The email began: “I hope you’re doing well and I hope this email does not cause you any anxiety. I really mean that.”
The name attached to the November 8, 2023, message—Zakaria Amara—was one I had not thought about in years, but there was a time when I had spent hours studying him from afar. Amara was one of the leaders in the 2006 terrorism case where eighteen Muslim men and youth, four under the age of eighteen, were arrested for plotting to blow up downtown Toronto targets and a military base.
Back then, I was the Toronto Star’s national security correspondent, and we covered the story extensively—weeks, months, years of ink. It was considered Canada’s first large-scale “homegrown terrorism” plot, a term that took on new significance after the September 11, 2001, attacks to describe suspects who became violently radical without ever leaving their borders.
The plan went like this: two U-Haul trucks, each containing a one-tonne fertilizer bomb, would be parked in front of the targeted buildings during the morning rush hour. A third bomb would simultaneously hit a military base.
Although the accused came to be known collectively as the “Toronto 18,” the group had broken into two factions after disagreements between some of the members. Amara, who was then a married twenty-year-old gas station attendant at Canadian Tire and a new father, called the shots for one of the groups. He appeared determined to act, and as police listened to him on wiretaps, he bragged that his attack was “gonna be kicking ass like never before.”
Amara went so far as to build a detonator and buy what he thought was a truckload of explosives from an undercover informant. “To put this in context,” Royal Canadian Mounted Police assistant commissioner Mike McDonell said at the time of the arrests, “the 1995 bombing of the Murrah Federal Building in Oklahoma City that killed 168 people took one tonne of ammonium nitrate.” McDonell was wrong: it was actually a little over two tonnes. Amara had ordered three.
Like Amara, most of the accused were educated young Canadians who grew up in middle-class households. They were angered by the war in Iraq and Canada’s involvement in Afghanistan, believing their actions would somehow convince Parliament to pull Canadian troops from the conflict.
But they were also far from a monolithic group and were motivated by a variety of personal reasons, spurred on by online propaganda. They were looking—perhaps Amara most of all—to escape their everyday lives for something more meaningful.
Journalists showed up from all over Canada, the US, and beyond to attend the suspects’ bail hearings in Brampton, and anyone who had a long beard or hijab had a microphone shoved in their face. Globe and Mail columnist Christie Blatchford wrote at the time that the accused “have first names like Mohamed, middle names like Mohamed and last names like Mohamed.”
Four years, many hearings, and hundreds of articles later, seven of the eighteen accused walked free, including three of the youths, who had their charges stayed. Another four had gone to trial and were found guilty. The remaining seven, including Amara, decided to plead guilty. In 2022, after nearly seventeen years behind bars, including years of solitary confinement and a lengthy stint at Canada’s most violent penitentiary, Amara was granted parole.
I was surprised to hear from him. The media’s coverage of the Toronto 18 case had been criticized in some quarters—not unfairly—for being sensational, and I assumed he’d want nothing to do with reporters. I replied the day after receiving his email. I told him that, after two decades at the Star, I’d left the newspaper in 2018 to focus more on documentary filmmaking, podcasts, and longer features but that I’d be happy to have a coffee. I was genuinely curious about how he was doing, how prison had shaped him.
We agreed to meet on the campus of Toronto Metropolitan University. I was running a few minutes late, so I sent him a text. “Got us prime real estate,” he wrote back. “Going to find a spot to pray. Brb.” As I waited in line for coffee, I spotted what I assumed was his unattended bag at a table by the window. Just minutes later, he came back looking distraught and apologizing profusely for how that must have appeared—a convicted terrorist leaving an unattended bag! I laughed and confessed the thought hadn’t even crossed my mind, which obviously made me a terrible national security correspondent. Throughout that first conversation, he seemed contrite, regretful, thoughtful, and pretty funny.
But I still had a journalist’s skepticism. He was a convicted terrorist and had been described by police as persuasive and manipulative. I wanted to believe he was a changed man—but was he?
For months after—as texts, emails, and coffee talks became regular—Amara shared stories of his new life back on the outside, and I got to know him better. He got a bike and would ride around Toronto on his days off work, relishing his freedom. His written correspondence had a lot of smiling emojis and exclamation points. But it was clear he had to work hard for that optimism as he also wraps himself in the guilt of lives ruined—not just his but those of his co-accused, friends, relatives, and especially his daughter. The more we talked, the harder it became not to want to write about him—to write the sequel. I knew he had a good story to tell, but I think it was something more than that.
Because what Amara really seeks is something he cannot control: redemption. And if he was indeed “rehabilitated,” I wanted to help him get it.
When Amara pleaded guilty in 2010, he tearily addressed the court: “I spent days upon days trying to summon words appropriate, meaningful, and deep enough to express my regret and seek forgiveness for my actions,” he told Justice Bruce Durno. “I would like to promise you and my fellow Canadians that I will use my sentence to change myself from a man of destruction to a man of construction. I promise, no matter how long it takes.”
But Amara’s path toward repentance wasn’t straightforward. His first three years in pre-trial custody were spent in solitary confinement in Milton’s Maplehurst Correctional Facility and Toronto’s Don Jail, where, he says, he became only more extreme in his views—determined to avenge the Muslim lives lost in the conflicts that followed the 9/11 attacks.
“There was a moment when I actually wanted to write, almost like a manifesto, condemning the process, condemning the government, condemning the war in Afghanistan, condemning the US, like just using that as a platform,” he says. He had planned to read that statement in court. But when he tried to write, he struggled to explain himself—to justify what he had planned. “I just couldn’t write a coherent piece.” That was the first small crack.
Soon after, he was transferred into the general population at the Don Jail, where he had some challenging conversations. There was a Jewish inmate, and they debated Palestine. There was a former soldier who said he had fought in the war in Afghanistan and held some nuanced views. And there was a banker from Bay Street whose brothers worked in the Toronto Stock Exchange, which had been one of the group’s targets. The banker was “more of a potential victim than anybody else, and seeing him and interacting with him made me reconsider. If somebody shows me that I’m wrong, I am willing to accept it,” Amara later told the court at his sentencing.
But when I ask Amara if he had really altered his views, he pauses and then says, “You know when there’s issues of domestic violence and the husband or the boyfriend feels awful? And he says ‘I’m sorry’ but he hasn’t really dealt with the core issues. You just feel sorry in that moment. Right?” In other words, to use therapy speak, Amara had not yet “done the work.”
That would come, he says, after he was given a life sentence and transferred to Quebec’s Special Handling Unit, or the SHU. The SHU, in Sainte-Anne-des-Plaines, is Canada’s most restrictive detention centre and is often referred to as the “last resort” for inmates who pose a risk so high that they cannot be managed in a regular maximum-security institution.
No one wakes up a terrorist. There are many factors and stages that can last years before police are involved.
Amara was devastated to be transferred to a place he described as a “den of lions,” home to inmates who had committed violence not just on the outside but while incarcerated as well. “You have to remember that, except for the terrorism cases, everybody is there because they are, in prison lingo, ‘established,’” Amara says. “You reach the end of the day and you’re just so relieved. Ten thirty is when everything is locked up and shuts down. All you can think is, ‘I made it,’ but then you remember, ‘I have to do it again tomorrow.’”
Amara was told he was there to be assessed. He ended up staying for six years. As the months dragged on—and without any type of therapy or rehabilitation—he relapsed.
