Danny Rowling. I don't know that we talked about K Bar at all. Maybe we did, but that's been years. It has been. That's got to be probably at least five years since we've done that case. Yeah. Interesting fact, though.

Yeah, it is. It is. At first, I thought he said Kmart. Kmart. Which could have been possible as well. We'd never know. We'd never know. But he could have gotten to Kmart.

Yeah. Could have bought the K bar at Kmart? Can you, well, you can't buy a K bar now because there are no Kmart's, at least around us. No. They're all out of business. Yeah, they're gone. All right.

But we appreciate the voicemail. No mail bag this week. So that's it for another. episode of true crime all the time. So for Mike, and get me. Stay safe and keep your own time ticking.