How Alan Prendergast reported on ‘America’s loneliest prisoner’ and others like him

At the end of his recent true crime story for the Denver-based publication Westword, which details the life of one of America’s loneliest prisoners, writer Alan Prendergast mentions that “prison officials haven’t granted any journalist a face-to-face interview with any inmate at [the US Penitentiary Administrative Maximum Facility] since 9/11.”

What Prendergast doesn’t say in the article? He himself very well could have been that last interview (save for a “well-orchestrated tour or two” by the prison) more than twenty years ago. 

Alan Prendergast (courtesy of Anthony Camera)

“I was in there just a few weeks before the towers fell, interviewing Pablo Escobar’s top hit man,” Prendergast told The Sunday Long Read. “The prison insists that they [consider interview requests] on a case-by-case basis, but I think there’s a blanket ban on journalists, basically.”

That deep institutional knowledge speaks to how long Prendergast has been writing about the criminal justice system and high-security prisons — and just how creative he’s been forced to get in the absence of free-flowing information from prison officials. To report his recent story about notorious conman Jimmy Sabatino, who is only permitted to speak with his attorney and his 75-year-old stepmother, Prendergast cobbled together details from court records, descriptions from other prisoners, and past news coverage to paint a picture of Sabatino’s current solitary existence. 

“I was fortunate that he had taken it upon himself to file a lot of information in the case on his own behalf, even though he had an attorney,” Prendergast said. “And those letters that he wrote to the judge are what really makes the story come alive, because it gets his voice in the story.”

Prendergast is a senior contributor at Westword, and has also written for Rolling Stone, the Los Angeles Times, Outside, USA Today, Men’s Journal, and other publications. He is the author of two nonfiction books, “Gangbuster: One Man’s Battle Against Crime, Corruption, and the Klan” and “The Poison Tree: A True Story of Family Violence and Revenge.” He’s earned many honors for his work, including the Eugene Pulliam National Journalism Writing Award and two national feature writing awards from the Society of Professional Journalists.

The following interview has been lightly edited for brevity and clarity. 

You’ve written for a very wide range of different publications, but you’ve specifically written for Westword for many decades. How did you first start there?

I’ve been on staff there several times, between other arrangements, but it was always a good place to do long-form reporting, especially if it was something with a very strong local angle. I’m passionate about local news, but I’m also very involved in just finding good stories that make for long, interesting narratives. And Westword is a good display case for stories like that. 

Can you explain your typical process, if there is one, when you’re looking for your next story for Westword?

I’m always looking for something that’s interesting to me — if I’m not really taken by it or curious about it, it’s unlikely I’m going to be able to make a very compelling story out of it. But beyond that, it’s all over the map. I enjoy getting into places that I wouldn’t otherwise be, or meeting people I wouldn’t otherwise know. That’s sort of the whole point of journalism: It’s your passport to a much larger world. And I think that’s part of the reason why I’ve done so many stories about prison, because it’s one of these closed societies, its own subculture, that you want to get to know a little better. There are all these obstacles to doing that, which makes it more challenging and interesting to me. 

Especially with this story, and writing about someone who is only allowed to talk to two people in the world, it seems like a whole new level of difficulty in terms of journalistic access. 

Yes, it’s challenging. I think a lot of good stories don’t get told because of that. I did have access to ADX [the US Penitentiary Administrative Maximum Facility in Florence, Colorado] when they first opened, and of course that went away after 9/11. I think we’ve missed out on a lot of things that are probably important for people to know — how the inmates are treated, and how they’re dealing with mental health issues with this degree of isolation. And, of course, there are obviously some pretty notorious criminals in there. But there are always ways to tell a story if the front door doesn’t work. That’s part of what I’ve learned from years of doing this kind of thing. This story about Jimmy was irresistible because, on one hand, he’s such a character, and on the other he’s actually voluntarily chosen this degree of isolation. That makes for a fascinating psychological profile to try to figure it out.

What did your reporting process look like when you had so little access to him?

It was a little bit haphazard. It started with me learning that he was in there, and I was a little bit aware of his career, even though he’s not well-known outside of Florida. To find out that he was still doing [scams] in prison, and that he was doing them to such a degree that he felt he needed to be at this level of isolation not to commit more crimes, I thought: “Is this another con? Is this something real?” From there, yes, I was very reliant on records because he can’t talk to me, and his attorney can’t even talk to me.

In this particular very secure unit of the prison, does it only allow for only two prisoners — Jimmy and “El Chapo” — or could it house more people?

In this particular wing they call “The Suites,” I believe there are four units, but they can be very selective about who they isolate, and who has that title at any given time can change. Years ago, I did some writing about Tommy Silverstein, who at that point had been in isolation longer than anybody else in the federal system. They had a special place for him, which may have been converted to “The Suites” for all I know, but at that point the two most isolated guys were Tommy and Ramzi Yousef, who were both in this one area alone and could shout to each other. And then when prison officials found out they were communicating, they built another wall within this very isolated unit to seal them off from each other.

Jimmy’s now the king, but at some point somebody else might be even more isolated. And how do we even know who they are, when they’re that sealed off from the world? There are human rights groups that try to keep track of these things, but it’s difficult. It’s not like you can just call up the prison and say, “So, who’s in that unit?” It’s not gonna happen.

Was part of the draw in writing this story to show people that one of the most isolated prisoners in the country isn’t serving time for violent crimes?

Yeah, I think so. From television and movies, we have a distorted view of who is in these places. ADX has this reputation of housing the worst of the worst — people can probably tick off half a dozen names of infamous people who are there. But the vast majority of the prisoners are not infamous. They’re there because they pose an escape risk, or they’ve engaged in misconduct at lesser-security prisons, or they may have a mental illness they’re dealing with. The vast majority are probably not these mastermind, high-profile criminals — they’re something else. Jimmy, to me, sort of embodies that. He’s not necessarily a guy that you want to trust or get to know, but he’s certainly not the kind of security risk you might find with Ramzi Yousef or El Chapo, for that matter. 

How did you start building relationships with prisoners in the first place?

Well, it’s not that difficult. Prisoners have a tremendous grapevine. There are so many stories going on behind bars that you don’t know anything about, and if you take an interest and write an accurate story about one episode inside a prison, chances are other people are going to start writing you about their stories. So I get a lot of letters, a lot of prison mail. Many of those do not result in stories, obviously — sometimes somebody wants you to reopen their case, or they may be making bizarre claims, whatever. But I think it pays to pay attention to this stuff. Because when you start getting a series of letters from different inmates about something going on in a particular prison, or particular wing of the prison, there may be a really good story there. And those people often have nothing to do all day but to observe and write letters.

As you write in this piece, Jimmy seems to like the attention. Do you think there’s a chance that he’ll ever read this story?

That’s a good question — it depends sometimes on who the warden is. I’ve written stories about people in ADX who were told they couldn’t read it, and that the publication was intercepted being mailed into the prison because of some security concern, which is usually bogus. So I have no idea under the current regime how they feel about allowing those kinds of details about ADX to be presented to a prisoner, who clearly already knows them firsthand. 

But Jimmy’s lawyer also can’t tell me what he communicates with Jimmy. And I can’t get any response from Jimmy, so he’s not allowed to write me a fan letter, or a criticism for that matter. Someday, perhaps when he’s not under the same restrictions, maybe I’ll hear something. It’s a little eerie: The idea that your source may never see the story. 

After covering this particular prison for so long, and the prison system in general, how have you seen access for journalists change over that time?

It’s a mixed bag. I think at the federal level it’s gotten worse, particularly with this ban at ADX. In a lot of other places, there’s been a tremendous reform movement that’s tried to offer more transparency. You never really get total transparency when you’re dealing with this kind of institution, but I think it’s encouraging to see that more of these state systems are recognizing that they need to reduce their prison populations, and to work harder on re-entry programs. And part of that means forging more links to the outside world, which includes the press.

I’m not overly optimistic, because at the same time all of these systems are facing staff shortages, which makes it harder to accommodate the press, among other things. But there’s recognition that they need to have more access, and that they need to make that world more in sync with the outside world. Most of the people in there are coming out sooner or later.

Do you think there’s more of a spotlight on the issue of prison reform now, compared to when you started?

Oh, absolutely. One of the biggest battles in doing this kind of reporting is getting people to care. There are so many innate stereotypes and biases about people who are in prison, and the idea that we should just throw away the key or something. That was more of the attitude years ago. Now, I think people recognize that this certainly costs the public in various ways, and it’s good to know what’s going on in there. The whole social justice movement also has something to do with people looking at the criminal justice system, and looking for ways to improve it. 

Compiled by Amanda Ulrich. Photos courtesy of Anthony Camera and The Enigmatic Traveler/Creative Commons via Flickr.

The Sunday Long Read

The best longform journalism. Every Sunday.

Subscribe for free.

Become a member for just $5.