Reflecting on a life when you chose to be a criminal; can you change?

Send to a friend

Send this article to a friend.

Jason Middleton. TINA COMEAU PHOTO

What makes a person the way they are? Why do people make the choices they do? Why choose a life of crime over obeying the law? Vanguard associate editor Tina Comeau recently sat down with Jason Middleton of Yarmouth to ask him these and other questions.



By Tina Comeau



Something bad happens in Yarmouth and Jason Middleton is the go-to guy at the top of most people’s suspect list.

He gets that. He’s not surprised.

Is it fair? Based on the life he lived, probably, he says.

Will it always be this way? Based on the life he’s trying to live now, he hopes not, he says.

If you’ve lived in Yarmouth for any amount of time you’re familiar with the name Jason Middleton, whether you’ve met him or not.

Middleton recalls once recently sitting next to a man in a bar. The man, not realizing whom he was talking to, was warning him about Middleton.

“That Jason Middleton is trouble with a capital T,” the man said, going on and on before finally asking the fellow seated next to him, “What’s your name?”

“It’s Jason Middleton,” said Middleton.

The man’s face suddenly got all flushed.

“It’s a good thing,” Middleton said to the man, “that I’m not that guy you were talking about.”

In other words, he may be Jason Middleton, but he says he's trying not to be that Jason Middleton anymore.

But how does a person become that Jason Middleton in the first place? The one who sold drugs? The one who spent a good part of his life locked up behind bars? The one who lived a violent past.

It’s a long story. One that starts out with a little kid growing up with his grandmother – Nan as he calls her – on Church Street, living in a house filled with aunts and uncles who felt more like sisters and brothers.

“I think I understood at an early age that we were poor,” says Middleton. “We went without a lot of things.”

But it wasn’t for lack of trying on his Nan’s part, he says, noting she worked more than one job. However it left many days when children were raising children in the household. Middleton would often tell his Nan that when he was old enough he was going to get a job and help out as much as he could.

Along the way his plan got altered.

For him, a pivotal turning point in his life is ‘that day.’ That day when he was on the front lawn of his Nan’s house and a car with workers from Children’s Aid pulled up. They were there to take him away. For a little boy, he believes he was 9 at the time, it was confusing. He was taken to a series of foster homes but he didn’t stick around, running away from one after another.

Eventually he was sent to the Nova Scotia Home for Colored Children in Dartmouth. You’ve probably heard about the stories of abuse that went on there. Middleton says he could tell you some stories of his own.

Already dealing with feelings of abandonment, anger and confusion, now add abuse to the list.

“I had no sense of belonging,” he says.

Later he ended up at the Shelburne School for Boys. Again, we’ve heard stories of what went on there. At the time nobody asked Middleton what his experiences there were.

“And I didn’t care to tell,” he says, finding solace instead with alcohol.

As a teenager, whose run-ins with the law also landed him in Waterville, he was learning tactics and strategies from those he was in custody with on how to make money.

Selling drugs? Not a bad job for a teenager he thought.

“I wasn’t really trying to have a lot of money,” he says. “I was just trying to have something to eat and a place to sleep and a pair of shoes without holes.”

Although, when in Rome . . .

Before long Middleton discovered it was easier in life to be angry and to act out. He also started stealing things. When he was caught the focus was on punishing him, not on trying to figure out why he was behaving the way he was. And so began a trend, he says.

“I didn’t know what I was going to jail for, but I knew I was going.” And now he wasn’t just surrounded in jail by others who had sold drugs or committed thefts. Some had stabbed people. They were serving time for violent offences.

And yet in the surroundings he often found himself in, Middleton decided that crime pays off.

Well, it pays off when you don’t get caught.

“When I started making money I could give my Nan some things. I could help my family with bills. It kind of intensified my criminality,” he says. “I didn’t like selling drugs, but it felt good to give them money.”

At the same time he was coming to terms with a visual impairment that he worried might one day leave him blind. He hadn’t done the things or seen the things yet that he wanted to. To do these things, he says, he needed money.


By the time he was 18, Middleton had decided he was going to be a criminal.

“I’m gonna be Scarface,” he says. “I’m gonna make a lot of money. At the end of the movie he gets shot but I’m not going to.”

He was smarter than that, he claims,  even if he was making really stupid, and dangerous, decisions. Ones that affected many others.

Eventually he made a decision that would not only be life altering for him, but life ending for someone else. And life changing for a family.

He and a friend got into an argument over drugs, according to the court, one June evening in 1993. The argument spilled onto the sidewalk .

According to the court record, Middleton had turned the man upside-down and dropped him on his head, although he insists he never intended to kill him.

“You didn’t think that by doing what you did it would kill him?” he’s asked now.

“No, I had done the same move to about 10 people before,” he says – a statement just as troubling.

"It wasn’t my intention to hit his head.”

Middleton was charged with murder but pleaded guilty to manslaughter.

What he did was cause profound hurt to another family. And nothing he could ever do or say would reverse the devastation he caused them.

Nor should it.


At the age of 21 Middleton was sentenced to six years in a federal institution after pleading guilty to manslaughter. Because of his size and his behavior other inmates, he says, saw him as a “big, tough, aggressive black man.” And so he played the part.

“If I couldn’t be all of those things I would have hoped to be, aspired to be, tried to be, I’ll be this,” he decided. “And that’s what I became.” Others in the penitentiary were pleased with his decision.

You’re one of us now, they told him.

“I made some very, very bad decisions in my life,” he says now. Still, when he was released from prison after his manslaughter sentence it didn’t mean he was finished with those bad decisions – decisions that have impacted many lives beyond his own.

“I’m not stopping being a criminal,” he knew at the time. “I’m just going to be better with not getting caught.”

Any half-hearted attempt of turning his life around didn’t last.

Not even years later when he married and became a dad through that marriage.

He couldn’t escape his troubles with the law. In 2000 it was an extortion case. The media labeled him and his many co-accused the Sopranos, only without the charm.

His was never a good lifestyle. It was violent. It was illegal. It left many victims in its wake.

And Middleton and his friends were not immune. Friends who weren’t being charged with criminal acts were dying. His associates, his calls them.

“They’re gone and it’s not to terminal illness, it’s to homicide and to overdoses,” he says.

Middleton was sentenced to 18 months on the extortion charge and opted to remove himself from his family.

“I didn’t want to drag the family through this. I didn’t know anything about being a father.”

But he knew this about his son.

“I knew that I loved him.”


Cont'd on next page....



Organizations: Nova Scotia Home for Colored Children, Shelburne School for Boys, Deeds house

Geographic location: Yarmouth, Church Street, Dartmouth Waterville Rome

  • 1
  • 2
  • 3
  • 4
  • 5

Thanks for voting!

Top of page