S03E138 American Injustice at Guantánamo Bay with Joshua Colangelo-Bryan

A prison designed to sit “beyond the law” still shapes how power understands accountability, and how advocates fight back. We sit down with Joshua Colangelo-Bryan, special counsel at Human Rights First and veteran of impact litigation around Guantánamo, to unpack a two-decade journey that blends courtroom battles, diplomacy, and storytelling into what he calls empathetic strategic lawyering. The result is a rare, unvarnished look at why trials have stalled, how detainees went home through political channels, and what it takes to stand up to governments when process becomes the battlefield.

Joshua traces the early habeas wins that opened access to clients, then explains why a bespoke military commission system broke under its own flaws. He offers a ground-level view of serving as a lifeline to people held incommunicado for years and shows how empathy sharpened strategy: engage allies, inform the public, and negotiate transfers when courts move too slowly. We dig into CIA black sites, the jurisdiction fight that reached the Supreme Court, and the quiet truth that the higher the stakes, the longer the slog, especially when states hide behind immunity and national security.

The conversation doesn’t stop at history. We confront the present: a shrunken detainee population, stalled 9/11 cases, and a troubling new twist, migrants briefly routed through Guantánamo as costly political theater. Joshua connects these choices to a broader erosion of U.S. credibility; when Washington bends international law, authoritarian regimes point and follow. Still, there is light: lower federal courts continue to enforce baseline standards, and the public can see through spectacle when the human harm is clear.

Reach Joshua here:
https://www.linkedin.com/in/joshcolangelo
https://www.instagram.com/joshua_colangelo/
https://humanitasmedia.org/
https://www.instagram.com/humanitas_media/
Book mentioned: https://amzn.to/3NhWgv2/

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Transcript

Welcome And Guest Introduction

SPEAKER_00 0:24

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SPEAKER_01 1:12

Welcome to another episode of the Leadership in Law Podcast. I'm your host, Marilyn Jenkins. Please join me in welcoming my guest, Joshua Coangelo Bryan, to the show today. Joshua is a special counsel at Human Rights First and the leading voice in impact litigation and international human rights advocacy. For more than two decades, Joshua has worked at the intersection of law, democracy, and human dignity, representing Guantanamo detainees, conducting human rights investigations in conflict zones like Yemen and Syria, and holding governments accountable through landmark litigation. In his career, he served with the United Nations mission in Kosovo, working on the prosecution of war crimes. He has testified before Congress, written for major publications, including the Washington Post and The Guardian, and spoken widely about Guantanamo in international law. He's also the author of Through the Gates of Hell, a powerful account of American injustice at Guantanamo Bay in the practice of what he calls empathetic strategic lawyering. Today we're exploring that work and the reality of Guantanamo in 2026 and what justice looks like when the law operates under extreme conditions. I'm excited to have you here, Joshua. Welcome.

SPEAKER_02 2:20

Thank you so much. It's great to be with you.

SPEAKER_01 2:23

Awesome. Very impressive bio. Tell us a little bit about your leadership journey and what brought you here.

SPEAKER_02 2:29

I spent many years at a fairly large commercial law firm, but created a niche for myself that let me do a very substantial amount of work on pro bono matters. Through that, I got to do uh cases and non-litigated matters relating to a range of civil rights and human rights issues. And I always tried to bring along kindred spirits at the firm to join me in those efforts. I think many people find commercial litigation a reasonably satisfying thing, but when they have an opportunity to work on something that has a very deep and personal meaning, they jump at it. After many years of doing that, about 12 months ago, I joined Human Rights First to focus entirely on public interest matters, working with young lawyers in a variety of contexts to bring them into this kind of work as well.

SPEAKER_01 3:41

Wow, very interesting. So you spent over two decades working on Guantanamo cases. What first drew you, like what you want to do something you're passionate about? What first drew you into this work and what kept you engaged in it for so long?

Why Guantanamo Became The Fight

SPEAKER_02 3:54

So it started before many large firms had gotten involved in those cases. And so to the credit of the firm I was with then, they agreed. Our basic motivation was really based on a matter of principle. The government was saying it could grab anyone anywhere in the world, thousands of miles from a battlefield, on a battlefield, call the person an enemy combatant, bring them to Guantanamo, and hold them literally forever without charge, trial, hearing, any other process. Beyond that, the government's position was the people who were held there did not even have an enforceable right to be treated humanely. So to us as lawyers, that really sounded like the absence of law and a position just far outside of mainstream American jurisprudence. So it was really just the idea of defending the principle that if the government wants to hold you potentially for the rest of your life, you're entitled to some manner of process. That's what drew us in to begin with. Once we started to get to know our clients and examine the accusations against them, it became a much more personal matter and one in which we began to see that there was just real injustice going on.

Guantanamo’s Present Reality And Failures

SPEAKER_01 5:29

I see. And so a lot of people I think that Guantanamo is a closed chapter, right? What does the day-to-day reality look at now, right now?

Migrants Sent To Guantanamo As Theater

SPEAKER_02 5:41

There were there are two iterations of this. One that existed for a number of years before the Trump administration's second term, and then another iteration that began with the Trump administration's second term. And with respect to the post-9-11 law of war detainees, Guantanamo ended up having a very small number of people. Today that group is 15. That includes people who have been charged with crimes relating to serious acts of terrorism, including 9-11, but whose trials have not even begun all this time later, because the Bush administration essentially invented a justice system to be used at Guantanamo only that had so many flaws that procedural issues have dogged it ever since. While I think all reasonable people recognized that the Guantanamo operation, which once held almost 800 people and had been whittled down to 15, was really a strategic along with legal failure. That fact is what made it appealing to the Trump administration to start sending people from the United States to Guantanamo. More specifically, what I mean is that since last spring, the administration in a very haphazard way has sent 700 plus migrants from the U.S. to Guantanamo. By haphazard, there are instances in which the administration sent people to Guantanamo and then shortly thereafter brought them back to the U.S. Or other instances in which it sent people to Guantanamo for brief stays before sending them to El Salvador, for example. It's a massively costly thing to do, given that we're talking about a base in the middle of Cuba, a country we obviously don't have diplomatic relations with. And what possible strategic benefit from a national security perspective could there be from sending a group of people from the US there for 72 hours and then bringing them back? It really is just political theater so that the administration would say, here's another really tough, cruel thing it's doing to immigrants.

SPEAKER_01 8:20

It's the story. Yeah, it's the distraction. Yeah, exactly. In your book, The Through the Gates of Hell, you described practicing empathetic strategic lawyering. How did that approach take shape in such an extreme environment?

Empathetic Strategic Lawyering Defined

SPEAKER_02 8:36

We went to Guantanamo for the first time shortly after the Supreme Court had ruled that federal courts had jurisdiction over claims by detainees, refuting a government argument that if you put a foreigner in Guantanamo outside U.S. sovereign territory, no court had jurisdiction. Despite the significance of that ruling, it became clear quickly that we were going to be fighting with the government over other initial non-merit issues in the litigation for a very long time. And so even though the idea of habeas corpus and we had filed habeas petitions, is that in one form or another, you get a fair hearing, it became obvious that was not going to happen for years, if at all. And so while we continued to litigate the case, we also understood that we needed to have some alternative strategies. We saw very quickly that people from Western European countries, even if they'd been accused of serious acts, were being transferred back to those countries through diplomatic political deals. So if you were a UK citizen, presumably Tony Blair got in touch with the Bush administration and said, I'm getting killed politically, having our people at Guantanamo, I need them back. Lo and behold, they all went back. Our clients were from Bahrain and Saudi, which obviously aren't Western European countries, but they are, have been critical allies of the U.S. So we said, why can't this happen for our clients who, in fact, are not accused even of taking action against the U.S. And so while we were all litigators, we started what you could call a public relations and diplomacy campaign to get the stories of our clients out to the public and to explain to people in the Middle East that we weren't going to get hearings for our clients anytime soon. They were all in pretty desperate straits. And if their countries wanted them to come home in one piece, you know, those countries were going to have to use their relationships with the U.S. And little by little, our clients went home through those deals. So that was the a way of approaching the case strategically that's outside the normal paths that you take as a litigator. In terms of the more empathic personal side, our clients were held incommunicado, like everyone else at Guantanamo, except for their visits with us. So we served as their only connection with the outside world.

SPEAKER_01 11:43

For years.

Diplomacy And Public Advocacy Tactics

SPEAKER_02 11:45

For years. None of that was going on at Guantanamo. So we really were the lifeline. And in particular, there was one client with whom I developed a very close relationship, but not an absolute friendship, which is really the centerpiece of the book. And I don't think you could be an effective lawyer in that context without being able to develop some relationships with people who otherwise were utterly starved for that kind of contact. So the client Jobber who who I describe in the book, Our Relationship, he would often talk about how he would get this glimmer of hope when I came down to the base to see him, and he would fight to keep that alive until my next visit, which isn't because I'm some amazing person to sit down and talk with, but I was the only human being from other than guards and other staff who he didn't trust who had any kind of interaction with him. So it was a very unusual and probably close to unique in the literal sense of the word situation to be doing lawyering in.

SPEAKER_01 13:20

That is very interesting. Guantanamo is Guantanamo the only place that in an American basis or whatever that works outside these legal norms.

Being A Lifeline To Clients

SPEAKER_02 13:30

There were CIA black sites as they were referred to. People were held and subjected to things like waterboarding that we pretended weren't torture, even though if someone did that to a U.S. soldier, we would call it torture in a in a flat second. People were actually brought from those black sites to Guantanamo at one point when the administration was trying to get a law passed to throw all of our cases out of court, and it wanted to be able to say, hey, there are some really dangerous guys at Guantanamo. So they brought people who it's commonly thought did have some connection, at least in certain instances, to things like 9-11, to Guantanamo to point to them, given that the hundreds of people they already had at the base, by and large, were not even accused of taking any kind of hostile action. Guantanamo ultimately does have its own sort of unique status as being the place where now, over decades, we have held people who we say are entitled to a very limited set of rights, if any at all, because they're outside the US US jurisdiction.

SPEAKER_01 14:54

Okay, so not being a military veteran, aren't bases considered U.S. soil?

SPEAKER_02 15:00

There was a very robust argument back when the government decided to try this theory, and it said, hey, it's Cuba. Now that's not America. That's not our sovereign territory. We just we lease that land.

SPEAKER_01 15:19

But if you're born on a base in Panama or Germany or Japan, you are an American citizen.

Black Sites And A Prison Beyond Law

SPEAKER_02 15:25

And ultimately, what the Supreme Court concluded was sovereignty itself isn't quite the issue. The U.S. has complete control over that base. The U.S.'s position is that it can remain in that base in perpetuity. The argument that it's outside our literal sovereignty really isn't what determines whether people are able to bring claims. So that very formalistic position was rejected. But the whole reason that Guantanamo was picked to begin with was the idea that we would be capturing lots of bad guys in the war on terror. We needed a place to detain them securely, and we needed a place where we could interrogate them in a way that was beyond the law. And so the whole concept of a prison beyond the law was very fundamental, entirely fundamental, to the selection of Guantanamo.

SPEAKER_01 16:34

So it's basically a public black site.

Jurisdiction Fights And Supreme Court

SPEAKER_02 16:37

Yeah. Yeah. Certainly, the once lawyers were able to go down after litigating that Supreme Court case, that changed the nature of it because finally information about people who were held there could be disclosed and shared. So it had absolutely been a closed loop system until that point. But once we started going down, and once we got the court to require the government to try to explain why each person was being held, that's when we could figure out who was there and see that there were hundreds of people who not even the government actually claimed was engaged in some kind of combat against the U.S. And that's what happens when you just detain a group based on identity, like our Muslim men, and you apply no process. Process is how you figure out who's a bad guy and who's not a bad guy. It's not just a nice academic concept. It's really the only way that we human beings have determined, have figured out for determining who's dangerous and who isn't. And the civilian leadership at the Pentagon and in the administration basically told the military, you are not to engage in any kind of fact-finding. Those people are all going to Guantanamo. And that was the situation for several years until we started going down.

SPEAKER_01 18:14

Wow, that's amazing. So you've worked with power for challenge powerful actors and governments and stuff. So what does it take to bring cases like these forward when the odds just seem to be stacked against you?

SPEAKER_02 18:26

I think that you need to clearly and soberly think through the potential paths you have to achieving what you hope to achieve. And sometimes there will be a very narrow legal path to avoid jurisdictional or immunity or other non-merits defenses, just as a pure matter of litigation. You also need to think about how advocacy might take place outside the courtroom that would shine light on particular practice that you're trying to stop. And I think you want to just constantly be questioning your own analysis in the sense of not coming to any easy, quick conclusions, but continually revisiting the approach and trying to probe for weak spots before you would be actually in a in an adversarial legal position from the people you're trying to stop.

SPEAKER_01 19:41

And again, you said some of these cases have taken years.

Litigating Against Powerful States

SPEAKER_02 19:45

Absolutely. We had a case. And these agents saw no reason not to bring their Turkish, their Turkey-based practices to Washington, DC. And it was all captured on video. There was a almost a unanimous congressional resolution condemning the attack. Everyone knew it happened. Before we could even get to the merits of the case, we litigated for years over Turkey's claim that it was just defending its president, which made no sense to anyone who watched 20 seconds of the video. But the legal process sometimes moves very slowly. And the higher the stakes, the slower it can actually be, which feels a little bit perverse when you're trying to pursue justice, but is uh just an inherent reality of how that often works. Yeah. You would never tell anyone, uh, this will be done quickly.

Endurance, Expectations, And Resources

SPEAKER_01 21:57

And how do you balance Yeah, pardon me? How do you balance your strategy with your human reality with these long-term cases?

SPEAKER_02 22:07

You you have to take whatever steps you think appropriate to make sure that clients are prepared for how long it will take and to try to line up your own resources in advance that can sustain you through that process in very practical terms as well as more personal terms. I think the understanding at the outset that there are very few quick victories is is probably. The key thing so that everyone's expectations are realistic and your planning can be realistic. Because if you're going after the rich and powerful, obviously they've got the resources, they've got all kinds of access to the corridors of power. Those are those are the biggest, those are the biggest fights, the biggest slogs. And you need to figure that, put that into your calculus from the very beginning.

SPEAKER_01 23:12

Understand. Wow. So how do you see you've worked with some big powers in the Middle East and that sort of thing? How do those global experiences help you inform your view of the U.S. actions in Guantanamo?

Global Norms And U.S. Credibility

SPEAKER_02 23:27

It was it was interesting to see various countries that are universally known as human rights abusing governments point to what the US was doing at Guantanamo to say, wait, we know that the US is the global purveyor of justice. If the US is doing these things, then surely they must be acceptable. And that unfortunately is a dynamic that has only gotten worse. And when I say only gotten worse, I'm thinking of our sojourn into Venezuela to grab a person who Lord knows you wouldn't want him running your country, but in a way that no reasonable person believes was legal. The U.S., obviously, even at periods during its periods when it respected human rights the most was not flawless in any respect. But when the US openly violates you international law and international norms, that only helps bad actors around the world justify what they're doing as well.

SPEAKER_01 24:58

Yeah, like a little kid says, you started it.

What Gives Hope In The Courts

SPEAKER_02 25:02

Oh, waterboarding is not illegal? Attacking a country that is not a threat to you, that's not illegal. Oh, okay. Then we'll play by those rules too.

SPEAKER_01 25:14

Yeah, it opens a lot of doors. That's true. Um, let's see. So looking ahead, what changes do you think political, legal, or cultural give you the most hope that we can find finally move closer to justice?

Closing, Book, And How To Connect

SPEAKER_02 25:29

So far, it does seem that even at this moment in U.S. history, our court system, particularly at the lower levels, is functioning, even in the face of very unusual conduct and very unusual litigation practices by the U.S. administration. That is one of the things that I try to hold on to when otherwise it feels like the justice system that I thought I based my career on being a part of is at risk. And it's been very good to see that some standards we all thought were accepted are still being required by judges, particularly at the district court level. And I suppose I otherwise hope that people who maybe are not paying as much attention as they might start to look at various practices of the current administration to see the human harm that's being caused and the way in which the administration is undertaking activities that have no legitimate benefit, whether it's from a national security perspective or otherwise. The amount of money we have spent mobilizing law enforcement to conduct raids against people who are not criminals in any sense, and it's preposterous from a safety, from a national security perspective. So I hope that becomes increasingly clear to to people, even if those people perhaps aren't used to thinking about things in terms of rule of law or human rights, just looking at the human consequences and the fact that we are doing so much of this stuff just as theater. Sending armored cars into lower Manhattan to arrest guys who are selling counterfeit Yankee hats. I guess that protects the Yankees' intellectual property. Certainly doesn't make any New Yorker feel safer because no New Yorker has ever felt their safety was being threatened through the sale of a bootleg Yankee hat. And that that's just one tiny example.

SPEAKER_01 28:01

Thank you so much. This has been a great show, Joshua. It's been so interesting. I know my listeners may want to connect with you. Obviously, get your book. Where would it be the best place for them to connect with you?

SPEAKER_02 28:12

The Human Rights First website has lots of information about the work that we do as an organization. I'm not very good at social media. LinkedIn and Instagram are places that I try to put some updates on in terms of what we're doing. And the book can be ordered through Orange and Noble, Amazon, and a number of other options. Probably the easiest way to see all those options is if you go to the Simon and Schuster website and plug in through the gates of hell. I do what just want to emphasize to people that it's a book about Guantanamo. There are a lot of national security and legal issues, but at the core, it's really a relationship story about two people who became friends under very unlikely circumstances.

SPEAKER_01 29:10

And it sounds like you do just amazing work. I really appreciate your time today. Thank you for being on the show.

SPEAKER_02 29:15

Oh, thanks very much for having me. Great to talk to you.

SPEAKER_01 29:18

Thanks for joining me today for this episode. As we wrap up, I'd love for you to do two things. First, subscribe to this podcast so you don't miss an episode. And if you find value here, I'd love it if you would rate it and review it. That really does make a difference in helping other people to discover this podcast. Second, you can connect with me on LinkedIn to keep up with what I'm currently learning and thinking about. And if you're ready to take the next step with a digital strategist to help you grow your law firm, I'd be honored to help you. Just go to LawmarketingZone.com to book a call with me. Stay tuned for our next episode next week. Until then, as always, thanks for listening to Leadership in Law Podcast, and be sure to subscribe wherever you listen to podcasts so you don't miss the next episode.

SPEAKER_00 30:04

Thanks for joining us on another episode of the Leadership in Law Podcast. Remember, you're not alone on this journey. There's a whole community of law firm owners out there facing similar challenges and striving for the same success. Head over to our website at LawMarketingZone.com. Don't forget to subscribe and leave us to review on your favorite podcast platform. Until next time, keep leading with vision and keep growing your firm.