Roberta Kaplan Will See You In Court
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On September 28th, the Global Citizen Festival will gather thousands of people who took action to end extreme poverty. Join Post Malone, Doja Cat, Lisa, Jelly Roll, and Raul Alejandro as they take the stage with world leaders and activists to defeat poverty, defend the planet, and demand equity. Download the Global Citizen app today and earn your spot at the festival. Learn more at globalcitizen.org slash bots. It's on! It's on!

Hi, everyone, from New York Magazine and the Vox Media Podcast Network. This is On with Kara Swisher, and I'm Kara Swisher. Today, we're going to talk to someone who's not tired of winning, and it's not Donald Trump. It's attorney Roberta Kaplan, who many know as Robbie Kaplan. In January, a jury awarded Kaplan's client, E. Jean Carroll, $83.3 million in her defamation case against Trump.

It was her second win against the former president. Last year, a different jury found Trump liable for sexually abusing Carol in the 1990s and awarded her $5 million in damages. I talked to Kaplan on Friday, February 16th, just hours before Trump was dealt another blow in a New York court, this time in the civil fraud case brought by Attorney General Letitia James. A judge ordered Trump to pay a $355 million penalty plus interest for inflating his net worth to secure favorable loans.

Since that ruling hadn't been announced yet, Kaplan and I didn't talk about it. But we did discuss her own trials against Trump, as well as the rich arc of her career, including arguing the Supreme Court case that struck down DOMA, the Defense of Marriage Act, which helped lead to marriage equality. In 2021, she also helped win a civil damages suit against white nationalists who organized the Charlottesville Unite the Right rally. And right now, she's in a case against X and Elon Musk. So

So we've got all that, plus a question from lawyer and activist George Conway after the break. Roberta Kaplan, thank you so much for joining us. It's a pleasure.

So, we've known each other a while, haven't we? I don't know quite when we met. Probably around the marriage, gay marriage thing. I'm trying to recall. Yeah, I think it was at some conference years ago. I have vague recollections. Your mom was with you that much, I remember. Oh, well, she's still with me. But it was about gay marriage. It had not gone to the Supreme Court, I believe, and it was headed that way. And we're going to get to that and more. But let's talk first about, obviously, the news, which is this verdict that you got $83.3 million. It's a big deal.

Talk about what it means. You've had a couple weeks, I guess, to reflect upon it. I'd love to know what you think now. So it's interesting. I was actually with E. Jean yesterday, and we kind of spent the day together at her house. It's the first time I'd ever been there. And we were kind of both...

remarking on, I mean, really just kind of processing the fact that when we got the first verdict, which was actually where the jury found that he had committed the sexual assault, it didn't really get that much play. Right. And we now think that the reason for that was because it was only $5 million. Right. But

The 83.3 obviously served as a wake-up call, not only to Trump, I think, but also to the people who are kind of watching all this. And they realized then that this was a big deal. That things have a price. Correct. So for people that aren't, the jury awarded Carroll $7.3 million for pain and anguish, $11 million in reputation repair, and $65 million in punitive damages. Talk about...

Talk about the last number. Were you surprised it was that high? And what does it tell us about the jury's view of Trump's behavior? This is a measure of intended malice towards Carroll, right?

Yeah, so I thought it would be high. Before the trial, I don't know if I would have thought it would have been this high. But the problem for Trump is that his behavior during the trial was so atrocious in various ways that he almost gave the jury no choice. It's almost like he was daring them to do it, taunting them. And that included behavior from openly disrespecting the court and the judge in the courtroom,

to being in court, leaving the courthouse, doing a press conference where he continued to defame E.G. literally during the trial, to, I think my all-time favorite is he recorded a video, I think it's a video, where he said, I'm going to keep on doing it, this is, again, during the trial, a thousand times. You can imagine I emphasize that a lot in my closing. So I think the jury...

I mean, it's hard because we didn't get to talk to them and I don't think we ever will. I don't know who they are. But I think they were offended by the open contempt kind of of our system, our judicial system, our democracy, the rules, the prior jury's verdict, et cetera. So he really brought it on himself, I have to say. Would you say he did that...

On purpose? Because obviously fundraising is part of his ploy with all these court cases, isn't it, a new fresh thing? Was that a beneficial thing for him to do despite this verdict?

So it's very hard for me to get inside his head. I think he thought it was going to be beneficial to him. He kind of sees it as a strategic benefit to him politically. I can't imagine even putting aside the personal issues for him of having to pay $83.3 million. I can't believe that had he known that it was going to result in a verdict that high, he would have thought that was good for him.

Right. But again, I don't try to get into his head. Well, if he gets to be president, that is good for him, right? I think, I assume that's the figuring he's doing. Now, Trump's team has already motioned for a mistrial, which has been denied. The judge said the request, quote, made no sense. Trump has also said he'd appeal. Can you walk us through what happens? Everyone doesn't quite understand in terms of

We'll get to the cash in a minute, but walk us through what happens next. So what happens next is the judge issued the judgment last week. That means Trump has 30 days, and this gets a little bit to the cash, to either post a bond or to deposit the judgment number with some extra money for interest with the court.

I don't think a number that high has ever been deposited with the SDNY, but it's potential here. Then they will appeal to the Second Circuit, both in this latest trial and the earlier trial. I think their appellate issues are very, very, very weak.

Judge Kaplan's a very strong judge. Most of their arguments are evidentiary. He knows very well how to rule on evidentiary issues. I give them extremely low prospects on appeal. And what happens to the cash? So if he does a bond, he has to pay less or he has to just guarantee it? Yeah, if he does a bond, he has to pay less. He has to put up 20%. To the bond people. To the bond people. And then they're on the hook for the large amount. And he has to give them some collateral, but they are on the hook.

Interestingly, last time when the verdict was so much lower, the $5 million, he did not post a bond. He actually deposited the money with the court and then

I'm embarrassed to say how long, 30 some years of litigating. I've never seen anyone do that. Oh, why? Tell me why. Because most people would rather only put up 20% than put up the entire amount. So like he put up, rather than putting up a million dollars on the last verdict, which is all it would have cost on the bond, he deposited $5.5 million with the SDNY. And why is that? Why do you imagine? Do you have any idea? Yeah.

Why did he have to do that? Yeah. I suspect it's because he couldn't get a bond. Oh, interesting. That whatever questions the bond companies were asking, either he didn't want to answer or they didn't like his answer. They didn't like his answer. So then what happens? He goes to the appeal. He loses that, say. Let's assume he'll lose that. Where does that go then? Um...

Theoretically, I'm trying to think of it. Theoretically, he could try to ask the Supreme Court to take the case. Either case, there's really not much left by way of federal issues that the Supreme Court could legitimately take. They would probably, he might probably try to come up with something that would be a legitimate question of federal law for the Supreme Court. The chances there, again, because it's mostly state issues of defamation law, of sexual assault law, etc.,

is even lower than the chance of winning at the Second Circuit. So almost negligible. And what would that mean in this appeals process? Because it takes a while. He could be president when you're doing this, correct? He has no ability to get out of it, even if he was president. If he is elected president, he will be president when the appeal's happening, for sure. It'll take about a year or two years. Under our system, I'm going to sound super

kind of freaky and nuclear right now. Under our system as it currently exists, there is nothing he can do. He's already said as president that he's willing to consider measures that are pretty inimical to our democracy and our democratic system. So I guess theoretically, he could tell the Second Circuit that he's not going to stand by, he's not going to honor their decision or I don't know, or just refuse. Then what happens?

Well, again, up until this point in time, up until 2024 in American history, court decisions and judgments and appellate decisions always got enforced because people respected the legitimacy and the authority of those systems.

I don't know. I mean, if we're in that kind of situation, arguably, we had much worse problems on our hands because we're almost in a situation of losing our Democratic or Republican form of government. So he could just refuse? Just refuse. Could they arrest him? Yes. But again, as president, who knows what he'll do? Right. Right, right, right. Wow. Okay. I mean, again, if we're ever in that place, I think our problems are so much worse than E. Jean Carroll's judgment that

That's a fair point. That is a fair point. Still, she won, right? So I want to talk about, to back up a bit and talk about the trial, your team's strategy at the trial. You said his behavior gave the jury no choice. He brought on himself, but he didn't do all the work. As you prepared for the case, what was your plan to win it? And were you as confident? He obviously gave you an assist in some fashion. What we really had to think about and spend a lot of time thinking about is the difference in our theory between trial one and trial two.

Trial one was really about persuading the jury that,

that this sexual assault that happened a long time ago, the spring of 1996, actually happened. And doing everything we could to buttress the credibility of E. Jean's story, we used people like Natasha Stoyanov, Jessica Leeds. We brought on the two outcry witnesses or the two women, two good friends of hers who she told right after it happened in 1996. It was really all about that. And the defamation was kind of secondary because we knew in order, we had to convince the jury that it had happened before we'd ever went on defamation.

This trial was very different. This trial was not only not really about the defamation because the jury was ordered to assume that what Trump said was defamatory, it was about the damages. So this trial was really focused, I would say, on two things. One, the unbelievable swamp, that's an understatement, of hate crimes.

and threats of violence that E. Jean has constantly received ever since Trump originally defamed her back in June of 2019. And some of it, it was just shocking. I mean, I have pretty thick skin, but shocking even for me. And so we put a lot of that on and explained it to the jury. And I think the jury, having looked at their faces, was pretty shocked. And second, that this trial was about...

His contempt for

for the rules, his view that the rules don't apply to him, his disrespect to the first jury verdict because he continued to do it. By the end, it was probably more about that. And you really have to kind of think of what he did, at least legally, I understand the political points you made, but at least legally, it was kind of an anti-strategy, right? If our strategy is to show that this guy's a bully who can't follow the rules, thinks the rules don't apply,

To actually show up in court, which he did, and act like a bully and act like the rules don't apply, it was kind of, from a legal perspective, it was literally insane. You should have sent him a gift basket, I guess. But did you, without, if he had behaved, what would have been the strategy? I think we still would have won. Our strategy would have been the same. I think we still would have won. I don't think the punitive damages number would have been as high as it is.

So he gave you that gift of showing what you were saying he was capable of. Correct. When I was doing my closing argument and he walked out of court, which I didn't even see the judge, I didn't know about until the judge said something, I thought to myself, well, that's another $10 million. Oh, wow. Right there. Right. Because he's doing it. Yep.

Yeah. And he couldn't contain himself. Do you have any idea why he did it? I mean, obviously not in his head. Would have there been any plus for doing that? You know, this is ridiculous. I would assume that was what went through his head. Yeah, I think, I mean, again, it's very hard for me to get into his head. I think part of it is he thinks his followers like it, and that's surely true. They kind of like the open kind of teenage boy thing.

behavior, which is what he was engaging in. So there's that. On top of it, Judge Kaplan, pretty early at the trial, the second or third day when kind of Trump was talking back to him, Judge Kaplan said, you can't control yourself, can you? And I think that was true too. I just think he, and he seemed pretty subdued for some of it, but there were just moments when I literally had the impression he could not control himself. He physically couldn't control himself. Which by the way, one more thing, Kara, that's really scary.

Think about it. If I'm right about that. Impulse control. Yeah, the idea that this guy would again be the commander in chief of our military is petrified. Yeah, well, that's what the generals have said. His generals, as he used to call them, said that's the problem they had with him. So every week we get a question from an outside expert. Today we have one from a fellow lawyer you know quite well. Have a listen. Hi, Robbie. It's George Conway.

I heard that there has been a lot of public discussion recently about older men and the extent to which their memories deteriorate over time. I'm not sure where I heard that because I'm getting old, but it reminded me of the fact that at Trump's deposition, Trump seemed to have forgotten what his second wife, Marla Maples, even looked like.

You showed him a photograph of E.G. and Carol, and he mistook the woman in the photograph as being Marla Maples. Now, it's obviously not unusual for people to have failures of recollection when testifying. But that one struck me as, while being a well-meaning misrecollection, it was totally and completely bizarre, right?

And frankly, a bit disturbing to the point that if I were charged with managing Donald Trump's mental well-being, and thankfully I'm not, I'd want to take him to the nearest geriatric neurologist. Were there any other instances of bizarre testimony from him at his deposition? You know, stuff other than the self-serving kind of thing that you normally expect to hear from somebody, right?

Who's a complete liar. Okay. Talk about that deposition and what George is asking. Yeah, so the short answer to George's question, and as people may or may not know, George is the person who told EG to call me in the first place. So he has a key role in this whole story. To answer his question directly, the answer is yes. And I would say it came up in two different ways. One, going back to the question of impulse control,

he couldn't really control himself with me at the deposition. So it was not only a constant barrage of insults to E. Jean, who wasn't in the room. There were a lot of insults to me. So at one point he said, when he was talking about not my type, he told me that I wasn't his type either. He told me that he was going to sue me very strongly, whatever that means. He told me that I was a disgrace, et cetera, et cetera. Okay.

Really, I'm going to be honest here. I'm not someone who's known for their equanimity. I'm just not. That's not how I'm wired. I can attest to that. Not how I'm wired. But for some reason, I knew it was important to stay calm. And so I just did. I just let him keep saying it. And he would kind of go off. He does this a lot in all the different cases. He kind of goes...

on a tirade, like on a speech or flies and answering questions, which is never what you want your client to do. And I would just kind of look up after a while and I would say to him, are you done yet?

Because I have another question to ask, which of course drove him completely insane. Right, so you didn't react, that you didn't, the non-reaction was a strategy, presumably. Correct, correct. And I have to say, it took a lot of impulse control on my part, but I managed. And two, there were other lapses of kind of cognition and memory. The most important one is, so one of the arguments he was making is that this assault never happened, right?

His strongest argument was the fact that E. Jean does not know the precise date. And that is true. We know it was in the spring of 1996 because of what her job was at the time. We know it was a Thursday because Bergdorf Goodman only stayed open then on Thursday evenings. So we have some details, but you cannot say, no one can point to a Thursday evening in the spring of 1996 and say that's when it happened. So his point was, well, if she doesn't know the exact date, it didn't happen.

The problem for him with that is there were a whole bunch of other things he didn't remember. The key one being he didn't remember his anniversary with Melania. He didn't remember anything about his wives, how long he'd been married to any of them,

when he got married to the next wife. And from a key perspective, I said to him, because he was making this point about how Eugene is lying because she doesn't remember. And I said, so what's your anniversary with your current wife? And he said something like, I'm not going to dignify that with an answer. Did that strike you? Or was he being, because you could be just obstreperous or you could really have a neurological issue. Well, it also,

It also could be that he just doesn't care about his anniversary with Melania. Like, I'm not 100% sure what it was, but it was very clear he didn't know it, and he was using the, I'm not going to dignify it, kind of as a defense to the fact that he didn't know it. Right, right. Now, one of the stories you told George, actually, on a podcast was this, when he started insulting you, he seemed to be focused on any woman that challenges him, right? I would assume, because it seems that that's a pattern for anyone who's paying attention. Yeah.

And his lawyers set this up. Can you tell this story? And I will say the actual words so people know. I know you couldn't say it on cable news. You don't have to. But put the story up for us. The story, the insulting me at the EG deposition, the saying I'm not his type or the other one? No, the other one. Okay. So the other one is a different case, just to be clear. It's a case in which we sued Trump.

and his corporation for basically engaging in a pyramid scheme or fraudulently promoting a pyramid scheme called ACN. And in the fraud deposition, it was a very different deposition. I was just, our evidence is so strong in that case that I just wanted him to confirm, yeah, this is my signature on this contract. Yeah, that's me in that video. Yeah, this is what I said here, et cetera. So he kind of realized that as the time went on and was super confident

irked by it because I think he also realized as time went on that we had a very strong case so there were two episodes of him kind of completely losing his temper well maybe one of losing his temper and second of being insulting the first was at about 11 30 in the morning um I said to him I didn't know what to call him so I decided to call him sir so I said okay sir

I've got one more topic to cover. And then how about if we take a break for lunch? And he said something like, why do we have to break for lunch? This is a waste of my time. Let's just go straight through. I don't want to break. And I said, look, if it were up to me, that would be fine. But there's a court reporter, there's a videographer, they're entitled to a lunch break. We have to have a lunch break. And then you could kind of see his brain, like the gears in his brain turning. And he said to me,

well, you're here at Mar-a-Lago. Where do you think you're going to get lunch? And I said, I have to admit, I kind of knew this was coming. I kind of enjoyed this. I said to him, well, I actually spoke to your counsel about this yesterday and they very graciously offered to provide us with lunch. At which point he was so pissed off that there was a huge pile of business documents in front of him. And he basically threw the documents across the table and then started screaming at his lawyers. Wow.

And I'm not going to repeat what he said, but it wasn't pleasant. Ultimately, they did provide us with lunch. And so everything went on fine. But it was, you know, our son is now almost 18. And I haven't seen him do anything like that for many years. I mean, it was really like a toddler. Then at the end of the day,

We probably ended the deposition around four o'clock in the afternoon. And he said something like, we came back in the room. Usually at every deposition, you give each side a chance to see if they want to do anything else on the record. And we came back in and we said, we're done. And they immediately said, off the record, off the record. You could tell that they kind of had a joke about it. And he looked up at me and said, see you next Tuesday.

For this, I am incredibly grateful for my utter ignorance. I had literally no idea what that meant. And so I said to him, what are you talking about? I'm coming back on Wednesday. Yeah. Which was when the Carol definition was. Yeah. And then I didn't know anything until we got in the car. Yeah. And my colleague said to me, who are much younger and hipper, said to me, Robbie, you know what that means? And I said, no. They told me and I said, oh my God, I'm so glad. Because I would not have kept my equity

equanimity. I'm going to say it. It's a C with a C-U-N-T, which is cotton. He called you a cotton, right, essentially. So, which is his way, that's perfect insult that he would think is really devastating to you. Yeah, you could tell they'd been joking about it. They thought it was like, you know, again, like young boys would joke. I'm pretty sure that had I understood it, I would not have been able to keep my calm

demeanor. I'm quite sure I would have gotten angry and said something. I would have made a record. I probably would have brought the transcript back on the record and made a record so I could use it with the judge. Right. And in fact, when we got back...

When I realized, I said to everyone, check the record, check the video, see if we have anything. And everything was off. So we had no documentary proof of it. There were a lot of witnesses in that room who smuggled it. Right. And then you just let it lie. Yeah. Yeah, let it go. When he announced he would show up in court, so based on all this behavior, when he announced that he would show up in court, people were saying he would treat the child as sort of campaign appearance and then would spin it to his advantage. Do you think it did? Did you have a sense it could? Were you worried about that?

Well, the thing we were most worried about, Cara, is E. Jean. This was the first time E. Jean was going to see Donald Trump since the spring of 1996. And I was very worried about her reaction to it. And in fact, as we were preparing her to testify, you know, you do it in a case like this many, many times. And I think this was the Thursday afternoon.

before trial was supposed to start the next Tuesday. And we were doing a prep session in my office and she almost lost the ability to speak. Like you could tell she was in really bad shape. And she's an incredibly articulate human being, as you can imagine, in her own unique style. And she also said she wasn't feeling good. About two weeks before that, during the prep, I had said to her, look,

what about getting the psychological expert we used last time, who's an expert on trauma and just a wonderful person, and having her come in and be in New York during the trial? And E. Jean being kind of the Midwestern Indiana person that she is, said, that's ridiculous. I don't want her here. No way, don't need her. And so I kind of let it drop. But that night after this prep session where she really couldn't talk, I said to her, look, you know, E. Jean,

after you wrote your book, you got very, very ill. Her book in which she told the story about Donald Trump and you actually had to be hospitalized. I said, and now you're telling me you feel sick, physically sick. I said, maybe you should talk to Dr. Lebowitz. I said, I think it might be a good idea because I think you're stressed about the trial and I think you're stressed about seeing Donald Trump. And so she agreed at that point. My logic at that point was strong enough to convince her.

And she had a long phone session, I think, with Dr. Lebowitz. And then by the time she got to trial, they talked about strategies. And then by the time she got to trial, she was fine. What she said is that the minute I started asking questions, she was fine. Right. So that was the number one concern from our perspective. It wasn't even about the strength or what it would do to the trial. It was about what it would do to EG. In terms of the trial, I think...

trying to remember because there's so much going on at this point in my head every minute. I think my gut feeling was if he showed up, that would be good for us. We would get more money. I don't think I ever thought $83 million, but his behavior in court, particularly in a case in which we're saying this is a guy who can't respect the law and respect the jury verdict, would only...

in near to our benefit. We knew that there was very little that he could say. That's the crazy part about it. This really has come out and I should explain. Because of the earlier verdict and because of this principle known as issue preclusion or collateral stoppage,

He was not allowed to show up at the second trial and say to the jury, I did rape her. I didn't do it. I didn't do it. I didn't defame her. He couldn't do any of that. So you have to think about, again, from their perspective, any good lawyer, I'm sure Lena said this too, any good lawyer would say, don't show up. There's nothing you can do to help yourself.

But he showed up anyway. Showed up anyway. So assess their legal team because she might have said it to them, but she seemed like also as ridiculous as he was. So look, on this, you know, I'm not in the business of criticizing other lawyers. We all live in a tough environment and so I don't generally do that. I have to say...

So Judge Kaplan is a very strict judge and is very formal about how he operates the courtroom and is very strict about the rules of evidence. It was painfully clear that Alina Haba, who has not, I think, done many trials and certainly many trials in federal court before a judge like Judge Kaplan, didn't have enough experience to do simple things like how to get a document into evidence.

I mean, at a certain point, it became very painful, at least even to watch. When she was cross-examining E. Jean, she really couldn't get any documents in. And at one point, she said to the judge, judge, will you help me? Which is a weird thing to say to this judge. And he said something like, well, you just saw Ms. Kaplan. She got like 90 documents in when she put E. Jean on direct. Didn't you watch her?

So it was very awkward and uncomfortable. Right, right. So not experienced enough. Obviously, she's not also part of the next part, correct? Is that correct from what you can tell? I don't know. It's unclear to me. Yeah. On the appellate part, he said he won't be using her, but that's not surprising. Would you have given her any advice except not to take the job? So my...

The guy who was my mentor, a guy by the name of Marty London, back at my old firm, Paul Weiss, used to always say his motto as a lawyer was don't make your client's problems your problem. And I think when it comes to Donald Trump and his lawyers, it's hard to imagine a more apt phrase or better advice. There were times in that courtroom where he was clearly directing her to do things that she knew she shouldn't do. And she did them anyway.

And quite frankly, she's very lucky that Judge Kaplan didn't do much worse. He could have sanctioned her, and I think he was tempted. So that's what I would have told her. But I understand in that circumstance, with this guy as your client sitting next to you and passing notes, et cetera, it was very, very hard. Very hard. Joe Takapina, who did the first trial, and that's maybe why he wasn't doing this trial, but he...

made it very clear that there were things that he wasn't going to do. Right, and that's why he wasn't here, which he wasn't here. Much more experienced lawyer, by the way. So one of the things he's doing is turning the Carroll verdict into more evidence for his base that he's a victim of a witch hunt. Some pundits reporters said that Trump's support will drop when he starts to get more coverage. When we see more of him in these trials, I want to get into upcoming ones. You've watched two juries evaluate him up close.

Do you agree with that prediction or is it a benefit of what he's doing here? Given he's lost, he might as well make hay out of it. So I think it depends who his audience is and how he wins the election. And I'm no political expert. But for his base, for the people who show up to his rallies, this is a net positive. The problem is I think he's deluded himself into thinking that the world...

consists of people who show up at his rallies. And even if you look, the composition of the jury between trial one and two were very different. Trial one was almost all people from Westchester County and up. We had Westchester, we had Orange, we had Putnam County.

We had a guy on the jury who got on to my great dismay, who listens every morning, I think, to Tim Pool's podcast. This was not a New York City Democratic. I'm sure many of them are Republicans. Many of them probably voted for him. And even that jury, the verdict was lower, but they held unanimously that he had sexually assaulted her.

Right. The second jury. Red parts of the state. Red parts of New York. Yeah. I mean, again, when I heard that guy, we had thought he had said Temple during jury selection. And when I realized it was Temple, I almost had a heart attack. Yeah. This is a right-wing blog, podcaster, et cetera. Go ahead. Who said really nasty things about E.G. Carroll, by the way. Yeah.

The second jury, in large part because it was a snow day, there'd been a snowstorm that morning, so people from Orange and Putnam couldn't get in. So the second jury was much more Manhattan, Westchester focused, and obviously that you know what they thought of him. But I think the crucial fact is neither group

thought that his behavior and his antics and his defense was in any way okay. Right. And so I'm not smart enough to tell you which swing states he needs to get and which he doesn't get. But I think the more outrageously he acts, the more he ends up alienating anyone other than people who show up at Magarellas. We'll be back in a minute. We'll be back in a minute.

Okay, I want to talk then about how this might apply to the other cases, because this was a big win. It was a huge and enormous win, and the first one of many trials to come. Even if he appeals it, he lost it. You've beaten Trump in court twice now. Plenty of others are hoping for the same success. He is facing 91 felony counts. The trial in the New York case concerning Trump's hush money payments to Michael Cohen, one of his four major criminal cases, is set to start in the end of March.

Your case is a civil suit, but still thinking ahead of next year, is there a strategy that could work in some of these other cases against Trump? I think the single biggest factor, and I'm sure every one of the prosecutors and judges is already thinking about this. In the first trial, we asked Judge Kaplan for an anonymous jury, but we didn't ask for it to be as unanimous as he made it.

In this trial, each juror had a number. Judge Kaplan said that he did not know who they were. There were only two people in the entire court system who knew their names. There were security precautions that were put in place to bring them to the court in the morning and take them away from the court in the evening so that no one would know where they lived. And I wasn't happy about it at the beginning because I was like, this is going to make jury selection harder. And it did, i.e. the Tim Pool guy. But...

In the end, I think those assurances that the jury knew that no one would be able to dox them or harass them or bug them, it was the single biggest factor in having them stand up and do what they did. At the end of both trials, Judge Kaplan told the jurors that they could contact us if they wanted to.

that he would very much, he was ordering them not to say anything about the identity of anyone else who was on the jury with them. And he then went a further step and said, and I would advise you, if you were asking me,

I would advise you never to let anyone know you were on this jury. Wow. And did anyone contact you? I've never been contacted so far. By anybody. Because they're scared. They're scared. So we're also taping this on February 16th. Fulton County DA Fannie Willis, one of the prosecutors in the Georgia election-infused case against Trump, testified yesterday Trump's attorneys are trying to have her disqualified for her past romantic relationship with the lead prosecutor she hired for the case. Okay.

I love your thoughts on her testimony. She said, I'm not on trial no matter how hard you try to put me on trial. Was that a fear of yours that you would have been put on trial? And what do you, how do you assess how to get out of this kind of mess? And it's a mess. So it was a fear of mine, certainly based on, excuse me, the kinds of things he said about me at the depositions.

But I knew that we had a judge who wasn't going to allow him to do that. In fact, we filed what's called a motion in limine or a motion to exclude evidence for the first trial relating to anything about the lawyers and who they were and what their politics were, et cetera. And Judge Kaplan granted that order.

So Trump and his counsel knew that if they tried to go there, they were going to be in very serious trouble. And that's the right ruling. I mean, lawyers should not become part of the story. And it's very important as a lawyer to make sure you don't become part of the story. Here, I have to admit, Kara, I'm not that up to speed on the facts, but my sense of it is she's fundamentally right in the sense that whether she herself

is disqualified or not, and I don't pretend to know Georgia rules on this or even the facts that are relevant, that should have nothing to do with the underlying indictments. I assume she was saying it, frankly, because she was so pissed that, and I understand that, they were making it a trial, trying to convert it into a trial about her. And that's always their strategy here. Like when you're up against the Trump team, you have to be better than an angel because any flaw

they will seek to capitalize on immediately. In our case, at the second trial, so E. Jean testified at both trials that because of the death threats and rape threats that she got so often, and because she lives in an upstate rural part of New York, she slept every night with a shotgun that she inherited from her father by her bed.

The Trump team, it didn't really come up at the first trial, but at the second trial, Habba made a huge deal about the fact that she did not yet have a license for the shotgun that she had inherited. And just step back for a second and think about that. How many people who show up at Trump rallies do you think have their guns licensed? It's a good example of the way these people fight. They will, no matter how hypocritical it is, no matter how

you know, none of them would think it applies to them. They will use any teeny wrinkle, teeny crevasse in your argument to attack people personally. So when you look at all the different felony indictments he's facing, which one do you think is most potent? Well, so here's, there's a substantive and procedural dichotomy here. Substantively,

I think by far any lawyer would tell you the Florida case about the documents is open and shut. I just don't know what the defense could be. It's open and shut case. It's different than Biden. They were different kinds of documents. His behavior was different, et cetera. The problem that you have procedurally is you have a judge who appears to not be that intent on getting it to trial before the election, to say the least. So substantively very strong, procedurally pretty weak.

Um, the next case I would say is the Jack Smith case in DC, the January 6th case. There, it's a harder case to make from an evidentiary perspective just because it's much more complicated. Like what happened on January 6th is a complicated story. It's not as simple as you took this top secret document and refused to give it back. Um, there you have a judge, um,

More similar to Judge Kaplan, I think, who intends to get it to trial. So if I were Trump, I would be most worried about that case. About that case. And I'm sure his lawyers are. Yeah, absolutely. And not the New York one coming up? Well, the New York one is a serious case. It just doesn't, in terms of the issues, first of all, it's kind of been in the public view for a long time. It feels like old news. Right.

And it's certainly not as big a deal as the federal crimes that he's been indicted for, both in Florida and in D.C. So one of the things you've been doing pretty much your career is using the legal system to make change. Before the E. Jean Carroll trials, you were most well known for your momentous win in the Supreme Court case, U.S. v. Windsor, which struck down the Defense of Marriage Act, which helped lead

to marriage equality. It was an incredible moment of optimism. I remember it. We've seen a lot of pushback. Anti-LGBTQ plus hate crimes have been on the rise, and a record number of bills were introduced in state legislatures in 2023, according to the ACLU. In short, courts can also be used to reverse change. Talk about that trial looking backwards on it.

So, you know, it's a very kind of bittersweet feeling when you talk about, when I think back on Windsor and Obergefell that was handed down two years later. I think for the most part, marriage equality is pretty secure. And part of the reason for that is it's just practical. It's very hard for the Supreme Court to unmarry people

or to allow there to be a situation where in one generation there are married couples who are gay and in the next generation there aren't. I don't think, there may be one or two votes for that on the Supreme Court, but I don't think the majority of them could swallow that. However, as you pointed out, efforts to kind of chip away

at the fundamental equality and dignity of LGBTQ people are unbelievably active right now. The number one method or tool that's being used is for people to say, I have certain religious beliefs. My religious beliefs don't approve of homosexuality. And therefore, I have a right to discriminate against gay people because that's what God tells me.

Um, it's a, it's a strange argument in the sense that it was an argument that was made about racial discrimination during Jim Crow. And today, no one in their right mind would think that anyone in the United States could say, I cannot let a black person in my store because God tells me black people are inferior. That's obviously insane. But that's the argument that's being used today and used with great success. Um,

We are litigating a case about my law firm about the Florida's don't say gay law. The other part of it that's very disturbing to me is about the don't say gay law. And the thing about the don't say gay law is it was deliberately written, I think, in a vague way to scare, excuse my language, scare the shit

Out of gay parents, gay kids. Gay teachers, yeah. Gay teachers. Or teachers in general. And I think the guy in the Atlantic said it. The cruelty was the point here. It's just intentionally a cruel thing to do. That scares me because it's one thing for gay kids or gay parents or gay teachers in states like New York or Washington, D.C., etc. It's another thing in the Deep South.

And it's starting to look like we have two separate countries, one in which gay people can live pretty, I don't want to say normal, but lives in which they're treated completely the same as everyone else and states in which they can't. And that's a pretty disturbing, it's almost like Jim Crow for gay people. What is the recourse for that? So the ultimate recourse is a change in the

membership on the Supreme Court. That's not going to happen realistically anytime soon. So if the federal law doesn't work, people have to essentially use the power of the ballot box and elect people in those states who see things differently and who are willing to change state law

and the state constitution to give people back the rights that were taken away by the feds. It's not a pretty picture. I wish I had a better answer to that, but I don't. What I'm worried about, and it really is going to say something fundamentally about who we are as a country,

is whether almost everything else other than the formalistic ability to say you're married to someone does get shipped away in the South. Adoption. Adoption, access to... Healthcare. Healthcare, access, just simple access to stores and restaurants and things that people take for granted every day. Okay. So...

I talked to ABC's Washington correspondent Jonathan Karl recently, pointed out Trump abuses the legal system, filing countless lawsuits in state and federal courts. This waste of resources, you know,

of his critics in the courts. Talk about this trend, because it's something you thought about too, is depleting resources of the right when you were in Charlottesville. Is this a coherent strategy for people to do, is deplete resources and continue with persistent lawsuits? I mean, as a lawyer, good for you, but... On our side, I would say no. I mean, I would say that the cases that I've brought, for the most part, have been very strategic.

have been cases that I think will make a huge impact, and thankfully some of them have, but are not cases that overwhelm the other side just by their sheer volume. I don't think that's a great strategy for our side. For their side, given the fact that they have places where they can sue, like certain judges in Texas or places like that, where they know they're going to win, it's not a bad strategy because they can just bring these cases forward

in single-judge districts, and they know they're going to get pretty much whatever they want from that judge, and they just create enough of a groundswell that ultimately they get it to the Supreme Court. So doing that in that regard, and in that regard, someone who likes to sue, you're representing the Center for Countering Digital Hate, a nonprofit that monitors online hate tweets and disinformation, which is under legal threat by Elon Musk over an article that said the company did not act on 99% of the hateful tweets by Twitter blue accounts, exes sued,

and said CCHD is running a, quote, scare campaign to coerce advertisers. In fact, it claims that CCHD itself is actively working to prevent free expression by, quote, attempting to coerce the deplatforming of those who disagree with it. It's accused you of being funded by foreign governments and media all without proof. It's part of a larger attack on researchers and academics, I think, to silence them. I'd love for you to talk about this case. Yeah, so in certain ways, it's a perfect example of this, right? Elon Musk,

ever since he bought Twitter, probably even before that, has gone around saying that Twitter, he sees Twitter or whatever it's called now, acts as the ultimate public square. And he's a free speech absolutist

And that public square is very important, and it should, it's almost, he thinks of it as a public service, that people have this ability to communicate with each other on what's now called racks. Yes, it's a private company. But he doesn't think that applies to him, right? It doesn't apply to CCDH. Like, he has the right to do that, but CCDH...

that simply just took public information available on Twitter and said to people, this is what's happening. They don't have the right to speak publicly. I mean, it's almost the classic, originally he had threatened a defamation case. He gave that up because I think he realized how hypocritical that would sound.

They then threatened a Lanham Act case, which is kind of like a defamation case. They didn't do that either. And the case they brought, that was ridiculous. California has a law that says you can't bring, it's called the anti-slap law, the first one in the country, that you can't bring lawsuits to try to stifle speech. It's hard to imagine

that the people who wrote the original anti-slap law in California didn't have exactly this lawsuit in mind or this kind of lawsuit in mind. They didn't know that Twitter or whatever exists. But it's exactly what it is. He literally thinks his people who have blue checks on Twitter should be able to say whatever they want. But if a nonprofit trying to deal with the horrible problem we have in our society of hate and disinformation and social media criticize that, they should be sued in silence.

As you can hear from what I just said, I'm very confident our motion to dismiss is going to be granted. And where does that go? But he does that. So did Peter Thiel. So did a lot of these people. And Peter won. But that takes to the Ninth Circuit when we went on the motion to dismiss. We have a very good judge. It's actually Judge Breyer's brother, Charles Breyer, who's a very experienced judge. Again, I'm very, very, I'm willing to go out on a limb and say we're going to win that motion.

And then they'll take it to the Ninth Circuit, but the Ninth Circuit I don't think is going to have much to do with it either. And then there's some federal issues here, but it's mostly state law, so very hard to imagine the Supreme Court taking. So I'm hoping he'll give up and go away, but maybe he won't. Maybe he won't. He's got a lot of money, I understand. He does. And a lot more money than CCDH has, for sure. Yes, absolutely. And you thought this was important to take this case forward.

because of that, because of this is, it's a very similar bullying case in a lot of ways. Yeah, it is. There's way too much bullying going on in our society today in almost every respect. And that's what this case is about. And it's important that we have people like Imran Ahmed, the head of CCDH and the group who are willing to speak up. And so they need, in my view, they need to be protected. Well, good. When he comes after me for my book, I think I'm excited to call you. You got a deal. I'm excited to call you. I

I'm just waiting because, you know, that was a thought. Honestly, it's in my head. I'm like, it would be ridiculous, but why not just deplete my resources? You know what I mean? And Kara, if you don't mind me saying this, the idea that you would be scared of that, you're one of the bravest journalists around, that you, it shows where we are, right? No, I'm not that scared, but I'm also concerned. You know what I mean? I'm concerned, 100%.

Yeah, yeah, 100%. Well, I'll give you my speed dial and I promise you we will have your back. All right, okay. I want to talk about one that I think probably you and I both disagreed on that I think was the one thing that

I'd love to know what you think now, how you reflect on the situation around when you resigned as chairwoman of the Legal Defense Fund of Time's Up because of your ties to Governor Andrew Cuomo. How do you reflect on the situation now? It was after an investigation revealed that you were involved in efforts to discredit a woman who accused him of sexual harassment. How do you look back on that now at this moment? So I'm glad you asked the question. I've spent a lot of time, as you can imagine, thinking about it.

First of all, let me say, I think it's a terrible tragedy that there's nothing like Time's Up that exists anymore. And I see, E. Jean and I both see in the dozens of letters that we receive daily from women who've been assaulted, that Time's Up was absolutely necessary and important. And it's just a shame that it imploded the way it did. I think we were all living in a kind of a Robespierrean moment at the time.

And in that moment, it didn't do much good for me to dispute what was said. What I said to Andrew Cuomo was, you need to do an independent investigation immediately and you can't blame the victim. That's the advice I gave to Andrew Cuomo at the time. He didn't follow that advice. He wasn't my client, by the way. He just called me for my advice because Time's Up had worked with him in extending...

the statute of limitation for rape in New York, which was among the shortest in the country. But that's kind of what happened. I spent a lot of time thinking about why things imploded the way they did and how we could do it better. Because it's clear to me that we need something like that to protect the many, many, many women out there. I mean, I should figure out a way to let people know the kinds of letters we get. It's just sometimes I feel like it's a tsunami of

that we get every day from women who've experienced this stuff. And we need to think again about how to support them appropriately. Did you think of the Carol case as that redemption, you know, of the beginning of that? Well, I was already representing E. Jean when this all happened. But yeah, I mean, I certainly believe that the E. Jean case is in certain ways the archetypical case of a woman who was attacked many years ago

who I think she was absolutely right in 1996 to not do anything about it. Her friend, Carol Martin, who told her not to, I think gave her the right advice. No one in 1996 would have believed her. The DA wouldn't have done a damn thing about it at the time. How to get justice and how to get justice when the person who attacked you is arguably the greatest bully on the planet. Mm-hmm.

And for yourself, when you pick a case, I have two more quick questions. Does that inform you, both your mistakes and your victories of what you've done? For sure. At least I hope so. I try very hard to think about it. So how do you decide what to pick now? Look, I mean, in retrospect, when Andrew Cuomo called and said, what should I do about this? And I said to him,

You need to get an independent investigator immediately and you need to stop. You can't blame the victims. I shouldn't even have said that. I should have hung up the phone. But, you know, we all don't have crystal balls. And as lawyers, our job is to give people the best advice we can. And you can't, you know, I don't subject my clients to lie detector tests. I think over time, although again, Andrew wasn't even my client. I think with experience and with age,

we think hard about these issues when we take on cases and when we take on every single client in case we've taken on where you stand behind, but it does require you to think long and hard about them. So the CCDH case, I feel very strongly that they are doing the righteous thing. And so we stood up for them. Eugene, same thing. And I'd say that about any single client my firm takes on. So last question. Um,

Are you scared? You talked about me being scared. I'm not scared of him. I just know him, right? Like it would mean nothing to him to hurt me, right? But are you scared of Trump if he ends up winning? He seems to have an antipathy to strong women, although he does seem scared of Taylor Swift, if I read his latest truth on her correctly. Yeah.

But many who have challenged him do tell me they're scared, such as former Defense Secretary Mike Esper. He said, I'm terrified. Are you worried at all as a lawyer, as a person living in this country? I think I came out of my mother's womb as a fighter. And so while I do experience fear from time to time, I'm pretty good at repressing that. And so for myself, I would say that I'm not very afraid. But I can't tell you that I'm not afraid for people in my family,

for people at my law firm, et cetera. I'm obviously, I'm concerned about that. And what do you do about that? How do you do that mentally? Look, I try to make clear that they understand and that there's things to kind of give them advice that our security people tell us about how to conduct your lives. And you can't just stop living your life. Obviously, that would be crazy. But there are things you can do. You know, I have this conversation with Eugenia all the time.

There are things that you could do that might be less risky than others, if that makes any sense. But you aren't going to stop doing cases like this. I'd have to be 10 feet underground. Well. Not while I've got blood pounding through my veins. Oh, on that note, I believe you on that one. Anyway, Robbie, thank you so much. I really appreciate it. What a great interview. Thanks so much.

On with Kara Swisher is produced by Neyma Raza, Christian Castro-Rossell, Kateri Yochum, Megan Cunane, Megan Burney, and Michael McDowell. Special thanks to Mary Mathis, Kate Gallagher, and Andrea Lopez Cruzado. Our engineers are Fernando Arruda and Rick Kwan.

Our theme music is by Trackademics. If you're already following the show, you have Kaplan on speed dial. If not, we'll see you in court. Go wherever you listen to podcasts, search for On with Kara Swisher and hit follow. Thanks for listening to On with Kara Swisher from New York Magazine, the Vox Media Podcast Network, and us. You can subscribe to the magazine at nymag.com slash pod. We'll be back on Thursday with more.