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

Michelle Shephard has written from Guantánamo, Somalia, and Sudan. How does she cope with the violence she uncovers?

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.

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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........

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