Practicing Before th ...

Practicing Before the U.S. Supreme Court | Kannon Shanmugam

October 13, 2022 | by D. Todd Smith

For many attorneys, the prospect of a U.S. Supreme Court argument serves as the capstone of a legal career. But for a select few, like Kannon Shanmugam, chair of Paul Weiss’s Supreme Court and Appellate Practice Group, arguing before the Supreme Court is a regular occurrence.  Kannon joins Jody Sanders and Todd Smith to discuss his path to Supreme Court advocacy and some of the unique challenges it offers. Kannon also discusses the stiff competition for Supreme Court-bound cases and breaks down advocacy tips for attorneys at every level of the court system. Join us to learn more about practicing before the nation’s highest court.

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Practicing Before the U.S. Supreme Court | Kannon Shanmugam

Our guest is Kannon Shanmugam, who is a partner at Paul Weiss in Washington, DC. Thanks so much for joining us.

Thank you, Jody and Todd. It’s great to be with you.

We should point out that we are having this interview from the Advanced Appellate Seminar here in Austin at the lovely Four Seasons. We decided we couldn’t miss this opportunity to visit with Kannon. We went forward to bringing some more programming like this to you flowing from this seminar.

It’s great to be here at the State Bar of Texas meeting.

Thank you for accommodating us. We appreciate it.

It’s my pleasure.

A lot of our readers probably know who you are already but if you would maybe give us a little bit of background, tell us about yourself and how you got to where you are.

I grew up in Lawrence, Kansas. My father was a professor at the University of Kansas. That’s why when I tweet, I tend to tweet about the Jayhawks rather than about the law. I went back East, as folks would say in these parts, for college and law school. I was not somebody in college who was sure I wanted to be a lawyer. I grew up in the 1980s. In some sense, I always wanted to be Harry Hamlin’s character in LA Law. When I went to college, if you had asked me on the first day of freshman year, I probably would have told you that I was going to be a journalist rather than a lawyer.

I was a very serious college journalist. I was the Editor of the Harvard Independent, which was the weekly newspaper on campus. I spent two summers working for The Kansas City Star, my hometown newspaper. It was only toward the end of college that I had the epiphany that being a journalist was going to be a pretty tough career. That was even before the advent of the internet and the effects that it had on journalism. I started to think about law school. By the end of my time at Harvard, I was pretty sure I was going to go to law school.

I had a bit of a two-year detour. I went to England and did a Graduate degree, but at the end of that time, I came back to Harvard, where I went to law school. In some sense, I was an accidental appellate lawyer as well as a lawyer because when I was in law school, I was pretty sure I wanted to be a trial litigator. I spent my 2L summer at Cravath in New York, which now did not have an appellate practice. It was only after clerking first for Judge Luttig on the Fourth Circuit and then for Justice Scalia that I started to think about a career in Appellate Law.

We have had the privilege of having former US Supreme Court clerks on the show. We’re happy to add you to that number. Do you have a quick Scalia story you can tell us and one that you can share publicly?

There are so many stories about Justice Scalia. When I think back on the year I had with him, my abiding memory of him will be him hunched over his computer, working on one opinion or another. He had gotten back from a trip to Japan. He had this Japanese baseball cap that was about three sizes too small for his head. He would be sitting at his desk with this baseball cap hunched on the top of his head, typically smoking a cigarette because that was one of his vices and working away on a draft opinion.

He took writing so seriously. When I think back on that year, it’s very tempting to think about Justice Scalia and to think, “Here’s somebody for whom writing came naturally.” If he were still with us, he would be the first to say that was not the case. It was hard work. He labored over every sentence and every word much the same way the rest of us mere mortals do. When I think back on the year, my vision of the year is Justice Scalia working away on draft opinions. It was such an incredible privilege to have the opportunity to work with him and to learn from him.

Which term did you clerk at the court?

I clerked at the court in the 1999-2000 term. That was the same term as a number of luminaries, including Texas luminaries. That was the same term as Justice Brett Busby from the State Supreme Court and his incredibly impressive wife, Erin. They met during the clerkship year. They were the one couple that emerged from our year. There was also somebody by the name of Ketanji Jackson who clerked during that year and has also gone on to great things.

It was a wonderful group of people. As Erin told you when she came on your show, it was a very collegial year at the court. We had very deep friendships across chambers both during the year and thereafter. Vicky, my wife, and I hosted a reunion of the law clerks from our year for the twentieth anniversary of the clerkship. Virtually everyone came, which is a testament to how deep those bonds were.

Were any standout cases from the 1999-2000 term that sticks with you?

It was a blockbuster term. As Erin told you, it will forever be remembered as the term before Bush versus Gore, but it was a significant term like the completed Supreme Court term. We had cases across seemingly every major area of the law. We had the first of the two partial birth abortion cases that year. We had the Dickerson case on whether or not Congress had the power to overrule Miranda effectively.

We had a number of cases on criminal procedure because it was in the immediate aftermath of the enactment of AEDPA, the statute that reformed the habeas process. We had a case involving prayer at high school football games. It’s a case coming out of the Santa Fe school district here in Texas. In some sense, a lot of cases prefigured the cases last term because, in a lot of these areas of the law, those cases ended up being important precedents for things that the Supreme Court did in 2021.

Where did you head after your Supreme Court courtship?

I started my legal career at Kirkland & Ellis. At the time, the head of the appellate practice there was another Texan, Ken Starr, who had been Solicitor General of the United States. I went to Kirkland without a clear desire to be an appellate lawyer. I knew by the point that I had finished my clerkship that it was something I wanted to have as a significant part of my practice. I joined Kirkland in November of 2000, right after Ken came back from having been independent counsel.

Ken had worked with an incredible parade of lawyers. I’m not sure that there’s any appellate lawyer in America who has so many significant figures in his coaching tree. He had worked very closely with Paul Clement when Paul was an Associate at Kirkland in his first stint there. He worked with Brett Kavanaugh. Indeed, Justice Kavanaugh was one of the people who recruited me to Kirkland and then promptly left the firm on my second day there to go down to Tallahassee to work on what ended up becoming Bush versus Gore. I didn’t work all that closely with Justice Kavanaugh when I was at Kirkland.

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Supreme Court: It’s hard to beat that list of mentors.

Precisely because Ken had gone away for a while, a lot of the people in his core team had gone and done different things. Ken came back to the firm in the fall of 2000. I joined the firm. There were immediately tremendous opportunities to work with Ken on significant appellate matters. I look back on those years as the formative years both in my deciding to focus on appellate work and also in developing as an appellate lawyer.

It seems like even young lawyers coming out of Supreme Court clerkships, having that formative relationship with someone experienced or somebody who had been at the top level like Judge Starr, can impact that younger lawyer. Would you say that was the case with you where Judge Starr helped put you on that path?

When I think back on the wonderful mentors I’ve had at virtually every stage of my career, Ken would be right at the top of that list. Every year, there are 36 or so Supreme Court clerks who have newly minted any number of clerks for great Court of Appeals judges, state Supreme Court judges, and the like. The reality is that, particularly in the appellate area, only a very small number of those people are going to emerge. The key differentiator is having a wonderful mentor early in your career and getting tremendous opportunities where you get a lot of responsibility.

Ken is certainly somebody. Another of my future bosses, Ted Olson, is another who is adept at promoting the next generation. The opportunities I got during those four years at Kirkland set me on my way without question. In particular, I had the opportunity to be one of the principal brief writers on the briefs in McConnell versus FEC, which was the challenge to the constitutionality of McCain-Feingold at the Supreme Court level. For somebody who was 3 or 4 years off a clerkship as I then was, that was a career-defining opportunity.

That’s an incredible lineup of folks you had the privilege of working under and being mentored by. Some of the names are at the very upper echelon of appellate practice. I’m a little jealous.

I was lucky. At every stage, I was fortunate to come under the wing of these legendary names. You think about Judge Luttig, Justice Scalia, Ken, and then Ted, who was the person who hired me into the Solicitor General’s office. It’s hard to beat that list of mentors.

I did want to talk a little bit about your transition to the Solicitor General’s office and a little more about that office. You’re the first person we have had that has worked at the United States SG’s office.

It’s a special place. In particular, if you want to have a career, a substantial focus of which is practicing before the Supreme Court, it’s a pretty common stamp you see on people’s passports to have been in the Federal SG’s office. State SG’s offices are increasingly becoming similarly prominent. I was lucky to get that opportunity relatively early on in my career.

In part, I got the opportunity because of the McConnell case. You may remember that case involved a challenge being brought by Senator Mitch McConnell and others who were the plaintiffs. We were representing Senator McConnell and some of the other plaintiffs in the case, but it was being brought against the government. At the time, Ted Olson was the Solicitor General. To his credit, whatever his personal views, he very vigorously defended the constitutionality of McCain-Feingold before the Supreme Court.

In some sense, I came to Ted’s attention by virtue of my work on that case. I worked very closely with Paul Clement, who was then the Principal Deputy SG, coordinating the schedule and the litigation in that case. By virtue of that, I was hired the following year by Ted to go into the SG’s office at a relatively early point in my career. I was 31 years old when I was hired by Ted to go into that office. It was probably just as well because, as I’ve said in other forums, I was probably too young to be as scared as I should have been about the prospect of arguing cases before the United States Supreme Court.

For those who aren’t as familiar, explain how the SG’s office works, how they get their cases, how as a younger lawyer, you get assigned, and the types of things you do in that office.

The way the SG’s office gets its cases is that it has one client, but it’s an exceptionally litigious one, the United States of America. The SG’s office handles all of the government’s litigation in the Supreme Court. If the government is arguing a case in the Supreme Court either as a party to the case or as a friend of the court, or as an amicus curiae, it’s going to be a lawyer from the Solicitor General’s office almost invariably who does the oral argument and handles the briefing and so forth. Beyond that, the Solicitor General also plays an important role in coordinating the government’s overall litigation strategy.

That’s a very important part of the job. It’s the part of the duck that’s underwater because it’s by definition not as public, but the SG decides whether or not the government can take appeals to the lower appellate court. If a lawyer in the United States attorney’s office here in Austin wants to take an appeal to the Fifth Circuit, they have to get approval from the SG in Washington. That’s a significant part of the job both for the SG himself or herself and also for the line attorneys in the office.

One of the things people don’t realize is it’s an awfully small office. When we think about the government, we often think about fairly bloated components of government. The SG’s office is certainly not one of them. It’s an office of around 22 lawyers. Most of those lawyers are career civil servants, so they don’t change from administration to administration. When you think about the fact that they’re handling all of the government’s litigation at the Supreme Court and supervising all of the government’s litigation nationwide, that’s a pretty small team of people to take on some pretty significant tasks.

You talk about having the United States and trying to coordinate all the appellate litigation nationwide. I can only imagine the potential inconsistent positions that may come up. You’re dealing with monitoring circuit splits and wanting to carefully select the cases that wind up going up to the US Supreme Court. That’s a lot of wrangling to have to do for such a small office.

I certainly learned a lot about oral advocacy and brief writing when I was in the SG’s office. I was lucky to work with some real legends of the Supreme Court bar when I was there and people like Michael Dreeben and Ed Kneedler, and to work under great Solicitor Generals like Ted, Paul, and Greg Garre. Ultimately, one of the big takeaways from my time in the office was learning how to think about appellate strategy.

One of the reasons why being in the SG’s office is so interesting from that perspective is that, unlike in private practice, there’s no client that you can pick up the phone and call. The client is the United States of America. In theory, you could pick up the phone and call the White House, but that’s not something that SGs tend to do all that often. Even then, it’s not always entirely clear which component of the government is the client.

You’re making those judgments yourself. Ultimately, it’s the SG who makes the final judgment. If you’re a line attorney in the position of an assistant to the Solicitor General, you’re doing your best to make those judgments about what’s in the government’s best interests, which cases are the best cases to take up to the Supreme Court, which cases might not be good vehicles, and which to litigate issues of institutional importance.

I’ve taken a lot of lessons from that into my time in private practice. When you’re representing big companies, in particular, they often are dealing with fairly similar issues. A lot of my clients are dealing with litigation nationwide. There are strategic questions about which cases to advance in litigation and where to pursue those cases. Those judgments are not dissimilar.

Let’s talk about your move back into private practice. Did you go from the Solicitor General straight to Paul Weiss? What did you do after that?

I had one other stop on my resume. I was a partner at Williams & Connolly for a little over ten years. I had a wonderful experience there. In some sense, that was my first experience both as a law firm partner and as a head of an appellate litigation practice. Much is the case now with Paul Weiss. At the time at Williams & Connolly, the firm had not historically had a discreet Supreme Court and appellate litigation practice.

I was charged again at a relatively early stage of my career with building that practice. It was a great experience. I probably made a lot of mistakes as I was building the practice. No one in law school gives you a manual for how to build a law practice. I was very proud of the practice I built at Williams & Connolly. I had a wonderful experience at the firm.

We have a very well-established appellate bar here in Texas. There are other places that do. Appellate work is different, as you’ve hinted at. What is the thinking behind, at least at that time, firms like Cravath and Williams & Connolly not having already dedicated those resources to that practice area?

person sitting in chair looking at document
Supreme Court: If you want a career, a substantial focus is practicing before the Supreme Court.

One thing that has always been of interest to me as an outsider is how well-established appellate practice is as a specialty in Texas. It’s interesting because if you think about it in terms of Washington, you might think that if there’s anywhere or there is an established appellate bar, it would be in DC, but the reality is that a specialized appellate bar is a relatively recent development.

When Ken joined Kirkland & Ellis in 1993, he was one of the first to try to build that practice in private practice in Washington. Until then, you could list a number of great litigation firms that, for one reason or another, hadn’t done it. One of the great ironies is that I had always looked at Paul Weiss from the outside and thought, “Here is one of the nation’s leading litigation firms. Why doesn’t it have that practice?”

One of the things that I learned when I started talking to Paul Weiss was that it was something that the firm had long wanted to do, but the reality is that there is a relatively small number of people who have established national reputations in appellate practice. Unless you can get one of those people, it’s a very difficult thing to try to develop organically. Precisely the reason why Paul Weiss wanted me to join the firm was that by that point, I had a bit of an established reputation. The firm thought this was a way of establishing that practice.

On the topic of narrow advocacy and Supreme Court advocacy, it is different than your typical appellate advocacy. How does Supreme Court advocacy differ? How is it that there’s a different skillset to that?

Supreme Court advocacy is different in a couple of respects. One of them is that there’s a tremendous temptation to think that Supreme Court arguments are a lot like other appellate arguments, but the Supreme Court is not bound by precedent. It is setting the rules for the entire country. In terms of the types of arguments that you make to that court, they are typically much more arguments about first principles and much fewer arguments about precedent. Precedents are always important.

While stare decisis is not an exorable command, it is still significant to the court. You want to be framing your arguments in terms of what the Supreme Court has previously said. Ultimately, you want to convince the Supreme Court that you’re right as a matter of first principles, whether that is a matter of first principles of the constitution or as a matter of statutory interpretation. That’s different from an argument in a Court of Appeals.

The other thing that’s different is that the Supreme Court is hearing only 60 cases a year. It has the luxury to dive much more deeply into the cases than a typical Court of Appeals does. I have an argument in the Second Circuit in New York. That will be 1 of 3 cases that are argued. The panel may very well be hearing 10 or 15 cases that week alone. The Supreme Court hears ten cases in a good month nowadays. The court does have the luxury of diving more deeply. That means that as an advocate, you have to be prepared to get much more deeply down into the weeds than in other courts.

There’s the oral advocacy part of it too. What bigger stage is there as far as an appellate lawyer than standing at the lectern at the Supreme Court building in Washington? That has to be an amazing experience.

There’s no doubt. It feels like you’re in the Major Leagues. It feels like you’re at Yankee Stadium. Since I’m a college basketball fan, it feels like you’re in Allen Fieldhouse when you’re arguing in the Supreme Court. It’s hard not to feel a sense of awe at the occasion. In some sense, whenever you argue a case in the Supreme Court, there’s something very special about that. Even as somebody who has done it a fair number of times, I still feel that sense of awe whenever I walk into that building.

With that having been said, for any self-styled Supreme Court litigator, the reality is that we all spend the majority of our time arguing cases in the Courts of Appeals and the state appellate courts. Frankly, one of the things I enjoy about my job is having the opportunity to travel around the country, argue in all of the circuits as I’ve had the chance, and argue in front of new judges because one of the differences with the Supreme Court is that you know who you’re getting when you have a case in the Supreme Court, whereas in the Courts of Appeals, you typically don’t know until a few days beforehand who your judges are going to be. That’s a major difference in terms of the way you approach the task of oral argument.

With only 60 cases a year that get argued and relatively few in terms of what gets filed, how do you find the cases? Do the cases find you for cases that you think you’re going to take to the Supreme Court?

There’s no one formula for that. I’ve been very fortunate in that cases have largely found me and often in haphazard ways. When I argued the Seila Law case on the constitutionality of the CFPB, the reason that I had the opportunity to argue that case was that the lawyer who had handled the case, a terrific lawyer from California by the name of Tony Visconti, had worked with me many years before on a pro bono cert petition.

When the Ninth Circuit issued its adverse decision in that case, he remembered me and called me. We talked about the case and ended up taking it on. Particularly as I get older, I find it’s often those coincidental occurrences. A client saw me speak at an event like this, remembered me, and a few years later called me to hire me for a Supreme Court case. This happened to me a couple of years ago.

There’s no one mechanism by which the cases come to folks like me. One interesting thing about my career, and this is pretty typical, is that the vast majority of the cases that I handle at the Supreme Court are cases that I didn’t handle in the lower courts. In some sense, that’s one significant difference from even cases at the Court of Appeals level.

A significant percentage of the cases that I do at the Court of Appeals level are cases that either my firm handled at the district court level or that I may have even had some involvement with at the district court level. At the Supreme Court, the cases that the court hears are so few. Often they’re not the types of cases that a big firm like mine handles at the Court of Appeals level. That’s one of the reasons why the inflow of cases can be somewhat haphazard.

Do you tend to get involved at the search stage typically? Do you get involved in all different parts of the process depending on the case?

It depends. In 2021, I had three arguments in court. One of those cases was a case where we did the cert petition. Two of those were cases where we represented the respondent. We didn’t get called until after the cert got granted. I much prefer to be involved in an earlier stage of the case because it gives you the opportunity to frame the case, particularly at the cert stage, which is very important, but it is what it is. Every case is different. Sometimes clients don’t realize until much later in the process that it makes sense to bring in someone who’s a Supreme Court specialist.

In terms of cases that you do in working at a larger law firm, do you have time for pro bono cases in the Supreme Court?

It’s one thing that my firm Paul Weiss is very committed to. That is pro bono work at every level of the court system. Our firm has an incredible tradition of pro bono work going back to its work on Brown versus Board of Education. The firm is extraordinarily supportive of pro bono work at the Supreme Court. We handled a very important case involving the Armed Career Criminal Act, the federal statute that imposes mandatory minimum sentences on certain repeat offenders.

We prevailed on an important interpretive question concerning that statute because my practice has always had a significant focus on criminal work. Most of the pro bono work I tend to do at the Supreme Court level is in the area of Criminal Law, but over the years, I’ve handled a variety of different types of pro bono cases at the court.

I’ve always heard of pro bono as being one way of getting into the US Supreme Court practice from observing others. Has that been your observation as well?

That’s often true. The reality is that the competition for Supreme Court cases is so great that even for clients who aren’t traditional pro bono clients, there is any number of lawyers who will offer to handle those cases for free. I’m often reminded of something that John Roberts said when he was not the Chief Justice of the United States but simply a country lawyer, which is, “If you need to have heart surgery done, you probably won’t go with the person who called you up and offered to do it for free.”

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Supreme Court: SGS offices are increasingly becoming similarly prominent.

There’s a lot of that going on in the Supreme Court bar. A relatively small number of us frankly can much less charge anything resembling our normal rates for Supreme Court work. The reality for younger lawyers who want to break into the Supreme Court bar is you have to do that to have those opportunities. That is a reflection of the fact that the court is taking relatively few cases. There are a lot of people who want to handle those cases.

I would think a lot of times that would mean getting involved prior to the Supreme Court in the District Court of Appeals somewhere along the line.

One thing that has changed is that when I started as a Supreme Court litigator, it was not at all uncommon for clients to bring in the Supreme Court lawyer only after a cert got granted. That does still happen, but that’s the exception rather than the rule. Usually, a case is fully lawyered up by the time the cert petition gets filed or certainly shortly thereafter. I do think that there is a lot of value to that.

The reality is that with the growth of Appellate Law, especially more generally, you have a lot of great appellate lawyers who are often involved in cases at the Court of Appeals level. If it’s a reasonably significant case, particularly for the business community, which are the clients that I tend to represent, chances are the clients are sophisticated enough that they’re going to have gotten a pretty good appellate lawyer involved even at the Court of Appeals level.

When you’re getting involved after a cert is being granted, does that change your approach to the case other than knowing you’re confined to what has been done before? Do you attack that case any differently than you would if you were building the case yourself?

I don’t think so. You’re certainly mindful of the rules concerning waivers, forfeiture, and the like. You don’t fly out those rules lightly if you come up with some brilliant new argument. You want to be sensitive to the fact that you are somewhat confined. Ultimately, your approach is the same in the sense that you’re trying to figure out what the very best arguments are that are going to get you to five votes in the Supreme Court.

Ultimately, the key at the Supreme Court level is to try to figure out as a strategic matter, given what you have to work with what is the best way to achieve your client’s desired result and which arguments are going to be the most appealing to enough members of the court. That’s the most important part of the process in some sense. I have sometimes said to my associates, “Once you figure out what the best arguments are, the briefing and the oral argument are about execution.” There’s a lot of truth to that at the Supreme Court level.

Frankly, there’s a lot of truth to that at the lower court level as well. If anything, you both know at the lower court level, it’s all about deciding which arguments you’re going to make and in what order you’re going to make those arguments, particularly when you have a case as is true in the case that I’m going to be arguing where you have three issues, deciding which issues to raise and how to prioritize those issues are crucially import.

How do you make your case stand out to get 1 of the 60 slots?

Everybody knows that there are certain basic principles about Supreme Court review. The Supreme Court typically only grants review to resolve conflicts among the lower courts, whether conflicts among the Federal Courts of Appeals or conflicts with state courts of last resort. That is certainly one of the keys. One underestimated aspect of Supreme Court review is that with the court hearing only 60 cases a year, you’ve got to convince the court that this case is worth its time.

That means coming up with the best arguments as to why the question that you’re raising matters to, for instance, a broad sector of the economy or why it’s going to matter to criminal defendants nationwide. That’s a part of cert petitions that people often don’t focus on as much as they should. People always are thinking about circuit conflicts. Everybody knows that you’ve got to raise a circuit conflict. You see a lot of cert petitions that raise them even when there isn’t one there.

That is certainly significant, but it’s all about the importance of the case. It’s also all about convincing the court that the lower court got it wrong. One interesting statistic that I unearthed when I was preparing for my talk is that the Supreme Court in 2021 reversed the lower court in more than 80% of the cases it heard, which to me suggests that the merits matter when the court is deciding which cases to hear. Although people often have the temptation of thinking, “You should leave the merits arguments to the merit stage of the case,” I find myself increasingly trying to make those arguments even at the cert stage to convince the Supreme Court that there’s something that it needs to correct.

It’s conventional wisdom before the Texas Supreme Court that the court does not grant to affirm. It sounds like, based on your observation, that carries through even up to the US Supreme Court too.

That’s typically true. There are some subsets of cases where the court is granting review plainly because there’s an important issue that the court needs to provide the final word on, but more often than not, when the court is granting cert, it’s because somebody thinks there’s something that went wrong in the lower court.

With the briefing and the cert petition process, what do you focus on in the cert stage? It’s certainly a different view as opposed to the merits briefing.

It’s all about convincing the court why a case is worth its time. One of the things that we try to do in our cert petitions is not to make it too complicated. One thing that I often say to our associates is, “If you’ve got to use all 9,000 words to convince the court that it should hear a case, it probably suggests that you don’t have a very compelling reason for the court to hear it.” I filed cert petitions 12 or 15 pages long that have been granted because sometimes, making your pitch straightforward and elegant is the way to go.

That’s true. When you get to the merits briefing stage, you want to brief the case thoroughly, but does that observation hold true sometimes, too, with merits briefs? Do you tend to push word count on those? Do you tend to be brief?

It’s a lot harder at the merit stage in the Supreme Court to file a shorter brief. I was impressed in the last term in a case called Badgerow. A Texas lawyer, Dan Geyser, filed a brief that was around 30 pages long. It was well under the word limit. He ended up winning the case. I haven’t talked to Dan about this, but he probably made the judgment that, as a strategic matter, it was much better to keep his pitch at the merit stage relatively simple.

It’s something I aspire to do, but it’s so hard because when the court grants review in a case, it’s because there are substantial arguments on both sides. There’s an interesting legal issue. It’s an issue that a lot of people have written a lot about. It’s tough. I aspire to file shorter merits briefs, but it’s the exception rather than the rule.

The Supreme Court practice is not something I do but one thing I’ve observed, and you touched on this earlier, is when you’re writing a brief in that court, you’re writing much more from a blank slate as opposed to relying on precedent. It seems like that would be a tremendous challenge in terms of presenting the argument to the court and the mindset you have to be in when you realize it.

You do deal with this every day. I don’t. You realize, “What is precedent in this court? How do I couch the issues? Is it in line with precedent versus some of the other first principles you pointed out?” That, to me, would present a unique challenge. I would have a hard time filling in all the word count for that limit. I’m so used to writing on a precedential basis as opposed to this original thought. I admire that whole approach. It’s very interesting.

One of the things that I think about a lot, both at the Supreme Court level and more generally, is that whenever you write a brief, in some sense, you have two audiences. The one is the judges who you are trying to persuade. First and foremost, you always want to make the arguments as to why the judges should rule in your favor. The second audience is the law clerks and the judges themselves when they go back and write the opinion.

I often think about what things somebody would want to know when writing the opinion and the details they need to be aware of in the drafting process. Sometimes I feel a certain degree of tension between those two things because the stuff that you want to let the law clerks and judges know when they’re writing the opinion is the stuff that you often put in the footnotes. There’s often a lot of detail that goes into that, but that’s the intention of presenting a very clean and straightforward pitch as to why you should win.

This sounds like a silly question, but how important is the record? They’re deciding a lot of these nationwide importance questions. Your record is certainly a vehicle, but how much do you play it up or not play it up?

People tend to understate the importance of the facts at the Supreme Court level in part because when the Supreme Court grants review, it does grant review on a legal question presented. There’s a tremendous temptation to deemphasize the facts, but the facts matter to the overall story, particularly when you have relatively sympathetic facts.

I often spend a lot of time figuring out how to frame the facts in a way that presents a narrative consistent with the outcome we want to achieve on the legal question. I’ve certainly heard the Chief Justice and other members of the court talk about the importance of that narrative in a brief. To me, you get the reader’s attention by telling a compelling story about the case, how the case ended up in the Supreme Court, and the parties to the case. That’s a part of the brief that we certainly spend a lot of time thinking about.

Another area in getting the court’s attention where it’s maybe more important than any other court is amicus support. How do you intentionally use amicus to your advantage to get the court’s attention in ways that your cert petition can’t because of word limits and whatnot?

One of the things that have also changed over the course of my time practicing before the court is the sheer volume of amicus support, not just in the highest-profile cases but even some of the lower-profile cases as well. When you’re representing a party before the Supreme Court, it’s important to manage that to the extent you can. Sometimes you have more control over that than other times.

What you want in an ideal world is for the amicus briefs not to be repetitive but to be complementary to make points that might be uncomfortable for you to make as the party, to provide a broader perspective as groups often can about the implications of a ruling in your client’s favor or a ruling against your client, to try to coordinate that so that the amicus briefs aren’t going to simply waste the court’s time, and to try to maximize the likelihood that those briefs are going to get read, not just by the law clerks but also by the justices.

Frankly, there’s often too much of an emphasis on the amicus briefs. To me, in the vast majority of Supreme Court cases, a well-written brief for the party can cover 99% of what needs to be covered. Carl is one of the great amicus brief writers precisely because he’s very good at doing that. He’s good at providing distinct arguments from different perspectives. A lot of amicus briefs, particularly in the big cases, don’t add much value at all. In the bigger cases, the amicus briefs are already starting from a disadvantage because if you have a case where there are 50 amicus briefs on each side, the likelihood of those briefs being read is pretty small, to begin with.

Do you coordinate that as the person who’s taking the case to the Supreme Court to the extent you can? I recognize some of it is outside of your control.

It’s no secret that the lawyers for the parties do try to coordinate that. At the same time, one thing that I’m very mindful of is that an amicus brief is still a brief being filed on behalf of a client. It’s ultimately for that client to decide what they want to say. You try to be respectful of that in the coordination process because the best amicus briefs are briefs that authentically represent what a group thinks that aren’t efforts by the parties to get another 50 pages or 30 pages for their brief. You want that amicus brief to speak distinctively in the voice of the actual amicus.

How do you prepare for a Supreme Court oral argument? I recognize it’s a very different game than preparing for a Court of Appeals argument. How do you go about that?

The preparation process is pretty similar. The actual oral argument is different for a lot of the reasons we have discussed. In the end, what I do is sit in my office with the briefs. I reread the briefs a gazillion times before any oral argument because the first goal of an advocate is to know what you’ve argued already to the court and be the master of that. I’ll read whatever is essential. That depends on the type of case. If it’s a case that is very case-heavy, I’ll spend a lot of time reading the prior decisions of the court that are significant.

In a complicated Supreme Court case, that can be 40 or 50 cases that you have to master. In a simpler case, it might be 6 or 7, but you want to master the key precedents. If it’s a case involving statutory interpretation, you want to master the relevant statutes, regulations, and so forth. In the preparation process, whether it’s the Supreme Court or a lower court, I transition pretty quickly into trying to figure out what the hardest questions are for our side and what the best answers to those questions are.

I will often keep a running list of those questions so that I have them in front of me as I’m preparing. That leads naturally to the most important part of the preparation process, which is doing moot courts for oral arguments. I typically do two moot courts for Supreme Court arguments. In an ideal world, I’ll do two moot courts for a Court of Appeals arguments as well. I view that as the central part of the preparation process. It’s getting great and smart lawyers to come and be mock justices or judges and get a sense of what someone who is new to the case is going to have on their mind after reading the briefs.

People often talk about whether a mooter should replicate particular justices. I don’t try to operate on that level. I don’t try to figure out who in my friends is going to do a good Justice Kagan or a good Justice Alito. Instead, what I try to do is to get people who think like appellate judges. They’re typically appellate lawyers who are going to be able to replicate that reaction of what a smart person is going to think after reading the briefs.

For Court of Appeals arguments, what I’ll do is invite associates from my firm Paul Weiss to come and be the mooters. Often clients will say, “These are associates. You’re the partner who’s the head of the practice. They’re going to be obsequious.” They listen to the moot for about two minutes and realize that’s not how it works. The moot courts are the opportunity for associates to take out their aggression on me. They were very good at doing that. I often have moments of thinking, “There’s no respect being paid to the boss here, but that’s how it should be.”

This is a game of stump the boss.

It’s a great opportunity for associates to show their stuff. I’ve often had clients say after a moot court, “Your associates are so impressive.” Typically, I try to get people who haven’t worked on the case before. It’s a great way of getting young lawyers exposed.

Here’s one thing I wanted to ask you about. You’ve touched on this earlier. How do you mentor in a Supreme Court practice? There are so few opportunities for advocacy at the court and cases getting taken. How do you pass those opportunities along to those you’re trying to bring up?

It’s very hard because there are so few opportunities to argue cases before the court. Even at the Court of Appeals level in a big appellate practice, when a client is hiring us to handle the case, they typically want to have the senior person in the practice do the actual oral argument, unlike with trial practice where there are lots of opportunities for lawyers to stand up in the course of a trial. There’s only one opportunity to stand up in an appellate case.

That’s often as little as 10 or 15 minutes of the oral argument. It’s important as the head of practice to constantly be looking for argument opportunities for younger lawyers, both pro bono opportunities but also perhaps on smaller matters for our bigger-paying clients. That’s something that has always been important to me. The most important thing is giving lawyers as much responsibility as possible early in their careers.

Particularly on our Supreme Court briefs, it’s not unusual for me to be the only partner on the briefs. It’s important for associates to take on that brief writing responsibility as early as they can possibly do it. That’s how you develop a reputation as a top-flight appellate lawyer. It’s first as somebody who writes good briefs and then hopefully as somebody who is a super oral advocate later in your career.

I don’t want to let you go before we talk a little bit about your presentation. The subject of your presentation is the US Supreme Court update. We don’t have time for you to launch into your entire presentation, but that would be very interesting. Jody and I look forward to attending that here shortly. Would you share a couple of your hot takes from the term and things you intend to cover during the presentation? I don’t think we would be doing our job if we didn’t ask you to highlight some of your hot takes from this last term.

lawyer arguing in court in front of judge
Supreme Court: When you’re arguing in the Supreme Court, it’s hard not to feel a sense of awe at the occasion.

I’m not sure that any of these are going to qualify as hot takes, but it is such a fascinating time to be watching and practicing before the Supreme Court. We saw the Supreme Court strike out in a pretty clear jurisprudential direction in 2021 in a lot of major areas of the law. First and foremost, we had the abortion decision in the Dobbs case, but this felt like an exceptionally consequential term across a variety of different subject areas.

When I think back on my time practicing before the Supreme Court, we have had a Supreme Court for a long time that has been in relative equipoise. It has been a 5-4 Supreme Court on a lot of the most significant questions of law. The identity of the so-called swing justice has changed over the years from Justice O’Connor to Justice Kennedy and then, for a brief time, seemingly the Chief Justice. Now we have a Supreme Court that is 6-3 Supreme Court in a lot of significant areas that has not been afraid to revisit precedent in a lot of key areas.

It’s more than a little bit of a change. It’s a significant change for those of us who are used to a court that swung in a so-called conservative direction in some cases and a more liberal direction in others. It’s going to take some period for all of us to adjust to that. We have a number of new members on the court. We have had four members join the court in the last few years.

Particularly given the shift in the court’s jurisprudential direction, there are a lot of areas of the law that the new membership of the court has not yet addressed. The court is going to tackle a lot of significant areas of the law and issues like affirmative action, the First Amendment, and others next term. We will have a better sense of how profound this shift is by the end of next term when the court tackles some of those questions.

For purposes of the business community, the primary group that I represent, the court has not tackled a lot of the meat-and-potatoes issues that affect businesses like preemption, class actions, and Patent Law, which is an area that the court had previously been very active in but has not been as active in over the last few years, the Securities Law, and Antitrust Law. There isn’t that much on the docket for next term in those areas of law, either. It’s going to be a little while before we have a good read on how this newly constituted court thinks about those issues.

We have reached the end of the time that we had planned to spend together, Kannon. Hopefully, you have had some time to think about this. It’s our tradition to ask our guests for a tip or a war story before we end the show. Do you have something that you would like to offer our guests?

I’m reminded of a story about my first oral argument. I argued my first Supreme Court case in 2004 when I was in the Solicitor General’s office. It was a criminal case called Muehler versus Mena. I remember it like it was yesterday. I turned up at the court. We were the second case on the calendar, which is never ideal because it means that you have an extra hour to sit there and think about the fact you’re going to be arguing a case before the Supreme Court.

I was sitting at a council table with Michael Dreeben, the long-time deputy SG who had responsibility for criminal matters. I must have looked pretty green, as in literally green, not metaphorically green, because right before the argument started, Michael leaned over to me and said, “Kannon, if you’re going to throw up, be sure to throw up on the opposing counsel and not on me.” To this day, I’ve always thought that’s the best piece of advice. If you’re going to throw up, throw up on the other guy. Thankfully, I managed to get through that argument without getting sick. I haven’t felt nearly as nauseous since.

Thank you so much. We appreciate you giving us this time.

It was great to be with you both. Thanks for having me.


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About Kannon Shanmugam

Chair of the Supreme Court and Appellate Practice Group and managing partner of the Washington office, Kannon Shanmugam is widely recognized as one of the nation’s top appellate lawyers. He was named 2021 Appellate Litigator of the Year by Benchmark Litigation and is a finalist for The American Lawyer’s 2022 Litigator of the Year. Kannon has argued 35 cases before the Supreme Court, including three cases in the 2021-2022 term. In all, he has argued over 100 appeals in courts across the country, including arguments in all thirteen federal courts of appeals and in numerous state courts.

A recent study found that, over the last five years, Kannon had the highest rate of successful petitions for review of any Supreme Court practitioner. He was lead counsel in the successful constitutional challenge to the structure of the Consumer Financial Protection Bureau, described by the Wall Street Journal as the “constitutional case of the year.”

Prior to private practice, Kannon served as an Assistant to the Solicitor General at the U.S. Department of Justice. He also served as a law clerk to Supreme Court Justice Antonin Scalia and to Judge J. Michael Luttig of the U.S. Court of Appeals for the Fourth Circuit.

Benchmark Litigation noted that Kannon is “one of the most respected and admired appellate practitioners” in the country. One longtime Supreme Court reporter recently said that Kannon “has perhaps the most eloquent and elegant manner … that I’ve ever seen in my 40 years covering the Court,” adding that he “projects calm, confidence, and authority from the moment he takes to the lectern.” Chambers USA described Kannon as “famous for his unflappable, calm, and disarming manner at oral argument,” and praised him as an “impeccable writer” and “great strategic mind.” Legal 500 called Kannon “a brilliant lawyer and tactician, with impeccable judgment and an optimal moral compass.”

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