Chapter 1: What led to the escape of the prisoner John Maynard?
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I'm Lester Holt, and this is Dateline. She seemed to have a perfect life, but she also had a secret, one that would explode into the headlines. That must be a pit in your stomach when you hear that your inmate is gone. Yeah, he's a very, very dangerous person. He said a prisoner had escaped and Toby was missing. We assume that he took her prisoner to be used as a hostage.
They were concerned for Toby's safety.
We found out that she had taken a large sum of cash and two firearms were missing from the house. You think, could she be involved in something like this?
She had children, a husband. It seemed like it was a white picket fence type play.
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Chapter 2: How did Toby Young become involved in the escape plan?
But this time, they didn't. They didn't do it. They didn't follow procedures. The van belonged to Safe Harbor, a nationally heralded prison program that taught inmates how to train stray dogs for adoption. That day, several dogs had been picked up from the prison. John Maynard, it turned out, was one of Safe Harbor's dog handlers.
Investigators interrogated every inmate who had helped load the dogs into the van. They just kind of drill down and drill down and talk to all those folks until you finally get somebody that's willing to talk. Where does that lead you? Where that led was that we were very sure that he had left inside a dog crate.
There were other inmates that knew that because, I mean, he had to get in the dog crate and he had to have somebody fasten it shut from the outside and then load it onto the van. There were fewer guards at the prison on Sundays and only two prisoner counts. The weather may have helped Maynard, too.
The day of the escape was very cold. People didn't want to be outside. They were ready to get the dogs in the van and get them out of there. What they didn't know, of course, was that John was in one of the dog crates.
And that, investigators believed, instantly put the driver of the van in harm's way. the founder of Safe Harbor, a woman named Toby Young. She was one of the most popular and trusted volunteers at the prison, and perhaps the reason the guards let their guard down. Are you thinking Toby's life could be in danger? Oh, absolutely. Because we figure he's in for murder in the first place.
And so I just had visions of, as they get away from here, driving away, he pops out of the box and takes her literally hostage. And then how long before he's done with the hostage? Just gives you chills and fear of what could happen. Fears that Toby Young, who set out to help prison inmates, may be the victim of one. When we come back. Her family desperate.
People were trying to call her cell phone and there was no answer. We were just fearing for the worse. Warden David McCune was horrified. Not only had a dangerous criminal escaped his maximum security prison, he was possibly holding a hostage. Toby Young, the leader of the prison's successful dog training program. A woman so beloved, the inmates even gave her an endearing nickname, the Dog Lady.
She seemed like a model volunteer. Absolutely. You know, good background, great career, strategic planning. I mean, husband's on the fire department and good family. Now, McCune had to break the terrible news to Toby's family. Her brother, Tom Phelan, could barely comprehend it. You had to pinch yourself, say, all right, yeah, this is real. This is really happening.
Were you trying to reach out to her? Was everyone in the family trying to call her? Oh, yeah, people were trying to call her cell phone, and, you know, there was no answer, and we were just fearing for the worse. Toby's siblings got together at their parents' place. There were lots of them. Toby was the oldest of seven children. Was Toby someone that you all looked up to?
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Chapter 3: What were the immediate consequences of the escape for Toby and John?
By the time he realized what was going on and called for backup, Maynard had disappeared. So close. Are you just consumed by this 24-7? Oh, yeah. I just hanging out there in the office, listening for the phone, listening on the radio, just listening for everybody. The reports are coming in from the investigators. I just praying, you know, let this be one of the tips that gets us there.
While Department of Corrections officers and U.S. Marshals were searching for Maynard and Toby, other investigators were trying to find out if anyone outside the prison was helping Maynard evade capture. So they interviewed his family and friends, but found no evidence any of them were involved. Next, they turned their attention to the prison staff. Could one of their own have helped Maynard?
We know it happens. I couldn't even hazard a guess in 30 years how many staff that we disciplined or let go because of overly familiar relationships. I mean, it's a number, quite a number. But as far as they could tell, no staff member had helped him escape. And that left one person whose actions they couldn't yet account for, Toby. You trusted her? Yeah, I sure did. If he only knew.
Coming up, a critical discovery at a storage unit and the break that will change everything.
All these pieces of the puzzle started to come together and we're telling a story. Absolutely. When Dateline continues.
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Listen now wherever you get your podcasts. On the night before Halloween in 1975, 15-year-old Martha Moxley was murdered, but police failed to make an arrest. Until, in 2000, her one-time neighbor, Michael Skakel, was arrested. He was also a cousin of the Kennedys. The Kennedy connection is the reason that most people know about this case.
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Chapter 4: What challenges did investigators face during the manhunt?
I'm betrayed and I'm just misled. A violation of trust. But the wardens still believed that Toby's life could be in danger. Inmates will be manipulating you. And even if her view of it was we have a very romantic relationship, we're having this great future together, if we just get away with this, many, many times, it's not reciprocal.
I mean, Toby might have trusted this man, but I know that you sure didn't. Nope, sure did not.
Coming up, three states away. My gut feeling was telling me it was them. A chance sighting leads to a wild chase. Units started falling into play. Not only marked units on the ground, but helicopters.
Toby Young had turned from a woman who had never committed a crime to an apparent criminal on the run. Investigators issued a warrant for her arrest. The warden called the family to deliver the news. We were shocked, thinking that they have to be wrong. They have to be wrong. This can't be right. This is not the Toby I know. Exactly. There's no way.
I just was filled with questions on why she would do something like this. I had no idea, but I knew that she was my sister and that I loved her. It's one thing, you know, for her brother to support her as this is unfolding. It's another thing for her husband, because this is a betrayal. It's looking more and more like a betrayal. Pat was devastated, just like the rest of the young family.
They were absolutely devastated, and I can't blame them. What does Pat tell you? their sons about what mom has done. Yeah, it was very hard on the sons. It was extremely hard on them. They couldn't understand it. I mean, that was their mom. It didn't take long before this intriguing local story. The mother of two adult boys, a wife of 30 years. Blew up into national news.
No one close to Toby Young says they know why Toby would suddenly throw away her past and future.
Toby Young's family... We had international attention on this one. It was making the European newscasts all over the world virtually. The killer and the dog lady. Despite the suspicion that Toby had fallen in love with John Maynard, her family believed he had manipulated her, that she was the victim.
She had always been a loving mom. I don't think that they thought that she would willingly leave her two adult sons without telling them where she was going.
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Chapter 5: How did Toby's background influence her decisions?
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toby young had been found sitting alongside an escaped convicted murderer in a truck barreling down a tennessee highway just then this police car sped up from around behind us and cut over in front of us and slammed on their brakes And John said, these are trying to kill us. He floored it and he took off.
As John Maynard drove even faster with dozens of state troopers in pursuit, Toby wondered what had brought her to this moment. Why had she made the fateful decision to help Maynard break out of prison? When I pulled up that day, I was kind of sick to my stomach, and part of me was excited about what was gonna happen, and part of me was wishing that it had never gotten this far.
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Chapter 6: What was the nature of Toby and John's relationship during the escape?
And I don't know how I thought that that would work.
On that Sunday, Toby nervously drove the safe harbor van to the prison. After the dogs and the dog crate were loaded into the van, she drove back out, past the guards, past the barbed wire, fearing what would happen next and hoping a little that it wouldn't. And I did say, John, are you in there? And he didn't answer. And I thought, oh, thank God. He's not in there.
And I'll just go do a dog adoption. And we don't have to do this thing. And then I heard this manacle laugh. And I thought, oh, crap. He is in there. And I pulled over and I just stopped. And then he popped his arm out of the box that was in the crate and said, drive, Toby, drive. They traveled at night, mostly on backcountry roads.
But then, just 15 minutes from their hideaway, they got lost and Toby saw a side of Maynard she'd never seen before. He said, you know, I don't know why I brought you along if you can't even figure out directions. And he was all upset and mad and he was driving the truck really fast and swerving. Were you scared? I was scared at that moment.
I was really scared because I thought, I don't know who this person is. By the time they arrived at the cabin they'd rented, he was back to the charming, caring man she'd given up her life for. And here, for the first time, there were no guards or prison walls to keep them apart. So what's it like finally being able to be with the man you're in love with?
It was beautiful and it was wonderful and it was probably the best part of our relationship. Was the intimate part of our relationship. that you were finally able to share a bed together. Yes. You know, I felt so loved, and I felt so treasured, and I felt so worthy. And, you know, at that moment, I thought, well, it was all worth it.
Everything you'd done, saying goodbye to your family, your children, your mom and dad, possibly that you could go to prison. At that moment, it felt like this is why I did it. They passed the days playing cards and board games, over romantic dinners by candlelight. They made plans to create new identities and start a new life, perhaps in Boston. But it wasn't meant to be.
They had made a mistake in their plan, a big one. Remember, Toby had given the car dealer her hideaway address in Tennessee. This is the definition of almost a dumb criminal. That's right. I mean, no offense. It turns out I wasn't a very good criminal, I think. And apparently not that good at hiding either.
In disguise, they snuck into town from time to time to eat at a steakhouse, buy a guitar for Maynard, and then finally to see a movie and buy a GPS at the mall. The same mall where U.S. Marshal Jason Ladd spotted their truck. The first thing I noticed is there's a police car blocking the entrance ramp to the highway. And I said, wow, there must be some wreck up ahead or something.
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Chapter 7: What events led to the capture of Toby and John?
So many people feel betrayed by you. Yes, they do. I mean, I betrayed so many people's trust and love. I let the people down who cared about the dog program. I let the people down who worked at the prison. I let my family down. Did you ever speak with your husband after the arrest? I talked to him once. He said I'd ruined his life and his life was over.
We reached out to Toby's now ex-husband who didn't respond. But he exchanged emails with journalist Michael Mooney and told him he'd never taken Toby for granted and always supported her.
I don't think Toby's husband thought there was anything wrong with the marriage. I don't think he thought of their relationship as neglect-filled or bad in any way.
Toby pleaded guilty to aiding and abetting an escape and smuggling a cell phone into prison. She and her husband divorced the day before she was to start her sentence. The 27 months she spent behind bars were tough. She said she was placed on suicide watch three times. I was so broken and so I didn't know how I was going to make it through all this.
Every now and then she got a love letter from Maynard. One of them was like, oh, you know, I wish I could ride in on my white horse and rescue you from that prison they're keeping you in. But wasn't the fairy tale over at this point? Yeah. And finally, I got to the point where I was like, you know, I am done with this.
When she got out, Toby wanted desperately to repair the relationship with her two sons, but that proved impossible. Her older son kept his distance, and just a year after her release, her youngest son died of cancer. You know, when I went to visit him in the hospital, I told him that I always loved him, and I never stopped loving him. And he said, I know, Mom. I know you love me.
And I asked him if I could give him a hug, and he said no. I mean, when you hear a story like that, it wasn't worth it. No. Toby says she's written letters to many of the people she hurt, asking them to forgive her. Not many have responded, but one did. Warden David McCune. Hello, Dave. Hi, Toby. How are you? I'm good. Good.
I didn't think I'd meet you here again.
I know. Toby wanted to apologize in person, so he asked the now former warden if he'd meet with her, socially distanced due to the pandemic, at the place where it all happened. He said yes. I want to tell you, You know, that honor is something that's very respected and earned and not given lightly. And I know how much trust you put into me. And I betrayed that. And I'm so, so sorry about that.
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