After serving 30 years of a 160 year sentence, Derek Twyman is ‘clicking along’ in Toronto

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Looking around the tidy bachelor apartment in the Junction Triangle in east Toronto, you’d never know it’s the first time Derek Twyman has lived on his own. 

He’s hung up dozens of picture frames on his living room walls.

As he sips a glass of ginger ale, Twyman adjusts the autographed head shots of celebrities, like Al Pacino and Robert de Niro. 

He wrote to them, and dozens more, to anyone who would listen, who he thought could help him get out of prison. They’re also a reminder, he says, of how all those years behind bars in North Carolina have shaped him, though it’s clear they don’t define him. 

« Everything seems to be clicking along pretty good, » he said, with a gentle southern drawl. « This is actually a walk in the park. » 

160 year sentence

Life was anything but when Twyman was younger. At 15, his family moved to Winston-Salem, North Carolina. In his late teens, Twyman fell in with the wrong crowd, trying to fit in after moving from Oakville, Ontario, where he was brought up. 

He and another young man would go on to burglarize homes in an affluent area. They targeted precious metals that could be melted down and sold anonymously to local pawn shops. Police instructed the stores to buy it all, and take down licence plate of whoever sold it. The vehicle registered back to Twyman’s family. His partner in crime implicated Twyman as the mastermind behind all the crimes. 

At age 26, he was sentenced to 160 years—​four consecutive life sentences—​for that spate of non-violent robberies. 

From the time Twyman started his life behind bars, he was tireless in his efforts to raise awareness about his case. 
He wrote thousands of letters, to family and strangers alike. When one of those letters reached a young law student by the name of Shane Martinez, it started a decade-long intervention that featured legal help from Toronto, to Halifax, to Raleigh, North Carolina.

Their efforts finally paid off last year. Twyman flew back to Toronto in November 2017 nearly 30 years after he was first locked up. 

Life after prison 

In the year since, Twyman has been doggedly working to get back on his feet, starting with an apartment and a job. During that time, he lived with the friend of one of the lawyers who helped get him released.

« I was looking everywhere, » he said. 

For six months, he found no success. House hunting proved to be difficult. They were either all too expensive.  In one instance, he found a place by Lake Ontario and had the rental application filled out, but the landlord told him he wouldn’t be comfortable with Twyman living there. « It was ironic because, underneath the unit was a cannabis store, » he said. 

‘I never give up. »– Derek Twyman

Having a 30-year gap in his work experience didn’t lead to success on the job front, either, as he sent out dozens of applications, often never hearing back.

« You have to do it, » he said. « So, I never give up. I’ve been in worse situations before and haven’t given up. » 

Eventually, in March, he found a job in retail, but is reluctant to share any more publicly for fear his past will hinder the present once again. 

He also found the modest apartment that he’s made his own. The only personal photograph displayed is a framed photo of him and a blonde woman he proudly calls his girlfriend who he met at work. He hasn’t yet been able to reunite with his brother, whose bad health doesn’t allow him to travel to Canada just yet. His father recently moved to British Columbia from the States and hasn’t had a chance to visit. Mom died while Twyman was still in prison.

Losing track of time

At age 55, Twyman views his adjustment to life as a free man in mostly practical terms. At first, he got lost on public transit, but quickly learned most buses eventually landed him at a subway stop. He also had to learn how to upload an attachment in emails, and use smartphones.

His biggest challenge has been the cost of living. 

« I could buy a huge house in North Carolina for the rent I pay here, » he said. « You got rent, you have to buy food. » 

When talking about the change from a rigid prison schedule to managing it all on his own, it’s the only time he gets reflective. 

« [In prison] everything is the same, over and over. One day you wake up and 10 years has passed and nothing’s changed, » he said. « Here, it’s the same situation, except you’re in a different situation. You end up losing track of time. » 

Derek Twyman thought he might die in a U.S. prison. Then a N.B. law student took an interest in his bizarre case. 8:46

Still, Twyman keeps pushing on. For him, it means saving enough money to pay for a paralegal program at a career college in Toronto.

« It’s an accomplishment, helping someone, » he said. « In the end if you’re making a difference, you’re doing pretty good. » 

The college has already saved him a spot in the new year, but Twyman doesn’t know if he’ll be able to save up enough money to pay for it just yet. He’s not worried, though. 

« I always try to look at the good side of things, » he said. 

« If you look at things that way, life’s just a whole lot smoother. I guess you could say I’m the happiest man in Toronto. »

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