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