Welcome to Original Jurisdiction, the latest legal publication by me, David Lat. You can learn more about Original Jurisdiction by reading its About page, and you can email me at davidlat@substack.com. This is a reader-supported publication; you can subscribe by clicking here.
For longtime observers of the legal profession, here’s a headline we wouldn’t have expected a few years ago: “The Eight-Figure Talent Race for Supreme Court Lawyers.” According to C. Ryan Barber and Erin Mulvaney of The Wall Street Journal (gift link), superstar SCOTUS advocates—including former solicitor general Elizabeth Prelogar, now at Cooley, and former acting SG Jeff Wall, who recently joined Gibson Dunn—are commanding pay packages previously unheard of for appellate practitioners.
For such a small and elite group, the Supreme Court bar has seen a striking amount of movement in the past few weeks. In April, Wall led a four-partner group that decamped from Sullivan & Cromwell to Gibson. A few days later, another leading high-court litigator, Kannon Shanmugam, left Paul Weiss and joined Davis Polk & Wardwell, where he now heads the firm’s new Supreme Court and appellate practice group.
What explains this flurry of movement in the SCOTUS space? Why are top firms investing so heavily in Supreme Court and appellate practices? And what broader trends might this reflect?
I could think of no better guest to explore these topics than Kannon Shanmugam. Not only did he recently go through the recruiting process as a lateral partner, but he’s now going to be doing some hiring of his own, as he and Masha Hansford build out what Kannon hopes will be “the very best appellate practice in the country.”
Thanks to Kannon for speaking with me, and congratulations to him and Masha on their move to Davis Polk.
Show Notes:
Kannon Shanmugam bio, Davis Polk & Wardwell
Kannon K. Shanmugam profile, Chambers and Partners
Davis Polk Looks to Appellate Star Shanmugam to Elevate D.C. Build, by Meghan Tribe for Bloomberg Law
Sponsored by:
NexFirm helps Biglaw attorneys become founding partners. To learn more about how NexFirm can help you launch your firm, call 212-292-1000 or email careerdevelopment@nexfirm.com.
Three quick notes about this transcript. First, it has been cleaned up from the audio in ways that don’t alter substance—e.g., by deleting verbal filler or adding a word here or there to clarify meaning. Second, my interviewee has not reviewed this transcript, and any errors are mine. Third, because of length constraints, this newsletter may be truncated in email; to view the entire post, simply click on “view entire message” in your email app.
David Lat: Welcome to the Original Jurisdiction podcast. I’m your host, David Lat, author of a Substack newsletter about law and the legal profession also named Original Jurisdiction, which you can read and subscribe to at davidlat.substack.com. You’re listening to the ninety-ninth episode of this podcast, recorded on Thursday, June 4.
Thanks to this podcast’s sponsor, NexFirm. NexFirm helps Biglaw attorneys become founding partners. To learn more about how NexFirm can help you launch your firm, call 212-292-1000 or email careerdevelopment@nexfirm.com. Want to know who the guest will be for the next Original Jurisdiction podcast? Follow NexFirm on LinkedIn for a preview.
We’ve entered the month of June, and OJ readers know what that means: time to focus on the U.S. Supreme Court, which will be handing down some of its biggest decisions over the next few weeks. And it’s also a good time to talk about the Supreme Court bar—which has seen a remarkable amount of movement this year.
In the span of less than a week in late April, we saw two major moves by groups of Supreme Court and appellate practitioners. We first learned about Jeff Wall, Morgan Ratner, Judd Littleton, and Yaira Dubin moving from Sullivan & Cromwell to Gibson Dunn & Crutcher. And then, a few days later, Kannon Shanmugam and Masha Hansford left Paul Weiss and joined Davis Polk & Wardwell.
And now, Kannon is joining me, right here on the Original Jurisdiction podcast. Most of my listeners are familiar with Kannon—but for the few who are not, he’s one of the nation’s leading SCOTUS advocates, with more than 40 Supreme Court arguments under his belt. He clerked for the late Justice Scalia, served as an assistant to the solicitor general at the U.S. Department of Justice, and led the Supreme Court and appellate practices at three top law firms: Williams & Connolly, Paul Weiss, and now, Davis Polk. Without further ado, here’s my conversation with Kannon Shanmugam.
Kannon, thank you so much for joining me.
Kannon Shanmugam: It’s my pleasure, David.
DL: So this is not the first time we’ve spoken, but for the benefit of my readers who somehow are not familiar with you, tell us about your background and upbringing. Where did you grow up?
KS: I grew up in Lawrence, Kansas. I’m a proud Jayhawk by birth. I spent most of my childhood in Lawrence. My parents emigrated from India a few years before I was born. My father was for many decades a professor at the University of Kansas, where my brother still teaches. I nevertheless flew the nest and went to Harvard for college and then also for law school, with two years at Oxford in between.
I then moved here to Washington, where I’ve been ever since. I clerked first for Judge Michael Luttig on the Fourth Circuit, and his chambers were right across the river from here, in Alexandria. And then I was fortunate enough to clerk for Justice Scalia at the Supreme Court, and then started my legal career in private practice, working with Ken Starr in what was then one of the few appellate practices at Kirkland & Ellis. In 2004, I left for the Solicitor General’s Office, the office that handles the government’s litigation in the Supreme Court. I was there for four years, and then in 2008 I came out into private practice. And as of six weeks ago, I’m a partner here at Davis Polk.
DL: So let’s double back a little. You may not remember this, but we actually met a million years ago in college, when you interviewed for a resident tutor position at the house I was in—I think I actually have an ancient copy of your resume in my file somewhere. But let me ask you this: what led you to go to law school, especially since you mentioned your father was an academic, but not a legal academic?
KS: So I didn’t get that resident tutorship position.
DL: That is true—don’t hold that against me! It was a committee decision.
KS: I’ve overcome that failure, David, somehow. I’m glad we’re still friends despite that.
But I never really wanted to be an academic. I had tremendous admiration, not surprisingly, for my late father. He’s one of my heroes. But it just wasn’t really the lifestyle for me. I really like being in the arena. And so either when I was in graduate school studying the classics (which was also my undergraduate subject) or after law school, I never really thought about being a law professor. I enjoy teaching the occasional class, and I hope I will continue to do that. And I love higher education; I joined the Harvard Corporation, which is the board that runs Harvard University, and it’s been a really fascinating thing to learn more about the university and how it operates. But it’s never really been the full-time vocation for me.
DL: I’m about to head up to Cambridge for my 30th college reunion, so as an alum, I’m very glad to see you on the board, especially since our alma mater certainly could use some legal help right now. But let me ask you: you majored in classics—not poli sci or “Government,” as it’s called at Harvard. Why did you pick the law?
KS: Well, when I was in college, I was pretty sure I didn’t want to be a professor, and I was pretty sure I didn’t want to be ambassador to the Vatican. So I knew I was going to do something other than the classics after I finished graduate school. And the two main things I was thinking about were journalism and law.
I was the editor of The Independent, which is the weekly newspaper at Harvard, and thought really seriously about a career in journalism. But I always had an interest in government and politics, so the law was always a possibility. And as I went through my college career, and as I spectacularly failed to get various jobs at leading newspapers for the summer, I came to realize that journalism was going to be a tough field to break into—and that was when the internet was in its infancy. So I decided on law school instead.
DL: Well, I can relate to that. I worked for your rival publication, The Harvard Crimson, and in my senior year I was looking at journalism jobs. My parents saw that they paid, I don’t know, $25,000 or $30,000—and as immigrant parents, they basically said, “No way.” So I wound up in law school. And unlike you, I went straight through.
So let me ask you this. You had a great experience at Harvard Law School. You totally cleaned up there. You wound up clerking for two very distinguished judges. One of them, former Judge Michael Luttig, is now a major commentator on events in the news. He went from being on the Fourth Circuit and a Supreme Court shortlister to the general counsel of Boeing, to now, in some ways, a public intellectual, I would say. I’ve talked to some conservatives who are a little puzzled by him, and I’ve talked to other people who basically view him as their hero. Do you have any thoughts on the evolution of J. Michael Luttig?
KS: Well, he has definitely had a lot of acts, as you say—first as a court of appeals judge, a fabulous court of appeals judge; it was a great privilege to clerk for him. And then as you say, he was general counsel of Boeing, and he is now a leading presence on social media and commentator on present events. I can’t really speak to his current political thinking, but I will say that he is a very thoughtful and serious person—and when he was a judge, a great role model for me in the early years of my career.
DL: I will not disagree with any of that. He is certainly a very thoughtful person, whether you agree or disagree with the particular positions he takes.
So you spent time in the Office of the Solicitor General. That, of course, must have been an amazing experience. How would you characterize that?
KS: For an appellate lawyer, it is a foundational training experience, and it’s no accident that many of the leading appellate litigators cut their teeth in the Solicitor General’s Office. It was just a tremendous professional opportunity to get to work on and even argue Supreme Court cases at such an early stage of my career.
And I was fortunate to be in the office at a time when there were a lot of legends there. Ted Olson was the solicitor general who hired me into the office at the time. Ed Kneedler and Michael Dreeben were among the deputies. Even among the assistants—which was the level that I was at—you had people like Jeff Minear and Irv Gornstein and Jim Feldman and Malcolm Stewart, who’s now one of the deputies, and so many others who were just extraordinary lawyers and role models, in the way that they thought about the law as well as in the very ethical way that they made representations on behalf of the United States. And so it was without question the formative experience of my career.
I was lucky that I was relatively young when I was in the Solicitor General’s Office, because I think I probably didn’t know enough to realize how nervous I should be about arguing cases in the Supreme Court. I was still in the heady days of youth and felt very confident in my own abilities. And so I probably didn’t feel quite as nauseous as I should have before each of those arguments when I was in the government.
DL: I actually totally concur with your thought that the older we get, the more we realize our limitations. When I was an undergraduate or law student, I thought I was so brilliant, and now I realize the limits of my own knowledge and abilities.
You were actually at Kirkland with former judge and solicitor general Ken Starr before you went to the SG’s office—one of the few appellate and Supreme Court practices around at the time. And it’s very interesting because your career trajectory, in many ways, mirrors or reflects the rise of a specialized Supreme Court and appellate bar. This is a very big-picture question, but do you have general thoughts on that, and whether that is a good or bad thing for the Court and for its work in deciding cases?
KS: I don’t think it’s a bad thing—perhaps that’s not surprising—I think, by and large, it’s a good thing. But I think it really reflects a broader trend in the law, which is the ever greater degree of specialization in legal practice—and perhaps that’s not surprising, because we have many more lawyers in the profession than we did 25 or 50 years ago.
So, as in many other areas of practice, people have come to recognize that it takes a particular set of skills and a particular type of knowledge to be an effective appellate advocate. Certainly the form of advocacy in the appellate courts is very different from the form of advocacy in trial courts before juries. If anything, it’s probably evolved even further away from district-court advocacy.
And the reality in the American legal system is that the appellate courts are where cases ultimately get resolved. We have a system that places a lot of weight on juries, but juries sometimes make mistakes. So we really rely on a robust appellate court system in this country to get things right. And so for clients, if clients have big disputes, they really need to have the best lawyers at the appellate level.
Now, sometimes that’s misleadingly characterized as a Supreme Court practice, and I’ve been fortunate to have had a number of arguments in the Supreme Court—but the reality is that most big commercial disputes actually end at the court of appeals level. And so in many ways, if you ask what I do on a daily basis, I’m at least as likely to be arguing something in a federal or even a state appellate court as I am in the Supreme Court.
And it’s funny, as I was thinking about my decision to join Davis Polk, I was talking with a friend of mine, and she said to me, “It’s a little bit misleading to describe your practice as even an appellate practice. What you really do is you help marquee clients with their most difficult issues.” And that, I think, is actually a very accurate way of capturing what lawyers like me do for a living: we help our clients with their most difficult legal issues, wherever a case may be in the lifecycle of litigation.
DL: There has been this evolution, because on the one hand, you’re right, there’s been this greater specialization—but on the other hand, it seems to me that what it means to be an appellate and Supreme Court litigator has changed. Because one thing I’ve heard, and what some of your colleagues have told me, is you don’t argue just in the Supreme Court, or even in the state and circuit appellate courts. You’re also brought into complex litigation, maybe as a case is about to be filed or even before a case is filed, to strategize and brainstorm.
So I guess if we were to think—shout out here to Advisory Opinions listeners—of buckets, we have the Supreme Court bucket, we have the state and federal appeals court bucket, and we have another bucket helping trial teams or counseling or what have you. How would you say, typically, if we were to average or wash it all out, that your practice breaks down into those buckets? And if I’ve missed a bucket, feel free to add it.
KS: No, I think that covers almost everything. And I would say that at any given time, one bucket may be fuller than the others.
So just to give you a sense of what I’m working on right now, I think our Supreme Court bucket is actually probably the fullest bucket right now, just because I recently argued a Supreme Court case shortly after I came over to the firm. We have two cases on the docket for next Term already, one of which I’m taking the lead on, the other one of which my brilliant partner, Masha Hansford, is taking the lead on. And so those are just taking up a lot of bandwidth right now. But if you go back over the last two or three years, I could certainly identify times when the other buckets have been the fullest buckets, and in particular, the district-court bucket can sometimes be fairly time-consuming. And often those are cases where the matter is inevitably going to end up in an appellate court and the client has just brought someone in sooner.
I was having dinner earlier this week with the general counsel of one of our clients, and he said, “Kannon, we have this case that’s going to trial later on this year. I’d love to get you involved because there’s some really novel and significant legal issues that we’re going to need to figure out our positions on and our best arguments on.” And so that’s a case that isn’t even in trial yet where the client is looking for advice, and that’s pretty common nowadays.
So I really do think that that’s the value of these practices. In many ways, labeling them as “Supreme Court” or “appellate” practices is a little bit misleading. What we do is really more like a combination of what the Solicitor General’s Office does and the Office of Legal Counsel does within the Justice Department: we help with difficult legal issues, wherever they might be in the process.
DL: I know that you said it’s going to vary a lot—but of those three buckets, is any of them consistently over 50%, or not really?
KS: I think the court of appeals bucket is probably by volume the most significant—because if you take a typical year, a good year for a Supreme Court advocate is three or four arguments, barring something really unexpected happening. But a typical year for me in the courts of appeals is about a dozen arguments, and sometimes it can be more than that. And if anything, cases in the courts of appeals can sometimes be even more labor-intensive to prepare for than cases in the Supreme Court, because cases in the Supreme Court often involve these neat, discrete legal issues. And it’s not unusual, as you know, to have a case in the court of appeals where you have a big trial, very fact-intensive arguments, and four or five legal issues. And so if you looked at my sheer hours, I think work in the appellate courts is probably year-on-year the most significant.
DL: That makes total sense to me. So I will not rehash your move from Williams & Connolly to Paul Weiss; we’ve talked about that when I had you previously on another podcast I used to host, and also in an interview I did in the early days of Original Jurisdiction. But I want to touch on your move from Paul Weiss to Davis Polk.
So when you moved to Paul Weiss from Williams & Connolly, you kind of set off a little game of musical chairs, because then Williams & Connolly went out and brought in Lisa Blatt, and then Arnold & Porter went out and got John Elwood. And similarly now, there seems to be this flurry of movement in the appellate space. I know from my brief detour into recruiting that these deals take a long time to work out, and so it’s hard to tell when a deal is announced versus when it was in the works. But do you have any thoughts on this flurry of movement in the Supreme Court and appellate space? Because around the same time that you moved from Paul Weiss to Davis Polk, there was a group of other star Supreme Court and appellate advocates, including Jeff Wall and Morgan Ratner, who went from Sullivan & Cromwell to Gibson Dunn. If you go back a little bit farther, of course, Elizabeth Prelogar returned to Cooley. And there’s just been a lot of movement in that space; I could mention a whole bunch of other people. So I guess my question is: all this movement in the SCOTUS and appellate space, what’s up with that?
KS: Well, I don’t know that it’s a huge amount of movement, and I think it certainly is true that the two times that I’ve moved firms, there have been other moves at the same time or roughly at the same time. But there were seven years in between those two moves; I had seven wonderful years at Paul Weiss. And I think the reality is that perhaps it seems as though there’s more movement in the appellate space because often you have people coming out of government, like Elizabeth Prelogar. Historically, there have been a lot of people who’ve gone from our area of practice into government jobs, into the judiciary, and the like. And I also think that the velocity of movement to and from law firms has gone up in recent years, just more generally. So in some sense, this may just be reflective of a broader trend. But in the appellate area in particular, what it probably reflects is a recognition on the part of firms, including firms that historically have not had these practices, that they can really add value to the litigation practices of the firms as a whole and to the firms more generally.
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Now, this is kind of an awkward subject, but it’s been reported that some appellate stars are getting these gigantic, eight-figure pay packages. I’ve speculated in the pages of Original Jurisdiction about your compensation—you don’t need to address that—but what do you think justifies these pay packages? Because the old narrative about Supreme Court and appellate practice was, “Oh, it’s prestigious, it helps with recruiting, but it’s not leveraged, and it doesn’t make quite as much money.”
But I was speaking recently to the head of litigation at a firm that made one of these big appellate hires, and this partner told me something very interesting. They said that having an appellate or Supreme Court marquee name is actually really critical to winning the biggest litigation matters, period—because this person was grousing that before they hired this appellate star or stars, they had lost some beauty contests to places like your shops who could say, “Well, if this doesn’t go as well as planned, or if we need high-powered brain work at the front end, we also have so-and-so.” So they basically say, “We have these great trial lawyers, but we also have this sort of brain trust of Supreme Court and appellate stars.” And so if you win one or two or three of those matters because of the presence of a Supreme Court or appellate person, maybe that person has paid for themselves because, given what billing rates are, billing in major matters can go well into the tens of millions or even the nine figures.
So is that part of it? How would you explain why some prominent Supreme Court and appellate litigators are commanding, reportedly, $12 million or $15 million or even $20 million pay packages?
KS: So I won’t speak specifically to the issue of compensation, but I will speak to the issue of why appellate practices are seemingly valuable to firms generally. One of the reasons is the reason you said, David, which is that when you are attempting to bring in significant litigation matters, this is a capacity that clients expect to have, and they expect to have it not just at the back end but at every stage of the litigation. And so it’s very important to be able to offer someone who is credible as an appellate advocate, whether or not you’re going to have that person argue the motion to dismiss, or whether or not you’re just going to have that person available to advise on the litigation at the early stages. And so I think that that is unquestionably valuable.
But I’ve always disputed the premise that appellate practices are somehow by their terms not valuable. I don’t know quite why appellate practices have always had that rap, and I suppose that if you were spending all your time pursuing Supreme Court cases at all costs and offering to do them for free, maybe that practice would be less “valuable.” But I think that when a general counsel of a big company calls you up and says, “We have a billion-dollar problem that’s heading to the Second Circuit,” it’s pretty valuable to be able to handle that case for the client, particularly if it’s a client who’s coming to you anew at the appellate level who may not be someone who was a client before that. And these are cases where clients are typically willing to pay the bills. So I think in terms of the economics of all of this, I’ve always thought that appellate practices are valuable for that reason, in addition to all of the intangible reasons why having a leading appellate practice is valuable to the reputation of a law firm.
DL: I totally agree with you, and you can certainly think of it in terms of dollars and cents. I once talked to the head of litigation at a major bank who hired one of your competitors, and this competitor got a nine-figure judgment from a lower court reversed in the court of appeals. It didn’t go to the Supreme Court, but getting a nine-figure judgment reversed or vacated or what have you—what’s a cut of that? It’s significant.
But let me ask you this, to sort of play devil’s advocate or to steelperson the rap on appellate practice. I think the classic argument was that it’s not leveraged. You can’t throw 50 or 100 warm bodies at these matters to do document review. I’m guessing—and maybe you can bake this into your answer to my ramblings—that typically you can staff an appellate matter with a partner or two partners, an associate or two associates, or three or four, but not 50. So I guess the argument was that you just couldn’t do leverage—your thoughts on that?
KS: So David, I would dispute the premise a little bit, because I don’t think that there are that many matters anymore where you have 50 or 60 associates working on the matter. The reality is that much of the work that associates were doing 25 years ago when I started in practice has long since been mechanized—and now with the rise of AI, associates simply aren’t doing that work anymore, and clients are increasingly coming to firms like ours simply because they have major complicated legal problems often involving novel legal issues. And the reality is that if the stakes are high enough, you can handle those cases without 50 or 60 lawyers and do so in a way that serves the client’s interests, but that is still economically rational for everyone involved. And on a typical appellate matter, we will have a team of four or five lawyers, and I think that that’s typically the right size to serve our client’s purposes.
DL: Obviously, I’m not asking about any specific representation, but how would you describe your approach to billing nowadays? Have you seen any kind of change in the billable hour versus alternative fee arrangements? And if so, in what direction? Or have you not really seen a change?
KS: That’s probably an issue above my pay grade, because all I see is my area of practice. And I think that appellate work has always been a type of work that is susceptible to alternative fee arrangements because it’s usually relatively easy to predict how much work is going to be required upfront. I think that gets more difficult with other types of litigation, but I think at least for appellate work where you typically know that it’s going to be two written briefs and an oral argument, you can do that if clients prefer, and some clients do and some clients don’t.
DL: Do you have a rough percentage of what your practice breaks down into in terms of X percent of revenue is billable hour versus alternative fee arrangement?
KS: That’s really hard to say, David; I don’t know that I’ve ever really tried to quantify that. It really varies from time to time, and it just depends on the client.
DL: But it’s probably still fair to say, as I think most lawyers in your position would, that the billable hour is still dominant? It has to be.
KS: I think so. Certainly in my personal experience, I think that’s right.
DL: So I definitely want to delve into a couple other matters, including the Court, but it would be podcaster malpractice of me to not ask you a little bit about why you left Paul Weiss. Now, of course, I understand and I will already preempt your response about how you were going toward an opportunity at Davis Polk. It’s an amazing firm. Nobody disputes that, etc., etc.
But were there any factors related to Paul Weiss that led to your move? I’ll mention two. One, the controversial deal that the firm struck with the Trump administration—and I have to say, I give you props for being more willing to speak about this deal than any other partner at Paul Weiss—and two, the argument that Paul Weiss has been shifting to a more transactional practice rather than a litigation practice.
So I guess that’s my question: Did anything about Paul Weiss lead you to this move, as opposed to the attractiveness of the opportunities at Davis Polk, which I will not dispute?
KS: Well, it was really an attractive opportunity. So even if you’re going to try to preempt me, I’m going to say that, because it was a very attractive opportunity, and it has been wonderful in the first six weeks so far.
I wouldn’t want to say anything critical about Paul Weiss, David, because I had seven great years there. As I said to my colleagues when I left, I wouldn’t be the lawyer I am today but for my experience there. I had some of the most enjoyable years of my professional career there.
I think I’ve always had a simple ambition, which is to have the very best appellate practice in the country, and I would say that over the months leading up to my departure, I thought really long and hard about where would be the best place to do that for the remainder of my career. And in that, I very much had a partner in my colleague, Masha Hansford, who came over with me and who I believe is the finest appellate lawyer of her generation. And we thought about this and talked about it a lot. We were very deliberate in how we went about doing it. And I’ll tell you, David, that a few months before I came over to the firm, I remember I was sitting in a coffee shop in New York, and I remember thinking to myself, if I were ever to leave Paul Weiss, where might I want to go? And I made a list, and I will tell you that Davis Polk was at the top of that list, and it was at the top of my list even before I had any idea that the firm would be interested.
Now, why was that true? I think it was for three reasons that ultimately ended up being the reasons why, when the firm invited me to join the partnership, I was very excited to do so, as was Masha.
The first is the reputation of the firm. I think that there is perhaps no firm that has a better reputation in the world at large among clients, and among fellow lawyers, than Davis Polk does. Second, the culture of the firm. Even when we were in law school, it had a reputation for being a very friendly, collaborative culture, and I think it has retained a team-first mentality that I’ve found very attractive, rather than an individual-first mentality. And so being in a place with a strong culture was very important to me. And the third was the quality of the management of the law firm. This law firm has management with a very clear vision for what a successful law firm in the modern era should look like. And in my conversations with our great chair and managing partner, Neil Barr, and others here at the firm, I really came away with a sense that this firm was being run very well.
And so in the end, for Masha and me, it was a very clear decision at the end of the day that this was the right place for us to continue and to build our practice.
DL: You mentioned AI earlier, and of course another very prominent Supreme Court and appellate practitioner, Neal Katyal, got in some hot water over some controversial comments he made about his use of Harvey in the tariffs case. I won’t ask you to opine on that, but I guess what I would ask you is this. Neal talked a great deal about how he was very effectively leveraging the power of AI. On the other hand, I spoke to another notable Supreme Court litigator, Jennifer Bennett of Gupta Wessler, who’s more on the plaintiffs’ side, but she said that given the nature of the work, she doesn’t find it very helpful. So where do you fall on this spectrum of Neal being a big cheerleader and advocate for AI and Jennifer being perhaps a skeptic?
KS: I think I probably fall somewhere in between. And both Neal and Jennifer are extraordinary advocates, and so it’s interesting to me that they have divergent views about this.
I think of AI first and foremost as a tool, and it’s an incredibly useful tool. We don’t use it yet to draft briefs. I don’t use it yet to tell me how I should answer questions at oral argument. But it can be incredibly helpful, sort of a steroidal version of the research tools that we used when we started out in practice, like Lexis and Westlaw, where we were crafting all these complicated Boolean searches. You can get an AI tool to do in two minutes what those tools could do after two or three hours of fruitless searching and rooting around. And it would be folly not to use those tools—but of course you have to use those tools responsibly. You have to be very careful to double-check the work, in the same way that we’ve always double-checked the work of humans working on cases. And you have to be very aware of the potential pitfalls.
And I think particularly for appellate advocacy, you have to remember that above all, particularly in oral argument, appellate advocacy is the art of humans persuading other humans. And you don’t do that just by making technically proficient arguments, and you don’t do that just by making the sorts of arguments you make to juries. You do that by connecting, by understanding the concerns that the very human judges or justices to whom you’re arguing have about your position and responding to them as best you can. And that’s the part of the job that I think will be the last part of the job that AI can successfully replicate. And it’s a very important part of the job, and I’d like to think that’s really what clients hire us for. It’s the human judgment about how to persuade other humans to agree with your position.
DL: I speak to law students and young lawyers, and I often get the question of, “What field of law can I go into where I’m least likely to be replaced by a robot?” And I actually tell them, and maybe I’m biased as a former litigator, but I tell them that litigation over transactional practice is actually probably pretty good, especially the type of litigation where you have to stand up and argue before a jury or a panel of judges, for no other reason than that juries and judges don’t want robots presenting the arguments. And the judges are in charge, of course—so as long as the judges don’t want the robots, we’re not going to have the robots. So do you think it’s probably true that the type of work you do is perhaps more “AI-proof” than some other areas?
KS: I think that’s probably true, at least until the judges themselves get replaced by robots, and at that point the robots will probably want robots arguing to them, but there would be all sorts of constitutional problems with that on the federal level, David. So I think at least for now, I think we’re good.
DL: Okay, good. Well, maybe we can safely make it to retirement before all the work for journalists and writers and Supreme Court and appellate advocates has been taken by robots. I don’t know about our kids; good luck to them.
But let me ask you this. We were talking about argument, and the Supreme Court is in a very interesting position right now. When I last interviewed you, we were talking about the pandemic format of argument, which had to accommodate certain realities, including the fact that you couldn’t really tell who was going to talk. And so the Court moved to this seriatim format, and now we have this sort of hybrid format where there’s a free-for-all upfront, and then a seriatim round of questioning where the justices go in order of seniority.
I actually really like this setup. In fact, I actually proposed it in an article, before it was adopted. But what are your thoughts on whether the format’s going to change? Because both Chief Justice Roberts and Justice Alito in the past few weeks have commented on how perhaps the arguments are a little bit too long now, and perhaps the marginal utility is decreasing at the tail end of these longer arguments. So I guess I have a two-part question. One, what do you predict the Court will do, and two, what would you want to see?
KS: So I love that it’s a two-part question because that’s like a question a justice would ask. And it’s funny, David, I remember the last time you interviewed me, it was right after one of these pandemic-era arguments. It was literally that afternoon, and it really was the pandemic that triggered the changes in the format of the argument, some of which have continued to this day.
So just for the benefit of the audience, as I think people are probably aware, the way that the Supreme Court currently works, to slightly oversimplify, is that each side gets 30 minutes, which was the way it was before the pandemic, but then at the end of the 30 minutes, the justices go one by one and can ask questions until each of them is done asking questions, and they go by order of seniority from the Chief Justice down to Justice Jackson, the most junior justice. And the result of that change in format has been that the oral arguments have gotten a lot longer, and it’s not at all unusual for an oral argument that started at 10:00 a.m. and previously would’ve been finished right on the dot of 11:00 to go past noon. I think my last argument went a little over two hours, and that’s not uncommon nowadays.
And so my personal view is that I’m happy to do the oral arguments however the justices would like. That having been said, I do think that there is a general sense that the oral arguments often, not always, go on for longer now than is perhaps useful. And I do think that there are certain weird consequences of that. One of them is that when the Court has two different cases in a day, the second case always seems to get short shrift because justices are human, too, and they get hungry. And by the time you get to 1:00 and no one’s had a lunch break, I think people are kind of ready to get out of the courtroom.
Another thing that I’ve observed is that it is usually the norm that the federal government will participate in a case as a friend of the court if it’s not a party to the case. And that means that it’s not uncommon to have two advocates on one side of the case and one advocate on the other. And it seems like when that happens, the time is inevitably split unevenly, favoring the side that has the government supporting it. And I think there’s a little bit of unfairness that comes with that as well.
And so I think those of us who speak in paragraphs rather than in glib half sentences like this current format, because it’s conducive to giving fuller answers, and hopefully that is helpful to the Court and to your client’s case. But at the same time, I recognize that there are countervailing considerations and that, again, the length of the oral arguments may not always be helpful to the Court. And so I know the Chief Justice recently gave a speech where he said that the Court was going to think about this a little bit more over the summer. It’ll be interesting to see what comes out of it—again, I’m happy to do whatever the Court thinks is most helpful—but I do think that the Court probably would be well served by perhaps at least tweaking the format, even if the Court does not go back to the prior format, which could sometimes be challenging, particularly in big cases where the justices have a lot of questions.
DL: And I also heard from some advocates that it was a little challenging for some of the justices, especially the ones who I guess were more junior, because they were worried that they weren’t going to be able to get the opportunity to lob in their question. And now the justices can kind of chill out a little bit more, because they know they’re going to get that time.
So I don’t know. I guess I’m trying to figure out what I would do if I were one of the justices. I don’t know that I want to cut out the seriatim round entirely, because of the benefit I just described. And if you were to just say, go back to really fixed time limits, like under Chief Justice Rehnquist, is that going to cut off somebody’s seriatim time? I don’t know. How long is that free-for-all right now?
KS: It really varies, but again, it’s not uncommon for the free-for-all to go for as long as the original part of the argument itself. I think some advocates have speculated that the Court might have informal limitations on each justice, like three minutes per justice. And nobody knows that for certain, but it does seem as if the justices sometimes suggest that their time is up or otherwise that they’re somehow limited. I could see the Court perhaps tightening those limits a little bit, though sometimes it’s actually helpful when a particular justice gets on a roll and is getting helpful answers; I don’t know that you want to artificially curtail that either. So I’m glad it’s not my problem, because I think it’s not an easy question to figure out what the optimal format is. And I suspect the justices themselves have different views about that.
DL: What about this? What if we get rid of that little minute or two at the front where you get to give uninterrupted remarks? Come on, we all know what this case is about; let’s just cut to it. What if you cut that part off, had a time certain for the free-for-all, and then also had a little time limit on each justice that was actually public and transparent and that the justices knew, too?
KS: What’s funny about the two minutes at the beginning, David, is that that actually came first. The Court instituted that right before the pandemic and retained it after the pandemic. I don’t know how helpful that is to the Court. As an advocate, I actually find it very helpful because after I’ve gone through the preparation process, sometimes I think about the case in a slightly different way, and I try to capture that in the introduction to the argument. And so if someone is listening closely to that introduction, they might perceive the fact that I’m emphasizing some points slightly differently.
And so I think at least for the advocate, it’s a useful tool, but ultimately it’s for the Court to decide whether it’s helpful to them. I do think that often you hear justices referring back to the introduction during the oral argument, which to me is at least some evidence that they are paying attention to it and interested in what the advocates have to say.
DL: You’ve kind of brought me around. I guess I ascribe more utility to that than I used to.
Let me ask you one last question before we go to the speed round. We are recording this now on Thursday, June 4, and we are still waiting for some of the most high-profile rulings from the Supreme Court. The ones that came down today—no offense to the advocates and parties to them—were not so exciting to those of us who are just members of the chattering class or the punditocracy. But let me ask you, based on what we’ve seen so far, do you have any big-picture thoughts on themes that are emerging from the current Court? It’s been stable in composition for a little while now, since the arrival of Justice Jackson. There’s been a lot of talk over the emergency/shadow/interim docket.
So again, big picture, the Supreme Court: where is it now, and where is it going?
KS: Well, we’ll have a better sense of that about a month from now, David, because as you say, we haven’t really had most of the significant decisions of the Term—but there’s no doubt that this is the Term where a number of the major pieces of litigation involving the administration have now finally come to the Court, for the most part, on the merits.
We had a lot of action on the so-called emergency docket in the first year of the president’s term. But here we are in the second year, and now you have all of these major issues, the tariffs case (which has of course already been decided), the cases involving the presidential removal power (both the case involving the FTC and the case involving the Federal Reserve), and the case concerning birthright citizenship, and a number of other interesting second-order cases involving administration initiatives. And it’ll be interesting to see where the dust settles in all of those cases, to see how many of those cases the administration wins and how many of them the administration loses.
And I think if the administration loses at least some of those cases, the interesting question will be, where do the justices break down? And I think in particular on a Court with six Republican appointees that is somewhat more conservative than the Court that you and I grew up with, David, as baby associates, I think it is clear that there are still some meaningful jurisprudential disagreements among those six justices. Your colleague Sarah Isgur has written a whole book about that and has talked a lot about that on Advisory Opinions. And I think that this year is going to provide some pretty significant evidence of that, and how that affects the narrative around the Court and how the Court is perceived is going to be very interesting. I think that there was this narrative that the Court was being deferential to the current administration, and that narrative may well change if the current administration loses some of these big cases.
DL: And I would venture that it’s already changing because of the tariffs case. That was a signature policy initiative of Trump, and we’ll see what happens in the birthright case, but I agree with you, this will be a very revealing next few weeks.
So turning to the speed round, these are four questions, and they are the same for all my guests. And my first question is, what do you like the least about the law? And this can either be the practice of law or law as an abstract system.
KS: I think the amount of time I spend dealing with administration. I wish I had more time to prepare for arguments and less time that I spend reviewing bills.
DL: At Paul Weiss, you were both the head of the D.C. office and a co-chair of litigation. I believe at Davis Polk, you’re head of the appellate practice, right?
KS: I am, but that’s easy because until recently the appellate practice was just Masha and me, and she’s very easy to administer. No, I did have some really significant administrative responsibilities when I was at Paul Weiss; I enjoyed them when I had them, but I’m very glad to be focusing now on practicing law. And I hasten to add that the reality is that if anything, Masha is probably administering me rather than vice versa, even though I have the title. She’s much better at that stuff than I am.
DL: Fair enough. My second question is, what would you be if you were not a lawyer?
KS: Well, as I said earlier, I probably would be a journalist. And in my younger days, I would’ve loved to have been a professional athlete, but it became pretty clear that that was not going to happen.
DL: My third question is, how much sleep do you get each night?
KS: So I knew you were going to ask that question. I would say if I’m being honest, about seven hours. I am an early bird. I tend to be up by about 5:45, and I tend to be at the office by about 7:00. If I’m not in bed by 11:00, something has gone wrong.
DL: Fair enough. I always like hearing a number above six from very successful lawyers and other figures in the legal profession, so I’m glad to hear seven. My last question is, any final words of wisdom, such as career advice or life advice, for my listeners?
KS: I gave a graduation speech a few years ago where I said that a career is like a climbing wall. Sometimes you have to go sideways or even down to get to where you want to go. And I think that’s really important advice.
My oldest is heading off to college next fall, and I think a lot about this because I think that, for people in our kids’ generation, there’s this tremendous temptation to think that a career has to be linear and that there are just natural steps, and that if you take each of those steps, you’ll rise to the top of whatever profession you’re in. And I just think that the reality is that there are very few people for whom that is actually true. And if you talk to even the most successful people in our profession, chances are that they’ve had setbacks, things that have gone wrong in the course of their career. They’ve made decisions that may not have been obvious career decisions that ended up working out really well for them.
And I think that that is really important advice, particularly for people who are getting started—that it’s okay to make mistakes and to perhaps do something just because it’s interesting, not because it’s the next step on the career ladder. I actually think, again, that when you talk to really successful people, at some point along the way, they can point to something that’s in that category.
DL: Well, I’m very glad to hear you say that, because I suspect that you have not been denied any opportunity since the time that we didn’t hire you for that tutor job.
KS: That’s completely false, but that’s a subject for another episode. We could do the episode of “All of Kannon’s Professional Failures” for our next episode together.
DL: I think that would be a very short episode. Kannon, thank you so much for joining me; it has been a pleasure.
KS: It’s a great pleasure, David. Thanks for having me.
DL: Thanks so much to Kannon for joining me, and congratulations to him on his move to Davis Polk.
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