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A Discussion with Former Acting Solicitor General Neal Katyal

by Everlaw


It’s rare to have the opportunity to sit down with an industry titan, let alone someone who has more Supreme Court cases under their belt than any other minority attorney that preceded them. You may have seen Neal Katyal on TV, discussing major court cases, explaining the impact of new legislation, and lending his legal expertise to pundits on both sides of the aisle. When the chance came to have a conversation with one of the legal industry’s defining leaders, we jumped at the opportunity.

In this interview, Neal goes over his experiences arguing cases in front of the Supreme Court and how he prepares for big cases.

AJ Shankar 

Neal, thank you so much for joining me today. I know the last few weeks — months even — have been a really busy time for you.

Neal Katyal

Thanks, AJ. I’m looking forward to our chat today.

AJ Shankar

Alright, let’s dive in. In your recent TED talk, you spoke about your experience arguing in front of the Nation’s highest court. In that talk, you said, “You don’t just need the right argument; you need the right argument at the right time.” Could you expand on your process of developing the right argument and how you push forward when you know it’s not the right time?

Neal Katyal

There are two questions there: one, how do you develop the right argument? And the second: how do you think about the timing? With the right argument, I think the thing that lawyers and, frankly, even non-lawyers, don’t do enough in this polarized age is to have a team of people who think differently; it was a lesson I learned early on. I was a pretty knee-jerk, leftie law student, and I spent my second summer break working in Washington, D.C., at the Solicitor General’s office. There was a phenomenal conservative lawyer there at the time named Miguel Estrada. He was my boss and mentor, and at the end of the summer, I asked him, “Miguel, I have one more summer. What should I do?” And he said, “Go to Hogan & Hartson and work for John Roberts.” This was before he was a jurist and back when he was running that Supreme Court practice. I wrote him a letter that said Miguel suggested that I should work for him.

From there, I met with Mr. Roberts for an interview, and we had a nice, regular interview. At the end, he says, “Do you have any questions for me?” I said, “Look, you know, I’m a really leftie law student. Do you really want to work with me?” I remember his reaction because it was so profound. He looked at me and said, “Neal, that’s why I’m interviewing you. I want you here because I want to learn from you. I know how I think; I want to know how others think.” Since that moment, I’ve tried to build that into my teams. I believe we get a much better product by having a team of diversity along all dimensions, not just race or gender, but that’s obviously incredibly important, too.

The timing component is hard to know, particularly at the Supreme Court stage. You do have some control as an advocate over timing: how much you want to push to bring a case to the Supreme Court, how quickly, and how big that case is. I think we’re all thinking about this a lot in the last couple of weeks because we’re mourning the loss of Justice Ginsburg. Before she joined the Supreme Court, Justice Ginsburg was a master litigator who knew how to bring a case, when to bring it, how much to push for, and who to use to push for it. In sex discrimination cases, she brilliantly thought it best to push for change incrementally, following the litigation strategy of Thurgood Marshall with respect to racial justice issues. You don’t just walk in on day one and say, “schools should be desegregated — K through 12.” You build up to that over time.

So, the problem is that as advocates, it’s hard to know what the court is thinking about a particular set of issues. I was privileged to be part of the marriage equality cases, and there was a bitter fight. Some people thought, “don’t bring the case too fast.” Others said, “look, you know, people will die not being able to get married.” Ultimately the timing on that one was right; the country and the world are so much better off for it — what a remarkable achievement by those attorneys. I mean, it just brings tears to my eyes to think about it. Sometimes you get it right, and sometimes you get it wrong.

You’re just trying to get all the information in, reading every word and studying the oral argument transcripts for clues. So that scenario is a really good illustration of how there’s going to be more and more data generated, even in the stuff that people don’t think about, like Supreme Court oral arguments. For the next generation of advocacy, it’s going to be critical to be able to use that data effectively. 

AJ Shankar

Even with all the preparation, it’s still you there on the podium, or now it might be over a Zoom call. There’s a huge amount of practice that goes into getting good at arguing cases. It’s more of a chess match, where you have to react on the spot in any direction. How do you prepare mentally and physically for that moment, at the culmination of all this research? Is there anything you do, even on game day, to get ready? 

Neal Katyal

First of all, you know, in my practice of 15 Supreme Court and appellate advocates, I’m certainly not the only one up there. We try and get everyone up at the podium every year, all 15, even the most junior attorneys. That’s because the only way they can prepare me, frankly, is if they’ve done it themselves.

As you say, it is a chess match; it’s not a prepared speech. Sometimes when you put people, even the most brilliant, in the role of an advocate, they’ll write a brief that papers over the hard issues because they think it’s more persuasive to ignore the stuff against you. It’s only if you’ve stood at the podium when your brief has papered over a hard issue that you know you can’t get away with that in the federal courts.

There isn’t an ability to try and obfuscate; you’ve got to grapple with the hard questions early on. So the first step is developing a team that doesn’t just have diversity in it, but that has actual court experience at every level.

Typically, I also take notes on the case and create an argument binder, which has every issue in the case as a separate kind of big bullet point. The binder will usually run about 50 pages of single-spaced notes. From there, I create a one-page cheat sheet.

I remember one case involving the Bagram Air Field, where I had to get the wording just right; otherwise, there could have been foreign policy consequences. So with something like that, I will open up the binder instead of looking down at that cheat sheet. I find it really helpful to have both that binder and the one-page cheat sheet.

The final step and my secret sauce is my moot court program. I relentlessly practice first with my team, then with outsiders. In my first case, Guantanamo, I did 15 moots. I videotape my moots and watch them afterward. Then, I convert them to an MP3 and usually exercise, like, jog or something, and listen to them in an environment where I can’t look at anything else. Basically, I’m just out on the running trail, and that forces me to go word by word and listen. Is that how I want to say it? Is there a shorter way to say it? Is there a more powerful way of saying it? I’m trying to think through all of those issues.

AJ Shankar

What does it feel like to be ruled against by the Supreme Court?

Neal Katyal

Well, it depends on the case for the most part. Again, if I felt like I’d done everything I can, it’s fine; I’ve done my job. There are times when it’s really hard, and I talked about this in the TED talk that you mentioned.

I really cared about the Muslim ban case and brought the first one. The great Attorney General of Washington State filed the lawsuit and won so that one was removed right away. Then there was a new [travel ban], and I represented the state of Hawaii.  

We went right into court and got that struck down. The president said, “See you in court… illegitimate ninth circuit…” Two weeks before the oral argument at the Supreme Court, I think he got scared and pulled travel ban two back and replaced it with travel ban three.

It allowed the president’s lawyers to say that travel ban three was different. But nonetheless, we got it struck down at the trial court, at the court of appeals, and lost five to four at the Supreme Court.

That was an incredibly hard loss for me. There wasn’t a moment that I believed that we would lose. I just thought this was so fundamentally unconstitutional, un-American. It was such a betrayal of our founding ideals.