Understanding the Appeal: Supreme Litigation from First Draft to Oral Argument

Kyle McEntee:

We're joined today by Rachel Frank, a senior associate at the elite litigation firm, Quinn Emanuel. In her practice, she has a special focus on appellate and Supreme Court matters. All right, Rachel, so I talk with a lot of prelaw students about their legal career interests and I see a lot of patterns.

One of the somewhat common areas of interest is in high-stakes Constitutional work. People see themselves arguing in front of judges or even the Supreme Court, expanding or protecting the rights of people they have seen left behind or trampled. But in practice, Con law tends to be a bit more about drawing boundaries than breaking new ground. And we'll get into that. But first, kind of to kick things off, can you explain what appellate litigation is?

Rachel Frank:

Appeals are what happens sort of after the first round of litigation, right? So trials happen in the trial court, which we call the the district court in our federal system. And then after that, you move on to appeals.

And there are two levels of appeals in the federal system. There's our courts of appeals, which are generally, you know, defined by geography. And then there's the Supreme Court, right, which sits at the top. And so appellate law is focusing on both of those, that second and third level of appeal. And then, of course, there's also the state system where we also regularly have appeals.

Kyle McEntee:

As a summer associate, while you were still in law school, you ended up working on a few cases that really served as a practical introduction for you to the world of appellate practice. One of those cases was Americans for Prosperity Foundation v. Bonta. I want to get more into what you learned working on that case, but first, can you set us up just the basic story and what was at stake?

Rachel Frank:

California used to require that nonprofits disclose their major donors to the state Attorney General. And enforcement really ramped up in about 2010 with thousands of deficiency letters that were sent to charitable organizations across the state. And the state claimed that it had a need for that information to police charitable fraud. But balancing that government oversight need was also donors' wish for privacy and anonymity. And you know, there could be a chilling effect, just like with political participation on charitable giving, if there are concerns about harassment or retaliation.

My firm, Quinn Emanuel, long before I was an associate, in fact, I think I was still in high school when they initiated the case, they brought a lawsuit seeking a preliminary injunction to halt enforcement of the law. And that preliminary injunction then went up to the Ninth Circuit, which is that intermediary court. And then it went back down to the district court, and then there was a trial, and then it went back up to the Ninth Circuit, which is where the case was when I was a summer associate.

Kyle McEntee:

Can you explain what a preliminary injunction is and how that actually worked in this case? What were they requesting for relief?

Rachel Frank:

So a preliminary injunction is an order to do something, often an order to not do something. So the phrase temporary restraining order, you may have heard on shows like Law & Order, a preliminary injunction is similar to that. And a TRO is actually a type of preliminary injunction. So here we were suing to stop enforcement by the Attorney General.

Kyle McEntee:

So you're representing the petitioner eventually, once it goes through the trial, meaning that your client lost for the original request, right? So you're representing Americans for Prosperity, they're a 501(c)(4), (c)(4)s tend to spend money on issues ads during elections, they don't want to disclose their donors. So basically California wanted people to know about it, your client really didn't, but really they were after strengthening donor privacy protections. So you mentioned that the case started while you were in high school. Where were you brought in?

Rachel Frank:

So when I was a summer associate, the case was being argued for the second time before the Ninth Circuit. I was somewhat involved, though not honestly heavily involved at that point in preparing one of the partners for the oral argument in that case. And then when I came back to the firm as a first-year associate, that was in the middle of the cert petition briefing process. So at that point, we had lost at the Ninth Circuit, and then we're asking the Supreme Court to take the case.

Kyle McEntee:

And that's what the cert petition is, it's the request to take the case.

Rachel Frank:

Exactly. Exactly. The Supreme Court gets thousands of cert petitions every year and only takes a small handful of cases. So it's very hard to convince the Court that your case warrants their time.

Kyle McEntee:

Is this kind of where you saw your career going when you started law school? I know you were thinking pretty intentionally about your path to law, but was this really at the core of your intentions?

Rachel Frank:

It was absolutely what I wanted to do. I started law school actually wanting to focus on Constitutional law. I wrote one of my undergraduate theses on Constitutional law. I had taken some Constitutional law courses in undergrad. And then when I was in law school, I took as many Con law classes as I could. It was always what I really loved. It still is.

My dog is named Marbury after Marbury vs. Madison. So I truly do love this area of law, but I did not have the expectation that I would get to be able to work in this area that is truly at the heart of my interests with the comfort and the educational experience of a big law firm.

Kyle McEntee:

Yeah, I mentioned at the top of the episode that this is something a lot of people want to do and they see themselves doing. And I think part of that is because this type of practice is pretty well represented in pop culture and the news, even if it's not always represented well. And like entire news cycles are driven by the results of these sorts of cases. So I think it's really interesting to see how someone who is still in law school and a first-year associate can play that role. How has your work evolved since then?

Rachel Frank:

It's certainly changed. When I was initially helping to prepare partners for Supreme Court arguments as a first-year associate, a fair amount of my work was putting together binders. But it was also substantive. You know, we, in preparing for an oral argument, a lot of the arguing attorneys like to have cheat sheets in front of them.

So if the justice asks about a particular factual question, they'll be able to say that is on, you know, page 689 of the joint appendix. So I was helping make substantive materials like that. But at the same time, you know, I've always felt like my views, my opinions on substantive issues have also mattered.

You know, I attended a number of moot courts in that first year, something I still do. And yes, I am there taking notes. But every time after the partner will turn to me and say, Rachel, what do you think? And I will get to say, I think you did a really great job with X, Y and Z. With ABC, maybe we try this other angle.

Kyle McEntee:

So these days you've moved past making those binders. You serve as counsel actually before the Supreme Court in recent years. One of your main roles in these kind of cases is helping prepare partners for oral arguments. And you do that at a moot court. Can you kind of explain how a moot court comes together?

Rachel Frank:

We will often do what we call an internal moot first. So that'll be with usually other partners or senior appellate associates at the firm. And that's going to be the sort of the first cut of things. And the partner who's arguing is going to stand up and they're going to do their introduction. And then they're going to field questions for usually about an hour. So even if the oral argument is only scheduled to go 15 minutes, we do the moots for much longer.

And the subsequent moots will have that same structure. But that internal moot is especially helpful to really sort of work out those early kinks. You can have often more candid conversations about the best ways to argue an issue, the best ways to present something when we are still working, you know, within the zone of attorney-client privilege and with your colleagues.

But then subsequent moots, we will sometimes do them, you know, universities like Georgetown and Harvard will host moots for Supreme Court arguments, in which they'll be open to the public, right? So there's no privilege there. But they'll be bringing in real experts who, you know, might be law professors with expertise on the subject, law firm partners. We also will often partner with groups, you know, nonprofit groups or think tanks that have expertise in an area; they will host a moot.

So we'll get different people with expertise in different areas. Oftentimes, if we're counting up votes on the Court and we think, oh, well, there's, you know, this person could be a swing vote, maybe we'll try to get somebody who clerked for that Justice to attend one of our moots and sort of channel them so that we can get the best preview as to what kinds of questions that Justice might ask.

Kyle McEntee:

So who's representing the other side in this? Is it an internal Quinn Emanuel lawyer or is that where you're getting another firm involved? I mean, certainly you're not mooting with the actual other side.

Rachel Frank:

That's right. So we don't do moots with the other side. And, you know, an oral argument is presented in, you know, there might be 15 minutes for one side, 20 minutes for the other, and then five minutes of rebuttal for whoever went first. So it's going to add up to the same amount of time. But there isn't the same back and forth that you often will get in a hearing in a District Court or something like that. And so I think it is a little bit less important to have, you know, there's someone who's directly standing in for the other side during a moot, but yes, there is a real strategic question about how you handle a rebuttal. And those are often issues where, you know, if there was something that, a point you wanted to get to in the first year opening, but you didn't get to, you could bring it back up in rebuttal, but it's not a full back and forth.

Kyle McEntee:

So we've been talking about the different members of the larger litigation team. How big is the team that's typically working on one of these cases?

Rachel Frank:

It can vary. So I would say your sort of typical run-of-the-mill Court of Appeals team, it's probably smaller than a lot of people would expect. I would say one partner, one senior or mid-level associate, one junior associate could handle, you know, a sort of typical Court of Appeals case. You know, for our big Supreme Court cases, the teams are generally, you know, a bit bigger. You're going to have maybe three juniors, two or three mid-level senior associates, and a couple of partners.

Kyle McEntee:

But still we're talking much smaller than maybe one of those giant transactional teams.

Rachel Frank:

Oh, absolutely. Much smaller. And that means that, you know, each individual person handles more and touches more aspects of the case. So, you know, you mentioned I might be behind binders, but, you know, I still am, you know, responsible for making sure that the binders that the judges are preparing are what we need. And, you know, I could talk your ear off about fonts at the Supreme Court, about the intricacies of filing systems. And those are things that I still deal with on a regular basis. And the fact that I know those little details means that I am still a resource.

Kyle McEntee:

You mentioned that you actually sat at the counsel table at the Supreme Court. For those who haven't seen the inside of that room, what did it feel like to be there?

Rachel Frank:

It's an incredible experience. I would encourage anyone to go watch an argument. It can be hard to get in. The lines are long, but they are open to the public. You get there, and if you are part of, you know, the team that is arguing that day, you get to go into the lawyer's lounge, which is, I think, a part of the Supreme Court that not a lot of people get to see. And it's very collegial in there. You know, the Supreme Court bar is a small group of people who know each other quite well, people who maybe used to work at the same firm or they both worked in the Solicitor General's office together. And then you go into the courtroom, you know, it's their hallowed halls, right? And it feels that way. There's chatter. But then, you know, when the gavel comes down, everyone is extremely quiet. It's a very serious environment. But it's a very, very different experience to get to see the Justices in front of you. You can see them, you know, how they relate to each other. And often their questions might be directed at an advocate, but they're actually looking at one of the other Justices.

And so you can pick up on things like that when you're in the courtroom that you can't pick up on in a recording.

Kyle McEntee:

Now, I know that's not all your cases. But how many cases are you typically handling on your plate like at once?

Rachel Frank:

That really varies. I have had very busy periods where, in a given month I might bill on 20 matters. That is not typical, more typical for me would be somewhere between six and 10.

And some of those will be appeals or cases in the courts of appeals. But I also do a fair amount of what we call issues work, which is similar in that it's focused on legal questions, but can happen in different courts. So I was recently embedded in a federal criminal trial team. And I was doing things like writing our motion to sever, our motion to dismiss, writing, you know, various other motions that turn on generally on legal issues as opposed to factual issues. And so that type of work can be similar to appellate work. It draws on the same skills, but can happen in different contexts.

Kyle McEntee:

We've talked a lot about the oral advocacy side, but there's also a great deal of writing that goes into appellate work and specifically writing appellate briefs. So that's the document that you're submitting to the court arguing why the lower court's decision was either correct or incorrect. These briefs have a reputation for being highly crafted pieces of writing. How do you think about writing something persuasive like this?

Rachel Frank:

Yes, it could depend a little bit. I mean, usually with an appeal, it's always a good place to start and see what was argued before. Oftentimes, I will have conversations with partners before I start writing about what our approach is going to be. But not always. It depends. You know, people are very busy. And especially if it's a case that I've been involved in for a while, often I will just take the pen. I always start with an outline. And even if it's just an outline that looks like a table of contents, that scaffolding is extremely important to the brief flowing in a logical way. And it's also very helpful for me to organize my thoughts about what arguments are sub-arguments of others, what are separate, what we want to prioritize, what we might want to de-emphasize, particularly, you know, if we've lost below. Depends really on the situation. Sometimes also, you know, if there's a procedural issue, like if there's a standing question about whether we should even be in court at all, usually we address those first because there's a preliminary question. So we always try to think through that and then start fleshing it out, you know, with that legal research and with the argumentation.

Kyle McEntee:

Was that always your approach to writing?

Rachel Frank:

I think I learned pretty early that it had to be because if you just start writing and then you try to organize, it can get very messy very fast. And we have been increasingly using, you know, AI as a tool. And I think that is something that AI I find often doesn't understand very well. You ask it, write me a brief, and it'll just sort of throw everything in there in an order that does not make a ton of sense. So sometimes, you know, if I am using AI to sort of help me think through an issue or think about an outline for a brief, I always start with that initial phase. Usually I will give it the outline because I've just found it's not terribly good at that sort of structuring. It doesn't know those rules about, oh, you know, standing comes first or, you know, prioritize things and, you know, in this order.

Kyle McEntee:

What's interesting about AI is that it like takes stuff that's happened in the past and then tries to draw conclusions or order things. But you're dealing with something that's not necessarily public record. So are you ingesting private documents into the AI to help you through this process?

Rachel Frank:

Only if we have an enterprise license. And I know that those documents are not going to be something that the AI learns from. I would never upload, you know, something confidential to a platform like that.

Kyle McEntee:

So how have you learned how to make the most out of AI in your practice? Because it sounds like you're using it a fair amount.

Rachel Frank:

Yeah, I think Quinn Emanuel has actually been pretty far ahead of the game and embracing AI within limits, of course, right? We have great resources at the firm. We've got folks who specialize in that who, you know, for a certain case might become embedded and help us set up a project that then has sort of the building blocks built into it. And so I can just, you know, pop in and ask some questions. And it's already been given the knowledge in a way that it understands, the background information in a way that it understands. And then I can use it.

But really, I would say the way that I have learned to use it mostly is just trial and error. I see what works. I see what doesn't. There's something about it that can be a bit illusory, too. It'll give you an answer that on first blush will sound great. But then if you think about it for a little bit longer, you realize, oh, that actually doesn't make that much sense. Or you look up a case and it doesn't actually say that. So I think there can be this real temptation to use it and, you know, you'll get these results that on the surface look like exactly what you're looking for. But you have to have, as you say, that background information, that background knowledge to know what the substance of it should say in order to pick out what is real and what isn't.

Kyle McEntee:

So it's like your thinking partner, I guess?

Rachel Frank:

Yeah, I think you could say that, you know, you don't always have a colleague that's down the hall and can at the drop of a pen just, you know, sit down and think about something with you for a minute. It can also be very helpful for combing through a record. You know, you have a transcript from a two-week trial and you think that something was probably talked about once or twice, but you don't know where. It's pretty good at reading through things and digesting it. Again, it can be wrong. It absolutely must be checked, but I would say it is still on balance when used responsibly very beneficial to have.

Kyle McEntee:

Is it helping you work less or do you still have to work extremely long hours?

Rachel Frank:

I don't think that my hours have changed, but I think it is in a lot of ways helping you work more efficiently. For me, it does help the thinking process and I think it does help me move a bit faster through things.

Kyle McEntee:

Have you used it to pretend to be a Justice yet? Because I remember like when Chat GPT first came out, one of my favorite things to do was be like, argue this as if you were Justice Scalia and it would give the argument using his phraseology, et cetera. And then you change it to say, okay, now make the same argument in Justice Kagan's voice and it would go do it. Are you able to use it that way or is it not trustworthy enough to kind of get into the heads of the people that you're trying to persuade on the bench?

Rachel Frank:

Yeah, actually one of my first introductions to using it was Claude was when we were preparing for a Supreme Court oral argument. And we took the transcript of one of those moots that we were talking about and we uploaded it and asked Claude to generate more questions in the voices of specific Justices. And it did a phenomenal job. And for a moot like that, there's less risk of anything going wrong. If it gets the tone slightly off for Justice Thomas, it's not going to be the end of the world, right? You're just using it to sort of generate questions. And again, as that sort of thinking partner to brainstorm, there's less risk of downside there.

Kyle McEntee:

All right. So you've been at Quinn Emanuel your entire career almost because you took a break to clerk. What was the motivation to, after your first year, decide to take an appellate clerkship?

Rachel Frank:

Yeah. So I actually, I mean, I signed up for the clerkship back when I was in law school. You know, the clerkship application process, it's a bit different now than it used to be, but it is still, you know, people are applying for and interviewing for clerkships years, many years in advance of when they actually get them. I think it is often typical to have your clerkship right after law school before you would go to a firm. But because judges are hiring so far out in the future, oftentimes students will end up in situations like me where they have a gap year in between. And sometimes people go out and do different things. You might go work at a non-profit for a area of law, doing something different.

I personally had had a great summer at Quinn Emanuel and was happy and eager to come back to the firm for that year in between. But I felt like it was very valuable to have work experience, particularly work experience with the people and the kinds of work that I was going to be ultimately doing, because it meant that while I was clerking, I could very easily see how what I was learning was going to be applicable when I came back.

Kyle McEntee:

Any good examples?

Rachel Frank:

Yeah. I mean, I think the judge that I clerked for was an incredible, or is an incredible writer. And we went through many, many drafts of opinions. And I learned so much about just good quality legal writing from her. But I also learned about a different kind of writing that I didn't expect to learn about, which is just letter writing. You know, the judges, at least on the court that I've clerked on, send a lot of letters back and forth to each other. The Fourth Circuit is famously collegial. And learning to write letters that sort of explain why, you know, you actually might be dissenting from an opinion that someone else has written, or you are, you know, navigating a sort of a tricky issue that there might be some conflict about. And writing letters that keep the tone collegial but are direct, that was a skill that I didn't expect to learn while clerking, but it's certainly been very valuable.

Kyle McEntee:

And I think the firm and big firms in general see the value in these because they often offer these large clerkship bonuses. Were you able to still get a clerkship bonus, even though you had already started at the firm and you took a year between working at the firm? Did they still give you that clerkship bonus when you came back?

Rachel Frank:

Yeah, absolutely. I think the firm places an incredibly high value on clerks. And I think actually our bonus is higher than at other firms, which reflects the value that Quinn places on clerks. And the fact that I had been at the firm before did not change that.

Kyle McEntee:

The fact that Quinn Emanuel is this litigation powerhouse, I mean, was the firm in particular on your radar going into law school? Or is it you kind of learned in law school, who was doing the work you wanted to do, and then you just figured out how to get there?

Rachel Frank:

There were no firms that were particularly on my radar before I went to law school. I did not grow up in a family of lawyers. Covington and Burling and Latham and Watkins were not household names. I was aware of who Kathleen Sullivan was, and I had actually done a little bit of work for her on a First Amendment issue related to a project I was involved in law school. So I knew the firm through her. But no, when I was applying to OCI, OCI is our on-campus interviewing. It's how students get connected with law firms. I cast a pretty broad net, and I actually struggled to find a firm that I felt like I was connecting with. Through that process, I had a lot of interviews with great firms where I didn't particularly feel like I was clicking, and I didn't know why. I then cast a bit of a broader net. I did some online research on my own. At the time, Quinn was actually focused almost exclusively on hiring clerks, and so they weren't doing on-campus interviews.

But I just sent off my resume to their recruiter and was brought down here for an interview. When I started talking to people, I did. I had that click feeling almost instantly when I was talking to people about what I was working on in law school, what cases they were handling. The conversations just flowed easily and I felt very quickly like this was a place that I could really do interesting work with people that I enjoyed working with.

Kyle McEntee:

So with some time passing between then and now, are you able to better articulate what was lacking at those other firms for you?

Rachel Frank:

I'm not sure. I mean, I don't want to say anything negative about any other firm, but I will say that at Quinn, what matters is the work. And there are a lot of other things that we consider to be part of big law. I don't know if you've seen Suits or these other shows that have characterized big law. And it's a lot of walking around in a suit and being important. And at Quinn, there is no dress code. There is no in-office requirement. You don't have to be at your desk from 8 a.m. to 6 p.m. or something like that, right? You need to be available for calls. And we were talking, you know, we have to be available, quickly responsive for emails. But what ultimately matters is the work. And that was what I was really interested in. And, you know, these other things, I think Quinn has deprioritized because what matters is the work and giving our clients the best legal representation that we can.

Kyle McEntee:

I think that's just interesting to observe as a contrast to other firms.

Rachel Frank:

Yeah, I think Quinn does stand out in that way. And to me, it makes a big difference in terms of, you know, work-life balance, too. There's no hiding that there's always a lot of work to be done, especially when you're trying to do everything, you know, at the highest level possible. But when you do strip away some of these things, like having to be in a suit, having to be in the office, et cetera, that actually leaves more time for things in your personal life, right? If you want to spend some time, you know, working from your parents' house around the holidays instead of being in the office. Or if you, you know, have some hobbies that you require that you, I don't know, if you're training for a marathon and it requires long runs, something like that. But yeah, if you're sort of stripping away some of those extras can really leave more time for the things that, you know, we do outside of law. And that's important.

Kyle McEntee:

Have you struggled with that work-life balance?

Rachel Frank:

I think it's gotten easier as I have become more senior, more used to my role, more used to working with specific people, sort of understanding people's expectations. There's no hiding that as a first-year associate, adapting to firm life is tough, right? It's all the, our cases are high stakes. They matter a lot to our clients and small mistakes can have a big impact and that can be very stressful. But I think something that you learn over time is that everyone makes mistakes and you need to show up every day and do your best. And if something goes wrong, you do what you can to fix it. And then you move forward and you move on to doing the next thing the best that you can. And making time for yourself is important. Burnout is absolutely real. And I like to go to yoga. And for me, that does involve turning my phone off. So I'm cognizant about, I'm not going to do that on a filing day, right? You choose your moments and you manage. But I would say, you know, I've seen associates struggle where they just put off all things personal, all things for them and just do the work. And that can't last. So you need to figure out how you're going to manage things in a way that works for you and that works for your teams.