Roberta Kaplan was already a renowned litigator long before she represented E. Jean Carroll against Donald Trump. Now, she’s the only lawyer in history who has both successfully argued a monumental case before the Supreme Court and defeated Trump in court — twice. Earlier this month, a jury in New York ordered Trump to pay a whopping $83.3 million in damages to Carroll for defamation, and in the latest episode of On With Kara Swisher, Kaplan tells Kara that the former president has almost no chance of winning an appeal. Kara and Kaplan also discussed Trump’s legally perilous antics, his memory lapses about his wives, and the juvenile attempt he once made to call Kaplan a “cunt” in code. Two excerpts from their conversation are below.
Journalist Kara Swisher brings the news and newsmakers to you twice a week, on Mondays and Thursdays.
Kara Swisher: Let’s talk first about, obviously, the news, which is this verdict that you got: $83.3 million. It’s a big number. Talk about what it means. You had a couple weeks to reflect upon it; I’d love to know what you think now.
Roberta Kaplan: 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.
Swisher: Right.
Kaplan: And we now think that the reason for that was because it was only $5 million. But the $83.3 million 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.
Swisher: That things have a price.
Kaplan: Correct.
Swisher: So for people who don’t know, the jury awarded Carroll $7.3 million for pain and anguish, $11 million in reputational repair, and $65 million in punitive damages. 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 toward Carroll, right?
Kaplan: Yeah. So I thought it would be high. The reason I — 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. Jean, literally during the trial. I think my all-time favorite is he recorded a video — I think it’s a video — where he said, “I’m gonna keep on doing it.”
This is, again, during the trial, a thousand times. You can imagine I emphasized 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 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.
Swisher: Would you say he did that on purpose? Because obviously fundraising is part of his ploy with all these court cases. This isn’t a new, fresh thing. Was that a beneficial thing for him to do despite this verdict?
Kaplan: So it’s very hard for me to get inside his head. I think he thought it was gonna 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 gonna result in a verdict that high, he would have thought that was good for him.
Swisher: Right.
Kaplan: But again, I don’t try to get into his head.
Swisher: 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 “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 the — we’ll get to the cash in a minute — but walk us through what happens next.
Kaplan: 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 [Lewis] 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.
Swisher: And what happens to the cash? So if he does a bond, does it let — he has to pay less or he has to just guarantee it?
Kaplan: Yeah. If he does a bond, he has to pay less. He has to put up 20 percent.
Swisher: To the bond people?
Kaplan: To the bond people.
Swisher: Then they’re on the hook for the large amount.
Kaplan: And he has to give us some collateral, but they are on the hook. Um, 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 in — I’m embarrassed to say how long — 30-some years of litigating, I’ve never seen anyone do that. Most people would rather only put up 20 percent 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.
Swisher: And why is that? Why do you imagine? Do you have any idea?
Kaplan: Why did he have to do that? I suspect it’s because he couldn’t get a bond.
Swisher: Oh, interesting.
Kaplan: That whatever questions the bond companies were asking, either he didn’t wanna answer or they didn’t like his answers.
Swisher: 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?
Kaplan: 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 federal question of federal law for the Supreme Court. The chance there, again because it’s mostly state issues of defamation law, of sexual-assault law, et cetera, is even lower than the chance of winning at the Second Circuit. So almost negligible.
Swisher: 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.
Kaplan: If he is elected president, he will be president when the appeal is happening for sure. It’ll take about a year or two years. Under our system — I’m gonna 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, you know, tell the Second Circuit that he’s not gonna stand by. You know, he’s not gonna honor their decision or, I don’t know, just refuse.
Swisher: Then what happens?
Kaplan: 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 that, the legitimacy and the authority of those systems.
I don’t know. I mean, if we’re in that kind of a situation, arguably, we have a much worse problems on our hands because we’re almost in a situation of losing our democratic or republican form of government.
Swisher: He could just refuse. Could they arrest him?
Kaplan: Yes. But, again —
Swisher: He’s the president.
Kaplan: As president, who knows what he’ll do? Right.
Swisher: Right. Right. Wow. That’s — okay.
Kaplan: I mean, again, if we’re ever in that place, I think our problems are so much worse than E. Jean Carroll’s judgment.
Swisher: 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.
George Conway: 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 am not sure where I heard that, ’cause 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. Jean Carroll, 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 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, uh, I’d wanna 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 who’s a complete liar?
Swisher: Okay. Talk about that deposition and what George is asking.
Kaplan: Yeah. So the short answer to George’s question — and as people may or may not know, George is the person who told E. Jean 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 [how Carroll was] “not my type,” he told me that I wasn’t his type either. He told me that he was gonna sue me very strongly, whatever that means. He told me that I was a disgrace, et cetera, et cetera. I’m not really — I’m gonna be honest here — I’m not someone who’s known for their equanimity. I’m just not. That’s not how I’m wired.
Swisher: I can attest to that. Yeah. Go ahead.
Kaplan: 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 kinda go off. He does this a lot in all the different cases. He kind of goes on a tirade, like, he speechifies in 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.
Swisher: Right, that you didn’t react. That you didn’t — the non-reaction was a strategy, presumably.
Kaplan: 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. 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, 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 E. Jean is lying because she doesn’t remember. And I said, “So when — what’s your anniversary with your current wife?” And he said something like, “I’m not gonna dignify that with an answer.”
Swisher: Did that strike you, or was he being — because you could be just obstreperous or you could really have a neurological issue.
Kaplan: Well, it also could be that he just doesn’t care about his anniversary with Melania. Like, I’m not a hundred percent sure what it was, but it was very clear he didn’t know it, and he was using the I’m not gonna dignify it kind of as a defense to the fact that he didn’t know.
Swisher: Now one of the stories you told George was 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. And his lawyer 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 the put the story up for us.
Kaplan: The story, the insulting me at the deposition, is saying I’m not his type, or —
Swisher: No. The other one.
Kaplan: 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, etcetera.” So he kind of realized that as the time went on and was super-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, I said to him — oh, I didn’t know what to call him, so I decided to call him “sir” — So I said, “Okay, sir —”
Swisher: He likes that.
Kaplan: “Uh, 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 a waste of my time. Let’s just go straight through. I don’t wanna 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, and 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 gonna get lunch?”
And I said — I have to admit, I kinda 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
Swisher: Wow.
Kaplan: And then he started screaming at his lawyers. And I’m not gonna 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.
Swisher: Yeah.
Kaplan: 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 wanna 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. Um, and he looked up at me and said, “See you next Tuesday.”
For this, I am incredibly grateful for my utter ignorance.
Swisher: Yeah.
Kaplan: 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.” Which was when the Carroll deposition was. And then I didn’t know anything until we got in the car, and my colleague — who is 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 equanimity.
Swisher: I’m gonna say it. It’s C-U-N-T, which is cunt. He called you a “cunt,” essentially. Which is his way. That’s the perfect insult that he would think is really devastating to you.
Kaplan: Yeah, you could tell they’ve 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, uh, demeanor. I’m pretty 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.
Swisher: Right.
Kaplan: 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 sort of heard it.
Swisher: Right. And then you just let it lie. 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 court as a sort of campaign appearance and would spin it to his advantage. Do you think it did? Did you have a sense it could? Were you worried about that?
Kaplan: Well, the thing we were most worried about, Kara, 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, we’d — you know, you do it in a case like this many, many times. And I think this was the Thursday before, the 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 a really bad shape. And, you know, 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. [Leslie] Lebowitz. 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. So that was the No. 1 concern from our perspective. It wasn’t even about the strength or what it would do the trial. It was about what it would do to E. Jean.
In terms of the trial, I think, I’m 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 inure to our benefit.
We knew that there was very little that he could say. That’s the crazy part about it. I should — this really has come out — I should explain: Because of the earlier verdict and because of this principle known as issue preclusion or collateral estoppel, the fancy legal term, there was — he was not allowed to show up at the second trial and say to the jury, “I didn’t rape her.”
Swisher: “I didn’t do it.”
Kaplan: “I didn’t do it. I didn’t defame her.” He couldn’t do any of that. So you have to think about, from their perspective, any good lawyer, I’m sure you — I’m sure Alina [Hanna] said this too — any good lawyer would say, “Don’t show up. There’s nothing you could do to help yourself.” But he showed up anyway.
This interview has been edited for length and clarity.
On With Kara Swisher is produced by Nayeema Raza, Blakeney Schick, Cristian Castro Rossel, and Megan Burney with mixing by Fernando Arruda, engineering by Christopher Shurtleff, and theme music by Trackademics. New episodes will drop every Monday and Thursday. Follow the show on Apple Podcasts, Spotify, or wherever you get your podcasts.
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