Shon Hopwood is an associate professor at Georgetown University Law Center. He co-founded Prison Professors, a blog about the criminal justice system, and he wrote a memoir called “Law Man.” When he was younger, he robbed five banks in rural Nebraska. He then served ten years in federal prison, where he discovered that he loved the law after helping out other prisoners. He became an astonishingly successful jailhouse lawyer: two of his cert petitions, including Fellers v. United States, were granted by the Supreme Court. He’s now an accomplished appellate practitioner.
My words are in bold; Shon’s are in plain text.
What kind of a teenager were you?
A rebellious one. I liked sports. I did not like academics nearly as well. In fact, I don’t think I ever took a book home my entire time in high school.
Looking back, were there any signs that you might have an aptitude for the law?
I did well on tests. I liked history and studying the Constitution. That was the one thing that was interesting. And I did well on aptitude tests, but I was a solid C student in high school — in part because I didn’t try. It really frustrated my parents.
Who were your role models back then?
Nebraska football coach Tom Osborne and probably Michael Jordan. The Cornhuskers are a big deal in Nebraska. When Nebraska has a game and they fill up the stadium, the stadium is the third largest city in the state.
You live close to pro sports teams. See, we don’t have any pro sports teams in Nebraska. College athletics is the only thing we have, and because of that, we have a much bigger following for our two major universities, The University of Nebraska and Creighton, than we would if we had states with professional sports.
Did one of your parents go to the University of Nebraska?
No. Most people that grew up in Nebraska in the 80s and 90s were Nebraska football fans
because the football team was so good. And basketball was my first love. It’s the first thing I found that I was really good at, and that I could just not get enough of. Which is much like the law now, but I didn’t have that then.
I was going to say — there are similarities between your practicing basketball all the time in high school and compulsively soaking up the law in prison. The same singleminded focus.
Yeah. Do you know who Malcolm Gladwell is? In one of his books, he talks about how people become experts or savants at a particular issue. And he says that you have to spend ten thousand hours of studying one thing, which is about ten years. After reading that book, I went back and thought about it. I spent about eight years in prison doing not much else other than studying law. Day in and day out. And I think that’s why I’m able to see arguments that other people can’t now. It’s because I just had a full focus on knowing the law — without a lot of other distractions. [laughs]
Part of the reason you quit college basketball is because you felt mediocre compared to the other players. But when you started out studying the law in prison, you probably weren’t amazing at it right away. What was the difference?
You’re right: I wasn’t very good right away. I knew nothing about the law, or very little, the day I accepted the job handing out books in the prison law library. The difference was that I grew out of sports a little bit. But the law was something I could do forever, and for the last eighteen years I’ve been, shall we say, trending upward in the law. And unlike basketball, where my body is now so beat up that I can’t play, I should get better at the law as time goes on.
In “Law Man,” you said that some guy knocked you to the ground in a prison
basketball game and wrecked your back.
Yeah. Prison basketball isn’t for the faint of heart. [laughs] It’s pretty rough, and I’m still suffering the consequences of being so foolish and playing so much of it while I was in prison.
How often did you play?
A couple times a week, every week. That was my escape.
Did a lot of guys show up to watch those games?
Well, we had leagues. And then sometimes we would just play during the afternoon pick-up games. But we also had leagues where people would show up and watch. That got me through the first couple years in prison until I found out I had a love for the law. And then I was either studying or playing basketball.
When did you realize that you loved the law?
I think once I started having some success. The law is really hard and challenging, and that’s what drew me in. But the law is also very frustrating when you’re litigating cases from inside a prison, and you know you that a claim that has merit, but you can’t get a fair shake because the judge sees a brief with a prisoner’s name on it. And because of that it would get discounted. It’s a lot of rejection for anyone who’s attacking convictions and sentences — for lawyers, let alone indigent federal prisoners who have never been to law school. It’s just a lot of rejection, a lot of losing. And so I think that winning a couple cases in those first formative years really propelled me forward. The case where that happened was John Fellers’, a Supreme Court case. And then I won a habeas case for a man named Melvin Brown that took ten and a half years off his sentence.
You obviously don’t want to go back to prison. But it must be frustrating to be on the outside and know that if you were still there, or if some other competent prison lawyer were there, people could have years shaved off their sentences.
It’s hard all the way around. So many people have been sentenced far longer than necessary to keep the public safe. And that’s part of the reason why I’ve started shifting from doing litigation, where you’re only helping one person at a time, to doing policy work, where the goal is to get a law changed that will help 100,000 people at a time. Because you’re right, I do feel bad that I can’t help more people. But I’m only one person, and there’s only so many hours in the day.
I’ve been working on sentencing and prison reform with FAMM, which is a nonprofit advocacy group here in DC. And now I’m working on reforming executive clemency. We just had a meeting at the White House earlier this week with a bunch of policymakers and advocates. I sat across from Kim Kardashian; she was there. And it looks like the White House is thinking about reforming the clemency process and making structural reforms so that the next person doesn’t need Kim Kardashian to advocate for them at the White House. Everyone will have a fair shot at getting a second chance and having their sentence commuted by a president.
So how did you get interested in the — what year are you in high school?
I’m a junior.
The thought of being interested in the Supreme Court as a junior in high school would have been so foreign to me. I think it’s really amazing and awesome now, but how did you start thinking about and getting interested in that?
Well, I’m pretty nerdy. So the fact that I’m interested in this isn’t shocking. But I became interested one day while I was in a study hall, and I was browsing the New York Times site. I stumbled across this oral argument transcript of a case called Maslenjak v. United States. It’s not really a big case. It’s about the relevancy of certain false statements when you’re applying for citizenship. But I ate it up, and I just loved it. So I started reading as many oral arguments as I could.
Huh. That’s a lot like my story. Only, I was reading legal briefs prepared by people like Seth Waxman and Paul Clement and Jeff Fisher and Tom Goldstein because I wanted to know how to do it better. I find the most interesting cases to me at the Court are often the ones that nobody pays attention to. I very much like those cases. In part because in the cases that aren’t the big political cases, it’s much harder to figure what justices are going to be on each side than, say, a case on affirmative action, where I can basically tell you what the votes are going to be no matter who argues the case and how they brief it.
What are some lesser-known cases that you’ve really liked?
Oh, well, I’m really partial to a criminal case called Apprendi v. New Jersey. That was decided June 26, 2000. I had been working in the prison law library for about six months, and all I did was check out books. I wanted nothing to do with the law. I didn’t know anything about it. Those books were big and thick and intimidating. But then the Court decided Apprendi, and I, along with every other federal prisoner in the country, thought that the reasoning in that case might apply to the Federal Sentencing Guidelines, and that we could all get a sentence reduction. So then I had a lot of motivation to pay attention the Court and study law, and that’s really what got me started.
One of my favorite opinions is a case called Crawford v. Washington, and that was a Justice Scalia opinion involving the confrontation clause — the right to confront your accusers at trial. It’s just a really great opinion on why the framers created the confrontation clause, and why the Court had nearly destroyed it for thirty years. And in that case, they reversed nearly thirty years of precedent on the confrontation clause.
How did you know about Apprendi? Did you keep up with most Supreme Court
Oh, yeah. I mean, people that are in prison are always following what the Court’s doing, and to a certain extent, what their circuit court is doing in case a decision comes out that could help them fight their case. Because you generally need to file within a year of a new Supreme Court decision that’s applied retroactively. And if you file too late, it doesn’t matter if you’re right. You’ll be barred from court. So most people pay pretty close attention. And when a case comes down that could impact people, that knowledge spreads like wildfire throughout the prison system.
How were you able to access the opinions?
We had books. Now they have legal databases, but then we had books and a Criminal Law Reporter that told us about which cases were up for consideration and which cases had been granted. I spent a lot of time listening to Nina Totenberg on NPR; any time a big case was argued, I listened to her at four o’clock on All Things Considered and heard about what was said at the argument. And I read newspapers and legal periodicals.
How long did it take before you could comfortably understand legal casebooks?
It depends on what area of law we’re talking about. [laughs] You can hand me an international law book today, and I’m not certain I would do any better than I did eighteen years ago as a federal prisoner. But you know, after a couple of years I felt a lot of familiarity with how judicial opinions are written and the reasoning behind them. Things started to click shortly after the Fellers petition.
Which books did you use most frequently in the law library?
The Georgetown Law Journal Annual Review of Criminal Procedure. That’s a book that
Georgetown still puts out today. It was very helpful in figuring out the law. There were books on habeas corpus, which is basically post-conviction motions, and I read a lot about those. And then there was a legal casebook called Modern Criminal Procedure that basically helped me understand what the issue was in Fellers.
There’s another famous jailhouse lawyer named Clarence Earl Gideon, who lent his name to Gideon v. Wainwright. Did you know about him when you were a prisoner?
I did. I had seen the movie that had been made about that when I was a kid, so I remembered Clarence Earl Gideon. You know, there’s a surprising number of cases that have been filed or granted by pro se people in prison over the years. In fact, I need to write an article about that someday.
I would read that article.
Yeah, it’s kind of fascinating. Going through the years, and seeing the number of cases — it’s not a great number. The chance of an indigent prisoner getting their case heard by the Supreme Court is one half of one percent. It doesn’t happen often, but when it has… Gideon is one of the most cited, most important decisions of the twentieth century.
Did you see this dynamic with indigent prisoners’ cases when you clerked on the D.C. Circuit? That must have been a pretty small percentage as well.
We had a couple pro se cases when we clerked at the D.C. Circuit, but they weren’t prisoners; they were people that were out and couldn’t afford a lawyer. And I remember one case involved the tax court. Somebody was disputing income taxes and actually came and argued a case on their own in the D.C. Circuit.
I don’t know anything about tax law, but it seems very complicated.
Yes, it is. [laughs] It is. She was a stewardess who lived overseas part of the time and was
disputing that part of her income should have been taxed under American law. And she lost most of her case, but she won on one particular argument. So she got a reversal and remand on it. Which, you know, a lot of lawyers can’t say they’ve done the same thing in the D.C. Circuit. I’ve never argued a case in the D.C. Circuit. I’ve litigated cases there, but I’ve not argued there.
How many arguments did you get to watch when you clerked there?
I watched as many arguments as I could. The D.C. Circuit is kind of unique, even among all the federal courts of appeals, in that there’s a higher percentage of really good appellate advocates in that court. One because it’s in D.C., and two because of the nature of some of the cases. There are administrative law cases that are really important, and so they draw some of the best attorneys. I liked to see arguments because I’m always trying to learn how to be a better oral advocate.
What did you learn from those oral advocates in the D.C. Circuit?
Quite a few things. One, when a judge asks you a yes or no question, give him a yes or no
answer and then explain it. So many attorneys want to fight the judge on the question that they never end up answering it. I watched judges get very frustrated by that. Another thing is that when the judges are asking questions, you stop talking altogether. No matter how important it is what you’re saying, when they start talking, you stop. The good ones wouldn’t do that, but I would see bad lawyers try to talk over the judges. That kind of defeats the whole purpose of oral argument.
The best arguments are really like a conversation. It’s why I, for the most part, take one or two pages of notes, and then I’ll set the record to the side. I don’t want to refer to anything unless I absolutely have to. Because any benefit you get from looking down at your notes and reading, you just lose so much by not making eye contact with the three judges as you’re giving a response to a question. So I did an argument in the Washington State Supreme Court last November where I put all my materials on the side and really had nothing in front of me. And I find that I do better that way.
That sounds terrifying.
[laughs] It is a little terrifying. But at the end of the day, that works for me. If I have to rely on notes at an oral argument, then I haven’t done the prep work. Usually, by the time I get into an argument, I can tell you everything about a case by memory. And I’ve usually done at least three moot courts. I’ve got an argument on September 27, and I’ll do three moots before I even drive down to the courthouse.
And you do those moots at Georgetown?
I do. We have a really extraordinary faculty at Georgetown as far as faculty who, at one point in time, have been appellate practitioners. And some still are. You know, we have the Supreme Court Institute at the law school. We’re the only law school in the country that has that. And in the last three years, I think, we have mooted 99% of cases that have come before the U.S. Supreme Court.
When lawyers want to get their case heard, one from each side calls Georgetown. Everyone wants to do the moot there because they’re really good. We get the top appellate lawyers to serve as justices. Last time I served as a justice, I sat next to Don Verrilli. When both of the advocates call, Georgetown flips a coin for who gets it. So we get one side of almost every case that’s argued in the Supreme Court year after year after year.
They actually flip a coin?
Yup. And Georgetown has a courtroom for this purpose that looks like the Supreme Court.
I guess it’s meant to elicit the same anxiety as that big, high-ceilinged courtroom at the Supreme Court.
It is. And it’s a public service for the Court, to help prepare advocates. Everybody does it, from Paul Clement to Seth Waxman. But you know who really gets the most benefit from doing it? First-time advocates at the Supreme Court. Because they’re going to be mooted by people who follow the Court closely, who have argued a lot in the Court, and who know what the justices are looking for.
How often do you serve on moot panels?
I do a couple every year. I do them for a number of reasons. O of them is that it makes me a better lawyer to do those moots. You’re learning an area of law you may not have learned before. You’re thinking about the arguments in a way that a judge would, and then you’re sometimes trying to help the advocate change their arguments to the ones that will be most persuasive. And just going through that routine several times a year is really beneficial for someone that does appellate law.
Do you volunteer for moots, or are you selected?
They have a selection process. They call me, especially on criminal cases — I do a lot of work for criminal cases. And you teach classes related to sentencing and criminal justice reform, right? I do. What’s your favorite part of teaching? I’d say watching students graduate and then go on to have remarkable careers. Or just the interaction in class I find fun. I tell my students to argue with each other, and to argue with me if they think I said something wrong. So we have pretty robust arguments in class, and that’s the
way I like it. It’s similar to an oral argument, where we’re discussing and not getting upset about things, but we’re very much arguing each other’s points. I want to prepare students to do what lawyers do, which is argue — and do it respectfully, and do it without it becoming personal.
If my students don’t remember anything else, that’s what I want them to take from my class. I feel like that is a broader issue in America that many people have problems with. Nobody can argue anything without getting offended, or devolving into name-calling and ad hominem. As a lawyer, you can’t afford to do that when you’re arguing on behalf of a client. It’s counterproductive, and it’s not effective advocacy. It just isn’t. You never score points with a judge for putting down the other side.
Another broader issue, I think, is that a lot of lawyers are unhappy. Of the lawyers who know who love their jobs, what are they doing differently?
I enjoy the law, but I’ll tell you: the law itself wasn’t what got me into the civic career. And it’s not what changed me when I was in prison. What changed me was using my legal skills to help other people. And I feel like people who want that as their careers do really well in the law because there are all sorts of different ways to help people.
You know, when you’re just doing document review for seventy hours a week, and you don’t really have any decision-making power over the shape of the litigation, that would be miserable.
I have a few more questions. If you could sit down with the Attorney General for ten
minutes, one-on-one, what would you talk to him about?
[laughs loudly] I probably shouldn’t answer that. In part because I’ve already done that, and had that conversation, and I should not talk about it. I met the Attorney General back in January at the White House, and all I’ll say is that we had an interesting conversation.
Alright. I won’t press any further, then. Are there any books that you’d recommend about mass incarceration?
There are a couple different books. There was a book last year that won the Pulitzer Prize from Professor James Forman of Yale Law School that is really, really phenomenal, and it’s called “Locking Up Our Own: Crime and Punishment in Black America.” I would highly recommend that one. And then the other one is a book called “Locked In,” by a law professor at Fordham named John Pfaff.
Which non-legal books have influenced you?
I am a very big fan of Raymond Carver, who was a short story fiction writer in the 70s and 80s. He wrote in a style that’s called minimalism, which I think more lawyers need to adopt. Lawyers tend to overwrite. Those books, and the writing in them, impacted me.
Have you heard of Chuck Palahniuk? He wrote “Fight Club,” and he’s written a bunch of books. He writes in the same style. They write short, choppy sentences that sound just like how someone speaks.
And have they influenced your own writing style?
They have, because I used to write based on how I thought lawyers wrote. But it turns out that lawyers are horrible writers, and many judges are horrible writers, and the whole profession is moving to what’s called plain language writing. We’re using less legalese, and more legal briefs read like they’re pulled out of the New York Times.
When did that movement start?
Probably ten, fifteen years ago. I’ll tell you, my favorite legal writing book is by a guy named Ross Guberman. And it’s a book called “Point Made.” It’s by far my favorite writing book. What he did was he took the top fifty appellate advocates, looked at a bunch of their briefs, and pulled out strategies that they all used. And then he actually takes methods from each brief and illustrates the point by examples from the best appellate litigators in the country. And that’s how I learn the best: by seeing examples. So I can’t recommend that book enough. I tell my students all to buy it. I’ve probably bought twenty or thirty copies that I’ve sent people all over. I also know Ross really well now, and I’ve had him come speak to my class.
Other interviews conducted by Anna Salvatore: UChicago law professor Justin Driver, former Solicitor General Neal Katyal, court artist Art Lien, New York Times Supreme Court correspondent Adam Liptak, UCI Law Professor Leah Litman, litigant extraordinaire Fane Lozman. former Court writer Linda Greenhouse, NPR reporter Carrie Johnson, Fix the Court Director Gabe Roth, IU Maurer Law Professor Ian Samuel, and Lawfare editor-in-chief Benjamin Wittes.