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Conan O’Brien Needs A Friend

The Freedom Reader

09 Apr 2026

Transcription

Chapter 1: What is the main topic discussed in this episode?

3.524 - 12.398 Conan O'Brien

Conan O'Brien needs a fan. Want to talk to Conan? Visit teamcoco.com slash call Conan. Okay, let's get started.

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13.44 - 21.252 Reginald

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.

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21.332 - 33.928 Conan O'Brien

Yeah. I have been reading your bio, your story, your Marvel origin story, Reginald, and it's fascinating. It's amazing.

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34.429 - 42.679 Reginald

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.

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42.739 - 43.44 Conan O'Brien

I'm sorry, Reginald.

Chapter 2: What led Reginald to a life of enrichment and education?

44.381 - 70.318 Conan O'Brien

Reginald, 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 those are incredibly impressive accomplishments.

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70.298 - 94.838 Reginald

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 crazy volatile violent thing i've ever done in my life yep and um

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95.223 - 113.841 Reginald

And nobody tells you that you could do something at 16 that'll 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 debt 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.

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113.881 - 119.607 Reginald

So that's the kind of devastating thing about it is recognizing that I changed my life forever.

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120.448 - 142.938 Conan O'Brien

Well, there's so much to... like to say unpack here. There's so much to talk about. 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?

144.36 - 160.769 Reginald

Yeah, I did. I did two years off and on in solitary. But the thing that's really remarkable is I'm 18 years 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.

163.032 - 167.979 Conan O'Brien

I'm going to say, that's some impressive artwork around you.

167.999 - 185.271 Reginald

And I was unraveling. And I heard a guy call out for a book. And I realized that these dudes had created an underground library for themselves. And all you had to do was 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

185.875 - 209.67 Reginald

Robert Hayden, Lucille Clifton, Sonia Sanchez, Langston Hughes, Sterling Brown, Etheridge Knight. And I'm reading these words, and I realized that these poets were able to capture an entire life in 14 lines. 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 Soprano Sky, and it was Sun Tzu's The Art of War.

Chapter 3: How did Reginald's past mistake shape his future?

238.45 - 261.698 Reginald

And so it was Sonia Sanchez's Undisciplined on Sky 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.

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262.403 - 272.958 Conan O'Brien

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?

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275.782 - 296.558 Reginald

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 the Evelyn Woods, but you wouldn't believe what book it was. It was the Evelyn Woods Guide to Speed Reading. See, I've always been obsessed with infomercials, right?

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296.838 - 312.94 Reginald

And they would have those infomercials on how to speed read. 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. I said, no, he's reading. Listen to this.

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313.561 - 334.665 Reginald

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. 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. Yeah.

334.645 - 358.035 Reginald

She would be like, Walter Moses' new book just came out. Book came out three years ago. And so what prison did was like, honestly, the judge said to me, I'm under no illusion that sending you to prison will help. But you can get something out of it if you try to. And I never forgot what he told me. And I just had to lean into what I cared about.

358.055 - 379.637 Reginald

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 will be a writer because the only thing that I can name myself as loving in 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.

380.039 - 409.068 Conan O'Brien

That's a, I mean, 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.

409.348 - 424.17 Conan O'Brien

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.

Chapter 4: What role did solitary confinement play in Reginald's transformation?

530.21 - 561.198 Conan O'Brien

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 opened by books.

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562.079 - 582.817 Conan O'Brien

That's a massive thing 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, you've, this is a massive contribution you've made. I cannot tell you how impressed I am by what you've done.

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582.837 - 610.621 Reginald

I appreciate that. And I, you know, I, we have seven, eight people to work for us out of our team of 22 serve time in prison anywhere from 18 months to 30 years. And, 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, um, Remember I got a bald head, but you remember, I'm not just a client. I'm not just a president.

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Chapter 5: How did Reginald discover the power of books in prison?

610.761 - 612.062 Reginald

I'm a client, you know?

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612.202 - 627.638 Conan O'Brien

Oh, yeah, yeah, yeah. The hair club for men. Cy Sperling. Cy Sperling would end his commercials. It was a spray, I think, that you could put on your bald spot. 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.

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628.018 - 648.139 Reginald

Yeah. This is like, I feel like I just, I 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 us safe when we chose to pick up pistols. Books were the talisman that would have kept us safe instead of the pistols that caused more harm.

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649.786 - 668.571 Conan O'Brien

Did you know when you were getting out of, did you have a plan when your sentence is coming to an end? Did you have a clear goal then, I am going to get this higher education? Or was it something that unfolded gradually after you got out?

670.036 - 691.892 Reginald

Now, 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.

692.648 - 713.621 Reginald

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, Dwayne, you're a lawyer.

713.641 - 733.7 Reginald

Can you can you help with my case? I started Freedom Reads 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.

734.321 - 758.602 Reginald

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, you know, from 2006 until now. And now I run an organization with a multimillion dollar budget, 20 people that work under me.

Chapter 6: How does Freedom Reads impact incarcerated individuals?

1581.809 - 1606.511 Matt Gourley

Executive produced by Adam Sachs, Jeff Ross, and Nick Liao. Incidental music by Jimmy Vivino. Take it away, Jimmy. Supervising Producer, Aaron Blair. Associate Talent Producer, Jennifer Samples. Associate Producers, Sean Doherty and Lisa Byrne. Engineering by Eduardo Perez. Get three free months of SiriusXM when you sign up at SiriusXM.com slash Conan.

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1606.832 - 1612.423 Matt Gourley

Please rate, review, and subscribe to Conan O'Brien Needs a Fan wherever fine podcasts are downloaded.

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