Depositions are a crucial part of discovery—and they can also be, in the hands of a talented litigator, torture for the witness. So I suspect that many lawyers on the left—and beyond—might be jealous right now of Roberta “Robbie” Kaplan, the iconic lawyer and founding partner of Kaplan Hecker & Fink (“KHF”). Last month, Robbie had the pleasure of deposing former president Donald Trump—not once, but twice.
I’m guessing it wasn’t a fun experience for the Donald. His niece Mary Trump, who hired Kaplan Hecker to sue her uncle for fraud, described Robbie to Bloomberg as follows: “She’s brilliant, she’s unrelenting, she can’t be intimidated, and she’s not going to back down. She eats bullies… for lunch.”
Deposing the president twice in the same month is only the latest distinction for Robbie, known for handling some of the most high-profile and high-stakes cases in the country. She’s most well-known for representing the late Edie Windsor in United States v. Windsor, the landmark gay-rights case in which the Supreme Court held unconstitutional section 3 of the Defense of Marriage Act. But Robbie is also the lawyer of choice for major corporations like Goldman Sachs and Uber, who hire her and KHF to handle their most complex legal problems.
On Monday, I was delighted to speak with Robbie for the fourth episode of the Original Jurisdiction podcast. She wasn’t able to say much about the Trump depositions, but she did talk about her multiple cases against Trump in broader terms. We also spoke about what makes her unique as a litigator; her epic victory last year in Sines v. Kessler, in which she won damages of more than $25 million from the white supremacists behind the violent “Unite the Right” rally in Charlottesville in August 2017; her vision for Kaplan Hecker & Fink, the thriving litigation boutique she founded after more than two decades at Paul, Weiss; free-speech and cancel-culture controversies in the legal world; and whether she’s a tough boss.
Please check it out by clicking on the embed at the top of this post. Thanks!
Show Notes:
Roberta A. Kaplan bio, Kaplan Hecker & Fink LLP
Then Comes Marriage: How Two Women Fought for and Won Equal Dignity for All, Amazon
A History-Making Litigator Leaves Biglaw To Launch A Boutique, by David Lat for Above the Law
Roberta Kaplan Builds Progressive Firm Suing Trump, Defending Wall Street, by Erik Larson for Bloomberg
2020 Attorney of the Year: Roberta Kaplan, by Jane Wester for the New York Law Journal
Lady Justice and Charlottesville Nazis, by Dahlia Lithwick for Amicus/Slate
Prefer reading to listening? A transcript of the entire episode appears below.
Two quick notes:
This transcript has been cleaned up from the audio in ways that don’t alter meaning—e.g., by deleting verbal filler or adding a word here or there to clarify meaning.
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David Lat: Hello, and 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 by going to davidlat.substack.com.
You’re listening to the fourth episode of this podcast, which airs every other Wednesday. Today I’m honored to be joined by one of the nation’s most celebrated, successful, and significant litigators: Roberta “Robbie” Kaplan, founding partner of Kaplan Hecker & Fink. She is most famous for winning United States v. Windsor, the landmark case in which the Supreme Court held unconstitutional a key provision of the Defense of Marriage Act, paving the way for nationwide marriage equality a few years later. But she has worked on many other fascinating cases over the course of her career, including two pending cases against Donald Trump in which she deposed the former president—twice in the past month.
Robbie was born in Cleveland and grew up in Ohio. After graduating from Harvard College, magna cum laude, and Columbia Law School, Robbie clerked for Judge Mark Wolf of the District of Massachusetts and the late Chief Judge Judith Kaye of the New York Court of Appeals, the state’s highest court. Robbie then practiced for more than two decades at the major law firm of Paul, Weiss, where she built a thriving commercial and pro bono practice, including her big win in Windsor.
In 2017, Robbie left Paul Weiss to launch Kaplan Hecker & Fink (“KHF”), one of the nation’s top trial boutiques, known for handling both complex commercial and white-collar cases and landmark public-interest matters. One of the first such cases filed by KHF was Sines v. Kessler, a high-profile lawsuit under the Ku Klux Klan Act of 1871 against twenty-four neo-Nazi and white supremacist leaders responsible for organizing the racial- and religious-based violence in Charlottesville in August 2017. That case went to trial, and a year ago this month, the jury awarded a total of more than $25 million to Robbie’s clients.
In our conversation, Robbie and I talked about her various Trump cases, how she knew she was destined for a legal career from a very young age, two qualities that have made her so successful as a lawyer, how KHF has managed to be so financially successful while also doing so much public-interest work, and her vision for the firm’s future. Without further ado, here’s my interview of Roberta “Robbie” Kaplan.
DL: Thanks so much for joining me, Robbie—it's an honor to have you!
Roberta Kaplan: It's a pleasure to be here.
DL: To start with what's in the news—and I feel like you're always in the news—what can you tell us about your latest high-profile case, namely, E. Jean Carroll's lawsuit against former president Donald Trump? I know that you recently deposed him. Is there anything you can say either about the deposition specifically or about the litigation more generally?
RK: Sure. We actually have two litigations that are very active against Donald Trump, and I actually deposed him in both, on two successive weeks. So it was a relatively exhausting period for me. I literally went to Mar-a-Lago two weeks in a row to depose him. That's about all I can say about it, in terms of the depositions themselves.
But in terms of the cases, it's very interesting. The E. Jean case, which you asked about, is on the fastest track. Right now, trial is scheduled to happen on February 6th. Right now we have one case against Donald Trump for the defamatory statements he made in June 2019. That case is currently certified to the D.C. Court of Appeals as to the question of whether when he made those statements, he was acting within the scope of his employment as president—sounds like kind of a crazy question, but that's the question. And the D.C. Court of Appeals, I believe, recognizing the need for speed here, has scheduled that case on a very, very expedited schedule, with oral arguments to be on January 10. So I think it's entirely possible that we have a ruling from the D.C. Court of Appeals before the trial before Judge [Lewis] Kaplan starts.
Even if that's not true, however, we have a second case that we've told everyone in the world, including Judge Kaplan and Trump's lawyers, that we intend to file on November 24, which is the first day we can file it. That is a case directly for battery, the common-law cause of action by E. Jean against Donald Trump, based on a new law that was passed in New York called the Adult Survivors Act. It’s patterned on the Child Victims Act, and it gives people who were survivors of rape that happened a long time ago basically a free one-year period to bring claims, notwithstanding statutes of limitations. That case we're definitely bringing out November 24th, and I don't think anyone will be surprised to learn that we probably will add to that case some new defamatory statements that Donald Trump made on Truth Social against our client—again, none of which are subject to any Westfall Act issue at all, because he wasn't president when he made them.
So big picture, it's highly likely, particularly given the judge we have—Judge Kaplan, no relation—that we will go to trial on all or at least some of those claims in February.
DL: Wow.
RK: And the new case shouldn’t really delay anything because it's basically the exact same facts. As we told the court, the only thing that's different about the new case is the damages theory, so we will have different experts. You obviously have different damages for being raped than you do for defamation. But that's really it. Everything else has already been done in discovery. Fact discovery is closed, and I see very little reason for any additional fact discovery, again, because the facts are totally overlapping.
DL: So what are the two depositions? What was the difference between the two depos?
RK: The first deposition, which happened the week before, was in our fraud case. Before Judge [Lorna] Schofield in the S.D.N.Y., we have a nationwide class action, on behalf of people who invested—I'm using the word “invested” in quotes—in a business opportunity—I'm using “business opportunity” in quotes too—that Donald Trump endorsed and heavily promoted before he was president, known as “ACN” or “American Communications Network.”
It's a multilevel marketing scheme—I don't think even they deny that—in which people pay $500 or $1,000 to become part of this opportunity. Then the goal is to sell video phones. The idea of selling video phones when Skype and other software was already heavily in use—not really the smartest idea in the world—and when I say video phones, I mean big, standard-looking video phones, like I haven't seen since I was a young associate, probably.
The only way to make money as part of this multilevel marketing scheme is to recruit other people in it. You don't make money from selling the phones, you make money from bringing other people in, which is the classic hallmark of a multilevel marketing scheme. Trump was paid a lot of money, at least $11 million or so, from this entity over a period of years. He went to conventions where these people were recruited, and he had huge crowds going nuts for him that kind of looked like his conventions now, honestly. And he said it was the greatest investment he's ever heard of, he did tons of due diligence, he knew it was a great company, a great business opportunity, “people think I do this for the money, but I just like being here.”
I gave you a sense of the kind of the statements he made, and we allege those were all fraudulent, in that they were untrue and he knew them to be untrue. In that case too, fact discovery is closed—there are a couple of exceptions that the magistrate judge ordered, but it's essentially closed. But in that case, given how much bigger the scope is, we are about to go into expert discovery and then class certification. So that case is behind the E. Jean Carroll case for those reasons, although we're very eager to try it before the next presidential campaign for sure.
DL: Oh, interesting.
RK: Because we don’t want to lose our defendant.
DL: Indeed. Totally, totally.
So to rewind a little bit… as I know from having read your wonderful memoir, Then Comes Marriage, you knew from an early age that you wanted to be a lawyer. What can you tell us about your childhood or your upbringing that might have shed light on your future career or that shaped your career choice as a lawyer?
RK: When I was a kid, I liked to talk a lot. I still do. I spent a lot of time with my maternal grandmother, who was a very wise, very smart person. And there's a famous story in my family that when my uncle was in the Peace Corps in India at the time, and there is a series of letters between my mom, my grandmother, and my uncle from India, and in those letters—we still have copies—my grandmother is talking about how I just keep talking all time, and how at one point she said to me, ‘Robbie, you know I love you, but can you just be quiet for like three minutes? Can you stop for three minutes?’ And I said something like, ‘No grandma, I can't. I just can't help myself. I love to talk.’
DL: Ha!
RK: And at a certain point, at a pretty young age, because I liked to read, I realized that if you're a lawyer, you got paid to talk. And I was like, “Okay, that's the job for me!”
Then Sandra Day O'Connor—this is going to show my age, but she was made a Supreme Court justice, I believe when I was in high school. And that had a big impact on me at the time, because prior to that I don't think a lot of women thought they really had—not that I wanted to be a Supreme Court justice, but after that [women] thought they really had a future in the law. I remember that to this day, when that happened, what a big thing that was.
And I just told everyone that I'm 85 years old….
DL: Did judicial office ever cross your mind? Was that something you might have been interested in, in the past?
RK: I certainly have a lot of friends who are judges and I admire what they do, and I think it's a great job. But I like to be a fighter. I like to be an advocate, and obviously I can't do that as judge. I think I would find it too quiet probably for my taste, even at the district-court or trial-court level. But there's no question that more and more we need great judges, and it's probably the single—at least in my job, in my world—the single most important job anyone can have. The only legal philosophy that ultimately works for me is legal realism, which means that often how a case goes—the pace of the case, how it flows, and ultimately what the result will be—is going to be based not only the philosophy but also the life experiences and understanding of the judge. That's just crucial. So the more people who are people of high character and great experience become judges, all the better.
DL: I totally agree with you, totally agree.
Looking at your remarkable career as a lawyer, what would you say is your superpower that is unique to Robbie Kaplan? Obviously, we know about how hard you work and how much you prepare, and of course your tactical brilliance, but is there something you would regard as a little different [about yourself]?
RK: So I have a son who's now 16, but when he was little, one of his favorite books that I used to read, hundreds if not thousands of times, was called Dog with a Bone. And I think the reason I liked that book so much probably said something about me, which is that, as a lawyer, I really am like a dog with a bone.
I do not give up as a lawyer. Our firm doesn't give up. And if I don't succeed on something the first time for a client, I succeed the second or third time, and it's that stubbornness maybe—stubbornness isn't usually considered a good quality, but it's that ability to keep on fighting, our resilience, that is our number-one quality.
Then I'd say, second, creativity. I'm the least creative human being on the planet. I can't draw. My son goes crazy if I try to sing in the car because I'm so off key. I could never do creative writing. My pottery teacher basically kicked me out of class in high school because he asked me why every single pot I made look like a bong. And I wasn't even trying to make a bong! I was like, “I don't know what you mean!” So I have no artistic talent. But to the extent I have any creativity at all, I apply it to cases and the law, and how to achieve what we want to achieve for our clients in a creative and often unusual way.
DL: That makes me think of the Charlottesville case, and your case against the individuals who caused such violence there and how you used a very old statute that was designed to be deployed against the Klan to go after these white supremacists, which was quite brilliant and creative. How did that theory come to you?
RK: We saw what happened in Charlottesville, and we knew something had to be done about it. We were very concerned—and my firm had four people at the time, four lawyers—we were very concerned that the Department of Justice, then headed by Jeff Sessions, was not going do anything. Which we turned out to be right about.1
Pretty quickly after Charlottesville happened, someone got into the Discord servers that the organizers used and leaked a whole bunch of messages. This made it very clear that this was a conspiracy. So okay, great, we have the facts, we have clients, we went down there—but what law do we use? And there's not a lot, frankly, of current law to deal with this, in part because no one—I hope we're not going back to those times—but at least in my lifetime up to now, no one ever thought this was a huge problem. No one ever thought that we would have private conspiracies that were racially motivated, that planned, promoted, and engaged in violence. That may be changing, and that's one of the most disturbing things about our country right now, but that's generally been true for decades and decades.
We had to go back and look for a statute called the KKK Act of 1871, which was passed to do exactly what it says it was passed to do, which was to try to curb the growth of the then-new Ku Klux Klan in the Deep South. Arguably it didn’t have great success in that regard, but there were cases in the 1870s when it was passed trying to curtail or slow or stop the growth of the Klan.
When you think about what happened in Charlottesville, though, it really is the modern-day version of what that Reconstruction Congress was trying to deal with. Back in the 1870s in Alabama, mostly men would don white robes and white hoods, and they would meet in the forest, and they would plan, tragically and horribly, a lynching or whatever they were going do.
Today it's much easier. All you need is a hashtag on Parler or Discord or one of these dark websites, and it's like whack-a-mole—the minute one of the sites stops hosting these people, another one will take over. So all you need is a hashtag—that keeps your anonymity for the most part, unless you self-identify in your hashtag—and you don't have to go into the woods. Literally the guys who organized Charlottesville are from all over the country, and they all were able to plan nationwide and even internationally.
When we filed the Charlottesville case—this is going to show how naive I was—I thought it was a terrible one-off, but it was a one-off, and we needed to bring the case so that it would never happen again. How wrong, in humility, I have to say I was, because not only was it not a one-off, it was really a harbinger, a kind of a road map to a lot of what has happened since then. Even this guy who attacked Nancy Pelosi's husband, while there weren't 20 guys who went to the house, everything that he believed and everything that he was motivated to do was based on these same kind of dark-web, white-supremacist, violent channels, which again, if you're interested or if you're a lonely guy who's looking for a community, it's pretty easy for you to get online and get indoctrinated in their thinking.
DL: Absolutely. And I know this is perhaps a little far afield from your work as a lawyer, but maybe just even as a concerned citizen, how do we deal with this problem? How do we get ourselves out of this? It seems that it's just getting worse and worse.
RK: I wish I knew. It's something I think and worry about all the time. We obviously—and I'm as committed as anyone to the First Amendment—we obviously have a right to free speech in our country, and we should have a right. But it may be both with the [Communications] Decency Act and with the case law, the developed case law in the First Amendment context, maybe [it] does not make sense in the modern day. For example, under Brandenburg, when you're doing something that wreaks havoc in a crowded theater, that may be translatable to things that people do online today in the dark web almost every single day. And whether our standards need to change to deal with that is a very, very serious question. Of course, whether or not this Supreme Court as currently constituted is open to hearing any of those arguments, I don’t know.
DL: That's very interesting. I wonder—because there are definitely some conservatives out there who want to revisit First Amendment doctrine as well—I wonder if this might be some weird area where maybe you agree with some of them?
RK: We obviously have separation of church and state, though I'm a religious Jew, and Judaism going all the way back to the destruction of the Second Temple, in 62 AD or 66 AD, has been obsessed with speech. It's obsessed with speech because it understands that a lot of the damage that people can do to other people is through speaking. If you look at history, there's no question.
Now, I'm not saying that we give up our right to free speech. It's embedded in our Constitution for good reason, and it came out of a world where people were severely restricted in what they could think and what they could say. But the link between certain kinds of speech and violence at this point is uncontroversial, and how we deal with speech that may not be committing violence, but is no question prompting and encouraging and invoking other people to commit violence, is a very serious issue.
DL: Let me ask you this then, and again, perhaps I'm going a little bit out of what you usually focus on as a civil-rights, public-interest, and commercial litigator, but what is your take on what's happening to free speech in U.S. law schools right now? Because there have been speakers who have been shouted down, conservative speakers mainly, but of course, obviously conservatives have no problem going after free speech in other areas.
What are your thoughts on that? Do you share the concern that certain speakers might come to law schools and inflict what activists call “harm” on students?
RK: What I know about this, David, I mostly know from following your column, so that's basically the limit of my knowledge because I've been super-busy lately, but I have the general gist because you're a good journalist and I follow what you write. People have a right to protest. They should. But they don't have a right to protest in a way that stops other people from speaking.
And there's no question that on both sides in our country right now—in fact, both the radical left and the radical right are looking more and more similar every day, which is petrifying because that's what it looked like in Germany in the thirties. So it's petrifying, but people both on the radical right and in the radical left who want to deprive other people of the ability to speak is not acceptable. It's not what the Founders meant. Speech and debate and discourse—even going back to Jewish law—is something to be highly encouraged. And we all make the situation worse, honestly, when we—I hate to use this expression, but when we cancel other people from expressing their views.
Just because you don't agree with someone—I'm sure you and I don't agree on everything—doesn't mean that we shouldn't discuss and debate and argue with each other, and it's terribly distressing because it leads to the kind of breakdown in civil society I think that we're seeing today. And that's also incredibly scary.
DL: Related to these cancel-culture controversies, what are your thoughts on the extent to which advocates can or should be held accountable for their clients? Even though you are most known or most famous for your civil-rights work, your public-interest work, you also represent Goldman Sachs, Airbnb, large companies, and there have been some on the left who have taken this sort of purist approach: “Oh, well, you represent all these progressive causes, but then you represent all these evil companies and defendants and what have you. “ So what are your thoughts on that, the extent to which lawyers should be held accountable for the sins of their clients?
RK: I don't think lawyers should ever be held accountable for the sins of their clients. That's what lawyers do, and if lawyers were in any way held accountable for the sins of their clients, then we wouldn't really have a legal profession. The only exceptions to that would be when lawyers commit the sins of their clients as part of their representation, and that's where, for me, you can't cross the line. I think every lawyer I know weighs these things differently.
Let me begin to say, I don't acknowledge for a second that Goldman Sachs or Airbnb or any of our other clients…
DL: I'm playing devil's advocate—I have nothing against them personally….
RK: … are evil or do anything evil or anything like that.
You have to look at it differently in the criminal context than in the civil context. Criminally, I think my colleagues at Kaplan Hecker would say that everyone is entitled to a defense, and while there may be some criminal defendants that we wouldn't or that they wouldn't want to represent, the breadth of whom you represent criminally when someone's facing imprisonment is different than civil.
Civilly, personally, it's a choice—and we, at Kaplan Hecker, think very seriously about these issues. We talk about them among the partners, and we won't take on a client who we feel somehow contravenes our values in some fundamental way. But that's a choice. I wouldn't judge another lawyer who did that because that's what lawyers do, if that makes sense.
DL: That makes perfect sense, especially as you were saying in the civil context as well, because look, [clients] have a wide variety of lawyers they can choose from, and you have clients that you can choose from, you're very busy, and not everyone is entitled to Roberta Kaplan. I totally get that.
RK: Other than E. Jean Carroll, who's entitled to me.
DL: Indeed, indeed—and Edie Windsor, who was amazing, of course. This might be a dumb question, but is [Windsor] the win that you are most proud of in your long career? And if that is, then do you have a number two?
RK: Charlottesville. Edie would be first, Charlottesville number two. Charlottesville, unfortunately—or fortunately, depending on how you look at it—was not covered that much. And the reason why is there were two highly racially motivated criminal trials going on at the same time. They were both in state court, so they were televised. So for the press, it was very easy to cover both those cases rather than cover Charlottesville, which had no cameras in the courtroom because we were in federal court, with very severe restrictions for Covid, and other things about access to the courtroom too. And I guess sadly in certain ways, the record we made wasn't really the focus of people's attention the way it should have been.
But because of that, I don't think people realize how incredibly difficult it was. We were on trial for about four weeks. We had about a week of jury selection, so about five weeks total. Two of the defendants were pro se, Richard Spencer and Chris Cantwell. Chris Cantwell was then serving a sentence in federal prison for making violent threats against another white supremacist—I think he threatened to rape and kill his wife—but a week either before or after that, he made similar violent threats against me, saying something like, “When this case is over, we're gonna….”
Can I swear on this?
DL: Yeah, go for it.
RK: “When this case is over, we’re gonna have a lot of f**king fun with Robbie Kaplan.” And so we were in trial in this closed courtroom—the whole courthouse was closed, there was no other case going on for four weeks—with these two, with a bunch of defendants, but two of them who were pro se. I think Judge Moon rightly probably let them get away with almost anything they wanted to do because he was very concerned about an appellate record. And in retrospect, he was probably right.
But living through it every day was extremely hard. They would just make incredibly outrageous arguments. Chris Cantwell in his closing started screaming, and I thought threatening the jury. The marshals would say to me, “Okay, you know, if Cantwell gets closer to you, we're gonna stay closer by you in case he tries anything.” It was crazy. And so just as a sheer endurance contest, and for being able to keep our dignity in the face of a trial where literally every day these guys were talking about how much they loved Mein Kampf—the rhetoric was unbelievable—is something I'm very proud of. And it's not just me, it's our entire team. I don't know how we did it so long, but we somehow managed to do it, and getting the verdict we did was incredible.
DL: Absolutely. Congratulations. And Karen Dunn [of Paul, Weiss], Alan Levine [of Cooley]—you had a lot of other amazing lawyers involved as well, and other law firms. Did you have personal security at some point in addition to the marshals?
RK: Yeah, I can't get into it, but yeah, so that made it hard too. We were really kind of trapped in the hotel in a lot of ways for security reasons. So imagine going from this closed-in courtroom to being trapped within the hotel for four weeks and thinking about how you're going to cross-examine someone about Mein Kampf or put on Deborah Lipstadt to talk about why these guys are obsessed with the Holocaust. It was something, for sure.
DL: Yeah. But a great victory, a huge verdict, and a real blow against white supremacists and others who would harm the country.
On a happier note, Kaplan Hecker & Fink celebrated its fifth anniversary, I guess this was over the summer?
RK: Yeah, July 1.
DL: Congratulations. What are you most proud of about the firm so far?
RK: When we set out to create this firm, we had certain specific core values. One, doing work in the public interest together with commercial work and white-collar work. Two, having a paramount respect for maintaining our culture and making sure that we all liked each other and were friends and had the same values. And three, being as non-hierarchical as you can possibly be, in the sense that we hire, I think we now have 10 percent of our lawyers are Supreme Court clerks. That's kind of insane—like, I couldn't get a job with me anymore. But because we bring in such brilliant people, we make sure that we listen to their ideas, from day one.
What I'm most proud of is that we kept to that. We really have to this day kept to that. Our greatest challenge, frankly, is not getting so large that we lose it. That's frankly the thing that we worry about the most right now. There are a number of partnerships where the partners don't know each other well enough to keep that sense of camaraderie and culture, and that's what we face every day. We're not there yet for sure, but that's what we think about a lot.
DL: Right now the firm I think has around 60 lawyers, maybe 10 partners or so?
RK: I think we’re about—well, maybe about 13 or 14 partners.
DL: Oh, okay.
RK: And I think the limit for me, based on my experience, is about 25. Once you get to more than 25, it's hard for everyone to be friends the same way we are now. So we have some room to grow.
DL: And what about total lawyers? Right now you're around 60-ish?
RK: Yeah. Again, we don't know, but I think everyone agrees that at 125 we'd pretty much be at our limits. Again, we're nowhere near that now, but that's kind of what people have in mind, and I'm not sure all of us want to get even that big. We also, I think speaking unanimously for the partners, are not into this idea of having a lot of satellite offices.
DL: That was my next question.
RK: We have New York, which is kind of the main office, and then we have D.C., and I don't anticipate us expanding anywhere else. Before Covid, we might have thought about an office in California. One of the few good things about Covid, of very few good things, is that you see that you can practice across state lines in a much easier way than I ever anticipated. So I can't imagine [opening more offices] anytime in the near future.
DL: Yeah, I totally agree with you. I don't think it's quite as imperative, and in this day and age of remote work, it is much easier.
Let me ask you this question because people have asked me about it, and I'm genuinely curious for the answer. At Kaplan Hecker & Fink, you do tons of public interest work, you do tons of pro bono work, and then, on the other hand, you still pay above the Biglaw salary scale for associates.
Something here is not computing. How do you do it? Maybe I'm being too nosy, but… are you content to just make, you know, a couple million rather than many millions, like you did at Paul, Weiss? What's the secret here?
RK: I'm not going to get into any numbers—obviously, my partners would kill me—but let me put it this way: other than in our first year probably, I have not had to sacrifice anything financially at Kaplan Hecker & Fink.
DL: Wow.
RK: And I think for me and almost all the partners, we are doing appreciably better than we would have at big firms.
What's our secret sauce? For one thing, we are very, very efficient. Even though our fees aren't significantly lower than big firms, our bills tend to be, because we don't have to have four levels of people working on something. The work product that we get from our associates is usually excellent and doesn't take as much work than it might at a big firm.
Two, we're very creative about fee arrangements, which is also not a big-firm thing, at least in the past—it may be more so now. My managing partner, Julie Fink, was a client at Pfizer for years before she came here, and so she really understood this. We're very creative about success fees or contingency fees or flat fees in a way that I think is hard at big firms.
DL: Hmm-mmm.
RK: But suffice it to say that we're doing—knock wood, I’m knocking wood right now—we're doing okay, and we're pleased to be able to pay our associates and our staff the way we do. And money is not the paramount thing. No one comes to Kaplan Hecker thinking, “I want to earn as much as a hedge-fund person or an investment banker or a tech guy.” We do very well, and no one is in any financial distress. But maximizing dollar amounts per share, per partner, is not our number-one goal.
DL: That makes perfect sense. I'm curious, since you mentioned contingency-fee arrangements—do you do a significant amount of plaintiff-side that work that helps generate unusually high revenue per lawyer, perhaps?
RK: We've done some, we're certainly interested in doing more. We probably get, I don't know, I'd have to look at the numbers,.we get between six and a dozen people calling a week [with such cases]. We've probably turned down, I think the numbers have got to be 90, upwards of 95 percent of those. But the ones we take on tend to be profitable, so yes, that certainly helps the bottom line.
DL: And then another thing I've heard about the firm is some of your public-interest work is also paid work, right? That it's not just entirely pro bono?
RK: Yeah, some of it is funded. It's funded at a lower rate, so we have a public-interest rate we use that’s about half our regular rate. We do a number of cases like that—a lot of the election work, cases that Joshua Matz does, are funded in that way.
DL: Okay. So one last question before we go to my little lightning round of final questions. And again, maybe this is a delicate subject, but some people in the law firm world say you're a tough boss. Do you consider yourself a tough boss?
RK: So let me tell you a story. Paul, Weiss had upward reviews. I don't remember when they started, but at some point when I was a partner, they started upward reviews. And my upward reviews—I'm not proud of this—but I would always have maybe one or two associates at a time that I didn't work so well with, and it always turned out that of the people who did the reviews, those would be the people who would turn in reviews. And so my upward reviews were not great. Then I did the Windsor case, and all of a sudden my upward reviews were stellar! I remember my wife saying to me, “Well, look, I don't understand.” Because I don't think I changed as a boss. I think what changed is the way people perceived me as a boss.
DL: Hmm-mmm.
RK: So, I don't know. Those were a long time ago, and I know I was under a lot of stress as a young partner at Paul, Weiss. But I don't think anyone today—you can ask them yourselves—has a problem with me as a boss. I certainly, and we all do, have high standards. We operate in very demanding situations, and our clients justifiably expect a lot from us. But I don't think anyone in the Charlottesville case or in E. Jean or in any of the paying matters for Airbnb or Uber would say I’m tough. If by tough you mean I have high standards, yes. But I’m also mentoring people and giving people opportunities to take depositions and to examine people at trial. We were the only firm in Charlottesville that had associates examining witnesses.
DL: Wow. That's remarkable.
RK: And that speaks for itself.
DL: Totally, totally.
So here are my standard final questions, which are standard for all my lawyer guests.
My first is, what do you like the least about the law? And this can either be the practice of law or law as that abstract system that rules over us all.
RK: I think what I like the least is the tendency of lawyers and judges at times to fail to see that behind all this case law and precedent and statutory language are real people, and that each case affects a real live person. And it's hard to keep those things balanced in your head, but good lawyers and good judges need to. And I sometimes find it very frustrating when people take things to such a level of abstraction that they fail to see the common humanity in what we do.
DL: And I think that is one of your talents as a lawyer, just bringing out the humanity of your clients, whether it's Edie Windsor or Heather Heyer or E. Jean Carroll. I think your storytelling about these very real, flesh-and-blood people is something that just stands out about your practice,
RK: Thank you, because I would like someone to say that about me, so I'm very pleased that you have. That's something we really care about a lot at Kaplan Hecker.
DL: My second question is—and this'll be interesting because I know that from a young age, I think you have a line in your book about how at age 10 or 12, you were plotting out your legal career—what would you be if you were not a lawyer?
RK: Believe it or not, because it's pretty timely, I thought seriously about becoming a Russian historian.
DL: That was your undergrad major.
RK: Yeah, I was a Russian history and lit major, and I spent—I think it was probably the single biggest influence on who I became—I spent the spring semester of my junior year in Moscow, in what was then the Soviet Union, but glasnost had been announced. So it was kind of the beginning of change, although change that didn't last very long. And I think that semester, I was fluent in Russian then, watching and living in what was then a totalitarian regime in, in a lot of ways—we were bugged and all kinds of things—just had a huge impact on the way I see the world. And maybe that made me a good lawyer, because I always expect the worst—which is a good thing as a lawyer in a lot of ways, because you want to be planning for and anticipating all contingencies.
I ultimately realized that there are not a lot of happy years in Russian history, sadly continuing to today, and that if I became a Russian historian, it was going to be pretty depressing. But I originally went to law school just thinking, “Okay, this will be a way to figure out what else I want to do in my life.” And then I fell in love with it. I’d kind of forgotten about what I was thinking as a 10-year-old about getting paid to talk.
Oh, and I flirted with the idea of going to the CIA.
DL: Oh?
RK: I started taking Russian because that was a big period of global crisis between the Soviet Union and the United States. My professor at Harvard was Richard Pipes, who came up with the phrase “the evil empire.” And I thought about it, but at that time, I don't think it would've been very easy for someone who was—I wasn't out as gay, but I certainly had concerns that I was gay and or lesbian, and I was smart enough to know that that probably wouldn't mix too well with going into either the NSA or CIA. So I didn't do it.
DL: Mmm-hmm.
RK: Probably the best for me in a whole lot of ways.
DL: And certainly history has benefited from your choice to become a lawyer.
So my third question is, how much sleep do you get each night?
RK: Believe it or not, I’m probably at the high end of the people you’ve talked to, seven to eight hours a night. I've never been someone who's functioned well with very little sleep. I remember my freshman year in college, some of my friends and I decided as an experiment that we were going to stay up all night and then write some essay that was required for some writing class we had to take, taking a lot of NoDoz, like only freshmen in college would be stupid enough to do something like that. But suffice it to say, I had to ask for an extension of the due date for the essay.
When I’m on trial, I sleep obviously a lot less, but even then I'll go to bed at midnight and wake up at four or five in the morning. I still need to sleep every night.
DL: I'm glad to hear that. I always love talking to successful people who [get decent sleep]. And who are also working parents—you have a son. I think it's great when people can… Look, I know work-life balance may be sort of an illusion or maybe a little much to ask, but I'm glad to hear that you can get a decent amount of sleep.
RK: I've had migraines ever since I was 12. I suffer from migraines, and if you sleep too little, it will bring on migraines. I remember once, when I was working for Chief Judge Kaye, I hadn’t slept enough or I don't know what had happened, but she came into my office and I was curled up under my desk in the fetal position because I had a migraine. And I'll never forget, she thought I would die. She's like, “What is going on?” So since I suffer from something like that, I'm very careful about doing things that won't bring on a migraine, and lack of sleep—or even too much sleep, both sides—can cause migraines.
DL: My final question: any words of wisdom for listeners who look at your life and career and say, I want to be Robbie Kaplan?
RK: I'm not sure anyone should say that because we all have our own lives, and you shouldn't want my life any more than anyone should want anyone else's.
But I would say one, stick to your guts. The single greatest lesson I've learned as a lawyer is to trust your own guts because they often tell you the right thing. There's a lot of distractions that you may listen to or follow instead of following your own inner voice, and that's really important, to hear your own inner voice.
And two, and I alluded to this earlier, your ability to function as a lawyer is based on your integrity, and you should never, ever, no matter what the fee, what the pressure, what the circumstance—and again, we're seeing this today, unfortunately—never do anything for a client that in any way compromises your integrity. I learned that at Paul, Weiss. I learned it from my mentor at Paul, Weiss, Marty London, and a bunch of others. And it's the single most important thing you need to know as a lawyer.
DL: Well said. Thank you so much, Robbie, for joining me. I am so grateful for your time and your insight, and I know my listeners will appreciate it as well.
RK: It's a pleasure.
DL: Thanks again to Robbie for joining me. She’s had such a remarkable life and legal career, and it was wonderful to hear about her landmark wins and what she’s working on today. If you haven’t already read it, I highly recommend her memoir, Then Comes Marriage.
As always, thanks to Tommy Harron, my sound engineer here at Original Jurisdiction, and thanks to you, my listeners and readers, for tuning in. If you’d like to connect with me, you can email me at davidlat@substack.com, and you can find me on Twitter, Facebook, and LinkedIn, at davidlat, and on Instagram at davidbenjaminlat.
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[UPDATE (11/5/2022, 9:16 a.m.): A reader pointed to me that the Trump Justice Department secured a life sentence for James Alex Fields Jr., the Ohio man who drove his car into the crowd, killing Heather Heyer and injuring dozens of others. The indictment was obtained in June 2018 under Attorney General Jeff Sessions, who declared that the charges “should send a clear message to every would-be criminal in America that we aggressively prosecute violent crimes of hate that threaten the core principles of our nation.”
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