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The Prison Issue

Deep Cover: What It Was Like Working as a Prison Guard at Sing Sing in the 1990s

Ted Conover discusses how little has changed in the 15 years since he infiltrated Sing Sing in order to write a book about the prison system.

Ted Conover as a guard in 1997. Photos by Jennifer Klein

This article appears in the Canadian VICE Magazine's October Prison Issue

I first read Newjack: Guarding Sing Sing, Ted Conover's account of working as a corrections officer, just as I was getting into journalism. I was instantly captivated by how much farther he'd taken the idea of immersive narrative reporting. This was more than just embedding with an army outfit or hanging around with the Hells Angels—in 1997 this guy actually got a job in Sing Sing so that he could covertly write about the prison system from the inside, all the while keeping the project secret from pretty much everyone except his family and publisher. It's easily his most recognized work amid an impressive list of books whose topics include traveling with hobos (Rolling Nowhere), embedding with undocumented Mexican migrants (Coyotes), and providing services to the wealthy of Aspen while working as a cab driver and for a catering company (Whiteout: Lost In Aspen).


Landing the Sing Sing gig was enough of a feat—one involving being tear gassed and conditioned by the intensive military-esque training process—and then there was the ten or so months he spent inside the place. As he writes in Newjack: Guarding Sing Sing, "I was like my friend who had worked the pumps at a service station: Even after she got home and took a shower, you could still smell the gasoline on her hands. Prison got into your skin, or under it. If you stayed long enough, some of it probably seeped into your soul."

In the 15 years since publishing Newjack, Conover has continued to write about prisons, recently heading to Guantánamo (his second such visit) to report on solitary confinement. VICE talked to Conover about what possessed him to embark on the assignment, how the experience affected him, and how he sees the current state of American incarceration.

VICE: I read Newjack soon after it came out and was blown away both by the story itself and the fact that you pulled it off. Can you talk a little about why you wanted to tell this story?
Ted Conover: I got interested when I moved to New York City from Colorado and noticed all the headlines about the record number of people in prison—a sense that this was uncharted territory. The War on Drugs created something unexpected, which was this giant class of people in prison. And I thought: How can I contribute to the discussion and maybe to the solution? So I went out and looked for the best books I could find about prisons, and they were all written by prisoners: Mumia Abu Jamal, George Jackson, Eldridge Cleaver, and the guy Norman Mailer helped get out: Jack Henry Abbott. Intelligent, literate prisoners had written the best books about prison. I thought, Could I become a prisoner in any meaningful way? But I didn't see any way of faking that. You either commit a crime and go to prison or you don't. I started thinking about how much prison guards must know about prison, but because they don't write about it or nobody wants to hear from them, there are almost no books.


I looked into it and first thought I would write about a family of guards, including sons and daughters and aunts and uncles. But the state wouldn't let me go to work with family members, or anyone really, in a meaningful way. They would permit me a single visit to any given prison—and this is even with an assignment front the New Yorker. So I thought that's not good enough, but that's also not right: This isn't the CIA, or something top secret. There's no justification for keeping the public out. New York is the second-largest employer after the Verizon corporation, so why shouldn't we know what goes on in there? So I felt justified in applying for a job as a CO without declaring my true intentions. And as a plus, I would be paid for this research, because I would actually be doing the job—it came with health insurance and other things. The hard part was just waiting long enough to get hired. And then once I was on the job, the hard part was just enduring and realizing that I needed to plan on staying for a year to really have something meaningful. To really take it to the next level in terms of writing something with authority that wouldn't seem like a drive-by.

Of everything you saw, which was a lot, what do you still carry with you?
That's a good question. There's just a dozen things. The one thing that just jumped into my mind right now is just a picture of a prisoner with mental problems just sitting on his bunk, rocking back and forth. This is a guy who my coworker and I were just like, he shouldn't be here, right? In the parlance of the prison, he's a bug. He's not even present mentally—why is he sitting here day after day rocking on his bunk? It was one of those moments where prison just felt deeply wrong.


But on the other hand, there's a day that the state's Online Inmate Lookup went live. I entered the numbers of some of the prisoners I'd gotten to know, including a middle-aged white guy who looked like an accountant, I figured he must have got caught up in some crazy financial scheme—that's what he'd told me, basically. But I looked him up and he was in for third-degree sodomy, which was sexual abuse of someone under—I can't remember, 13 or 14 years old. So he's a terrible child abuser.

You have revelations in both directions. You see people who have done worse things than you can imagine, and you see people who you feel sorry for. And you have to reconcile this as a human being because your job is to treat them all the same, which I must say is hard once you've learned about people's crimes—you respond in different ways to different people.

And just for a third and final image from that year, there was the night months after I quit where I was in bed watching TV, almost at midnight. And there was this prisoner who I'd gotten to know named Habib at Sing Sing, who'd transferred out to the geriatric unit of another prison. It was his third term, and he'd converted to Islam along the way. He told me he was innocent—that he'd been convicted of a rape when he was in his 60s. As a prison officer you learn to go, "Yeah, yeah," there are a lot of people who tell you they are innocent. But he had told me his lawyer was going to get him out, and then there on TV was Habib and his lawyer and Barry Scheck from the Innocence Project walking out of Greenhaven Prison, and he'd been freed on the basis of DNA evidence. There right in front of me, a guy whose punishment I took part in was innocent. It took my breath away. I was astonished that he'd been telling the truth. And then you can't help but think a little less of yourself when you didn't listen to somebody telling the truth. It's a pretty intense experience, and I'd say a fairly frightening one, too. I'm not a physically large person, and I was kind scared every day and didn't show it. And as you know from the book, it wasn't until I was out that I started having real nightmares about that fear, and being able to acknowledge it, and that took a long time to sort out. Those are some of things that have stayed with me.


The book came out 15 years ago. Did you observe any sort of anniversary, thinking back on that time?
You know, I think as with The Jungle by Upton Sinclair, the journalist goes in with a reformist agenda, right? And that book is sort of the best case scenario in terms of change coming out of it. That's when federal meat inspections got started, amid the horror of revelations from The Jungle. But… No. For whatever reason, [maybe] the American prison juggernaut is just so deeply a part of our culture and so deeply capitalized and so deeply a part of our criminal justice system that I can't point to specific reforms that my book brought about. There's just so many prison books come out every year, I think it's because educated people—publishers and readers—know we have a huge problem, and they want to talk about it and figure out how to solve it. But at times, it seems kind of intractable. I think the last few months definitely have suggested that an opportunity is coming up to change the way we do things, right? The whole awareness of the racial character of American incarceration, with Black Lives Matter and Michelle Alexander's book, The New Jim Crow, really opened people's eyes to that side of it. But the fix is not simple. Let's put it that way.

How do you see that playing out in terms of prisons and incarceration? Is that drawing attention back to the issues? As you said, the prison juggernaut is so huge that there's not often a way into it, but this could be a moment?
Yeah, I do think it's a moment to do that. I mean, I think possibly a stronger thesis than Michelle Alexander's is that prison discriminates against poor people, and the racial quality of American incarceration reflects our society broadly, with an underclass in perpetual crisis and lots of ways for people in that class to get in trouble. Perhaps because I worked in a prison with such a long history, I spent a long time reading about the period in the 19th century when the Irish were disproportionately imprisoned in New York State prisons, for example. And maybe there was national prejudice against them, but another way of looking at it is that they were poor. And poor people commit more crimes, mostly against each other. The idea that our prisons are a conspiracy that target a very specific demographic, I'm not sure I believe that. But that that demographic is disproportionately imprisoned is indisputable.


Yeah, but issues of poverty and education and access to services, which affect those populations specifically, know no racial boundaries. What were the issues you saw during your time working there and have they changed much or are they the same?
I don't think things have greatly changed. We depend, for example, on solitary confinement to a macabre extent. I mean far beyond any other nation, we are deeply committed to the supermax, to virtual entombment in metal cubes. Which we've done by building supermaxes in most states. One thing I never predicted is Newjack would give me this qualification to write about the War on Terror, but soon after 9/11, it became clear that one big result of the attack in the Twin Towers was the way we were handling people we captured. So Abu Ghraib in Iraq is one example, but the big example is Guantanamo.

A year after the first prisoners were sent there from Afghanistan, I went down there for the New York Times Magazine, and I just went again early last year in 2014 for Vanity Fair, this time to write about solitary confinement, because it's kind of like we take this article of faith that that's the best way to lock up really bad people. And with Guantanamo, we've made it worse by removing any due process around it. At least at Sing Sing, a guy would spit on a guard or stab another prisoner or be caught with a lot of heroin and would go to the box for a set period of time, maybe 90 days, maybe 24 months—that would be a long sentence. But other states have been really extreme with this: Louisiana, California, Texas, I'm pretty sure, have been keeping people in solitary indefinitely. This is being challenged in court and I think, just this week, California agreed to change some of its practices around indefinite confinement in the box. But, if anything, that part of it has gotten worse since I was a CO. Again, we are at a cultural moment where people are becoming a little more aware of this and feeling worse about it. Feeling bad about it is a problem when you work in a prison because everybody assumes, as you know from my book, you carry a stigma just by working there. That makes the job hard—knowing the rest of the world thinks you're a brute. So there are just so many ways that improving the system would help all of us.


In Canada, the argument is being made that the US is starting to move away from a system of bigger prisons and using solitary, whereas Canada has fully embraced it. But is that the case? Is the US questioning that system?
I think we are, partly because it's so expensive. It costs so much to do everything for a prisoner—and when they're in solitary, they can't do much for themselves. It's very labor intensive and the buildings are super expensive to run and build. And it just seems that local governments don't have that kind of cash to throw around these days. So that's one pressure that's making the tide turn just a little bit. And then another is that even as the American rate of incarceration peaked in 2008, I like to think that marks the swing of the pendulum, however slowly, in the other direction. In the direction of greater engagement with wrongdoers: less lock 'em up and throw away the key, less purely punitive treatment of lawbreakers, especially lawbreakers involved with drugs. It seem there's a consensus that we went overboard with mandatory sentencing and the result is this incredibly racially unfair system. I hope I'm right when I say I think that things are ever so slowly starting to move in the other direction. And I hope Canada will head there more quickly than we do.

You mentioned drugs just now, but the other part of that is of course mental health issues, and how that plays out when it comes to solitary confinement.
Right. It's like a recipe for mental dissolution, for damaging people emotionally and spiritually. It's a way to break people, and it doesn't cure anybody. If there's a cure that's being affected by long-term incarceration, it's simply that people get old and they come out with less fight in them. But that's just because they got old, not because of anything that prison did for them. As North Americans, we're supposed to be the ones still dreaming up original new idea for how to organize our societies. That's why it's so striking to me that we are so far behind industrialized countries when it comes to locking up prisoners.

Is there anything you'd have done differently? Would you approach it differently if you were to do it again?
Do I have to?

Yeah, I've got a great idea for a VICE show: Ted goes back to prison.
[Laughs] I don't have many regrets about the experience. I think I did it the right way. I think if I'd been tougher and managed to stay for two years, I think I would have written a book that was that much deeper and more impactful. And in fact, that was the complaint of a lot of senior Sing Sing officers when I published the book was, "You know, it's a good book, but you're only a newjack, so why should anyone listen to you?" I kind of think that the rookie's perspective is one of the reasons the book works, because it didn't look normal to me—it all looked kind of strange and fucked up. It's all a balance, right, wondering if you're doing things the right way. But in the main, I don't have any regrets about it. It beat me up in certain ways, some of them physical more than spiritual, but I think the result was worth doing.

I know from the book's epilogue that, when it came out, the higher-ups were super pissed that this even happened. And yet the guards and the prisoners appreciated that you were telling their truth. How has the reaction to the book changed over the years?
I still hear once a week from someone who's come across the book for the first time, and they are relatives of people who are in prison or they're people who've done time and they say "Thanks for this book. It helped me understand what my husband is going through." Or "Thanks for this book, because it seems like doing time in Australia is a lot like doing time in the States." Or it's a public school teacher saying you wouldn't believe how much this resembles my day, which is a pretty upsetting thing to hear. But mostly, it's those readers, or people in some kind of class who've been assigned the book—the ones who really dig it write me and want to make contact. There were some spasms of anger, especially from the State of New York, when it came out, and from a couple of corrections professionals who took issue with the way I described some things. But now I mostly hear good things. And I hear it's still relevant, which makes me happy and makes me sad.

This interview has been edited for length and clarity.

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