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.
My latest guest is an acclaimed appellate and Supreme Court advocate, Jennifer Bennett of Gupta Wessler. To introduce her, I’m going to turn over the floor to a former podcast guest: Judge Vince Chhabria (N.D. Cal.), for whom Bennett clerked. When I mentioned to Judge Chhabria that I was going to be interviewing Jennifer, he immediately moved into testimonial mode:
Funny, I was going to email you to suggest that you interview her! She is truly one of one. She recently won her fourth Supreme Court case, GEO Group v. Menocal. Despite representing workers in all four of her cases (the first three on arbitration), she has won all four of them, and each one of them has been unanimous. In other words, this lawyer for working people has never lost a vote in her four cases on behalf of working people at the current Supreme Court!
She also just argued her fifth case at the Court, Flowers Foods, Inc. v. Brock—the arbitration case about ‘last-mile’ drivers. It seems like she might win that one, too.
Jenn was my very first law clerk—I refer to her as Chhabria Clerk Zero. For around three months, before the other law clerks started, it was just me and her in chambers, sifting through our new cases and figuring out how to handle them.
Steve Berzon came to my informal swearing-in, I was lamenting not having immediate law clerk help, and he mentioned that this person who clerked for [Judges] Marsha [Berzon] and Jesse [Furman] had about six months to kill before starting a fellowship at Public Justice and might be interested. I was so lucky to have Jenn. Given how amazing she is and her experience in Jesse’s chambers, she was able to get me up and running in a way that would have been impossible otherwise. She played a big role in teaching me how to be a good district judge.
Thanks to Judge Chhabria for the intro, and thanks to Jenn for joining me.
Show Notes:
Jennifer Bennett bio, Gupta Wessler LLP
High Court Bar’s Future: Gupta Wessler’s Jennifer Bennett, by Jeff Overley for Law360
US Supreme Court weighs bid to narrow worker arbitration exemption, by Daniel Wiessner for Reuters
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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-fourth episode of this podcast, recorded on Wednesday, April 1.
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Among advocates who have argued before the U.S. Supreme Court multiple times, there aren’t many who are undefeated. So Jennifer Bennett, a principal at Gupta Wessler in San Francisco, stands out. She has argued five cases before the high court, and of the four that have been decided, she won all of them—with unanimous decisions each time.
Like her colleagues at Gupta Wessler, a national appellate and complex litigation boutique focused on representing plaintiffs and public-interest clients, Jennifer advocates on behalf of workers, consumers, and vulnerable plaintiffs. So her record of success before the current Supreme Court—which is, on the whole, a rather conservative and business-friendly court—is especially impressive.
How has Jennifer managed to achieve such a great track record? What advice would she offer to appellate advocates about persuading a sometimes skeptical bench? How does she get ready for a Supreme Court oral argument? And does she use AI to help in her preparation? Without further ado, here’s my conversation with Jennifer Bennett.
Jennifer, thank you so much for joining me.
Jennifer Bennett: Thank you for having me. I’m really excited to be here.
DL: Let’s start at the beginning. Tell us about your background and upbringing. Where did you grow up?
JB: I was born in Baton Rouge, Louisiana, but I grew up mostly in L.A., which meant—I am told I have no actual recollection of this—that I started speaking with a Southern accent, then moved to L.A. and promptly tried to get rid of it, so that I could sound like everyone else. And then, of course, I grew up, promptly regretted that, and wished I hadn’t done that.
DL: You grew up in Southern California, but you now live in the Bay Area. Where’s your allegiance in the whole Northern versus Southern California battle?
JB: Oh, a hundred percent Northern California. I am comfortable when the temperature is between 68 and 72 degrees, and there’s approximately one part of the world that is like that. And I also hate driving, so Northern California all the way.
DL: Speaking of Los Angeles—there was that iconic show, L.A. Law—did you have any lawyers in the family, or any early exposure to the legal world?
JB: My sister is a lawyer—and she is younger than I am and also smarter and more talented, so I’m very glad we’re in different parts of the law—but she has always known she wanted to be a lawyer. When I was a kid, I think I wanted to be a trash collector. My sister wanted to be a lawyer. And so, in some ways, I have followed in my younger sister’s footsteps. I didn’t think about the law until well after college.
DL: What led you to go to law school? And I don’t know the gap between you and your sister—did she go to law school before you, even though she’s younger?
JB: She did not go before me (I think much to her chagrin). I went just before her, and we actually went to the same law school, and we sound alike and look a little bit alike. So there were professors who just thought there was this one law student who was there for a very long time.
In terms of how I decided to go to law school, after college, I was working at an organization that taught kids to sing. I very much believe in music education; I think it’s really important. It provides a safe space for kids to learn how to use their voice. It builds confidence. There are all sorts of really great things. But it turns out there are a bunch of problems that music education can’t really solve. Families would be evicted, people would lose their jobs, they’d have payday loans that they couldn’t pay off. And I saw this over and over and over again. It was great to teach their kids to sing, but it wasn’t solving many of the problems. And I had this idea, a sort of vague idea, that maybe law would be a better tool to actually be able to address some of those problems. And so, almost on a lark, I ended up applying to law school, thinking that maybe this would enable me to do the things I wasn’t able to do there.
DL: A lot of people go to law school saying or thinking they’re going to do one thing and then end up doing something totally different. But you ended up doing the same thing that you thought you went to law school for—am I right about that?
JB: Maybe, which is to say I went to law school because there were problems in the world that I thought law was a good tool for solving, I continue to work on exactly those problems, and I feel really grateful to be able to do that. When I went to law school, I had no real sense of what a lawyer was or did or how they used those tools to solve problems. I also went to law school just before plaintiffs’ lawyers associations popped up at basically every law school. So my vision of what kind of lawyer you could be was: you could be a corporate defense lawyer, you could be a government lawyer, or you could work for a nonprofit. I didn’t actually know that plaintiff-side lawyering was really a thing; I don’t know who I thought was on the other side of the “v” in these cases where it wasn’t a nonprofit. And so what I do now is not really practicing the kind of law that I knew existed when I went to law school. But you’re totally right in terms of fulfilling my vague vision of what a lawyer could do. I feel really lucky to be able to do that.
DL: It sounds like in many ways you’re vindicating the purpose or objectives that motivated you to go to law school, but maybe not quite in the way that you originally envisioned.
JB: Yes, a hundred percent.
DL: Let’s go from law school to your legal career. What was your first job out of YLS?
JB: I clerked. Then after clerking, I worked at Public Justice, a fantastic nonprofit that does a wide range of public-interest work. I worked in the Access to Justice Project, a generalist appellate project that works on all sorts of access-to-justice issues, by which I mean issues about people being able to get into court to vindicate their rights—standing, personal jurisdiction, those kinds of issues, as well as working on court secrecy, fighting the unnecessary sealing of court records, so that people could see what’s actually going on in the cases that affect them.
DL: You mentioned you clerked. You actually clerked three times...
JB: Too many times!
DL: … for three of my favorite judges: Judge Marsha Berzon of the Ninth Circuit, Judge Jesse Furman of the Southern District of New York, and Judge Vince Chhabria of the Northern District of California. I’m sure you learned a ton from those experiences with three very prominent members of the judiciary. Can you share with us one thing you learned or took away from each clerkship?
JB: All three of them are just brilliant lawyers and phenomenal writers. I do not think I would be where I am today without their mentorship, both as a practical matter and in terms of my career and things like that. But in terms of being specific to each person:
The one thing that I would say for Judge Berzon is—she tells this to all of her clerks, it’s really stuck with me, and it seems so simple—but one of the first things she tells you is, read the statute. And that seems like such obvious advice, especially in a statutory case—but it is so frequently not done. And also what she meant by that is, don’t just assume that your initial instinct is right, or that the way courts have gone is right. What you want to do when you get a case is to figure out, “What is this case about,” and go back to first principles and read the whole statute—as opposed to starting from what have other courts have held in this area. I have found that advice just incredibly useful throughout my career.
Then I clerked for Judge Furman. And Judge Furman is unlike anybody else I have ever met in terms of, well, many things—but he has this unique capacity to see humanity in everyone, and really treat everyone with respect and dignity and empathy and true connection, whether it was litigants in the court and pro se litigants and big corporations, whether it was his clerks, whether it was courthouse staff, whether it was his kids. I don’t think I’ve seen him ever, for example, look at his watch when talking to someone. Or you would see a pro se litigant come in, it would be very difficult to understand what they were saying, and he took the time to understand what they were saying, to explain things to them in a way that was not patronizing. It was a genuine human connection, and I felt that as a clerk. And that to me is a model of not just how to be a lawyer, but how to be a person, that I found really incredible. And I’m surrounded by a lot of people who treat people very well. He is, in my view, just unique in his ability to do that and his dedication to doing that.
Then one thing about Judge Chhabria—and this is similar—is that he thinks a lot about the power he has as a judge, the power courts have, and how that’s going to impact people. I was Judge Chhabria’s first clerk, and most judges, when they first get on the bench, spend their time picking out couches and rugs and going to seminars and learning from other judges. And yes, Judge Chhabria had furniture, went to seminars, and learned from other judges—but when I first got there, he and I spent a bunch of time going over this backlog of habeas cases, and he felt that it was very important that that backlog get addressed. So when other judges would be enjoying their free time before their docket really set in, he said, “Look, this is something I can do.” And he spent that time, instead of picking out couches, going through habeas case after habeas case. To me, thinking about what power I have in the world, how it can be used, and how it’s impacting people have all really stuck with me.
DL: I will totally second your observations on Judges Furman and Chhabria. I’ve known Judge Furman since law school, and he’s definitely a mensch. And Judge Chhabria is one of the most thoughtful members of the judiciary when it comes to the judicial role (and I would refer listeners back to my own podcast episode with him).
Going back to your career, where did you go after Public Justice?
JB: Gupta Wessler. I’ve had only two legal jobs since clerking, and the same person gave me both jobs: Matthew Wessler hired me at Public Justice and, I think, took a leap. I was probably the worst interviewee. He has never said this to me, but my recollection of that interview is, I was probably the worst interviewee he has ever experienced. I didn’t know anything about how you’re supposed to interview for law jobs. But he took a risk, and then I came to Gupta Wessler after that firm had been around for a while.
DL: And how many years ago was it that you joined the firm?
JB: About five years ago.
DL: And you launched their West Coast office, I believe?
JB: Yes, initially abortively, because I joined during COVID. And so the idea was, we were going to build an office, it would have a physical space, it would be great, everybody would come in—and then came lockdown. But yes, we are now in earnest building a West Coast office, which is really exciting to me, and it just has wonderful people and gives us an opportunity to build something on this coast. The firm’s D.C. office has always been inspiring to me, and it’s one of the reasons I wanted to come to this firm, and I’m very excited about being able to build a version of that on the West Coast.
DL: I want to go back to something you said about Judge Berzon, when she told you to go back to the text and to first principles. It’s very apt for your current practice because you do a lot of work before the Supreme Court—and if any court has the luxury of going back to first principles and text rather than being bound by what courts have previously decided, it’s that court.
So, it’s very apt for you, but let me ask you this: we’re speaking a few days after your fifth oral argument, in Flowers Foods, Inc., v. Brock. I listened to the argument, and I have to confess: I think I’m a reasonably intelligent person, and I’ve listened to a gazillion arguments over the years, but this one was hard to follow. It’s a pending case, so I understand you may have to be somewhat circumspect, but maybe even just based on public filings or the briefs or the record, what is this case about, in terms of the legal issue?
JB: Totally fair. It’s quite difficult to divine how hypotheticals about what would happen in 1925 if the title to goods transferred from one person to another along certain points of a journey were relevant. At a high level, the legal question is really, “Are commercial truck drivers transportation workers?” And you would probably say that seems obviously yes, and I would agree with that. But for purposes of the Federal Arbitration Act, trucking companies and companies like Flowers (the defendant in that case), which have huge trucking arms, have been trying very hard to get courts to hold that the answer is no. And the reason they’re doing that is because the Federal Arbitration Act, which is the statute that companies use to mandate that their workers go to arbitration and to kick them out of court, has an exception for transportation workers. And so companies don’t want their workers to be transportation workers exempt from the statute.
Where it gets confusing is that the Federal Arbitration Act doesn’t actually use the words “transportation worker.” The Supreme Court has said the exemption applies to transportation workers, but the text of the exemption is “seamen, railroad employees, and any other class of workers engaged in foreign or interstate commerce.” And so the question in the case is about the scope of the exemption: “Is the plaintiff a member of a class of workers engaged in foreign or interstate commerce”? And here, the plaintiff, Mr. Brock, is a last-mile driver (think Amazon or UPS drivers). And the question is, “Are last-mile drivers engaged in interstate commerce in the same way that seamen and railroad employees were in 1925?” And the fight that you saw was a fight about how to figure that out.
We, as counsel for Mr. Brock, think that the way to figure that out is: you look back to 1925, which is when the statute was passed, and ask, what did the words “engaged in interstate commerce” mean? And then Flowers’s argument was, “No, no, no, that’s not how you interpret the Federal Arbitration Act. The Federal Arbitration Act is basically sui generis, and you don’t really go and look at what the words meant in 1925.” They’re arguing, “You should add or adopt this additional requirement here”—companies have tried different kinds of requirements here—”and our proposed requirement is you have to touch a vehicle that crosses state lines.” And so the questions and hypos they got were, “Okay, this requirement that you’re trying to add appears nowhere in any other statute. It’s not in the case law. It doesn’t really come from what the words mean. So how would this apply in the real world? What would happen if we adopted this requirement?”
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So just to clarify the term “last-mile driver”—and this came up a lot at the argument—one point that was emphasized by counsel for Flowers was that the last mile often is intrastate. This good might have traveled all across the country to make its way to the final seller or user or customer, what have you—but if the last mile is intrastate, how is that person engaged in interstate commerce? So the stuff about vehicles crossing state lines, and the stuff about loading and unloading, that all went over my head. But I can understand this very simplistic argument: “If the worker doesn’t cross the state line, then they’re not engaged in interstate commerce, and if they do cross a state line, then they are.” That would seem to be a very bright-line, clean rule.
JB: That’s definitely part of what’s going on here—it is a clean, bright-line rule—but the Court rejected it a couple terms ago in Southwest v. Saxon. And the reason the Court rejected it is because interstate commerce has never been understood to just mean physically crossing state lines. The core of interstate commerce is sending goods from people or companies in one state to people or companies in another. You can imagine commerce and the economy would essentially cease if all that was happening is you took a good from one side of the state line to the other side of a state line; the supply chain is then broken. And so interstate commerce has always been understood to be, especially with respect to goods, when you ship the goods until they get to where they’re actually going.
DL: This is a totally separate issue because your case is a statutory case, but it seems to also plug into this line or body of constitutional law holding that Congress has very broad power under the Commerce Clause. But let me go back to the point you were saying about arbitration. In terms of the real-world impact of this case, it sounds to me like it is part of what you could call an ongoing campaign by corporate America to force more parties against them—whether it’s workers or customers or what have you—into arbitration, rather than getting their day in court. Is that fair to say?
JB: I think that’s right. Even in this narrow, transportation-worker context, you’ve seen initially the argument to the Supreme Court was—this is before my time—that the exemption should cover all workers. And then corporations came back and said, “No, it should really just be transportation workers.” And the Supreme Court said, “Okay, that’s a very narrow interpretation. We’ll hold that everybody can arbitrate, but transportation workers are exempt.” And now you see case after case coming back and trying to add more and more limits that have less and less textual basis for them: “No, they have to touch a vehicle,” or “No, they have to physically cross state lines,” or “No, it has to be Tuesday with a full moon and a leap year.” You’re right about that.
DL: So this is interesting, your focus on the text—it actually ties into what I want to ask you next. If you prevail in Flowers Foods, this will be your fifth win, in terms of the five cases you’ve argued. You won all four of the cases you previously argued, unanimously, and you did so arguing on behalf of workers and vulnerable plaintiffs, before a court that isn’t always sympathetic to these interests. How would you explain that remarkable win record—besides, of course, your brilliance as an advocate, and the righteousness of your clients’ causes?
JB: I think there are maybe a few factors. One, I think being right is very helpful—and I realize that sounds glib and I don’t mean it to, but genuinely. And what it means to be right can change. So, for example, in the very first Supreme Court case I argued, before the team that was arguing these issues got involved, plaintiffs were losing all across the country, and that’s because courts said, “This is a statutory case,” and courts had this sort of intuitive sense to modern ears about what the statute meant. We were like, “Well, I wonder if that was actually the ordinary meaning of those words when the statute was passed.” It turns out it definitely wasn’t, and there was just sort of a wall of evidence to that effect.
So being really comfortable with a text-and-history mode of interpretation, and being able to present a sort of impenetrable legal case that the ordinary meaning of the text at the time and the history all say X—that has been very helpful. There might be justices on the Court that disagree with me as a policy matter about whether it would be good or bad for a statute to mean a particular thing, but can join on how to interpret the statute and reach the same place. That has been very helpful.
DL: Let me ask you a weird question, then. Would you describe yourself as sort of a progressive originalist? Or do you just take on the originalist role for purposes of arguing before an originalist-oriented Supreme Court?
JB: I think maybe both—which is to say, I don’t know that anybody would say the original meaning of the statute or the Constitution doesn’t matter. It does matter, genuinely, as a commitment to what it means to interpret the law. I also think if you want to win cases before the Supreme Court, those are the kinds of arguments you have to make. So, it’s both.
And perhaps there are different courts in which I would make different kinds of arguments. For example, there are state supreme courts that have their role, as given to them in the separation of powers in that state, which includes both a legal-interpretation role and a policymaking role. And in some of those courts, I would make both the textual arguments and the policy arguments, and I might make them in a different way than I would make them in the Supreme Court, or strike a different balance between them than I would in the Supreme Court. But every court does care about both of those things, and both of those things are always relevant.
DL: That makes total sense. And your point about understanding the court you’re arguing before also makes perfect sense.
So, looking back over your five arguments, do you have a favorite moment or an exchange that you might want to highlight? It could be a dramatic moment or a funny moment or something you handled well or something you flubbed. Is there something or some things that jump out at you?
JB: Yeah, maybe there are two things. First, this would not have been evident to anyone else because it happened in my own head, but the first time I was ever in the Supreme Court was my first Supreme Court argument. And you walk into the Court, and the bench is incredibly close to your face. And I just remember thinking, “If they hate you, they could spit at you!” (Nobody’s ever done that.) You can’t see everyone at once. And I just remember thinking, “This is the most intimidating panel interview anybody has ever had,” and just being surprised. I don’t know why, but I expected this vast room where everybody was very far apart. But everybody’s really close together having this conversation, which was very striking to me.
I guess here’s the second thing I would think about. One hundred percent of the time advocates are told, “Never try to be funny; don’t try to be funny.” I think that’s right; it will never go over well. But there was maybe—I think it was the Saxon argument—the argument was about which kinds of transportation workers might be exempt from the Federal Arbitration Act. That case was about airline employees. And I think Justice Thomas asked me something like, “All right, where does this end? What other kinds of transportation workers are there?” And I listed all of the ones I could think of—like seamen and railroad employees and airline employees and bus drivers and truck drivers—and I was trying really hard to be complete and be as candid as possible with the Court to try to answer the question. And in my head, I was like, “I should really mention space; it may come up at some point.” And it just came out: “And also there might someday be space transportation”—which maybe was not strictly necessary to fulfill the duty of candor to the court, but immediately sort of brought down the temperature, which I appreciated.
DL: That’s such a great story and point, because it’s sometimes hard to sense because we don’t have cameras in the courtroom, but there’s a vibe or a feeling in the Court, and sometimes it can be very tense. And sometimes those moments of humor really can take the temperature or the pressure down in a very helpful way.
So let me ask you this: how do you prepare for an argument? And more specifically, is there something that you do that’s different? Because I’ve had many Supreme Court litigators on the podcast, and of course, we all know the obvious themes: know the law and the facts backward and forward, do plenty of moots, and this and that and the other thing. But is there anything you do in preparing, or maybe even in arguing, that is a little different or unique?
JB: Well, I’m not sure because I haven’t talked to everybody about how they do this, but there may be a couple things that come to mind.
One is—your mileage may vary on this—but a couple Terms ago, I had an argument, the same argument actually where space came up, where the question was like, “What kinds of workers are exempt from the Federal Arbitration Act?” And we anticipated approximately a million hypotheticals about various kinds of workers. And my colleague brought in his child’s Richard Scarry book about the airport, and we just sat around and somebody was like, “What about the bear fueling the plane? Is the bear exempt from the Arbitration Act? What about the cat, the cat taking baggage—exempt?” Obviously, there will not be a Richard Scarry book for every argument, but this idea of thinking through very basic, real-world examples, and sitting around with your brilliant colleagues who are much smarter than you and have all of this experience but are not as keyed up as you are to think about, as a practical matter, “Is the bear going to be exempt?”—I found that kind of thing really helpful, and I tried to emulate it, actually, in future arguments.
The other thing I do—which maybe a bunch of people do, I’m not sure—is I take a lot of walks and have a lot of arguments with myself in my head, and then come home and immediately write down the questions that Justice Bennett asked that Advocate Bennett was not able to answer very well, and I think through those and talk with my wonderful colleagues about them. And I find that kind of practice very helpful.
DL: One of my recent podcast guests, Jed Bergman, talked about how when he’s preparing for an oral argument and his colleagues are not around—maybe he’s gotten up super early, and everybody’s asleep—sometimes he’ll make AI his sparring partner or interlocutor. I’m curious, and I ask this of almost every guest I have lately: are you using AI much in your practice? If so, how? And if not, why not?
JB: Not a tremendous amount, largely because of two reasons. One is, I don’t think AI can handle the kind of research and writing we do yet. I think it’s much more helpful potentially in a trial practice, where you’re sorting through large amounts of discovery, things like that.
And the second reason is, I am incredibly lucky to have a phenomenal set of brilliant colleagues who are pretty much always up for chatting about issues, whether they are involved in the case or not. And 100 percent of the time, I would rather chat with a colleague than with Claude.
And so it’s probably partially a factor of just where I am and the firm I’m at, where I just am surrounded by people who are so generous with their time and so wonderful about being open to talking through issues.
DL: That’s a totally fair point. I suspect that how much one turns to AI will depend both on their practice area and also on their practice environment. If I’m a solo practitioner who doesn’t have the incredible colleagues that you have at Gupta Wessler, then maybe it is helpful for me to turn to an AI solution.
So I have one other question about the Supreme Court. We are talking a few hours after the Supreme Court heard oral argument in the birthright-citizenship case. And there have been and will be some very high-profile cases before the court this Term, including birthright citizenship. Of course, we had tariffs already.
But what’s interesting is you also work on some cases that sometimes fly beneath the radar—very important to workers, to businesses, to access to justice, what have you, but maybe they’re not necessarily the ones that are burning up Twitter (or I guess I should say X) or Bluesky. But is there a case or two this Term that you’d like to highlight as maybe a sleeper case, one of these cases that’s not getting the attention that it actually deserves?
JB: Can I cheat? There’s a suite of cases before the Court this Term that all get at the same issue from various perspectives. There are a number of cases—at least three that I can count this Term—that are about essentially variations of the question, “Are government contractors treated the same as the government, and are there special defenses for companies that work for the government?” So I’m thinking of GEO v. Menocal, which was our case; Galette v. New Jersey Transit Corporation, which was a case about whether New Jersey Transit was essentially an arm of the State of New Jersey that should get the same sovereign immunity that New Jersey gets; and Hencely v. Fluor, which is about military contractors.
They all arise in different contexts, but they’re all examples of corporations arguing, “We contract for the government, we sell things or services to the government, and therefore, we should get all the immunities that the government gets.” And at least in the first two cases that have been decided, the Supreme Court has rejected that; we’ll see what happens in Hencely. But it’s really important, especially as both state and federal governments outsource more and more work to corporations, how you treat those corporations, and whether they can be held accountable for violating the law.
DL: That’s interesting. And I always like those thematic connections between cases, because sometimes I have these shorthands in my head of, “Oh, this is turning out to be the arbitration Term,” or this is turning out to be whatever the flavor of the Term might be. So that’s really interesting; I hadn’t thought about that.
Shifting to focus a little more on Gupta Wessler, which we’ve talked about here and there: you are an appellate and Supreme Court advocate. A lot of what you do involves the Supreme Court and Washington, D.C. But you’re a Supreme Court advocate out on the West Coast. Does that change your work or affect things, either practically or in terms of a mindset?
JB: I definitely am on a plane more than my East Coast colleagues, but otherwise I think people are often told, “If you want to be an appellate advocate, you have to live in D.C.,” and I just think that is not true. I feel very lucky to be able to live in San Francisco, and there are planes, and so it has never been an issue that I live on the West Coast.
I love D.C. I would be very happy living in D.C. When you live in D.C., you are surrounded all of the time by lawyers and politics. And I do wonder if living somewhere else gives you a bit of a different perspective about what you’re arguing and how it affects people and maybe turns down the temperature, makes things feel not necessarily as politicized as they might feel if you were constantly stewing in heated battles every day. I’m not sure about that. But what I will say is I do not think that people who want this kind of a job need to live in D.C.
DL: That’s helpful; I do have a fair number of listeners who are law students and young lawyers, so takeaways like that are always helpful. And the point you were making about perspective is interesting, because your earlier comment about the Richard Scarry jobs struck me as suggesting that, even though you’re very conversant with the abstractions of the law, you also want to know the on-the-ground, real-world impacts. And in some ways, another way of phrasing your point is, maybe if you’re outside of the D.C. bubble you’re more attuned to the real-world impacts of cases—as opposed to being in a place where at the cocktail party they’re talking about the Commerce Clause or something like that.
JB: I would hesitate to say that my D.C. colleagues are less attuned to the real-world impacts or people who live in D.C. are somehow less attuned to the real-world impacts. But maybe the people I talk to on a day-to-day basis who aren’t my colleagues would never be able to tell you what it means to be engaged in interstate commerce. And so one thing living on the West Coast does is, I am often explaining my cases and my work to very smart people who have absolutely no familiarity with what I’m talking about. And I do think that breeds a different way of explaining things that is maybe helpful.
DL: That makes perfect sense. So one of my interests as a journalist is the business of law, and I’m sort of the rare crossover person who’s interested in the Supreme Court and the lower courts, but also law firms—and I kind of like to get under the hood of firms. Gupta Wessler is a fascinating firm. I feel like, when people think of elite litigation boutiques, sometimes they think of these more conservative or right-of-center ones, like a Consovoy McCarthy or Cooper & Kirk. But in recent years, you’ve seen places like Hecker Fink and Kaplan Martin, and for a while now, there have been these very high-powered boutiques that are more on the liberal or progressive side, handling the highest-profile, highest-stakes cases—Gupta Wessler, of course, but I should mention others, like Dunn Isaacson Rhee.
So here’s one thing I wonder about. If the right-of-center boutiques represent large corporations, much like large, Am Law 100 firms, you can see the economic model there. But you and other left-of-center boutiques are representing workers, you’re representing plaintiffs in employment cases or things like that, the so-called “little guy” or “little gal.” Can you talk about what makes the firm work as a business, given that your client base is not necessarily rolling in dough?
JB: There are a lot of really important public-interest issues that come up in big cases like class actions, appeals from jury verdicts, or MDLs. And the way plaintiff-side trial lawyers are able to support those practices in those cases is typically on contingency. And so they take, of course, the risk of the case, but also the reward. And often we will have a similar model, and we will also work at least partially on contingency and have the same effect.
We’re very lucky in that we are both (1) a private firm, and so we have those kinds of arrangements, and (2) a public-interest firm, which means I have never worked on a case at the firm that I did not want to work on because we needed to because of the financial arrangements. We work really hard to make sure that we can stay true to our public-interest mission, while also, very importantly, paying everybody who works at the firm and our rent and things like that. And the partial-contingency model that plaintiffs’ firms use is a model that works for us.
DL: That’s interesting: you can, in other words, even for appellate work, have some kind of alternative fee arrangement, as opposed to straight-up billing by the hour. Because again, traditionally you think of plaintiff-side trial work as maybe alternative fee arrangement or contingent fee, but you think of appellate work as very bill by the hour. But it sounds like you’re open at Gupta Wessler to other arrangements.
JB: Yes, absolutely.
DL: At what stage do you typically get involved with a case at Gupta Wessler? Because you’re probably most well-known for your appellate and Supreme Court matters, but are you often brought in at the appellate stage, or are you often with the case from its inception?
JB: It varies a lot. We commonly will come in at the appellate stage, sometimes at the Supreme Court stage—but also we will come in sometimes, for example, at the post-trial motion stage, when there’s going to be an appeal of a jury verdict, to work with the trial team on setting up that appeal. Sometimes we will come in, either officially or unofficially, at the beginning of the case, if it has very obvious appellate issues. We would love to have a conversation with people at the beginning of that case to talk about what those issues are going to be and how to set them up. And that may be official representation, and it may also just be informal strategic conversations as the case goes along, knowing that what we are doing is setting up the appeal.
DL: Now let’s turn to my speed round. These are four questions, and they are the same for all my guests. 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 a more abstract system.
JB: So this is a statement against interest, but maybe the thing I like least about the law is that it requires lawyers. And what I mean by that is: big corporations and the government are well-resourced; they will always have a fleet of very good well-resourced lawyers. Real people often don’t. And so you see all the time that people who don’t have access to lawyers don’t know that they can do anything about what happened to them, or they do get into court, but they lose because they’ve waived a bunch of issues, or because the case wasn’t argued well.
And that’s the thing that I like least about the law. It’s not this abstract thing that is just given from on high that means the same thing no matter who represents you. You have to have good representation. It is, again, a reason that I feel so lucky to be a member of Gupta Wessler, where the mission is essentially, “provide the kind of representation that Biglaw provides to corporations, that DOJ and the SG’s office provide to the government, to real people”—and to be able to do it on the same level.
DL: My second question is, what would you be if you were not a lawyer?
JB: I genuinely have no idea—before I became a lawyer, I thought maybe a choral conductor. Being a lawyer has felt natural to me in a way that nothing else has. I’m not very good at anything else. And it feels like it is sort of the perfect fit between what I would love to do in the world and what I was okay at. Before becoming a lawyer, they never really meshed. I was a musician before becoming a lawyer. I could imagine still being a musician now; maybe that is what would’ve ended up happening. But it’s really hard to imagine doing something different.
DL: Well, I always love talking to lawyers who love what they do. My third question is, how much sleep do you get each night?
JB: Somewhere between two hours and 12 hours, which is to say, I don’t have sleep down. It really, really varies a lot. Sleep is very important. People should try to get sleep. I am incredibly bad at it.
DL: Okay; that’s the widest range I’ve come across. My last question is, any final words of wisdom, such as career advice or life advice, for my listeners?
JB: I guess maybe two things I can think of. One is, find a place to work where you like the people you’re working with. And that seems so obvious, but often law students coming out of law school are really focused: I know I want D, and what is the best possible strategic thing to do at levels A, B, and C? And I think, one, that’s very difficult to map out. You can look at me: I knew nothing, and I have this career that I love, and I didn’t know close to what current law students know about potential paths in the law and how to get there. But also being happy in what you do is just so important and will make you a better lawyer. And having colleagues that are committed to your success and to mentoring you and to helping you is so important. Prioritizing that, doing your version of good in the world, plus doing it with people who you think are smarter than you, better than you, more kind than you in every possible way—it just is an incredible thing to be able to do.
DL: And you said you had a second point, or was that baked into what you just said?
JB: Good—if you have two points, remember the second one! The other one is maybe somewhat related: I don’t think there’s a right way to get where you want to go. And sometimes where you think you want to go may not actually be where you end up wanting to go—which is just another way of saying, I talk to so many law students who are so concerned about taking the right classes and doing exactly the right thing to be exactly where they want to be. And things can be more serendipitous than that. I realize this is speaking mostly to the people who listen who are law students, but you could have a very successful, fulfilling career, without taking the one class that everybody says you absolutely need to take because it’s taught by a judge, or without clerking for a person you don’t necessarily want to clerk for, or planning everything out from the beginning. Leaving room for that, I think, is important.
DL: That’s great advice. And your own career exemplifies it, just in terms of taking some unexpected or unplanned steps and having it all end very serendipitously. So thank you so much for joining me, Jennifer.
JB: Thank you for having me. It was really great to talk to you.
DL: Thanks so much to Jennifer for joining me, and congratulations to her on her excellent record before the Supreme Court.
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