Robbie Kaplan of Kaplan Hecker & Fink LLP
Which Two Things Are True At Once?
"FEARLESS CREATIVE LEADERSHIP" PODCAST - TRANSCRIPT
Episode 253: Robbie Kaplan
Here’s a question. Which two things are true at once?
I’m Charles Day. I work with creative and innovative companies. I’m asked to help their leaders discover what they’re capable of. And then to maximize their impact. Helping them to unlock their own creativity as well as the creativity of the people around them.
Welcome to the intersection of strategy and humanity.
This week’s guest is Robbie Kaplan. Robbie is a lawyer and the founding partner at Kaplan Hecker & Fink LLP.
Robbie is best known for successfully challenging a key provision of the Defense of Marriage Act. Today, gay marriage is legal in America because Robbie Kaplan stood in front of the Supreme Court and argued for it.
Recently, she was E. Jean Carroll’s lawyer in both of her successful lawsuits against Donald Trump.
And among Robbie's many awards is one from The Financial Times, which named her the “Most Innovative Lawyer of the Year”.
People that know her, say about Robbie Kaplan, “she just sees things from a thousand different angles all at once, it’s hard to keep up with her thought processes. She’s not afraid, if she sees a problem, to go figure out some law that’s going to allow her to fix it.”
Others say she is “a lawyer that you don’t want to see opposing you.”
They say, “she’s brilliant, she’s unrelenting, she can’t be intimidated and she’s not going to back down. She eats bullies for lunch.”
And the Washington Post has described Robbie as “a brash and original strategist, a crusader for underdogs who has won almost every legal accolade imaginable.”
Which may make this admission surprising.
“It's still not typical for a woman to be a very prominent lawyer. And even though sometimes I know in my brain that I am, and I know in my brain it's because I'm very talented at what I do, and have won a whole bunch of things, there are times in my gut where I worry that I'm an imposter.”
Not everyone doubts themselves.
But many people do.
If you are one of those people, if sometimes feeling that you are an imposter is holding you back, is preventing you from unlocking the potential of the people around you, as in yourself, then let me offer you this.
Two things can be true at once.
You can feel like an imposter and achieve extraordinary things at the same time.
You do have to be clear about the extraordinary things, and why they matter to you.
But then that’s what leadership is all about.
Here’s Robbie Kaplan.
Charles (02:58):
Robbie, welcome to Fearless. Thank you so much for coming on the show.
Robbie Kaplan (03:01):
Charles, thank you. It's a pleasure.
Charles (03:03):
When did creativity first show up in your life? When are you first conscious of creativity as a force in your life?
Robbie Kaplan (03:09):
So that's an interesting question because, well, I think in certain ways I'm creative. It's not in classic ways of being creative. Back in high school I had an art teacher who was very aggravated with me because every time I thought I was making a pot, he thought I was surreptitiously trying to make a bong. And he got so frustrated with me, he told me I should never take another art class again as long as I live. So, I think it's fair to say that the traditional notion or the kind of, the more standard notion of creativity in terms of artistic expression, is not a high point for me. However, in terms of what I do today, with day-to-day, which is practice as a lawyer, I think I can be very creative. It's just being creative within the constraints of, kind of the law and the procedure and the statutes I have to deal with.
Charles (03:55):
And do you find the structure of the law makes that harder or easier? Is it helpful to have a firm reference point to work against in terms of unlocking creative thinking from that standpoint?
Robbie Kaplan (04:06):
See, what I, I don't know, I'm going to say what I enjoy most about being a lawyer. One of the things I enjoy most about being a lawyer is strategizing, and getting a problem from a client at the very beginning, and thinking about what steps should be taken to achieve whatever result the client wants to achieve. And those often vary quite considerably based upon both what the client wants to happen and the timeframe the client wants it to happen in. And so within those constraints of procedural rules, substantive rules, judges, et cetera, I think at times I can be very creative. I think I'm kind of known for that, about how to get to the end goal. But, you’re right. You're working within a very established framework, and maybe it's because the creativity is so cabin in certain ways is why I'm so good at it. I honestly don't know.
Charles (04:56):
You said in an interview when you as a kid, you wouldn't stop talking, that you love to talk. I read somewhere you had a conversation with your grandmother who said, “Robbie, I love you, but can you just be quiet for, like, three minutes? Can you stop for three minutes?” You said something like, “No, grandma, I can't, I just can't help myself. I love to talk.” I read somewhere William Faulkner said, “I don’t know what I think until I read what I said.” Does talking do the same thing for you? What is it about talking that you love?
Robbie Kaplan (05:19):
I think that's right. My brain operates in a certain way. I'm kind of more conscious of this because my wife and my son's brains are very different than mine. So as I've kind of, as our son has grown up, I think I've been more and more conscious of this. I tend to think very rapidly, perhaps too rapidly at times. And I tend to speak very rapidly, as well. And I think it's easier for me to say something or sometimes to write something. I’ve actually gotten to the point in my career where I actually like legal writing, I enjoy it. It helps me process my thoughts. I think that's absolutely correct,
But my son for example, who's very creative, he will just kind of process his thoughts in his head, and think of whatever creative thought he is having, and kind of continue to develop it in his head. Whereas for me, it's easier, I think, often, to develop it out loud or to write an email or to take a note or something like that.
Charles (06:17):
So does the art of talking actually kind of slow you down in terms of being able to create construction around your thinking?
Robbie Kaplan (06:23):
I think so. I think it has at least that advantage. And, in fact, another story about my son, when he was little… Well, let me back up. I hate reading out loud because it takes too much time. And my wife and my son are big fans of audio books. I can't stand an audio book, because if I can read the page, I'm going to be able to read it twice as fast, if not more, than if I have to spend the time to listen to it. So yes, I think even within that warped way, my brain works. And even though I speak very quickly, I think the process of speaking or writing slows my brain down enough that I can kind of formulate the thought in a logical way. Again, very different from my son who I think just like kind of conjures it in his head and keeps conjuring in his head.
Charles (07:11):
And is there an emotional benefit to you from talking? Did you get something emotionally from it?
Robbie Kaplan (07:18):
I don't think so. I'm very good. I think another one of my talents, and there are plenty of faults, but one of my talents I think is I'm pretty good at reading people, at least in a legal situation. I'm pretty good at figuring out what the other side is really thinking and what their strategy is. And talking enables me to do that. I'll give you an example. So I just had to spend, we mentioned before this started, as your listeners may have known, there's kind of a crisis going on at Columbia University right now, about how to deal with students on both sides of the Palestinian and Israeli divide, and how to provide equal access to campus, and what to do with the protestors. I spent a lot of my weekend this weekend talking to various members of the Columbia community about these issues. And while I may not have completely persuaded all of them, I think I made a lot of progress in trying to explain to these various constituencies kind of the dilemma that Columbia has and why these various groups of students have different rights that have to be respected. So for me, being able to talk is a way of not only reading other people, being able to persuade other people, which is a lot of what I hope to do as part of my job.
Charles (08:30):
When you walk into a situation that's that contentious, how do you put aside your own sensibility to be able to actually navigate that at the level of which they can and want to engage with something like that?
Robbie Kaplan (08:43):
So I think that comes with my training as a lawyer. As a lawyer you really have to be trained, and I was trained this way from the very beginning, to put your own interests aside and your own emotions and everything else aside to the extent that you can, and to think about things or try to think about things solely from the perspective of the client. So my mentor at my old firm, Paul Weiss, Marty London, his book is called The Client Decides. It's very much a view that it's the client's, and the client's interests, that have to govern almost everything you do. So I think the answer to it is mostly practice. I've had a lot of practice in thinking that way, and I think it's part of my ethical duties as an attorney, representing clients to think that way. I can't tell you that there aren’t moments when kind of the Robbieness squeaks through.
One really good example is when I was arguing the Windsor case at the Supreme Court. I obviously, as a married woman with a kid, was subject to the Defense Of Marriage Act, and it was having negative implications for me and for my family. And I tried very much to kind of keep that out of my head, and we had this motto in the case, “It's all about Edie,” it's all about Edie Windsor, stupid, to really always say to each other, our focus has to be on Edie and her story, and that's how we win this case. During the argument though, at the Supreme Court, there was a moment when I got a pretty direct, pretty somewhat hostile question from the Chief Justice. And in answering the question, my voice cracked, like just completely cracked there, right there in the Supreme Court.
And every time I listen to it, because it's available on audio, I think to myself, that's the Robbie Kaplan coming up. Like, I just couldn't keep it out anymore. And the fact that I, too, was being subject to this very unconstitutional law just kind of came out at a certain point. And so, it happens. I think you have to allow it to happen. I think finding commonality with people based on your own personal issues is often the best way to persuade others of where you're coming from. But getting there can be, you know, can be delicate and tricky, for sure.
Charles (10:44):
When something like that happens… I mean, so much of what you do is so highly visible and highly public and also incredibly sensitive and delicate, with massive impact on so many people. But when something like that specifically happens, and you listen to yourself or you listen to your voice cracking, how do you reflect on that? What’s your response to watching yourself respond in that fashion? Is that frustration, is that opportunity for understanding where that came from?
Robbie Kaplan (11:09):
Certainly in the moment, I certainly wasn't happy about the fact that my voice cracked, because that's not a great, I mean, I won the case, but it's not a great look or sound in the Supreme Court to have your voice crack the way mine did. I don't think I appreciated that it was the Robbie Kaplan coming through until weeks, if not months later, when I was listening to the audio tape, and I thought to myself, “Oh my God, that's what's happening here.” You know, part of being able to do what I do, and you are right about the pressure and living in a glass bubble. And that is much worse today than it ever has been, given social media and the internet. It's like everything we do at my law firm seems like it's magnified hundreds of thousands of times. So it's very stressful.
And one of the things I've gotten very good at is putting the Robbie Kaplan part of it, the personal part of it, into a box, and only letting it out when I want to let it out. I'm very good at repression, believe it or not, for someone who likes to talk a lot. I'm very good at repressing things that I don't think will be helpful. My wife used to joke that I have this amazing ability to persuade myself that whatever my client, whoever my client was, they were absolutely right. They had done nothing wrong. Their arguments were all perfect, et cetera. And there is something to that. In order to be able to do what I do, I have to be good, very good at screening things out in my brain. And again, another good comparison to my son. My son has Aspergers, and for people on the spectrum, that's the hardest thing they have to do. They're not good at screening things out. Whereas for me, just in order to be able to function day to day, I've gotten very good at it.
Charles (12:44):
You know, most of us are never going to have a job that requires talking in front of the Supreme Court or talking to the Supreme Court. I mean, I get nervous if, when a blue flashing light show up behind me on a highway. What's that like? What's that experience like? Are you now at a point where this is part of, I mean obviously it's part of your job, but are you conscious that, I'm arguing in front of the Supreme Court?
Robbie Kaplan (13:06):
So I only do it once and I'm not necessarily excited about doing it again, given the changes in the court. I think I'll take that one opportunity up there and kind of let it be my record. But you're operating, when you're in, but I still do things in court all the time and in front of juries, and you're really operating, or at least I'm operating when I do it, on multiple levels. There's the level, it's almost like my brain is thinking in 3D when I'm doing it. So, on the one hand I'm thinking to myself, “Oh God.” And I thought this definitely the way in front of the Supreme Court. “Oh God, Robbie, the fates of so many people are resting on your shoulders. This is so high pressure. Everyone's looking at you, excuse my language, but don't f*ck it up.” So that for sure, the entire time I was doing the argument, I was thinking that.
At another level, I remember thinking, we'd done a lot of work to practice for the argument and you do this thing called moot courts, where you do kind of fake arguments. And we must've done dozens of them by the time I got there. And so I was thinking to myself how what was happening in the court either reflected or did not reflect our playbook. So when I got certain questions, was I giving the right answer? Another thing that I had been kind of coached by my colleagues to do is to always look at Justice Kagan, because she's very politically savvy, and to watch how she was reacting to what was going on in the court. Because a Supreme Court argument is very different, because really what you're trying to do is help the justices on your side argue with the justices on the other side.
You're not really, probably unlikely going to persuade anyone of anything at a case like that. But your job is to facilitate the discussion they're having during the argument, which is really what it's all about. So during the argument, I remember looking at Justice Kagan, she was sitting all the way on the far right. And at least in my head, I have no idea if this is true or not, but at least in my head, I remember looking at her and thinking to myself, “Okay, Kagan's still smiling. You must be doing something okay, Robbie. Like, so far you haven't screwed this up.” And then there was another level where, where ideas popped into my head that we had never practiced, and that had never come up before in all of our preparation, but they just kind of popped there. So for example, one question I got at the argument was, how do you explain the difference between 1996, when the Defense Of Marriage Act was passed and signed into law by then President Clinton, and 2013, when I was arguing the Windsor case, and how do you explain this societal difference?
And when DOMO was passed, the House Republicans issued a report that said that there was a moral reason to oppose, I can't remember the exact language, but basically, there was a moral reason to oppose marriage equality and that therefore DOMO was justified. And sitting there in the argument, just in the heat of the moment, I forget the question I got, but I basically flipped that on its head. And I said, “Your honors, what's changed between 1996 in 2013 is rather, oh, here was the word, rather than a moral disapproval of gay people, which is what they said in 2016 in this House report. Today, there's a moral understanding that gay people and gay families are no different than anyone else or any other family. And it's a revolutionary change. It's a phrase that Justice Kennedy used in one of his prior decision called, saying that times can blind us to certain truths.”
So that whole kind of progression literally popped into my brain right there. And I remember thinking for about a half a second, “Okay, Kaplan, you're just going to give this answer. You can't really check with anyone to see if it's okay or not, you're just going to go for it.” And I just went for it in the argument. So you're really, you’re kind of operating in hyper speed on many levels at once. The same thing with the E. Jean Carroll trial. Same thing in the jury arguments. Like, I'll be reading in the closing arguments, I have a written speech I'm going to give, but I'll change that speech based on something I see a juror do, or a look that a juror gives me, or something I see the judge do. You kind of have to have that, when you develop it over time, that mental flexibility
Charles (17:18):
And, you're following an instinct at that point, right? I mean, that's really a gut feel.
Robbie Kaplan (17:21):
Correct.
Charles (17:22):
And then, and given the scope and the scale and the impact of what you're working on, and the cases that you're representing, how do you hold onto that gut? Because, people talk about that, follow your instinct. I think I read something you had said about follow your instinct. But follow your instinct can also lead you to fear I mean a lot of people's instincts are fear, are fear based. How do you hold onto the positive instinct, the the one that guides you towards doing right?
Robbie Kaplan (17:47):
So this is not a very optimistic thing to say, but I like to joke to my colleagues that I have probably the best cynical instincts in the business. And what I mean by that is, if I think someone on the other side has a plot that's trying to work against my client in some way, and I'm not even exaggerating this, it's like a scary way to live your life. 98% of the time, my instinct is correct. And so over time, I've learned to trust myself, because I often as a lawyer will say, this is what they're really doing. And then a year later I'll realize that that's what everyone will realize, that's what they're really doing. And it's that kind of confidence in my own instincts, now I think both positive and negative, that allows me to shut the fear away. I also think in order to be a lawyer, a big part of being a lawyer, and being a a courtroom lawyer at trial, you have to have an ability to shut the fear away. Because it's debilitating. You know, you're there performing, I'm sure actors and actresses and a bunch of other people feel the same way.
Charles (18:46):
Is that a conscious choice? I mean, are you conscious of locking it away?
Robbie Kaplan (18:50):
Yes, definitely. Another one of these moments is, another good example of this, during the Supreme Court argument, as I think I mentioned before, probably the most hostile of the judges or the justices that day was the Chief Justice Roberts. And he was quite angry, I think, not at me, really, but at the idea he could see where the case was going, and that there was going to be a majority to overturn the statute. And at one point he was so angry, at least, again, based on my perception. I can't, I wouldn't swear on a Bible that this was so, but it was what I was perceiving in the moment. He was so angry that his lower lip was shaking, the way people kind of get when they're really mad. And I remember again, in this kind of hyper, hyper space that I was thinking in, I remember thinking to myself, “Okay, I understand you're really mad at me, Chief Justice Roberts, but I'm from New York, and I've had a lot of judges who are a lot angrier at me than this. And that's fine. You have every right to be mad at me. I'm just going to answer your question.” So that really was an instinct of just pushing it away. I know he's mad, I know his lower lip is shaking, but my job here is to argue this case for my client, and that's what I'm going to give.
Charles (19:57):
I mean, this is a cliche, right? And it's a sporting reference point, but maybe it doesn't apply, but it feels like what you're describing is somebody is in the zone.
Robbie Kaplan (20:05):
Yeah.
Charles (20:05):
That time slows down and you are taking all kinds of information and making real time analysis at a very sophisticated level. I mean, is that what that feels like?
Robbie Kaplan (20:14):
Very much so. I mean, it's a great high when you're doing it. Obviously I've learned a lot about kind of neurodiversity with my son and with my family, and my wife and my son are both ADHD, and they go into hyper focus when they're doing certain things.
I've been doing this long enough that I've noticed a pattern that in certain moments of my job, certain kind of high stress moments, I tend to go into a kind of zone where I'm thinking not only very quickly, but at various levels at once. What are the justices doing? Which justice is going to react to what? Like, you're kind of thinking on a multi-level way. Similarly when your at trial, and in particular, I think in the direct exam I did of E. Jean Carroll in the second trial…
And let me break for a second. So the reason I have to explain that is, Donald Trump did not show up for our first trial. And he concluded after the trial that that had been a huge strategic mistake on his part. So he made sure to come to the second trial. And that was literally the first time that E. Jean Carroll had seen Donald Trump face-to-face since the assault in Bergdorf sometime in the spring of 1996. So even though E. Jean is as tough as they come, and even though E. Jean had been focusing on this assault and the ramifications of the assault for many, many months at this point, years, really since the case began, she was upset and concerned and scared, frankly, to see him face-to-face. And we noticed it because we were doing the prep on a Sunday before she was going to be on, and E. Jean is usually one of the most articulate people I've ever met.
And she was having a hard time articulating her words, coming up with words, which is extremely unusual for her. And I said to her, “Is it possible that you're concerned about seeing Trump face-to-face?” I said, when she wrote her book, this is very interesting, when she wrote her book that first told the story about what had happened, after she finished her book, she actually got very sick and was in the hospital for about a week. And I think her body reacts to the kind of, which is not untypical with people who have trauma, she reacts to high stress situations involving what happened with Donald Trump by getting physically ill, or having physical symptoms. And in this case, it was really the inability to speak. So, we used a psychological expert who had testified at the first case, was not testifying in the second case, to actually work with E. Jean, and get her in a space where she could kind of overcome or conquer her fear, or conquer her fear at least enough to be able to testify in the courtroom.
And when I called her, she says, “I didn't really pay any attention to Donald Trump during the trial,” but she says he was staring right at her. And I said, “Ms. Carroll, can you please state your name, and spell it for the court reporter?” And we looked at each other and, as she says, everything just clicked. We started asking her questions and she was able to just ignore the noise, and answer the questions in a really powerful way. The point of that exam was not to repeat what had happened to her. We already proved that in the first trial. The point of that exam was to prove all the incredible damage that had been done to her as a result of Trump's defamatory statements, and the unbelievable, the shocking messages that she received, has received ever since, from all kinds of people threatening her with rape and murder and just really vile stuff. So, I really was in the zone in that direct, because I wanted the jury to see, as clearly as they could, how much E. Jean had been damaged, not only from the assault, obviously, but from the campaign of defamation that had started in the summer 2017 and continues to this day.
Charles (24:12):
You know, listening to you, I'm really struck by the self-awareness you have of your strengths, and you have a lot of confidence in them. And as you know, a lot of leaders can't see their own strength, because they're really worrying about their weaknesses or struggling with some version of imposter syndrome. Is that self-awareness instinctive for you? Are you conscious of sitting down and ever at any point and thinking about what am I really good at? What do I lean into?
Robbie Kaplan (24:35):
I mean, I'm really, yes, I think so. I mean, I know that I'm very good at thinking outside the box as a lawyer, and strategizing with my client about how to get to the ninth inning, as quickly and as efficiently and as effectively as possible. I'm obviously a good writer, but that's mostly because I've been doing it for so long, or a good writer of legal prose (laughs), because that's how I've been doing it so long. You know, when I was at Paul Weiss for all those years, we didn't get in the courtroom very often. You know, I had a few trials at Paul Weiss, but not the way people who are former prosecutors or criminal defense attorneys get into the courtroom. So I had to kind of push myself, starting in the Charlottesville case, really, to take a much more active, much more dominant role at trial than I ever had in the past.
And in fact, I think I did one trial at Paul Weiss where I was the lead attorney, but in most of the trials I did there, I was junior to some senior lawyer. So taking on the mantle of being the senior, first, what they call first chair lawyer at the firm, I mean, at a trial, was something I had to push myself for. And, you know, I realized that I'm actually really good at it. And I think the hardest thing for lawyers and probably for any leader, is you have to find your own style. Especially as women. Like, you can't just adopt the style of some old, you know, guy who's great in court, but has a star, Ted Wells, for example, who's a phenomenal trial lawyer and a friend. When he opens his arms in court, I think his arm span is like nine feet across.
Like, I, obviously, that's not an option for me in the courtroom. So you figure out what you're best at. But I can't, wouldn't be fair to me would not be fair for me to say that I don't have imposter syndrome. I certainly have imposter syndrome, it comes up all the time. It kind of creeps through, and I have to separate, if this makes any sense, my intellectual, what I know intellectually in my brain, from what I sometimes feel in my gut, if that makes any sense.
Charles (26:39):
No, it makes, makes complete sense. When does it show up for you? You figured out what are the triggers?
Robbie Kaplan (26:48):
Thinking. So there are not a lot of women in the law who've achieved, there are definitely some and there were many before me. But it's still not typical for a woman to be a very prominent lawyer. And even though sometimes I know in my brain that I am, and I know in my brain it's because I'm very talented at what I do, and have won a whole bunch of things, there are times in my gut where I worry that I'm an imposter. And I'm trying to think of a situation when that comes up.
It doesn't happen in the courtroom anymore. Sometimes happens, like, in interpersonal things, in meetings, maybe, meetings with colleagues or meeting with other lawyers. I'm often surprised by, honestly, by how people accord me this kind of respect that, in my gut, I don't, I still think of myself as Robbie Kaplan from Cleveland, Ohio, and like, just like when I graduated high school, and so it's shocking to me sometimes. I don't know if I'll ever fully be comfortable with it, to be honest. And one thing that I do in response, which I think is a very common strategy for women, and maybe not the best strategy honestly, is I get very self-deprecatory. So my wife is always kind of castigating me for this (laughs). So, in order to deal with those fears, I think I often downplay myself and act very, very humble. Think I'm pretty humble, but act very self-critical in ways that I probably shouldn't, if that makes sense.
Charles (28:36):
For sure. I mean, having a life partner who's supportive and loving and caring is obviously a huge asset. Are there other people that you go to, to bolster you? Who do you talk to?
Robbie Kaplan (28:46):
Yeah. So I, I've been very lucky, incredibly lucky in my life, to not only have incredible mentors in my career, both men and women, two of whom I still call, I called throughout the trial in Carroll all the time and got advice about things, throughout the whole case, really. And I still call them if I have a particularly knotty issue or I'm trying to decide how to handle something, I often call them. One of my mentors was Chief Judge Kaye, and she passed away several years ago. But, they are still people I go to quite often. And one really nice thing about my old law firm is that was really the culture of the place. Like, if you had a tough issue, you almost always went to go talk to someone older and maybe wiser, at least more experienced, to get their take on it.
To be honest, I'm a little concerned that this generation doesn't do that very much. And (laughs) regardless of what you think about people, maybe you think that older generation and we have worn out views and outmoded views, et cetera. It's without a doubt the fact that we've done a lot more. And I think that has to be, that's a very valuable tool to use, at least I found in my life. And then on top of that, I have just some, an amazing group of friends, lawyer friends, non-lawyer friends, who I will call, again, for any kind of problem, any issue I have. I am not shy about calling and seeking advice, for sure. One of my closest friends is Sharon Nelles, who's head of litigation at Sullivan Cromwell. And I joked to someone the other day, I don't make a serious decision without talking to Sharon Nelles.
Charles (30:22):
So important to have people like that in your life that you can trust implicitly.
Robbie Kaplan (30:25):
That’s of course on top of my wife, obviously, who I consult about everything.
Charles (30:29):
When you are walking into a really high pressure situation, a really big court case, you're taking a deposition from Trump at Mar-a-Lago, for instance. Are you conscious then of putting on a suit of armor or a cloak? Are you conscious of showing up in a different way?
Robbie Kaplan (30:43):
For sure, because I knew that he was going to try to rile me, which he did in both depositions. And I knew that the only effective reaction to that would be to ignore it, to stay above the fray, to stay as courteous and calm as possible, not qualities - well, I hope I'm known as being courteous, but I'm not known as being calm. So these are not qualities that I normally (laughs) exhibit so much in my day-to-day life. And so I had to very much think to myself, “Okay, Robbie, you know, you're going to be as zen about this as you possibly can be, at least externally.” That doesn't mean I was feeling that way internally, but externally, I definitely have to put on a coat of armor.
Charles (31:27):
Yeah, I had a couple of situations where I was very conscious in the moment that I could either collapse under the stress of this or I could choose to see the person across from me in a completely different light. I remember being confronted by a very intimidating man at one point in a very large meeting, and I realized, oh, I'm just going to see him getting up in the morning, having a hard time putting his socks on, making him very, very human. And it really helped me, actually, because it just took all the threat and the energy. I thought, you're just really struggling.
Robbie Kaplan (31:56):
That's really interesting. I've never, I have to try to think of that. With Trump, I have to say, I knew that my calmness, I mean, it was really a fighting tactic, it was a literal suit of armor in certain ways. Because I knew that by staying very calm, being very courteous, it would drive him nuts. So I knew it was a very effective technique, and that of course made me very happy inside, although I didn't show it. So, for example, he has a tendency, I'm sure you've heard him, he really runs on, when he's speaking, he doesn't really speak, he doesn't answer questions in a linear way. He tends to kind of go off in a tangent, and especially here, where he was so angry, he would kind of go off in these long tangents.
And so I would let him go on, you're allowed to stop a witness if they're just speaking about something that's completely unrelated, but I didn't do that. I let him go on. And at a certain point, I would say, and often I did, he would say things that were even worse for him, in kind of his diatribes. And then I would say at a certain point, I would say, “Sir, are you done yet? Because I have another question to ask (laughs).” And it, and it would literally drive him nuts. I mean, it was like putting a red flag in front of a bull.
Charles (33:02):
So I want to switch gears slightly. I talked to Mark Thompson on the podcast when he was running the New York Times about leading from the front. And he talked about the journalist instinct to run towards the gunfire. I talked to Marty Baron after he'd retired from the Washington Post about his leadership of the Post and the Globe. And he talks about the responsibility of being a journalist. You bring a similar sensibility, right? I mean, you've been on the frontline of cases that have enormous implications for the rule of law, for democracy itself. And that obviously comes with enormous responsibility. Where does the willingness to accept that responsibility come from, from you? Because that's not easy on any level.
Robbie Kaplan (33:39):
So, really, I would say two things. One, at least two things. My grandmother, who I was very close to, was the kind of person who never backed down from a principle and from a fight, if it was necessary about a principle. She was an incredibly brilliant woman, incredibly tough, in a good way. And she had a huge influence on me as a kid, and I spent tons of time with her. So, you know, that was kind of instilled in me as a young kid, that you do what's right, no matter what, even if that's not the most popular thing, at least in your, the people nearest to you. Now in today's world, that has taken on a completely different complexion, because we live in a world today where everything you do, or anything you do in the kind of stuff that I do, is magnified instantaneously on social media, and often in the most kind of nutty and irresponsible ways.
Certainly by the MAGA folks, who will comment on me every, you know, every day I'll do a search to see what crazy thing, not every day, probably twice a week (laughs), see what crazy things are said about me, not because I really care that much, because I'm concerned about security and I want to make sure they're not talking about my son or anything like that. But I also think, honestly, some of it for me comes from my religious beliefs. I mean, this is going to sound really kind of nerdy and character. I don't mean it that way. I mean, I have a very serious religious belief system, and it comes from my faith, which is Jewish. And Judaism, you know, there's a very, very strong commandment, really. And it pervades all of Jewish thought, that your job is to repair the world.
That Judaism doesn't really have much of a sense of the afterlife. So it's not about rewards after you die. It's about fixing the world that we're all living in. And so that also is connected to my grandmother, obviously, because I got a lot of those views and culture from her. I was bat mitzvah, believe it or not, in 1970… was it 76? No, 79. And my portion, which is the portion of the Torah that you read, that's what you do at a bar/bat mitzvah, you read the Torah publicly, at a service, was Deuteronomy 16, which is, it's called Judges. And it's about creating a civil court system. Deuteronomy is all about, now that we're, the Jews, are out of Egypt and have arrived at the Promised Land, how do they create a society? So in a certain ways, Deuteronomy is really a book of politics, and of how you create a society where you are your own leaders, which was very different than the way the Israelites and the Jews had lived before that.
And so in this chapter, Judges, it talks about creating a judicial system and creating, having judges, and the rules for judges. And it says this a very famous line, “Justice, justice thou shall pursue.” And I don't know, it that just seems to be part, I mean, it's lucky, just pure luck, (laughs), that that was my bat mitzvah portion. But it seems to be a real fundamental part of me. And I think in 2016, when Trump was elected, and I was very concerned then, although not nearly as concerned as I am today, but very concerned then about the threats to our system and our democracy and our constitutional republic. I thought to myself honestly, what Rabbi Hillel said, just after the destruction of the second temple, which is, “If not now, when.” Same thing with Charlottesville. Like, if no one else is going to do it, I guess I will. I can, I mean there's something a little crazy about that probably, because maybe, you know… I mean, I'm not sure I really understood that I could change things, but I thought to myself, “I'm going to try.” If that makes any sense.
Charles (37:42):
And you do you see now that you can and that you do?
Robbie Kaplan (37:45):
Yeah, I have, although I have to say like, you know, they just came out yesterday, as we were driving out, I was driving out here, there's a new list that came out of writers who are Zionists, which is really quite scary and quite totalitarian and fascist in certain ways. And I thought to myself, I was in a car with a friend and we were talking about it. Have we really gotten to a new, very, very scary place, that didn't exist, you know, even in 2017 when I started the law firm? Like, the idea that we're going to start having lists of people who should be condemned as Zionists, I don't want to get into the politics of whether you're a Zionist or not, is, I think you know, a combination of social media and Donald Trump, has really brought our society to a place that's quite scary.
Charles (38:44):
No, I agree. I have two thoughts on that. One is, I interviewed Senator Gillibrand last week, and interestingly, you may know this already but, she talks about both her faith and the influence of her grandmother on giving her the need to serve.
Robbie Kaplan (38:56):
Oh, interesting. Because her grandmother was that very big Albany politician, I remember, a fixer, kind of.
Charles (39:03):
That's right. And I think to your other point about society, it strikes me that our generation, we're of similar age, but our generation has never had to actively fight or anything, right? I mean, you know, I'm English, obviously. My parents were kids in World War II, my grandparents lived through them, my grandparents fought in it. And those generations recognized what was important and had to literally risk their lives. I mean, I think there are versions of that, for sure, but I'm conscious of the fact that we haven't really had to fight very hard for things that really matter to us. And maybe this is the time that we have to do that, and hopefully not physically, but finding the courage to confront difficult issues.
Robbie Kaplan (39:41):
I think that might be right. I think about that, I think about it similarly a lot. Because I grew up in the Reagan era. And everything was kind of boring. Like, I remember thinking of a kid, like, it's just, everything's boring. And as a kid, I didn't like the fact that it was boring. Sometimes today, I think to myself, I really wish we could go back to the boring period again. And I remember reading about, obviously, about World War II and hearing from my family about World War II and the Civil Rights Movement and all that stuff, and thinking, “Okay, we kind of solved that. Like, we're now in boring period.” But boy, I could not have been more wrong.
Charles (40:13):
Yeah. Boring is really appealing now.
Robbie Kaplan (40:15):
Yeah. Agree completely.
Charles (40:17):
How do you choose your next case? What do you still want to learn and find out about yourself?
Robbie Kaplan (40:22):
So I, you know, we try, we try to choose, I mean, obviously continue to represent a whole bunch of clients all the time. But in terms of my next kind of, what I would call my public interest docket, I'm really concerned about and very interested in bringing a case or cases that deals with a horrible problem of misinformation and disinformation, on the internet or on social media. And it's very hard, because we have a law in the United States called Section 230, and that gives social media companies a lot of leeway, to say the least. It's a kind of immunity for them in terms of what is on their websites. But if you look at the data, especially for kids, what the algorithms are programmed to do in connection with the brains of kids, is truly quite scary.
And so, I can tell you that I'm looking at that right now. I hope to be able to bring a case in the near term. I think something has to be done about it. And Congress doesn't seem to be able to do much right now. I hope they pass - there's some bills that are before them. Maybe they'll pass one or two. I sure hope they do. But it seems to me that if we can't agree in our society about what is true and what is not true… I'm talking about philosophy. I'm talking about basic facts, like global warming or the efficacy of vaccines, I don't know how we continue to function as a democracy. I just think it's the single biggest threat. And that's in a world in which there are a lot of threats.
Charles (41:59):
Yeah, we can talk about that as a subject of a whole separate conversation, couldn't we? That's such an important topic. Knowing what you know now, if you could go back 30 years, what advice would you give to that younger version of yourself?
Robbie Kaplan (42:13):
So I think I would say to myself, “Trust your guts more than you do.” I was very much someone who, you know, I went to Ivy League schools, and I thought I just had to check all the boxes and do everything that was traditional to do. And that very long, very steep ladder was the only way to achieve success. And I climbed that ladder and I succeeded at it, but it was a lot of years of working insane hours, and putting things off. I think I would say that. And so I would say to myself, like, “Go with your gut more. You know what's right. You know what's wrong. You know what you're good at. Don't feel that you always have to follow the established protocol on everything in order to achieve what you wanted, in order to be able to achieve what you wanted for yourself, but for the wider good.” If that makes any sense.
Charles (43:06):
Do you have any regrets? Obviously you're, hopefully you're not anywhere close to being done, but as you look back so far, do you have any regrets?
Robbie Kaplan (43:13):
I regret I've long regretted never being a prosecutor. I'll tell you a funny story. So I had wanted to be a federal prosecutor doing white collar work, which is a very common kind of career path in my field, at least in here in the States. The crazy story is, I got a (laughs), I got an internship when I was in law school to work at the US Attorney's office for the Southern District of New York. And this was during Bush One. And the questionnaire had a few questions that concerned me. There were questions about being gay, which back then they thought was a serious problem, and that obviously concerned me. And they had questions about pot. And this is, I was in law school, so I was just out of college. And the questions were, one, have you smoked pot? And two, how often?
And so I went to get some advice from one of the professors at the law school, I'm still friends with today. And he said, “Well, the way to answer that question is, yes, experimentally.” So I wrote, ‘Yes experimentally.’ And the next question was, how many times? I wrote, ‘12 plus,’ (laughs), and my job offer was rescinded (laughs) from the US Attorney's office. You know, I guess I like to experiment a lot when I was a kid. Honestly, at the time I remember thinking to myself, I don't want to lie. Like, what if they ask a friend? I don't want to ask a friend to lie for me. So I never made it to the US Attorney's office to be a prosecutor. And I've long regretted that. I kind of think like a prosecutor, I think, in terms of how I work. So I'm kind of a private prosecutor in a lot of ways, and that's just fine.
Charles (44:45):
And as you look at the future, what are you hopeful for?
Robbie Kaplan (44:55):
On the one hand, this young generation, and I see them a lot because of my work for Columbia University, has a greater, deeper sense of justice than I think a lot of generations before it. I was just thinking about this the other day. It's just actually amazing that so soon in this year, 2024, it's absolutely inconceivable to anyone in college, or my son's age or younger, to say anything that is homophobic or racist or sexist. And not everywhere, but in large portions of our society, it's just become completely not cool. And that's a very good thing, because that obviously didn't happen. Like, you watch movies now from the seventies or eighties, and it's not that they're not great movies, but sometimes it's pretty shocking what people will say. What was it?
I remember watching a movie with my son when he was little, I’ve got to think of what it was. But it was so homophobic and so transphobic, and I kind of wanted to turn it off, but I knew that would be a terrible fight with my son (laughs). So I had to explain to him afterwards what the problem was. But it really is, you just don't find that today in popular culture, and that's all for the good. That's a very good thing. On the other hand, I think this generation suffers from a failure to see complexity, and thinks that things are simpler and easier than they are, and that presents problems, too. So my hope is that they will grow up a bit. People are going to hate me when they hear that (laughs), grow up a bit, and understand that the world is a very complex place, and problems often don't lend themselves to simple, easy solutions. And if they do that, which I'm confident they will, with their hearts in the right place, I think there's a lot of hope in that.
Charles (47:08):
And last question for you. As you look at the future, what are you afraid of?
Robbie Kaplan (47:15):
Where do I start? I'm afraid of the loss of democracy, at least in the States, or at least the loss of democracy as we have experienced it. The loss of a president who, every president has before, other than Donald Trump, who, when they lose an election, voluntarily leaves office. I worry about the stuff about social media and misinformation and disinformation, including by foreign actors. You know, I think there's a decent amount of evidence that China and Russia right now have made the problems on campuses much, much worse than they they need to be, and that's not a good thing. And I worry about the peace in the world. I mean, again, when I was a high school kid in the eighties, it never occurred to me that we would have a war in the Ukraine and Europe. That hasn't happened, you know, really since World War II, to the degree that it is now. And it's petrifying the people of Ukraine. And wars in the Middle East, I mean they've always existed, but what's going on now is also pretty scary. So sadly, there's a lot to worry about. Not to mention, God forbid, another pandemic.
Charles (48:27):
I really want to thank you for coming on the show. I'm conscious we could talk for hours about many aspects of leadership and life, but you have people to defend and cases to win. So I want to thank you, honestly, on a personal basis as much as anything else. One, for being a reference point about what's important, and two, about being an inspiration for what's possible. I think we badly need you—
Robbie Kaplan (48:50):
Oh, Charles. Thank you.
Charles (48:50):
We badly need you, and people like you, now more than ever. So thank you, Robbie.
Robbie Kaplan (48:55):
Wonderful, thank you.
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