Cross: Shon Hopwood, From Prisoner To SCOTUS To Scholar

June 22, 2016 (Fault Lines) — Ed. Note: Scott Greenfield and David Meyer-Lindenberg cross Shon Hopwood, one-time jailhouse lawyer who won before the United States Supreme Court, turned lawyer, scholar and graduate teaching fellow at Georgetown Law School’s Appellate Litigation Clinic.

Q. You grew up in a small town in Nebraska, David City, where you were a high school basketball star, good enough that you won a scholarship to Midland University. But in 1994, you dropped out to join the Navy. Why did you trade Nebraska for Bahrain? You had the ticket to the American dream, and chose to walk away? It obviously wasn’t because you lacked the intelligence to succeed, so what drove your choice to leave? And why choose the alternative of the Navy? Was there a sailor inside you yearning to be set free?

A. I didn’t voluntarily leave Midland. I was kicked out of school. As a college athlete, you only have time to do so much. It is very difficult to both go to school, practice and then party. I chose the latter two. I never enjoyed school and academics; I was a solid C student all through high school. It wasn’t until I discovered the law and started researching legal problems and writing out solutions that I finally began to relish things of an academic nature—probably because postconviction and appellate work melds helping people (the extroverted part) with thinking about various arguments and framing devices (the introverted part). I like the mix.

As for the Navy, that choice was born out of necessity. I had been kicked out of college and my parents wouldn’t allow me to move back in their home (good for them). I rented a dilapidated apartment in my hometown for $200 a month and went to work at a factory. Doing the same job over and over again was, for me, a form of torture. So I decided to go see the world and the Navy offered that. My dad also thought the Navy might teach me some discipline, which I sorely needed. But even the Navy couldn’t break through my foolishness.

Q. In 1996, you nearly died from pancreatitis and were honorably discharged from the Navy. By your own account, you ended up back home, underemployed, depressed and addicted to drugs and alcohol. What did your future look like to you at that point? When your best friend from high school invited you to rob banks with him, you said yes. You and your friends robbed five banks in the Omaha area before you were done. Were you any good at it? What did you spend the loot on? And at the time, did it give you a sense of purpose you felt you were lacking? How did you think it would turn out?

A. I actually came back home worse off from the Navy than before I left. I had no idea what I wanted to do with my life, and I struggled through a series of dead-end jobs. I had gotten myself in trouble for attempting to forge a check. I was also hanging around other people who were as moronic as I was. We spent weekends drinking and chasing after girls. I was an idiot, to say the least.

And then my lifelong friend asked me to a bar one night and, while we drank watery beers, he asked if I would help him rob a bank. Most people would have laughed it off, maybe said, “you’re crazy,” or even, “no.” But not me. In my immature mind, it seemed like a solution to my problems.

I was not a good bank robber. The longer it went, the sloppier I got. By the last robbery, I left a palm print on the getaway car. I just didn’t care anymore what happened to me.

I never had any illusions about how it would turn out. I expected to end up caught or dead. I often told my friends that when the police came for me, I hoped they’d end it with a bullet to my brain. Those claims weren’t hyperbole. That was my plan. To live the fast life until law enforcement found and killed me. I sure was stupid.

Q. Two years later, you were caught when one of your friends snitched. You pleaded guilty to five counts of bank robbery for 87 months in prison, and one count of use of a firearm for another 60. What goes through a 23-year-old’s head when he’s staring at over 12 years in prison? Were you angry at the judge, your friends, yourself, the world? Did you realize what it meant to face what’s euphemistically called “prison culture”? Did you think your life was over?

A. I, like most people in their early 20s, couldn’t fathom what 12 years meant. It may have been a life sentence, for all I knew. I remember thinking that I’d be 30-something when I got out, which meant I’d be really, really old! For the first few years in prison I did think my life was over. But then I got a little older, a little wiser, educated myself, and realized it would be way more fun to prove to everyone that my life wasn’t over than to prison. So I never held any animosity towards Judge Kopf, my sentencing judge.

Q. Shortly after you got to Club Fed, you started working in the law library. Though you’d had no legal education, you discovered you had mad skillz for understanding court cases and following legal arguments. After you learned about § 2255 motions, you filed one, invoking the newly-decided Apprendi v. New Jersey in an effort to get your sentence reduced. It didn’t work out. Were you discouraged, or motivated to keep trying? What made you decide to be a “jailhouse lawyer”? What was in it for you? In your memoir, Law Man, you write about the brutal prison environment. What impact did it have on pursuing jailhouse law? Any cognitive dissonance involved in learning the sanitized version of the criminal justice system compared with the reality version you lived?

A. Being a jailhouse lawyer isn’t very glamorous. It meant long hours reading Federal Reporters and pecking out a brief draft on a typewriter. At least, that’s how it was for me. I might have gotten frustrated had the Fellers case not happened. It is very frustrating to write a brief with meritorious issues only to be rejected out-of-hand because the petition is filed pro se. And I watched that occur with regularity during my time as a jailhouse lawyer. But the wins kept me motivated. And later on, when I had a budding friendship with my now wife, I was motivated to learn more about the law because I was hoping to have a career as a paralegal when I got out of prison.

As to the cognitive dissonance, yes the actual criminal justice system is much different than most realize. Very few people understand all its dimensions well. And, unfortunately, academics and appellate judges probably understand it less than most. It’s not their fault, though. Academia and the federal judiciary reward rule followers, so I think it is difficult for them to understand that many, maybe even a majority of Americans are not strict rule followers. So how do we design a system taking that into account? I don’t think people who have spent the majority of their life making decisions to get a seat on the Supreme Court or Harvard law faculty necessarily have the best answers.

Q. In 2002, a fellow prisoner, John Fellers, approached you about his case and you agreed to help him out. As his “jailhouse lawyer,” you petitioned the Supreme Court for review, and in extreme defiance of the odds, they granted cert. That’s a huge accomplishment for an attorney with years of experience. For a self-taught prisoner, it borders on the fantastical (I called you a “freak of nature,” which made you bristle). Seth Waxman, a former Clinton solicitor general, agreed to handle oral argument on condition that you be involved. Together, you won a unanimous decision: Fellers’ case was remanded on Sixth Amendment grounds. What was it like, preparing for a Supreme Court case from a prison cell? Waxman kept you closely involved; what were your responsibilities? Did you appreciate the significance of what you were doing? And what does a prisoner say to himself when he wins at the Supreme Court?

A. Freak of nature sounds like something I should have tattooed on my back! Getting cert. granted as a jailhouse lawyer may, no matter what I do as a lawyer for the next thirty years, rank as the singular best accomplishment of my career. Which sucks. Nowhere to go but down! That said, I probably wouldn’t have a legal career now had that not happened for me twice.

My big break occurred when Seth took over the Fellers case. I think most people of his caliber (former Solicitor General, Harvard undergrad, Yale law school) would have said, “hey, Mr. Jailhouse Lawyer, thanks for getting cert. but I will take this over now.” Anyone other than Seth might not have kept me involved. But Seth did. I called him and he answered. He sent me drafts of the merits briefs and I’d send notes back to him. And at one point, I had a conference call with Seth, Noah Levine, and two other lawyers from WilmerHale, so that we could discuss oral arguments. I appreciated the significance of Seth’s graciousness, but I don’t know that I truly understood how strange it was to litigate in SCOTUS as a jailhouse lawyer.

Q. After Fellers, you were unsurprisingly in demand as a jailhouse lawyer. Were you able or willing to help everyone who came to you? How did you deal with hopeless cases? More broadly, do jailhouse lawyers deserve their rep? Were you the one guy who wasn’t incompetent or trying to scam people? Are all jailhouse lawyers entitled to a presumption of good intentions and competency? The flip side is that there are few avenues other than jailhouse lawyers for prisoners, especially poor prisoners, to pursue post-conviction relief. Is there a tipping point between jailhouse and practicing lawyers? What should private lawyers do to fill the hole?

A. Jailhouse lawyers aren’t that different from normal lawyers. Are there scammers and the incompetent? Yes. But the same is true for lawyers. Some of the worst degenerates I saw and still do see are the lawyers paid to do prisoner post-conviction motions. The only bar that is worse are immigration lawyers.

Most jailhouse lawyers don’t intend to be incompetent. They just don’t know they are. There is a rather big incentive to not be an incompetent jailhouse lawyer. I once watched a jailhouse lawyer really mess a case up and the judge wrote something about the inadequacies of the filed brief in the judge’s order. The next day the jailhouse lawyer woke up to his client swinging a padlock inside a sock. Padlock breakfast burritos are not something that concerns lawyers.

Jailhouse lawyers are not a long-term solution to a lack of representation. They just aren’t. Society needs to adequately fund public defenders and other groups to fill in the gap. Pro bono lawyers aren’t the answer either. Most noncriminal lawyers can’t adequately represent a criminal defendant. Some criminal trial lawyers can’t adequately represent a client on appeal. And some appellate and trial attorneys know nothing about habeas practice. In Law Man, I recount a story about a lawyer appointed by a federal district court judge to represent a friend of mine after we had filed my friend’s habeas petition. I called the lawyer one day and he said he was going to voluntarily dismiss the petition because it was untimely. I ended up screaming at this lawyer when he wouldn’t listen as to why the petition was timely filed (the prison mailbox rule). I had to threaten to file a bar complaint before he finally relented.

Q. After you were released in ’08, you went to school at Bellevue, hoping to become a paralegal. That changed when you got a full scholarship to the University of Washington School of Law, courtesy of the Gates Foundation. How did that happen?  What impact did your criminal record have on your decision to go to law school? On Day 1, who walked into the classroom, with those bright-eyed, bushy-tailed, sheltered budding lawyers?

A. I decided to apply to the University of Washington School of Law after Professor Eric Schnapper called me. Eric was one of my employer’s biggest clients (Cockle Legal Briefs) because he often litigates cases in the Supreme Court. Eric encouraged me to apply and said I should come to school there. I applied to school and to the Gates Program, and I was chosen as a Gates Scholar after two days of interviews in Seattle.

Going into a classroom where everyone knew my story but I knew no one else’s was difficult. At first, I had this awareness that maybe I shouldn’t be in law school. But after I realized everyone else had the same feeling, I quickly reversed course and just got down to business. I don’t remember a lot from those first few months other than my daughter Grace’s birth, living in a new city where we knew no one, and working on a series of Supreme Court filings (three briefs in total) that I had been paid to write in the summer and of course things got extended into the school year.

My classmates made school many times better. Especially my small section. They taught me about all things millennial and I taught them about how to make a shiv out of a toothbrush or a homemade tattoo gun from a beard trimmer. With apologies to my professors (who were also wonderful), we had long running threads on Facebook that occasionally heated up during class. I’m a trash talker and sometimes my classmates brought out the best in me!

Q. At UW, you interned with Judge John C. Coughenour of the Western District of Washington. Then you got one of the most prestigious clerkships in the nation when you signed on with Judge Janice Rogers Brown of the D.C. Circuit Court of Appeals. You’ve kept pretty quiet about your time with Judge Brown, in particular. Not to highlight the brutally obvious, but the juxtaposition of inmate and circuit court clerk is pretty stark. Did the judges “get it”? Did you bring the baggage of your experience, or were you now part of the sanitized world of federal law clerks? Seeing how the sausage was made, did it change your view from the cell? Did you change the judges’ view?

A. I have been quiet about my time as a clerk for one reason. In my view, clerks should be what my dad said about children: “seen but not heard.” So I don’t speak publicly about my time at the court.

I can tell you that Judge Brown is a treasure. I have never met a more genuinely humble lawyer, let alone a more humble federal judge. We often talked for an hour about the law and life, and I cherished those conversations. She never once treated me any differently from anyone else. If it’s not completely obvious, I adore her. I miss working for her.

Whenever we had a D.C. Circuit clerkship happy hour with clerks from other chambers, I always felt out of place. Every happy hour felt like a Yale and Harvard law school reunion because those two schools placed the majority of clerks on the D.C. Circuit. Yet the other clerks and judges were always very nice. It was a wonderful job.

Q. Now you’ve graduated, published numerous law review articles, gotten an LL.M at Georgetown Law and a fellowship at its Appellate Litigation Clinic. How do you balance your teaching and litigation responsibilities? How did your past prepare you for helping 3Ls get their chops? Are they up to it? What do you see as the most significant hurdle for law students to overcome? Do you give them a reality check as to what it means to be entrusted with another person’s life? Do they get it? And what’s it like for a former federal prisoner to rep federal prisoners in federal court? Are you considered one of them, one of us or something in between?

A. My boss, Steve Goldblatt, is old school in his belief about clinic pedagogy. It’s a belief I share. We don’t send out bad briefs on behalf of real clients, even if that means we need to rewrite large parts of it because the students aren’t up to snuff. We of course work with the students the best we can. Which means editing at least four or five drafts. But sometimes we need to take it over. So that is the balance. I hope to get better at it this year.

The biggest hurdles for students are the same for practicing lawyers. Writing and analytical skills. Students haven’t read hardly any briefs by the time we get them, so they don’t understand how to write. Just like many lawyers, students tend to use lots of “lawyerly” words and convoluted syntax. And, just like lawyers, students have difficulty when there is no binding precedent and they have to create their own arguments for why the court should rule in favor of their clients. I often tell them that in many of our cases it is not enough to throw handfuls of precedents at the court in the hope that one sticks; it takes persuasive arguments.

My relationship with my clients depends on the client. Some of my clients don’t know my backstory. To them I’m just another lawyer. But some of my clients are guys I was in prison with. They’ve been waiting patiently for me to be in a position where I can really help them. My first case with the clinic here was a case I brought to the clinic. A friend of mine is serving 20 years for felon in possession of a firearm, so we filed for a second or successive 2255 petition in the Eighth Circuit and it was granted. He is now litigating for the chance to be resentenced and immediately released. My conversations with him aren’t much different from what they were in prison. I seem to occupy this strange place where I have one foot in and one foot out, and I’m perfectly okay with that.

Q. And then there’s that mean-ass old judge who sentenced you, and who denied your § 2255 motion, all those years ago. That would be Fault Lines’ own Judge Richard G. Kopf, who has since become one of your strongest supporters. You’ve even given interviews together, where Judge Kopf said his sentencing instincts about you back in ’99 “sucked” and were totally off the mark. Have you come to terms with this? What influence has this had on your view of the system, the judiciary? Does this make it better or worse? And your legal scholarship shows you to be a strong critic of things like AEDPA, which Judge Kopf has vigorously defended. What’s up with that old judge? Will he never learn?

A. There really isn’t anything to come to terms with. I harbor no ill will against Judge Kopf. Never have. The fact that he thought I’d never amount to much wouldn’t separate him from most people that knew me in my early 20s. All of us have the capacity to change. Even prisoners. And even me.

As to AEDPA, Judge Kopf is just wrong. Totally and utterly and completely wrong. So says the now academic to the district court judge! That was a joke, by the way.

4 thoughts on “Cross: Shon Hopwood, From Prisoner To SCOTUS To Scholar

  1. Richard G. Kopf

    Dear Shon and SHG,

    For both obvious and not so obvious reasons, I will treasure this interview until the day I die. Thanks to you both.

    With the highest regard for both of you, I remain,


    Rich Kopf

    1. Wrongway

      “All of us have the capacity to change. Even prisoners. And even me.”

      Judges Too ??

      PS: Hows the Skiing in Nebraska these days ??

      1. Richard G. Kopf


        Oh, yes, judges do change but the changes, at least in my experience, are subtle. Probably, they are also subconscious.

        Relatedly, what lawyers and lay people don’t seem to understand is that being a federal trial judge is really no different from laboring at the AP parts plant where I once worked. There is an endless supply of Chrysler tailpipe to bend or federal cases to resolve and they come at you one after the other. The supply is unceasing. You have very little time or strength for navel gazing.

        As for skiing in Nebraska, this spring you could water ski down the streets. Snow skiing remains a challenge unless you are pulled at high speeds beyond a four-by-four pickup like every kid in the Nebraska hinterlands has done to the horror of their moms and dads.

        All the best.


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