In 2013, the U.S. Supreme Court held that the federal Defense of Marriage Act was unconstitutional. The case challenging the law was brought by an octogenarian widow, Edie Windsor, who was stuck with a tax bill for her wife’s estate—which wouldn’t have been the case had federal law allowed her to take the surviving spouse deduction.
Windsor’s case was argued in the Supreme Court by Roberta Kaplan, then a partner at Paul, Weiss in New York. Kaplan has continued making news, suing neo-Nazis and others in the so-called “Alt-Right” for their role in organizing violent protests in Charlottesville, as well as Donald Trump for defamation on behalf of E. Jean Carroll, who accused him of raping her in the 1990s. She has also since left Paul, Weiss to form her own firm, Kaplan, Hecker & Fink, where she continues to take on public interest cases as well as high-stakes commercial litigation. Kaplan and I spoke by phone in late 2019 about some of the highlights of her career and challenges facing the legal profession.
Eliot Turner: Many people are familiar with your work representing Edie Windsor and the Supreme Court’s decision in her case, United States v. Windsor, 570 U.S. 744, which held that the Defense of Marriage Act, which denied federal recognition of same-sex marriage, was unconstitutional. But I wanted to talk about your work on marriage equality litigation before you began representing Ms. Windsor. And specifically your case Samuels v. New York State Department of Health.
Roberta Kaplan: You got the name right. Because the case is always named after Hernandez, which is the companion case.
ET: [laughter] I actually went on Westlaw to look.
RK: I was going to say thank you for that.
ET: You’re welcome. So the result in Samuels was different than Windsor. There the New York Court of Appeals held that New York’s definition of marriage as only between a man and a woman was constitutional and didn’t deny gay and lesbian couples due process or equal protection. [7 N.Y3d 338 (2006).] As litigators, I think it’s always important to look back at the cases that we didn’t win and see what we learned from them. What, if anything, did you learn from Samuels and how did that affect the strategy in Windsor?
RK: So I completely agree with you. We learn as much from our losses as our wins. And Samuels, in a lot of ways, was a heartbreaking loss. But it did teach me lessons that we used in Windsor. In the marriage equality and generally in the LGBT equality cases that had been litigated through Samuels and up until Windsor, it was very common to have a group of plaintiffs. And for good reason. You really wanted to represent the full diversity of the community in the case. And so in marriage equality cases, it was common to have an older couple, a gay male couple, a lesbian couple, a diverse minority couple, and so on. I totally appreciate and understand the reasons why you would want to do that, because these cases are so public and in a lot of ways the plaintiffs and the plaintiffs’ lives become the case—at least the way the public perceives it.
What I don’t think I realized until Samuels was that there was a flaw in that model, that I don’t think we had appreciated. And the flaw in that model is that if you have a case with four or five or however many couples, the facts of those people’s lives and the couples’ lives tend to fade in the background—because no one could focus really on the lives and the problems in the day-to-day existence of 12 or more different people. In Windsor, there was one person really—one couple but really only one person, since Thea Speyer had passed away—both the public and I would venture to say the judges were able to focus on the acute injustice of the tax bill that Edie was faced with in a way that I don’t think those earlier cases had allowed us to present. So that was a huge lesson. It’s not something that I think any of us realized, at least until Samuels. And when the plaintiffs and their lives fade into the background, the issue becomes much more like a fight between—it sounds funny to say it today because it’s even more so—a fight between Fox News and MSNBC rather than a case about real people’s lives and how constitutional principles apply. And that was definitely true of Samuels. It became very politicized.
The second lesson that I think I learned from Samuels is—certainly in gay rights cases—that a lot of the work that had to be done had to be done outside of courtrooms and briefs. And had to be done in our society at large. When Samuels was argued in 2006, Vermont had civil unions, Connecticut had civil unions, Massachusetts obviously had marriage. They were considering it in New Jersey but hadn’t decided. But that was basically it.
By the time that I argued Windsor, there were 23 states. By the time Windsor was decided, it was 30-some states. And, of course, within two years after Windsor, it was to be the majority of all the states when Obergefell v. Hodges [135 S. Ct. 2584 (2015)] was decided two years later.
In all those cases, the arguments in the briefs from Samuels to Windsor to Obergefell all would have looked—all did look—very much the same. What changed was not the argument, certainly not the clauses of the Constitution; what changed was people’s perception. I think the phrase I used at oral argument in Samuels was “Be brave.” But asking the New York Court of Appeals to be brave and to come out as one of the early states upholding the rights of LGBT people was not as good an argument as saying come join the majority, or the plurality, of states that have already done so.
ET: But even at the time that you took on Windsor, there were a number of people who questioned whether the time for litigating this issue was right. Whether it was too early or whether even the courts were really the best vehicle, given that there had been at least some success in changing the issue legislatively in the states. Of course, Edie Windsor couldn’t wait. It was an immediate issue for her. . . .
RK: An immediate $600,000 issue for Edie Windsor.
ET: But it was also a decision that was going to affect many people, including your family, one way or the other. How do you attempt to balance that concern for the broader principle that you’re advocating for with the needs of your individual client?
RK: So it’s very good question. When I talked about the Windsor case, I talked about the number of states by the time we argued. But when we brought Windsor, I think, only nine states permitted gay marriage. The numbers were very, very different. We thought very, very long and hard about it. In a lot of ways, frankly, the determinative factor—at least for me—was that Mary Bonauto, the lawyer from GLAAD in Massachusetts, who had brought the marriage equality case in Massachusetts, had already brought her own case challenging DOMA in the First Circuit. And given the fact that someone as cautious, as prudent, and as successful a lawyer as Mary had already filed that case was a big factor in deciding that it was appropriate for Edie to go forward. Ultimately, the problem with that First Circuit case was that Justice Kagan had to recuse—when the case was filed, she was the solicitor general and presumably was involved in discussions about it. So filing the Windsor case in the Second Circuit, where not only did you not have the Kagan recusal problem but also there was an open issue about whether statutes that treated gay people differently were subject to some form of heightened scrutiny, was a huge advantage.
The second point you raised, which is kind of pertinent here, was my own situation. And I was very conscious of it, and I certainly tried very, very hard to keep my position and my family and my marriage out of it. During the case, I had a Post-it that I kept on the laptop that I used to write a lot of the brief and prepare for oral argument. And the Post-it said, borrowing from Bill Clinton’s presidential campaign: “It’s all about Edie, stupid!” We thought that the way to win this case was to persuade the judges and the courts to make it about Edie’s life and her marriage. And to persuade the judges that Edie’s marriage was no different from their marriages. That it was a marriage that anyone should aspire to and that it should be treated equally, with equal dignity, under the law. Subconsciously, however, I think I had that Post-it up there because it was a constant reminder to myself that I had to keep my—to use a fancy legal term, my mishigas out of it. And that my goal, as I had been taught since the very beginning of my career, was to represent my client and my client only. To not think about how her case would impact me personally. I think, for the most part, I managed to succeed in that. There were a couple of times when I kind of cracked. The one that I remember keenly is, during the oral argument at the Supreme Court, there was a point where the chief justice asked me a question like: “Isn’t it true that politicians are falling over themselves to support your side of the case?” And in answering the question, my voice cracked. You can hear it on the audio. Every time I hear that, I’m like, you know, that’s Robbie Kaplan coming out. I just couldn’t hold it back anymore.
ET: In addition to learning from our losses, we learn from our wins too. What did you learn from the Windsor case?
RK: Teamwork. I knew that already, but Windsor certainly supported my views or reinforced my views about that. The case was not won by me. It was won by a very large team of lawyers at Paul, Weiss and the ACLU and, probably most crucially, Pam Karlan at Stanford Law School, who I didn’t know at all before we filed the case. As it became clear that there was a very real possibility that the case would go to the Supreme Court, I called her up out of the blue and said, “Hi, I’m Robbie Kaplan. Nice to meet you. I have a case that might go to the Supreme Court. Would you help?” And she was supposed to go to Italy to teach that spring and canceled that. She was a huge factor in our victory.
I think your clients—particularly for these kinds of constitutional, for lack of a better term, public interest cases—who your clients are really, really matters. There’s no doubt that having someone as smart, as photogenic, as charming, as articulate as Edie, not to mention the incredible story of her marriage to Thea, had a huge impact on the case.
ET: In public interest cases, you’re often presented with two very starkly different views of the world. Competing visions of reality. I know that, from my own experience, sometimes it’s hard for me to believe that the other side is actually making these arguments in good faith, but sometimes they are. They have firm convictions. I’ve heard you say that when the other side in Windsor brought up the fact that Edie had once been married to a man, presumably to argue that being lesbian was a choice and therefore could not be a protected class, you actually welcomed them making that argument.
RK: I was thrilled.
ET: How do you engage with opponents on arguments you think are dubious and questionable and present a really different view of the world, without losing the force of your own advocacy or questioning whether they are brought in good faith?
RK: I have to give credit to my adversary in this case: Paul Clement. This was an issue they raised in discovery at the trial court level. I think they raised it in papers in trial court but they never really raised it after that. They were good lawyers on the other side, and they realized that it wasn’t a very powerful argument for them. And they backed off it.
What I loved so much about it was that it gave me the opportunity to put it in an affidavit from Edie about her first marriage. Yet, if you look at Paul’s argument to the Supreme Court—both in the oral argument and in the briefs—they were very careful about what they argued. Most of it was about uniformity, deference to the legislature. So there wasn’t anything that I really found that I remember being in that category of stuff.
That, however, does not apply to the amici in Windsor. I think there were 45 amicus briefs on the other side, and they kind of went from crazy to crazier to craziest. In a lot of ways, we welcomed that. At the Supreme Court, you generally give a blanket waiver for people to file amicus briefs. But Pam advised, very wisely, that we not should do that, not because we ever said no, but because by having to ask us for permission, we knew who was going to be filing amicus briefs. I’m pretty sure the first request we got was from the Westboro Baptist Church. And it—you know, like the inquiry that the other side made about Edie’s first marriage, we were delighted that the first amicus brief coming in from the other side was from those really quite horrifying people who protest at funerals.
So it really ironically didn’t come up that much. And another thing that I guess was kind of a harbinger of the result is that I didn’t get attacked very much. At least that I was aware of, you know, personally. A couple weeks before the argument, there was an evangelical prayer group that said they were praying for me to lose. But compared to the attacks I get in the Charlottesville case today, it was a completely different universe.
ET: Has Windsor changed your practice?
RK: I don’t think it changed the nature of my practice in the sense that, immediately after Windsor and certainly through today, I still did the same mix of commercial and public interest work and I continued do that afterwards. It’s what I do today. But becoming a very well-known lawyer changes your practice a lot. People are considering you for cases, and clients consider you for cases, where they probably wouldn’t have known about you previously. And that’s a problem—to be frank—that’s probably much more acute for women and for women litigators than it is for men. So getting the boost from the victory in Windsor was obviously a wonderful thing for my practice because it just gave me an opportunity—it gave me a platform that was much, much larger than I had had before.
ET: That actually raises a related point. I’ve heard you say that although there is still sexism in the profession, today’s lawyers—the lawyers who are entering practice now—can’t really imagine what it was like when you were starting out in the early 1990s. And I’m sure that people who were starting out 20 years before that would say that you couldn’t imagine what it was like then. What’s changed since you started, what hasn’t, and what more can we do and do we need to do to fix the problems that women still face in the law today?
RK: When I think about this, I think the thing that has changed the most or that has had the biggest impact of improving—I’m just speaking about litigation now because that’s the world I know best—that has improved for practices of the day-to-day practice of so many women litigators is having so many women judges. The difference between today and when I was a young associate, between the number of women judges, and,I’m thinking most particularly of my home bench in the Southern District of New York, is just night and day.
President Obama deserves—and other presidents deserve—a lot of credit for this. Appointing so many women to the federal, and even to the state, bench, both symbolically and then very practically, just makes it much more the norm for women to show up in court and to argue cases in court and to be treated just like their male colleagues. That wasn’t true when I was starting out as an associate.
I remember as a junior associate, and this is not a criticism of either of them, but I remember going into court with one of my mentors, Marty London, a really, really great trial lawyer, in the Southern District of New York before Judge John Martin. Before the conference started, there was this whole, friendly, and really quite lovely exchange between Marty and Judge Martin about fishing. Marty was a big fisherman. How’s the fishing, where have you been fishing this season, and that kind of thing. And I remember thinking, as a young associate, that will never happen to me. I will never have this advantage where I can go into court and have that kind of relationship with a judge or have that kind of kind of camaraderie with a judge.
I called Marty a couple years ago, and I told him the story and that it had happened to me. I said I can’t believe it, but now I’m getting treated like Marty London. That is very much I think the product of really incredible efforts by the ABA and by presidents and by the Senate to put so many women on the bench. And I’m going to be a little bit political here in saying that the record of the Trump administration on this is really abysmal. The vast majority of the people he has appointed to the bench are men, and not minority men, and we really should not be turning back the clock that way.
ET: What is the biggest problem that women face in the law today and what can we do about it?
RK: I think the biggest problem today is really the glass ceiling. Maybe below the glass ceiling. I guess the glass desktop. I don’t know what the analogy would be, but we have a situation where we have all these great women going to law school, coming into law firms, and then, for whatever reason, not sticking it out for a whole bunch of reasons or sticking it out and not usually being able to ascend to the leadership of their practice groups of law firms. That has to change. It can’t be that the managing partners of the vast majority of the AmLaw 100 firms are all men. And just like having women judges on the bench, we need to make that same change in the private bar.
ET: For a very long time, you practiced at a very well-regarded white-shoe firm. But a few years ago, you decided to open your own firm. Why did you decide to make the move and what have its benefits been?
RK: I had had a sense for a number of years—and this is not a Paul, Weiss issue; it is a big-firm issue much more than it is a Paul, Weiss issue—that the litigation in big firms had really become less and less diverse in terms of the types of cases that the top 10 or 20 firms are able to take on. The size of the cases that they were able to take on. I wanted to get back to the kind of cases that I did a lot of when I was starting out at Paul, Weiss. Rich guy versus rich guy cases. Unfortunately, there are not a lot of rich women versus rich women cases. But cases that were smaller, that were more kind of factually intensive than enormous multinational, multi-partner investigations or civil litigations resulting from investigations. And again, no criticism of Paul, Weiss, the model had just changed over the years. To the great success of Paul, Weiss and other firms financially. But I really missed doing that kind of work and I wanted to go back to it. That was really in a lot of ways the primary motivation for starting Kaplan Hecker.
I was not worried that I wouldn’t be able to put food on the table for my family. I was pretty confident that would be fine. But I hadn’t fully appreciated that that my instincts were right about the market and the desire for clients to have firms like ours that have a lot more flexibility. In terms of what kind of cases they take. In terms of conflicts. The cherry on top is that by having this great kind of mix between commercial work and public interest work, which very much came from the original Paul, Weiss model, we are able to attract associates who are so superb that we end up being incredibly efficient when we do the work that we’re given.
ET: Aside from attracting talented associates who are interested in working on high-profile public interest matters, do you see the two different kinds of cases, fee-paying work and the public interest work, complementing each other?
RK: They’re complementary in a bunch of ways. I’m very old school about this. So I believe that the way to be a great litigator is to be a great litigator. And then that the skills of being a great litigator, which include writing clearly and concisely and persuasively, marshaling the facts to your client’s advantage, understanding, particularly in today’s mobile and social media, the kind of the social media and the press outlook on whatever the issue is. It doesn’t really matter, frankly, whether it’s a fee-paying case. Whether it’s a public interest case. Those skills are all the same. So unless you are in certain areas that are really highly specialized, which we don’t do—like patent work as an example—the associate who does great work on our civil rights lawsuit against the white supremacists who staged the violence in Charlottesville is the same associate who very often is doing great work for Airbnb or Uber. Because, again, it’s not the substantive law that, frankly, is all that difficult or tough; it’s all the skills that you use within that legal framework. We don’t see a big difference. We don’t have any separation of associates. Every associate does both kinds of cases.
ET: You helped start the Time’s Up Legal Defense Fund, which helps support cases challenging sexual harassment in the workplace, particularly for people in low-wage industries. That seems to be both a recognition about how our court system can help relatively powerless people vindicate personal and societal interests, but also that a lot of people don’t have access to the courts because litigation is so expensive. How do we address the problem of access to the courts, or is it the case that most people are priced out of justice?
RK: The concept of being priced out of justice was exactly what motivated the creation of the Time’s Up Legal Defense Fund. And the reason that has happened, in large part, is changes in the law that happened after I started practicing. So a combination of increased use of arbitration, particularly in employment contacts, meant that even if people arbitrated and got awards, other people didn’t know about it. That made it hard to build up a case of systemic or continued harassment in this area, because you were kind of operating in the dark. The Supreme Court’s decision in Walmart v. Dukes [564 U.S. 338 (2011)] exacerbated the problem, as it effectively eliminated, or at least severely impaired, the ability to bring these cases as class actions. The limitations on how much money you can get, for example, in Title VII cases are another impediment. As are very strict filing deadlines. All this created a situation where, because of the economics, the only people who were getting represented were the relatively few—let’s just limit it to women for now—the relatively few women who had high salaries and therefore made the cases economically advantageous for a lawyer to take the case on contingency. Or cases against people where the need for secrecy was so great from the defendant’s perspective, I call them embarrassment cases, where settlements are paid above and beyond what the plaintiff might get in court to keep it from the public. But most women who were working in middle-class and, indeed, at low-wage jobs and who faced discrimination couldn’t find lawyers to represent them because it—and it’s not the lawyer’s fault—it just didn’t make economic sense for them to do so. The contingency awards to make it worth their while. And so that is really what was the motivation for the fund. As we started to talk about these issues, we realized that there was this problem, and we set up the fund to incentivize lawyers to bring these kind of cases. And I think it’s working. It seems to be working—at least in certain areas. The class action cases against McDonald’s are all funded by the Time’s Up Legal Defense Fund. And they obviously involve women who earn very low wages.
ET: This is a bit of a softball, but what was your favorite moment in court?
RK: It’s a softball, but it’s not an easy question to answer. I think it was after the Windsor argument, honestly. And it was the moment I concluded the argument, I kind of replayed it—and I’m really old, so I finish an argument like that, I remember having a cassette recorder and pressing rewind. In my head, I pressed rewind on the cassette and I kind of replay what happened in my head, and I remember just having this overwhelming feeling of relief. It wasn’t even joy. It was relief that I hadn’t screwed it up, because I had such a weight of responsibility on my shoulders for so many people. And I turned to Pam Karlan at counsel table and said I don’t think I—you know, I think my answers were good. I don’t think I needed to change my answers. And Pam said, “I completely agree.” That was certainly my most memorable moment in court.