From BigLaw to Boutiques: David Lat on Trump, VanDyke, and the Art of Oral Argument

Jeff Lewis
Welcome everyone. I am Jeff Lewis.

Tim Kowal
And I'm Tim Kowal. Both Jeff and I are certified appellate specialists, and as uncertified podcast hosts, we try to bring our audience of trial and appellate attorneys some legal news and perspectives they can use in their practice. As always, if you find this podcast helpful, please recommend it to a colleague.

Jeff Lewis
Yeah, if you find it unhelpful, send it to your opposing counsel.

Tim Kowal
All right, Jeff, today we're excited to bring David Lat to the show today. David is a lawyer turned legal journalist and one of the most influential voices covering the legal profession today. He founded Above the Law, one of the nation's largest legal news websites, and now publishes Original Jurisdiction, a Substack newsletter with over 22,000 subscribers and a companion podcast. Original Jurisdiction covers two main beats, big law and the federal courts, especially the Supreme Court. David is a graduate of Harvard College and Yale Law School. He previously clerked on the Ninth Circuit. He practiced at Wachtell Lipton and served as a federal prosecutor in New Jersey. He's also a Bloomberg Law columnist and the author of the novel Supreme Ambitions about a Young Lawyer Navigating the Federal Clerkship World. David also received the ABA Journal's Legal Rebels Award and the American Lawyers Top 50 Big Law Innovators Honor. And of particular interest to our California attorney audience, before David became a legal commentator, he clerked for Judge O'Scannlain on the Ninth Circuit. So he has seen oral arguments from the other side of the bench. And we'll be talking about David's oral argument tips in our conversation today. Obviously, the Ninth Circuit is a regular beat of many of our listeners. David earlier this year, published a piece that has been circulating in appellate circles, Three Tips for Appellate Advocates from Paul Clement, analyzing Clement's oral argument in Trump v. Cook and drawing practical lessons that our listeners can use. He's also the person who wrote the definitive deep dive on Judge VanDyke's now infamous Ninth Circuit dissent, which Jeff and I talked about in the last episode. That's the one that opened with the phrase that required the parental guidance warning before we discussed it. And we'll talk about what that dissental and the related fallout tells us about the state of the judiciary recently and today we're going to cover two big themes the movers and shakers reshaping the legal landscape now and the craft of oral argument what separates a competent performance from a master class and how the lessons from elite Supreme Court advocacy translate to California State Court of Appeal and the Ninth Circuit David Lat welcome to the podcast

David Lat
Thanks for having me.

Tim Kowal
You and I have crossed paths a couple of times at legal events. In fact, at Federalist Society events where you've been a speaker, actually for a long time, I assumed that you were right of center because no respectable left of center person would ever sit within 100 feet of a Federalist Society event. You are...

Jeff Lewis
Well, let's be clear, we're not invited, Tim. The people on the left are not invited, but go ahead.

David Lat
Hehehe

Tim Kowal
Well, that's not true, Jeff. We've talked about those who are invited and allegedly sandbagged at events. So David, I think you're a true legal journalist, shooting it down the middle, because I honestly can't tell which side you fall on issues, even when we're talking about hot-button issues where there are obvious differences of opinion, and everyone has an opinion. I never see you grimacing while you try to just give us the facts or tell us the facts of the case through gritted teeth. You always play it straight. You always leave whatever your opinions at the wayside. So I appreciate that about your legal journalism. And maybe you can tell us a little bit about your path to becoming a legal journalist and whether that was always your destination, or did you stumble upon it by accident?

David Lat
More the latter, stumbling upon it by accident. So I was an assistant US attorney in New Jersey, as you mentioned earlier. And at the time, I thought I wanted to try something on the side. I was actually doing appeals. I was an appellate at the US, so I was arguing before the Third Circuit. But I wanted to do some writing that did not involve Bluebook citations. And so I came up with the idea of doing a blog, which was a popular thing to do back in 2004. So this is more than 20 years ago, and it was called Underneath Their Robes, News, Gossip, and Colorful Commentary about the Federal Judiciary. So I was doing this under a pseudonym for a while, for, I don't know, a year and a half, two years, and I'm giving you the abridged version. Eventually, I revealed myself as the author of this, and shortly thereafter left the practice of law. and eventually moved into journalism and blogging full-time. I launched Above the Law in August of 2006. So it turns 20 actually later this year. And then a couple of years ago, actually 2019 or so, I left Above the Law to try something different. I actually worked as a legal recruiter for about two years. And then the pandemic came, and that kind of threw things into relief. And I realized that while I enjoyed recruiting, much as I enjoyed practice, what I really loved doing was the writing and the journalism. So that's when I started Original Jurisdiction, my Substack newsletter. And a little while into that, I started a podcast. And so that's now what I do. I have this newsletter, and I have a podcast. And as you mentioned, I do a column for Bloomberg Law as well. So I am now fully over to the journalism and commentary side.

Tim Kowal
Tell us a little bit about what you have seen from your perspective as a blogger, just as a, I did some blogging in around that time, not anything really related to the law, but blogs fell to the wayside, I think more or less in line with the advent of Twitter and Facebook and all the microblogging and the heyday of blogs fell out of fashion. Can you tell us a little bit about... You know that falling away. Did you experience a falling away, and did the Substack step into the breach and replace that? because that seems to be the place to go now for freelance writers

David Lat
Yeah, so in some ways, I think Substack has replaced blogging, and a lot of the bloggers from, I guess, blogging 1.0 are now very active on Substack, including, for example, Andrew Sullivan. There are a lot of folks who are in that first wave of blogging who have now moved to Substack and similar platforms. A lot of this has to do with the economics of it, actually. I think Substack has allowed individual writers, individual voices, to make a living from their content. Before, you needed to be part of a larger operation. And so when I started Above the Law, actually, on behalf of a company called Breaking Media, which publishes a couple of different industry-focused websites, I hooked up with them because they had the expertise in monetizing content and selling ads. Whereas now, you don't really need to sell ads. You can just have a much smaller number of dedicated subscribers who are willing to pay a few dollars a month or a little bit more per year to support your writing. And so that's the model. And I think it's been a very good model. There are some downsides to it, I think. Certainly, individual journalists on Substack or other platforms don't have the ability to do some kind of very in-depth enterprise or accountability journalism that larger media organizations can do. But on the other hand, it really has been a lifeline for individual writers who now don't have to depend on some larger news organization and don't have to worry about getting fired or canceled if they write something that does not meet with their employer's satisfaction. So I think it's really been, overall, a very good thing for the media landscape because this industry has been a challenging one.

Tim Kowal
So, from the perspective of someone who has been following the legal industry and the courts for 20-plus years, let's talk about a few of the recent stories that affect the judiciary and big law, and then maybe a transition or a possible movement of some former big law attorneys to boutique firms. We'll ask you if that is a trend. But let's start with that. The recent news out of the Ninth Circuit and Judge VanDyke's dissental in the Olympus Spa case. As I mentioned, Jeff and I covered that in a recent podcast, but that's the case where the court denied rehearing en banc of a case that I guess it dismissed the claim by the Olympus Spa owners. And Judge VanDyke opened his dissent, saying, and this is the parental guidance warning, this is a case about swinging dicks. And David wrote a delightful headline. I think it was called putting the dick in dicta. Dicta. Um, that's one of those uh, you know, I rehearsed that with uh, you know, red leather yellow leather I couldn't uh, but I couldn't get it up right. Um 29 colleagues rebuked the dissent. Judge McKeown uh led a statement joined by 28 judges, calling it quote vulgar bar room talk judges Owens and Forrest, uh Trump appointees, wrote simply we are better than this and David, in your piece, you explored what the episode says about the judiciary in 2026. Can you kind of give us a reprise of your piece, your take on that episode?

David Lat
Yeah, so it's interesting. think the Ninth Circuit, going back to when I clerked there, has always been a court with big personalities. It's a big court. has, I think, currently active in senior judges of around 50 or so, around 30 of them active. so it's also the dynamic on the court is different than a lot of other smaller courts. You have judges who, maybe have chambers very far away from each other. It includes Alaska and Hawaii in its jurisdiction. And so the judges may not see each other as frequently. A lot of that communication happens over email. I think sometimes tempers flare. Overall, I think it is a pretty collegial court, but it may not be as collegial as a court like the First Circuit, which has six active judges. And so sometimes there is some friction. So as you mentioned, Judge VanDyke wrote this very controversial dissental and a total of 27 judges joined the McKeown statement that criticized it. And then two additional judges, Judge Owens, who's an Obama appointee and Judge Forrest, who's a Trump one appointee, they joined that much shorter statement that you read. And I think it reflects a couple of things. mean, certainly it shows that the judiciary, like American society writ large, is no stranger to polarization. This case, is a very divisive case. involves an all-woman nude spa that does not want to admit a pre-operative transgender woman, an individual with male private parts, I guess you could say. And so, of course, anything related to transgender rights or individuals is certainly a very hot-button issue. So I think it definitely shows how the cultural wars, so to speak, have not spared the courts. And then I think also it's very interesting. There was a piece that I mentioned in one of my discussions on original jurisdiction by Mike Fragoso, who wrote a piece for the National Review about this. And he talked about the postmodern jurisprudence of Lawrence VanDyke. And I agree with a lot of what Mike is saying in that piece, because he's essentially saying, look, yes, sure, Judge VanDyke has conventional, traditional legal reasoning in his opinions a lot of what he's doing is actually calling into question the enterprise of judging as it is practiced on the Ninth Circuit. So he does a lot of things that are unorthodox or outside of the box, but they are in service of this kind of meta commentary on what his colleagues are up to because he's a very conservative judge. He's been mentioned as a possible Supreme Court nominee under Trump. And he still views the Ninth Circuit, which I think has evolved a lot over the years, but he still views the Ninth Circuit as unacceptably liberal, progressive, left-leaning, what have you. And so a lot of the things he does are aimed at calling out what he views as judges imposing their policy preferences on the law. So, for example, he did that infamous YouTube dissent in a gun case, which I believe he covered. He did this latest dissental, which you covered about the swinging parts of the anatomy. He's done a lot of other things, which have definitely rubbed his colleagues the wrong way. But as he said in a recent speech to the Federalist Society Student Symposium, he believes that they're the ones who owe an apology because they are imposing their preferences on the law. And he had some humorous comment where he said, well, I'll offer you a deal. I'll stop engaging in these aggressive maneuvers if you start following the law. So that's his perspective. I personally am not a fan of his particular approach, but I understand what he's trying to do.

Tim Kowal
Yeah, I guess in a sense he's saying, I'm not going to play by the Queensbury rules anymore if we can't even agree on some certain basics, I guess, in his mind, then I'm going to have to take this up a notch. And the other example that Jeff and I have talked about before was his panel majority decision in the Second Amendment case to which he concurred, writing the first draft of the en banc decision overturning his own decision. So yeah, like you say, he always seems to be looking for unorthodox ways to get attention. But I guess the question is, is he trying to get his colleagues' attention, or is he getting the public's attention? That was kind of what Jeff and I tentatively landed on when talking about the Olympus Spa case, is that he's writing to the public to try to get the hackles up of some members of the public about some of these hot-button culture war-type issues. But I guess the next question, assuming that thesis is correct, maybe the next question would be to what end? It's certainly going to create some consternation among the public against the judiciary, maybe lower the public's esteem about the judiciary. So to what end? And that I don't know I guess you would have to interview Judge VanDyke about that.

David Lat
Yeah, I think that's my concern with what he's trying to do if in fact this is what he's trying to do. I think it does lower the public regard for the judiciary. And some of that will not necessarily run down to the benefit of conservatives because the court that most Americans think of when they think of these types of things is the Supreme Court, which is currently dominated by a six-to-three conservative super majority. And so, if you are in general causing Americans to think of judges as politicians in robes, that is perhaps not a good thing for the judiciary. But again, I always try to see multiple sides of the argument. And I think what Judge VanDyke is saying is, look, they're already politicians in robes, some of my colleagues. And I'm just calling them out because that ship has sailed or that train has left the station, or whatever metaphor you want to use. yeah, I guess, you know, that's kind of, that's kind of where we are. you know, I, I guess you could say it's interesting to have at least one judge VanDyke around. Mean, it's certainly more fodder for those of us who are podcasters and journalists. I definitely would not want to bench entirely, of Judges VanDykes. But, you know, he does raise some issues that are worth discussing. Even though on balance, I think sometimes maybe this approach brings more heat than light.

Tim Kowal
Well, and there's a theory that maybe it's not just a theory, which was Justice Scalia. Maybe I can't remember if it was just a theory that he had no interest in becoming Chief Justice because he would rather speak his mind in dissents rather than try to curry favor and curry consensus, as just Chief Justice Roberts has proved effective at doing. But sometimes at the sake of a clear rule, sometimes that you come out with a unanimity or or occurring Winning a couple of additional votes at the expense of some doctrinal muddiness and and just a Scalia Say what you will about him would not have I think put a high premium on doctrinal clarity in his opinions and sometimes that meant Speaking them in an acerbic manner, but you always knew where he stood. And so, like you say, it's sometimes nice to have someone like a Justice Scalia or a Judge VanDyke around to speak his mind about what's going on from his point of view. Maybe in some sense, speaking out of school. But David, you being a legal journalist, it's interesting that your opinion on it is you're not a fan, although certainly it's going to drive more traffic to your Substack and to your podcast to hear what the latest is out of Judge VanDyke.

David Lat
Yeah, you know, it's funny. A lot of what's going on generally with the Trump administration has been very good for legal journalists in terms of our audience or our following. But I have to say, there's also a level at which it's just exhausting. It's very easy to get burned out just covering the torrent of news. And so many stories that start off as merely Trump administration stories eventually turn into legal stories because litigation is filed, and many times they turn into appellate stories specifically because things get appealed, whether on an interim or emergency basis or after a final judgment. So there's just a lot. I would take the trade-off in terms of traffic and subscribers to have a little less to cover. We're not lawyers, but we journalists like to have work-life balance too. But it definitely has been a... a busy time.

Tim Kowal
Okay, so from the bench to the bar, let's talk about the Trump versus the big law executive orders. Now this was all the talk last year. Things have settled down a little bit since then, but David, could you give us a little bit of a recap of where things started and how they're going now? I mean, this was back in early 2025. The Trump administration had targeted certain law firms, big law firms like Perkins Coie and Wilmer Hale and others with executive orders revoking security clearances restricting access to government buildings And the many of the firms fought back in court so far successfully judge Richard Leon of the DC District Court struck down the Wilmer Hale order And David you had predicted that the Supreme Court would decline to take these cases Do you still hold that hold of that prediction?

David Lat
Yes, so right now, after the administration lost all four of these cases in the US District Court for the District of Columbia before four different judges, the government took an appeal to the DC Circuit. The cases were consolidated. And then we had this very bizarre turn where, on Monday, a little while ago, the government moved to dismiss the four appeals. And then on Tuesday, they moved to withdraw. Their motion to dismiss the appeals, which was granted. And it made sense that it was granted because nothing had happened in reliance on this motion to withdraw the appeals. But we are now going to have this litigation. The government filed its opening brief. The law firms' briefs, the cases are consolidated, and each firm gets to file its own brief. The firms argued for that because they said, look, we all have somewhat different circumstances, which is fair. Trump went after the firms for different reasons, for example. So we're going to see how this plays out. It's funny. I suspect that the government, it loses in the DC Circuit, which I predict it will, it will seek Supreme Court review. I wasn't necessarily sure of that before. But apparently, what happened in this situation with the DC Circuit, according to reporting by various outlets, including The Wall Street Journal and CNN, is that the government decided to, the Justice Department decided to withdraw these appeals. And then the news made its way up the food chain, the chain of command, and Trump himself found out about it. And in the Oval Office complained about this, even though the DOJ folks claimed that the White House was informed of the plan to drop the appeals. But Trump said something like, I didn't sign off on this, and he wasn't happy about it. And so, lo and behold, the very next day, the government moves to continue to prosecute these appeals. And so here we are. I think they're going to lose in the DC circuit. Aside from what I think are there, I think the arguments in favor of these orders are fairly weak. But even if you just want to take a more sort of legal realist perspective on it, the DC circuit is composed largely of democratic appointees. And I just don't see the administration prevailing here. Guess maybe it'll depend on the panel. But if somehow the administration won in the panel. I think it would get reheard en banc. And then I think the Supreme Court's not going to want to take this. There's no circuit split on it because these cases all came from DC. So there won't be a circuit split. I think, in my opinion, the issues are squarely controlled by existing First Amendment law. And it's not technically moot. But as a practical matter, it's politically moot in the sense that Trump doesn't seem to be doing these orders anymore. So why should the Supreme Court, which I think would have to rule against him, unnecessarily antagonize him if this is no longer a major initiative of his he's focused on other things he's focused on Reimposing tariffs. He's focused on a war with Iran. He has other fish to fry, and so I think the law firms are not really on his radar, at least right now. So why would the Supreme Court want to spend? Political capital, if you will, on something that is probably now not going to have much practical effect anyway.

Jeff Lewis
Yeah, and a little more broadly, why would the Supreme Court step in given that no future president of either party is likely to target law firms with executive orders in the future, I would suspect. I tend to agree with you.

David Lat
I agree with you. Yes, I agree with you, Jeff, because look, a lot of people say, well, the big question about the Trump administration is what norms are going to bounce back and what norms are permanently eviscerated? Look, I do think that he has definitely changed some things. And I think that certainly civil discourse is not going to be the same after him, regardless of whether the Democrats retake. Congress or retake the White House. But I agree with you. I think that these laws from executive orders are not something the Democrats are going to try to emulate. I don't think we're going to see orders against Jones Day or Consovoy McCarthy or Cooper & Kirk or any of the conservative law firms that often oppose Democratic administrations. So I think those particular norms will bounce back. But some other things, I think, will not.

Tim Kowal
Well, given that, do you think that there is going to be any lasting effect of these executive orders? I mean, we would hope that there would not be, but on the other hand, I guess that would be, this president does not like to take the L on anything. And if there's going to be no lasting effect, do we have to hand him the L on this one, even though the courts are not going to hand him an official judicial L?

David Lat
Well, you know, what I would say here actually, and I've written this to some extent about big law and the Trump orders, is you can't really say that the, I don't think you can really say that the Trump administration is taking an L here. I think there's actually an interesting argument that the administration is coming out ahead here, even with the court losses. And one reason for that is the chilling effect that I described earlier, where you've seen big law firms dramatically curtail their challenges to Trump policies. But another reason is that some of the big firms that did get these orders settled. And by settling, they essentially gave the administration some of what it wanted in terms of the hiring and pro bono commitments. So while I would say the courts did rule against the administration, at a practical level, the administration may have gotten more than it bargained for in terms of the impact on big law's behavior. And I think it's going to be studied in business schools and law schools for years, this whole episode.

Tim Kowal
Yeah. So on the legal front, nominally a loss, but on the practical front, at least arguably a W for what Trump was trying to do. Yeah, it does seem right that these big law EOs were idiosyncratically a Donald Trump thing. Future presidents are not likely to try to do the same thing because it wasn't necessarily a partisan thing. It was a personal thing Okay, let's, and now the last kind of legal trend we'll talk about before jumping into oral argument tips, Jack Smith's new boutique law firm. He launched a litigation boutique with three former prosecutors. David, on your podcast interview recently, you discussed the detail that they had gone to Costco to buy paper towels, a very... vivid real-life incident where you wouldn't think of a former special prosecutor going to Costco to buy toiletries and paper towels and things, but that's the reality of moving from big law to starting your own shop. So I wanted to ask you if you think that we're going to see a broader pattern of government attorneys going small rather than going to big law, and is that a function of anything ideological or these economic and technological advancements that are creating these new opportunities?

David Lat
I think all of the above. I think one thing that is certainly making the boutique model more viable is AI. Because if you look at the traditional advantage of the big law firm, it's resources. And we've talked about this. The giant army of associates that you can deploy. But if AI can do the work of five associates, well, then suddenly the boutique becomes much more attractive. And I think there's also the reputational factor. I mean, Jack Smith is someone who already has his bona fides established. And I think you're going to see more people like Jack Smith. People who have proven themselves, either at big law or at the government or wherever, who are then going to go off and do their own thing. Because the tools are there to support them now in a way that they weren't before.

Tim Kowal
On the other hand, the legal profession is still a very conservative and traditional profession. And I think there's still a lot of premium put on the big firm imprimatur, especially at the outset of one's career. And so I don't think we're going to see a wholesale shift to boutiques. But I do think there's going to be more of a bifurcation, where you have the established, well-known stars going boutique, and then the up-and-comers still going to big law to build their credentials. What do you think?

David Lat
Yeah, so I think that generally in our economy, what you've seen is the emergence of a so-called star system. The rewards in different professions go more and more to the top performers. And I think law is seeing that now. Where the really top performers can go off and do their own thing because they have the client base and the reputation. And the others are kind of treading water or just trying to make partner at whatever firm they're at. And I think that's kind of the dynamic that you're describing. And look, for those who aren't already stars, what do you do? I think the answer in part is, like I said, developing your own niche or becoming a known quantity in a particular area. And I think that's how boutiques have traditionally operated. You become the go-to person for a particular kind of work, and then you can command the premium that goes with that.

Jeff Lewis
And David, you mentioned the role of tech in the making it a little easier to develop and launch a boutique. And I'm going to ask specifically about AI. You know, AI has gotten a lot of buzz over the last couple of years in the legal profession. Arguably too much buzz. But let's talk about what AI can and cannot do in the context of the legal profession. And especially are there opportunities or challenges that come with integrating AI tools into a law practice?

David Lat
Well, just to start with the obvious, the challenge is I've written about numerous cases where lawyers relied excessively on AI, for example, relying on it to draft a brief without checking the validity or the correctness of the citations. And it turned out the cases were non-existent or so-called hallucinated, and then they got in trouble. And there is a case, I believe you've discussed before, involving a California appellate court that is considering sanctions against a lawyer who got into trouble for that. So the obvious challenges are just misusing it. But I don't even know if that's so much a challenge in the sense that lawyers have always had tools, whether the tool is email or Westlaw, Lexis, or Bloomberg Law, or a fax machine back in the day, or what have you. And they're just tools. The tools are not bad or good necessarily. It's how you use them and whether you use them responsibly. So AI is just a tool that you need to use responsibly, just like any other tool, and so if lawyers use it irresponsibly, well, that's kind of on the lawyers. ChatGPT didn't file the brief itself. A human was still on the last line of defense there. So I think the challenges for AI are just, well, the challenge of not using hallucinated cases really shouldn't be a challenge. Now, here's a challenge, I guess. And this goes to sort of your next question, Jeff, about just the capabilities. I think the challenge is knowing what it is good for and what it is not good for? Because the technology is not completely there yet on all things. And so for example, I ask lawyers often, practicing litigators, what do you use AI for and where is it not all there yet? And so for example, things that don't involve filing final work product with a court or things that don't involve reliance on citation of law, those things AI is better at or is safer to use. So for example, a lot of lawyers, when they're preparing for an appellate argument, will use AI to come up with argument questions for a moot. What if you, you know, they might feed the briefs in, feed the relevant cases and say, what can I expect to be asked at oral argument? And it'll toss out some questions. And some of the questions might be very good questions and some of the questions might be duds, but you're not going to be harmed by the existence of the dud. Just don't bother thinking about it. Focus your attention on the questions you think are likely to be asked at oral arguments. So that's a good use of AI. In terms of drafting a brief from scratch, I think it is not there yet. At least a lot of the programs are not there yet. Maybe the lawyers I talked to are not using the right programs, or maybe they're not prompting them correctly. But I think drafting from scratch is still a bit of a challenge. But it can be used for other things. Many people I talk to say it does perfectly good summaries of cases. You find the case, it does exist. It is a valid case. You feed it in. I've even had you know, had lawyers tell me it can do a pretty good job of identifying in a circuit court opinion potential issues that you might want to seek rehearing en banc or cert on. One lawyer I really respect said, yeah, it did a pretty passable job. You know, not, you know, maybe not perfect necessarily, and maybe not as good as what that prominent partner would have done himself, but certainly on the level of what a smart associate would be able to produce. So I think the challenge is knowing what it's good at. Because look, it is good at a lot of things. Let's not deny that. I think there are a lot of opportunities here for lawyers who are smart about it and use AI responsibly.

Jeff Lewis
You know, I want to follow up on the lasting impact of the BigLaw executive orders. And I've been following this just because our clients often end up as opposing parties of BigLaw firms or sometimes co-counseling or working alongside BigLaw firms. What is the lasting impact of these executive orders? I mean, are BigLaw firms going to be more reticent to file lawsuits against the Trump administration in the future? What do you see as the lasting impact?

David Lat
Yeah, so I think the lasting impact is probably considerable. And here's the way that I think about this. So I think of the executive orders essentially as a carrot and stick regime to manage big law. On the one hand, you know, you had these four firms that fought back, including Perkins Coie, WilmerHale, Jenner & Block, and Susman Godfrey. And they were successful. They won in the district courts. And as I said, I expect them to ultimately prevail on appeal, although it will take time. And then nine of the firms that received these orders settled. So this is another big chunk of the firms that received these orders. And by settling, they agreed to, for example, commit to political non-discrimination in their hiring and pro bono activities. And some of them committed to a combined total of I think it was around $940 million in pro bono services and to do these services in connection with causes that the Trump administration favors. And so here's the thing that I think some people get wrong. I've seen some people on social media say, well, Trump lost all of these cases in the district courts. So it was a loss for Trump. And I think that's a very wrong way to look at it. Actually, Trump, I think, will be seen in retrospect as mostly winning this campaign against BigLaw because look, the four firms that fought, they got to keep the status quo. They were vindicated in court. But they didn't really win anything beyond keeping the status quo. And there were nine firms that capitulated and essentially agreed to basically some things that some people would say are significant concessions. And then there's the chilling effect that I think many commentators have pointed to. For example, The Washington Post did a story a little while ago looking at large law firms and their filing of lawsuits against the Trump administration and comparing it to the first term. And these firms have dramatically curtailed their challenges to Trump policies, which in turn makes it harder for these policies to be challenged, which makes it more likely these policies stick. So I think that's the lasting impact. This effort to go after BigLaw has not necessarily been successful in court, but it has been successful in achieving its actual objective.

Jeff Lewis
Yeah. And are boutique law firms filling the void? And is there a trend towards boutique law firms, former BigLaw partners going off to boutiques? And if so, is that something that is going to, is this a permanent change in the legal profession?

David Lat
Yeah, so in terms of boutiques filling the void, I think the answer is yes, at least partially. And I think there are a number of boutiques that have stepped up. And I'm sure you, you know, in your own practice, you might actually be able to speak to this better than I can. But there are a number of, some small firms, some individual practitioners, some civil rights groups, who have stepped up to kind of fill the gap left by big law. But I think the challenge is, you know, some of the cases that the Trump administration is involved in are just ginormous. I mean, they involve complex issues, lots of people, lots of documents. And you need a larger organization to be able to handle some of these things. And boutiques, by definition, may not necessarily have the resources and wherewithal. However, I think one thing that boutiques have going for them here is AI because AI is being used more and more to do work that associates used to do. And so I think this is actually an area where boutiques have perhaps made the greatest inroads because AI allows them to do work that previously would have required a large army of associates. And so that's the way in which I think boutiques have been able to kind of keep up.

Tim Kowal
Well, so there's one example of this is the Jack Smith boutique, which when it was launched, was described by one of the partners as they, it was so new that they had to do a run to Costco to buy paper towels for the office. And so this is a brand new boutique firm. And this is a firm that is actually handling some very high-profile matter. So it's a good example of what can be done. But I agree with you, David, that there's a lot that AI cannot do. Boutique boutiques are already competing effectively in the appellate space at least. And we've seen a lot of boutiques that do very sophisticated work on appeal without having the resources of a big law firm. but AI doesn't replace the institutional name of a big law firm. So if you're a young associate coming out of a top-flight law school, and you know, you need to make your, you need to build your reputation, you've got to prove your bonafides before you join a boutique or start one. If you're coming out of law school and you immediately try to join a boutique or start one, you're not going to have the name recognition. And a lot of litigation, especially early in someone's career, has a lot to do with name recognition and imprimatur and the firm's reputation. And boutiques, especially the new ones, haven't built that up yet. So there's a role for both. But I do think there's a trend toward boutiques and away from BigLaw.

David Lat
I definitely think there's a trend toward boutiques. And I think you're right that the institutional brand of a large firm still matters, especially early on. And I think to the extent the boutique trend works, it often involves lawyers who've already done time at BigLaw. They've built their reputation, they've built their client book, and then they go off and do their own thing. And then additionally, there are these co-counseling arrangements where smaller boutiques that might be handling some of these high-profile matters, they might bring in one of these, these large firms to maybe handle some of the discovery or the document-intensive work. And so this kind of hybrid model is becoming more popular.

Tim Kowal
Yeah, that's a good, and that's actually one of the things that we do, that's kind of our model in our firm. We do the appellate work and we have the, we handle the appellate strategy, but we bring in, we work alongside trial firms who handle the trial work. And so it's a partnership. And we also work with clients who have the in-house counsel and the in-house counsel handles the trial work and the the day-to-day management of the matter, and we handle the appellate strategy. And it's a partnership and I think it works well. And I think there's going to be more of this.

David Lat
And I think especially when it comes to appeals, the appellate boutique can really do everything you need for the appeal, because appeals are much less resource-intensive than trials. You know, appeals are mostly written work and then oral argument. And so, and there's much less in the way of, you know, large document reviews and that sort of thing. And so I think that for appellate work, boutiques are very well-suited.

Tim Kowal
Okay, and and tell me about, let's see, on the topic of AI, let's probe that a little bit. Let's be honest. We've been doing a lot of hand waving about AI, but if you actually look at the realities of it, AI doesn't actually do that well in legal research and legal writing. In fact, the studies show that AI still hallucinates and makes errors. And AI lawyers have been caught embarrassingly submitting false citations in pleadings and briefs. And the courts have caught this and they've been sanctioned or at least embarrassed. And so the early enthusiasm for AI in legal practice is now being tempered by the reality of it. And I think for sophisticated practitioners, you still need a human, a credentialed lawyer to check all of the AI's work to make sure that the AI hasn't gone off the rails. And then there's also the inherently human nature of legal work. You know, persuading a judge or persuading a jury, that's a fundamentally human endeavor. And AI may be able to get the legal research right and even might be able to draft the words of a brief, but there's a human quality of persuasion that AI cannot replace. So I think there's going to be continued enthusiasm for AI in legal practice, and there is going to be progress, but it's going to be, the progress is going to be slower than some of the boosters of AI are predicting.

David Lat
Yeah, I think that's probably right, Tim. I think AI is going to keep improving. It's getting better all the time. But there are going to be some things about law, especially the relational aspects of it, the oral argument, the client relations, the advocacy before human beings, that AI is just not going to be able to replace. And I think that's actually good news for lawyers. I think there's some anxiety among lawyers that AI is going to take their jobs, and I think certainly it's going to change the nature of the work. But there are going to be things that human lawyers do that AI simply can't replicate. And oral argument is one of them. And I do think that oral argument is one area where the human element just cannot be replicated by AI. Can you imagine sending in a ChatGPT or whatever it might be to do oral argument? It's just not going to happen anytime soon.

Tim Kowal
Yeah, I think there is going to be a lot of experimentation incumbent on us attorneys to keep trying new things with AI. And there's a lot of different foundation platforms, each of which is good at something different. And if it's not good at something today, try it next month. It might have gotten heads and shoulders better. Yeah, it's developing so quickly.

Jeff Lewis
Next week.

David Lat
Yep.

Tim Kowal
Yeah, I think it's incumbent on us, especially to our clients, not to continue doing things the old way when there might be new ways that are going to make us better and or faster. But there's a lot of hazard there because it might be faster, but not necessarily better. And the lure is there to just do it because it's faster without making allowances to make sure that it is at least as good as before, if not better Okay, now to reward our listeners patience and move on to the art of oral argument and talking about David's observations from watching the the oral arguments in the Trump v. Cook case before the Supreme Court and especially Paul Clement's performance there. David, you mentioned that Sarah Isgur of SCOTUSblog had called it a master class in oral argument and also weaved in several of Sarah's other comments in your piece about those three tips from Paul Clement's argument in Trump v. Cook. And you really distilled it down to three tips, but there's really a lot baked into each one of those tips. So, for example, the first tip, listen, listen, listen, is not just the same, you know, the kind of concrete tip that you would normally hear about oral argument. If the judge or justice asks a question, make sure you listen and answer the question. I think that one should go without saying by this point. But David, you observe something deeper about what Clement was doing during that argument and the way that he listened and perceived not just the question, but maybe the subtext of the justices' questions and concerns about his overall position in the case. Can you tell us a little bit more about what you meant by that first tip about the importance of listening to the panel?

David Lat
Yes, so it's not just about what the judges or justices are saying. If you were to look at their words on a cold transcript, it's also the way in which they are saying it. And this actually ties into our discussion about AI, because AI assistants cannot yet argue appeals. There was a pro se litigant in a New York appellate court who tried to do that and got in big trouble. So don't do that. But for now, humans get to argue these cases if for no other reason than that's how the judges want it and what the judges want the judges get. So you have these humans arguing these cases. And talented lawyers like Paul Clement listen very carefully. And they're not just listening for the substance, or like I was saying, which you can see on a transcript. They're listening for the tone. They're listening for who sounds skeptical, who sounds interested in a particular argument, who is gettable, and who is not. I guess the way to put it is, you mentioned Sarah, who has a new book coming out, but Sarah often likes to talk about the vibes. So they're listening for the vibes. What's the overall tenor of this argument? Where's it going? Where are the pressure points? What can I actually win on? So I think that is really important. And. You know, it's a tip, which I think is useful for your audience, but there is a question of how much of this can be developed and how much of this, like an athletic ability, how much of this is just innate? Some people are better at it; there's an aspect of EQ to it. Some people are better at sensing these vibes than others.

Tim Kowal
Now, if you're getting a vibe from one of your judges or justices that this jurist is just not going with your argument, what was Paul Clement able to do during his oral argument to react to that? Because he didn't go in, and all the justices were swimming with him. He was ready with other approaches. So, tell us about how he was able to bob and weave when he got some resistance from some of the justices

David Lat
So that leads to the second tip I mentioned in my article, which is to stay nimble. And this relates very much to listening, because you listen, you develop the vibe, you get a sense of that. And then that may lead you to go in a different direction than what you originally planned. So I think every appellate advocate goes up there with a list, whether a written one or just in their head, like Paul Clement, who doesn't use notes, of the points you want to stress or emphasize, or the points you think are key to your argument. But depending on the vibe you get, or even the specific substantive questions, you may decide, know what, I need to shift. I need to adjust on the fly because there may be an argument that I kind of put in there as a secondary or backup argument that turns out to be much more appealing. So it's interesting. He's gotten in a bit of trouble, as your listeners know, but Tom Goldstein, the very prominent appellate practitioner, Supreme Court advocate, Jeffrey Toobin did this profile of Tom in the New York Times Magazine back in December. And Toobin opens with the story of that big Google v. Oracle copyright case before the Supreme Court, where Tom went in there, and the justices were not necessarily picking up on the arguments he thought they were going to pick up on. And so he pivoted, and he stressed an argument that ended up being the winning argument, even if he didn't think ex ante that that was going to be the winning argument. So it's really important for advocates to stay nimble because you have to remember that justices or judges on appellate courts are still human beings. And the nice thing about oral argument is you get a peek at what's going on inside their heads. Otherwise, it's kind of a black box. You file these briefs, you wait a while. If the case is submitted on the briefs, you don't really get a sense of how it is going. But at least at the oral argument, that's your window, and that's your opportunity.

Tim Kowal
Let me ask a follow-up and maybe push back a little bit on the staying nimble point. What happens if, because the other side of staying nimble is the risk that you look like you don't believe in any of your arguments. You know, it's kind of like the magician saying, is this your card? No, it's not my card. Okay, no problem. I didn't really mean that card. Is this your card? No, not that card? Okay, let's just keep trying until we find a card that you like. It doesn't look like it's a trick anymore. You're just pulling out all the different arguments until you find one that lands Do you how do you how do you? effectively use the stay nimble technique without underselling your arguments or undermining your credibility. You know, in standing up for any one particular argument

David Lat
So I think Clement did a nice job of this in the Trump v. Cook argument, because before moving on to his backup or to what later got called the backup to the backup or the backup to the backup to the backup, he always emphasized, look, we actually stand by argument x, and here's why we think argument x is a good one. But if you're not persuaded by argument x, here's argument y. And look, lawyers can argue in the alternative. Sometimes there is a tension or an inconsistency. But for a lot of cases, X and Y are not mutually exclusive. So you can still say, look, we stand by X, as Paul Clement did. You know, you can say, well, look, I stand by the argument that, pre-office conduct by an official, things that Lisa Cook did before she became a member of the Fed, cannot be the basis for firing. But if you don't agree with that, and again, we stand by that, well, also, Congress always has the power to remove these officials. And well, if you don't buy that, again, we stand by that. But there's also an issue of due process. And was she given proper process before her termination? And so I think I get your overall point. And look, the other thing I would say is you don't necessarily abandon your argument at the first sign of resistance because look, this is, that's what an argument is about. means somebody saying A, somebody saying B, you can, you can try to advance A and look, sometimes maybe you'll get traction, but I think the talented advocate knows, okay, I've really tried selling them on A, and this is clearly not working. Time to go to B, the other thing that's tricky, and it's harder in some ways for people arguing before the Supreme Court compared to an appellate panel with three or five judges is when you have nine justices, you have a much more complicated calculus in terms of your path to victory and what one justice might like, another justice might not, and you have to figure out the shifting coalitions. It's definitely easier in the appellate courts, where you have fewer judges. And so you can say, OK, you know what? I can afford to lose Judge X. But judges Y and Z seem to really like this point. So maybe I'm going to stick with this point, even if Judge X is totally not buying it.

Tim Kowal
Yeah, and guess that strategy starts early on in the briefing. You need to prepare a menu of different ways to get to your result, each independently viable, but not all of them are going to command a majority, maybe. And so you may need to offer a number of independent routes to victory. And so if you start getting pushed back on one, you could say, well, I stand by that argument. But if you don't like it, hey, you don't. The good news is you don't have to agree with that argument because I got another argument for you. Let's try that one on and then just move down the list. Okay, and now to your third point, keeping it conversational and candid. Can you tell us a little bit about this tip, David? think Paul Clement himself, I think on your podcast, has referred to his style as conversational. Can you tell us more about how do you remain conversational at the Supreme Court? That seems like the last place you're going to have a genuine conversation, but you still have to give it a shot.

David Lat
Yeah, so it's really interesting. think sometimes people who are not familiar with the Supreme Court might be surprised. It's this very formal setting. There's this heavy red velvet curtain and these high-backed chairs, and it's all this marble, and it's very formal. But the style of the argument is actually conversational. It's a conversation between the justices and the advocates. And they ask questions, and you respond. And it's so active because the justices often have many questions; you don't really get the chance to engage in any kind of oratory or any kind of speechifying. So if you're used to TV or movies where some advocate gives a stirring oration and suddenly they win the case, maybe before a jury or something, that's not how things work in the Supreme Court. The questions are often very specific. The answers are also quite specific. And the person, the advocate, may not even get to say that much before another justice jumps in with a different question. So you can't even get ahead of steam, going even if you wanted to pontificate in some kind of very eloquent way at the Supreme Court lecture. So it's just a different style. And it's definitely not the style of delivering an opening or closing in a trial court. And I think it's also a little bit different than even an appeals court, just because there are so many more of the justices. And the way that oral argument in the Supreme Court has evolved, at least, is that the bench tends to be very hot. They have a lot of questions. There were times when I was up there as an appellate advocate, and I could tell that my side was going to win. And you get up there, and you make your points very briefly, but you don't want to waste their time. And so maybe the better part of Valor is saying, well, if the panel has no further questions, we rest on our papers or whatever you want to say, and then get out of there. But you don't often see that in the Supreme Court, especially in the high-profile cases. Some of these arguments span two or more hours, especially in the latest version of their format. So it is a little bit different.

Tim Kowal
I like to think of arguments in terms of the classical ethos, pathos, and logos. And I always figure that the logos is going to be made clear in my briefing. If I haven't made the logo side of my argument clear in the briefs, then I've got bigger problems at oral argument. Oral argument is for me to either demonstrate pathos or, probably most important, would be ethos. And I think that may be where it gets to your point about the importance of keeping it conversational and candid. Do you get that sense that that is where the justices are gonna get a sense of who you are if you're not already Paul Clement and you're on a first-name basis with the court? But they're gonna get a sense of who you are, what kind of advocate you are, and kind of the credibility of your client by way of the credibility of you as counsel.

David Lat
Yes, absolutely. And again. This is where that human touch matters because we're not having AI assistants or robots do these arguments. And your credibility is key as an advocate and as a lawyer more generally. So oral argument is an opportunity to burnish that credibility. It is also an opportunity to lose it if you make a misrepresentation where you don't sound like you understand your case, where you are evasive when the judges or justices ask questions. So I totally agree with that point, Tim.

Tim Kowal
Okay. Well, thank you so much, David. We're going to leave it there unless you have anything else, Jeff. I was just looking through my notes here. But there are just so many good things from your article about the Trump v. Cook case, including, you know, how Clement had admitted on the subject of keeping it conversational, I think, when Justice Alito responded to one of his answers.

Tim Kowal
as maybe being a little slippery. And he said, yeah, I admit it might be kind of a heads I win, tails you lose framing. So there was a sense that he was trying to position his argument, you know, not to be slippery, but look, there are many reasons why my client wins. And it's the administration being overly aggressive here. And that's why it needs to be sent back, because I've given you, I think, as Sarah Isgur pointed out, I've given you 97 different ways that you need to send this back. I may not be right on any of them, but if I'm right on one of them, you've got to send it back. Jeff?

Jeff Lewis
I'm gonna add two things to the conversation if I could. One, David mentioned an article in the New York Times about a fantastic article, not just to be a voyeur about poker gambling, but about the show notes. That's one thing. And the second, David, I'm not sure if you shared the name of your podcast, but when our listeners get done listening to this, they want to find your podcast. What is the name of that podcast?

David Lat
yes. Thanks for the opportunity, Jeff. It is original jurisdiction, just like my Substack newsletter of the same name. And you can find the newsletter at davidlat.substack.com. And I'm very easily findable through there, through social media. And I always love hearing from people.

Jeff Lewis
Original Jurisdiction. Fantastic.

Tim Kowal
All right, thanks again, David Lat. That's gonna wrap up this episode, Jeff. If you have suggestions for future episodes, please email us at info@calpodcast.com. In our upcoming episodes, look for tips on how to lay the groundwork for an appeal when preparing for trial. Thanks again.

Jeff Lewis
See you next time.