Episode 58

Reginald Dwayne Betts

Episode 58

Reginald Dwayne Betts on How Freedom Can Begin With a Book

Interview by Spencer Bailey

For Reginald Dwayne Betts—a poet, lawyer, and activist who supports and contributes to prison decarceration efforts—reading and writing have a mind-expanding power that never wanes. The author of three books of poetry and a memoir, his prose is intimate and raw. Even when he’s not writing about himself, Betts finds ways to build personal connections with his subjects for his award-winning work in The New York Times Magazine—subjects that have included the rapper Tariq Trotter of The Roots, the late actor Michael K. Williams, and Vice President Kamala Harris. He also brings a literary bent to his activism: In 2020, he founded Freedom Reads, a nonprofit that aims to build libraries inside 1,000 prisons and juvenile detention centers across the country. The program recently installed its first sets of bookshelves at MCI-Norfolk, the Massachusetts prison where Malcolm X was incarcerated, and last month, in a public event at the National Building Museum in Washington, D.C., it presented the 500 titles that comprise each collection. 

Betts, a graduate of Yale Law School (where he’s currently in a Ph.D. program), became an advocate for respecting the rights and dignity of the people who are in or who have gone through the American carceral system after experiencing it firsthand himself. His life changed in a span of 30 minutes, a window of time that occurred in 1996, when Betts, then 16, was arrested in northern Virginia in connection with an armed carjacking. He was later tried as an adult and sentenced to nine years in prison. 

Instead of resigning himself to the violence and dehumanizing conditions of incarceration, Betts turned his focus toward books, many by Black writers and poets. After someone slid an anthology called The Black Poets under his cell door, Betts began saving his 23-cents-an-hour salary to buy more. Reading works by poets such as Lucille Clifton, Rita Dove, and Etheridge Knight, the latter of whom also did time in prison, showed Betts the depth and richness of self-reflection, and opened him up to other worlds. He started thinking about the stories he himself had to tell, and that writing about them could help him, as he puts it on this episode of Time Sensitive, “become somebody.”

On this episode, Betts speaks with Spencer about the long-term impacts of his time behind bars, the current renaissance of prison writing, and the transformative act of giving people who are incarcerated access to literature and books.


Betts describes the differences in how he understands and thinks about certain periods of time—before, during, and after prison.

Betts reflects on the phrase “doing time,” and how it’s impacted him since his release. He also talks about the work he has completed during the pandemic, including starting Freedom Reads and writing a play. 

Betts speaks about how Black men were portrayed in ’90s media and pop culture, and his conviction within that context. He also recalls his release from prison on March 4, 2005; a difficult conversation he had with his mother the day he got out; and why he wanted to write about Michael K. Williams for The New York Times Magazine following the actor’s death last year.

Betts discusses the books he read growing up and while he was behind bars. He also talks about meeting three of legendary Black poets, Elizabeth Alexander, Rita Dove, and Lucille Clifton, at a poetry workshop.

Betts describes how he found his footing after prison. He also speaks about the writers who are contributing to what he sees as a current renaissance of prison writing.

Betts details his hopes and aims for Freedom Reads. He also recites a recent poem called “Memorial Hoops.”

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SPENCER BAILEY: Joining me in the studio today is Reginald Dwayne Betts, a poet and a lawyer, or, as he has identified himself, a “lawyer poet.” 

Welcome, Dwayne.

REGINALD DWAYNE BETTS: Hey, thanks. It’s a pleasure to be here.

SB: I want to start this conversation by bringing up several amounts of time, specific periods of time, for you to explore what comes to mind with each. So, I wanted to start with sixteen years.

DB: That’s how old I was when I got locked up. My oldest son, [Micah], is two years away from being 16. I think 16 is crystallized in my head as an age. It’s sort of the year in which you feel you come into adulthood. We in New York. In New York, 16 used to be the age of [criminal] majority. But also, for me, it’s that year that my life radically changed forever. 

I actually was looking at pictures this morning. It’s so.… Wow, man. I was looking at pictures from when I was 14, 15, and 16. You can’t see, in the 15-year-old, what’s going to happen next. And I look so young. And you have to understand, when you’re a child, you really only know baby, and older, and like, old. And so, when I was 16, looking at myself in the mirror, the kid that was taking those pictures thought he was, you know, so grown and sophisticated. And I look at that picture as an adult and think about…. [Sighs] Yeah, a lot can change really quickly.

SB: I mean, you had braces when you were in jail.

DB: I know. [Laughs] Now, everybody gets braces, right? A lot of adults walk around with braces. But back in the day, you really only had braces as a kid, and I get locked up and I got braces on. I guess what I mean by that is: In 1996, braces were a signifier of being a child in a way that it’s not now. And so when I walked into that courtroom without any hair on my face, a hundred and twenty pounds soaking wet, and with braces on my teeth, what amazes me still is that the prosecutor and the judge could see somebody they imagined should be in prison for a long time. 

Everybody in the courtroom understood what prison is, and the violence in prison, and the danger. And that’s all they really understood about prison. They didn’t understand about the brotherhood. They didn’t understand about the laughter. They didn’t understand about the struggle to find remorse, and find redemption and rehabilitation. So it’s not as if they sent me there expecting me to find those things. They sent me there knowing full well the understanding of incarceration that most of them had, being actors in the system, was just the depravity, the violence, the recidivism, and it made sense to send a 16-year-old kid there. I [don’t] think they felt if they sent me there, I would end up at Yale Law School.


SB: We’ll get there. The next period of time I wanted to bring up is thirty minutes.

DB: Writing a book is really difficult. And I was thinking about how to structure and think about the book [A Question of Freedom: A Memoir of Learning, Survival, and Coming of Age in Prison, published in 2009]. And it struck me that the entire crime I committed took thirty minutes. You just don’t think about…. I mean, who at 16 thinks about thirty minutes mattering for their entire life? And it did. When I started the book out, I was really starting to contemplate how what prompted the book was the thirty minutes that so radically put me in positions that I never expected to be in. 

And that goes back to being 16, though. Because it takes a 16-year-old to imagine that you could pull a gun out on somebody, and it wouldn’t change your life forever. I mean, that’s a product of being, I think, foolish, and a kind of foolishness that is particular to children. No adult, I think, really would think that. But, yeah, thirty minutes. I think from start to finish, you know, I committed two crimes—well, committed more than two crimes, but two incidents—that landed me in prison for some time.

SB: What happened to your sense of time when you were in the act of that carjacking? And also, I’m wondering how you were thinking about time while you were being arrested and booked. Could you speak about those moments through the lens of time?

DB: I guess the crime is fast and slow, because I only had a gun in my hand once. And so I wasn’t.… I wasn’t used to it, and I wasn’t a particularly brave kid. I wasn’t a particularly tough kid, either. And I had too much in my head. I had a classmate who had a relative attempt to carjack somebody, him and a couple of his friends. One of them had a sawed-off shotgun, and they were running up on an undercover cop, and the cop saw the sawed-off shotgun and started firing. And so I had that in my head. 

It was somebody else who had carjacked somebody at a mall, and the person had a gun. And so, as the kid drove off with their car, he shot the kid in the head. I had these incidents in my head, which is, you know, both slowing time down a little bit, because I was thinking about it. And so, it felt a little surreal. But then it all happens really, really fast, too. 

The next thing I know I’m driving down the highway. And I remember every detail of it. I remember what the air smelled like. But like, the guy was asleep in his car. I’d come home and I would go to sleep in my car, and think about it. Like, Man, somebody’s going to rob me. 

I remember one day, I was living in D.C.—and I was always exhausted, and I fell asleep. I’ve wrecked two cars, falling asleep while driving. So my wife has a rule: I can’t drive for more than forty-five minutes, and definitely not by myself, because I’d fallen asleep…. Both times, it was during the daytime. It wasn’t in the middle of the night. Once, I didn’t have children; once, I had two kids. So I can’t really blame it on the exhaustion of parenting or anything like that, right? 

The point is, I’m asleep in my car, and somebody bangs on the window, and I’m like, “This is fucking karma.” But it was a cop. And it was a cop asking me for my license and registration. He’s like, “You can’t fall asleep in a neighborhood like this. This is a dangerous neighborhood.” I was down the street from my kids’ day care, and I was just catching twenty minutes of sleep before I had to get on the highway and drive for an hour and a half through traffic. But, yeah, thirty minutes can change everything, and it will give you the memories that stay with you.

SB: What about time when you were arrested and booked? What was that like?

DB: That morning, I knew I was going to get locked up. It’s confirmation bias in a way, because if you commit a crime, and you say, “I’m going to get locked up”—you committed a crime, you’re probably going to get locked up. But it was something about the morning, and we went out anyway. We were going shopping, and then something wasn’t right at the register, so we leave. And then we’re running, actually, because somebody called our name or something, and so we’re running through the mall. It all happened so fast. And I had this guy’s wallet and shit on me, as if, if they asked me for ID, I’m going to give him my ID. I’m going to see Black No More tomorrow, and it was almost as if I was carrying his shit around, as if the carjacking made me him. 

Then the police chasing me made me realize how absurd it was. Pulling a pistol out on somebody will not turn you into a middle-aged white man who probably was just trying to get home to his family. And so I’m shedding his identity as I run. We ran to the Pentagon, which is also not the ideal place to try to escape from the police, because there’s more guns in the Pentagon than anywhere in America. I think [more guns are there than] anywhere in the world.

SB: And also where your mom worked.

DB: Also where my mom worked. But maybe that was… Who else was going to keep me safe? So. But the police, man, they pulled out so many guns. 

We started to run to the train station and something stopped us. I don’t know why we didn’t…. We probably would’ve been better off if we tried to jump on a train. In a way, though, things just gotta come to an end. You don’t want to…. It’s just a lot of tension to have to carry around—people looking for you. And I’m not saying that we intentionally got caught. I’m just saying, in retrospect, it probably was better off to get caught then, than to have people looking at the video and they be like, “Can we find this kid?” And then your face is on the news, you know, “armed and dangerous.” You don’t want to be that person that they’re looking for. 

But so we running, and the cars surrounded us and there was so many guns. And then time just kind of stopped. You’ve got your hands up, and they’re like, “Don’t move, put your hands behind your back. Don’t move. Get on your knees.” It’s like, “Yo, slow down. What exactly do you want me to do?” 

I actually didn’t think they were going to shoot me or anything like that, though. Even though I knew [about] Sean Bell, but honestly, it wasn’t a concern. A couple of months later, though, friends of mine stole a car, got caught out there, and got caught on the Pentagon, and they did shoot that car up. So, you know, luck of the draw sometimes. I remember them putting us in the back of the paddywagon and just thinking.… It just feels like your life is over. Time doesn’t even matter anymore. It’s just like, “This is the worst place on the planet to be.” 

SB: The next period of time I wanted to bring up was nine months. What comes to mind for you with nine months?

DB: I don’t know, that’s a good one. I guess that’s how long it takes to have a baby. 

SB: [Laughs]

DB: I have two. That’s the first thing.

SB: Well, I found it interesting, you spent nine months in jail, and it was basically like being birthed into this prison system.

DB: I guess that’s true. I hadn’t thought about it like that, because that nine months didn’t register in the same way. Because, honestly, when you get in there and you’re a  kid…. Anytime you’re locked up, what it is, is if you find a place that you’re comfortable with, you almost don’t want to leave. And actually, I think about it now, that I didn’t get birthed into prison as much as kicked into prison. Because you don’t learn anything about really surviving prison in a jail. I mean, all those places could be brutal. All those places frequently are brutal. And that’s not all they are, but the weight of the brutality, if you’ve got to suffer it, almost always outweighs everything else everybody else experiences. 

Every analogy I could think of is going to be gross, so I won’t—the comparison won’t work. Or maybe this one will, because I made it up. It’s like, you could walk across the same street every day, for five years in a row. And then, one day you cross the street, and somebody makes an illegal right turn, and hits you, those other safe days don’t matter anymore. And when people talk about the street, they won’t remember that. But if anybody talks about the street and you, you will always have a sour feeling about it. And I think that’s what incarceration is. 

The way we think about incarceration—all of us—is if we’re that person crossing the street. And so, it doesn’t matter if most of prison isn’t violent. It doesn’t matter if the worst things don’t happen to most people. Most people’s understanding of prison is always going to be rooted to that one horrific thing that you hear about, because it does outweigh everything else. And actually, prison is filled with so many mundane atrocities that the accumulation of it all is another reason why the weight of one thing matters most. 

And so prison—jail, per se, didn’t prepare me for any of that. It didn’t prepare me for walking the yard. It didn’t prepare me for the absurdity of them giving me a yellow ID card because I was under the age of 18, and I couldn’t buy tobacco. So I was walking around with juveniles like me who had life, but they couldn’t get lung cancer. It was like, “Thank you for thinking so much about me.” So, it’s interesting. If I wrote that in a book, that’s one that doesn’t stand up in the same way, because nine months doesn’t have the same significance as thirty minutes. When you say thirty minutes, I—

SB: Yeah. And the last period of time I wanted to bring up was eight years.

DB: That’s the stretch. That’s the time I spent in prison. And if you’d have said “six months,” because I spent six months in the hole, twice, and I think that was…. If you said “ninety days,” which is the sentence that you—and I got two ninety-day sentences back to back in the hole—I think that was a lot. You learn a lot about yourself. This is like two cells, easily.

SB: This room [we’re in]?

DB: Yeah. And two nice-sized cells, though. You know what I mean? It’s rough to spend that much time in it, and just have a door that doesn’t open. And in eight years, it’s weird. I was working on a piece [for The New York Times Magazine], and I was talking to a friend about keeping track of time through music, listening to The Roots. You know, certain artists that—I listened to them before I came in, so I was listening to them when I was in and waiting for that new album. And my clock was different from their clocks. I didn’t realize that they got one that came out in ’95, and then the next one comes out in ’96, and then the next one comes out in ’99, and it feels like forever. It feels like, “What are these dudes doing? When is the album going to come out? Can’t they just record music?” 

And then the next one comes out, maybe 2002, and still, it doesn’t feel like…. Over the eight-year span, Tipping Point came out. So, first it was Things Fall Apart, then it was Phrenology, ​​then it was Tipping Point. Three albums that was really important to me in different ways, but three albums that tracked that eight-year time period, and it doesn’t feel like, in any way, that those three albums really represent eight years, as an adult, reflecting on them. But when I was inside, I needed something to help me measure how the world was still moving. And now, I don’t know, it used to be, I came home from prison, eight years was a third of my life. Now it’s like a fifth of my life, and it’s weird. You keep getting older, and the percentage of the time spent in prison keeps shrinking, but the fucking weight of it doesn’t. It’s just some weird calculus where the footprint never changes, but somehow the size does.

SB: Yeah. I was struck that last year marked sixteen years since you’d been out, the same amount of time you’d existed out prior to prison.

DB: Yeah. And I would forget…. I wonder, seventeen, eighteen, nineteen, twenty, twenty-five—these are all horrible anniversaries to have. And I know some people don’t even remember it at all, because they’re not as obsessed with numbers as I am. I think numbers mark some mathematical clue to understanding existence.

SB: In your memoir, A Question of Freedom, you explore these various experiences and perspectives around time and particularly, doing time. I was wondering if you could share some of these. Maybe even, let’s just start with the phrase “doing time” itself.

DB: You know, there’s the saying, “You do the time, or you let the time do you,” and doing time is like…. It’s weird. It’s trying to turn this concept into a material good, that you are actually doing this thing, that you are finding a way to dig a hole, or to build a monument. But that you aren’t just in purgatory—you aren’t just in a stasis. 

And everybody thinks about it different. Like, “What are you doing, man?” You’re doing time. In that it’s this obligation that you can’t let go of. It’s like Sisyphus, or, what’s the other cat? Tantalus. It’s like, This is what you owe. You have a choice that—well, actually, you don’t have a choice. You could do it and then, when people say, “You could do the time, or let the time do you,” I think the idea is that they’re trying to take ownership over the act of doing the time, even though it’s like, probably no real…. Yeah, I guess it is. And you’ve got to believe it is, because otherwise you just waste away. And I think that’s what it is. To do time is to be like, “Can I have some direction with what’s going on in this space?”

SB: Of prisoners, you wrote, “Our occupation was time.”

DB: Yeah. I stole this line from [Black] Thought: “Clock With No Hands.” And it’s interesting, because I use it a few times in the book, and it’s this idea of like, What does it mean when you have no time, though? What does it mean when you have the structure, the notion of time, but you don’t…. And part of it is because, inside you…. I mean, I was in puberty when I went to prison. I was going through puberty, and discovering who I was in a prison cell is…. I don’t even know if that’s a discovery. And I got homies now who have been locked up since they were 16, and they still locked up now. 

You think about time. I’ve been free sixteen years. I’m going to make a list of things that I’ve done in my life—and not accomplishments or anything, I’m just talking about…. [Laughs] I was in Maine one time, and Maine is the whitest place in America. I got two Maine stories. One is, I was in Maine, and I was with two friends, and I was at a poetry reading, and they had my car all day. So then I’m driving back to the hotel, and the car just stops. Everything on the inside shuts down. And I’m embarrassed. I’m like, “What the fuck?” And what do you do in a situation like this, when your car just dies? And then I’m like, “Wait! Did y’all put gas here?” And he’s like, “Ah. We should have did that.” The gas station is a thousand feet away. And me and one of my friends get out, and the one that can drive gets behind the wheel to just keep it straight. And I drive an S.U.V. And we get behind the S.U.V. as if we’re going to actually move this motherfucker. You’ve got three people with Yale law degrees, and we actually think that we’re going to move the S.U.V. 

SB: [Laughs]

DB: Then one white kid, who weighs less than I did when I went to prison, runs across the highway to help us push. He’s pushing, and then three frat boys stop their car and jump out, too. Now there’s five of us pushing. The truck doesn’t go anywhere because the truck weighs two tons, or something ridiculous like that. But it was beautiful,though. Because it was all of these folks. It’s late, too. It’s not wintertime, it’s spring, but it’s 9:30, so it’s pitch black. And I’m like, “I think I should just walk to the gas station, y’all. Thanks for coming to help.” 

So I’m walking to the gas station. A white woman with her daughter sees my friends in the car, stops her car, says, “Why are y’all sitting in the middle of the street by yourself? This is not a safe place. The middle of the street is never safe. I don’t care how friendly we are in Maine.” And waits with her daughter, because they’re going to do something when Freddy Krueger comes out of the woods, right? When I come back with the gas canister, she’s like, “Why would you leave them by themselves?” I was like, now I’m apologizing, I’m like, you know, “I’m sorry. [Laughs] I was just trying to get some gas.” Anyway, the whole point of this story is that you expect one thing, and you get something completely different. And that happened to me in those sixteen years. 

Then, once I was in Maine with my wife and my kids, and we were just driving around. We went to the spot where you can see where the ships used to get built. And I’d never been fishing before. There’s this white dude with all of these tattoos and shit, and I’m immediately stereotyping him. He’s got a bunch of tattoos, this is Maine. This is an unsavory character. Then I feel bad, because I’m like, “Damn. This is what it means to be a cop in New York.” And so my wife is like, “Yo, what you saying?” I’m like, “What’s up? What’s going on, man?” He say, “Hey, how’s it going?” He’s got four fishing poles, and he’s with this woman, and they’ve both got one. She was like, “You should ask him to fish.” And I was like [whispers], “I should ask him to fish? That’s a stranger.” [Laughs] I was like, “He’s not even watching his dog.” His dog is just running all around. At the time, me and my family don’t have a dog, so we not dog people, so we don’t get it. We kind of get it now—the dog was having free time. 

My wife was like, “Yeah, my husband has never been fishing before.” He say, “Oh. Hey, you want to cast?” I was like, “Yeah.” I cast the line out, and then the woman he’s with catches a fish. He said, “You want to reel it in?” It’s her fish! I’m like, “Sure.” I reel the fish in, then he’s like, “You want to hold it?” And you know, I don’t want to hold no fucking fish. 

SB: [Laughs

DB: He’s like, “You just hold it by the gills.” I ain’t trying to look like no sucker, though. So I hold the fish, and then I drop it. I was like, “Oh shit.” It jumped out of my hand. He looks at me, and he picks the fish up, and he throws the fish back in. I was like, “You just threw the fish back in?” He was like, “Yeah, it’s sport, man. This is just sport. It’s just a thing. This is what people do.” 

And so, he was like, “Hold up, do you want to cast your own line? Because I’ve got some extra poles over here.” And then we talking, and the dude was like, “Yo, are y’all here visiting? You should check out this fort. It is one of the oldest forts in the country, one of the oldest forts from the Civil War. Maine sent more soldiers than anybody else to fight in the Civil War.” I’m looking at this dude. How the fuck do you know this? [Laughs] It’s like, I know he’s lying to me, and then he pulls out his phone to make sure I know how to get there, and it was wild. It was just exactly the experience I didn’t expect to have. 

And I read one of these amazing letters—apparently people during that time period was far more literate than we were, and they wrote more letters, and they wrote more letters to newspapers. Somebody was writing a letter explaining why they were fighting in the Civil War. He was like, “Because it’s my duty to. And if I don’t, what does it say about me?” 

Anyway, I got this list of experiences. And those are just two wonderful Maine experiences. I’ve actually got two more, but I’m not going to tell you those stories. But the fact is like, Maine—and I have people who have been in prison in Virginia for the  last twenty-five years—and it’s like, what do we deprive people of under the guise of them deserving it? My own violence is a complicated thing that I grapple with, but I think that … I don’t know. It’s a hard story and it’s hard for me to think about time as a thing that contains so much of what was lost. Opportunities, moments for mercy, moments for forgiveness. And even opportunities to fail, because I’ve had a fair amount of failure in the last sixteen years of my life, too, that exists in prison, but exists in a radically, radically different way.

Betts and his family next to the house where Richard Wright lived in Brooklyn. (Courtesy Reginald Dwayne Betts)

SB: Last year, you gave a commencement speech at Wesleyan University that focused on time. Without rehashing the entire thing here, I was wondering if you could speak to your philosophies around time as it pertains to the gears in a mechanical watch and the profundity of that, and also how the pandemic has shifted your relationship with time.

DB: It was an essay—and this taught me that everything isn’t for everybody—I was reading this essay in The New Yorker about a guy who collects watches. And it is the most like, bougie … I thought I would hate it. But he talked about how listening to the second hand would keep him calm when he was stressed out. And he talked about how, for collectors, it’s not just about how much money you spend on the watch. It’s actually about the idiosyncrasy of the watch. And so the mechanical watch, you’ve gotta wind it. But the thing is, it’s not like a quartz; it doesn’t keep perfect time. Every day, it loses a few seconds, and it loses a few seconds because of the individualistic nature of the second hand. Sometimes it’s [makes quick swooshing sound]. And sometimes it’s [makes slow swooshing sound]. And sometimes it almost pauses a beat before it moves forward. Every few days, you’re supposed to check it and make sure that you haven’t lost [too much] time. 

I was thinking, that’s how life works, though. Sometimes you on it, and it’s going well. And sometimes, it’s just kind of funky, and you gotta check yourself, and figure out, how do you recalibrate yourself to the world? Because you can fuck around and spend six months just meandering. I learned that in prison too, because it is really stressful. And if you don’t find a way to check yourself, you can mess around and lose a year and not know it. It’s almost like being lost in a gambling spot, and not knowing you’re in the gambling spot, because you’re just in a trance. 

But the other beautiful thing about the mechanical watch is that the basics is just the minute hand, the hour hand, and the second hand. But if it tells you the month, they call it a complication. So it’s one complication. If it tells you the month and the date, that’s two complications. Then every extra feature is called a complication. And I was trying to say something about how we are trained to think about the things that challenge us in this world, the complications in our life, not as things to add to who we are, but things that detract from who we are. And I think there’s something beautiful about thinking of the complications that we confront as things that add to the substance of who we are.  Everything I’m doing right now came out of the profound complication that I created for myself by pulling a gun out on somebody. You know, you never know. One thing is whether it’s meaningful for me, and I like to think that it has been meaningful for me. I like to think and hope that it’s been meaningful for other folks, too. And so having a better understanding of what complications might mean will help you, I think, maybe. 

Then the pandemic was interesting because—I don’t know how I felt about people comparing being on lockdown to even being on lockdown. It’s like, You’re not on lockdown. You could go outside if you want. You could breathe all the Covid air in America if that’s what you choose to do, right? You’re not in prison, you know? You are taking safety precautions that are damning and challenging, but let’s remember what it is, and it’s not lockdown. 

And yet. And yet, that time period was the time I spent the most time with my family in years and years. That inability to leave as we wanted to, that need to, when we did want to leave, to find different spaces out in the air to leave to, it changed my relationship to space. It changed my relationship to work. And in fact, for me personally, I was pretty productive, I started Freedom Reads, and I’m having interviews, I’m having meetings with people in [several] Departments of Corrections who likely wouldn’t have been as functional with Zoom and Microsoft Meets, because most of our work didn’t necessitate those kinds of cross-country interactions. And if you just have a local job, why would you be functional with Microsoft Meets or Zoom or Skype? But all of a sudden, we’re all forced to think about what it means to work remotely.

Now I’m able to have meetings, and I’m able to push a timeline, because I’m able to meet with people in the D.O.C. in Massachusetts frequently, in the context where I would just would not have been able to. It would’ve been absurd to suggest it. “I’m going to meet you on what? On Zoom?” That is not a secure line. It would’ve made no sense. Suddenly, I was in a world where this made sense, and I was able to jump-start a bunch of communications that led us to build these libraries in these prisons. More personally, I did a whole play, and I was able to workshop a play and get it to where it looked like it might rock, by doing it via Zoom. I mean, I was absurdly… I wrote the Kamala Harris piece [for The New York Times Magazine]. Damn, I had a pretty productive time…. 


SB: I know, I felt like I had a lot of homework to do to prep for this. [Laughs

Could you speak to the 1990s in particular, and how that particular moment in time—and the date of your sentencing, May 16, 1997—is relevant in the context of time? Because I feel like if the same thing were to happen right now, it would probably be a different conversation. So I’m curious how you view the ’90s, looking back?

DB: I graduated on like May 16, years and years after 1997. I was the commencement speaker at the University of Maryland. I remember, actually, when I gave that commencement speech—mind you, I’m just walking down the hallway and I see this advertisement that says, “If you have over a 3.5 GPA, you could apply to be the commencement speaker.” And I was like, “Shiiit. I’m going to apply for this.” I just had to write the essay. You wrote the speech out and they chose you. I wrote the speech, and one of the lines was, “When I got sentenced to nine years in prison at 16 years old, nearly to this day, no one in that room would’ve imagined that I would be here given a commencement speech before my peers, before our families, before my mother, my wife, my children—actually, my son.” You could see the people in the front row talking, like [whispers], “Did he just say he was in prison?” “I think so.” “No, he couldn’t have said that.” And I was beside the head of the C.I.A. Panetta?

SB: Leon Panetta.

DB: I was beside him. He was the main commencement speaker. So it was like the convict and the C.I.A. dude, you know? And it was just—

SB: Who’d probably spent some time in the Pentagon. [Laughs]

DB: Yeah, I know. A complicated job he had, I think, to say the least. But the point I was trying to make then is like, in 1997, nobody would’ve expected this. In 1997, you’re talking about the era of the superpredator. 1996 is when I got incarcerated; John DiLulio’s piece comes out [in The Weekly Standard] in 1995. And so this notion….  Even popular culture: Menace II Society, Boyz n the Hood, the sort of films that depicted a kind of Black urban masculinity, and gave it an outsize weight to how Black boys and young Black men were treated. You’re talking about the corridor, the New Jersey Turnpike, and the war on drugs, and what is it, like, ’96, Bill Clinton, the drug laws, ’94. But then you’ve got the Prison Litigation Reform Act, and you’ve got HIPPA. All of this is a moment where the one thing that you have bipartisan support on is to lock people up for longer periods of time, and to make it more harder for them to get in court once they’ve been locked up. And to make it more challenging for them to challenge their sentences, or challenge prison conditions. This is all ’94, ’95, ’96. This is all, we need to take them, and bring them to heel. 

One of the real challenges is to imagine how President Biden has been able to, in some way, exist as a president in a really, really reformist era without actually reforming anything. I still don’t think that they’ve appointed a person to run the Pardon Office in the federal government. We still don’t have federal parole. We still haven’t really actively used the clemency power. There’s still not a use of the bully pulpit to encourage that to go into other states.

And more importantly, maybe, there’s still not a really robust conversation about how to think about reform. When we have crime rates rising in some cities, in some states, what we’ve done is ignored it. You still have Virginia, which is in many ways a national disgrace in terms of parole. The parole system in Virginia is already really complex. It’s already really opaque. Instead of thinking about how to reform that system, so that we let people who deserve to be free go free, what they did last time was demonized, in the last gubernatorial race, is they demonized the prior parole board that was making their best efforts to make the system more equitable. And they was doing so where they only had like a twelve or thirteen percent parole grant rate. It’s not as if they were letting eighty percent of the people go. They needed to still do far more work. Instead of thinking about what it looked like to reform the system, what it looked like to keep victims more engaged, they demonized it. 

So what you have is, in some places in this country, 1996 is still actually the time. And I think that is what I think about when I think about that date, because you have a lot of places in this country, and a lot of people, who talk as if we are in a different space, but don’t fundamentally believe it. Because, if I carjack somebody right now, depending on where I lived, the same thing would likely happen. And in fact, you know the same thing would likely happen, because there’s a lot of people who are in prison now, still, for crimes they committed as children in the nineties, and they can’t get relief, and they can’t get mercy. Even when they’ve got impeccable prison records. Even when they’ve been trying to be mentors, and when they’ve been trying to educate themselves and rehabilitate themselves, facing a life sentence. You still don’t have a national conversation about what it means to let these people go. 

I hope that we push that, and we find a way to make that happen, particularly in places where friends of mine are incarcerated, like Virginia. Because I do think there’s room, and I do think there’s room to do so without endangering public safety, and to do so without disrespecting the real weight, the real tragedy, that a lot of families have to deal with and live with every day. I think a lot of us understand what that means. And even with understanding what that means, we believe people should have second chances, and third chances, and that our money is better spent on something else besides keeping people in cages.

SB: I wanted to bring up 2005, as well, and your thoughts in relation to your release at age 24, and to the date March 4, 2005, specifically.

DB: On March 4th. I came home on March 4th, and it’s the only date that’s both a date on a calendar and a command. The strange thing about it—I say it a lot now—is I came home, and I imagined that I was going to leave prison behind me. I was 24, and while I had experienced incarceration, I hadn’t experienced freedom. I didn’t know the kind of albatross that a felony conviction would be. And I also didn’t know, even when it wasn’t an albatross—in the sense of, even if it didn’t lead to collateral consequences—it was just something that I had to deal with. 

Like, even if you didn’t see it, and me and you were friends, and you’re like, “Yeah, so, I remember when I first got to college….” And I am 24, so a lot of my peers—and I’m relatively intelligent and I’m trying to hang around smart people—most of them went to college. And they’re actually in the workforce now, and I’m working a minimum-wage job. Their point of references are when they were 18, 19, 20, 21. All of those years are marked by things like the release of The Roots album. Well, that’s not the same thing as the first time that you drove your own car, or it’s not the same thing as moving into your college dorm. I was tracking years by the release of music when you was tracking years by going to those concerts. What do you feel in that space of absence beyond the truth? And so, March 4th was both the day I came home and the day I realized that you actually never really come home, or you do come home, but you carry prison around with you. At least I do. I don’t know if everybody does. I don’t want to sound melodramatic like, “Everybody does.” But I have been incapable of letting it go. It’s like a grudge I hold.

SB: And that same day, your mother also told you something she held back from telling you while in prison, that she had been raped at gunpoint by a stranger just weeks after your arrest. You wrote really eloquently about this in that Kamala Harris essay in The New York Times Magazine, and also spoke about it during an interview with her on the Death, Sex & Money podcast. I was wondering if you could talk here about how this conversation with your mom and her experiences altered your perspective around imprisonment, and around what it means to do time?

DB: You’ve got to understand that when she told me I had just came home. [Pauses] I’m not going to act like this is the first person I knew to get raped. Doing time in prison as a kid, it’s a thing. I had family members who wrote me when I was in prison and told me things that happened to them. So it’s not like I was oblivious to the world I lived in. But still. And I thought, What did it mean for my mom to carry that with her for all that time, and just not tell me to protect me? To be like, “I don’t know how he’s going to deal with this.” It kind of fucked me up. 

I was 24, but I did eight years in prison, and so in some real ways, I hadn’t actually had…. I had intimate conversations with people in prison, but I was still, in a lot of ways a kid. It’s a difference between being 24 in prison and being 35 in prison. Even if you went in when you were 16, it’s a difference in terms of how you accumulate loss, and how you process loss, and what it means to know that your uncle died and you couldn’t go to the funeral, and your cousin died and you couldn’t to the funeral. And some of your peers are getting sick. I was in prison, and everybody looked like they could run a marathon. My people looked like they was going to live forever, which is not the case today. When me and my friends talk now, it is different. It is weighted with the reality that this shit might not work out for us. 

And so, when my mom tells me that, she’s telling somebody that’s just not…. There’s a cohort of men who have state numbers—that includes the person that assaulted my mom and me. It was like, This is like a fucked-up fraternity. And then we didn’t talk about it again for ten years because, you know, how? We have no language for it. And the podcast people said, “I heard you talk about your mom before, and I think it’s quite lovely. And I think it’ll be great to have you guys in conversation with each other.” I was like, “My mom don’t want to be in a podcast.” And I was like, “I’ll ask her, though.” And I asked her, and she’s like, “How do we prepare for this?” I was like, “You don’t prepare for a podcast!” [Laughs] I prepared for this one. But I was like, “We just show up.” 

And honestly, I actually don’t really prepare for interviews because, one, I think if you prepare too much…. Like, I think politicians have to be, and this is the only direct example, so the politicians and artists or whatever. If you prepare too much, then all you have is talking points, and it’s boring for you, it’s boring for the interviewer. And maybe if you’re not practiced enough, you don’t feel comfortable. But I was like, “Ma, who knows, let’s just do it.” “What are we going to talk about?” “It’s just going to be about me, really.” Little did I know. Then what happens though is, my mom is actually good, the best interviewee. The interviewer says, “So, what was going through your head when your son was facing life in prison and going to court?” And my mom answered the question she wanted to answer, or she answered in a way that she wanted to. She was like, “It was rough, because at the same time I was going to court for him, hoping that he didn’t go to prison, I was going to court for the man that assaulted me.” I was like, “What?!” It ain’t that I couldn’t believe it, but I was just like…. 

The thing I learned—of the many things I learned—was that silence is a burden, and she was really brave. It was like, “We going to talk about it, and we going to talk about it here, for whoever the listeners are of this podcast.” Maybe we just going to talk about it for us, honestly, because like, I didn’t care who heard the podcast, and I didn’t know who was going to hear it. Then after that I was like, “Do you mind if I write about it?” Because I thought that part of what I was hearing in the conversation was like, for both of us, it was the hardest thing. I just didn’t know how to confront it. To me, writing has always been about learning and about figuring things out. And I was trying to write the Harris piece, and I don’t really write profiles of other people. It’s just like, I’m not that writer. I like to write about—it sounds arrogant as hell—but I like to write about myself. I think about myself as like—

SB: You did write a great obituary of sorts for Michael K. Williams.

DB: Well, yeah. I really wanted to write that though. But even in that one, some of the stuff in that came out of a conversation that me and him had. So what was great, and the reason why… It’s like this intersection between our lives.

And so the Harris piece, what I was able to do is [have] my mom become the stand in for…. That was my intimate connection to Harris. I couldn’t write purely about Harris as a political candidate, because I just find that I’m not that kind of writer. But to understand who she was—I wrote about her in the context of these women that I knew, and the ways in which they had dealt with the world, and the ways in which they had dealt with violence that men had inflicted on them. Men that they didn’t know and men that they knew. And I tried to throw some stuff in there about the people I represent, because there are families that likely feel the same way about them, and whether or not they should be free, that I’ve grappled with thinking about this person who assaulted my mom. 

So yeah, I don’t know, man. It’s a lot. It’s one of those things that I think you don’t stop processing. It’s a brutal, brutal, brutal, brutal country we live in, for a lot of people. That is the hard question: How do you square that brutality that we sometimes inflict on people we love, or people we don’t know at all, with the brutality that the system inflicts on others in our name? And even, How do you square the fact that sometimes we want it?

SB: I wanted to get into your reading history and your relationship with books. When did that begin? Do you remember some of the first books that had an impact on you prior to your time in jail and prison?

DB: Oh, I do. But I’m going to say this thing about Michael K. Williams before I forget.

SB: [Laughs] Sure.

DB: The reason why I wanted to write about Michael K. Williams is because, like…. [Pauses] We could be a lot of things in the world where we are alive, and most people won’t even know. And then it’s a way in which you just get remembered for what people think about the way you died. And I had talked to him, man, and he was just so filled with sort of…. He was charming, and polite. And that’s rare. 

Also, though, he went—talking about hard questions—he went to the well again and again and again, to think about how to portray people who a lot of us don’t love. And I think that’s a deep challenge. Especially when the roles challenged him, and the ways in which those roles challenged him. I think it wasn’t always addiction, as some people might think. I think sometimes they challenged him because he was confronted with the history of this country, and he didn’t know what to do with it. 

I remember I heard something about one time he first had a relapse. It was because of 9/11, and from his rooftop, he could see and smell burning flesh. The story that you hear about somebody like that isn’t like, “Yo, this dude is a patriot. This dude loves his country. This dude loves his community.” And to see it broken hurt him, and that brokenness wasn’t just his neighborhood, but it was also the broader New York and this other idea of what it means to be a part of whatever this thing is that we’re a part of. How do you tell that story about somebody else without reducing them to—

SB: The complexity of Omar in The Wire.

DB: Yeah. So, anyway, that’s why I really wanted to write that piece. And I don’t know if I got in everything I wanted to, but I tried. And then your question was….

SB: Your reading history. And I’m thinking here, prior to your time in jail and prison, were there books in your childhood that stood out to you?

DB: So I did one internet search before I got locked up. And I searched “speed-reading.” 


One of the last books I checked out from the library and never returned was Evelyn Wood’s guide to speed-reading. And that shit don’t even work. One of my homeboys swears it works, but I’m like, “It just doesn’t. It doesn’t.” I used to watch these infomercials that would be like, “Example: How many guitars are on the wall? And you don’t go ‘One, two.’ You just see the two guitars and you know, it’s the same thing when you look at words. How do you group….?” It doesn’t work. 

It’s funny, though, the last book that I read in school was The Scarlet Letter. I don’t remember reading a lot of books for school. I don’t feel like—my child, my kid, my oldest, at least, he reads a lot of books for school. He had Ted Hughes. I was like, “You’re reading Ted Hughes?” He was like, “Yeah, this is for class.” [Laughs] I was like, “This is so much privilege right here.” Right? I’ve got a picture of my childhood bedroom, and I don’t have any books around. And I realized that I read a lot, but we just didn’t have money to be buying books. If I took a picture of my kids’ bedroom, you’d be like, “Dude is a reader.” It warms my heart up. He got books falling all over the place. 

I read Things Fall Apart. That was also one of the last joints I read. I always read the new Walter Mosley, a lot of Shakespeare. And I had this book of philosophy. I don’t know who wrote it, but it was about, like, on being. It was asking these philosophical questions like, “How do you know you exist? Absent a mirror, how do you exist?” But I’ve read a lot of stuff, man. Not as much as I did when I was in prison, I think. One of the last books I read, too, was Baldwin, I have read, what was that joint, Giovanni’s Place?

SB: Giovanni’s Room?

DB: Giovanni’s Room. I had read that. But I had a friend whose mom went to college, and I thought that the books that she had read was the conduit for college, so I would just take books and borrow them, and read them, and it was kind of happenstance.

SB: Reading your memoir is interesting. I was reading between the lines, and it was almost like a primer for the works that shaped you. You have Baldwin’s Going to Meet the Man; Frantz Fanon’s Black Skin, White Masks, Sonia Sanchez’s Under a Soprano Sky, Michael Harper’s anthology Every Shut Eye Ain’t Asleep, Sun Tzu’s The Art of War, Toni Morrison’s, The Bluest Eye, Asha Bandele’s The Prisoner’s Wife, the poems of Yusef Komunyakaa, Dickens’s Great Expectations and Oliver Twist

DB: Yeah. This is the thing, though. When I was inside, I got to curate reading habit in a way that was more…. I read Derrick Bell when I was a kid, too, though. I read him when I was a kid, randomly. It was some book that my mom picked up on the, like, bargain book table. I remembered that space alien short story, [The Space Traders]. When I was in prison, I was listening to Black Star [the song “Astronomy (8th Light)”; it was like, “Black like faces at the bottom of the well/I’ve been there before.” And I was like, What? I think I know what that is. And so sometimes I would get books from songs, and then they would hip me to the fact that I read these things. 

I got my high school diploma when I was 16. I tell people I skipped twelfth grade and went to prison. Because when I was in eleventh grade and I went to the jail, and she was likeI was trying to get a G.E.D.—and she asked me what classes I was taking in high school. And I was like, “French IV, physics, Intro to C++.” It was the first time that I could feel good about myself, really. She was like, “You taking the same classes my son is taking.” And then she found out that, because I’ve been taking these advanced math classes, all I needed to get a diploma in Virginia was to finish eleventh grade and take twelfth-grade English. So I finished eleventh grade on my own, and she gave me twelfth-grade English, and basically was like, “Read books.” 

I remember reading Sophie’s World—no, I remember reading Sophie’s Choice. I asked her to get me Sophie’s World, which was a philosophy book that I had wanted to read before I got locked up, and it was an intro to world philosophy through this lens of this little girl who meets all these philosophers. She says, “Yeah, I think you’re mistaken, Dwayne. I don’t think there’s such a thing as Sophie’s World. But I’ve got Sophie’s Choice.” [Laughs] So I’m reading it, and I’m like, “Damn.”

Then from that, I read Nat Turner, and that’s how I found out who Nat Turner was. It’s interesting. I do think there’s a way in which books shaped my intellect. But also, books shaped my relationship with the world and with these people around me, because I still know the dude that gave me the first Frantz Fanon book I read. It was this cat that was at the jail, and he was like, “You should read this. You seem like you like books.” And I was in no way prepared to read [Black Skin, White Masks]. No way. But reading above my age level and my intellect prepared me to read The Wretched Of The Earth. How do you pronounce W-E-B-E-R in German? The Weber cat.

SB: Weber.

DB: Yeah. But I’ve read him, and apparently that’s not his name. And I was telling somebody, he was like, “You mean Weber,” or whatever it is in German. I was like, “Whatever, man. I read it in prison.” I read it when I was way too young to understand it, but all of those things—it was about work ethic—but all of those things helped me, I think, shape something of who I am.

SB: And you’ve also written about Lucille Clifton, and noted that her poems “let me imagine even the wildest dudes around me as my brother.” There’s this incredible moment when, years out of prison, you met Lucille Clifton. I was wondering if you could share that moment, and just her work, what it means to you?

DB: One of the first poems was “Cutting Greens,” and it’s talking about cutting the collard greens, and how the greens become black against the blade. It ends, like, “I sense the bond of living things everywhere.” And in another poem [“Won’t You Celebrate With Me”], that everybody quotes, it’s like, “Come celebrate/with me that everyday/something has tried to kill me/and has failed.” I read her poems, and they were these concise wonders. And also, they were critical. There was this one poem called [“My Poem”]. It has this line: “mine already is/an afrikan name.” She’s talking about Lucille. And you could tell that she’s writing within the Black Arts Movement, when everybody’s suggesting that you got a slave name. And she’s like, “I’m named after my grandmother. And my grandmother shot somebody who was going to come and assault her family from her horse. I am not named after a slave.” Right? You could feel it in the poems. And the poems were richly complex in a way in which my world wasn’t at the time. Or maybe my world was richly complex even then, but my world was filled with the secrets of the men around me.

SB: It was hard to see it.

DB: Yeah. I was young, too. And so, her poems were just really rich. 

I remember coming home, and I was at this workshop, Cave Canem. It’s an organization, a Black arts organization, a poets organization. They have this retreat every summer, where fifty-four Black poets get together. And you meet Elizabeth Alexander [the guest on Ep. 52], you meet Rita Dove, you meet Lucille Clifton. For a Black kid who had been in prison, these people were like superheroes to me. 

The dope thing about The Roots—I keep coming back to them because I’m writing about them—but I read [Chinua Achebe’s] Things Fall Apart before I get locked up. And then in 1999, their album is called Things Fall Apart. Then years later, when Phrenology comes out, Amiri Baraka is on Phrenology. So all of a sudden, they become the band that connects my pre-prison identity that I was developing nascently as a reader, as a thinker, to also the sensibility I was developing as an artist in prison. It’s wild because you don’t expect—and it is in some way condescending to the culture to say this—but you don’t expect one band to encapsulate that, and throw in [Malcolm Gladwell’s] Tipping Point, also. And I’m like, “I read that.” You don’t expect one band to do all of these things that’s reflecting your developing sensibilities. 

But anyway, I’m at this workshop, and I hear about it when I’m in prison. It’s Callaloo, and it’s Cave Canem, and I hear about both of them in prison. I apply to Cave Canem soon as I come home. I missed the first summer because I missed the cutoff, so I applied for the next summer. And I go, and Lucille Clifton comes in to give a talk one morning, and I usually sit in the front. Everybody there has a college degree, except me and my [friend Jamaal May], if memory serves me correctly. I’m in community college, and I think he had graduated from community college, maybe. You kind of feel the weight of being in a place like that. Because honestly, this is like summer camp for writers. But it’s hard to have spent so much time in prison, and not feel like I had wasted my life without even understanding the possibility of this. So it’s a bit frustrating, but I’m there, and I’m enjoying it. I’m in the zone. You be like, “You’ve found your people.” 

I asked her a question. She answered the question. And I asked a question about “The Lost Baby Poem.” I asked her if it was patterned after the Psalms, because it was like, “if I ever forget your brothers or sisters/let the ocean take me as a spiller/of seas        let black men forget my name forever.” [Editor’s note: The exact lines are “if i am ever less than a mountain/for your definite brothers and sisters/let the rivers pour over my head/let the sea take me for a spiller/of seas let black men call me stranger/always        for your never named sake.” And there’s “I might have to let my tongue cling to the roof of my mouth” and “let my right hand forget its skill.” [Editor’s note: The lines in reference, from Psalm 137:5–6, are “If I forget you, O Jerusalem,/let my right hand forget its skill!/Let my tongue stick to the roof of my mouth,/if I do not remember you.”] So there’s something out of that, and I thought so, and I asked her, and I was trying to say the sonnet. And then she repeats the sonnet from memory. 

You’re supposed to just ask one question, to be respectful, it’s fifty people in here. I look around. I ask another question. And I ask another question. I ask like seven questions. And I’m not even taking up space, actually. Everybody around me was super gracious, and it was almost like it was a thing that was happening, it was just me talking to her. And I’m not a shy person, but I also never really had an intimate conversation with her, besides that. But my wife knew, Terese knew, how important she was to me. I remember once she got me, she was like, “Yo, Lucille Clifton’s reading at my college. I got tickets for you and Micah. You guys should go.” And I got this picture with me, her and Micah when Micah was a kid. 

But anyway, after these questions, I went back to my room. We were staying on the college campus, and it was the first time I’d been on the college campus. I still remember the other three dudes that was staying in the quad with me. I come out, and I’m weeping, and I hadn’t really broke down in a long time. It was a moment. 

The thing is—and again, I ain’t saying I ever had a real conversation with her—but the thing is, when you a writer, and sometimes people come up to you and they say shit, it gets exhausting. But what I learned in that moment is that if you’re lucky enough to mean that to anybody—and most of us do things in this life that have no chance of meaning that to anybody, and that doesn’t change the value of what it is that we do—but I’m just saying, if you’re lucky enough to love doing something that has that possibility, it’s real. 

I remember Rita Dove came that same summer, and stayed up with us. She’s a night owl. She’s like, “I do my talk at night because I don’t be doing that daytime stuff.” It was me and six poets up to three o’clock in the morning talking to Rita Dove. You don’t get a chance to do that, the second Black poet to win a Pulitzer Prize. An esteemed writer, a phenomenal writer. Her new book [Playlist for the Apocalypse] is really amazing. I carry these lines around in my head. There’s this line she had: “If you can’t be free, be a mystery.” You just carry it around with you. All of these words just give you different meanings. 

Sonia Sanchez, I ran one of her poems in The New York Times. She sends me an email that’s like, “Call me, brother. Thank you for running the poem.” And I’m like, “This is somebody spamming me. I’m not responding to this!” Then I get another email an hour later. It’s nine o’clock at night. The honest truth is at first, when I got the first one, I was like, “I’m going to call, but I think this might not be real.” And then I got another one at nine o’clock, I was like, “All right, I’m calling right now.” And [she’s] just like the warmest person. I think what happens is, we live in a moment that has, like, all of this increased accessibility for so many people in terms of we’ve got the internet, we’ve got this, we’ve got that. But what we don’t have, I think, or what we don’t often get a chance to nurture, is what it means to…. I would not trade the hours of conversation I had with Sonia Sanchez over the last year for anything. Or with Afaa Weaver, or just these folks that I came up with writing, and that moment with Lucille Clifton. 

It’s interesting, because I am grateful for anybody who has that kind of opportunity, because it is something different. For me, it was different, too, because I didn’t read these folks in school. This was all self-discovery. And I bought their books, making twenty-three cents an hour. It’s like, “Yo, I worked a hundred hours for your book!” 

SB: [Laughs]

DB: I don’t care what they say. They might say that they love you, but let me see them clean toilets for a hundred hours to buy your book of poems. Then they could come. We’re talking about fan of the year. It’s like, I won. I scrubbed toilets to get Under a Soprano Sky

SB: [Laughs] After you’re released from prison, you worked at a paint store. You, as you mentioned, attended community college, received a bachelor’s degree from University of Maryland, earned an M.F.A. from Warren Wilson College, eventually graduated from Yale Law School in 2016. You’ve written a memoir [A Question of Freedom], three books of poetry: Shahid Reads His Own Palm, Bastards of the Reagan Era, and Felon. There’s so much to be said about this post-prison experience. But I was wondering if you could speak to these seventeen years in terms of what the first eight were like, and what the most recent eight were like?

DB: Yeah. I think the first eight, I was kind of.… I had a bunch of expectations: A Question of Freedom was going to get me on Oprah, and make me an internationally world-renowned writer. Did not happen. It was going to allow me to pay my bills. It did not happen. [Laughs] But it did a lot of stuff, though. But still. I remember trying to get a job, that first book of poems. I had two books out before I turned 30, and I thought I was guaranteed to get a job, some entry-level poetry job. But I didn’t have a family support figure that’d be rocking, you know. Cool. 

I remember the hail mary. I applied for a Radcliffe Fellowship, and I got it. I was scrambling and I had a college degree. I had three degrees: I had an associate’s, a bachelor’s, and an M.F.A., and couldn’t get a job anywhere. And applied for the Radcliffe Fellowship and got that, and was there, still applying for jobs, and couldn’t get a bite at the apple from anyone. I couldn’t even get an interview. I felt like the character from Invisible Man. I didn’t know who had sent my recommendation in that said to keep me running, but I knew somebody must have. 

I decided to go to law school. I just was like, If I’m going to be unemployed, I’d rather be an unemployed lawyer than like an unemployed poet. So the last nine was really framed by that. You know, the first eight was framed by this experience of trying to… [Pauses] Trying to work within the constraints of the world that I thought existed. And then the last nine was framed by like, What does it mean if I invent my own way? That started with going to law school. And then I wrote Bastards of the Reagan Era, which, even the title, everybody was like, “Nobody’s going to review this book, probably because the title has ‘bastards’ in it.” And I was like, “I’m going to write what I want. I’m about to be a lawyer, I’m in Yale. I can write what I want and not be afraid to offend anybody.” And it was cool. I thought I was going to be a public defender. Then I decided I didn’t want to be a public defender, because it’s really hard to watch somebody go to prison. 

There’s so many people who are in now that need representation. I got to help somebody get out working on their parole application who did thirty-five years, and he had got locked up when he was 16. So I ended up doing that, and I’ve been doing that, and, I don’t know. 

The last eight have been about inventing what I want the space to look like for myself, and actually being able to try some new things. I write for The New York Times Magazine. I never imagined writing for The New York Times Magazine, or even writing a long piece like that. Like the first one that I wrote, about myself, it wasn’t in my conceptualization of who I am, and to writet that and have it win a National Magazine Award was pretty dope. And then I’m following a presidential candidate on the road. 

The last nine, I have had, in a lot of ways.… Even my prison experience was charmed. I was safe. I had friends. I think most of the people I did time with respect me. I think even in prison, I was loved by people. And definitely, both the first eight years reflect that, but even in the last nine—because in the last nine, it was me interested in radically different spaces, and spaces which I have been successful in. But it’s not as if my priors predicted that success. So people had to have a lot of faith in me being able to accomplish what I was hinting at being able to accomplish. And it’s been cool. 

For the last five years, I’ve coached my children. I’ve coached the boys playing basketball for five years in a row. It’s different. I lead a different existence as an adult, too, in terms of being a member of the community. Even when I wasn’t really stable, financially, or anything like that. But I was still a member of the community. It doesn’t require financial stability to be a member of the community. And so even when I was struggling to become a lawyer, and “are they going to let me practice?” I was coaching, though. When I was a federal law clerk, I was going to Philly, midnight, every Monday, I was getting on a train, getting to Philly at 5 a.m., going to work, and then coming back to coach on the weekend. So, yeah, I think that the two are interesting, because I almost feel like the first half set me up for the last half. And it’s a real question about what will the next eight years, ten years look like? I have no idea.

SB: I feel like we’re in this sort of renaissance for prison writing. And I wanted to bring that up. And by that, I mean writing about prison, writing while in prison, or both. And there’s the path-breaking work of your friend, the prison journalist John J. Lennon; there’s Mitchell S. Jackson and his incredible book, Survival Math.

DB: He just won a Pulitzer Prize.

SB: Yeah. There’s the former mafia insider Louis Ferrante and his book Unlocked, from a little over a decade ago. A new book on the subject, The Sentences That Create Us, just came out, for which you wrote the foreword. It seems like this book represents this trajectory, this moment, this, I guess past twenty years in prison writing, prison literature. I’m wondering how you view the landscape in comparison now to then, and what this moment means.

DB: It’s interesting, because you still had Chester Himes; and you still had Claude Brown, Manchild in The Promised Land; and you had Malcolm X; and you had Albert Sample and you had Nathan McCall. You had Wesley Brown, who wrote Tragic Magic. His prison experience was different, because he had declined to go to Vietnam, and he did three years for that. And then Asha Bandele [and her book The Prisoner’s Wife], which I think is adjacent, in a way. It’s always actually been heavily weighted towards men who’ve been incarcerated, and that’s something that we still struggle with. There’s a Native American woman [Louise K. Waakaa’igan] that just won a poetry prize, just had a book come out, that I think is a part of this new renaissance. She was in the Minnesota Prison Writing Workshop that allowed her to develop some of those chops.

Cherry, the novel by that cat [Nico Walker]. It’s another guy [Curtis Dawkins] that wrote The Graybar Hotel, who’s locked up—his book came out. So I think there’s a way to say it is a renaissance right now. Even books you didn’t mention, Wilbert Rideau’s book [In the Place of Justice], Randall Horton has multiple books, at least five books, out. These are all people who are both writing and award-winning writers. Susan Burton. What’s interesting is you have people straddling the line between writer in the classic mode of, “This is what we do,” to also people who have just been able to find a way to tell their story, and find value in telling their story, and having their story frame some of the conversations about incarceration. 

And I think The Sentences That [Create] Us, what’s actually special about that is, it takes the life of somebody like John Lennon, who is doing fantastic work while incarcerated. I have no idea how…. I understand how he manages time, but the audacity that he has had to send to places like The Atlantic, and then for him to learn how to write sentences well, take editing well, but deal with that sense of self that’s always being diminished a little bit by still being in prison, and letting his writing be a public occasion for reflection on the prison, on his self, on his crime. That’s impressive. And what the book does, I think, is give other people who are in prison, trying to think about being a writer, the tools to frame out how you do it. 

Luis Rodriguez. It’s a lot of folks. Shaka Senghor. Actually, in a real way, I will say there’s a renaissance of writers who have come out of prison, in the same way that there’s a renaissance of writers who have come out of war. I think about myself in conjunction with Elliot Woods, who’s also a fantastic writer. Phil Klay. And thinking about the tradition that they’re part of. So I think what happens though, and I think one of the things I might caution against, is the way we frame these writers as being a product of their experiences. Because in the same way that Elie Wiesel, or, man… I love this guy, he wrote…. Not [Vikor] Frankl. I’m not going to remember it. I’m mad, too, because his book is beautiful, and I think so introspective, and I’m mad I can’t think of it. 

But anyway, you’ve got this pantheon of these Jewish writers who came out of the Holocaust and then you got another pantheon of war writers. The Things They Carried. But what happens is, those writers get defined by their experience, as if they came out of their experience, but I think it might be the other way around. It was something in them that pushed them to be a writer, and their experience was the thing that fueled them. 

And, I should say, because in both of those contexts, you see that it’s heavily weighted towards men who are doing the writing. And I think in both of those contexts, it’s been the men who’ve had the resources. So when you think about it in the prison context, there’s always more programming happening in the men’s prisons than the women’s prisons. You think about the war context, maybe that’s better, because nobody should be on the front line. But I think the experiences that drove people, the hellacious experiences that drove people who were inclined to do it anyway, deep into their soul, to figure out what it means to make meaning of the world that they’ve experienced, has largely been men. 

I do think it’s a renaissance. There’s a lot of us. We’re so different, too. You can’t find two more different writers, I think, than me and Mitchell. Because he just is far more braver with language, in some ways, than I’ll be on the page. But I think we both get at it, though. I think the same thing is probably said of John, and actually he’s more a reporter, a legit reporter, than frankly I’ll ever be. I be asking people questions and doodling. Nah, no, I don’t. [Laughs].

SB: I wanted to mention or bring up Freedom Reads, which you started in June 2020 as the Million Book Project with the Mellon Foundation and Yale Law School. The project aims to build these Freedom Libraries inside a thousand prisons and juvenile detention centers across the country. What are your hopes and aims for this? And I guess, some of the long-term, across-time impacts that you imagine it could result in?

DB: First, if beauty is justice—and this is one of the things that MASS Design Group [whose founding principal, Michael Murphy, was the guest on Ep. 57 of Time Sensitive] deeply believes—if beauty is justice, then we have to pay attention to places in which we actively deprive people of beauty. The second point, and the pandemic has taught us this more than anything else, is you never know when prisons will not be able to make books accessible to people. What I wanted to do is create these micro-libraries that existed in the housing units. One would fit in this room, and the room would still be spacious. You’re talking about, it could be as much as ten by eighteen feet of space, it could be half of that, it could be one module. Each module holds about a hundred and fifty books. Two people could browse a module at a time. So it’s not just a bookshelf. I believe in bookshelves, but bookshelves don’t build community. What builds community is when you could go and you’re both browsing books at the same time and you could see the person that’s looking at books. 

So we set these up, and we built the first one in MCI-Norfolk, the prison where Malcolm X did time. We built two additional ones in Massachusetts prisons. We got some more coming to Massachusetts. We would’ve been at Angola in September, if not for Covid. We’re looking to go in February. And we’re expanding. 

It’s both a local project and a national project. It’s a local project because we get writers within the communities where these prisons are, within the states where these prisons are, to come in and give talks. I did eight years in prison—ask me who I never saw once. No writer. No writer, who talks about…. And now since I’ve been free, and I’ve been in dozens of prisons across the country, most of those prisons I’ve been in have never seen a writer. They’ve never had somebody come through to give them a reading. I have been paid to go to community colleges and colleges all over this country. And I’ve frequently gone to prisons, right? But I’ve been paid to go into these spaces all over this country, and there’s always a prison nearby, and I would be the one person that’s asked to go to the prison. 

What we’re doing with Freedom Reads is trying to make this part of the existence of being inside, because the reason why our prisons look the way they look, I think part of the reason, is that we can ignore them. We talk about writers in prison. We should also be talking about writers who write about prison, who write about the conditions of prison, who write about the environment of prison, who write about what we expect and shouldn’t expect in terms of outcomes, based on what they see. That’s part of it. 

And I think the last part of it is just purely making an argument. Freedom begins with a book. I think that books profoundly transformed my life. I was lucky that I was foolish enough to spend my twenty-three cents an hour on books. I was also lucky that somebody slid The Black Poets under my cell [door]. I was also lucky that when I got to Red Onion State Prison, this older cat took a liking to me—he was like, “I think you’d like this book,” and gave me Every Shut Eye Ain’t Asleep to read. That’s what introduced me to Yusef Komunyakaa and to Rita Dove, because they weren’t in The Black Poets. And also that’s what gave me the biographies of these folks. 

From Every Shut Eye Ain’t Asleep, that’s how I found that Etheridge Knight had did time in prison, and that’s what made me like, “Hell, I could do this. This could be my thing. I could be a writer.” And it wasn’t because I thought it would lead to anything that I’ve done in my life. It was because I thought it would make me somebody, it would allow me to become somebody. And so, by putting these Freedom Libraries in the spaces where people live, the idea is that it’ll be a conduit to becoming.

SB: Speaking of beauty, I did want to mention this tattoo that you—

DB: [Laughs] You did do research for this joint.

SB: It’s a depiction of the artist Anselm Kiefer’s work “The Language of the Birds.” And I was wondering, when did you get this tattoo? Why did you get this tattoo? It’s your first, and from what I’ve been able to gather, only tattoo.

DB: No, I have three now. [Laughs

SB: Oh, you have more now.

DB: I have another Kiefer piece.

SB: Okay. But I did learn that it took twenty hours over three days to get inked.

DB: Twenty-three, twenty-five.

SB: So tell me about that. What was this decision?

DB: What happened is, I maybe saw the image on Facebook and became obsessed with it. And then I went to my friend’s wedding, and it was in Miami, and we went to the [Margulies Collection] Warehouse, a gallery, because I heard the Kiefer piece might be there. And it was in a space about as big as this room. It’s just a stack of books, and it’s all iron and wood. It feels ancient. And it raises this question about, What can the knowledge held in these books do? And it wasn’t even just books. It was also chairs, so it was just the whole infrastructure of reading. Then it had these giant wings shooting out the spine, out the back of the books. It’s this question, “Will the knowledge—will it give flight? Can it be true to the suggestion?” I saw it, and it felt like this is so much of the story of my life, this idea that books really, really matter deeply to me, but the tragedy and the pain and the knowledge.… You just don’t know if the wings will be enough. 

I saw it and I was like, “I’m going to get a tattoo.” Mind you, I did eight years. Hadn’t gotten a tattoo. Did twelve years. I’d been home for twelve years. Still hadn’t had a tattoo. And I searched, man. I went to three, four different tattoo artists, had to find somebody who just thought that they could transform a three-dimensional sculpture into a piece. I had them turn the spine out and put Terese, Micah, and Miles on the spine of one of the books, because they’re like the story to get me through things and—

SB: Your wife and kids.

DB: Yeah. And it hurt so bad. I’m talking about.… [Sighs] I remember I was reading Tayari Jones’s American Marriage while I was getting a tattoo, because I was leaned over, and I’ve never been in that much pain. The crazy thing is, he would be working for three hours, and I’m like, “Oh, this is finished,” and it would be a corner. And the piece covers like the top half of my back, and the wings are such so that they match on my arms, and they go down my arms, and it’s lovely. And then the second piece I got, I got a murder of crows on the inside of one of my arms. And then I got Kiefer’s “Book With Wings,” which is the logo for Freedom Reads, on the inside of my other arm. I’ve got an obsession with birds, and flight, and freedom, and… I don’t know.

SB: I’d like to close by having you read a poem you recently wrote, “Memorial Hoops.” It’s about so many things: fatherhood, having sons, being a son, being a husband.

DB: And it says the name of the book that I couldn’t think of. It’s Primo Levi’s If This Is a Man, which I found to be one of the more profound books, because it talks about this experience. It’s so complicated and it’s so rich, and there’s all of these lines that just feel like gospel, that you could just take it out, and carry it around in your head and it says something about what it means to be alive in the world. 

All right. “Memorial Hoops.” 

The day broke a record for cold, for us wanting

To be anywhere but outside, & it was late

May, the weekend we called Memorial. My mother

Is a veteran, but that is a story for another time,

& we were driving into the mother of rivers state,

My youngest son, named after two men, one who

Turned a trumpet into a prayer, the other who

Before a piano became whatever those who know say

G-d sounds like, me, & friends, who like me, imagined

Watching their sons trade baskets with strangers

Was some kind of holy. Around us was more granite

Than Black folks & I carried Primo Levi’s If This Is a Man

In my knapsack, hesitant to return to all the astonishing

Ways we make each other suffer &, still, somehow,

Survive, & astonished most by how we remember. I’ve

Forgotten my fair share of things that matter. But

Who am I kidding? The weekend was about

Basketball. We’d driven three hours to this colder

Weather. My youngest boy hoped he’d heat up once

A ball touched his hands. Did I say we named the child

After the idiosyncrasies of Jazz, all because as children

I don’t think my wife & I knew enough ambition

To save us from what we’d encounter. These were the days

When he and the nine he suited up with desired

Little more than to hear the rasp of a ball against whatever

Passed for wood in a gym with a hoop. There is something

To be said about how basketball makes men of boys and boys

Of men. The ref who chattered with us parents wondered

Why a cousin the age of the ballers ate chips for breakfast.

The other team had a player who made me think, though

She be but little she is fierce, as she, the only girl on

The court slipped a jewel into that hovering crown

We cheered, even those of us whose boys sought to dribble

& jump shot their way to the glory of a win. & when Miles

Came down as if he knew what would happen. I didn’t hold

My breath. A crossover, the ball then swung around his back,

The kid before him lost on some raft in a wild river. Maybe

He knew the ball would fall true because he turned around

To watch us as much as to get back on defense. We laughed

& laughed & watched as kids barely large enough to launch

all of that need at a target did so, again & again.

SB: Dwayne, thank you so much for coming in today. This was really a pleasure.

DB: Nah, thank you. It was a pleasure. It was fun. It was cool, man. I appreciate it.


This interview was recorded in The Slowdown’s New York City studio on January 18, 2022. The transcript has been slightly condensed and edited for clarity by our executive editor, Tiffany Jow. The episode was produced by our assistant editor, Emily Jiang; managing director, Mike Lala; and sound engineers, Pat McCusker and Johnny Simon.