The Tusker

10 Oct 2025 · 34 min

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Podcast Notes: Criminal - Episode: "Zak and Michelle"

Episode Overview Title: Zak and Michelle Air Date: 2023 Description: This episode explores the story of Zakaria Amara, one of the leaders of the Toronto 18, a group of young men arrested for planning bomb attacks in Toronto under the Canadian Anti-Terrorism Act in 2006. The narrative is enriched by insights from journalist Michelle Shephard, who reported on this case.

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Key Characters

  • Zakaria Amara: One of the leaders of the Toronto 18, arrested and sentenced to life in prison.
  • Michelle Shephard: A national security reporter for the Toronto Star who reported on the Toronto 18 and later corresponded with Zak after his release.

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Main Themes

  1. The Toronto 18
  2. In June 2006, 18 young men were arrested for allegedly planning to detonate bombs in Toronto.
  3. The group was largely made up of young Muslim males who felt marginalized and impacted by Canada’s involvement in the War on Terror and the rise of Islamophobia.
  1. Radicalization
  2. Amara experienced a shift in identity post-9/11, feeling anger towards Western actions in Afghanistan, which contributed to his radicalization.
  3. His isolation and connection with like-minded individuals led him to embrace extremist views and plan for violent acts.
  1. Media Coverage and Backlash
  2. The initial media coverage was extensive, often sensationalized, and included blatant Islamophobia.
  3. The press treated the case as a significant national threat, which further stigmatized the Muslim community.
  1. Personal Transformation
  2. Post-arrest, Amara underwent a significant transformation during his time in prison, where he reevaluated his beliefs.
  3. He sought rehabilitation and expressed regret for his past actions, which he noted in his letter during the sentencing process.

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Key Events

  • Initial Investigation: Michelle Shephard began investigating a group of young Muslim men rumored to be training for an attack. Despite skepticism from police, it was later revealed they were under investigation.
  • Arrests: On June 2, 2006, police arrested the Toronto 18, following a lengthy surveillance operation.
  • Prison Sentencing: Amara was sentenced to life in prison in 2010, where he initially faced harsh conditions, including solitary confinement.

Parole and Rehabilitation

  • After serving nearly 17 years, Amara was granted parole in 2022. He expressed a sense of relief but also feared reintegrating into society.
  • He participated in a counter-violent extremism program and showed signs of genuine transformation, which was acknowledged by law enforcement.

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Concluding Thoughts

  • The episode raises poignant questions about identity, redemption, and societal perception of those who commit violent acts. It delves into the complexities of human behavior and the potential for change, even in individuals linked to extremist ideologies.
  • Amara's ongoing struggle with his past and the public's perception emphasizes the challenges faced by individuals attempting to reintegrate into society after serving time for serious crimes.

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Key Takeaways

  • Impact of Media: The role of media in shaping public perception, particularly in cases involving marginalized communities.
  • Path to Radicalization: Understanding the factors that can lead to radicalization, including identity crises and social isolation.
  • Redemption and Identity: The challenges of redefining oneself after a criminal past, including the stigma that persists despite efforts to change.

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For further insights, listeners are encouraged to explore the episode and follow the podcast Criminal for more stories that delve into the complexities of crime and justice.

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Transcript

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0:00Support for Criminal comes from Ollie. Your dog's well-being starts with their food. And that's why Ollie delivers fresh human-grade food that your dog will love. Head to ollie.com slash phoebe, tell them about your dog, and use code PHEBE to get 60 % off your welcome kit when you subscribe today. Plus, they offer a happiness guarantee on the first box, so if you're not completely satisfied, you'll get your money back. That's O-L-L-I-E dot com slash phoebe and enter code PHEBE to get 60 % off your first box. Avoiding your unfinished home projects because you're not sure where to start? Thumbtack knows homes, so you don't have to.

0:37Don't know the difference between matte paint finish and satin? Or what that clunking sound from your dryer is? With Thumbtack, you don't have to be a home pro. You just have to hire one. You can hire top-rated pros, see price estimates, and read reviews all on the app. Download today. There was this great fear that there was going to be another attack. There was, of course, 9-11, then the anthrax scare. but everyone was worried about the next big one. In 2005, Michelle Shepard was a national security reporter for the Toronto Star. She started hearing from sources that Canadian authorities were keeping an eye on a group of young Muslim men in Toronto.

1:23And then I started hearing stories about a northern training camp and these young boys were up in the woods north of Toronto training for an attack. It all kind of sounded quite far-fetched. And to be honest, I think my editors thought I was just being a bit conspiratorial and there wasn't really a story there. But I kept saying, you know, something's going on and sort of putting the pieces together. Michelle says she talked to a source with the police to see if they knew anything. They actually laughed. They said, oh, that sounds pretty funny. A bunch of guys running around the woods with guns.

2:02I think I would have known about it. And what I found out much later was that call kind of put off alarm bells because at that point there was an investigation going on. I was getting accurate information, and they were very worried that a journalist knew anything about this. In June of 2006, Michelle was hosting a barbecue at her house. My husband actually works at the Toronto Star, and we used to have an annual barbecue in our backyard for all the interns. We have a small house in Toronto, a small backyard, and it was packed with, gosh, it was probably about 60 of us, editors, photographers, reporters, the interns.

2:47But it was about 8 o 'clock, I guess, and my phone rang and it was somebody, a source, saying it's going down. She heard that police were starting to make arrests.

3:28In the end, 18 people were arrested under the Canadian Anti-Terrorism Act for planning to set off bombs in Toronto. They became known as the Toronto 18. The youngest was 15. Police had been investigating them for about two years. They'd been using wiretaps and undercover informants. Did it feel scary? Did it feel like something could happen at any moment? Even though everyone had been worried after 9-11 there would be another attack, it still seems sort of incredible that there were 18 people planning to blow up downtown. And the plan would have been catastrophic. I mean, it would have totally crumpled our, it would have been our 9-11.

4:14And tell me a little bit about who these 18 men were. You know, it's hard, you can't really put them in one category. Every single suspect, you know, had a different backstory. But in very general terms, they were young Muslim boys. Some were, you know, young, were juveniles, and others were older. They, majority, you know, they were kind of middle class, all Canadian. But, you know, quite generally, they were angry with Canada's involvement in Afghanistan. And they were, you know, felt the backlash of Islamophobia in the community. What was the press coverage like at the time? Was this all over, all day, every day?

5:09All over. And I remember the morning that they first came to court. And there were snipers on the roof. There had to be, I think every media outlet in the U.S. was there. It was huge. It was a, I mean, I'm trying to think if we've had a bigger case here in Toronto. And I don't think we have in the time that I've been reporting. One newspaper ran the headline, Threat on the Homefront. Another article read, a Canadian jihad is apparently underway. In court and subsequent days, anybody who walked into the courthouse who wore a hijab or had a long beard had a microphone shoved in their mouth. The various Muslim communities in Toronto were kind of made to answer for this case.

6:07And now looking back at some of the pieces that were written, and they're just so blatantly Islamophobic. There was one, a colleague at another paper, wrote something to the effect of, you know, all the suspects had a first name Mohammed, second name Mohammed, last name Mohammed. Much of the coverage focused on two men that were considered the group's leaders. One was Fahim Ahmad. He was 21 years old when he was arrested. He pled guilty to participating in a terrorist group and instructing others to carry out activities for that group. He was sentenced to 16 years in prison. The other was a 20-year-old named Zachariah Amara.

6:55The Toronto Star ran a picture of him on the front page and reported that he'd bought three tons of ammonium nitrate to make bombs. He pled guilty to two charges of terrorism. In 2010, he was sentenced to life in prison. Well, let's just start with you introducing yourself. That's probably the most difficult question. How do you do that with a past like mine? So do you just stick to first name, last name? Do you get it straight into the crime which defines you? My name is Zachary Amara, and I'm a returning citizen to society after spending nearly 17 years in prison on a life sentence. I'm much more than that, but for now, that's how, I guess, that's the most honest way to introduce myself without hiding.

8:00I'm Phoebe Judge. This is Criminal.

8:11We'll be right back.

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9:40In 2023, Zachariah Amara decided to send an email to Michelle Shepard. Why did you want to speak to her? You know, she was the one who broke our story. And I, you know, I couldn't talk to every single member of the public. But at least I could reach out to as many people as I could. Michelle Shepard remembers when she first read Zach's message. And it started something to the effect of, I hope this doesn't alarm you, which is always alarming, right? And he just said, I, you know, I don't know if you remember me. This is Zachary Amara, and I just served my time and had a parole. And I don't know why I'm reaching out to you.

10:32I don't want a story. but I'd just been sort of thinking about you and the coverage and I'm just saying hi basically. I was surprised he reached out to me. I kind of had assumed that he would want nothing to do with journalists and would have felt that the coverage of the trial had really hurt him. That was just my impression. I was just surprised that he wanted to reach out to me. so I wrote him back and I said I'd be happy to meet for a coffee if you want we went to a coffee shop on one of the university campuses and I was running late and he got there before me and then he sent me a text saying I've got us a spot by the window I'm just going to go pray BRB, be right back so I went in, I got a coffee and he comes running up to me, and he's kind of looking panicked.

11:33He's like, oh my gosh, I'm so sorry. What did you think when you saw, you know, a knapsack by a table by the window with a terrorism convict? And I was like, oh God. And I laughed. I kind of liked that, I mean, dark, dark humor, of course. And I just laughed. I said, well, I'm obviously, you know, the worst national security reporter because the thought didn't even cross my mind. But, hi. And anyway, we got our coffees and we sat down. And gosh, I think we chatted for like two hours. I don't know, maybe even longer. You know, I was, of course, skeptical and dubious the first time I met him. I thought, well, is he really?

12:16Has he changed? Zacamar's family moved to Canada from Cyprus when he was around 12 years old. I do have a diary that I kept that I discovered later on. But in it, I talk about coming to Canada and you could tell I'm excited. I liked it. It was definitely an adjustment. The first time he saw snow in Canada, it reminded him of Home Alone. Zach struggled at school, but he eventually started making friends. I ended up finding my identity in my Muslim faith. And after that, I became kind of confident, and I was well-adjusted, I would say. In high school, he joined the Muslim Student Association, and he became close with two other students, Fahim Ahmad and Saad Khalid.

13:09They spent a lot of time together. Sometimes the three of them would write rap songs that they'd post online. Both Fahim and Saad were arrested as part of the Toronto 18. Zach says that things started to change for him after September 11th. He was 16 years old at the time. He remembers he was in chemistry class when he learned that hijackers had flown a plane into the World Trade Center in New York City and the Pentagon in Washington, D.C. In October, the United States began bombing the Taliban in Afghanistan. I still remember President Bush's speech. You know, you're either with us or with the terrorists.

13:53when you heavily rely on just one identity, like in the case of the Muslim identity and me specifically, and I look more like the people you're bombing, therefore I must be with them. I was upset. I took it as an attack against my identity and the people that I was more identifying with more and more as the aftermath of 9-11. And so I was kind of very upset about it and angry. What were other people around you at the mosque or at home saying about it? I mean, were you all on the same page or did you find yourself being more angry about it than others you were around?

14:42There was a general anger, but I think it's because the Muslim community felt the backlash of 9-11 and many people blamed them for it. And so as a minority, they're very afraid. They were on the defensive. But I, as a young man, didn't understand that and I was upset about it. The Canadian Islamic Congress reported a spike in hate crimes in Canada after September 11th. Zach Sessy and his friends started reading and posting on radicalist websites. By 2005, he'd stopped going to the movies and watching TV. He'd gotten married at 18, and he dropped out of college and was working at a gas station.

15:32Zak says that he was worried about the war in Afghanistan And how many people were being killed He says he started to feel that it was up to him To keep Muslims from being hurt in the war So the process of radicalization and isolation And just meeting with like-minded people Who had the same thoughts Took place over years And you just more and more isolate As we know as you grow more extreme or more radicalized, you tend to isolate within the same silo and kind of want to hear the same beliefs reaffirmed. Zach and his friend Fahim Ahmad started planning an attack. They recruited friends. And Zach looked for a place outside the city where he and Fahim could hold a training camp.

16:22They picked a place about two hours north of Toronto. know. They met the recruits there in December. Zach and Fahim told them they'd be practicing military maneuvers. They used paintball guns and one real gun for target practice in the woods. They took videos of themselves. Most of them slept in their cars. They went to a local Tim Hortons to use the bathroom. Locals noticed the men at the grocery store. They were usually wearing camouflage. Neighbors reported hearing gunfire in the woods. But police didn't do anything, because the men were already being watched closely. One of the men in the training camp was working with the Royal Canadian Mounted Police as an undercover agent.

17:16We'll be right back.

17:42We'll see you next time.

17:53beverage ingredients. Visit goodtoknowfacts.org Josie, it's your new nanny Polly. The hand that rocks the cradle, a Hulu original. What do you know about her? Now streaming. You think if you try hard enough, you can stop bad things from happening, but you can't. Good help. Get out! Is hard to find. No! You need me to do this. A Hulu original. The hand that rocks the cradle. Reddit R, now streaming on Hulu and Hulu on Disney +, for bundled subscribers. Terms apply. In 2006, Zach Amara started planning to make three bombs. He would fill U-Haul trucks with fertilizer and detonators and park them outside the Toronto Stock Exchange, the Canadian intelligence headquarters, and a military base in Ontario.

18:45He looked up how to build a fertilizer bomb at the local library. The same kind of bomb that Timothy McVeigh used to bomb a federal building in Oklahoma City in 1995. Was there ever a moment in the planning process where you thought to yourself, what am I doing? Yeah, definitely. I remember just, you know, parking, I think it was somewhere off the highway, and just breaking down in tears and praying and just not knowing what I was doing. And I've had like a number of those situations that happen, but I just, you just kept doubling down. I just kept doubling down and just keep moving forward. The best way that I can describe the way this plot transpired is it was kind of when you get on a treadmill and it just keeps going faster and faster and you can't get off.

19:55Again, you know, I am responsible for what happened. And honestly, I hold myself responsible more than anyone else in the case. And I believe if I wasn't around, probably none of this would have happened at all. And probably nobody would have been arrested. But that's how it happened. And it's just, it's an escalation, a doubling down, and then just being locked in a certain mental state where you just can't get off. Zach started to build a detonator that could be activated using a remote. He figured out how much fertilizer he would need. And then he bought fertilizer from a friend of a friend, who later turned out to be another undercover informant.

20:40When the informant made the delivery, On June 2, 2006, the Royal Canadian Mounted Police began making arrests. When I was arrested, I was relieved.

20:55I know it sounds strange, but I was relieved to finally be off this path. After his arrest, Zach was held in jail for three years. At first, he was put in solitary confinement. But eventually, he was allowed into the general population. Once I got out of solitary confinement, I was in the position where I had to keep defending, right? When you're looking at someone who tells you, oh, my brother works there, or my sister walks by that place every day, it's very difficult to defend.

21:39On January 14, 2010, he went to a sentencing hearing. Zach read a letter addressed to his fellow Canadians. Quote, I am certain that many, if not all of you, will never forgive me for my actions. I only wrote these words to simply let you know of how regretful and sorry I feel. As for the Muslims amongst you, I have an additional comment to make. I cannot imagine the type of embarrassment or anxiety you must have gone through in the days following my arrest. I am sure many of you received unwelcome attention and felt hopeless in trying to explain that the actions of a few were not endorsed by the community.

22:25Zach was sentenced to life in prison. At first he was told he'd be going to a prison a couple of hours from Toronto He was relieved that it wouldn't be too hard for his family to visit But he says when he got into the transport van He found out he was being taken somewhere else So I asked, I yelled and I said, where are we going? So another prisoner replied and he said, the SHU The SHU stands for the Special Handling Unit So when he said that, that's when my stomach sunk. And I felt completely devastated because the Shoe is the most dangerous prison in Canada. And the Shoe is in a different province.

23:10So it would be like eight hours away from my family. Did anyone tell you why you were being sent there? Initially, they never told me I was going there. In my case, they said, we're going to assess you in the special handling unit, and after six months, we will determine whether you'll be sent to another lower security prison. And that six months turned into six years. In prison, Zach says the isolation started to make him feel paranoid. He felt like he was being watched. He accused another man of being an informant, and he attacked him. He says his beliefs became more extreme than they'd been before his arrest.

23:54He says he became obsessed with watching coverage of ISIS. He made maps of their locations based on the news, and he started to believe that ISIS was coming to rescue him. But he says he also felt confused. When he watched the news, he couldn't understand why ISIS and al-Qaeda were fighting each other. If you guys are part of the same ideology, then why are you fighting each other? So that was the first question. And then after that, the brutality. It was very difficult. He saw stories about ISIS attacking mosques and churches, and reports about hostages being beheaded. He says it was hard for him to dismiss the number of people being killed.

24:43He started to become depressed. He later wrote that he was afraid that if he didn't believe in what ISIS was doing, it would mean that he had, quote, thrown my entire life away and brought suffering upon my family for no good cause. And then he heard that ISIS had beheaded an American journalist named Jim Foley. That was difficult because, you know, he looked like a good man.

25:18And then there was this other aid worker that was killed in Syria. You know, so, and then there was the burning of the Jordanian pilot.

25:33So it was just difficult to accept that this is the people I looked up to and that this was the right thing to do.

25:45You know, and I struggled with trying to make sense of what they were doing. I may not know what, you know, what's right at that time, but I know this is wrong and I have to be honest with myself. In 2021, Zakamara applied for parole, but the parole board denied his application. They wrote that they believed he had made an effort to rehabilitate himself, but they were unable to tell how much of a risk Zach still posed to the public. They said there were currently no programs in prison that would be able to assess Zach's rehabilitation. Reporter Michelle Shepard says Fahim Ahmad, Zach's former friend and one of the Toronto 18, was told the same thing.

26:32He was serving a 16-year sentence. He kept going up for parole, and the parole board would say, you know, well, you haven't completed these de-radicalization programs. And he would say, those don't exist, and they didn't exist in prison. And so it was this sort of, you know, almost Kafka process. A friend of Zach's put him in touch with a counter-violent extremism program, and they let him do phone sessions with a counselor. Zach also asked if the Royal Canadian Mounted Police, or RCMP, would interview him to assess whether he was still a risk. The word I used is, I said, I want you to interrogate me and to, you know, assess whether I really changed or not.

27:17And if I haven't, then, you know, you can keep me in prison for the rest of my life. The RCMP interviewed him about his childhood, his crimes, and his time in prison. Afterwards, they reported that Zach was no longer radicalized And that, quote, the change in your values, attitudes, and belief appears to be long-term In 2022, Zach was granted parole He'd been in prison for almost 17 years I don't think I believed it until I actually stepped out and I saw my sister You know, when that day came, I was always, maybe this is not happening. Maybe they'll change their mind. And there was always the chance that something would change.

Read the full transcript

28:08Zach was one of the last of the Toronto 18 to be paroled. He's now been out of prison for three years.

28:18It's initially, you know, obviously when anything good, And such a change happens, such a release, relief. There is enthusiasm, happiness, euphoria, excitement, energy, wanting to catch up, to move as fast as you can possibly move. And then, so that's kind of the initial stage. And then after that, there's that stage, the Shawshank Redemption stage, You know, when you remember that old man who gets out from prison after such a long time and he can't find his place in society and eventually commits suicide. So that was like a stage I had to go through recently, probably in my third year, end of second year, third year.

29:18That was very, very difficult. But I got out of it. I can explain how, but it's going to sound like a self-help book.

29:34Today, Zach isn't allowed to use a smartphone and has to live in a halfway house. He has a job fixing watches, and he started taking writing classes. Michelle and Zach have stayed in touch. Do you think he'll ever not be known as a terrorist? That is a good question. I hope so. I certainly hope so. You know, he's just, I guess, coming up to 40, so he's still got a long life ahead. There is another of the accused of the 18 who's actually a criminal lawyer now and doing really well. So, you know, and there's a couple others that were youths at the time who I understand are doing pretty well. So, yeah, I think given enough time, he could easily get there.

30:31But it's hard, you know. One Google search and your name comes up. So it's going to be difficult. And I think he's probably a little tired of this conversation, too. You know, that he doesn't want to always be known as the terror convict or even the redeemed terrorist, the repentant terrorist. Like, he doesn't necessarily want that label either. I think he just wants to move on.

31:05There are some people who will always think of you as a criminal and a terrorist. What would you say to someone like that? Someone who doesn't think that you can change or have changed?

31:23I mean I usually don't engage in trying to persuade someone who has strong views. I'm the type of person that if I sense someone has strong views and they're not willing to be persuaded I just don't argue with them. I just accept that this is the strong position that they have. You know, I'm not sure I'll ever be able to move past this. All I can do is try.

32:27The End

32:52We'll see you next time.

32:58without any ads. Plus, you'll get bonus episodes. These are special episodes with me and Criminal co-creator Lauren Spohr talking about everything from how we make our episodes to the crime stories that caught our attention that week to things we've been enjoying lately. To learn more, go to thisiscriminal.com slash plus. We're on Facebook at This Is Criminal and Instagram and TikTok at criminal underscore podcast. We're also on YouTube at youtube.com slash criminal podcast. Criminal is part of the Vox Media Podcast Network. Discover more great shows at podcast.voxmedia.com. I'm Phoebe Judge. This is Criminal.

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From the publisher

In 2006, a group of young men and teenagers were arrested under the Canadian Anti-Terrorism Act for planning to set off bombs in Toronto. They were known as the Toronto 18. One of the group’s leaders was a 20-year-old named Zakaria Amara.

Michelle Shephard wrote about Zakaria Amara for The Walrus magazine.

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