Interview: Tom Goldstein

by Anna Salvatore

Tom Goldstein is the co-founder of SCOTUSblog. He’s also an experienced oral advocate, as he has argued forty-two Supreme Court cases in the last twenty years. Just last month he represented the respondents in Air and Liquid Systems Corp. v. Devries. I’m psyched that he agreed to talk with me about his teenage years, his internship for Nina Totenberg, and his recent challenge to the Attorney General’s appointment.

My questions are in bold; his answers are in plain text.

I read that when you were 13, you typed up a CV and asked your local computer store if you could work there. How did the store employees react when you handed them that CV?

Well, it’s always been my experience that if you say to someone, “I want to work for you, and I’ll do it for free,” or “I’ll do it for food,” that they’re pretty happy for the help. So I think they were fine with it, so long as I stayed out of people’s way and didn’t try to overreach. I worked every Saturday for a Chick-fil-A sandwich. I’m sure it was entirely illegal, but it was a good experience for me.

What was your prior computing experience? 

There really wasn’t a lot of computing experience to be had. This was the birth of personal computers, so these were the very first Apple personal computers and the very first PCs that were coming out. And so nobody had a lot of experience. That is to say, I had just as much experience as anybody else. I mean, I had a computer, and I played with it — that sort of thing. But I actually was as interested in the sales part of it as I was the substantive computing. I was never anything like a hardcore coder. I never worked inside the boxes, taking them apart and fixing them. It was always bigger picture and sales.

How did selling computers improve your public speaking skills?

You know, if it had any effect, I suppose it was just in being comfortable in a lot of different situations. The law has a sales element to it, both in terms of advocacy and building the business. It may well have just reflected something about my personality to begin with: that I’m comfortable doing that. But at the very least, it certainly didn’t hurt.

Were your parents similarly comfortable talking in front of other people? 

No. Not at all. My dad was a doctor, my mom a lawyer, but never in roles like this. They both had their practices, but it wasn’t that they sought out an audience. They were much less attention-seeking than me.

My mom was a contract lawyer, mostly for the Port Authority of New York and New Jersey. Her work was never something we really got into the weeds about, because it tended to be highly technical legal agreements on behalf of the Port Authority. She also did some Russian trade work. So my work as a lawyer never really followed, say, in the footsteps of my mother as a lawyer. We’ve always done very, very different things.

What were you like as a teenager? 

My big thing in high school was debate. When I was a high school freshman, we were in Florida, and I went to a high school that it’s big thing was debate. So I was really lucky in the sense of getting that exposure. Then we moved to Columbia, South Carolina, and my dad and stepmom were able to pick out a high school that had a debate program. When I got there for the final three years of high school, it completely consumed me. So that’s really what I did. I had some friends, of course, and did the usual things, but I spent my academic year doing debate. The rest of the time, I continued to do computer-related work: either computer sales or other kinds of computer administrative stuff.

In a typical school week, how much time would you spend debating?

All of it. [laughs] Both in high school and in college, I really threw myself into that. School was kind of secondary to the debate work that I did. I can’t even calculate it. All of my free time, probably.

It’s probably hard to pin down, but why you were so attracted to debate?

I don’t know. Probably the same things that drive me to really love the law. I love the analytical problems, and working through them, and then the advocacy. It’s junior-varsity law. And so I always knew I was going to be a lawyer, and I always knew that I’d focus on debate in high school and college.

How did your debate tournaments compare to your current oral advocacy?

They’re radically different stylistically, because that was an era where it was policy debate and team debate. There were two of us, and we would talk really fast and try to make as many arguments as we could. But in terms of the skill set, it was pretty similar. That is, doing a lot of research, breaking down problems, constructing arguments, figuring out the priority of arguments, how arguments interact with each other… that was real training for the work I’ve done as a lawyer.

What were some valuable pieces of advice that you received in debate?

I think probably the one lesson that was told to me in debate, in high school and college, is don’t be too tricky. Try and be more straightforward. Try not to be slippery in your argumentation.

And I suppose another lesson I’ve learned from that process was to appreciate the strength of the other side’s arguments, and to expect that the other side will come up with the best possible arguments. That’s been particularly relevant at the Supreme Court, because the lawyering on the other side is done at a very high level.

What I really try and do is just have ownership of the subject matter. I imagine if I was on their side, what the strongest possible argument I could construct is and go from there. The nice thing about the Supreme Court is that we almost always have the benefit of lots of other things that have been written on the subject: lower court opinions and lower court briefings. So I’m very rarely starting from scratch. But the ordinary analytical approach, and the ordinary approach in terms of advocacy, is to put your best foot forward, and then to respond to the other side. Don’t seem too defensive. I’ve always tended to have the structure of our argument, and then the structure of their argument and what I would say about it.

When you were in high school and college, you debated all the time. But you started to focus much more on your schoolwork when you went to law school. What changed?

After college, debate ends. If there had been debate in law school, I probably would have stayed in it. And I just loved law school. I really enjoyed the substance of all the classes, I liked working with the other students, the other activities, the law review and moot court… I was built for law school. It was what I was meant to do. So I just woke up and did law school, and eventually went to sleep, and did the same thing the next day and really enjoyed myself. That helped a lot; if I had been miserable, I’m sure I would have done poorly.

I just really, really, really liked it. I was learning new things all the time at a high level. I was not burnt out from school, because I hadn’t paid attention in high school and college. [laughs] I had plenty of academic interest left in me. So I don’t remember a minute I didn’t love of law school.

How did you snag your internship with Nina Totenberg as a law student? 

That was another illustration of the principle of calling the computer store. I just called her one day. I was in my first year in law school, I was having a hard time finding a paying law firm job for the summer – which is what people try to do in general – and I was interested in the Supreme Court a little bit. I thought I might write a paper about it. And so I remembered distinctly thinking, “Well, why don’t I work for somebody for free and see who needs the help.” I thought of NPR, because I always think of NPR as having no money. And I just called her one day.

Did she also pay you with Chick-fil-A sandwiches?

I did not even get a Chick-fil-A sandwich. I occasionally would get a biscotti, but it was highly irregular; it was not a meal I could count on.

What were some of your responsibilities during the internship?

I did intern-y things for her; I opened the mail. But I was her intern for two summers, and I did some more substantive work by the end. At that point she had the confidence to let me do some interviewing. And I did these statistics for her on the Supreme Court term in terms of voting patterns and the like. That ended up being very valuable, because I kept doing that after the internship and did it with the press a lot. It’s how I first got exposed to the Supreme Court press corps. I was very lucky, because in the two years that I was her intern we had two Supreme Court confirmations: the Ginsburg and Breyer confirmations. And that was great exposure for me.

How did you collect data on the justices’ voting patterns? 

Yeah, it’s pretty funny. Anyone who actually knows anything about statistics would laugh because this was using a calculator. This was just coming along and putting in two justices voting with each other. I think it was the most basic Excel spreadsheet you could imagine. But for lawyers and for reporters covering the Supreme Court, it was mainframe-level calculus, [laughs] when in fact it was super, super simplistic.

I’ve always been a real modest believer in the value of the statistics. Because they can tell you things about an aggregate, but in any given Supreme Court case, if you really want to do a good job at understanding it, you’ve gotta study the case way beyond the numbers. I collected the data at the end of the term so reporters could get a generalized sense of how the conservatives had done, how the more liberal justices had done, what the alignments were — because it’s hard for the general public to understand the term as a whole. It was a pedagogical tool.

Tell me about how you obtained a clerkship after law school.

Nina got me a clerkship with a district judge, who ended up being someone that I really didn’t like and who smoked like a chimney… So I left that job, and Nina got me a job with Judge Wald. She had an empty slot for about six months. Then I worked for another judge who needed a clerk for a couple of months. Weirdly, although I think of myself as having been a Wald clerk because I was there for six months, I actually had three clerkships in one year.

How did your writing improve over the course of those clerkships?

I remember very distinctively how I drafted my first draft opinion for Judge Wald. She came in, she handed it to me, and it was literally covered in red. Entirely covered in red editing marks. Then she said, “Do you want to talk about this tomorrow?” I definitely learned a lot about writing from the judges. The big problem in my writing then was that it would be too telegraphic, in that I assumed too much knowledge by people. She was a very good explainer.

Who are your favorite writers that have nothing to do with the law?

 I don’t know if I have a favorite writer who has nothing to do with the law, because most of the reading that I do, regrettably, relates to the law. I do read voraciously when it comes to current events. I just don’t read novel-style work, that sort of thing, or poetry. The reading that I do is not very stylistic. It’s much more factual. I overwhelmingly read the daily press; I might read 100 articles in a day to understand what’s going on in the world. So I don’t tend to think in terms of style. And I should say, I don’t really read editorial pieces. I’m much more interested in factual pieces.

Okay – then who are your favorite legal writers?

I think the best writers on the Court are the Chief and Justice Kagan, probably. They have a wonderful balance between being direct and accessible for readers who aren’t experts in the field, and also fun to read. I increasingly try to write like that, so if you read the motion to substitute that I filed in the Supreme Court recently on Acting Attorney General Whitaker, it’s at attempt to be both very substantive but also to occasionally turn a phrase. I want you to enjoy reading it.

“Schrödinger’s Attorneys General.”

Yes, stuff like that.

You said something interesting in a recent interview: that in most oral arguments, you try to find the one issue that you can persuade one justice on. How much of this approach is pre-planned, where you have an idea of which justice and which issue you’re going to pinpoint, and how much is feeling it out in real time?

It’s a lot of feeling out in real time, but definitely I have ideas going in. It’s one of those situations where you have to prepare as best you can, then stay flexible because you can be surprised. You can have these situations where you’re thinking, “Okay, this is a case where it’s the liberals against the conservatives,” and then you show up and Justice Ginsburg starts asking you hard questions. And you’ll be completely thrown off your game because you’re like, “Wait! You’re supposed to be on my side. What’s going on?” So it’s definitely both of those.

But it’s really a situation that people don’t take advantage of enough, I think, in arguing at the Court. That is, you’re having a conversation with them in which they’re telling you what matters to them. We as advocates too often get caught up in making our own points and not listening or trying to be responsive to the justices’ concerns. Advocates also forget where we are in the process by the time we get to oral argument – the justices have had these briefs for a long time and talked with their law clerks. It’s very unlikely that you’re going to completely change their mind about first principles. So my thinking about oral argument is much, much more modest than other people’s. It’s not like I’m giving up or anything; it’s that what I’m trying to accomplish is maybe more nuanced.

That reminds me of another thing you said in the interview – that even when Justice Breyer presents a looong hypothetical, he’s in fact helping you by explaining how he views your case.

Yeah, some of them will do that. Justice Kennedy would do that some. Justice Breyer will do that a lot. And that’s when they do it explicitly. Other times, you can basically infer where they’re at even when they’re not saying it outright.

It is hard to keep up with Justice Breyer’s hypotheticals because they can have so many different parts. Maybe I’m just not good enough at keeping all those balls in the air at the same time. But if a justice of the Supreme Court says, “I’m going to do X unless you convince me otherwise,” it’s only helpful. Then it’s all on the table.

When did you realize that your modest approach was more useful than trying to convince all nine justices of every point? How long did it take you?

Too long. [laughs] It was definitely a ways in. I’ve now done forty-two – it probably took me ten or fifteen arguments over the course of six or seven years to get to this point.

Do you prefer arguing first or second, and why?

Definitely second. It’s better to argue first in the sense of being the petitioner, because the petitioner usually wins. But being second is so much better because you get to listen to the questions in the first half and see what justices are concerned about what. It’s much easier to influence the process as the respondent, but it’s much harder to win.

When I argue second, I’m not paying attention to what the lawyer on the other side says much at all. This also is something different about me, because the natural tendency is to listen to what they say and then think about how they’re lying and how you’re going to respond to it. My mental energy is going into, “Why did the justice ask that question?” I might take a note, but I’ll never look at it later. It’s just that the process of writing notes is useful for me in terms of focusing the mind. And in general I will keep track of who’s asking questions that are favorable or hostile to what side. And I’ll note the subject matter of the questions, so that I can have a tool to see if a justice comes back to something multiple times.

But it really is a process of not letting your brain get cluttered. It’s very possible to try to stand up and say twenty things, but you have to remember that you’re actually trying to say three things. You don’t have enough control to get far beyond that.

How are you able to prevent clutter in the days and hours leading up to the argument?

Most people will cut themselves off at some point — like 24 hours beforehand. I do not. I work up until the argument; it’s just my style. If we’re the second argument, I’ll work through the first argument. There’s always more that I can do in terms of making things clearer in my own mind. The one thing I will do, if it’s a big and complicated enough case, is one or two nights beforehand I’ll literally separate myself from everything else that’s going on. I’ll stay in a hotel. The family will come visit, but I’ll try and remove distractions.

If you were a Supreme Court justice, what kind of oral argument questioner would you be?

Probably a lot like Kagan, who is asking questions technically. She’s trying to figure out how it is that she can assemble a Court or persuade one justice. And I might be a little bit like Justice Kennedy sometimes, in the sense that he was frequently interested in how he could write the opinion that addresses a particular issue. Because that’s a lot of what oral argument is: the justices have made up their minds about who should win, but it’s how they’re going to write the opinion. I think those are probably the two things I would do. 

In a way you’ve already been in this position, since you’ve served as a moot court judge.

Yes, all the time. We do that a lot — the members of the bar try to help each other out. Every time someone asks, I try and do it for them. I definitely do a lot more moots than I actually do oral arguments.

Increasingly, I’m trying not to do oral arguments. Every argument I get asked to do, I see if I can give it to someone more junior in the firm just to get them the experience. When you’re at the point where you’ve done as many as I have, you’ve gotten your chances to do it. You have a measure of responsibility to the other people who work with you.

Along with other people at your law firm, you recently challenged the constitutionality of Attorney General Matt Whitaker’s appointment. Your motion was submitted to the Supreme Court, but on the front page you also mentioned a cert petition to the Ninth Circuit. What does this mean, exactly?

What’s happened is that there’s a cert petition that’s pending at the Supreme Court. And I filed a motion that really doesn’t have anything to do with the cert petition. It’s that one of the named defendants is Jeff Sessions, and then when a government official resigns, their successor gets automatically substituted in. So what I have said to the Supreme Court is, you have to decide who the person after Sessions is. The Department of Justice has designated Matt Whitaker as the successor, and I said that’s wrong. The underlying case – the cert petition to the Ninth Circuit – is a guns case involving when you can bring a Second Amendment challenge. But the motion to substitute doesn’t have anything to do with it. And the motion is very honest, because no special issue about Sessions arises in this case. It is just that Sessions is named here and in lots of other cases.

How often does the Supreme Court grant this kind of motion?

I’m not familiar with the Supreme Court ever having been presented with this kind of motion. There’s never been a contested substitution of a government official. We can’t even find one in the lower courts, either. Generally speaking, there is a designated successor. Somebody either becomes the successor automatically or is named. We haven’t been able to find other fights about whether somebody was lawfully named the successor. In general, I think maybe what’s happened is that people tend not to fight the issue in the context of a successor motion. Obviously there have been fights over whether somebody was validly appointed. Using the successor provision as the way to have the fight I think is pretty novel.

Nobody really knows what’ll happen. The Supreme Court doesn’t like to do new and different things. It’s built on precedent in a thousand different ways, including how it operates. So I think that their ordinary reaction will be, “We don’t do this sort of thing.” But then it’s a question of, “Is this not an ordinary circumstance, so that they should?” I think the burden will be on us to prove it.

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, legal writing expert Ross Guberman, Georgetown professor Shon Hopwood, NPR reporter Carrie Johnson, Fix the Court Director Gabe Roth, IU Maurer Law Professor Ian Samuel, and Lawfare editor-in-chief Benjamin Wittes. 

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