Zak and Michelle

Summary

Criminal Podcast – "Zak and Michelle" (Oct 10, 2025)

Host: Phoebe Judge
Guests: Michelle Shepherd (journalist), Zachariah Amara (former member of the Toronto 18)
Theme: An in-depth reflection on the Toronto 18 terrorist plot, the circumstances and motivations behind it, its personal and societal aftermath, and the path to change and reconciliation.

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Episode Overview

This episode of Criminal revisits the Toronto 18—a group of young men who, in 2006, were arrested for plotting large-scale bombings in Canada. Phoebe Judge explores the story through the eyes of Michelle Shepherd, the journalist who reported the case, and Zachariah Amara, once a central figure in the terrorist plot, now a parolee seeking a new life. The episode examines radicalization, community fallout, the justice system’s response, the challenges of rehabilitation, and the nuances of identity and redemption.

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Key Discussion Points & Insights

1. Initial Discovery & Reporting of the Toronto 18

[01:07–04:24]

• Post-9/11 Fear: Michelle recalls the omnipresent anxiety of further terrorist attacks post-9/11 and the anthrax scare.
• Reporting Origins: Michelle Shepherd (then a Toronto Star national security reporter) first hears about a suspicious group training in northern Ontario.

  “I kept saying, you know, something's going on and sort of putting the pieces together.” – Michelle Shepherd [01:33]

• Police Reaction: At first, authorities brush off her inquiries; only later does Michelle realize the investigation was active and her questions raised alarms among the authorities.

2. The Bust & Media Frenzy

[02:33–06:38]

• Live Newsroom: At a Toronto Star BBQ, Michelle gets a tip the arrests are happening:

  “I literally had the newsroom in the backyard.” – Michelle Shepherd [03:11]

• Arrests: 18 people, aged as young as 15, arrested for plotting bombings under the Canadian Anti-Terrorism Act.
• Community & Coverage:
  • The group is largely comprised of young, middle-class Canadian Muslims, often angered by international events and their marginalization at home.
  • Media coverage is intense and often Islamophobic:

    “Anybody who walked into the courthouse who wore a hijab or had a long beard had a microphone shoved in their mouth… looking back, they're just so blatantly Islamophobic.” – Michelle Shepherd [05:58]

3. Focusing on Zachariah Amara & The Plot

[06:38–08:10]

• Group Leaders: Focus on Fahim Ahmad (sentenced to 16 years) and Zachariah Amara (sentenced to life).
• Introducing Zach:

  “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.” – Zachariah Amara [07:28]

4. Michelle & Zach: A Post-Prison Conversation

[10:50–13:19]

• Initial Contact:

  “It started something to the effect of, I hope this doesn’t alarm you, which is always alarming, right?” – Michelle Shepherd [11:09]

• Meeting in Person: Their first coffee meeting is awkward yet revealing, with dark humor breaking the tension. Michelle remains skeptical about Zach's change.

5. Zach’s Radicalization Story

[13:19–17:08]

• Immigration to Canada: Arrived from Cyprus at age 12; found identity in Muslim faith and community.
• Post-9/11 Reaction: Deep anger and identity crisis following the attacks and anti-Muslim backlash:

  “When you heavily rely on just one identity... I look more like the people you’re bombing, therefore I must be with them.” – Zachariah Amara [14:47]

• Online Radicalization: Participation in radical online forums; slow isolation from broader society.
• Motivations: Driven by outrage at wars in Afghanistan and Iraq, seeking to "protect" Muslims globally.

6. The Training Camp & Unfolding Plot

[17:08–22:40]

• Camp Details: Paintball ‘military training’ in the woods, secretly monitored by police and infiltrated by an informant.
• Bomb Plot: Intended to target Toronto Stock Exchange, CSIS headquarters, and a military base—using U-Haul trucks and fertilizer bombs.
• Doubts and Escalation:

  “The best way that I can describe the way this plot transpired is… like when you get on a treadmill and it just keeps going faster and faster and you can’t get off.” – Zachariah Amara [21:21]

• Arrest & Relief:

  “When I was arrested, I was relieved. I know it sounds strange, but I was relieved to finally be off this path.” – Zachariah Amara [23:06]

7. Prison Years: Isolation, Further Radicalization, and Turning Point

[23:21–28:16]

• Solitary & Maximum Security: Sent to the “Special Handling Unit”—the country’s most dangerous prison, far from family.

  “That’s when my stomach sunk, and I felt completely devastated.” – Zachariah Amara [25:01]

• Initial Extremism: Continued radical beliefs, even more so in extreme isolation.
• Dissonance & Realization: Observing ISIS’s brutality on the news, Zach grows deeply disillusioned:

  “It was just difficult to accept that this is the people I looked up to and that this was the right thing to do… I may not know what’s right at that time, but I know this is wrong.” – Zachariah Amara [27:24]

8. Rehabilitation & Parole Process

[28:16–30:25]

• Programs Lacking: Both Zach and Fahim Ahmad faced “Kafkaesque” parole hearings—they were denied because there were no available de-radicalization programs.

  “He kept going up for parole and the parole board would say… well, you haven’t completed these de-radicalization programs. And he would say, those don’t exist.” – Michelle Shepherd [28:53]

• Taking Initiative: Zach participates in a phone-based deradicalization program and asks for an RCMP assessment.

  “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.” – Zachariah Amara [29:26]

• Release: RCMP reports confirm real change; Zach is granted parole after nearly 17 years.

9. Life After Prison & Ongoing Struggles

[30:25–32:11]

• Transition: Intense initial euphoria gives way to existential struggles.

  “There’s that stage, you know, the Shawshank Redemption stage… can’t find his place in society and eventually commits suicide. So that was like a stage I had to go through recently.” – Zachariah Amara [30:32]

• Parole Restrictions: No smartphone, limited freedom, lives in halfway house, works fixing watches, and takes writing classes.
• Ongoing Relationship: Michelle and Zach remain in contact.

10. On Labels, Redemption, and Moving On

[32:11–34:34]

• Enduring Label: Discussion of whether Zach or other former Toronto 18 members can ever escape the stigma of their crimes.

  “He doesn’t want to always be known as...the terror convict or even the redeemed terrorist...I think he just wants to move on.” – Michelle Shepherd [32:11]

• Public Perception:

  “I’m not sure I’ll ever be able to move past this. All I can do is try.” – Zachariah Amara [33:40]

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Notable Quotes & Memorable Moments

• “A bunch of guys running around the woods with guns. I think I would have known about it.”
  – Police source (recounted by Michelle Shepherd) [02:06]

• “If I wasn’t around, probably none of this would have happened at all… It’s just an escalation, a doubling down, and then just being locked in a certain mental state where you just can’t get off.”
  – Zachariah Amara [21:21]

• “Once I got out of solitary confinement, I was in the position where I had to keep defending… 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.”
  – Zachariah Amara [23:31]

• “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.”
  – Letter by Zachariah Amara to fellow Canadians, read by Phoebe Judge [23:56]

• “All I can do is try.”
  – Zachariah Amara [33:40]

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Timestamps for Key Segments

• 01:07 – Fears of terrorism and reporter Michelle Shepherd begins following a lead
• 03:08 – Arrests and Toronto Star’s real-time coverage
• 06:38 – Introduction of the two main suspects, including Zach Amara
• 07:28 – Zach Amara introduces himself after release
• 10:50 – Reconnecting: Zach reaches out to Michelle Shepherd post-release
• 13:19 – Zach’s background, immigration to Canada
• 14:47 – Radicalization post-9/11 and feeling targeted
• 16:44 – Process of radicalization and social isolation
• 17:08 – Planning the training camp and emergence of informants
• 21:21 – Questioning and doubting the plot; “treadmill” metaphor
• 23:06 – Zach’s relief at being arrested
• 25:01 – Sent to “the Shoe” (Special Handling Unit) in prison
• 27:24 – Disillusionment with ISIS and violence in prison
• 28:53 – No available deradicalization programs for parole
• 29:26 – Zach requests RCMP assessment
• 30:07 – Granted parole after nearly 17 years
• 30:32 – Difficult transition to life outside prison
• 32:11 – Will Zach ever escape the terrorist label?
• 33:40 – Closing reflections on public perception and change

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Tone and Style

The episode is empathetic and searching, blending journalistic rigor with deep curiosity, personal stories, and moral weight. The voices of Michelle and Zach are direct and at times raw, sharing dark humor, regret, and hope.

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Conclusion

This episode of Criminal offers a rare window into the life of someone once labeled a terrorist and his complicated journey toward redemption. It interrogates difficult questions of justice, forgiveness, and the possibility of change—both for individuals and society at large. The relationship between Michelle Shepherd and Zachariah Amara serves as a thread of cautious trust, reflection, and humanity, inviting listeners to sit with the grey areas behind the headlines and beyond the courtroom.

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For further reading, Michelle Shepherd has written about Zachariah Amara for The Walrus magazine.

Transcript

[Phoebe Judge]

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[Michelle Shepherd]

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.

[Phoebe Judge]

In 2005, Michelle shepherd 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.

[Michelle Shepherd]

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. But I kept saying, you know, something's going on and sort of putting the pieces together.

[Phoebe Judge]

Michelle says she talked to a source with the police to see if they knew anything.

[Michelle Shepherd]

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.

[Phoebe Judge]

In June of 2006, Michelle was hosting a barbecue at her house.

[Michelle Shepherd]

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, 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.

[Phoebe Judge]

She heard that police were starting to make arrests.

[Michelle Shepherd]

I literally had the newsroom in the backyard. So I caught the eye of the photo editor who was attending the barbecue and he knew what was going on. And another editor, and we just dispatched a bunch of reporters, 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.

[Phoebe Judge]

In the end, each 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?

[Michelle Shepherd]

Even though everyone had been worried after 911 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.

[Phoebe Judge]

And tell me a little bit about who these 18 men were.

[Michelle Shepherd]

You know, it's hard. You can't really put them in one category. Every single suspect, you know, had a different background story, 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.

[Phoebe Judge]

What was the press coverage like at the time? Was this all over, all day, every day, all over.

[Michelle Shepherd]

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 US was there. It was huge. It was a. I mean, I'm trying to think if we have had a bigger case here in Toronto, and I don't think we have in the time that I've been reporting.

[Phoebe Judge]

One newspaper ran the headline Threat on the home front. Another article read, a Canadian Jihad is.

[Michelle Shepherd]

Apparently underway in court and subsequent days in 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. And now looking back at some of the pieces that were written, they're just so blatantly Islamophobic. There was one. One 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.

[Phoebe Judge]

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. 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.

[Zachariah Amara]

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, that's how I guess that's the most honest way to introduce myself without, you know, hiding.

[Phoebe Judge]

I'm Phoebe Judge. This is Criminal. We'll be right back. Support for Criminal comes from Quince. It's the time of year to start looking for layers that will last you through the fall and winter. If you're looking to refresh your wardrobe without blowing your budget, Quince can help. They have quality essentials that feel comfortable and look refined. And by partnering directly with top factories, Quint is able to cut out the middlemen and send you luxury quality pieces at half the price of similar brands. I've tried some things from Quint's myself, like this nice black sweater from them that buttons up the front. It's the perfect weight for fall and I've been wearing it a lot. Sometimes I layer it over Quint's button downs with my blue chore jacket, also from Quince. Find your fall staples at Quint's. Go to quince.com criminal for free shipping on your order and 365 day returns now available in Canada too. That's qu-I n c e.com criminal to get free shipping and 365 day returns. Quince.com criminal support for criminal comes from netsuite by Oracle. If you're looking to plan for the future of your business, NetSuite by Oracle can help. NetSuite by Oracle can bring together your accounting, financial management, inventory and HR all in one top rated cloud ERP system. Putting everything in one place can give you the visibility and control you need to make informed decisions quickly. You'll see how all the parts of your business are doing in real time so you can figure out what's working well, what's and where you need to try something new, and built in forecasting tools will help you prepare for what's next. You'll spend less time looking backwards and more time planning your next move, no matter how much your company is earning. NetSuite by Oracle will help you respond to challenges and seize opportunities. Download the CFO's guide to AI and machine learning for free at netsuite.com criminal that's netsuite.com criminal that'S netsuite.com/ criminal. In 2023, Zachariah Amara decided to send an email to Michelle Shepherd. Why did you want to speak to her?

[Zachariah Amara]

You know, she, she was the one who broke our story. And I, you know, I couldn't. 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.

[Phoebe Judge]

Michelle shepherd remembers when she first read.

[Michelle Shepherd]

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 Adam parole, and I don't know why I'm reaching out to you. I don't want a story, but I 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. 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. And then he sent me a text saying, I've got us a spot by the window. I'm just gonna 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, 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 hu. 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. Is he really? Has he changed?

[Phoebe Judge]

Zacamara's family moved to Canada from Cyprus when he was around 12 years old.

[Zachariah Amara]

I do have a diary that I kept that I discovered, you know, later on. But in it, you know, talk about coming to Canada, and you could tell I'm excited. I liked was definitely an adjustment.

[Phoebe Judge]

The first time he saw snow in Canada, it reminded him of home alone. Zach struggled at school, but he eventually started making friends.

[Zachariah Amara]

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.

[Phoebe Judge]

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.

[Zachariah Amara]

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.

[Phoebe Judge]

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?

[Zachariah Amara]

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. You know, they were on the defensive. But I, as a young man, you know, didn't understand that, and I was upset about it.

[Phoebe Judge]

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 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.

[Zachariah Amara]

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, like 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.

[Phoebe Judge]

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. 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. 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, an undercover agent. We'll be right back. Thanks to Squarespace for their support. Squarespace is the all in one platform designed to help you make a great website. Whether you're just starting out or trying to grow your business, Squarespace gives you everything you need to choose a URL, show off what you're selling, reach more customers, get paid, and do it all while looking professional. Everything in one place, no matter what you're working on, whether it's a podcast, a special event, photography services, or a consultation business, you can customize your website to reach the right people. If you're creating video content like online courses, tutorials, or workshops, Squarespace has built in ways to support that. With Squarespace, you can upload your videos into an organized, paywalled library, and they make it easy to collect payment with thoughtfully designed invoices and online payments. Plus, they have tools that make it convenient for people to keep in touch with you, tools that help you send emails to potential customers or that let your customers schedule their own appointments. Check out squarespace.com criminal for a free trial, and when you're ready to launch, use the offer Code criminal to save 10% off your first purchase of a website or domain. Support for Criminal comes from Bombas. If you're looking for new socks that are good for every summer activity, you might want to check out bombas. If you're a runner, Bombas socks are built to keep you cool, help sweat evaporate quickly and prevent blisters. They also have pairs specialized for hiking, tennis, golf, and more. And if you have any plane travel ahead, putting on a pair of Bombas compression socks for the ride can help prevent prevent aches and pains in your legs. Plus, if it's a wedding, you're headed to Bombas. Ruffle and dress socks will help you stay comfortable no matter how late you keep dancing. I've tried socks from Bombas myself for running, but also for getting dressed up. Thanks to Bombas, I finally have no show socks that don't slip down and that don't stretch out in the wash. You can head over to bombas.com and use code criminal for 20% off your first purchase. That's B O M B A S.com code criminal at checkout bombas.com and use code CRIMINAL. In 2006, Zacamara 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. Was there ever a moment in the planning process where you thought to yourself, what am I doing?

[Zachariah Amara]

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 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. 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.

[Phoebe Judge]

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.

[Zachariah Amara]

When I was arrested, I was relieved. It was. I know it sounds strange, but I was relieved to finally be off this. This path.

[Phoebe Judge]

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.

[Zachariah Amara]

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.

[Phoebe Judge]

On January 14, 2010, he went to a sentencing hearing. Zach read a letter addressed to his fellow Canadians. 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. 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.

[Zachariah Amara]

So I asked, you know, I yelled and I said, where are we going? So another prisoner replied, and he said, the shoe. The shoe 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. So it would be way. It could be, like, eight hours away from my family.

[Phoebe Judge]

Did anyone tell you why you were being sent there?

[Zachariah Amara]

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.

[Phoebe Judge]

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.

[Zachariah Amara]

If you guys are part of the same ideology, then why are you fighting each other? So that was the first, you know, question. And then after that, you know, the brutality. It was very difficult.

[Phoebe Judge]

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.

[Zachariah Amara]

That was difficult because, you know, he looked like a good man. 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. 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, 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.

[Phoebe Judge]

In 2021, Zac 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 shepherd 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.

[Michelle Shepherd]

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.

[Phoebe Judge]

A friend of Zach's put him in touch with a counterviolent 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.

[Zachariah Amara]

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.

[Phoebe Judge]

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.

[Zachariah Amara]

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.

[Phoebe Judge]

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

[Zachariah Amara]

It's initially, you know, obviously when anything good, something that 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, you know, 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 commit suicide. So that was like a stage I had to go through recently, probably in my third year, end of second year, third year, that 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.

[Phoebe Judge]

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 started taking writing classes. Michelle and Zach have stayed in touch. Do you Think he'll ever not be known as a terrorist?

[Michelle Shepherd]

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 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, I think given enough time, he could easily get there. 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, you know, the terror convict or even the redeemed terrorists, the repentant terrorists. Like, he doesn't necessarily want that label either. I think he just wants to move on.

[Phoebe Judge]

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?

[Zachariah Amara]

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

[Phoebe Judge]

Criminal is created by Lauren Spore and me. Nydia Wilson is our senior producer. Katie Bishop is our supervising producer. Our producers are Susanna Roberson, Jack Isajiko, 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 [e-mail] and you can sign up for our [e-mail] newsletter. Michelle shepherd wrote about Zac Amara for the Walrus magazine. We hope you'll consider supporting our work by joining our membership program, Criminal. Plus, 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 plus we're on Facebook at ThisIsCriminal and Instagram and TikTok at CriminalPodcast. We're also on YouTube at YouTube.com CriminalPodcast. Criminal is part of the Vox Media Podcast Network. Discover more great [e-mail] I'm Phoebe Judge. This is Criminal. Support for Criminal comes from Saks Fifth Avenue Saks Fifth Avenue makes it enjoyable and effortless to shop for clothes and accessories that fit your personal style. Fall is here and maybe you're thinking about adding classic, reliable pieces to your closet. Carefully crafted items that you can turn to over and over for a lifetime. Whether you're looking for a blazer from Prada or Gucci loafers, Saks will make shopping feel completely customized. They have stylists to help you in store, and Special features on Saks.com can filter for what suits your style and tastes. So if you want a personalized, easy shopping experience, head to Saks Fifth Avenue for the best fall arrivals and style inspiration.

[Zachariah Amara]

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[Phoebe Judge]

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[Zachariah Amara]

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