Long time gone

Facing a 160-year sentence for non-violent
robbery, Derek Twyman thought he might
die in a U.S. prison. Then a N.B. law student
took an interest in his bizarre case

Derek Twyman still wakes up most days just before 5 a.m. and searches the darkness for his black boots. In his mind, it’s almost time for the count — and every prisoner must be counted.

There’s no guard outside his cramped room in a northwest Toronto apartment, no cellmate to greet, no slow shuffle down to the cafeteria. But nearly 30 years in a U.S. prison turned this morning requirement into a ritual, a way to mark the days as one faded into the next.

Indeed, six weeks into his newfound freedom, Twyman is still adjusting to a new routine.

“It’s kind of been a whirlwind, a little bit overwhelming,” he says, sitting at a kitchen table that looks unusually small against his hulking six-foot, four-inch frame.

Twyman puts the length of his incarceration into perspective by pointing out that when he was locked up, “phones were the size of a shoebox.” As such, the Toronto of 2017 might as well be Mars. Even the simplest things can be a problem.

"To think, for a completely non-violent, property-related offence, someone could die in prison."

“The other day I was looking for some pants, and everyone tells me, ‘Get ‘em on the internet, they got good ones on the internet,” the 54-year-old recalls with his unplaceable drawl. “And I thought, I don’t have a credit card or nothing. I don’t have an I.D. yet. I can’t even open a bank account.”

Many of these mundane necessities are things he’s learning to do for the first time.

At age 26, Twyman — a Canadian citizen — was sentenced to 160 years for a spate of non-violent burglaries in North Carolina. Canadian and U.S. attorneys interviewed for this story have alternatively described it as “outrageous,” “incomprehensible” and “dumbfounding.” Though he always tried to maintain a positive outlook, Twyman faced the very real possibility of dying an inmate of the North Carolina corrections system.

Shane Martinez was a student at the University of New Brunswick in 2007 when he saw an ad Twyman had posted on a website for prisoners soliciting legal assistance  online in the hopes that someone — anyone — might agree to help him.

“The first thing I noticed about the story was the length of the sentence, which was so long,” says Martinez. “To think, for a completely non-violent, property-related offence, someone could die in prison.”

Derek Twyman has found it difficult adjusting to life outside prison. (David Donnelly/CBC)

Derek Twyman has found it difficult adjusting to life outside prison. (David Donnelly/CBC)

Derek Twyman has found it difficult adjusting to life outside prison. (David Donnelly/CBC)

Martinez calls Twyman a “genuinely decent human being who just needed help,” and the way he sees it, Twyman “had been abandoned not only by the judicial system in North Carolina, but also by Canadian authorities.”

Twyman and Martinez ended up forging a long-distance friendship that led to an audacious intervention that played out over a decade and featured a large cast of characters: pro-bono lawyers in Halifax, a prominent North Carolina attorney who made his name locking up Klansmen — and, strangely enough, the judge who originally sentenced Twyman.


Born in Ottawa and raised in Oakville, Ont., Twyman was 15 when his father, then a furniture buyer for Sears Canada, moved the family to Winston-Salem, the biggest city in Forsyth County, N.C. Donald Twyman had purchased a furniture shop nearby, and the expanse of well-to-do neighbourhoods with names like Pleasant Garden and Summerfield made sense for a young family.

When Twyman heard of his father’s plans, he thought of the old TV series The Andy Griffith Show, which was set in the idyllic, fictional North Carolina town of Mayberry. While his three older siblings managed to adjust, Twyman floundered. He felt estranged.

“It’s tough to fit in, and then you start trying to fit in,” Twyman explains. “Lots of times you make some bad decisions and pick the wrong people to stick around.”

By his late teens, Twyman was living fast. He had a fascination with high-end cars, and the crew he hung around with liked to party. Before long, they were resorting to petty theft to support the lifestyle. That devolved into greater criminality, and in 1984, while he was still a juvenile, Twyman landed in front of a judge for the first time.

He was convicted of several burglaries, as well as the arson of an empty house, and ordered to begin a 14-year sentence at the Polk Youth Institution, a facility that now houses the state’s first “supermax” unit. There, he met Jason Southard, a fellow juvenile offender who, according to Twyman, became “as close to a friend as you can get in prison.”

Prosecutors would later allege that the pair plotted their first crimes together while serving time on the same block. At any rate, once they were paroled in 1988, the duo — now both in their mid-20s — got back in touch.

* * *

Jan. 12, 1989, marked the beginning of a spree of burglaries in the tony suburbs of Forsyth and adjacent Guilford County. Police testimony shows the burglars targeted precious metals that could be melted down and sold anonymously to local pawn shops. Sometimes they walked out with a few hundred dollars’ worth of silverware; other times, the loot was valued in the tens of thousands.

Investigators sensed that the homes had all been scoped out before they were hit, since the perpetrators always managed to avoid the owners. Many of the victims were upper-middle class professionals, and as the spree carried on into the spring, pressure on police started to escalate.

A detective working the case instructed all of the pawnshops in both counties to buy up all of the sterling silver that came through the door — and get the license plate of whoever sold it.

On May 15, Jason Southard stepped out of a Mercedes and into a little outfit called The Silver Shop. When police ran his plate, they discovered the luxury sedan was registered to a family business in Winston-Salem called The Colonial Furniture Shop.

Derek Twyman was arrested a few weeks later — as it turned out, police had got to Southard early and cut a deal. He had implicated Twyman in at least 10 burglaries, identifying specific houses and dates to detectives in convincingly granular detail. When officers searched Twyman’s Mercedes, they found his cell phone and flashlights in the trunk, as well as a scanner tuned to police channels.

While Twyman sat in custody, Southard’s story expanded. He and his wife, also implicated in the saga, painted Twyman as a sinister manipulator who’d plied Southard with alcohol and warped his vulnerable mind. Southard insisted that he himself had been a moderating influence in the scheme, even vetoing acts of violence.

“It wasn’t like they were implying,” Twyman recalls now, saying he and Southard did “maybe four or five” burglaries together. In the end, though, Twyman was charged with 54 felonies: 26 counts of second-degree burglary, 20 counts of larceny and eight counts of breaking or entering.

“By the time they came to arrest me, they didn’t want to know anything about nothing. They had their story,” Twyman says. “They had a rich kid from another country that they could pin it on, so it didn’t matter.”

* * *

With Twyman in custody, his family recruited criminal defence attorney John Hatfield, Jr. Hatfield was unequivocal: The state had amassed a formidable case and the only conceivable way Twyman could “salvage” his life was to enter into a plea agreement. Hatfield said the North Carolina parole commission had determined that a carefully crafted plea deal would see him free within 10 years.

“I know that is a long time but it is also a sure-fire way to resolve this problem,” Hatfield wrote in a letter dated Oct. 27, 1989. But by November, the attorney’s tone had grown more urgent. He warned the case was scheduled to be heard by a retired judge with a “reputation for heavy sentencing.”

Then, a glimmer of hope. Hatfield said if Twyman entered into a plea agreement, his case could be heard a few weeks later by a “young, smart, fair and willing to listen” judge named Thomas W. Ross. While Hatfield cautioned that many of the victims “will be personally known to” Ross, he assured Twyman that it wouldn’t amount to a life behind bars.

Still unwilling to plead, Twyman parted ways with Hatfield. But his new counsel wasn’t convinced he should change tack. He advised Twyman to take the deal, do the time and leave prison with enough of his life left to make something of it.

Exhausted, frustrated and running out of options, Twyman resigned himself to a decade behind bars. But what transpired inside the Guilford County courthouse that December was remarkable.

Twyman sat in silence as an assistant district attorney laid out the circumstances of each burglary he was charged for, as well as the details of all his past crimes. Several victims made the drive to Greensboro to give statements, including a local defence lawyer.

"I'm thinking, 'What is this guy talking about?'"

He told the court that his home had been burglarized while he and his family were at church, and that it amounted to a “rape” of their privacy. Then, addressing the judge directly, he requested that Twyman be sentenced “as harshly as the court may possibly do.”

“At this point, I wasn’t even really paying attention to it, to be honest,” Twyman says, reflecting on the day. He assumed his lawyer had his back. “I’m going to get 10 years, then I’m out — that’s what I was relying on.”

But the judge had other plans. Twyman was a “professional criminal” who took part in premeditated offences, and there was no reason to believe that given the chance, he wouldn’t do it again. Citing Twyman’s crimes as a juvenile, a perceived lack of remorse and his apparent lack of interest in helping recover stolen items, Ross sentenced Twyman to 120 years.

“There are times when individuals present such a danger to society that it’s the Court’s obligation to do whatever possible to protect society, and that has to outweigh any other purpose behind sentencing,” Ross said.

Twyman’s mind raced as a sheriff’s deputy took him quietly into custody. The weight of what had just happened had not yet settled on him.

* * *

Four hours later, the deputy suddenly returned. Ross had summoned everyone back to court. He wanted to change the sentence. Twyman thought maybe the judge had had second thoughts and decided to amend the sentence, shortening it to something closer to what his lawyers had anticipated.

Instead, Twyman says, “I go in and find out, he’s giving me 40 more years.”

Ross said that in his six years serving on the state bench, he’d never taken such a step before. “I do it on this occasion only because I feel so strongly about it.”

Twyman’s release date was now 2056.

He was breathless. “I’m thinking, what is this guy talking about? The lawyer, he’s not saying anything. He’s just standing there looking crazy at me.”

In a separate trial some months later, Southard was sentenced to 50 years for his role in the burglaries. (He would be paroled after having served fewer than 20 years.)


During the early years of his incarceration, Twyman moved between half a dozen correctional facilities. It was easier for him to shun friendships and turn inward, since he never knew if he’d end up in another prison.

His family would visit, but the sterility of the interactions — Derek, sitting sullenly opposite them at a metal table, barred from making physical contact — made them opt instead to speak by phone.

“It was very difficult on my parents,” says Twyman’s brother Kevin, who now lives in King, a small town not far from the family’s original home in Winston-Salem.

While Kevin Twyman became a dual citizen, his brother was only a Canadian citizen with a U.S. social security number.

In the 1990s, Twyman wrote a letter to the Canadian consulate in Atlanta to ask if it could make a diplomatic inquiry on his behalf to get a hearing where his sentence could be reconsidered. He was told in no uncertain terms that Canada does not interfere in the domestic legal affairs of foreign powers. It was then that he began to come to terms with the reality that he was more or less alone, with no idea of how to draw attention to his astounding sentence.

To pass the time, Twyman took courses in law, psychology, computer science, graphic design and public speaking. When he wanted to register for a class that was restricted to him, he got a buddy to sign up — and Twyman did all the work. He helped edit a prison newsletter and made eyeglasses for kids while earning certificates in several trades. He also trained rescue dogs.

At the same time, he strategized ways to recruit help to get out of prison early. In 2007, he posted a blurb on Writeaprisoner.com, a website where inmates can describe their cases and solicit legal assistance.

That’s when Shane Martinez, then a law student back in Fredericton, N.B., stumbled upon it.

“He is legally a citizen of Canada,” Martinez remembers thinking at the time. “I thought, ‘I’m just getting acquainted with the law now, but it would be an act of goodwill on my part to at least try to help.”

He wrote Twyman a letter and before long, the two were corresponding — often.

“Hi Shane, How are things in the legal world? Hoping all is well and you are OK. Things are fine here, made it through an earthquake and a hurricane,” one early letter reads.

“He had a habit of not putting the years on the letters,” Martinez observes. “Lots of months and days, but not a lot of years.”

The letters soon became more like legal strategy sessions, including requests for help obtaining printouts of germane case law and textbooks or working drafts of motions for new hearings.

Though resources were tight, Martinez did what he could to draw attention to Twyman’s story. He featured the case on his campus radio show and even had Twyman on as a guest by phone.

Martinez soon learned that he wasn’t the only one getting letters from Twyman. For decades, he had written to every state representative in North Carolina, to senators and governors, to lawyers and advocates — to practically anyone with a P.O. box. His father and brother Kevin would send him postage stamps and Twyman spent nearly every penny of his 70-cent-a-day salary to buy more.

He tried to highlight that five years after he was imprisoned, North Carolina adopted a new law that severely restricted judges’ personal discretion in sentencing. Under the state’s Structured Sentencing Act, his sentence would have been limited to about 14 years.

After 9/11, he shifted gears. The U.S. had ramped up deportations of foreign nationals in its jails, and Twyman argued it was a reasonable opportunity to send him north to finish his time. There was at least a hope for parole in Canada.

“I think for most people saddled with a sentence of 160 years, it’s easy to become depressed and feel hopeless and give up,” says Martinez. “But he never gave up. He kept fighting and kept focused on getting out.”

As for Martinez, he immersed himself in the North Carolina legal system, desperately searching for any technicality or argument that might get Twyman in front of a judge. He also sent a torrent of letters to Canadian officials. When politicians visited his law school’s campus in Fredericton, Martinez approached them on Twyman’s behalf.

In February 2009, Martinez managed to get a letter to Lawrence Cannon, then the minister of foreign affairs. Among its many responsibilities, Global Affairs Canada monitoring the circumstances of Canadians imprisoned abroad.

A representative for Cannon’s office eventually responded that consular officials “cannot become involved in legal processes in foreign countries, nor can they provide legal advice or pay legal expenses for Canadians abroad.

“I wish to assure you that consular officials are aware of Mr. Twyman's case and have been in contact with him to provide consular assistance and support.”

Twyman paints a less generous portrait of his interactions with the Canadian government. He says it was not uncommon to go years without hearing from Global Affairs.

A department spokesperson declined to comment on the case, citing privacy reasons.

Martinez says “the Canadian government has known he’s been there for decades and they’ve done next to nothing to assist him the entire time.” Martinez’s campaign was a last-ditch attempt to ignite any “level of diplomacy, dialogue or interaction” that could garner support for getting Twyman sent to Canada.

Theoretically, that should have been the easy part. Canada and the U.S. are both signatories of the International Transfer of Offenders Act, a multilateral treaty that makes just such an allowance.

But it wasn’t the sentence of 160 years that was ultimately keeping Twyman in North Carolina. It was in fact a steep restitution order that had come with his prison sentence.

Specifically, the judge had ordered Twyman to repay tens of thousands of dollars to the victims of his crimes. Each passing year added more interest, and a quarter century into Twyman’s sentence, the figure had reached more than $300,000 US. Until it was paid, in full, the state of North Carolina would not entertain any suggestion of a transfer to Canada.

Twyman and Martinez’s effort had largely stalled.

“It felt like we were spinning our wheels and we weren’t getting anywhere,” Martinez says.


In the spring of 2016, Twyman left a phone message for Halifax-based criminal attorney Mark Knox, who works closely with the 7th Step Society of Canada, an organization that helps criminal offenders reintegrate after release.

Derek explained the details of his case, and what Knox heard shocked him.

“Anyone you talked to about [the case] immediately said, ‘160 years? $320,000 restitution? No drugs, guns or violence?’” says Knox. “It’s just a very compelling factual scenario.”

Knox got to work, recruiting help from pro bono lawyers and volunteers from Dalhousie University as well as a retired but influential judge in Newfoundland. Together, they pressured MPs from the East Coast, federal ministers and senators to start making noise in Ottawa.

Their efforts breathed new life into Twyman’s campaign. Martinez — who had just returned from six months practising law in the Caribbean — caught wind of the stirrings in Halifax and jumped headlong back into the work.

Coming back to Canada was Twyman’s last, best chance to avoid dying in prison.

At the Nash Correctional Institute, he hung a two-by-three-foot Canadian flag in his cell. “Team Canada,” as they jokingly called themselves, had given him new hope.

Twyman praises his unofficial legal aides for their “encouragement.”

“Some days maybe I didn’t want to deal with it, but Shane and the others reminded me that there was a plan.”

All the while, Twyman kept chiseling away in North Carolina, sending letters to politicians and newspapers. It was at this point that a reporter in Raleigh finally agreed to travel to Nash to chat.

* * *

Those who run in U.S. legal circles, especially in the south, have likely heard the name James Craven III. He cut his teeth prosecuting Klansmen during the most ferocious years of the civil rights movement, and has spent more than four decades practising law since.

Craven also happens to be an old acquaintance of Thomas W. Ross.

After reading a piece in Raleigh’s News and Observer headlined “Canadian inmate serving 160 years: deport me and save money,” Craven decided to reach out to Ross, who had retired from the bench and was then the president of the University of North Carolina.

“He was appalled to learn Derek was still in prison,” Craven says. “He agreed that enough was enough.”

Ross had career connections that ran all the way to the state house. He put in a word to the governor’s office, as well as to the state parole commission.

Meanwhile, Team Canada continued its own influence campaign. Soon, they were all working together, moving on multiple fronts in both countries to secure Twyman’s release.

“There’s plenty of fault to throw around between North Carolina, Washington and Ottawa. Everybody dropped the ball. And it’s a damn shame,” Craven says.

Early this year, after nearly two decades of campaigning for his freedom, Twyman received news that he couldn’t quite believe: He was being considered for parole.

“Nobody, nobody makes parole the first time up,” Twyman says. “I met guys inside who went up for parole 12 times and were denied.”

The parole commission of North Carolina decided that he had qualified for full release. Twyman was officially cut loose in May 2017 — 27 years and four months after his sentence began.

Not only that, his pricey restitution order was waived.

* * *

And that should have been that.

But when Twyman finally walked out of Nash in early July, he was unexpectedly picked up by officers with U.S. Immigration and Customs Enforcement (ICE) and taken to a holding facility for foreign nationals awaiting deportation. For reasons never clarified by either ICE or Canadian authorities, Twyman spent another 118 days confined in conditions he describes as “considerably worse” than prison.

When the Canadian consulate in Atlanta was made aware that ICE intended to finally send Twyman north, it did not provide any updates to his legal team until the very last moment.

Close to midnight on Halloween, Martinez got word that Twyman’s transfer was in motion. The next day, two armed ICE officers escorted him on a late-night flight from Atlanta to Toronto.

Twyman says that once he saw the Canadian flag on the ground at Pearson International Airport in Toronto, “I knew I was good.”


Twyman passed through the arrivals gate at Pearson on Nov. 1 with only a light, navy blue windbreaker and a half-empty backpack. At first, he didn’t recognize the smartly dressed lawyer with the manicured beard and slicked-back hair that greeted him.

That’s because it had been nearly a decade since he’d seen a photograph of Shane Martinez. “Last time I saw him, he had that bald head,” Twyman says.

Because of that, Twyman’s first in-person meeting with the man he describes as his closest friend was anticlimactic. Twyman barely spoke as he wound his way, wide-eyed, through the terminal. Meanwhile, Martinez walked beside him, asking occasional questions that mostly went unanswered.

Twyman’s unruffled exterior finally broke when he recounted what the Canadian Customs official had said to him: “Welcome home.”

“It was nice,” Twyman says, tearing up. “I’ve been trying to get here for a while. It’s a good feeling to be back.”

Reflecting on Twyman's legal journey, Martinez admits it "does seem a bit surreal. There were definitely times along the path that I was skeptical about whether it was going to happen.”

Twyman is now staying with a paramedic who offered him free room and board while he looks for an apartment. But the crowds, the noise and the pace of Toronto are still somewhat destabilizing. On the street and in the subway, Twyman constantly catches himself doing “threat assessments.”

“I’m leery of people, because of the things I went through,” he says.

After years of advocating for his case and working with other inmates, Twyman had hoped to find employment in the paralegal field. But in Ontario, that entails two years of schooling. And the time and money required for that are both in short supply right now.

“I just need a starting point,” Twyman says.

He and Martinez make a point of speaking almost daily. Twyman initially struggled to articulate what Martinez’s help meant to him, but after a bit of reflection, he was able to put it in words.

“When I wrote to Shane, I must have been mailing about 100 letters a month. Sometimes I might get one back from someone, but then they’d disappear,” says Twyman.

“It’s easy to feel alone when it’s like that. But he was genuine, from the beginning. I won’t ever forget that.”

With files from Lisa Xing and Elizabeth Chiu.

Lucas Powers is a Toronto-based writer and photographer. He's reported for CBC News from across Canada.

Photography: David Donnelly | Editing: Andre Mayer

For more Toronto news, visit cbc.ca/toronto.