From the outside, Toby Young appeared to be living the American dream. 

Married to her high school sweetheart, the 48-year-old had a large home, two grown boys, and was the founder of the nationally acclaimed non-profit Safe Harbor, a job her family believed gave her purpose and fulfillment.

But what they didn’t know was that Toby felt trapped — trapped in a marriage that had lost its spark and a life where she felt unappreciated and taken for granted. The desperate lengths Toby would take to break out of that life would stun her family, earn international attention, and forever link her to a convicted killer, according to Dateline: Unforgettable.

Who is Toby Young? 

As the oldest of seven children, Toby was always seen as a pillar of responsibility. She graduated from college summa cum laude with a degree in business administration and accounting, and married her high school sweetheart, Patrick, who worked as a firefighter. 

As she and Patrick raised their two young sons in Kansas, Toby climbed the ranks at Sprint, eventually becoming a manager at the telecommunications company.

But as she reached middle age, Toby’s seemingly perfect life began to crack. She was caught in a round of layoffs at Sprint, was diagnosed with thyroid cancer, and watched as her sons headed off to college.

Toby started Safe Harbor, an organization that relied on prison inmates to train stray dogs to prepare them for adoption.

Her brother felt the new career “gave her a purpose” and “seemed to complete her,” but Young would later tell Dateline’s Andrea Canning that trouble in her personal life had left her depressed. 

“I was just invisible because I was trying to be a good person and you know, I knew I was invisible to my husband and I just felt like everybody knew they could depend on me to do something, so they just quit even regarding me at all,” she said. 

Toby believed the trouble in her marriage began 20 years earlier after the couple lost their daughter, shortly after she was born.

“We never really dealt with losing Emily and you know, we just kind of buried it and moved on and I think when you have something buried that’s so significant, it’s just a wound that doesn’t heal,” she said. 

How did Toby Young meet John Manard? 

Toby found the perfect anecdote to her growing unrest in a surprising place: behind the prison walls at the Lansing Correctional Facility. 

Toby was a regular and trusted volunteer at the prison through her work with Safe Harbor. One of the men who handled the dogs was an inmate named John Manard. Manard was serving out a life sentence after being involved with a deadly carjacking at the age of 17 years old. 

A romantic spark ignited between the unlikely pair after Manard came to Toby’s rescue one day when she was being threatened by another inmate in the prison. 

She smuggled him in a cell phone and the two were soon sharing secret phone calls and text messages. 

“We would have these really deep conversations about, you know, life and the world, and this was something I’d been craving forever. Somebody to just have conversations with,” Toby recalled. 

One day when the pair were setting up for a dog event together, Manard leaned over and kissed her.

“It was like I was on cloud nine,” Toby said. “It just made it, like, unquenchable.”

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When did Toby Young break John Manard out of prison?

They decided the only way they could be together was if Toby helped break Manard out of prison and together, they set out to hatch a bold plan, relying on Toby’s established trust within the prison system to pull off the jailbreak.

On February 12, 2006, Toby arrived at the prison with her Safe Harbor van to pick up some of the dogs. 27-year-old Manard climbed into a cardboard box that was then loaded into one of the dog crates and packed into the back of the van. 

Although all vehicles leaving the prison were supposed to be stopped and inspected, the guards let Toby through without inspecting the vehicle because of her established trust with the staff.

“I just thought he was madly in love with me and I knew I was crazy in love with him and I remember thinking well, if this escape works or even if it doesn’t work, you know, I’m not going to have to stay in this marriage anymore,” Toby explained of her reasoning at the time.

Once beyond the prison gates, Toby and Manard drove to a storage facility where she had a getaway truck stashed inside a garage. They took off and headed to a remote cabin in Tennessee, where they planned to lay low and finally consummate their love for one another.

“It was beautiful and it was wonderful and it was probably the best part of our relationship … the intimate part of our relationship,” Toby said. “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.’”

What happened to Toby Young?

But the love affair would be short-lived. Nearly two weeks after the brazen escape, they were spotted in a shopping center parking lot by a U.S. Marshall and a high-speed chase broke out. During the wild chase, Manard lost control of the vehicle, which ultimately came to a stop just before it would have slammed into a tree.

Toby and Manard were both arrested and returned to Kansas. Manard was given an additional 10 years onto his sentence, while Toby served 27 months in prison after pleading guilty to aiding and abetting an escape and smuggling a cell phone into prison.

It wasn’t the only consequence for the midwestern mom. The plot also cost her marriage and the relationship she had with her sons. Her oldest son has chosen to keep his distance, while her youngest son died from cancer about a year after her release.

“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,'” she remembered through tears.

About 10 years after their tryst, Toby visited Manard in prison. 

“It was really, really good because it was truly closure, you know? It was good to just be able to sit down and fill in the blanks and then walk away,” Toby said. 

Today, there’s no longer a romantic spark between the unlikely duo, although Toby does wish her former lover the best. She’s remarried, now goes by the name Toby Dorr, and hopes to help others through a new book released in 2022, “Living With Conviction.” 

“I want to share my story to help women unleash themselves,” she said. “We have these emotional prisons that we built ourselves and we have the key to unlock them and be free of them.”

Toby even offered a little advice for other women feeling trapped in a relationship. 

“If you ignore the need to make a change until you become desperate, then you make the wrong kind of change,” she said. “Acknowledge you need to change something and then move forward and do it in a healthy way. If I had had the insight and the strength to do that 15 years ago, I could have picked a much healthier way to change my life.”