Conan O’Brien Needs A Friend - The Freedom Reader

Episode Date: April 9, 2026

Conan talks to Reginald from New Haven Connecticut about a past mistake that led him to a life of enrichment, education, and eventually the founding of FreedomReads.org, a non-profit that transforms the experience of incarceration by opening libraries in cellblocks.   You can support Freedom Reads here.   Wanna get a chance to talk to Conan? Submit here: teamcoco.com/apply Get access to all the podcasts you love, music channels and radio shows with the SiriusXM App! Get 3 months free using this show link: https://siriusxm.com/conan. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Conan O'Brien needs a fan. Want to talk to Conan? Visit teamco.com slash call Conan. Okay, let's get started. Hey, Reginald, welcome to Conan O'Brien Needs a fan. Hey, how's it going? Hey, Reginald, how are you?

I'm delightful, man. I'm doing great, honestly, yeah. I have been reading your bio, your story, your Marvel origin story, Reginald, and it's fascinating. It's amazing. Thank you. It doesn't rival yours.

I mean, yours is amazing. Mine is just, I'm just trying to make it out of it. No, yours is better. Yeah, honestly. I'm sorry, Reginald, I love to, I love to toot my own horn, but no, you have me beat by a country mile. You just have an amazing story. You have a law degree from Yale Law School, which is insanely impressive. and you have an MFA in poetry.

And here's what's, those are incredibly impressive accomplishments. And then you add to it that when you were 16, you participated in a carjacking and went to prison for eight and a half years. Yeah, that was not as impressive. I think that was the bane of my existence. But I think you live and learn. And for me, you know, picking up a gun was the most. most crazy, volatile, violent thing I've ever done in my life.

Yep. And nobody tells you that you could do something that's 16 that will change your life forever. You know, as many teachers that used to sell me, you know, I would end up in jail or I could end up in dead because I lived in a bad neighborhood, so to speak. Right. I didn't really understand that I could change my life forever. And I did. I changed my life forever.

So that's the kind of devastating thing about it is recognizing that I changed my life forever. Well, there's so much to, people like to say unpack here, there's so much to talk about you, as far as I know, you spent a lot of time in solitary when you were in prison. And while you're in solitary, you discovered books. Is that correct? Yeah, I did. I did two years off and on a solitary,

but the thing that's really remarkable is I'm 18. old, 17 years old, I'm in a hole, and they took all of your books from me. And the thing is, 24 hours in a cell with just four walls, not as beautifully decorated as the walls around me. I'm going to say, yeah. That's some impressive artwork around you. And I was unraveling, and I heard a guy call out for a book, and I realized that these dudes that created an underground library for themselves. And all you had to do is call out for a book, and they would sing you one. And so I said, hey, yo, send me a book. And they sent me this anthology called The Black Poets.

And that introduced me to Robert Hayden, Lucille Clifton, Sonia Sanchez, Langston Hughes, Sterling Brown, Etheridge Knight. And I'm reading these words, and I realize that these poets were able to capture an entire life in 14 lines. Yeah. And I remember buying two books. This is the first books I bought with my money. It was a Sonia Sanchez book called Under a Supremontas book. And it was Sun Tzu's The Art of War. Yeah.

Now, I was, I was trying to survive prison. I was 5'5 and 120 pounds. Oh, my God. Of those two books, I read Sonia Sanchez's book 100 times. And I never really, I never finished reading the Art of War. Yeah. Because I learned the real way to survive prison ended up being loved. It ended up being the exact antithesis of what had got most of us in prison.

Because I think the antithesis of love is violent. And so it was Sonia Sanchez's undisciplinarosky, that became a part of the pathway of me learning to love myself, but also in learning to love myself, me learning to understand that we had did horrendous things to land ourselves in prison, but that we could be more than those things. And I've spent my entire life since then trying to prove that to be true. I'm curious. Had you been at all interested or intrigued,

by books or even the idea of getting around to books before you went to prison? You know, the last book that I read. So my local library said, Mr. Betts, we understand you're still in prison. But we need you to return this book that you checked out. And it was that Evelyn Woods, but you wouldn't believe what book it was. It was that Evelyn Woods got to speed read. See, I've always been obsessed with infomercials, right? And they were head on those infomercials on how to speed read.

Yeah. And I was just like, my mom wouldn't let me, but she didn't believe that this guy could read, you know, a thousand words a minute. When he was flipping the pages, my mom said, he's just flipping the pages. Yeah. I said, no, he's reading. Listen to this. And so I went to the library and I found that Evelyn Woods book and I checked it out. And I still remember the tips that was in it.

So I've always been fascinated with reading. I've always wanted to be a reader. that my mom refused to let anybody tell me that hardback books came out first so that she could keep giving me the old paperback books of like books I hadn't read yet as if they were new. She would be like, Walter Moses's new book just came out. Book came out three years ago, you know, but the pig guy just came out. And so what prison did was like, honestly, the judge said to me, I'm under no illusion that's sending you to prison will help.

But you can get something out of it if you try to. Right. And I never forgot what he told me. And I just had to lean in and what I cared about. And I asked myself, what will you be when you leave prison? I mean, you're 16 now. What are you going to train yourself to be while in here? And I told myself, I would be a writer because the only thing that I can name myself as loving.

And that way outside of my mom was books. And I needed to love something that I believe might save me. And so I decided to lean into the love of books. That's a, I mean, it's, It's kind of stunning to me that you wouldn't encourage people to read who are incarcerated. And, you know, supposedly the concept behind the penal system is for people to better themselves and reform and grow. And so I'm amazed that books are denied to people in solitary. And that's a new concept to me because I would think you want people.

to read. You want people to build their minds. And the fact that you had to kind of do it secretly is kind of surprising to me. Yeah, but that, you know, to the credit of the Department of Corrections around this country,

I think that they've improved and changed a lot. Yep. My biggest supporters are the Department of Corrections. Our first Freedom Library was in Angola. I won A and 1B, Angola in MCI, Norfolk, where Malcolm X did it at times. And you got to understand that there's work that we've done, open at 600 libraries across the country, prisons in 14, 15 states, about 50 different prisons.

That doesn't happen without the Department of Corrections and the senior leadership in the Department of Corrections and the line CEOs, all saying, we believe in books. We believe in leadership. And we believe, I mean, we bring 100-pound bookcases and put them in sales. blocks that have never had anything but plastic and metal and steel. We bring 500 brand new books into the lives of people who many of whom have never seen a brand new book, have never smelled a brand new book. I mean, you know, it's about work that I do, but, and with all due respect, it's like the most humbling, you know, all-inspiring thing I've been part of of, because to be a part of it is to literally watch how an invention that dates back hunters a year, that Gutenberg

printing press. Actually, it's due to the conduit for people to have access to the world. If we first imagine, a printing press would get them access to it. Yeah, yeah. It is cool. Well, I mean, it's beyond cool. I want to make sure I stress this. You get out of prison, you go to Yale Law School, and you have founded something called

Freedom Reeds. It's an organization that gives incarcerated people access to books. And you guys have, as you said, opened. somewhere around 500 libraries across about 45 prisons in 14 states. And this is going to have an enormous impact. I'm sure it already has. But I do think that exposing people to books and giving them the chance to better themselves and find actually the love. It's not like eating your spinach, the love of books and the possibilities open by books. That's a massive thing. And, that you've done. It's huge. I know you're a humble person, but it's incredible. You had this

great misfortune when you were 16 years old, and you've, you know, you've, it's just a massive contribution you've made. I cannot tell you how impressed I am by what you've done. I appreciate that. And I, you know, we have seven, eight people to work for us out of our team 22 served time in prison, anywhere from 18 months to 30 years. And for each of us, you know, books played a profound role in us reshaping our lives. And so I love the fact that I feel like it's, remember, I got a ball ahead, but you remember, I'm not just a client, I'm not just a president. I'm a client, you know.

Oh, yeah, yeah, yeah. The hair club for men. Cy Spirling. Sy Spirling would end his commercials. It was a spray, I think. think that you could put on your bald spot and he would say, I'm not just a satisfied, you know, I'm not just the president. I'm a client. And then he would reveal. Yeah. This is like, I feel like I just want to carry books around with me everywhere to be like, I just don't talk about this.

I got a book in my bag, you know. We tell people that we keep books because books are the talisman that would have kept their safe when we chose to pick up pistols. Yeah. Books were the talisman that would have kept us safe instead of the pistols that caused more harm. Yeah. The, um, did you know when you were getting out of, did you have a plan when your sentences coming to an end? Did you have a, a clear goal then I am going to get this higher education, uh, or was it something that unfolded gradually after you got out?

No, I mean, I was just talking to somebody a few minutes ago about ADHD. And one of the real blessings in my life is that I have horrible ADHD, which means, I've never had a plan in my life. And the reality is you go to prison at 16. If you're a person that operates on a plan, you might have a hard time. I have literally never had a plan. I've kind of just moved through this world with a hope and a desire to be better than I was when I committed that crime and a curiosity and an openness. And so, you know, I ended up in law school because I was struggling to get jobs that would support me. And I ended up representing friends of mine and I got five people out of prison that I did time with because once I went to law school,

they were like, well, Duane, you're a lawyer. Can you help with my case? I started Freedom Rees because a friend and a supporter who also works for the Mellon Foundation had asked me, what would I do for people in prison if money wasn't an issue? And I said, we put millions of people in prison. I will put a million books in prison. And she said, how? And I said one library at a time. And with that phrase, I started making up freedom reads. I started making up the organization that's had a profound change in my life. This is the first job that I've had since 2006 because I've essentially been a student and an independent writer and performer from 2006 until now. And now I've run an organization with a multimillion dollar budget, 20 people that work under me.

I mean, it's been amazing. but I would be lying to you if I pretended like this was a part of a plan. I think the only plan I had was trust. That's well said, yeah. I mean, but that's true of, that's true of a lot of people. I know it's true in my case. I can't say I had a plan. I just kind of followed my passion.

And it was always news to me. Like I didn't know where it was going to lead. I didn't know where I was going to go. I'm sure I took a lot of missteps along the way, but you, you know, I think that's a good message to get out there is that it's not people saying, okay, this is exactly what I'm going to do. And here are the steps. There's a jazz quality to it where you're just playing what you feel. And if you trust and you're leading with that kind of positive energy and you marry it to a work ethic, things happen. And you're proof of that.

It's amazing. Absolutely amazing. Thank you. You talk about the smell of new books. I've been kicked out of bookstores because I just go and smell them. Oh. Yeah. Yeah.

Like you open them and smell them? I open it and I... I open it and I... I open them by the bookshelf sniffing the books. No, I open them and I smell them. Okay. And I guess it's a perversion. Are people holding them?

if you don't buy the books, though. As long as if you buy a couple of the books, the people at the bookstore, they'd be delighted, you know, you just got to buy, you just got to buy two or three. You know, I'm going to tell you something, Reginald, I'm a, I'm a sniff and runner. Oh, no. I get a good, deep sniff,

and then I run, and I'm wearing a raincoat when I do it. The sniff and sprint. Yeah, yeah, sniff and sprint. Yeah, and there's my pictures up in a lot of bookstores. around the country. They'd be like, yo, who was in a section

with the books, with a readist digest from the early, you know, from the early 20th century. Oh, that's Conan's favorite section. Have you seen this man?

Hey, it's 100 degrees out and it says, sunny day, why are you wearing a raincoat? That's my business. Look, Reginald, I'm a creep and you knew that

when you contacted us. So this is on, this is all on you. But I also think that, you know, a lot of us have bad, make bad mistakes when we're around 16 years old. We don't have, I wouldn't have had access to any, you know, I wouldn't have known where to get a gun or but. So there's a, you know, I, there's a quality to some of it, which is like, yeah, mistakes. usually people make mistakes, bad mistakes when they're in those teenage years. That's when they do it. And then, you know, I'm very aware that I was incredibly fortunate to be in a situation where my bad impulses couldn't get much worse because I'm living in a very stable kind of environment. Do you know what I mean? And I wouldn't have known where to get a gun, frankly. And I used to ask people, how do I get a gun?

You know, I did. Why? My sons. Yeah. Because, you know, makes you cool. Somebody asks me once. And I say, yes, I had no idea. I'm going to disagree with you.

Me with a gun does not look cool. I don't think it would do that. No. I really don't. I look like a frightened old woman who found a gun. Just wondering where to return it. The crazy thing about it, though, is I deeply believe that. So, like, even as a kid, I really had no access to guns.

Yeah. I could pretend that I did, I didn't. And then this one day I did. But I think about my son's life and they have never seen a fight before. You know, and so some of it, I think about how radically different the life that I've been able to provide for my sons have been because they haven't seen the kind of violence that my childhood was steeped in. Even if I didn't grow up in the worst neighbor. I didn't grow up in worse than a little, but I got beat up more, I got beat up, you know, at least 15 times. How many fingers do we have? Fingers and toes I was, you know, I spent my childhood on the rope.

You know what I mean? They used to call me glass joke. That's a joke. See, Coney got me trying to be a comedian now because this is the first time that I've been around somebody truly funny. So where did you grow up? Where did you grow up? Right outside of D.C. in PG County, Maryland. Yeah, okay. So. Which we had the benefit of like the nation's capital and you could see everything. And my mom had a great government job. But it also had the poverty and in a sense of being a black belt. And I'm being like, when you're like, like right outside of the center of everything, but literally right outside of the center of it.

I was the first person, my family to go to college and the first person to graduate from prison. Yeah. And that's not supposed to be a potential reality of somebody growing up in the 80s and the 90s. That's not supposed to be the last scape of what it means to, you know,

being an American citizen. But it literally was my perspective. Yeah. What do you credit because there have been many people, obviously, that have been in your situation and not had this spectacular turnaround, who do you credit or what do you credit

this ability to turn this massive negative into a positive and to, as you sort of say, pursue love and understanding and acceptance? Where did that come from? I'm going to go in and credit my mom, and I'm going to credit my mom for two reasons. First, you know, on the front end, she forgave me. And I didn't, she didn't make me beat myself up. She just accepted that I was better than that. And she had to accept it on faith. You know, she had to really believe that I was better

than the crime that I committed. Yeah. And convey that to me in such a way that I could believe that I was better. And so I'll credit my mom. And then she put money behind her belief. I took it. I took the per legal course in prison, she paid for it. You know, I was buying those books in prison. She sent me the money for it. So I'll credit that. And I will also credit, you know, like, every time somebody was honest with me. The judge was honest with me. He told me, I'm under no illusion that sending you to prison will help. But you can't get something out of it. And it was a challenge as well as just being a statement that like you 16 and everybody else is going to tell you how little power you have, how small you are, how violent you.

prison is, I'm a tell you you could get something out of it if you want. And I think that I've always had this attitude once I went to prison and felt like I was, I have synced to rock bottom that I could be who I say I have. And I have just sort of committed myself and dedicated myself in a singular way to doing that. And then I also say the last thing is that because I spent so much time in prison, I was able to become an auto-Dedat. I was able to pursue and chase my interests. And I was able to learn a lot about things that I thought were completely unrelated until they became related. Yeah. Like, who would have known me maneuvering around the Department of Corrections and around COs and around wardens would be the skill set that I needed 20 years later

when I'm starting an organization that demands that I not look at CEOs and wardens as my enemies. Yeah. I had to choose in prison that they weren't my enemy. And that's why it's easy for me to do it now. I had to choose in prison that I had a story that needed to be bigger than me being a felon so that the CEOs had to have a story that was bigger than them being a CEO. And so it was all of these small things that I actually built a set of skills that, you know, people trusted me to deploy in a way that matters. But honestly, I'm just here for the ride. And I could say that I wouldn't have guessed any of this when I was 16.

I wouldn't even guessed that I would survive prison. Yeah. But I don't think I would trade anything for the journey. Well, Reginald, you're an incredibly inspiring person, a really impressive person, honored to get to talk to you, seriously. And you're doing something that's huge, really is huge. Very few people can say they've had this kind of impact that you're going to have on all these lives. And so I'm, you know, could not be happier to talk to you. And if you have a question for me, sometimes people call and they have a question.

You may not have a question for me, you know? I do. I got one. And I'll tell you, I wrote you myself like 2 o'clock in the morning, you know, when I was like, man, I would love to be on this show. And it is one of those things, though. It was like, yo, somebody will read this. And out of everything that I've done, I really jumped out of the window like that. But 2 o'clock in the morning, I sent that email out.

And the question I have now is, we all say, changed our lives, but we live different reading lives. I wonder what book changed your life or what book you really remember from your 20s. Wow. I remember there's this book. I think I've mentioned it before by a writer named Shara called The Killer Angels, and it's about the Civil War Battle of Gettysburg. And it's written, it's fiction.

I mean, it's written like fiction, historical fiction, but it's very beautifully written. And I read this book and I just became obsessed with it. And I had already been a fan of history, but I read this book and I've gone back and read it many times since. And it's just kind of a beautiful, very accurate account of not only what happened, but the kinds of personalities that were involved.

And it just brought what could have, been a really dry historical account to life. And I realize you can do that with anything. Do you know what I mean? Any story can be told in a very dry, boring way, or if you've got a really talented writer and storyteller, they can tell it in an amazing way. And that book was really powerful for me, really powerful. See? See, look, I'm going to tell you, you won't even believe this. This is such a great question. That's such a great answer. My son's birthday is the Gettysburg, is the date of the Gettysburg. It's the date of Gettysburg address. Oh, wow. That's my oldest son's birthday, November 19th.

Well, you know what I see? Get the killer angels. Get the killer angels. You're going to read it. It's just a great book. And if it was just fiction and wasn't about real, how the battle really unfolded, it's just filled with amazing characters. It's so well done. I think Shara died shortly after he wrote it. He died young. But it's just fantastic. It's going in the library. Yeah.

I'm putting it in a Freedom Library. For now on, it's going to be in the Freedom Library. This is a great new addition. Hey, let me ask you a question. How do people donate? Is there a way that people can donate to this cause? Yeah, they should go to the website. Freedom Rees, F-R-E-E-D-O-M-R-E-A-D-S.

Yep, okay. And they can donate right at the website. I think that, I mean, I know I'm going to want to make a donation, and I'm going to make David make a donation. Of course. With your credit card. With my credit card. But no, I love what you're doing. I love your message.

I love your energy, your positivity, your sweetness. I mean, you know, you're one of those people. I get despairing sometimes about all the stuff that's happening in the world. And then I meet someone like you. and I think we're going to be all right. So, but then I go back to drinking. And book sniffing. I'm leaving this interview right now.

You're ending it on book sniffing? I'm going to go. I'm going to end it so I can get to, there's a bookstore just down the street. I'm going to put on my, put on my bathrobe and go rushing in there. You're a book sniffing. My book sniffing robe, yeah. Hey, Reginal.

We must ask people, what, have you smelled lately? Well, I don't want to go into that. Let's just say it was about personal. It was about Churchill. That's all you need to know. Hey, Reginald, be well, keep doing what you're doing. I hope we get to meet in person someday because I'd be honored to shake your hand, really. I will be honored to meet your person.

Thank you so much. And everybody else, man. The whole team has been lovely from the first interview. Oh, cool. Sit down. It's been amazing. Well, I got to let them all go today, but... Getting some AI in here to replace them.

All right, take care, Reginald. Bye. Bye. Take care, guys. Conan O'Brien needs a fan. With Conan O'Brien, Sonam Obsessian, and Matt Goreley. Produced by me, Matt Goreley. Executive produced by Adam Sacks, Jeff Ross, and Nick Leow.

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