“The Cruelty Right Now Is Horrific”: A Veteran Reporter Recalls Her Most Challenging Assignments

Michelle Shephard is an award-winning author, journalist, filmmaker, and podcast host and producer. She’s the author of Guantánamo’s Child: The Untold Story of Omar Khadr and Decade of Fear: Reporting from Terrorism’s Grey Zone. Her films include the Emmy-nominated documentary Guantánamo’s Child, The Perfect Story, The Man Who Stole Einstein’s Brain, and The Way Out. Her most recent book is Code Name: Pale Horse, which she co-wrote with retired Federal Bureau of Investigation special agent Scott Payne, and which was published by Simon & Schuster in 2025.

Michelle and I talk about the kinds of things she’s witnessed while reporting in places like Guantánamo Bay; about how she, an unapologetically lefty journalist who has reported extensively on abuses by the police and other government forces, handled co-writing a book with a former FBI agent; and about the journalist/novelist she looks to as a model as she contemplates trying her hand at a work of fiction.

This interview has been edited for length and clarity.

You are indirectly responsible for the most remarkable group message I’ve ever received. For context, we are both part of this annual event called Newzapalooza. We were on this group email trying to figure out meetings and details. At one point, we were trying to set a date for a meeting, and your partner, Jim Rankin, replied with this message: Michelle may be away in Gitmo though.

Oh, that’s great. I remember that. I love dropping the I-may-be-in-Guantánamo line. It’s been a crazy chapter of my life for the past fifteen years now. I actually celebrated two birthdays—my thirty-sixth and I think it was my thirty-eighth—in Gitmo.

To back up, the reason I was going there for so long was, when I worked at the Toronto Star, I covered the story of Omar Khadr. He was the Canadian detainee who was fifteen when he was captured by the United States, taken to Guantánamo, and spent half his life there. That story fascinated me for a bunch of reasons, in part because I think what happened in his case told the greater story of what happened after 9/11 in terms of justice, civil rights, the war—it was just so rich with details. I wrote probably like 300 articles for the Star over the years. I ended up writing a book, my first book, on his story and then doing a documentary. So, I went back and forth for his case. But then I also started covering the cases of 9/11—the five men who were charged with the 9/11 attacks who, amazingly, have still not come to trial.

I think that message you mentioned was one where we must have been talking about that. It was my last time there, when Donald Trump just came in for his second presidency. It was also actually my first piece for The Walrus. I had pitched Carmine, the incredible editor there, this idea of going to Guantánamo. It was my twenty-eighth trip there. And then it happened to be sort of a little prescient, because when I was there on the ground in Guantánamo, covering this 9/11 hearing, was when Trump said, Let’s send them all to Guantánamo—there’s 30,000 beds available and ready to go. And I remember being there with my colleagues and being like, Nope, no, there isn’t.

Are you saying Trump just kind of pulled a fact out of his ass?

It’s hard to wrap your head around, I know, but it was pretty funny just to be able to fact-check right in the moment there.

I find it a remarkable place. I’ve been so lucky over my career to go to a whole bunch of places around the world, but I think it’s still the one that’s most difficult to explain. It’s so surreal. Reporter friends who’ve gone there, lawyers, others—we all agree: you can be the world’s best writer, and you still can’t quite capture the Orwellian nature of it, the Kafkaesque nature, whatever word you want to pull out. It’s a surreal place.

It seems like we have a lot of those now, especially post Trump’s second inauguration—one of those things in the world where you just say, Well, no, that can’t continue like that. We’d all get outraged to a point where that would have to shut down. And yet it’s there.

The sad thing really is that the turnover is so great. My good friend Carol Rosenberg, who used to be at the Miami Herald and now is with the New York Times, is the unofficial Guantánamo historian, because she was on the tarmac when the first detainees touched down. She spends half of her year there. She needs a Pulitzer for the work that she’s done. But, I mean, what are we at? We’re at four presidents: George W. Bush, Barack Obama, Trump, Joe Biden, and Trump again. There have been countless commanders. There have been countless judges. It is really frustrating, because you’re reinventing the wheel every time.

Carol, by far, is the veteran. But even I’m the veteran when we get, like, public affairs officers showing you around, and you’re like, Oh no, that’s where that happens. You’re the one with knowledge. But the reporting there has always been unbelievably frustrating—the conditions that they have, the restrictions.

This is what I was trying to explore in that first piece for The Walrus. It’s exactly as you said it; you put it really well. It’s amazing that this continued, and we can’t believe that it keeps going. And over the years, the Pentagon even had this kind of Orwellian language. They’d say, Don’t call it a prison. Call it a detention centre. We don’t call it interrogations. We call it reservations.

They invented the language to sanitize the place, and now in our Trump era, they don’t do that anymore. The way I ended that piece for The Walrus was that now “the cruelty is the point.” You don’t even need to hide what you’re doing. And that’s really dark. I mean, shedding light on dark places for so many years in what happened in the post-9/11 era, and now the fact that the administration and, in large part, society in general are embracing the darkness—that’s really depressing.

What it makes me wonder is, as a reporter who goes to these places, how are you then able to be in places where people are having fun, and there’s joy, and there’s laughter, and you’re just like, I can’t stop thinking about this family I met, or this person I met, or this situation I was just in twenty-four hours ago? Are you just a master of compartmentalization—I will deal with that when I work on the piece?

That’s a nice question. And I do think about this. For instance, on this last trip to Chad, on the border with Sudan, the stories that I heard in that refugee camp were . . . “heartbreaking” is not even a strong enough word. Just to hear what people have gone through, to get a glimpse into a genocide that we’re not hearing a lot about, would leave me speechless. I’ve been doing this a long time, but just the level of cruelty and violence there right now is horrific. And I would be doing the interview, and I wouldn’t even know a follow-up question at times. I would just say, “I’m sorry,” and kind of let the silence sit for a moment.

And yet, having said that, when I’m there, I’m okay—it’s not my pain; it’s their pain. I’m just in awe of the people who are surviving, but I feel good that I’m bringing their stories out, and they want their stories out, and I have a job to do. And life is actually quite simple. When you’re there, you’re staying safe, you’re doing your job, you’re trying not to get sick, and you’re trying to get sleep. It’s when you come home that it gets a little hard.

I always talk about that time when I was covering the famine in Somalia years ago, which was really, really devastating. I came home—and I call it my Starbucks rage. I was in a Starbucks, and there was a woman ahead of me berating a barista because her coffee wasn’t hot enough. And I just remember seeing red and being like, Shut the f— up.

However, I also think it’s given me PTSD growth. I certainly have had colleagues who have suffered from post-traumatic stress disorder, and I’ve always been kind of mindful of that. I’m just diagnosing myself, but I’ve read about this thing called PTSD growth, which is you actually almost become happier. You become more thankful for what you have. You recognize your privilege even more. And I actually really think I’m able to embrace that.

So, I come back, and I’m so thankful. I’m like, Oh, my gosh, I get to live in this house. I have a good family. I have people who are healthy, and I get to go to Newzapalooza and play the tambourine and laugh with friends. I’ve really, thankfully, been able to channel that.

I want to talk about the book with Scott. Totally fascinating book, but there were moments where I just had to pause, and I was like, This is kidding. This is just darkness. Going back a little bit, how did you get connected to this project and to Scott?

Since I left the Star, I’ve been doing podcasts as well. I did a podcast series for the CBC called White Hot Hate. The first season was about this group called the Base. This great Winnipeg journalist, Ryan Thorpe, had exposed this Canadian member in the military. Part of the reason that the Base basically dismantled as this neo-Nazi group was that there was an undercover agent, never identified. I did an interview with one of the fathers of the accused in Georgia, and he said to me, I knew my son was hanging out with this guy. He told me his name was Scott, and that man is either FBI or a pedophile, because he was a lot older than the other guys. And of course, the natural follow-up question is: You didn’t worry about your son hanging out with either? And he said, No, no, I didn’t, you know. No, it was fine.

So, he was right, because Scott was older than a lot of the members of this group. He was an FBI agent. Anyway, the podcast ran, and about three months later, the producer I worked with, Ashley Mack, she saw a Rolling Stone profile of an FBI agent named Scott who was this six-foot-four, tatted-out biker, bourbon-drinking, Harley-riding southerner. The article mentions the Base, and she’s like, That’s our Scott. I called the Rolling Stone reporter, and he was like, I was waiting for you to call. As they were working on that piece, they’d been listening to the podcast. And I said, Listen, I’d love to do a bonus episode with him. Can you put me in touch?

And then a literary agent I work with in the States called me. He’s like, You’ve got to put me in touch. That guy’s got a memoir. I put them in touch, and I called him back. He’s like, Oh, he’s great. I’ve got some writers in mind, because, you know, he needs a co-writer, a ghost writer. I’ve never done that before, but I think I just got weirdly competitive. I was like, Well, I want to do that. So, he put me in the mix. I think there were five or four of us that were kind of auditioning for this. We had these Zoom calls with Scott and his wife. And then Scott just chose me. I think I was the only woman. And then, once he did, I thought, Oh, my God, how am I going to write like this guy? We are opposites in every way. I’m this lefty Canadian agnostic. I don’t even like cops. I write about cops—the bad things they do anyway. But we ended up doing this.

At first, I didn’t know what I was getting myself into. As a journalist, it’s a bit of a weird role, too, because normally, I would write about him, not with him or as him. But he is such a character. He is such a good storyteller. It was really the most amazing project, because he’s not a writer, but he tells stories in an incredible way. He remembers details, and I could fact-check those details with court records. And he was often, you know, wired—so I had verbatim dialogue of neo-Nazis and bikers and the KKK and everything. It had this sort of tragic comedy to it, this dark humour.

He’s got all these hilarious sayings. At one point, when he was being strip-searched by the bikers, they almost found his wire. And he has this thing that he said—“it was like his asshole was knitting a sweater.” He just has all these things I would never say. I would listen to him as kind of method acting but for writers.

Were there ground rules set? Because, like you said, that’s a very different thing from reporting on Scott to just bringing his opinions, his thoughts, his voice out. Did you have to establish rules in terms of how this process worked?

I did. Because ultimately, it’s his book, right? It’s his story. But there were a few things off the bat. I said I’m kind of distrustful of cops, and a lot of my career has been highlighting the abuses. But all his cases had ended in convictions. Everybody pled out. I knew that there were no cases of entrapment, and he had solid cases.

We were talking earlier about PTSD. He had a real crash. He had to be taken off a case for a bit, and I really probably pushed him a little bit on this, although he was very open. But I thought it was really important for the book to show that really dark period where he had mental and marital stress. And I think that was hard for him, going back into that. That was hard on their marriage, returning to those days. But, yeah, you didn’t want it to be just total hero worship.

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And, like you said, the book overall could be read as, Isn’t the FBI great? Look at all the great things the FBI and cops in general do. And I could see you having some moments of, like, Do we need to add some context here?

Of course. I mean, after 9/11, I can’t tell you how many cases I reported on—on entrapment, and FBI misdeeds, on cases of kids joining al-Qaeda, and it was just absolute entrapment or abuse and places like Guantánamo. I did struggle with that. We tried to balance that out. But you cannot deny he had a remarkable career, and at a larger level, it was really fun working with him because we were so incredibly different. And in today’s world, where we’re all in our little silos and echo chambers, I don’t hang out with Republicans; I don’t hang out with bikers or cops or southerners or Baptists or all the boxes he checks that I don’t. And so, we didn’t talk about politics. The book was apolitical, and that was kind of important for me.

He lives in his echo chamber; I live in mine. We’re both pretty set, but we could have actual conversations. We could debate. I could say something. He could take it. He could say something. I could think about it. It was just like what I think, as a society, we need to do more of: stop yelling at each other. And we got along so well. I mean, we’re such good friends now and had so much fun doing this.

I’m one of those annoying writers that loves writing and loves doing books, and I’ve had three really good experiences, so I’m lucky. But yeah, I was definitely not sure where this one would go. It felt a bit risky at first, and it worked so great.

Is there a project in the works, or is there something where you’re like, I’ve got to invest my time in this?

I am very lucky that I can cross mediums, that I am able to do books and podcasts and films. I do have a documentary that we’re working on now about a prison newspaper for the CBC that I’m really excited about. A podcast on the crazy Ryan Wedding story I’m working on. A piece for The Walrus on Sudan.

I can easily see someone like you going, Well, I can work on this project for a couple of months and have it be really intense, and then it gets released, and I have thousands of people immediately responding to it, engaging with it. Or I can focus on a book for three or four years. It comes out three or four years after that. The book industry can be unforgiving. It can be a thing where you’re just throwing out a book into the void.

It is probably the most satisfying. I mean, I’m very extroverted, but I also love to work by myself, writing. Most of my other projects are with teams, which I also love. But I hope I have another non-fiction idea that comes up soon.

I have also been plugging away on a novel. And when I first left the Star, I was lucky enough to get a Canadian grant. I did have a few months to really get in. Unfortunately, it just is on the back burner with the other paying projects. But I really hope to get back to that.

Omar El Akkad is kind of my hero in that sense. We reported together in Guantánamo, and he covered the Arab Spring, and we did other projects that were along the same lines when he was at the Globe. And when I read his books, like American War, I’m like, Oh, you’re getting that from Guantánamo, and Oh, that comes from your coverage in Egypt. I love what he’s doing. I’m so proud of him; he’s such a voice these days. And I think that interests me, because as you say, you can throw these books into the void, and I do like the idea of bringing truths to people in fiction.

The novel I’m working on—I won’t even talk about it yet, because it’ll probably never get there—it’s something that I feel strongly about in my reporting. And I think if I can dramatize it and get it out there, it might get a few more eyeballs than some of the non-fiction books.

Adapted from the podcast What Happened Next, produced and hosted by Nathan Whitlock in partnership with The Walrus. Listen to the full conversation here.