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Shon Hopwood tells about his journey from bank robber to federal prisoner to U.S. Supreme Court practitioner and Georgetown law professor.

Aaron Ross Powell
Director and Editor
Trevor Burrus
Research Fellow, Constitutional Studies

Shon Hopwood is an American appellate lawyer and professor of law at Georgetown University Law Center. Hopwood became well‐​known as a jailhouse lawyer who served time in prison for bank robbery. While in prison, he started spending time in the law library, and became an accomplished United States Supreme Court practitioner by the time he left in 2008.

Shon Hopwood joins us this week to tell about his journey from bank robber to federal prisoner to U.S. Supreme Court practitioner and Georgetown law professor.

What’s it like in federal prison? How did Hopwood become a jailhouse lawyer? If people do in fact “age out” of criminal activity, then what should our prison system look like?

Show Notes and Further Reading

Hopwood’s book is Law Man: My Story of Robbing Banks, Winning Supreme Court Cases, and Finding Redemption (2012).

Here’s the New York Times article by Adam Liptak that Hopwood mentions, “A Mediocre Criminal, but an Unmatched Jailhouse Lawyer.”



Trevor Burrus: Welcome to Free Thoughts. I’m Trevor Burrus.

Aaron Powell: I’m Aaron Powell.

Trevor Burrus: Joining us today is Shon Hopwood, associate professor of law at Georgetown Law Center and author of “Law Man: My Story of Robbing Banks, Winning Supreme Court Cases and Finding Redemption.” Welcome to Free Thoughts, Shon.

Shon Hopwood: Thanks for having me.

Trevor Burrus: What is it like to rob a bank?

Shon Hopwood: Everything in your body is telling you to get out of that bank. [00:00:30] Just think of the most anxious, anxiety‐​ridden moment of your life and then times that about 100. What’s weird is, sitting here telling you now, I can’t imagine going to do that now because my life is so different, but 20 years ago, I was a much different person and very crazy and wild. At the time, it sounded like a solution to some problems and turned [00:01:00] out not so much.

Trevor Burrus: Your first bank robbery was … You tell in the book about dropping a toolbox. Is that what it was?

Shon Hopwood: A toolbox.

Trevor Burrus: That seems like a very advanced bank robbing strategy. Actually, your whole first bank robbery seemed very advanced. It’s gets less so‐

Shon Hopwood: Very advanced. Very advanced for too young 20‐​year‐​olds who had no idea what they were doing.

Aaron Powell: How do you end up robbing a bank?

Shon Hopwood: Well, you mix [00:01:30] in some immaturity, no purpose. I had no idea what I wanted to do with my life, some depression, some alcohol and drugs and a bunch of other young, stupid, immature 20‐​year‐​old men and you combine that and what came out was five armed bank robberies and me and five or six people robbing all of these banks together over the scope of a year.

Aaron Powell: Were these banks near where you lived?

Shon Hopwood: [00:02:00] No, they were … Well, yes. They were all in eastern rural Nebraska, but they were all banks that were so small and the towns were so small that they didn’t have any local police departments, which is the reason we went there. Rather than going to a big, huge office in a big city, whereas soon as you hand over a note or walk in with a gun, the police are going to be there in two or three minutes, we decided to go to these rural [00:02:30] towns.

Trevor Burrus: You did have a gun?

Shon Hopwood: I had guns on all five robberies.

Trevor Burrus: They were fired?

Shon Hopwood: No.

Trevor Burrus: That probably helped with your sentencing maybe a little bit?

Shon Hopwood: Yeah. Helped a little bit. If they had been fired, I think that I would still be in federal prison.

Trevor Burrus: You discuss how your friend, Tom, he only did the first one. He was a very old childhood friend of yours.

Shon Hopwood: Yep.

Trevor Burrus: Then you kept going, and it seemed like you had more [crosstalk 00:02:56]

Shon Hopwood: I was an overachiever.

Trevor Burrus: Yes. Yes. Just like you are today, yes. [00:03:00] Maybe you’re not exactly not the same person. You still go all the way when the call comes. You kept going and you got more careless the way you describe it.

Shon Hopwood: Very careless. I was never under any illusion that we weren’t going to get caught.

Trevor Burrus: That’s an interesting point of this. You’re just like, “I’m going to do this until I get caught.”

Shon Hopwood: I just kind of knew that this was eventually going to end, and that kind of tells you where my mind state was. My thought was, “When they come to get me, there’ll probably be a shoot‐​out. I’ll be dead and therefore [00:03:30] I’m not really worried too much about the consequences.” When you don’t care about the consequences of your actions on yourself, it’s really easy to forget about the consequences of your actions on others.

Aaron Powell: How much money did you steal?

Shon Hopwood: I think all together it was 175,000 over five banks.

Aaron Powell: Did you live high on the hog while …?

Shon Hopwood: Well, it’s much easier to spend money when you don’t earn it, and yes. It was a nonstop party for a year. [00:04:00] Every stupid thing that you could ever think to buy, we bought. I don’t know where my friends and people I was around thought the money came from because they saw me living a lavish lifestyle and not working, so I knew it was going to come crashing down at some point.

Trevor Burrus: When you were caught, you didn’t get a trial. It was like most prisoners do not get a trial. You pled to … Is it unarmed robbery did you plea [00:04:30] to?

Shon Hopwood: I pled to unarmed robbery and then the use of a firearm during one of the robberies.

Trevor Burrus: Oh, okay.

Shon Hopwood: If I had pled guilty to one more firearm charge, people think the bank robberies is what I got the time for. I got seven years, three months for the banks. I got five years for one gun. If I had been charged with use of a firearm during the other four robberies, I would’ve been looking for just the gun charges at a mandatory minimum sentence of 85 years.

Trevor Burrus: Jeez, [00:05:00] and you then found yourself in Illinois. Interesting, I guess‐

Shon Hopwood: Yeah, federal prison in Illinois. Nebraska doesn’t have a federal prison, so …

Trevor Burrus: It wasn’t maximum security? It doesn’t sound like from the book.

Shon Hopwood: No, it was a medium‐​high security, so one level down from maximum.

Aaron Powell: What does the mean in practice?

Shon Hopwood: Well, a little less violent. It was place where there were people at the out‐​dates. Most of the [00:05:30] people in the max, they may have an out‐​date, but an out‐​date that’s 40 or 50 years away or several life sentences, so there were people with out‐​dates at my prison, which meant that there was a little less violence because people eventually wanted to go home, but for the most part, it was prison kind of like what people think prison is like, and there were a lot of boredom and a lot of violence, and your movements control in every [00:06:00] single way.

Trevor Burrus: What is the first night in prison like?

Shon Hopwood: Just not a lot of sleep because you don’t know what’s going to happen the next day and you kind of just … It takes a while to figure out what prison is like. You don’t ever really feel comfortable in prison. Plus, you don’t really want to because if you do feel comfortable in prison, that probably means that’s where your focus is rather than on getting out, but it’s not a place where [00:06:30] there’s a lot of peace.

Aaron Powell: How did you end up getting into being a jailhouse lawyer, effectively?

Shon Hopwood: Bad luck. I’m kidding. Yeah, so I got a job in the prison law library so that I could get of the kitchen where I was scrubbing tables, which wasn’t much fun, and the kitchen is one of the most dangerous places in the federal prison because, even though there are prison guards watching, there are things like knives [00:07:00] and all sorts of things you can use as weapons, so I got a job in the prison law library, and for the first six months there, I wanted nothing to do with the law. I just checked out books.

When I did pull down one of those books, they were big and intimidating and thick. When I did read them, it felt like they were written in another language and I didn’t think much about having a career in law. Then June 26th of 2000, the supreme court handed down a decision [00:07:30] called Apprendi v. New Jersey, and I along with every other federal prisoner in the country thought, “Maybe this could lead to a sentence reduction.” All of a sudden, I had a lot of motivation to try and learn the law on my own and try and figure this all out.

Trevor Burrus: What is that decision? What did they say in Apprendi?

Shon Hopwood: They said that facts which increase your maximum sentence [inaudible 00:07:52] prove to a jury beyond a reasonable doubt, and I had pled guilty to unarmed bank robbery [00:08:00] but had been sentenced and had my sentenced enhanced based on the gun, even though I also got a gun charge, and so my thought was, “Well, if I had to actually plead guilty to armed robbery to get that enhancement, this violated Apprendi.” It turns out I was right, but it took five or six years for the rest of the criminal justice system and the supreme court to get there, so by then, it was too late to help me.

Trevor Burrus: Because your case was finished?

Shon Hopwood: Yeah, because my case was finished, but what I found was I really enjoyed the process of solving these legal puzzles, [00:08:30] writing out the solution and then once I started winning cases, I found out I really enjoyed helping my fellow prisoners get time off their sentence.

Trevor Burrus: You didn’t have an undergrad degree either?

Shon Hopwood: I did not. I did not. I had never done any writing other than letters to people when I started this kind of venture. I just learned by reading lots of good books and lots of lawyers send in briefs that were really good, people like Seth Waxman, and I just [00:09:00] tried to emulate what they did.

Aaron Powell: The success that you had and the praise that your legal writing received showed an enormous, almost it seemed like natural talent for this stuff. Was there a point at which … You started reading the legal stuff and you started doing this for this very practical reason, but was there a point at which it ticked over into intellectual curiosity or you discovered that you also [00:09:30] just have an affinity for it?

Shon Hopwood: No, very much so. I was a solid C student in high school. Did not do very well in part because I didn’t really care and it was not interesting to me and not challenging, and the law was challenging from the get‐​go, and I really got drawn in and realized that my writing ability, it took many, many years to get that to where I would be proud to say [00:10:00] I wrote something from several years ago, but as far as analytical ability, I kind of felt like I got that right away, and I could see arguments and I could see arguments that lawyers were making that were wrong, and most of the cases I won were in effective assistance of counsel cases where lawyers had made mistakes.

Trevor Burrus: When you enter prison, it seems like, and I think you write in the book, that the first year or so, I think you say something like you move past the, [00:10:30] “I don’t care about my life” stage and you start thinking about a future and some sort of … It seems that that’s a lot of the problems that occur in prison for prisoners, from violence to other types of abuses is because there’s no hope or something like that. Did you get hope from the law and you also, of course, were corresponding with your future wife, which gave you some hope, too. Was that really important?

Shon Hopwood: That was part of it. It’s [00:11:00] really hard to get up and kind of seize the day, so to speak, when you’re facing a 20‐​year mandatory minimum sentence. In the federal system, you know you’re going to … even with good time and good behavior, you’re going to serve 17, 18 years of that. It’s really hard, especially for someone that’s 20 or 21 or 22 to think, “Oh, well, I need to be working on myself today to get myself ready for release,” when the amount of time you’re going to serve is equivalent to the amount of time you’ve been alive, [00:11:30] so it is very hard, but the closer you get to the door, the more you realize or at least you should realize that, “Woah, I’ve got to start thinking about life on the outside.”

For me, I made it through the first couple of years and then I started winning cases in court and corresponding with my now wife and having a great mentor in Seth Waxman who is a former solicitor general of the United States, and all of those things led me to [00:12:00] make quite a few changes, and the fact I just grew up. I was 22 and 21 when I committed these crimes. By the time I hit 25, 26, 27, I was in a different place like most young men are, and that’s one of the reasons why these long sentences don’t really serve society well, because people tend to age out of crimes because they just mature and everyone knows this intuitively, but the criminal justice system [00:12:30] has not really caught up to that.

Trevor Burrus: Talk about your fellow prisoners. You mentioned some of them, but you had mentioned, I think, in a sort of wonderful way that you became one of the welcome wagon for the prison. You give new prisoners a good bar of soap and a toothbrush and things like that, so if I was coming in and you were walking me through, like a tour guide, and saying, “These are these people. These people …” How would you introduce someone to federal prison?

Shon Hopwood: [00:13:00] Yeah, so that’s the really interesting thing about prisoners. They’re very generous, so when you come in people did that for me. I was going to go take a shower and somebody stopped me and said, “Oh my gosh. Don’t walk in the shower barefoot. Don’t ever do that. Here’s a pair of shower shoes.

Trevor Burrus: Same with the dorm rooms.

Shon Hopwood: Yeah. Yeah. There’s certain things you just don’t do. Here’s a toothbrush. Here’s toothpaste because you aren’t going to get to the commons area, [00:13:30] the store, for several days, and so people did that for me and it’s just … I would see prisoners constantly returning the favor. Some of it was based on race, where you grew up. We had a group of guys that were from Nebraska that tended to look out for black or white or Hispanic prisoners, but that they were coming from Nebraska, and so what you find is there is a sense of tribalism even in federal prison.

Trevor Burrus: [00:14:00] You have to know these rules just about where you sit for lunch and who you talk to and all these things.

Shon Hopwood: The consequences are so severe. I reached across to get a cup of milk one morning, reached across someone’s tray, literally put my arm over their food and the guy wanted to kill me. First thing in the morning, said, “If you ever do that again, I’m going to take this tray and beat you over the head with it.” You know what? I learned my lesson pretty [00:14:30] quickly.

It’s funny because in prison there is far more respect for people that I ever see like here on the metro and DC, where people will almost kill each other or a seat or to get out of a car to go to their important job. In prison, it’s not like that because the consequences of being rude and disrespectful are so immediate and severe.

Aaron Powell: Is that a, I guess the reasons for that. Is that just a factor of [00:15:00] there’s naturally going to be violent people in prison and so you just behave this way because you don’t know who might be violent, so it’s better to treat everyone as they might be, or do you get acculturated into that? Did you or other prisoners who weren’t that way come to behave that way over time, too?

Shon Hopwood: Yeah. I just think you learn very early on in prison that respect is very important. [00:15:30] That’s all these guys got. Some of them have no family. Some of them are doing several life sentences. All they have is respect, and you realize really early on that that’s how you behave, and if you don’t, there are consequences.

Trevor Burrus: Are there a lot of innocent people in prison, do you think, or I guess it would be a secondary question because a lot of people might think with the federal [inaudible 00:15:57] project and things like this that there are a lot of innocent people in prison. [00:16:00] Do you think that that’s true?

Shon Hopwood: I didn’t see a lot of what you would call factually innocent people in federal prison, but what I saw were thousands of people who sentences were increased based on bogus things, like back when I was being sentenced, it was mandatory guidelines, mandatory sentencing guidelines, and the only way you really got out of those was if you cooperated.

What would inevitably happen is the people that were cooperating and [00:16:30] would embellish drug amounts, make drug amounts up, try and recruit other people to corroborate their story to the prosecutor, and you would see people like my friend, John Davis, who I write about in the book, who the police found point four grams of methamphetamine in his house, but he was sentenced to 14 pounds of methamphetamine based solely on the testimony of a bunch of drug addicts who are looking to get their own sentences reduced. [00:17:00] If John had been sentenced to the point four grams, he would’ve done a year or two, but instead, he was sentenced to 14 pounds and he was a first‐​time offender given a mandatory life sentence.

Trevor Burrus: He’s the one you referred to as “Hater?”

Shon Hopwood: Yes. Yeah.

Trevor Burrus: At one point, he actually confronted one of the … I don’t know if “snitch” is the right term. Informants, who you call “Voicebox.” That’s a fascinating story.

Shon Hopwood: Yeah, so we walked into the cell and John approached this guy and said, “Do [00:17:30] you know who I am?” The guy’s like, “No.” He’s like, “Really? You don’t know who I am?” and the Voicebox, because he had his larynx taken out from throat cancer, says, “No, I don’t think I’ve ever met you,” and John pulls a piece of paper out of his back pocket and says, “Well, then why did you tell the prosecution you bought two pounds of methamphetamine from my house and you even described my dog at my farm?”

The guy started crying and basically broke down the entire story, how John’s co‐​defendants [00:18:00] had paid him 1,000 or 2,000 dollars to corroborate what they were saying against John so that they could all get time off because, like I said, under mandatory guidelines, the only way people are getting out from under these 10 and 20 and 30‐​year sentences was to cooperate, and it didn’t look like to me, at least in Nebraska, that there was a lot of quality control from the US Attorney’s Office, and they would just take whatever anyone said and trot them into court. That’s kind of how in [00:18:30] the system worked. In fact, it was so bad in Nebraska that they had a term for this. It was called, “Jumping on a case,” on someone else’s case, even though you knew nothing about them.

Trevor Burrus: John is still in prison?

Shon Hopwood: John is still sitting in prison serving a mandatory life sentence.

Aaron Powell: How does that work? If they find, just from the procedural standpoints, if they find a vanishingly small amount of methamphetamine and that’s all the cops have actually found, how do you then argue in court like, “Well, no. In fact, what [00:19:00] he actually had was this amount that we didn’t find”?

Shon Hopwood: Yeah. Well, so they got him for conspiracy and they had … The jury found over 500 grams was involved in the conspiracy, which the federal system sets that set of statutory minimum and maximum of 10 years to life. Then the judge, back then, could find whatever he wanted or she wanted as far as facts that produced a bigger drug amount by preponderance of the evidence [00:19:30] at sentencing, and that’s what you get sentenced to, is whatever fact‐​finding the judge does then. They brought some of these people out, and yeah.

Trevor Burrus: You said, “back then.”

Shon Hopwood: Well, so it’s a little different now because there’s advisory guidelines. The supreme court in 2005 finally bought the argument that I had presented to my judge in 2000 and declared the guidelines aren’t constitutional, and so now the judges can depart from the guidelines [00:20:00] and there’s not so much pressure on people to run to the prosecutor to get a lower sentence because they feel like, “I don’t have to cooperate. I can just plead guilty and then try and convince the judge to not send me away for 20 years.” Back then, that didn’t happen.

Aaron Powell: You’ve argued quite a lot that these sentences are too punitive, they’re too long and that’s something that we at the Cato Institute, census and reform is an important thing, but is there among the prisoners … so, of course, many [00:20:30] prisoners probably think that their own sentences were too long because of the sort to things you just described or other factors, but is there a sense among the prisoners that in general criminal sentences are too punitive, too long?

Shon Hopwood: Yes. I felt that way. I actually, with my 12 year, three month sentence, felt like I got a pretty good deal when I got to prison and saw all these young African American men [00:21:00] with nonviolent drug cases not involving firearms doing 20 year mandatory minimums for crack cocaine. I felt very lucky, but you quickly realize that the sentences on the whole are just far greater than they need to be to protect the public.

One of the things I argue about with people all the time is this notion of general deterrents. You sentence someone long so it deters everyone else. I don’t think that actually is a [00:21:30] thing, and the reason is I never met anyone in federal prison who knew the amount of time they were facing, and the sorts of people that commit these crimes are people with drug addiction, alcohol addiction, mental health illness.

Impulse control issues are all four, so they’re not rational actors, but even if they were, to try and figure out the amount of time you would face for a federal crime, you’d have to research and find the one of 5,000 federal criminal statutes, determine the statutory minimum [00:22:00] and maximum, and then you’d have to go to a 500 page guideline manual that judges and lawyers misapply every day in federal court, and to think that anyone actually does that and weighs that out before they commit a crime, I just never saw it in 11 plus years of being in the criminal justice system.

Trevor Burrus: Well, I do that before I commit every crime. Got all the law books, every sort of thing, put together the likelihood of being caught.

Shon Hopwood: I know, but Jeff Sessions thinks that general deterrents. That’s why we have [00:22:30] to have these long sentences, because it tells everyone else not to do this, and I just have never seen any evidence, either empirically or anecdotally that says that that actually happens.

Aaron Powell: It seems so nonsensical that that’s what happens and that these long sentences actually deter people. To me, it just makes it clear that, say, someone like Jeff Sessions who just last week or the week before ordered federal prosecutors to always seek maximum penalties, [00:23:00] that it’s not about deterrents. It’s punitive. They just feel like people need to be punished and punished harshly and they want to do it, which is also partly why it’s hard to argue against it, because it feels like all the arguments about, “It doesn’t deter things and it has these terrible effects,” is like, “Well, but so what? Because we’re punishing them and they deserve it.”

Shon Hopwood: Well, I see that a lot, too, and I think there is a fundamental mismatch [00:23:30] between people that are politicians, lawyers and federal judges who, on the whole, all those groups of people are generally rule followers. The problem is, they’re the ones that set the laws and assume everyone else is going to follow the rules, and the majority of Americans are not rule followers.

Walk out into the street and just watch people walk across the street when the sign for not walk is not on, or speeding laws or any of the other laws. [00:24:00] We’ve got millions of people that use an illegal substance every day in this country, and so there always seems to me to be a mismatch between what someone like Jeff Sessions thinks the world should be and what America is actually like.

Trevor Burrus: How did you get involved in your first supreme court petition for [inaudible 00:24:19]?

Shon Hopwood: Yeah, so a friend of mine from Nebraska, John [Fellers 00:24:22] came to me one day.

Trevor Burrus: This is in prison?

Shon Hopwood: This is in prison, and I had been self studying the law for 18 [00:24:30] months at this point.

Trevor Burrus: Set the scene. You’re in the prison yard?

Shon Hopwood: We’re in the prison yard and he comes and says, “The A circuit just denied my appeal.” He had gone to trial on a conspiracy to distribute methamphetamine, received a sentence that was the same as mine, 12 years. I walked in five banks with guns, got 12 years. He sells a little meth and gets the same amount of time as me. He says, “You know, I lost in the A Circuit. [00:25:00] I want to file to the supreme court and I called my lawyer and he says, “We’ve got no chance of winning in the supreme court,” but as many lawyers like to do, he said, “John, if you give me 12,000 dollars, I’ll throw something together to file in court.”

John just didn’t think that that was a great idea, but he had to do some convincing, because at that point I had filed, I think, one or two habeas petitions and I knew enough to know that filing a habeas petition in federal district [00:25:30] court is not the same as convincing the United States Supreme Court to take a case. I was hesitant to do it because I didn’t think I could. John was persistent, and I said, “Yes,” and I spent two months basically working on his case day and night and pecked out that petition on a prison typewriter and we sent it off.

I largely forgot about John Fellers and this case because I knew the odds were against us and John had transferred to another prison, and one morning [00:26:00] I’m walking out to the recreation yard at 6:30 and a friend of mine comes running and screaming out of the housing unit. This being federal prison, the first thing I thought was, “What did I say to this guy yesterday that he wants to come fight me at 6:30 in the morning?” You don’t usually go to a fight carrying a newspaper in your hands, and what he had was a copy of the USA Today saying that the court had granted John Fellers case.

How unlikely that was given that he had filed pro se without a lawyer and it actually quoted from the brief that I [00:26:30] had written out on a legal pad and then pecked out on a prison typewriter. I had no idea what it would lead to, but it was, on the whole, as far as prison days go, it was a pretty good day.

Trevor Burrus: You wrote a note on the cover of the brief to the court.

Shon Hopwood: Yeah. Yeah. We prepared a cover letter and I just said … and I don’t actually have a copy of that, and I don’t know if the court [00:27:00] does or not, but the letter just said, “Hey, I know you get lots of these from prisoners all over the country. Most of them have no merit. They’re hard to read, but this case actually does have merit. It’s really interesting issues. Take a look at it.” I have no idea if that played any role, but …

Trevor Burrus: I think it could. There’s so many pro se, you got to get them to take notice somehow.

Shon Hopwood: Yeah. Yeah, and that’s the whole ballgame up there because they’re getting briefs from all over the place.

Trevor Burrus: [00:27:30] What was the issue in John’s case?

Shon Hopwood: The issue was the police … John had been indicted, which means it started adversarial proceedings, which means the sixth amendment right to counsel kicked in and the police came to his house, knocked on the door. He opens the door and they say, “Listen, John. We’re here to talk about your involvement in methamphetamines conspiracy.” They don’t tell him he’d indicted. They don’t read him Miranda Warnings, and then they just sit there as John starts [00:28:00] to make incriminating statements.

They then arrest John. They take him 20 minutes to the jail. They put a Miranda Warning in front of him as they’re asking him the same questions they had asked him at the house and he signs the Miranda Warning, repeats the same answers, and that was all used at trial against him. The question was whether they had violated his sixth amendment rights by not reading him Miranda when they arrested him at the house and whether that also tainted the subsequence [00:28:30] interrogation at the jailhouse, because John thought, “Well, I let the cat out of the bag once. At that point, it doesn’t really matter if I invoke Miranda or not. I’m screwed,” and so he went for it and the court said unanimously, nine to zero, that the first interrogation violated his rights.

They punted on the second issue, sent it back down to the A Circuit. A Circuit ruled against John, but while he was there, Booker came out that said the sentencing guidelines were unconstitutional, [00:29:00] so he went back for re‐​sentencing, but we lost on the trial issue, and this time Seth and Wilmer Hale filed the petition to the Supreme Court, and the second time they denied it, which I always tend to remind Seth about. “You may have argued 80 cases, but I think I probably … You should’ve let the jailhouse lawyer handle that one.”

Trevor Burrus: After the petition was granted, of course, lawyers all over would love to take any of those cases just to argue in front of the supreme court, [00:29:30] but you happened to get, as you mentioned, Seth Waxman, who is one of the biggest lawyers in town, and then, amazingly, you were kind of brought in as co‐​council. You were in jail, on conference calls, and they were sending you briefs for comments, but you had to comply with all the weird prison rules. What was that like?

Shon Hopwood: Well, Seth tells it like this. Seth says, “Federal prisons are very used to lawyers calling in to communicate with their clients. What federal prisons are not accustomed [00:30:00] to is lawyers calling the jailhouse lawyer of their client.” It presented some problems, but we worked through it, and yeah, Seth and the lawyers at Wilmer Hale made me a part of the team and I’m forever grateful because I think a lot of people with Seth’s background, Harvard undergrad, Yale Law School, Solicitor General of the United States, I think a lot of people would’ve said, “Hey, Mr. Jailhouse Lawyer, great job getting the case granted, but we’ll take it from here.”

That is the exact opposite of what Seth did. [00:30:30] I found out many years later after I got to meet the people at Wilmer Hale that they actually had a nickname for me. I was in‐​house council, as in the big house.

Aaron Powell: When you were collaborating with them, what kind of work were you doing?

Shon Hopwood: Probably a little of nothing of help to them, looking back at it now. I was just writing notes about … I was, by this point, pretty familiar with the record, factually, so I would help with that with some [00:31:00] of the legal arguments. I remember at one point they called and we had a conference call with Seth and three lawyers from Wilmer Hale, and I’m on the phone in the office of my prison counselor, and they’re asking and saying, “Argument’s next week. Are there any questions that you think the justices might ask that we’re not thinking about,” and I just remember thinking, “I’ve been self studying the laws for 18 months with no undergrad degree, no law school and here I’ve got a former Solicitor General asking me [00:31:30] questions like this. My response was, “I have no idea.”

Trevor Burrus: Of course, that wasn’t the first time, though, because then you had a second petition.

Shon Hopwood: Yeah, then I had a second petition that was granted in part because the lawyers from Wilmer Hale stayed in contact with me long after John Fellers case was over and so they gave me the heads up that there was another case in the court that was similar to one and I was taking up with a friend of mind, and it was because of that that I kind of tied the case I was working [00:32:00] on to that case, and when that case won, my guy won and got remanded back.

Trevor Burrus: That was just a GVR?

Shon Hopwood: Yeah, a GVR, and then I started winning cases [crosstalk 00:32:11]

Trevor Burrus: Grant, vacate and remanded is what that means.

Shon Hopwood: Yeah. I started winning cases all over. Federal district courts, I won a case in the Sixth Circuit Court of Appeals, and the least couple years, I was basically running a law firm from prison where I’d have 10 clients at once, and one prisoner who woke up every [00:32:30] day and basically went to the typewriter and typed out briefs that I was drawing on my hand.

Trevor Burrus: You had paralegals that assisted you and were working for you.

Shon Hopwood: Yeah, I had a staff.

Trevor Burrus: Who was your staff? I’m thinking of like prison nicknames, so this is …

Shon Hopwood: That would’ve been Glen. He was a guy from Nebraska in on an interesting case because he was a white guy in on a crack case, which I don’t think I’d ever seen that happen before. He and his brother were there, twin brothers from [00:33:00] Omaha, and he was good at typing, and so the guys that wanted me to do work would just pay him to type out the briefs so that I could sit in my cell and continue writing.

Trevor Burrus: Did you teach other people how to do legal research and things like that?

Shon Hopwood: Yeah, I taught a couple classes in the education department. Prison was a little skittish about that just because they want people to learn the law but not to well, and one of the things that I realized early on was [00:33:30] if I stuck with working on criminal cases, the prison pretty much left me alone. It’s when you start suing prison guards on civil rights cases that things can go really bad.

Aaron Powell: I’m curious. You’re doing all this legal research and writing. Did you have access to Westlaw or LexisNexis?

Shon Hopwood: I wish. I wish. I probably appreciate Westlaw like no human being on the planet. No, it was all books. [00:34:00] It’s not an exact science, so you have to read basically 100 cases for every two that you find that are on point, which is not very affective and is very time consuming, but for someone that doesn’t know the law, it required me to read a whole lot of law that wasn’t relevant to the case I was working on, and I was like a sponge, so it actually, in the long run, made me a really good lawyer, but I wouldn’t recommend it to anyone.

Trevor Burrus: You touched on this [00:34:30] a little bit, but it seems that with the stories you tell when you talk about, I think his name’s Marvin.

Shon Hopwood: Marvin Brown.

Trevor Burrus: Marvin Brown, just people in unfortunate circumstances, and you get the sense, and you’ve done this so much, but that so many of these people in federal prison are there with bonafide legal complaints in the sense that there are all these pro se … We know about the prison lawyers and everyone wants to roll their eyes and say, “Okay.” Well, [00:35:00] you have the hard criminal justice, the hard law and order people saying, “Oh, well then the prisoners are going to file like 50 appeals on the stupidest things,” but you get this sort of sense that there’s a lot of bonafide legal complaints, especially given the fact that probably defenders [inaudible 00:35:15] are so strapped for time that they overlook things constantly.

Shon Hopwood: They are, and it takes a lot of dedication to litigate one federal case appropriately. Today, that’s still [00:35:30] my favorite case I’ve ever worked on. Melvin came to me two weeks before his habeas petition was due and said, “Hey, look at this.” He had been sentenced as a career offender at the age of 22. How you’re a career offender at 22, I don’t know, but he was a young African American man who’d been caught with three grams of crack and was given a 16‐​and‐​a‐​half‐​year sentence in federal prison and the problem was that one of his prior convictions didn’t actually count, and the career [00:36:00] offender was really because he pled guilty, that was the only part of the case that really mattered.

The lawyers and the probation office just didn’t look at it, and when we filed it, the judge ordered the probation officer to respond first before the US Attorney’s Office. The probation officer just came back and said, “We missed it,” and the prior lawyer said, “I missed it.” Then the government came back and filed a one‐​page response that said, “We agree. He needs to be re‐​sentenced,” and he was re‐​sentenced [00:36:30] to five years and eight months.

Trevor Burrus: If you hadn’t had gotten involved, that would not have happened.

Shon Hopwood: He would still be in prison.

Trevor Burrus: He’s not in prison anymore?

Shon Hopwood: He’s not in prison anymore.

Trevor Burrus: Do you know‐

Shon Hopwood: He bought me a typewriter ribbon and a copy card.

Trevor Burrus: Fourteen dollars, I think you said.

Shon Hopwood: Yeah. Yeah. That was 14 dollars he got almost 11 years shaved off his sentence.

Trevor Burrus: How many people do you still talk to who are still in prison? I know your friend, John, or people who have been released. Do you still make contact [crosstalk 00:36:59]?

Shon Hopwood: Oh yeah. I’m in [00:37:00] contact with quite a few of them. Most of my closest friends got out, never committed a never crime. Never had any problems again and never went back. There are some that have gone back, but I tend to keep in contact with all those guys. I lived with them in a very intimate setting for 10 years, so they are, in some ways, like family to me.

Aaron Powell: Your path after prison has been pretty interesting.

Trevor Burrus: [00:37:30] So?

Shon Hopwood: Yes.

Aaron Powell: What happened after you got out?

Shon Hopwood: I’m just a normal law school student.

Trevor Burrus: Absolutely, yeah. What year did you get released?

Shon Hopwood: I got released to a federal halfway house in October of 2008, height of the recession. No one finding work, let alone the guy that just did 11 years in federal prison. I quickly realized not a great need for knowledge of the US Supreme Court in Omaha, Nebraska even [00:38:00] amongst lawyers. They just aren’t filing many briefs to the Supreme Court. I couldn’t get a job with lawyers or law firms, but I found this job for a document analyst at Cockle Legal Briefs, which is this company that prints Supreme Court brief for lawyers all over the country.

Trevor Burrus: Something we are familiar here with at Cato. We work with it all the time.

Shon Hopwood: I know, I know. That’s where I first learned about Cato, was working at Cockle. I worked there and I worked on a case with a professor from Michigan, [00:38:30] Rich Freedman, who was litigating a confrontation clause case and he asked me one day and said, “You know an often lot about the confrontation clause. You must be a lawyer because this isn’t something that one studies for fun.” I said, “Well, I’m not a lawyer, Rich, and I’ll tell you some day about my story, but don’t freak out.”

I wrote him a really long e‐​mail and told him, and he did freak out, but in a good way. After he argued his case in the Supreme Court, he told Adam Liptak at the New York Times about my story.” [00:39:00] Adam wrote the story in February of 2010, and life hasn’t been the same for me ever since.

Trevor Burrus: You did end up going to law school.

Shon Hopwood: I did end up going to law school at the University of Washington and got a full‐​ride scholarship through the Gates Public Service Law program there, and then after that, I went to go clerk for Judge Janice Rogers Brown here in DC on the DC circuit.

Trevor Burrus: It’s a shock. Every turn [00:39:30] in the story just gets crazier and crazier. Having lived it, it must feel that way.

Shon Hopwood: It feels that way to me. It really does. There are moments I wake up and feel like, “I can’t believe this is happening,” and I’m the one living it, and it’s unbelievable.

Trevor Burrus: There’s even a love story in it. It’s all. It’s unbelievable.

Aaron Powell: Now you’re at‐

Shon Hopwood: Now I’m at Georgetown at the Appellate Litigation Clinic, which I’m just finishing up a teaching fellowship there where we have 16 students and we take cases on appointment [00:40:00] to the 11th Circuit, the Fourth Circuit and the DC Circuit. I’ve argued a few cases and just a few weeks ago prepared one of my students who argued in the DC Circuit before Judge Brown. Yeah, it’s been just … It’s one of the funnest jobs I’ve ever had.

Trevor Burrus: In law school, did you do clinic work and stuff to continue helping … Are you still focusing on the prosaic kind of side of things?

Shon Hopwood: I did, so I did the innocence project, but I was [00:40:30] also moonlighting as an appellate practitioner through law school. I wrote a lot of briefs for other lawyers of law firms without my name on it.

Trevor Burrus: I know exactly what that feels like.

Shon Hopwood: Yeah, yeah.

Trevor Burrus: Because that’s what I’ve been doing here for seven years, yes.

Shon Hopwood: I would tell you that there was one petition I prepared basically all in class sitting in the back row. I don’t learn very well by lecture, so I would get bored very quick, and so I would start writing briefs in the back row. [00:41:00] Not something I would recommend of my students, but it worked for me.

Trevor Burrus: You also had two kids.

Shon Hopwood: I also had two kids. My son was born the first year I was out of prison and my daughter was born the second day of law school, and now my wife’s in law school at Catholic University.

Trevor Burrus: Oh, really? Is she going to try and pursue a similar type of …?

Shon Hopwood: She is. She wants to work on prisoner cases and criminal cases. She’ll probably do some appellate work with me and [00:41:30] it’ll be good times.

Trevor Burrus: What is the plan at Georgetown? Will you be helping build out the awareness? Is that part of the clinical stuff or awareness of the plight of prisoners in the pro se world?

Shon Hopwood: Yeah, so I’m getting ready right now to make the transition from clinical faculty to full‐​time tenure track faculty, which means I’ll be writing a lot fewer briefs and writing more law review articles, but Georgetown was pretty [00:42:00] aware of what I wanted to do when they hired me, which is teaching and writing scholarship.

The other component is sentencing reform, especially federal criminal justice reform since Georgetown’s literally three blocks from the hill, and then if there are opportunities for litigation where I feel like I can make an impact, I will continue to do some of that as well. I really enjoy arguing appellate cases on behalf of one client, one criminal defendant, and so I don’t think [00:42:30] I will ever fully get away from that.

Aaron Powell: Did you ever consider becoming an attorney, a defense attorney in the private sector?

Shon Hopwood: No. I thought about becoming a public defender, but I worked for the federal defender’s office in Seattle one summer and I really enjoyed the work, but what I realized was it was really hard on me to go to sentencings and be seated next to the client because I know, unlike everyone else in that building, exactly the sort of punishment [00:43:00] that client’s going to face and that it doesn’t end once they’re done with prison.

When we moved from Seattle to DC, I was denied, my whole family was denied apartments at various places because of my felony background, so I know the punishment these men and women are facing, and that was just really hard for me to do that day in and day out.

Trevor Burrus: What do you think most people should realize about the criminal justice system that they don’t currently realize?

Shon Hopwood: How completely arbitrary it [00:43:30] is, especially the federal system. Who gets charged federally and who doesn’t is completely arbitrary, and then even built within that, there’s a lot of arbitrariness about how Congress writes statutes. I just wrote a law review article on this about how many of them are vague and ambiguous and courts tend to always expand statutes to cover the crime rather than narrow them.

Some of the people that get [00:44:00] caught up in it aren’t much different from the person that gets charged in state court and gets a year or two in prison and is released and the person charged in federal court does 10 or 20 years.

Trevor Burrus: What do you think people can learn from your story?

Shon Hopwood: Well, what I’d tell them is everyone goes through pretty profound changes between the ages of 20 and 40, like 20 when I committed the crimes, 40 I’m now Dad, husband, and if we know that, we know that people make profound changes, [00:44:30] why do we think prisoners can’t? If the answer is, “One, people that commit crimes are inherently evil,” then we have to root out that fallacy.

If the other answer is, “Well, the prison system makes it so people can’t be redeemed because it makes criminality worse, not better.” Well, then that says something not about those individuals, but about our criminal justice system and it’s failings.

Aaron Powell: Do you think that there are meaningful opportunities [00:45:00] now for reforms for criminal justice reforms? Sessions seems to make it harder, but do you think that … Are you optimistic at all?

Shon Hopwood: I am, especially at the state level because I think a lot of the states have had success in pairing back their criminal justice system while at the same time their crime rates have not gone up, which is always … I don’t think there’s a great correlation there, but politicians tend to look at things like that and make the correlation regardless.

[00:45:30] I don’t think this administration is going to put much of a dent in that. On the federal side, I don’t know. Part of me thinks with Sessions as attorney general, it will be hard, but on the other hand, at least he’s not still in the senate, so he kind of killed the bill the last time around and at least he won’t be there anymore. I’d like to think that if people just understood it a little better, that they would realize that this [00:46:00] is kind of a win‐​win for everyone.

Trevor Burrus: Thanks for listening. This episode of Free Thoughts was produced by Tess Terrible and Evan Banks. To learn more, visit us on the web at www​.lib​er​tar​i​an​ism​.org.