Reckless

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0:45If you wait until something breaks, you're already behind. Count on Grainger for quality products, easy reordering, and 24-7 support. Call 1-800-GRAINGER, click grainger.com, or just stop by. Grainger. For the ones who get it done. I believe that he had an old soul, a beautiful soul. I know he's my son, but he was the kindest person I've ever met in my life. He was definitely God's gift to me. A dramatic development in the case of a beloved teenage boy who disappeared. I have to report my son missing. They saw his truck with caution tape around it. The police told my father that he was gone. He said, are you sure?

1:28Like, what are you talking about? Grieving alongside his family, his girlfriend. She sent messages of condolences. We all need to be strong together. She gave me a lot of support. Just there for me when I needed her. But was there something about these two that no one knew? What are you seeing? A series of messages. I had to read them a couple of times to really sort of take it all in. Utterly shocking. A trail of text messages leading to the darkest of discoveries. Keeping all the lies straight is difficult. She did it masterfully. That's not normal. I closed my eyes and I said, this is not real.

2:03Now, a new twist in a story every parent needs to see. We need to know what's going on in our kids' lives, because it can be very scary when we don't. The latest on a story of teens, text messages, and a complicated search for the truth. I'm Lester Holt, and this is Dateline. Here's Andrea Canning with Reckless.

2:32It began as a chance encounter between two teens on vacation. She was a family friend that he met in Florida. And ended two years later with one of them dead. He was smiling before he left the house. And then he was dead a few hours after. An apparent suicide. He didn't seem like he was in any imminent danger. No, not at all. But there was danger from something teens do all the time. Texting. Their cyber romance hit a nerve, gripping the nation. And the people involved in the case gave us the inside story. The detectives who investigated the case. You're watching her. Yes. And it just keeps getting worse.

3:13A grieving father. I feel like I can fix a lot of things, but I just couldn't fix my son. And distraught family members who feel betrayed. I like kind of just said no. Hi, this is Conrad Henry Roy III. Our story starts with Conrad. His mother, Linroy, says he was an easy child. What kind of kid was he? Definitely sensitive. Never gave me a hard time with anything. Did well in school, had friends, loved baseball. Conrad was her firstborn. Two daughters would come later. Looking back, she remembers his early years as good ones. Every picture I have of him, he looks like a little goofball. The happiest child.

3:54He was always happy. Conrad grew up in and around the old fishing town of New Bedford, Massachusetts, where his father and grandfather run a tugboat and barge business. His dad said it seemed Conrad was destined to take to the sea from day one. I think I was like two or three days old and my dad brought him on the tugboat. I just wanted to have him to follow in my footsteps. I was hoping he'd be able to just take over the business someday. Not only was Conrad the first born in the Roy family, he was also the first grandchild. His aunt, Chrissy Roy, says his cousins adored him. My youngest, Henry, would follow him around like a duck.

4:35He was the cousin that all of the kids looked up to. But during his sophomore year in high school, his mom says her happy-go-lucky son started to change. His father and I, we got divorced, and I don't know one child that doesn't get affected by a divorce. He was 16 at the time? And it's, you know, going through the hormones, and he obviously had anxiety and depression. It just manifested at that time. He talked about it in this video diary. I feel like I'm differently wired from everyone else. Like there's something wrong with me. It was at 16, while struggling with anxiety and depression, that Conrad encountered a 15-year-old girl named Michelle Carter.

5:18They met, Conrad's grandmother says, when Conrad and his sisters went to Florida to visit family. And this was just supposed to be some R &R? Yep. A week during school vacation. Her grandparents were friends with our great aunt. And his sister Camden was like, oh, my brother met a girl. And the three of them all hung out with her for just a short while. When they returned from Florida, Conrad and Michelle continued to stay in touch through text messages. Michelle lived in Plainville, Massachusetts, about an hour away from Conrad. The two had a lot in common. She was a softball player. He played baseball.

5:54Friends describe both of them as quiet and funny. And even though the two communicated regularly, Conrad's Aunt Becky says he never mentioned Michelle. He had other girlfriends where you knew their names and you had met them. She was not someone that he talked about. Apparently, he kept a lot to himself. By the time he was 17, he had checked into psychiatric facilities a few times, suffering from deep depression. His mom says one time, on the day he was discharged, he attempted suicide by swallowing a bottle of cough syrup. He felt bad. That's a good one, right? You have no idea how much you were loved and appreciated.

6:39But he swore at that time after that, he would never attempt suicide again. And things did seem to be getting better. A year later, by June 2014, Conrad had graduated from high school, gotten a scholarship to college, and earned his captain's license. That must have been a really big day, Conrad getting his captain's license. It was. I was very proud of him. Are you feeling good about the place that he's in? I felt that he was still struggling, but I felt very, very positive that he wasn't going to do anything to harm himself. It was right around this time when Conrad recorded that private video sharing his innermost thoughts.

7:21I feel like I still have a long way to go to recover from this social anxiety, this feeling of insecurity. But if I keep talking, keep talking, it's going to get better. On July 12th, Conrad headed to the beach with his mom and two sisters. Lynn vividly remembers walking the shoreline with her son. He seemed in good spirits that day. We talked about school and he's like, I'm not sure where I am right now in my head. I said, well, you just got your captain's license. You don't have to worry about anything right now. He's looking toward the future. Yeah. When they returned from the beach, Conrad drove his sisters to get ice cream.

8:05He was laughing. I said something and he was like smiling. Conrad told his mom he was going to his friend's house and wouldn't be back for dinner. But later that night, Lynn says, out of the blue, her daughter got a text message from someone quite unexpected. It was around 10.30 that night. Michelle Carter is asking where Conrad is. And they have boyfriend and girlfriend now. This was news to Lynn. She knew Conrad and Michelle had only seen each other in person a few times. The next morning, Lynn woke up at 5 a.m. and noticed Conrad wasn't home. She called around and drove by his friend's house but couldn't find him.

8:47Conrad was missing. A son disappears, a mom worries, and a dad receives a troubling clue. A family friend said they saw his truck with caution tape around it. The news is about to go from bad to worse. He's like, are you sure? Like, what are you talking about? When Dateline continues.

9:19Word spread quickly. Conrad Roy III was missing. His family and friends, growing more frantic by the hour, searched everywhere for him. By mid-morning, his mom decided to call 911. Please record his eyes. That evening, about 24 hours after Conrad left his house, his father got a call.

9:46So you go down there to Kmart? And I think the police told my father that he was gone. An officer found Conrad dead behind the wheel of his pickup truck. His dad called Lynn to tell her the awful news. I couldn't even see. I felt like I was drugged. I couldn't eat. Slept in the same clothes for days. It was the most horrible time in my life. The rest of Conrad's family was in disbelief. I was like, are you sure? What are you talking about? I just saw him. It just felt like all the blood just drained right out of your body to hear that kind of news. Scott Gordon of the Fairhaven Police Department was assigned to the case.

10:36His first impression was suicide by carbon monoxide. It was apparent that he placed a water pump in the rear of his truck, and eventually he passed away as a result of the carbon monoxide from that. To those who knew Conrad best, it didn't make sense. Had they missed something? Conrad had been getting help, taking medication, and seemed hopeful about his future. His grandmother remembered him using that very pump to help out his dad just days before. I can still see that smile on his face, this little smirky smile that he always had. And his father recalled the two of them working on a job together a week earlier, setting up fireworks on a barge.

11:17We were laughing, we were watching fireworks. They seemed fine. When I left, the last thing I said to him was, I love you, and he said, I love you back. So his family wondered what pushed him over the edge. As they struggled with their grief, they got comfort from a surprising source, Michelle Carter. She reached out to Lynn through text messages, consoling her, saying Conrad loved her very much. Did you feel like you were getting support or just a connection to Conrad somehow? I mean, I told her I loved her. She told me so many great things about myself that he had said. I don't know, she's just there for me when I needed her.

11:55Conrad's aunts also remember getting messages from Michelle. She sent messages of condolences and that she never tried so hard in her life to save someone and that she wishes that she could have saved him. And at the wake, she came through and introduced herself. I was a little shocked, though, when she said, I'm Conrad's girlfriend. I was like, I had no idea. Never heard of her name. Among Conrad's things were goodbye letters he'd written to different people, like this one to Michelle. It was very positive. Keep doing what you're doing, Michelle. Keep moving on and doing great things. After reading this letter, you must have thought, oh, Conrad and Michelle really had a special friendship that he wrote her this letter.

12:38I was very happy that she was in his life. I thanked her for being there for him. Just weeks after Conrad died, Michelle contacted his family, saying she wanted to raise awareness for suicide prevention by organizing a baseball tournament. homers for Conrad. I was thinking, wow, this is really impressive. Here's a teenager, a high school senior, and she's only a month later starting to plan this large fundraiser. Conrad's whole family showed up. His Aunt Chrissy was impressed with Michelle, then just 17. I went up to her parents at that fundraiser and I said, you must be so proud of your daughter.

13:16She's quite an amazing girl. Unbeknownst to the family, back in Fairhaven, and Detective Gordon was digging around for answers, hoping to discover why Conrad might have taken his own life. I just found it odd that an 18-year-old would do it in that manner. The detective figured there were clues on Conrad's cell phone, which was found in his truck. And sure enough, when he powered it up, he discovered a string of text messages left on the phone from just one person. And that was a threat with Michelle Cotta. He had deleted all other text conversations with other people? Correct. And when the detective started reading the texts, he couldn't believe what he was seeing.

13:56It was one of those things where you keep reading and it just keeps getting worse. And that's what's kind of put everything in motion.

14:05Coming up, the text messages no one could fathom. I had to read them a couple of times to really sort of take it all in. Who had been texting what to Conrad? And I closed my eyes and I said, this is not real. when Dateline continues. Two iconic soap operas collide in a high-stakes showdown. Beyond the Gates and Young and the Restless come together for a must-see CBS crossover event. The drama reaches new heights as powerful families, long-held secrets, and unexpected alliances collide. Packed with love and betrayal, this crossover event changes everything. Don't miss the Beyond the Gates and Young and the Restless crossover event All this week on CBS and streaming on Paramount+.

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16:15Two days after Conrad Roy's death, Detective Scott Gordon of the Fairhaven Police Department had found a clue. And it was a bombshell. A string of text messages from Michelle Carter on Conrad's phone. What are you seeing? It was just a series of messages that seemed to be encouraging him to take his own life. Encouraging him to take his own life? To the detective, it was unimaginable. He learned Michelle and Conrad had been texting, like teenagers do, for almost two years. But a few weeks before his death, something changed. It seemed Michelle started a campaign to get Conrad to die by suicide.

16:56She even gave him suggestions on how to do it. Hang yourself. Jump off a building. Stab yourself. I don't know. There's a lot of ways. Gordon's partner at the time, Detective Glenn Cudmore, also worked the case. I remember when he was looking at it, it was something to the effect of, I can't believe what I'm reading. What kinds of things was she saying? Things like, you promised me, when are you going to do it? Why haven't you done it yet? You disappointed me. Yeah, I'll take care of your family. The detectives poured over thousands of text messages. And the more they read, the more disturbed they became.

17:30Like this exchange in the early morning hours before Conrad died. You can't think about it. You just have to do it. You said you were going to do it. Like, I don't get why you aren't. Conrad responded, I don't get it either. I don't know. Carter typed back, So I guess you aren't going to do it then. All that for nothing. I'm just confused. Like, you were so ready and determined. Conrad wrote back, I am gonna eventually. I really don't know what I'm waiting for, but I have everything lined up. And this one, on the morning of his death. Okay, I'm gonna do it today. Do you promise? I promise, babe.

18:08I have to now. Like right now, where do I go? And you can't break a promise and just go in a quiet parking lot or something. Have you ever seen anything like that in your career as a detective? No. It was clear to the detectives that Conrad had died by his own hand. But was what Michelle did actually a crime? Detective Gordon contacted assistant DA, Mary Claire Flynn. He said, I want to send you these text messages. If you could please just take a look at them. And I said, sure, I will. And it was just utterly shocking. She checked with Katie Rayburn, her colleague at the time, and they agreed those text messages warranted further investigation.

18:51I couldn't believe what was in them. I had to read them a couple of times to really sort of take it all in. Clearly, it's black and white for you that you know this is wrong. But is it black and white? We're going to go forward with this. This is a crime. I mean, I would imagine for you it's complicated. Yes, and with all investigations, it's our duty and our responsibility to follow the evidence where it takes us. And so the evidence was taking us to Michelle Carter. So the Commonwealth's office told detectives to keep digging and find out more about Michelle Carter. First reaction when you see her picture.

19:24She's young. She's just a kid. and the words that she was saying in their text messages, it just didn't seem feasible. During the investigation, Detective Cudmore went undercover. At that fundraiser, Homer's for Conrad, he secretly took photos of Michelle's every move. To confirm she was the one who sent those texts, he went one step further. He videotaped Michelle as he dialed the number he got from Conrad's phone. You're watching her? Yes. Answering the phone? Yes. That's a good sign. Yes, and we had the right person. Did you just hang up? Let it stay on for a few seconds, muted, and then she finally just hung up the phone.

20:04And I remember calling Scott and saying, are we sure we have the right girl? She just seemed so normal. A few months later, as the investigation continued, Detective Gordon decided to pay Michelle Carter a visit. He found her after school and approached her. Michelle, the reason why we came out here is because we were looking into Conrad's unfortunate passing, all right? And she has no idea. She's been watched. She has no idea. Does she look surprised? She, a little bit, but, you know, at that point, I don't think she understood really what we had and where we were going with it. At first, Michelle told the detective she tried to talk Conrad out of suicide.

20:46How did you help him to try and see that suicide that it wasn't the right thing for them? Well, I told him a lot of things. I told him that I loved him. I told him that a lot of people loved him. Yeah. And that, like, without him, nothing would be the same. Like, I had personal issues that I got help for, and I told him that he should come with me and get the help that he needed. But he refused. He said that no one would be able to help him, and it would make him worse if he got help. Then, the detective asked her about having contact with Conrad on the day he died. Do you think you had contact with him that day?

21:26Um, I think so. Yeah. The detective knew that was a lie. We have a search warrant for your phone. Okay, so we'll be taking her. Wait, so you're taking my phone? Yes. When we took her phone, I think she started to understand a little bit that we were looking a little more further into it than she expected. He followed her home and says Michelle's parents were very cooperative. They provided us with everything we needed. And that day we left with her cell phone and her laptop. Michelle has to know what's going on. But her parents, are they totally in the dark? Yeah, I believe so, absolutely. After going through all the evidence, including Michelle's phone and computer, prosecutors were convinced Michelle was criminally responsible for Conrad's death.

22:14Words can harm, and you don't have the ability to just say your words aren't criminal because they're protected by free speech. And there's precedent for people that have encouraged others to commit suicide to be charged with involuntary manslaughter. What is the law here in this state, and how did it guide you? Well, the charge of involuntary manslaughter, it involves wanted and reckless conduct that she could have caused someone's death and did cause someone's death. In other words, the prosecution believed Michelle should have known that encouraging Conrad to take his own life could result in him dying.

22:47Prosecutors now had the difficult task of telling Conrad's family what they had uncovered. It was just unbelievable. I just kept thinking, she's holding his head underwater. You could tell that he did not want to die. Her messages overpowered him. I closed my eyes and I said, this is not real. How can someone have an involvement in someone's death? I'm only encouraged. Did you just feel like you'd been duped? She's been consoling you this whole time. I'm a very forgiving person, and the only thing I can say about the ways that she was with me is that she's just really, really not well. The grand jury indicted Michelle for involuntary manslaughter.

23:38She pleaded not guilty. That's when the world heard the story for the first time, and the debate began. Was Conrad's death a suicide or a homicide? Coming up, a jaw-dropping theory about motive. Why would she do this? Because she wanted the attention. And at trial, Michelle makes a stunning decision. Are you doing that only involuntarily? Yes. Is it a choice she'll regret when Dateline continues?

24:18Michelle Carter was facing involuntary manslaughter charges for doing something teenagers do all the time, texting and calling each other. And the world was watching. Prosecutors Mary Claire Flynn and Katie Rayburn understood why. This affects everybody. Adults, teenagers, even parents with kids who don't even have phones yet. Absolutely. I think it's good to be thinking about what you're putting out there in the world because once you send it, you can't take it back. Prosecutors believe Michelle's words and actions caused a vulnerable Conrad to take his own life. He described his fragile state in that video diary.

25:00racing thoughts, suicidal thoughts, and flashbacks of hard times. And prosecutors learn Michelle did more than send text messages to Conrad. As deadly carbon monoxide filled the cab of his truck, Michelle was talking to him on the phone. There were two phone calls after the last text message. One from him to her, 41 minutes, and then one from her to him for over 42 minutes. But how would they ever know what was said on those calls? Detectives poured over thousands of text messages, and they got their answer. But lo and behold, on her phone, there was text messages to her friends describing what that phone conversation was like.

25:47The detective says a message Michelle sent her friend, Samantha Boardman, explained it all. Sam, his death is my fault. Like, honestly, I could have stopped him. I was on the phone with him, and he got out of the car because it was working and he got scared, and I told him to get back in. And as much as we were in shock about her language prior to that, once we read that, that was really disturbing. Prosecutor Flynn says another text message to that friend made it clear Michelle knew what she'd done was wrong. She said, Sam, I just found out from his mother that detectives have some of his things and are going through them to see if anybody texted him or encouraged him.