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Episode Transcript

My guest today, Reginald Dwayne Betts is the MacArthur “genius award” winner, founder of the nonprofit Freedom Reads, a poet, and a graduate of Yale Law School. He’s accomplished all that despite the fact that he spent more than eight years in prison from the age of 16 to 24.

BETTS: I wasn’t a model prisoner, but I do think that in a different system that was searching to cultivate the skills and the talents and the personalities and just the rehabilitation of people inside, I would’ve been a model prisoner because I would’ve had mentors around me.

Welcome to People I (Mostly) Admire, with Steve Levitt.

I’ve really been looking forward to talking to Reginald. Here’s someone who beat incredible odds to turn his life around. But not only that, after graduating from Yale Law School, he could have made enormous amounts of money. Instead, he’s dedicated his life to helping those who remain behind in prison.

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LEVITT: You started an organization called Freedom Reads back in 2020. Could you tell me what Freedom Reads is doing?

BETTS: Freedom Reads is an organization I started to build libraries in prisons. And what we’re doing is building a place for people to commune over books. We make bookcases that are handmade out of walnut, out of cherry, out of maple. The idea is that this disrupts the built environment that is a prison; one that’s really rooted in desperation and a sense of hopelessness. And one that has an absence of nature. We want to bring nature into the space to give you something to look at and to remind yourself that you still live in the world. But we also want to bring these books in and center them in a way that makes it a sort of locus of something else within the prison. And so far, we’ve built 172 Freedom Libraries across 34 prisons in 10 states.

LEVITT: That’s fantastic. What kind of books do you put in these libraries?

BETTS: That’s always the million dollar question. So, I wonder, what is one of your favorite books? And let’s say fiction.

LEVITT: So, I’m going to maybe embarrass myself, but I love the Harry Potter series.

BETTS: The Harry Potter series is not in the library. So, that was the first time I’ve struck out.

LEVITT: Okay. What about Zen and the Art of Motorcycle Maintenance?

BETTS: I know that book and it’s not in the library. So, now that’s one that we will look for to put in the library, because that’s a really good book.

LEVITT: Yeah. I haven’t read it since I was in my twenties, but when I read it in my twenties, it had a really big influence on the way I thought about things.

BETTS: Well, this is how we built the collection though. I would talk to somebody like you and you would tell me a book like that, and then we would go research it. Yesterday actually I was having lunch with somebody and he said “The Things They Carried.” And I was like, “Of course we have Tim O’Brien in the collection. Tim O’Brien is amazing.” It also has Dostoevsky. It has some Chekhov, but it has some Shakespeare. But we have S.A. Cosby. We have James McBride. I tell people the collection is like a river. You can’t step in the same place of a river twice, but it’s still the same river. And so sometimes books get moved out and moved back in. The collection really is meant to be a robust statement about some of the most profound books in the world. So, you have your One Hundred Years of Solitude, but you’ll also have somebody like Rion Scott, who’s an amazing short-story writer. And we had this collection of his called Insurrections in the catalog, and you may have never heard of that. And then you pick it up and you get transported to another world, and that might be right next to the Chester Himes, or right next to the Maltese Falcon, or right next to the other run of Stephen King books that we have in there.

LEVITT: So these are mostly not easy books. Many of the prisoners aren’t going to be that highly educated. Can they handle these books?

BETTS: Well you have to destabilize what you think about literature. Text itself is kind of frightening because you think that the book is this fixed object that you have to have a certain amount of knowledge to enter into the book with. But we tell stories all of the time. And so one of the things we do is we bring writers in to give readings and to give talks and people hear them reading from their works and they say, “Oh, I can read that in a book.” Or we create an opportunity for community, because what you’re really saying is difficult is: Somebody has to tell you what the story is about. Somebody has to make you interested and invested and engaged. We also work with people who turn a book into a solo show, and they abridge it. So, we got Black Boy, and that’s a 300-page book that’s fit into a 45-minute solo show. We brought somebody in to perform The Brief Wondrous life of Oscar Wao. We brought somebody in to perform The Latehomecomer. And so what happened is that these shows actually help destabilize the barriers towards reading. And you realize, “Oh, I understood that story. So it’s just some competencies I need to learn to dig into this.” And then people start digging into it. If you go to a university and you start struggling, well, the one thing that you have immediately around you is a community of people that’s doing the same thing that you’re doing. And you could identify where to get that help from, once you recognize you have a need. Well, how does that exist in prison? Not just for literacy, but the way that literacy and literature calms an environment? It doesn’t. We make it exist. So, yes, some people won’t be able to read the hardest books, but by presenting them in the way that we do, I think people end up constantly surprising themselves.

LEVITT: Do you have any way of knowing which books are being read and which books are having an impact? It’ll be great to have a feedback mechanism.

BETTS: Oh man, I hate to say this because — um, okay. I’m going to say it anyway. Forgive me, Jill Lepore. But, professor Jill Lepore, historian out of Harvard, we got her book in there about Wonder Woman and somebody in our team was talking about like, “Should we take this out of the collection? Maybe it doesn’t comport. We thought it was something different.” I’m like, “Ah, it’s pretty good. I like it. Let’s see what happens.” The next day we got a letter from a woman in prison — we had just did six libraries in a California women’s prison. And so the next day we literally got a letter from this woman saying, “I picked up that Secret History of Wonder Woman, and it is such an amazing book. I cannot believe I found something like this on this shelf.” But we create another feedback loop because when we do events — and the reason why we do events is simple. They have events at the public library all of the time. I did eight-and-a-half years in prison and I never saw anybody come to talk to us. Nobody ever came to read us poetry. Nobody ever came to share their work. Nobody ever came to say let’s do the same thing for you that we do for college students and high school students all around America, which is to expose them to people who might give them a reason to understand what they might become in this world. 

LEVITT: You’ve put a lot of thought into every detail of this it seems. Could you describe the bookcases in more detail? What do they look like and why were the choices around them made, and who makes them?

BETTS: I started doing some research on micro-libraries because that was the first word that popped in my head that described what I wanted to do. But a lot of these are designed architecturally to think about what the space does for the people, because you recognize the building as being what attracts people to build community. Well, we had to make the actual structure of where the book’s set be the thing that builds community, almost as if it’s operating as a building. So, we couldn’t put the bookcases on the wall because I wanted you to look at books and look at the person across from you. And so I reached out to some architects. And then former commissioner of the Connecticut Department of Corrections, Scott Semple, had a relationship with Mass Design and he introduced me to them. And then I ended up partnering closely with them to build the libraries. You know, first we were thinking about literally putting a whole building into a housing unit and what would that look like? And the D.O.C. immediately let us know that you can’t obscure sight lines. And the architects would say things like, “Well, what if we made the material diaphanous and see-through?” And the D.O.C. folks would say, “Again, you cannot obscure sight lines. Let me say this more clearly. You have 44 inches of height to work with.” And so we started to think, “Okay, if we have 44 inches of height to work with, well, what do we want to do with this? What do we want the people to do when this enters into a space?” And so we decided we really, really want people to not look at books in isolation. We wanted it to be a space where you could be there and not even looking at the books. You could be there just having a conversation about sports or anything. Like, it could be a locust point of calm in the housing unit.

You know, the idea of Freedom Library, this was coined by Elizabeth Alexander, the president of Mellon, but it exists in the tradition of Freedom Schools and Freedom Riders. So, we worked with this guy named Jeffrey, one of the architects at Mass Design. He was thinking about Dr. Martin Luther King Jr. and how he has this quote that says, “The arc of the universe is long but bends towards justice.” Well, what if we designed this in a modular way that created different kinds of arcs, and what if we realized that once we build 10,000 of these, once we move towards putting one of these on every housing unit in every prison in America, wouldn’t that just be a giant arc that’s bending towards justice? And so that’s how we thought about, okay, we’re going to make it curve. We’re going to make it modular so that if a prison doesn’t have a lot of space, there’s always at least two bookcases to create an arc and to create an opportunity for three to five to eight people to browse the books at the same time. So, we decided those things about the shape. And then we decided we wanted to use wood as a material because I did eight-and-a-half years in prison and never saw a tree. I was never able to touch a tree. So, that was also the physicality that we wanted to push. There’s one prison called Valley State Prison in California. They have 16 housing units and we were taking 50 bookcases — three and a half per housing unit — and then you got to unbox the 500 books and put them on the shelves. It took about six hours and what it meant was that the people that came with us, they were doing community service. They were talking to the people inside. And for a lot of folks inside, for the first time in their lives, people from the outside came in who wasn’t their family, who wasn’t there to ask them questions about their crimes, who weren’t even there to talk about criminal justice reform. They were there to provide them with this opportunity and provide them with conversation.

A woman once said, “Man, what is this Shakespeare?” And another woman said, “Oh, it’s a tragedy.” And the other woman said, “Well, what’s a tragedy?” And she was like, “It means everybody dies.” And I’m like, “That’s not all it means. I mean, look, what about this line in Hamlet?” And we were holding up Hamlet when he said, blah, blah, blah. She was like, “Yeah, that’s kind of interesting.” We had this short conversation. But it was funny — it showed both of our knowledge of Shakespeare, it was a little bit of give and take, and we got to model the relationships that get built around literature. And so I like to think that the actual design elements, down to the finger joints that we use to connect the pieces of wood, down to the fact that — you asked, “Who makes them?” We have a team of people that were formerly incarcerated that’s doing the work with us. And then out of the 12 full-time employees that Freedom Reads has, five of us have served significant time in prison. You know, when we go back into Angola and James is with us and he’s seeing his friends who he grew up with, who he did 10, 15, 20 years with, it’s just a really powerful moment because they’re like, “What are you back here for?” And he’s like, “I’m bringing these libraries.” It’s almost like we are creating a ecosystem in which all of the work around the Freedom Library is internally connected and externally connected, from me as the leader of the organization, to the team members that we’ve brought on, to the relationships that we built to do the work. And our primary partner — because every time we build a Freedom Library for a housing unit, we also build one in the prison for staff. And so our primary partners are the people in prison, both those incarcerated and those who work in prison.

LEVITT: I’m surprised to hear you do it for the staff. What was the thought process behind that?

BETTS: Some of my worst experiences in prison were at the hands of C.O.s. But some of the most transformative experiences I had were also through interactions with staff. I remember getting a job at the law library. It was only because the staff okayed me to work there. And I was like 22, 23; and young folks in prison sometimes break rules. And when you get access to a printer, they think that you might be doing something illicit. And sometimes we are. So they defer to hiring older, more mature people to avoid a potential conflict. But I don’t think I would be a lawyer today if he didn’t make that decision to give me a chance. And he only made the decision to give me a chance because I had messed with him every single day about the books that he was reading. He would always turn his book over so that we couldn’t see the title of it. At the time I was working in the school as a G.E.D. tutor. And so I would come in, I was like, “What you reading today, officer? Ah look, man, don’t be ashamed of reading romance novels. Let us see that trade paperback you got.” And then the next day I would come back and you could always tell when somebody has a different book by the shape, the size, or whatever. And I was like, “Are you really reading all these books?” And the dude was like — you know those folks at Buckingham Palace that don’t speak? That’s who he was. He wasn’t having conversations with me, and yet we bonded in the only way that was permissible, which was a little bit of joshing back and forth. But he got me this job and if we would’ve had a Freedom library there, if he would’ve felt like he had permission to talk to me about what he was reading, to ask me what I was reading, it would’ve just been a more profoundly unique experience.

And so, we do it for the staff because I think that in some ways we have demonized people who work in prisons to the detriment of trying to have real systematic change. And so I’m trying not to demonize the people who work in prisons. I’m trying to recognize that staff in prisons have a higher rate of alcoholism than the rest of the society, a higher rate of domestic violence, a higher rate of suicide. Like, it’s poor health outcomes for everybody who has to spend a significant time in prison. We used to tell people when C.O.s are bothering us, “Yo, stop acting like you’re not doing a 10-year sentence too. In fact, I might got nine years, but you got 30 years and you just doing it 15 hours at a time.” But also, I’m trying to be honest. I’m trying to recognize that I am haunted by the fact that I put a pistol in somebody’s face and I carry around a deep sense of regret for that. And we live in a society that doesn’t give you permission to have that kind of regret, and like robustly say, “I want to do something about it, but I also want to do something for the people who have been just as wrong.” And if I am really going to say that in a full-throated way, I can’t get into that game of choosing who I want to demonize, because I already know that if we’re playing that game, I have so many failures, you know, that my house isn’t made of glass; my house is like in the countryside, in the open.

LEVITT: What kind of scale are you operating at so far? How many books have you put into prisons?

BETTS: I think one of your colleagues wrote Voltage Effect?

LEVITT: Sure, yeah. John List.

BETTS: I read his book like four times. And I spent a lot of time thinking about what he talks about in scale and how our project is a quintessential example of how you could fail that scale. Last year the goal was to do 50 libraries. We had done 10 at the June board meeting, and my board was really skeptical. They had questions about whether or not we would be able to reach our goals. But from that point in June to the end of the year, we built an additional 50 libraries. So, we entered this year having built 60 libraries. In January, we built 60 libraries alone. And at this point we’re on a pace to get about 200 or so this year. And our strategic plan that we are writing currently is to push the numbers up for ’24, ’25, and ’26 to about 300 to 350 per year. And we feel like we will over these three years learn what it means to scale in terms of: can we get to the point where we’re doing 1,000 libraries a year?

LEVITT: What’s the constraint? Is it money? Is it prison officials?

BETTS: It’s not prison officials. We always work with the commissioner or the secretary, whoever’s the leader of the Department of Corrections in the state; then we get the okay for all of the prisons. As opposed to hand-selling prison by prison, we could just sell state by state. So, we were on a call with all of Colorado and one of the wardens was the place that we were going to go to first. He was highly skeptical. And we show up at Colorado and I got on an orange fedora and some sneakers and some khaki shorts, and the warden is like, “Dwayne!” And I’m like, “Yeah, it’s a pleasure to meet you.” He’s like, “Man, let me show you this because, you know, I wasn’t really on board with this at first. I mean, I wanted to do it, but I was skeptical, you know, like anybody might be. But let me show you how you built one and now I need you to build 20 more.” And he goes to the housing unit, where they had a library, and it’s beautiful. People are talking and the books are amazing. And they’ve organized a collection of books to put the titles in it that we needed. And then he says, “Let me show you this housing unit.” And we go right next door. It’s no Freedom Library there. And for the first time in a long time, I feel like I’m in prison again. Now, I’ve been in 30 prisons this year. I’m in prisons all the time. But this was the first time in a long time that I felt like I might have to go in a cell in two seconds. And the reason is because it was so austere. It was just white walls. Nobody wanted to be out in a day room space because it was such a sad institution. And so I’m talking to the guys and I’m trying to explain to them what the Freedom Library is, and then they get engaged. And as we’re about to leave this guy reaches out his hand and I shake his hand and he says, “Thank you. Nobody comes back.” I leave the housing unit with the warden and the warden says, “You know, that guy was on death row for, like, 20 years and he doesn’t talk to a lot of people. This is why we need 20 more. Your presence, your bringing these libraries in here, it changes something about the fabric of what could happen in a moment. It might not change the whole prison, but it changes the fabric of what could happen in the moment.”

So, no, the wardens, the officials, the prison staff is not the reason why we haven’t gotten to a thousand a year yet. The reason is resources. And then the reason is we’re also in the process of literally figuring out what staff do we need to do 250 libraries versus the staff we needed to do 50? I tell people this all the time: The year I got locked up, the year I was sentenced to prison, was 1997. The state of California spent $3.8 billion on incarceration that year. $360 million was spent just to account for the new people that they arrested. Each of our Freedom Libraries is about $25,000, and that includes hiring the staff to actually build and construct the libraries. That includes the money that it costs to buy the books. And so, cost is an impediment and that’s why we’re constantly raising money. And we’re hoping over the next year to raise the $30 million that we’ll need to get to 2,000 libraries across this country. And we could devote our internal resources on doing the work and then be able to present that to the world and have folks reinvest and help us take this off.

We’ll be right back with more of my conversation with Reginald Dwayne Betts after this short break.

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LEVITT: There’s a lot of emphasis these days in the not-for-profit world on quantifying the impact of interventions. And in principle, I think that’s exactly the right idea. Philanthropists want to know how much good their donations are doing, but unlike for-profit firms — which have a relatively straightforward proxy for success, which is profit — in practice, it’s often hard to accurately measure a nonprofit’s impact. Freedom Reads I think is a great example of this. It’s difficult to know how many lives you’ve changed with the books, if you’re changing the way inmates are perceiving themselves. It’s just hard to quantify. And I’m not saying it’s impossible to do, it’s just exceedingly difficult and might involve randomization. You’re a small organization, plus you’d want to wait five or 10 years to see what kind of impact this was having on people’s lives down the road.

BETTS: So, that’s the critical question. I was in a visiting room once, I was visiting somebody in a New York prison. My visit was over, but I’m sitting down and I’m watching this man and this woman having a visit. The woman’s back was towards me, and I could see the man, and he was writing, and I was thinking, “This is so rude. You sitting down writing while this woman came to see you. This is disrespectful.” Mind you, I don’t know this dude. I should be minding my business. But now I’m intrigued. And then he says, “All right, I’m finished. Let me read it to you.” And he reads her a poem. And she says, “Yo, you just like a Langston Hughes.” And he says, “You know, a little bit like Langston Hughes; I got a little Shakespeare in me.” And then they start talking about how, like, they love books. And somebody mentions Beloved and they was talking about Ta-Nehisi Coates. She was like, “Well, when I was in school, I loved the Russians.” And she started talking about Dostoevsky and Chekhov. And he was like, “I never really loved the Russians, but I love something like Walter Mosley.” And now, as you could tell as I tell this story, I got intense. And I’m supposed to be minding my business, but I’m, like, fascinated, right? I’m literally taking notes. And so then either the man or the woman says, “We should read books together.” And the other one was like, “Yo, that’s a great idea.” And he said, “You know, I want to pick the first book.” And she said, “But how you going to do that?” And it was a pause. But what if he had a Freedom Library on his housing unit? When she said the Russians, he would’ve went back and said, you know, “I know we got the Russians there.” Because we have a browsing library and we create supports so if you get hooked on the Russians, you could find the resources. Like, there go Dostoevsky, there go Chekhov, there go A Gentleman in Moscow, which is a very new book that’s set in Russia that’s amazing.

My point is: how do you identify something like that and say that’s what we want to test for? How many opportunities like that did we create? And then we can make our own narrative about how that’s valuable. And you could agree or disagree with it, but we want to measure how many opportunities did we create like that, different kinds of communication with people and their family on the outside? But the key point you said, though, is that you really do need time. And time is a product of money. It’s really hard to think strategically about three years down the line, five years down the line, 10 years down the line if you don’t yet have a budget for that. But the other thing that I’ll say, I took a paralegal course when I was in prison, I also took a correspondence course in writing. That means that the prison allowed me to do that. Now, this is when they didn’t have Pell Grants and they didn’t have college in prison. So, what if somebody was like, “What’s the effectiveness allowing these inmates to do these correspondence courses? Because they do cost staff time. Is this beneficial?” Well, I graduated from Yale Law School. I graduated from the University of Maryland. I was the commencement speaker when I graduated. I had a full-tuition academic scholarship. And I’ve excelled at every point in my life in terms of applying the things that I learned in prison. But if you tried to measure the efficacy of anything that I was doing in prison two years out, three years out, five years out, you would’ve been like, “Dwayne is still unemployed. He still doesn’t have meaningful employment five years after he got released from prison. He’s making less than minimum wage teaching poetry to children. All of this was a waste.” But if you look another five years, “You’re like, wait a minute. He has created 11 jobs for other people. He has actually found a way to move from inmate to trusted collaborator with some of the most respected Department of Correction officials in the country.”

So what is the metric that we would’ve applied to my life to lead you or anybody else to want to support an organization that was trying to make me possible? That point about metrics is one that I struggle with because I understand why funders want to be able to see what they get for the support. But that’s why we bring you into the prison with us, because what you get is what you see in that very moment, and you witness two people around a book, or you witness how it literally does change the space. And we actually argue that the first metric of success is showing up. What does it mean to count that as a metric? What does it mean to say that we have been in more prison housing units than any other organization in this country, and we’ve done it in a short amount of time?

LEVITT: I mean, I share your feeling. The reason I ask that question is I feel like it’s become such a knee-jerk reaction on the part of funders to demand quantitative results. And I’ve come to bristle at that over time because I feel like — exactly what you said. A lot of what matters, we’re never going to measure using the kind of measures we have.

BETTS: The reason why that was a beautiful question is because it doesn’t get asked enough. And so, we don’t get to think about it in public. And I have struggled a bit, but I have benefited and Freedom Reads has benefited by the fact that some people think that in some real way what we are trying to do with Freedom Reads is like what I did with my life. And if that’s true in terms of me being a 16-year-old kid who was in a state that I didn’t grow up in, and I had no friends and no community; if I was able to not only survive in prison but thrive, and I have a trajectory now that I did not have before I got incarcerated, which means that what created this trajectory was what I did when I was in prison — a lot of funders have taken as an act of faith, maybe, that this is what has been missing from what we are talking about when we talk about criminal justice reform, like the literal transformation of lives on a wholesale level. I don’t care that the system is violent. I don’t care that the system is often racist. I don’t care that the system is unjust. I care what kind of life that my man has when he comes home from prison. And there hasn’t been the kind of robust work that takes that question and answers it the way I answered it for my own life.

And so, I think that the funding that we’ve had so far, it has been a lot of seed money that you would get in the for-profit space. That has been what was really irregular about Freedom Read’s trajectory. Mellon invested $5.25 million in an idea. But freedom is an idea. What is the Constitution but an idea? Sometimes I’m talking to funders who, like, may not know that California spent $3.8 billion on corrections in 1997. But if they know that, then when they look at my ask, which might be a million dollars, might be 5 million, might be 10 million, they know that it is a fraction of a fraction of a fraction of what was necessary to create this problem. So, why should they balk at supplying a fraction of a fraction of a fraction that might galvanize some real systemic change in a way that’s targeted at: who do you become when you leave a prison and how do you become that thing on your own? Because we are not a direct service organization. All we said is that a library is the field of dreams; that if we build it, they will come, and that some significant subset of folks who get connected to this thing will transform their lives. And I do want to tell you the one story about where this all came from, that conceptualizes why I think it is such a design-rich project, and it’s not just a book project.

LEVITT: Great.

BETTS: So, I ended up in solitary confinement in my first year in prison. I was in the hole like three or four times. And it was all for incidental contact with staff or somebody punching me in the face; and the hole was hard. And I remember, they stripped me of all my property. I hate to say this, man, but I was just so f***ing afraid. And you don’t really have permission to be scared in prison because who you going to complain to? If you scared, go to church. I looked at an image of myself from when I was 16. I graduated from high school at the county jail because turns out that when I was 16, I had enough credits to graduate from high school if I finished out my 11th grade year. So, I finished out my 11th grade year there and I graduated before I stood in front of a judge. And he sentenced me to nine years in prison. I was smart and I knew that books were like a kind of solace for me. So, I’m in the hole and I hear these guys yelling, “Yo, send me a book.” And then you could hear the paperback sliding across concrete and the book is going into cells. And I’m scared at first, but I’m like, “Yo, I’m going to ask him for a book.” “Yo, somebody send me a book.” And I ended up getting this book called The Black Poets and it changed my life. The first poem I read by Etheridge Knight was called “For Freckle-Faced Gerald.” It had a line in it that says, “Sixteen years hadn’t done a good job on his voice.” And it talked about how the 16-year-old kid ends up in prison and ends up being raped. And I’m reading this poem and there’s people that’s dealing with this in the prison that I’m locked up at, right? And when I read it, I realize that to be a poet and to be a writer and to be able to give life to somebody else’s story that could be unspoken is a kind of power. And I decided to be a writer.

But that’s not what birthed the Freedom Library. What birthed the Freedom Library, really, as I reflected upon it, is how this whole thing happened. Because if they strip you of your books in the hole, how do you get the books? Well, the prison, the buildings were parallel and in between each of the buildings, it was like a gutter space, 40-feet wide and 100-feet long, that stretched the length of the building that was like a no man’s land. And the C.O.s didn’t go back there either. So, between population and the hole, you had this space. Somebody would take like 20 feet of sheet that they ripped, and they would tie it to a shampoo bottle. And they would launch the shampoo bottle into the space between. And on the other side, in general population, somebody would take a sheet that’s ripped and a boot is tied to the end of it, and they would launch that boot into the space between, and then the two would tug at the same time so that the strings would connect. And then one person would pull the whole rope into their cell and they would sort of tie it off and then they would add a pillowcase to it and they would fill the pillowcase up with whatever they needed to put in it. So it could be food, it could be contraband, or it could be books.

LEVITT: Wait, let me just try to understand this — you’re managing with sheets and boots and shampoo bottles to create a communication network that spans across two buildings?

BETTS: Yes! You could be in your cell and look out the window, if you on the side facing that gutter, and see like 10 strings across the way from different cells.

LEVITT: Wow. That’s crazy.

BETTS: But that’s how the books get in. And so, the Freedom Library is just a new iteration of that. Like, we don’t need to use ripped sheets and pillowcases to create a mechanism of solace for people. I don’t know the person that gave me The Black Poets, though. I mean, that changed my entire life. And I don’t know this person’s name. The only time I thought about suicide in prison was when I was in solitary confinement. The only time I thought that, “I’m not going to make it out of this,” was when I was in solitary confinement. And these dudes created a mechanism to inspire me and allow me to confront what prison does to the spirit just by creating a mechanism that made it permissible for me to yell out to a group of strangers, “Ayo, send me a book,” and to expect to be greeted with generosity and not scorn. And the reality is that in general population, it doesn’t go down like that. You don’t just yell out and ask a bunch of strangers for something. But why do they do it in the hole? Because in the hole, you recognize that we all can’t run from our shared desperation. And so, then why do I build it for the housing units on the outside? Because now I have some of the skills to conceptualize — you know, a pulley system that’s predicated on boots and shampoo bottles and ripped prison sheets. We’ve done a similar thing except what we use is wood, beautiful books, and people.

LEVITT: You were imprisoned for eight years, starting at age 16, and you got out and you basically did everything right. You got a job at a bookstore. You started attending community college. You got a bachelor’s degree. You went to Yale Law School, the most prestigious law school in the country. But here’s the thing I wonder about. In some ways, our society is incredibly unforgiving. As you were doing the right thing, I suspect that you ran again and again headlong into the view that you were a criminal, that you were an ex-con, and people wouldn’t give you a chance. Can you describe some of those experiences?

BETTS: I had the opportunity to speak in front of a bunch of kids two weeks ago, and they said, “Can I ask you a question? You’re doing amazing. Have you ever struggled?” I start laughing, because you understand — I mean, I come out of prison and what happened is every time I was trying to make a way, prison kept coming up. I was so committed to going to college. I had a plan: “I’m going to get home, and then I’m going to college.” I didn’t know what college I wanted to go to, but I knew the University of Maryland was nearby and I knew that I loved their basketball team. So, I go to meet with the counselors in March. I said, “I want to attend school here. I’m just trying to learn what the steps are to apply.” And he was like, “Well, how old are you?” And I was like, “Man, I’m 24. I just got out of prison.” He said, “You should go to community college because I’m telling you, we’ve already made our admission decisions and we won’t be looking at applications again until such and such a date. But you could start community college as early as August.” And he was like, “You know, if you go there and prove yourself, I think that you got a shot.” And so, I immediately went to the college. And then I ended up getting into the honors academy at the community college. And that meant that I didn’t want to go to University of Maryland anymore. I wanted to stay because I had a guaranteed scholarship to Howard University.

Man, when I went to sign my paperwork at Howard — now mind you, I wrote an essay about having a felony conviction when I was planning to go. Like, I put it in my application. They asked the question, but nobody read the application because they had trust that the community college wouldn’t give somebody their scholarship that wasn’t a compelling and a great student. And yet, when Howard University was confronted with my felony convictions, they never got back to me. So, we was like, “Let’s pivot.” Because, you know, the train is moving and if I jump off to ask you why you don’t see me as somebody that’s worthy of redemption, of forgiveness, of mercy, of the possibility to be something more than what I was, then I’m going to ruin my own life trying to convince you of something. And so, I ended up applying for this Transfer Academic Excellence scholarship at Maryland — and this was like 50 years after Maryland University’s law school had rejected Thurgood Marshall because he was Black and he had to go to Howard. And so now I’m like, Howard done rejected me because I’m a felon. Is Maryland going to welcome me? And I remember doing this and there’s 12 people around the table. And they grilled me for a hour. And they say, “Do you have any questions?” I’m like, “Well, yes. We’ve been talking for a long time. And it is — I think they call it ‘an elephant in the room.’ I don’t know if you all know, but I went to prison when I was 16. And I know it’s a big deal and I just want to give you a chance to ask me anything you want to ask, because if it prevents me from getting this, I would rather know now.” And what they said was, “No, we know that, and we talked to the people that we needed to talk to. And you might not get this scholarship, but if you don’t, that’s not the reason.”

And so I think I’ve consistently been dealing with this. I’ve had jobs that I didn’t get. I’ve had jobs that I’ve been promised and then got snatched away from me. And sometimes you have things that happen and you just wonder, “Is this because I’ve been in prison?” I literally once had a university that wouldn’t bring me on campus for an interview to teach poetry that years later invited me to be the commencement speaker for the whole university. It is like, “Brother, I wasn’t good enough to teach your students — but now that Yale University has admitted me as a student; now that I’ve written a few more things; now that I’ve fulfilled the trajectory I was on when I wanted to fulfill it as a part of your institution, I get to be your commencement speaker?” I mean, this happens so much that it is an anchor that keeps me hooked to prison, for better or worse. I do think that I’ve dealt with these challenges and these frustrations, and I’ve often been reluctant to talk about it because I do feel like I’m demonizing people who were just trying their best and just failed at it. And I don’t want to do that. But at the same time, it’s like, I talked to Howard. They don’t even want to admit that they played me. They don’t even want to admit that they mistreated me because for them to admit that is to implicate them in the same burden that they’re having panels on all of the time throughout the year.

LEVITT: It seems to me that in a just society, a fair society, once you’ve served your time, the slate should be wiped clean, right? You made a mistake, you were punished for it, now you get a second chance with a level playing field. But that’s so clearly not true. And to your immense credit, you have overcome these obstacles. But I think about the millions of average people, you know, regular people who made a mistake, who come out, who don’t have your talent, and who face these obstacles, and is it any wonder they end up going back to prison? I really feel like somehow we’ve gone wrong in the society. I mean, this lack of forgiveness, it’s not consistent with Christianity or Judaism or Islam or anything. I don’t know, have you thought about that at all?

BETTS: Honestly, I think it’s predicated on a couple things. One, the fear is really real. And two, the demonization happens on both sides. We are so invested in figuring out who we’re going to blame that we create these structures of blame that I think make it hard to have some kind of commonality. And a lot of people would disagree with me with this, I’m just speaking about my own experiences and the challenges that I’ve confronted as somebody that had a lot of resources when I went into prison, that was able to develop some skills while in prison, and I’ve had a wild amount of support since I’ve come home. I do believe a fissure in our society is still our need to find a way to “other” people. I actually know that I did that with Howard just now. Like I’m mad, and in being mad, I want to say that, like, “You are the enemy.” Except the truth is that this was just one person or a group of people that made a mistake. And since this happened, the university, they had folks invite me out to give talks. They paid me to give lectures. Like, I get a lot of respect from people at Howard So, the reality wasn’t even pernicious. It was probably just like, “I just don’t know what to do because we don’t have a conversation about what to do.” And look, I put a pistol in somebody’s face. Nobody was going to get fired at Howard for not admitting me. Nobody was going to begrudge the person for making that kind of judgment call because we haven’t built a society that believes in redemption and mercy and forgiveness and second chances, as much as I think we might say.

You’re listening to People I (Mostly) Admire with Steve Levitt and his conversation with Reginald Dwayne Betts. After this short break, they’ll return to talk about whether Reginald Dwayne Betts suffers from survivor’s guilt.

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In the time we have left, I want to talk more about Reginald’s actual prison experience and also whether it’s hard on him psychologically to have achieved so much while so many others in his situation have struggled.

LEVITT: Most of the people who are listening to this podcast will have had no direct contact with prisons. Their image of what prisons are like is driven almost solely by Hollywood portrayals, which are prone to sensationalism. Could you describe an average day in prison? Partly I’m interested in the rhythms of the day, but much more than that, I’m curious about your mental state. Were you dominated by boredom, by anger, frustration? 

BETTS: I would say first, every prison is different. But that first camp, I would wake up in the morning, you would go out to breakfast, then you’d come back in, and then you would go out to rec. But if you didn’t have rec, then you could go to school or you could just hang out in a day room. It was some boredom because I was young and what was there to do but gossip and walk around? We didn’t have weights there, so you couldn’t really work out necessarily. So, that was the rhythm of that prison. But then for the next prison I went to — it was called Red Onion State Prison, it was a super maximum security prison. We were in a cell like 23 hours a day. We came out to go to lunch And then, like, twice a week we could go out for an hour on the rec yard. I was there for, like, about five, six months. And then I was at a place called Sussex One State Prison, which was essentially the same. And I was there for two, three years. And it was a stretch of time that I couldn’t even go to the cafeteria. We just lived on the unit. They brought us the food. And the days were boring because you were in your cell sometimes 24 hours. Sometimes you would allow one hour on a day room to take showers and use the phone, but it was brutal. And then after that, I went to a place that was more open. It was a lower security campus and basically the doors were open all times except count time at that place. I used to spend five hours a day learning Spanish. I did a lot of exercising, a lot of working out. I worked as a G.E.D. tutor. I worked as a law clerk. but also I did a lot of writing independently.

LEVITT: Since you came out of prison, nobody could contend that you haven’t made the most of your opportunities. You’ve just done amazing things. It’s interesting that you were not a model prisoner at all. You were constantly being sent to solitary confinement. Do you think that part of your success outside of prison was the same reason you were getting sent to solitary while you were in prison?

BETTS: Well, no, because the first time I went, I was 16, I was at a county jail, and I was a little afraid to be in a housing unit that I was in. I had just got there. I was the youngest person there. And you could write yourself out of the block and you could make up some innocuous reason, but the staff always knew that you were afraid. And I did that, but I felt like a coward for doing it. And so when the staff came to move me, I was like, “Nah, I’m good. I’d rather stay here.” And I’m so naive, I’m thinking that’s an option. And he’s like, “No, you either move with me or you go to the hole. You know what? You going to the hole.” And I touched his arm. It’s like — “No, I’ll move.” I just touched his arm. He slammed me on the wall, threw handcuffs on me, dragged me down the steps and said I assaulted him. And I did 10 days in the hole for that. I get to the next prison. I just didn’t let the officer close the door. I was frustrated because everybody else was walking around and I just wanted to go get me some ice. And she tried to slam the door closed. And I was like, “You can’t close my door.” I’m all of a fool, you know, I’m like 16. And so, she writes me up for assault and I do six months in the hole for that. The third time, a C.O. was searching me and they grabbed my genitals, and so I took his hands off me. Well, he said I assaulted him. Six months in the hole for that. Most of my charges happened on the front end of my bid when I was a child. You know, I talked with my hands. I’m not trying to make myself out to be a better prisoner, inmate, rule-follower than I was. But I was not a threat to institutional security. I was not causing people problems. I was not gambling, I was not making mash. I was not drinking mash. I was not fighting people. I wasn’t a model prisoner, but I do think that in a different system that was searching to cultivate the skills and the talents and the personalities and just the rehabilitation of people inside, I would’ve been a model prisoner because I would’ve had mentors around me.

LEVITT: So you got out of prison and you made the most of your second chance. Do you suffer at all from survivors’ guilt? There were so many people you knew in prison who are never getting out because of life sentences, or people who got out, but they didn’t have the skills or the luck or the support that you had, and they ended up back in prison. Are you haunted at all by the thought that so many are left behind, trapped in the system?

BETTS: You know, in the past three, four years, I’ve gotten Christopher Tunstall out of prison. He had two life sentences. I’ve gotten Rojai Fentress out of prison; he had 53 years for a crime he didn’t commit. I’ve gotten Terell Kelly out of prison; he had 40 years for a murder he did commit. I got Kevin Williams out of prison; he had a life sentence for a robbery he was involved with. I also spoke on behalf of his friend and co-defendant, and he was awarded parole as well. I got another friend of mine out, who was locked up in New York, who I didn’t know before — he was the first person I got out. He was my client; I was a law student. And so, I’ve had a chance to try to do some meaningful work. And Terell, and Fats, Rojai. I knew these guys as a kid. I mean, we were in the system together. Chris, he was my cell partner, you know what I mean? When I was about to get in a fight with somebody, he, like, jumped up. And I’m like, you know what? Him jumping up is what made me not fight. Because I was like, “Yo, you don’t need to lose this, and not for me.” And he died tragically six months, after he came home. But, like, he came home. And so I don’t know if I have survivor’s guilt. We all did things and I’m just not going to carry that.

But I do have a real sense of duty and responsibility for myself, my family, for my friends incarcerated, but also for this country. Because you could judge a country by how he treats the people that’s in prison. And I am an American citizen. I consider myself a Black American poet. You know, I write about what it means to live in the world through this particular lens. And so, I care about what we do to people in prison, and I think we all should. What I have is a profound sadness, thinking about what it meant for me to be in a courtroom that would look at a 16 year old kid — and the judge said to me, “I’m under no illusion that sending you to prison will help,” and then he sends me there. And I was 5’5″ and 125 pounds. And I think my biggest challenge today is the realization every single day that I am not, in a really profound and realistic way, supposed to be doing anything that I’m doing right now. When people salute me, they pretend like it doesn’t matter that this is profoundly absurd that I’m able to do this. They pretend like they don’t understand that the system that we have created has not just made my life an impossibility for so many people, but like, an understood impossibility. And I think that’s what bothers me most, because I go into these spaces and I’m asking myself: How are we still able to do this? Let’s just ask ourselves: What duty do we owe?

And Hamlet, you know — Hamlet is riffing, he’s mad, and he’s like, he’s going to do this and do that to this person. And then his friend Polonius is like, yeah, give him what he deserves. And Hamlet’s like, wait a minute, wait, wait, wait. If we give man what he deserves, don’t we all deserve the sword? No, I should give man what I believe that I deserve to give him by right of me being a human in this world. The reality is that if we keep saying that what people deserve is prison, we will realize that that’s what all of us deserve, and that’s not what all of us deserve. I think all of us deserve to have access to the principles this country was built upon. And fighting for that is what gives me some sense of hope. Because I think knowing somebody was fighting for that is what would’ve given that kid hope to actually believe that what I am today was possible, because I was just trying to survive. Maybe if a Freedom Library existed when I was inside, I would’ve actually had ambitions to do any of these things. I have stumbled into quite a life, but I would be lying to you if I said that any of this was planned. 

All I can say is that I think Reginald Dwayne Betts is amazing. Everything is stacked against you when you spend your youth locked up. So many years of education and early job experiences missed; the emotional scars of eight years in confinement; the social stigma associated with being a convicted violent offender. That he has overcome all that to help so many people blows my mind. Right after we ended the interview, Reginald invited me to help be a volunteer building a library in prison with him. I cannot wait to do that in the upcoming year. This conversation inspired me to give financial support to Freedom Reads. If you would also like to make a donation to help support their activities or just learn more about what they’re up to, check out

LEVITT: And this is always a point in the show where we take a listener question and my producer Morgan is always here to help.

LEVEY: Hi, Steve. So at the end of our last episode with former Googler and now mental health entrepreneur, Obi Felten, she said she felt like an imposter with nearly everything she’s tried over the course of her career. And you commented that you also felt like an imposter. So, we asked our listeners to send us an email saying whether they felt like an imposter or not. And we got a lot of emails.

LEVITT: This is our record, don’t you think?

LEVEY: We definitely got a lot — hundreds of emails. So, you tallied up some data. What’d you find?

LEVITT: Okay, so just the bottom line, if you tally up all of the responses, what’s your guess, Morgan? Impostors or not impostors? What are the majority of our listeners self identifying as?

LEVEY: I would say overwhelming imposters.

LEVITT: Well, I’m an imposter, and are you an imposter, Morgan?

LEVEY: I’m an imposter.

LEVITT: Okay, it turns out that about two thirds of our listeners self-identify as impostors, which is an overwhelming majority, although honestly, in subtle ways, we encouraged people to say they were impostors. I bragged about being an impostor, and Obi bragged about being an impostor. So, we made it really easy for people to say they’re impostors.

LEVEY: It was a safe space.

LEVITT: Okay, so that’s the overall result, but what’s usually more fun in data science is when you try to then strip down from the basic, first-order facts to understand some of the subtleties, which might get you more into the theory of understanding what might be the source of people feeling like an imposter? Really, we don’t have very much to go on. We have one line emails, and the only real data we have about people are how quickly they responded after the episode was posted; their gender, to the best of my ability to guess it, based either on their name or, in some cases, their picture. Some people have a picture embedded in their emails, and some people don’t. And so, that was the third dimension I looked at. And I didn’t really have any strong hypotheses on any of these dimensions, but it’s what I had and it was costless to tally it as long as I was collecting the data anyway. 

LEVEY: So you went with what you had.

LEVITT: I went with what I had. Okay, so I’m going to quiz you, Morgan, on what you think I found. Now, you’ve also seen some of the emails, but it’s not that easy when you just look at a bunch of emails to draw the kind of conclusions you can draw when you’ve actually tallied the data. So the single most striking finding in the data had nothing to do with being an imposter. It was the composition male-female of who wrote in. So, Morgan, what do you think? Do you think we tend to get a lot of emails from men or from women?

LEVEY: Oh, well, in general we usually get a lot more emails from men, so I would believe that that stood true for this imposter email as well.

LEVITT: Eighty percent of the responses were from men. You don’t think 80 percent of our listeners are male, do you?

LEVEY: I would say it’s slightly less, but that doesn’t surprise me.

LEVITT: Now let me ask you, who do you think is more likely to feel like an imposter? Is it the men who wrote in, or the women?

LEVEY: I’d say it’s the men.

LEVITT: Really, so I would have guessed, just because society imposes all sorts of stuff on women that doesn’t on men, that it would have been women. But we both are wrong. It was exactly the same. Men and women, both, classified themselves as imposters almost exactly two thirds of the time. So, overall and by gender, two thirds of the people who responded called themselves imposters.


LEVITT: Another dimension I looked at was how quickly people responded. What do you think the relationship was between being an early responder, a late responder, and being an imposter?

LEVEY: I bet that the people who responded right away were more likely to say they were an imposter because they wanted to agree with you right off the bat.

LEVITT: So it turned out: no difference at all. The rate of imposter-ness was constant across the early and late responders. Okay, the last dimension we had was pictures. Do you think that there would be any difference in the rate of feeling like an imposter of the people who had pictures associated with their emails or didn’t?

LEVEY: Hmm. This is a tricky one because I see so little correlation between these two things. I’ll say that there’s no difference, because that seems to be the answer for everything else.

LEVITT: That is a good answer, but it turns out to be totally wrong. The only huge difference I saw on any of these dimensions was that people who had a picture associated with their email, 80 percent of those people feel like imposters, but only 55 percent of the people who don’t have pictures feel like imposters. And that is a big difference, highly statistically significant, and really very striking for exactly the reason you said, which is: why in the world would that be true? We could start talking about hypotheses and in essence really in data science, it’s always much easier to come up with a correlation. Actually explaining the “why” — coming up with a good hypothesis — is harder. 

LEVEY: So, after doing all this analysis, do you have any theories why so many of our listeners believe they’re imposters?

LEVITT: Without having thought about it very hard, I’ve always just assumed everyone feels like an imposter. You’re an imposter and I’m an imposter, so maybe imposters just like to gather together and so the cause of us having so many imposters is that we’re imposters.

LEVEY: Well, thank you to everyone who wrote in. If you have a question for us, our email is PIMA@freakonomics. com. That’s P-I-M-A@freakonomics. com. We read every email that’s sent and we look forward to reading yours.

In two weeks, we’ll be back with a brand new episode. And I hope you are ready for a wild one, because my guest will be Avi Loeb, the Harvard astronomer whose research on alien life has proved to be extremely controversial.

LOEB: “Do we have a partner? Is there someone out there in interstellar space that perhaps is smarter than we are, that we can learn from?” That to me is a very important question because it’ll change the future of humanity.

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People I (Mostly) Admire is part of the Freakonomics Radio Network, which also includes Freakonomics Radio, No Stupid Questions, and The Economics of Everyday Things. All our shows are produced by Stitcher and Renbud Radio. This episode was produced by Morgan Levey with help from Lyric Bowditch, and mixed by Jasmin Klinger. Our theme music was composed by Luis Guerra. We can be reached at, that’s Thanks for listening.

 BETTS: Certainly you took a paralegal course, you wanted to be a lawyer.” “Nah, I ended up going to law school because I couldn’t get a job.”

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