Zak and Michelle

10 Oct 2025 · 34 min · 9 chapters

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In short

The episode “Zak and Michelle” (Criminal) focuses on the Toronto 18 plot and how one of the accused, Zachariah Amara, later connected with journalist Michelle Shepard. Shepard, a Toronto Star national security reporter, describes receiving early tips about a northern training camp and helping break the story that led to 18 arrests in June 2006 under Canada’s Anti-Terrorism Act. Key claims include that the suspects were mostly young, middle-class Canadian Muslims, driven by anger over Afghanistan and Islamophobia, and that the plan targeted major sites in Toronto with fertilizer bombs.

Notable examples

Fahim Ahmad (16 years) and Zachariah Amara (life sentence after pleading guilty; alleged ammonium nitrate purchase). Amara recounts radicalization after 9/11, training with paintball and a real gun, and building detonators with an undercover informant. He discusses solitary confinement, SHU transfer, ISIS fixation in prison, and parole denial in 2021 before release in 2022.

Guests

Michelle Shepard (journalist) and Zachariah Amara (former Toronto 18 member, now on parole/halfway house).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Toronto 18: A National Security Threat

1:03 to 3:54

Michelle Shepard discusses her investigation into a group planning a terror attack.

“There was this great fear that there was going to be another attack.”

Media Coverage and Community Impact

3:54 to 6:22

Analysis of how the media reported on the Toronto 18 and its effects on the Muslim community.

“Did it feel like something could happen at any moment?”

Zachariah Amara: A Personal Journey

6:22 to 7:57

Zachariah Amara reflects on his identity and experiences leading to his arrest.

“Much of the coverage focused on two men that were considered the group's leaders.”

Life After Prison: Reaching Out

9:26 to 14:00

Zachariah Amara discusses his return to society and reaching out to Michelle Shepard.

“In 2023, Zachariah Amara decided to send an email to Michelle Shepard.”

Zach's Radicalization Journey

14:00 to 17:06

Learn about Zach Amara's feelings of anger and isolation following 9/11 and his gradual radicalization.

“I mean were you all on the same page or did you find yourself being more angry about it than others you were around?”

Planning the Attack

18:47 to 28:07

Explore the details of Zach's plans and the psychological turmoil he faced during his radicalization.

“In 2006, Zach Amara started planning to make three bombs.”

Zach's Journey After Parole

28:07 to 30:00

Learn about Zach's experience of life after being released from prison.

“He'd been in prison for almost 17 years.”

The Challenge of Reputation

30:00 to 31:37

Explore the struggles Zach faces with his identity post-incarceration.

“Today, Zach isn't allowed to use a smartphone and has to live in a halfway house.”

Perspectives on Change

31:37 to 32:23

Insights on dealing with perceptions of one's past and the possibility of change.

“I mean, I usually don't engage in trying to persuade someone who has strong views.”
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Transcript

Automatic transcript. May contain errors.

0:00Michelle Shephard:Hey, it's Ryan Reynolds here from Mint Mobile. Now, I was looking for fun ways to tell you that Mint's offer of unlimited premium wireless for$15 a month is back.

0:08Zakaria Amara:So I thought it would be fun if we made$15 bills, but it turns out that's very illegal.

0:15Michelle Shephard:So there goes my big idea for the commercial. Give it a try at mintmobile.com slash switch.

0:32Zakaria Amara:One day, with the help of science, you might be able to live forever. Forever. Your body will just need a couple tune-ups. Injecting bone marrow in your 40s, your kidney in your 50s, your heart in your 60s, and so on. and then potentially a whole body transplant by the time that you were 90. This week on Explain It To Me, the quest for longevity. Find new episodes Sundays wherever you get your podcasts.

1:03Zakaria Amara: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. And 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.

1:53Zakaria Amara: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. I 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.

2:34Zakaria Amara: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. But 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. I literally had the newsroom in the backyard. So I caught the eye of the photo editor who was tending the barbecue, and he knew what was going on, and another editor.

3:21Zakaria Amara:And we just dispatched a bunch of reporters, a bunch of photographers, and we went and blanketed the city to try and figure out what was happening. And then I went into the newsroom to pull the story together. In 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? And 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.

4:14Zakaria Amara:And the plan would have been catastrophic. I mean, it would have totally crumpled our, it would have been our 9-11. And 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.

5:09Zakaria Amara:What was the press coverage like at the time? Was this all over, all day, every day? All 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, Thread 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.

6:05Zakaria Amara:The various Muslim communities in Toronto were kind of made to answer for this case. And 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.

6:54Zakaria Amara:He was sentenced to 16 years in prison. The other was a 20-year-old named Zachariah Amara. The 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.

7:25Michelle Shephard: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 Zachariah 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.

8:07Zakaria Amara:I'm Phoebe Judge. This is Criminal.

8:17Zakaria Amara:We'll be right back.

8:47Zakaria Amara:We'll be right back. powerful clean you can feel good about. So go on, pick up a bottle of All Free Clear for your next laundry day. The most memorable gifts aren't found, they're made. Zazzle is a custom marketplace where you pick any product, a mug, a card, a tote, a phone case, and make it personal, a photo, a name, an inside joke, the kind of gift that actually fits the person. That's what 30 million customers have been coming back to Zazzle for over 20 years to find. Right now, save 25 % on your first order at Zazzle.com. That's Zazzle.com. Make it Z-amazing. In 2023, Zachariah Amara decided to send an email to Michelle Shepard.

9:35Zakaria Amara:Why did you want to speak to her?

9:39Michelle Shephard:You know, she was the one who broke our story. and 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.

9:56Zakaria Amara: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 don't know if you remember me, This is Zachary Amara, and I just served my time and out on parole. And I don't know why I'm reaching out to you. I don't want a story. But I've just been sort of thinking about you and the coverage, and I'm just saying hi, basically. I was surprised you 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, you know, really hurt him.

10:47Zakaria Amara: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. He's like, oh my gosh, I'm so sorry. What did you think when you saw a knapsack by a table by the window with a terrorism convict?

11:33Zakaria Amara: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? Has he changed? Zakamara's family moved to Canada from Cyprus when he was around 12 years old.

12:12Michelle Shephard: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.

12:27Zakaria Amara:The first time he saw snow in Canada, it reminded him of Home Alone. Zach struggled at school, but he eventually started making friends.

12:36Michelle Shephard: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.

12:48Zakaria Amara:In high school, he joined the Muslim Student Association, and he became close with two other students, Fahim Ahmad and Saad Khalid. They 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.

13:35Michelle Shephard:I still remember President Bush's speech, you know, you're either with us or with the terrorists. When 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 like I took it as an attack against my identity and the people that I was more identifying with more and more as you know the aftermath of 9-11 and so I was kind of very upset about it and angry

14:15Zakaria Amara: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?

14:31Michelle Shephard:There 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 him.

14:57Zakaria Amara:The Canadian Islamic Congress reported a spike in hate crimes in Canada after September 11th. Zach says he 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. Zach 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.

15:32Michelle Shephard: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.

15:59Zakaria Amara: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. They picked a place about two hours north of Toronto. 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.

16:44Zakaria Amara: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.

17:05Zakaria Amara:We'll be right back.

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17:56Zakaria Amara:Ritual is very clear about that. Ritual's essential for women 18-plus multivitamin contains nine key nutrients important for your brain, bones, and red blood cells. You take two capsules daily, and the capsules are made with a delayed release design. I appreciate knowing exactly what's in my vitamins. And on Ritual's website, I learned that the omega-3 I take comes from Canada, vitamin K2 comes from Oslo, Norway, and the iron in my multivitamins is from Utah. Ritual multivitamins are made traceable, which means it's easy to find out where the ingredients come from and why they're included. Ritual's Essential is also third-party tested for heavy metals and clean label project certified.

18:37Zakaria Amara:Instead of striving for perfect health, aim for supporting foundational health. Save 25 % on your first month at ritual.com slash criminal. That's ritual.com slash criminal for 25 % off your first month. 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. He 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.

19:22Zakaria Amara:Was there ever a moment in the planning process where you thought to yourself, what am I doing?

19:30Michelle Shephard: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 happened, 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. Again, you know, I am responsible for what happened. And honestly, I hold myself responsible more than anyone else in the case.

20:29Michelle Shephard: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. 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.

20:49Zakaria Amara: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. When the informant made the delivery on June 2, 2006, the Royal Canadian Mounted Police began making arrests.

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21:14Michelle Shephard:When I was arrested, I was relieved.

21:20I know it sounds strange, but I was relieved to finally be off this path.

21:29Zakaria Amara: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.

21:40Michelle Shephard: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.

22:04Zakaria Amara:On 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.

22:50Zakaria Amara:Zach 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.

23:10Michelle Shephard:So I asked, you know, 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 SHU is the most dangerous prison in Canada. and the Shoe is in a different province, so it would be like eight hours away from my family.

23:40Zakaria Amara:Did anyone tell you why you were being sent there?

23:45Michelle Shephard: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.

24:03Zakaria Amara: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. He 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

24:39Michelle Shephard: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

24:57Zakaria Amara: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. He 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.

25:33Michelle Shephard:That was difficult because, you know, he looked like a good man.

25:43Michelle Shephard:And 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.

25:59Michelle Shephard:So it was just difficult to accept that this is the people I looked up to and that this was the right thing to do.

26:11Michelle Shephard:You 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.

26:24Zakaria Amara:In 2021, Zach Amara 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. He 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.

27:09Zakaria Amara: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.

27:35Michelle Shephard:The word I used is, I said, I want you to interrogate me and to, you know, assess whether I really changed or not. And if I haven't, then, you know, you can keep me in prison for the rest of my life.

27:48Zakaria Amara: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.

28:16Michelle Shephard: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.

28:33Zakaria Amara:Zach was one of the last of the Toronto 18 to be paroled. He's now been out of prison for three years.

28:40Michelle Shephard:And it's initially, you know, obviously when anything good, something that's such a change happens, such a release, relief. There is, you know, 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 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.

29:43Michelle Shephard:That was very, very difficult.

29:48Michelle Shephard:But I got out of it. I can explain how, but it's going to sound like a self-help book.

30:00Zakaria Amara:Today, Zach isn't allowed to use a smartphone and has to live in a halfway house. He has a job fixing watches, and he's 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. But 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.

30:49So, yeah, I think given enough time, he could easily get there.

30:57Zakaria Amara:But 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.

31:31Zakaria Amara:There 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?

31:49Michelle Shephard:I 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 be ever be able to move past this all I can do is try

32:42Zakaria Amara:Criminal is created by Lauren Spohr and me. Nadia Wilson is our senior producer. Katie Bishop is our supervising producer. Our producers are Susanna Robertson, Jackie Sajiko, Lily Clark, Lena Sillison, and Megan Kinane. Our show is mixed and engineered by Veronica Simonetti. Julian Alexander makes original illustrations for each episode of Criminal. You can see them at thisiscriminal.com. And you can sign up for our newsletter at thisiscriminal.com slash newsletter. Michelle Shepard wrote about Zach Amara for The Walrus Magazine. We hope you'll consider supporting our work by joining our membership program, Criminal Plus.

33:21Zakaria Amara:You can listen to Criminal, This Is Love, and Phoebe Reads a Mystery without 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.

33:53Zakaria Amara:Discover more great shows at podcast.voxmedia.com. I'm Phoebe Judge. This is Criminal.

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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