Conversation
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‘There’s Always A Way’: Jaime Santos
sourceEarlier this month, Jaime Santos joined Proskauer Rose, making her the latest in a series of appellate advocates to switch firms in 2026. She came from Goodwin, where she practiced for more than a dozen years and served as co-head of the Supreme Court and appellate practice.
What led Jaime to make the move, and what does she think is driving all the lateral hiring in the space? With a new Supreme Court Term starting this coming Monday, which cases is she watching? And as the first ERISA and employee-benefits lawyer I’ve had on the podcast (after more than 100 episodes), what does she see as the key emerging issues in the field?
Thanks to Jaime for such an interesting and inspiring conversation, and congratulations to her on joining Proskauer.
Show notes:
Jaime Santos bio, Proskauer Rose LLP
Goodwin Supreme Court Group Chief Santos Bolts for Proskauer, by Meghan Tribe and Jacklyn Wille for Bloomberg Law
Proskauer Hires Goodwin Procter’s Supreme Court Co-Head, by Kevin Penton for Law360
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Jaime Santos (courtesy photo)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 transcription 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 dot substack dot com. You’re listening to the 106th episode of this podcast, recorded on Wednesday, September 23.
Thanks to this podcast’s sponsor, NexFirm. NexFirm helps small and midsize law firms offer Biglaw-caliber benefits at small-firm prices. To learn how NexFirm can improve your employee benefits program, call 212-292-1002 or email betterbenefits at nexfirm dot com. Want to know who the guest will be for the next Original Jurisdiction podcast? Follow NexFirm on LinkedIn for a preview.
My guest today is Jaime Santos, co-chair of the Compensation and Benefits Litigation Practice at Proskauer Rose and one of the nation’s leading appellate and ERISA litigators. We began our conversation by covering Jaime’s impressive and inspiring career path, which took her from a trailer park in a tiny town in Indiana to Harvard Law School, followed by two federal clerkships and partnership at two top law firms. We then discussed how she built her practice in appellate and ERISA litigation, her recent move from Goodwin Procter to Proskauer, and her thoughts on the game of musical chairs now unfolding in the Supreme Court and appellate bar. We concluded by talking about her most meaningful matters over the years, including her victory before the high court in Wilkinson v. Garland, as well as the most interesting cases in the Supreme Court’s upcoming Term and in the world of ERISA and employee-benefits litigation. Without further ado, here’s my conversation with Jaime Santos.
Jaime, thank you so much for joining me.
Jaime Santos: Thank you. I’m excited to be here.
DL: Tell us about your background and upbringing. Where did you grow up?
JS: I grew up in the Midwest, in this tiny town in Indiana called Rensselaer—basically in the middle of a cornfield. I was raised by a single mom with one sibling, and we grew up in a trailer park. When I was 14, we moved to St. Louis, Missouri—the inner city, which is the opposite of a rural Indiana cornfield. My aunt, who lived in St. Louis at the time, basically told my mom, “You cannot raise these children in Indiana with only corn and white people. Move to St. Louis. We will help out, and we’ll get these kids through high school and make sure they have a good future.”
DL: I wouldn’t have guessed that you were from the Midwest because you went to college out on the West Coast and law school out on the East Coast. Do you have any lawyers in the family?
JS: No lawyers in the family. My mom, before I was born, worked in the South Chicago steel mills, and then, when I was growing up in Indiana, she was a bookkeeper for a small printing company. My dad left when I was a year old. So I don’t even know that I met any lawyers until after undergrad.
It was funny: I went to the University of San Diego mostly because I wanted to get as far away from home as possible. When I was applying to schools, I got this beautiful glossy magazine—this is how we used to apply to undergrad—and it had beautiful pictures of the ocean. I applied, immediately got in, and got a full scholarship, so I didn’t apply anywhere else. I thought, “Well, this is the objective: get into college and have someone else pay for it.” And I spent four years there.
DL: What did you major in when you were there?
JS: I majored in ethnic studies, sociology, and Spanish.
DL: And what were you thinking in terms of your career at the time?
JS: I didn’t really know. I thought maybe I wanted to be a professor or maybe I wanted to work for nonprofits. I didn’t do debate or anything like that. I was really involved in student government, the multicultural center, and student leadership. To help pay for things, I also worked a ton through undergrad: I was a sandwich delivery person and a telemarketer, and I worked at the registrar.
I did have this one professor—my favorite professor, Dr. Rafik Mohamed—who taught a class called Sociology of Law. At the very beginning of the class, he taught us, just for a few minutes, how people sometimes write case briefs—the notes that law students keep to track cases and what they mean. We went through the class, and at the end of the semester, I went to his office and said, “Hey, that thing you taught us at the beginning—I decided to do that with every case we read.” I showed him all the notes I’d put together and said, “I’ve noticed a bunch of patterns across cases.” He said, “You’re a weirdo who does this for fun. You definitely need to go to law school.”
I didn’t at the time. I worked for four years after undergrad—as an event planner at a nonprofit, then at a law firm. But eventually I realized he was right, and I really wanted to use my brain. And event planning was fun, but it’s just not a very brainy activity. So I studied really hard for the LSAT, got into Harvard, and ended up going there about four years after I graduated from undergrad.
DL: When you were at HLS, did you have an idea of what type of law you wanted to practice?
JS: Going in, I definitely didn’t, because I was so excited just to be there. Harvard was the one place, when I was growing up, that anyone in my family would have known—other schools, we didn’t know as well. I was the first in my family to go to college; my mom and dad didn’t go, and neither did my grandparents.
I was so excited to go that I completely threw myself into everything; I studied crazy hard. I was afraid I was going to be the dumbest person at Harvard, surrounded by all these fancy people who’d gone to Ivy League undergrads. So I studied nonstop, at least the first two years.
I had more fun my third year. I got onto Law Review, I RA’d for a bunch of different professors, and I took really hard classes. Dan Meltzer had this super hard Fed Courts class—it was a five-credit class that felt like a 20-credit class—and I studied so hard that I literally sprained my neck. I had to get treatment because I sprained my neck studying too hard.
Coming out of that, I thought maybe I wanted to do labor and employment work. But when I was clerking—first on the Central District of California, then on the Ninth Circuit—I realized pretty quickly that I didn’t actually care about subject matter. I just liked complicated issues that were really hard.
Going into the clerkships, I thought, “I probably want to do labor or employment work.” Coming out of them, I thought, “I just want to do nerd stuff.”
DL: Which did you do first, the Ninth Circuit clerkship or the Central District clerkship?
JS: The Central District clerkship, though I actually got my Ninth Circuit clerkship first. I interviewed with Judge Raymond Fisher—I think it was probably in the fall right before my 3L year—and after I got that clerkship, he helped me talk to some district judges as well. Then I went through the normal interview timing process for district court clerkships at the time, which was just the year before graduation. Now it’s apparently the year you’re born—but back then, it was more human.
DL: Yes, I totally agree, and it’s really unfortunate how the timing has shaken out. But it’s interesting that you went to the district court right after law school, because I actually think a district court clerkship is, in many ways, the harder job, and a little overwhelming if you go straight from law school, whereas a circuit clerkship is more like a transition from law school to the practical world. And so that first clerkship must have been a demanding experience.
JS: It was. I clerked for Judge George King, who was then the chief judge of the Central District of California, and he was a particularly demanding judge to work for. He was really smart and really great, and I learned a ton. But we were working 80- to 100-hour weeks, every week, the entire year. It was very demanding.
For Judge Fisher, I think part of why he liked clerks who had clerked on the district court first was that it broke them in—or at least gave them a much better understanding of what district courts were doing, because he liked to defer to district courts on things they did better, and not defer on things that were really classic appellate issues. And I was absolutely a better Ninth Circuit clerk because I had been through the district court clerkship and understood what the dockets looked like and the incredible caseload and what trials looked like and how everything gets resolved.
DL: I totally agree. I think clerks who’ve clerked for a district court before a circuit court are probably less inclined to recommend reversal in everything, because they know how tough that job is and respect the discretion district judges have over so many areas. So I’m sure it made you a better clerk.
JS: I hope so. I don’t know that Judge Fisher would say I was the best clerk; I would often get in trouble for trying to come up with new arguments no one had proposed. One time I wrote a very long memo about Heck v. Humphrey and how the whole case failed. And I remember he wrote at the top of my bench memo something like, “This looks great. Did anyone argue it?” And I said, “No, Judge….” And he said, “Okay, let’s deal with what the parties argued.”
DL: Party presentation: it’s a thing. So you probably felt right at home once you got into practice.
JS: Absolutely. After my clerkship, I joined Goodwin Procter. The timing was funny: I finished my clerkship when I gave birth to twins, who were born a month early—only about seven business days before the end of my clerkship. I felt very bad about that, like I’d abandoned Judge Fisher.
So I finished my clerkship, gave birth to twins, and then twelve weeks later started at Goodwin. It was funny, because Willy Jay—who’s now at Paul Weiss—had just started there maybe the year before. I wasn’t hired by him or into the appellate group at all; I was just hired into litigation generally. I had a mentor at the firm who helped me weasel my way into the appellate group, basically by trying to make myself completely indispensable on any appeal.
When I started, Willy had just hired two recent Supreme Court clerks who weren’t allowed to work on Supreme Court matters for a couple of years. They didn’t really have much of an appellate group otherwise. So once I’d weaseled my way in and shown that I had a strong work ethic and would do literally anything I was asked to do, Willy started putting me on his Supreme Court matters. I also had—at the time, and still have—a raging case of imposter syndrome. I think of it as an asset, even though a lot of people see it as a weakness. It made me really good at my job because it made me question what I was doing, in constructive ways: I made sure that my arguments were airtight, that I researched more, and that I worked harder than other people.
Once I’d shown my value, I got to do more appellate work. I had a turning point around 2015. I worked with Willy on Teva v. Sandoz, a patent case, and I’d also argued two Ninth Circuit pro bono appeals. That work, taken together, left me completely hooked on appellate work, and I knew that was what I wanted to focus on. After the Teva argument, I told Willy that it had almost made me want to apply for a Supreme Court clerkship. He said, “What are you talking about? Why did you never apply?” I said, “I didn’t clerk for a feeder judge, and I just thought I wouldn’t have a chance.” He said, “You should definitely apply.”
So I applied for clerkships, and I got an interview with Justice Sonia Sotomayor. I didn’t end up getting the clerkship, but I spent the last month of my maternity leave with my youngest child basically prepping for that interview. I read the last three years of Supreme Court opinions, I read every opinion Justice Sotomayor had ever written, and I spent a month reflecting on what I wanted to do and where I wanted to go.
When I didn’t get the clerkship, I asked my firm if I could move down to D.C., because I wanted to immerse myself in the appellate world and learn from Willy and build our D.C. appellate practice, if he’d have me. The firm was incredibly supportive; they said, “Absolutely.” I moved a few months later.
Once I got down there, I was facing a bit of a conundrum: I tend to be a Type A, ambitious person, and I really wanted to be the most successful appellate lawyer I could be. But I knew I didn’t have the credentials that a lot of your former guests have—folks like Lisa Blatt, Paul Clement, Easha Anand, and Willy as well. But I really wanted to be good at this and get to a very high level.
So I thought, “You’re going to have to find a different way, Jaime. It’s not the normal path. Supreme Court to OSG [Office of the Solicitor General] isn’t going to work for you, and you’re going to have to find another way to get there.” I spent the next five-plus years trying, on the one hand, to get really good at honing my appellate craft and learning as much as I could, and, on the other, trying to figure out how to raise my profile and expand my network so I could succeed in the long term. You can only go so far being smart and hardworking. In D.C., that doesn’t actually get you very far, and it doesn’t get you hired.
I started doing a lot of public speaking, at law schools and conferences, and talked about anything: diversity in the legal profession, what it’s like to be a working mom, appellate practice. I got the chance to work with a group of current and former law clerks to advocate on issues of judicial misconduct in the federal courts, and then ended up working with a bunch of judiciaries across the country on their own judicial misconduct procedures, and that gave me the chance to testify before the Senate Judiciary Committee and the Judicial Conference. I helped start a podcast. I ended up serving as secretary of the Inn of Court in D.C., which is where the 200 biggest appellate nerds meet once a month during the Supreme Court Term for cocktails and panels. I thought, “This is a ton of work, but it’ll give me the chance to know everyone.” So I did all of these things as my side gig, while also trying to learn to be a really good appellate lawyer.
DL: What you just described is exactly what lawyers who want to build a practice need to be doing—because as you say, and I know it’s a cliché, being smart and hardworking is table stakes. You need to stand out in some other way.
So you were very modest when you said you “started a podcast.” Tell us what podcast that was.
JS: Back in the day, pre-pandemic, I helped start Strict Scrutiny. I was on it for the first year, then left, and it has continued to grow.
DL: It’s now one of the largest, most successful, and most influential legal podcasts—or podcasts, period, anywhere. What led you to leave after a year?
JS: There were a number of different factors. It was never going to be a long-term option for me, in part because when I do something important, I put a lot of work into it. I was spending 15 to 20 hours a week on the podcast, which was awesome. I loved it. I got to know everything about the Court, and I got to talk every week with three other brilliant women. But long-term, there was just no way—unless I stopped sleeping entirely—that I could keep doing that. So that was a piece of it.
The other piece of it is that it’s hard to do what Strict Scrutiny became and also be an effective advocate. Especially toward the end of my tenure, I felt like the tone was a little different than what I was necessarily comfortable with. I love edgy commentary, but if you’re trying to advocate before the Supreme Court, being on a podcast that sometimes takes a mocking tone toward the justices or the advocates isn’t a great idea. It’s also just not my style as much. So I thought that I could do smart, interesting commentary on the Supreme Court in other venues, and it might be time to give it a rest, while continuing to support the people who do that work.
DL: I have a couple of thoughts. First, I’m not surprised that you spent that much time on the podcast. People need to know that we try to make these things look relatively easy, but it takes a lot of work to prepare for a podcast. When I have guests, I’ve researched them, I’ve read their writing, I’ve listened to oral arguments—I’ve done all sorts of things. And for a news-driven podcast like Strict Scrutiny, Leah Litman, Kate Shaw, and Melissa Murray are really busting their tails to follow the news of the day.
On your point about being outspoken or candid, being a law professor is good for that kind of work, because (a) they have tenure—they can afford to be outspoken and don’t have to worry about clients or judges being upset—and (b) law professors work hard, but they have a lot of flexibility. You have clients, and you’re a working parent. So I don’t know how you’d find another 15 or 20 hours a week—unless you stopped sleeping, as you said. So I totally understand that.
You were working hard and dealing with imposter syndrome, and it clearly worked: you wound up being, alongside Willy Jay, the co-head of appellate at Goodwin. How long did you spend at Goodwin? You were there for a good long stretch.
JS: Yes—13 years. I think the last two or three years I was co-chair of the practice. Willy had gone on to become co-chair of the non-IP litigation group at Goodwin generally, and when he moved into that role, I moved into the co-chair role, along with my former colleague Kevin Martin, who’s in Massachusetts. I loved that role. Leadership is just in my DNA—getting the chance to lead the group, help expand it, and instill a sense of business development and proactiveness in everyone. I got to hire people and help promote people, and the group there is really phenomenal. It was a great place to spend 13 years.
DL: You recently made a move. This was certainly in the news, and once again, you have a leadership role too. Maybe you can tell us about that.
JS: Yes. I recently joined Proskauer Rose, straddling the litigation department and the employee benefits practice.
I definitely wasn’t looking to leave Goodwin. I really loved my colleagues, and my practice was growing there. Proskauer approached me through a friend who’s also a recruiter—shout-out to Karen Vladeck, whose lesser-known husband is Steve Vladeck. I’ve known her and Steve since I was on the Harvard Law Review and was the supervising editor for his book review; it’s funny how things come full circle.
So Proskauer approached me. The firm has this really incredible benefits platform, and an important part of my practice on the appellate side has always been ERISA litigation; I made that an intentional part of my practice. Their benefits practice and their benefits relationships are really conducive to the ERISA piece, and they wanted to invest heavily in that space. They also wanted to invest more broadly in their litigation practice. They’ve been building their trial practice, including folks who’ve joined on the antitrust side. My colleague Bart Williams joined from Munger about ten years ago and really turbocharged their trial practice.
So it seemed like a really great match for the two pieces of my practice I’d been building, and it was a super intensive process. I’ve heard of people switching firms in a month or so, and I don’t know how that would work. I spent three or four months interviewing, I visited three different offices, and I probably interviewed with 30 partners. Part of that is the firm wanting to make sure it’s recruiting people who culturally fit, but it was also very much me wanting to get a real feel for the place—because if I was going to leave this nerdy group of people I adore at Goodwin, I needed to feel sure of it.
And so I ended up coming to Proskauer, and I have been here for about a month.
DL: I have a couple of thoughts. First, you picked a great platform. Given your focus on ERISA, employee benefits, and executive compensation, Proskauer is really tops in that substantive area. I’m not surprised you were steered in the right direction by Karen, who’s one of the best recruiters in the industry—and a former law firm partner herself, so she knows the ins and outs.
I’m curious how you developed this additional expertise beyond the Supreme Court and appellate work. How did you come by the ERISA and employee-benefits focus?
JS: When I mentioned earlier that I didn’t have the normal path available to me and had to find a new way to do this, it was around the same time I was trying to figure it all out. I like being a generalist appellate lawyer, because I get bored doing the same thing too much. But on the appellate side, in terms of strategically building a practice, it’s really helpful to have one or two niche areas you know really well; you can market yourself, and you can speak on them.
I remember sitting in my D.C. office thinking, “What do I want my niche to be?” I thought about patent work; there’s a lot of work there. But there were a ton of, for lack of a better term, fancy gray-haired men with lots of credentials who were already the go-to lawyers in the space. Willy is one of them, Seth Waxman another—and no one’s going to hire me over Seth Waxman for a patent appeal. I thought about antitrust; I really like antitrust cases, but the dynamic was the same there. And bankruptcy—Roy Englert is amazing, the bankruptcy appellate god. I liked product-liability work. But Goodwin had largely wound down its product-liability practice, so that wasn’t going to be a good match.
I was going through the specialties, and I came to ERISA. I had done some ERISA cases, and I really liked them—because there’s a combination of administrative law, statutory interpretation, and some common law. It’s also very complicated, and everyone else hates it. So then I thought, “Who on the ERISA defense side is the appellate person?” And there wasn’t anyone; there was literally no one who was the overwhelming ERISA appellate person. On the plaintiffs’ side, there certainly were lawyers like David Frederick, Peter Stris, and Matt Wessler. But they do that work on the plaintiffs’ side, not on the defense side. And I thought, “This is an area where I can really carve out a place, be really good, and get to argue the appeals I lead.”
It turned out to be great for me in the long term, because it’s the one area where I feel I don’t have to fight over arguments or field the question, “Should she be the one who argues?” Even after I’d argued in the Supreme Court and argued en banc in the Sixth Circuit, in other areas, like patent, I’d have clients say, “I think someone with more experience, who’s done more Federal Circuit appeals, might be better.” That doesn’t happen on the ERISA side, because there isn’t someone more experienced—some gray-haired man who’s better suited. I’m the person, and I really like these cases. It was a strategic move that’s been great for my practice and a lot of fun.
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So I just want to highlight the wisdom of your approach. I spoke to a very successful lawyer at the top of their particular niche, and this person told me that when advising law students or young lawyers on choosing a practice, their advice is this. First, find something you’re genuinely interested in; don’t go into something just because it’s hot or trendy. Next, ask yourself whether there’s already a go-to person in that field—someone like Roy Englert or Seth Waxman. And then, if there’s no one who is that person, go be that person. So I guess you went and became that person for your field.
Let me now ask you about another topic. You’re an appellate and Supreme Court lawyer who moved in 2026, so join the club. It seems like pretty much every appellate and Supreme Court litigator moved in 2026. I won’t go through all of them, lest I leave somebody out—but what is up with this?
JS: It’s a very fair question, and I think there are a bunch of things going on. Some people are probably just chasing money. There’s a crazy amount of money kicking around, based on what I’ve heard about what some firms are willing to pay for an appellate practice.
For others, it’s more complicated. There are firms that have been undergoing a massive amount of change over the last ten years, increasing their transactional practice and shrinking their litigation practice. For litigators, and appellate litigators in particular, that can be really problematic. It can create bigger conflicts landscapes when you have big tech practices, especially if you’re representing smaller or mid-cap companies, since that can mean you can’t handle matters for Fortune 100 companies.
And with more of a focus on transactional practice, there’s less high-stakes litigation—and without high-stakes litigation, it’s really hard to have a successful appellate practice, unless you’re Paul Clement and people just pick up the phone and call you. It’s Paul, and Lisa Blatt, and Elizabeth Prelogar, and that’s basically it; there are probably a couple of others, but for the rest of us mortals, it doesn’t work that way. So as firms have changed their strategy, some appellate lawyers have taken a hard look at their practices and asked, “Is this really the right platform for me, or might I thrive somewhere else?”
And maybe the other piece is that if you look back 10 to 15 years, that was when you started to see litigation practices think, “I need an appellate practice to support my litigation practice—I’m losing pitches because we don’t have a good litigator here.” So a lot of people joined appellate practices 10 to 15 years ago, including Willy, and they might just want a change now. When you’ve been at the same place for a long time, you might just want a new experience. If you enjoy building a practice, you can start to feel antsy being part of one that’s already built—and that’s also a good reason to try something new.
DL: Looking back over the course of your career as a Supreme Court, appellate, and ERISA and benefits litigator, is there a particular matter you’re most proud of? I have one guess in my head, but I’ll let you tell us.
JS: I’ll give two—one appellate, one ERISA. The appellate one is probably obvious: I argued Wilkinson v. Garland in the Supreme Court a couple of years ago, on behalf of an immigrant, Situ Wilkinson, who was seeking relief from deportation under the cancellation-of-removal provision of the INA [Immigration and Nationality Act]. He was arguing that his removal would cause serious harm to his minor son, a U.S. citizen, and that he should therefore be allowed to stay in the United States. The Third Circuit had held there was no jurisdiction to review the immigration agency’s decision. We convinced the Supreme Court to take up the case, and it reversed.
There were a couple of reasons it was meaningful. The obvious one is that it was amazing to be entrusted by Situ to argue a case where his life and his family were on the line. You’re probably aware of this, but there are so many budgetary pressures in law firm practice that sometimes it feels like you’re just trying to get words on paper while spending as little time as possible. Getting to litigate a case the way I really wanted to—chasing down every thread, going down every rabbit hole, reading every case on the subject—is just a fun way to litigate, and I don’t get to do it that often.
It was also very meaningful because my family was there, and my mom came out from St. Louis to watch me argue. I talk to my husband and kids about my work, but I don’t really talk to my growing-up family about my work that much. I think part of it is that when I was growing up as a poor kid, people didn’t really talk about their jobs; you usually didn’t enjoy your job that much. It just wasn’t part of the culture I grew up in. And my work is complicated, technical, and not particularly intuitive, so I don’t talk to my mom much about what I do. But she could come out to the Supreme Court and completely understand the gravity of what I was doing, and having her there was a real point of pride.
Two of my three kids came. (One said, “That sounds too boring, Mommy, I’d rather go to school,” and went to school instead of watching me argue.) One of my kids got in trouble at the Court for trying to lie down on my husband’s lap, and she was told that wasn’t allowed. I remember thinking to myself, “You don’t wake up the justices when they fall asleep—why Emily?” So that was very meaningful to me.
The other reason it was meaningful is that I was proud to have gotten this coalition of justices. You have to count to five, and in an immigration case, that can be hard. But we got all three of the justices appointed by President Trump, plus Justice Kagan and Justice Sotomayor, to combine on this majority opinion. It goes to show that if you find the right case, make the right arguments, and do it with care, you can prevail. And I made sure to involve immigration advocates at every stage of briefing and at every moot. I don’t think it’s fair or just or right to take a case up to the Supreme Court that you have no chance of winning on behalf of a marginalized population, just to get an argument. I would never do that. I think it’s problematic, and I know some members of the bar do it, and I’m completely against it. But this was a case we really thought we had a chance at winning. We could make a good textual argument, we had good precedent, and we thought we could build a coalition. And we did, and it created good precedent nationwide.
DL: And what was the trial court matter?
JS: I’m going to anonymize it a bit, because it’s a case that’s still pending, but it’s an ERISA case—part of a series of cases that have gone almost 100% against ERISA defendants. There are something like 70 or 80 cases in this genre, and on almost every issue raised, courts have ruled in favor of ERISA plaintiffs. I see that pretty often in ERISA cases: you get one decision, and then another district court thinks, “I hate ERISA cases… This judge said this, I’ll go along with it.” It gathers steam, and everyone just keeps citing the original case.
There was an associate at my prior firm, Isabel Marin, who is awesome, and she and I basically crafted these arguments—really just administrative law and standing arguments that no one had started briefing when we started working on these cases. We went into court and told the judge, “We know that 25 courts have ruled against us, but these are really good arguments. Most of them weren’t raised, and if they were, they were poorly briefed; you can see it in the decisions, which say things like, ‘This issue was raised, but barely briefed.’ Please just take an independent look at this.”
We won an across-the-board decision, with the judge going against a wall of adverse authority: 100% of courts had gone the other way on Article III standing. I felt like it was a situation where the quality of the advocacy actually made a difference. Sometimes you don’t feel like it matters, but this time it really felt like it did. And even though it was an ERISA victory, it felt just like a normal appellate, ad-law, constitutional victory.
DL: That’s a great example. So much of lawyering comes down to creativity and to seeing arguments that haven’t been raised before.
I can also understand how amazing it must have been to have your mother in the audience when you argued Wilkinson v. Garland. It probably wasn’t easy for her as a single mom, and I got a bit of a chill or shiver as you were just telling me about how meaningful it must have been for her to watch her daughter argue before the highest court in the land.
Speaking of the highest court in the land, we’re recording this shortly before the start of the upcoming Supreme Court Term. Just an hour ago, I finished presenting on a CLE panel previewing the Term. For listeners who don’t follow the Court as closely as we do, what would you identify as some of the biggest cases or cases worth following?
JS: There aren’t a lot of high-profile cases that have been granted yet for this Term, but I always say that in September, and then the Court goes and grants a billion cases that give me heartburn. I think the Court is also leaving room in its docket for election cases this fall, in case they come up.
Probably the biggest case I’m keeping an eye on is the Suncor Energy case, which is about whether litigants can use state tort law to sue companies that have contributed to climate change. It’s interesting because, from my read, the defendant below was really trying to rely on general federal preemption principles—the idea that federal law, whether common law or statutory, supersedes state tort law. But the Supreme Court right now really does not like anything that starts with the word “implied”: implied private right of action, implied preemption, implied remedies—it’s a no-go. So the defendant has had to shift the argument toward a more constitutional, separation-of-powers argument, and it’ll be interesting to see how the justices come out on this and how principled the decision is. That’s one I’m keeping an eye on.
Another one—I call it the “Blockbuster Video bandanas case,” which isn’t what it actually is—it’s a case about the Video Privacy Protection Act, the statute passed many years ago so that Blockbuster couldn’t secretly reveal that George Clooney really liked binge-watching Teletubbies. It kept companies from disclosing people’s video-watching history, but the statute is written broadly enough that it could plausibly cover any transaction for any goods or services by a company that puts videos online. Think Home Depot self-help videos—my husband watches those all the time. Does this VPPA statute mean Home Depot can’t disclose that he bought a humidifier last year? I don’t know. The plaintiff says, “Yes—look at the statute, those words are on the page.” The defendant says, “What are you talking about? That’s not what the statute was meant to do.”
I think this is another case where the Court’s commitment to textualism versus contextualism is really going to be tested. I kind of believe the Court is textualist until it is not, and then you get this purposivism that masquerades as contextualism. Or maybe it’s just a better way of taking a look at the bigger picture, while still operating under a textualist method. But in both of these cases, I’ll be curious to see how principled the decision is.
DL: I totally agree with those picks—those are two of the most interesting cases. My husband Zach is the executive editor of SCOTUSblog, and he and I have gone back and forth on Suncor, because as a policy matter, you can understand why…
JS: It’s crazy, there’s no way…
DL: … you don’t want state or local officials being able to go after national or multinational companies. I understand that. But what’s the hook? As you mentioned, the Court doesn’t like anything “implied.” So what’s the concrete textual hook for ruling in favor of the companies? I don’t know; we’ll see. It’ll be interesting.
And on the VPPA case, this is the statute that was passed around the time of the Robert Bork nomination, when someone leaked his video-rental history—which had nothing scandalous in it, but people didn’t like the fact that it had been leaked. Doesn’t this case involve the plaintiff being served ads based on their viewing? We’re all served ads based on what we watch; it’s just a fact of modern life. So that’s an interesting one too.
JS: Yeah, it’s a question of how you deal with a statute that clearly wasn’t aimed at this, using this textualist approach the Court is taking. I could easily see a decision where the Court says, “Those words are on the page. Congress can amend it.” That also seems kind of insane as a policy matter, but maybe that’s just a policy issue.
DL: Are there any cases that you would mention or identify as sleeper cases, some important cases that are on the docket for the Court but maybe not getting the buzz they deserve?
JS: So there are two cases. One is a case my former colleague, Will Evans, who’s amazing and wonderful, is arguing: Montoya Palacios v. Liggins. It’s about EAJA fees—Equal Access to Justice Act fees, which a prevailing plaintiff who sues and wins against the government can generally recover, as long as it’s not a tort case and as long as certain standards are met.
Does EAJA apply in habeas cases? They’re technically civil cases, but they don’t always feel very civil all the time. This is a really important case right now, given all of the immigration raids the administration has been conducting—habeas has been the only avenue for relief in many cases. Even the government has said, in some instances, “You can only do this through habeas; you can’t bring a class action, you can’t bring an APA lawsuit.” Many of the groups doing this work are civil-rights organizations, nonprofits, or solo practitioners—teeny tiny little practices. So if they can’t recover EAJA fees when they win, even when the government wasn’t justified in its actions, it’ll be really hard for them to take on this work.
And the availability of EAJA fees affects what the government does in the first instance. When our client, Situ Wilkinson, was in immigration detention—he’d been there for years—we filed a habeas action to try to get him a bond hearing, which he’d been denied. The government, when we filed, agreed to release him as long as we agreed not to seek EAJA fees. I don’t know that he would’ve gotten out if there hadn’t been that risk of EAJA fees; why not just keep litigating? So it affects primary conduct, and it’s certainly important to the work immigration lawyers are doing.
DL: And then you mentioned there was maybe one other matter you wanted to highlight.
JS: Yes—there’s an ERISA case, obviously, which is the most important case of the Term. Luke McCloud, my friend from law school, is arguing it: Andersen v. Intel. It’s about what an ERISA plaintiff needs to show, when challenging an investment-plan lineup in a retirement plan, to state a viable claim. It’ll probably bore a generalist audience, but the Supreme Court granted cert in a similar case a few years ago, Hughes v. Northwestern University, and kind of punted on this issue. So I’ll be curious whether the Court digs in this time.
My experience with ERISA cases at the Supreme Court is that it usually writes very short, unanimous opinions that don’t really say that much. Maybe the justices are bored, or maybe they’re just worried about getting that area of law wrong. I’ll be curious whether they actually dig in, or just issue another very short, nine-page unanimous opinion from Justice Sotomayor.
DL: Well, it’s funny, I feel like ERISA is almost like a sleeper topic. It’s vitally important, but it doesn’t get as much attention as I think it deserves. And full disclosure, I’m something of an ERISA nerd myself. For those of you who aren’t familiar, it’s the Employee Retirement Income Security Act of 1974. I took ERISA in law school, I later worked with my professor as a research assistant on his ERISA casebook, and my father-in-law is a pension actuary—so I actually have this weird interest in ERISA.
So I’m curious—I’ve had more than 100 guests on this podcast, including a number of Supreme Court and appellate advocates, but you’re actually the first ERISA and employee-benefits lawyer I’ve had on. Besides what’s happening at the Supreme Court, what’s an issue that’s really on the minds of ERISA lawyers right now? It doesn’t have to be something on appeal. What’s an issue in the trenches that some of your clients are concerned about?
JS: Historically, over the last 15 or 20 years, most ERISA litigation—the class action litigation I focus on—has been on the retirement-plan side. And there’s been a recent push toward health-plan litigation. I think that creates an enormous amount of risk for employers who sponsor health plans, because those plans are incredibly complicated. They often involve hundreds of millions of dollars—a lot of it employer money, since employers are often heavily subsidizing health plans—and a lot of people don’t understand them at all. So a plaintiff, or a plaintiff’s lawyer, can come in and wreak a lot of havoc without really understanding how things operate, and make things look very factually complicated. I’ve seen a number of health-plan class actions over the last couple of years starting to wind their way through the courts.
On the ERISA appellate side in particular, the areas most interesting to appellate courts, and especially the Supreme Court, are a bit like patent law—where you find something that’s ERISA, but not too ERISA. Think of where ERISA intersects with Article III standing or with class actions. There’s a bunch of issues percolating about the standing of plan participants who claim there was some violation of ERISA but can’t show they would have been in any different position even if ERISA had been complied with.
There’s also an issue winding through the courts about whether you can certify a mandatory, no-opt-out class of ERISA plan participants who are seeking money. For basically 15 years, courts almost uniformly said, “Yes, absolutely, a non-opt-out class is fine.” The Fourth Circuit recently said, “Wait—no, that’s a Rule 23(b)(3) class. You can’t do that.” It was the first court to go against this wall of authority, and I’ve already seen that issue pending in one other circuit.
So those are the kinds of issues I think can reach the Supreme Court despite being ERISA cases.
DL: Do you think that that last issue is going to result in a split perhaps?
JS: Absolutely. I think it’s only a matter of time.
DL: Interesting—well, I hope you’re the one to argue it.
So, turning 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 be the practice of law, or law as an abstract system.
JS: It’s probably somewhere in between the two: I really dislike the purity test that exists right now on both the conservative and progressive sides of the legal world. I’ve gotten a lot of flak from the progressive movement for… I have a lot of friends who are conservative lawyers or judges, and I sometimes have views that diverge from the left side of the political spectrum. I think that’s a good thing; it’s good to maintain relationships with people who feel differently from you. But I think there’s a sense right now that if you don’t violently agree with everyone in your ideological tribe, you’re a fraudster or a sellout.
I’ll give just one example of this. I remember when the SEC v. Jarkesy case came out a Term or two ago, and it was about whether the SEC could do in-house adjudication of claims for civil penalties instead of going to court. And I remember reading through the majority opinion, and I called a friend of mine and I said, “Okay, so quick question. I’m a progressive, so I know I’m supposed to hate this, but why? Don’t progressives like due process? Don’t we like access to courts? Do we really like immigrants being subject to in-house adjudication where the Department of Justice and DHS are the judge, jury, and prosecutor? Absolutely not. And so why would we like it for the SEC?”
So I feel like that kind of thinking can paint you as a pariah, and I don’t like that—and I know it happens on the conservative side, too. And I just wish we could be a little bit more open-minded and listen a little bit more.
DL: I totally agree with you there; you’re preaching to the choir. My second question is, what would you be if you were not a lawyer?
JS: So I would like to say an adventure tour guide, because I mentioned I’m an adrenaline junkie. When we go to Disney World with the kids, I’m the roller-coaster parent; my husband is the hold-the-bags parent. But realistically, I probably am too risk-averse for that. So maybe a baker? I really love baking. I like the precision. I like the creativity. I like that you immediately know if you have succeeded or failed, instead of having to wait a year for an opinion after argument. So maybe a baker.
DL: I’m with you on the baking. I like the precision. I do not have the judgment or discretion to be a cook and say, “Oh, I’ll throw in a little more of this or that.” With baking, if you follow the recipe, it works.
JS: Exactly, exactly.
DL: My third question is, how much sleep do you get each night?
JS: Currently, I probably average about six to seven hours a night, which is not too bad. It has gotten better. My first four years out of law school, I was averaging probably two to four hours, which is awful, but part of this was I had newborn twins who did not sleep, and I was practicing, and that was really tough, and I had demanding clerkships.
But more recently, I really need more sleep. As I get older, I really, really, really need more sleep. One thing I’ve noticed is that the time I go to sleep matters sometimes more than the amount of sleep I get. So if I go to sleep at 1:00 a.m., my sleep is trash; it doesn’t matter how much I try to get. If I go to sleep earlier, I’m in a much better situation.
Before argument, I prioritize sleep over everything, because I definitely notice that I am sharper and I can use my brain more efficiently when I have better sleep. So the two nights before argument, I always try to get at least eight hours of sleep, and my Friday night fun is to try to go to bed at 9:00 p.m.—that’s my favorite thing ever.
DL: Well, getting good sleep before an oral argument is good advice, and that brings me to my last question: any final words of wisdom, such as career advice or life advice for my listeners?
JS: Sure—so maybe two, but I might come up with a third by the end. The first is to be kind. I think this is going to sound too Pollyannish, but kindness for me is one of the most underrated characteristics that people have. And for my part—especially living in D.C., where everyone is smart and hardworking—I am so much more impressed by people who treat each other well than by someone who is super smart. And I’m talking about being kind to everyone—not just the people above you, but judges, their clerks, the staff, the leaders of your group, the IT people, the TSA agents—saying thank you, just being kind. If you are kind to people, they will have your back, they will be loyal to you, and when you make a mistake or say something stupid, like I do all of the time, they will forgive you and be understanding. So number one, be kind; that’s my governing principle.
The number two piece of advice is to try to focus more on raising other people up than yourself. There are so many people, in D.C. especially, who are just always focused on promoting themselves. And in my experience, if you focus on promoting other people and what they are doing—whether it’s making your client look good, making your colleague look good, making a junior lawyer look good, making a friend look good—you’ll be happier, other people will do better, and then the universe just kind of has a way of making sure it works out from a karma perspective. So try to help other people instead of yourself.
And then maybe a third one is, “There’s always a way.” There’s a way to do what you want to do, and you just have to find that way. I remember saying, after I did not get the clerkship with Justice Sotomayor, “Okay, this door is closed, so I have to do a little light breaking and entering and find a crawl space or break a window.” There’s always a way to do what you want to do. It might not be immediately apparent, but I try to find a way. If I have a bad day or a bad argument or get a bad decision, I let myself have 24 hours to sulk, and then I have to get myself up and figure out what to do. So take your 24 hours and then get your butt up and start figuring out another option.
DL: Well, you have definitely found a way to have a fascinating and really inspiring career. Jaime, thank you so much for joining me.
JS: Thank you. It was really fun.
DL: Thanks so much to Jaime for joining me, and congratulations to her on joining Proskauer.
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