Inside Trump’s Costly Outburst: ‘Like an 8-Year-Old Having a Temper Tantrum’

Roberta Kaplan knows how to beat Donald Trump in court. She’s already done it twice.

The lead attorney representing E. Jean Carroll secured a major legal victory against Trump last week in a trial that resulted in an $83 million judgment against the former president for defaming the writer. It was the second time in less than a year that Kaplan beat Trump and his legal team after Carroll went public in 2019 with her account of being sexually assaulted by Trump in a Bergdorf Goodman dressing room in Manhattan in the 1990s.

“The single most important thing that convicted Donald Trump — both from his deposition and from the trial — is Donald Trump’s own behavior,” Kaplan told me.

Long before that, however, she had earned a reputation as one of the most skilled and consequential litigators of her generation. She brought the case that resulted in United States v. Windsor, the landmark Supreme Court ruling that established federal recognition of same-sex marriage in 2013. She was also a member of the team that successfully sued the organizers of the infamous 2017 rally of white supremacists in Charlottesville, Virginia.

I first met Kaplan — “Robbie” to those who know her — well over a decade ago, while working with her when I was a young lawyer. We have remained friendly since then, as our career paths have taken us in very different directions and, more to the point, as her stature in both the legal and political worlds has grown.

I spoke with her this week about her recent trial victories, her experience litigating against Trump, and how federal prosecutors — who are doing their best to put Trump on trial before November — can maximize their odds of success in court.

This interview has been edited for length and clarity.

This is not the first time that you have secured a literally historic court ruling, but how is this different?

All those cases were incredibly important, but they were all for the most part about single issues or focused on single issues. Edie Windsor was about the equal civil rights of LGBTQ+ people. Charlottesville was about trying to do something against the scourge of white supremacy in our country.

But E. Jean to me is so critically important on two really fundamental issues. One, and we’re seeing that in terms of the responses we’re getting from people: victims of sexual assault — especially women who experienced it many years ago, before anyone thought it even happened, or if it happened wasn’t a very big deal — are just elated and so appreciative of what E. Jean has been able to do and the bravery of being able to talk about an assault that happened so long ago against the former president.

[Trump’s lawyers] wanted to say the other day that it was “he said, she said.” It wasn’t “he said, she said.” It was “he said” versus “she said, she said, she said, she said.” So there has been an enormous outcry of appreciation from mostly women for what E. Jean has done.

The second thing is equally, if not arguably more important, because we can’t have equal rights for women if you don’t have a rule of law and the system of justice.

And what this case has become about — I’m not sure it was originally about that — but what it has become about so fundamentally is, Can the court system work in a world in which you have a former president like Trump, with a huge base of support, who basically thinks that the rule of law doesn’t apply to him? Can our system function? And can Donald Trump be forced — whether he likes it or not — to follow the rules?

Let’s go back to 2017, the start of the Trump administration. The political and legal worlds are in slight disarray, sort of coming to grips with this person and what influence he may have over the country. You leave your old law firm, which is where you and I met, to start your own firm, and you quickly became active on the Trump litigation front.

Can you talk about the work you did and how the Carroll case fits in?

One of the main reasons I started Kaplan, Hecker was because, sadly, I’m very good at predicting bad things. [Laughter] It’s not necessarily a good thing to live with, but I’m like the Cassandra of lawyers.

I saw in 2017 that the country was facing — and the system was facing — a really, really serious threat and danger. One of the things I wanted to do is just fight against that. We were looking for cases to bring against Trump, and the fraud case — where we have not been successful; we’re on appeal now — was the very first case we were looking at and we brought against Trump.

E. Jean didn’t come until two years later, in 2019. George Conway has told the story, but he tells it exactly correctly. She ran into him at a party, and he promised to connect her to me, and I think she was in our office the next day or the day after.

I want to put a criticism to you and get your response. Conservatives look at this legal landscape vis-à-vis Trump, and they claim that Democrats are engaged in what they call “lawfare.” On the criminal side, there’s this fact-free theory offered by Trump and his allies, claiming that all these prosecutors have conspired to get them.

You’re a private lawyer on the civil side, and Trump has faced plenty of civil litigation as well. What do you make of the suggestion that you and other liberal lawyers have simply been out to get Trump from the start — any way possible — and that somehow you’ve been unfair to him and just brought all of your resources to bear just to target this one man?

We’re not good enough to do that. [Laughter]

We’re not good enough lawyers to somehow find some issue that Trump didn’t do or was not responsible for or didn’t break the law, and somehow torture him by arguing that he broke the law. It’s kind of the opposite. The problem is that Trump, for most of his life, has broken the law all the time, in every way possible — more times than probably anyone you or I know.

And so the question was, now that he was putting himself in the public eye, and obviously as leader of the country, was he ever going to be accountable for it? I think that’s the issue. And some of it is stuff that happened long ago.

E. Jean is a perfect example. It happened in 1996. I mean, we didn’t make up E. Jean Carroll. It happened — one jury has held and another jury has certainly confirmed — in 1996.

Same thing with our fraud case. Our fraud case with him — which I’m confident we’re going to win on appeal; we’ll be back — but the fraud case was basically Trump fraudulently promoting a pyramid scheme called ACN, a multilevel marketing scheme to very poor working-class Americans, ripping them off, telling them he wasn’t doing it for the money, he just really liked the company. And getting paid millions of dollars for it. And that was all pre-president.

I guess the better question is, “How well is our system working even then if someone who was so willing to engage in not only horrible conduct like sexual assault but consumer fraud, basically was never held to it account for it?”

You mentioned how you connected with Ms. Carroll. What was the process like of getting to know her?

George was at [the law firm] Wachtell. We never had a case with each other. We certainly never met each other socially. And I don’t think when he gave E. Jean my name, we had even met yet. We’ve probably only seen each other in person two or three times total. I think it was the fraud case, and that’s where he got the idea.

There’s no secret conspiracy between me and George Conway despite what others may think.

That’s interesting. I assumed you guys were social acquaintances or professional —

No, not at all.

Trump’s been accused of various forms of sexual misconduct by many other women besides your client. He’s frequently denied those claims. Obviously, every case is different, both factually and even legally. But why do you think more women did not sue Trump for defamation?

One of the facts that made E. Jean’s case different than a lot of the other cases about women who Trump has assaulted is that it was purely coincidental — the assault.

They ran into each other, and she was coming out of Bergdorf Goodman, and he was coming in. She didn’t want anything from Donald Trump.

E. Jean at that time was at the pinnacle of her success. She was beloved by her readers. She would have dinner at Elaine’s with the top writers and journalists. She would not have been interested in Donald Trump and would not have wanted to go into business or do anything with Donald Trump from a business perspective.

That’s true for some other women too, but it certainly made our case — her case for defamation — much cleaner. There was no preexisting relationship. There was no continuing relationship. There was no reason to think that she wanted anything from him.

In fact, as she put it, the reason she went along with him in that store that night is because it was a Thursday night, which was the night she would go to the writer’s table at Elaine’s, and she thought it would be an incredibly funny story to tell people.

I think that made the defamation issue for her easier. And on the other side of the equation, I think Trump saw her as such a threat — because she had a book, and she’s such a good writer — that he defamed her over and over again. Because she had spoken up in the way she had, in a way that made [Trump’s] defamation not only more repeated and continuous but more vicious.

He sort of — I hate to put it this way — benefited from the fact that there was a wave of women who came forward in 2016. Because then he was doing blanket denials —

Exactly, exactly.

Which I imagine is much harder as defamation.

Exactly. E. Jean said in her deposition that she had an incident with Les Moonves once in an elevator in L.A. where he kind of pushed up against her, and she said he was like an octopus. She was asked in her deposition, in our case, “Why didn’t you sue Les Moonves?”

The answer was because a lot of women accused him, and he just did a blanket denial — a group denial of all of them. [Carroll said that] if Donald Trump had done that here, I wouldn’t have sued him.

She also said if Donald Trump had said that it happened, but he thought she consented, she wouldn’t have sued him. What was so offensive about it was the idea that she was just making it up to sell a book or two as part of a Democratic plot.

I want to talk a bit about the nuts and bolts of the case. You went through this process of crafting a case, which is not as simple as I think a lot of people think. You have to figure out what evidence to gather through civil discovery, and that’s a lengthy and time-consuming process that itself involves a lot of strategic and tactical decisions.

So you’ve filed this case. You now need to conduct discovery and build a case. What are you doing? And how are you thinking about that process of gathering what you need?

Most importantly, from our perspective, is the fact that we have these two outcry witnesses — one literally right after it happened, and one probably the next day — her two friends Carol Martin and Lisa Birnbach. E. Jean had told them about what had happened almost right afterwards.

It was crystal clear from day one that they were going to be the key witnesses in the case. Because when you think about it, if Donald Trump was right and the case was concocted as part of a scheme, what that means is that Lisa Birnbach and Carol Martin had to be part of the scheme, which is pretty unbelievable. So the very first thing that we did is make sure that their recollections were the same as E. Jean’s, which they were.

And then we just started building the story. We had E. Jean’s account.

Later on, as we got closer to trial, we realized we needed someone to be able to describe what Bergdorf Goodman was like in those years and why it was not even remotely implausible that you could be in the lingerie department on the sixth floor on a Thursday evening and have no one around. So we went looking for Bergdorf Goodman witnesses, and we had two that testified at the first trial — both former employees.

Here’s the problem with representing a writer — so I hope you never get involved in a lawsuit, Ankush — they have a lot of documents to produce. E. Jean writes a lot, she gets a lot of correspondence, especially as an advice columnist. We had to immediately collect all that and go through it.

The discovery phase is one part of the process. But then you and your colleagues have to construct a case for trial, which is a process of editing, sequencing, thinking about how to tell a story. Tell me about how you constructed the trial presentation after discovery.

I think the hardest piece to build in this case, and honestly, the hardest piece for E. Jean personally, was to get E. Jean in a place where she could say out loud that she’d been harmed psychologically — and otherwise, frankly — by the assault.

She grew up in Indiana outside of Fort Wayne. Her parents — I think she said their two rules were “always look on the bright side” and “always smile.” Their family never talked about bad things. They just didn’t talk about it.

E. Jean worked in the era of gonzo journalism — there were very few women who succeeded and wrote for tons of magazines. I think she saw herself as being the kind of woman who could just do anything — never complained, up for anything. So it was very, very hard.

It was very hard for her to use the word “rape.” It was very hard for her to acknowledge that she’d been hurt by it. And it was really during the case itself — like somewhere in her head — she knew that she’d been unable to date any man since what happened, but she had a really hard time acknowledging the link.

And just so people understand: The reason for the link is — and this is a classic response to trauma — she believed that she was at fault for when she ran into Trump at the store for kind of having this jocular, kind of flirty conversation together, which they were, for sure, until he pushed her into the dressing room. And she blamed herself and thought that was a stupid thing to do. And as a result, since the assault, she had been unable to flirt with a man who was eligible because that had gotten her into such trouble.

And believe me, she had plenty of opportunities. She’s still gorgeous. She’s always been. She’s a beauty queen, just unbelievably beautiful.

So we knew that we had to get her there, and that was the single hardest thing we did. We found this expert, Leslie Lebowitz, who was one of the people who really started — with a bunch of other people in Cambridge, Massachusetts — with the idea of trauma studies. Leslie had started by working with Vietnam War veterans but has since branched out. And in certain ways, the prep that Leslie did — the work that she did talking to E. Jean for her testimony — was in a way a kind of therapy for E. Jean, too. Because it helped her to understand these things.

The tactical decisions of Trump’s lawyers, even Trump himself, have come under scrutiny. I want to briefly go back to discovery, when you deposed Trump. That video became somewhat infamous because of some of the comments he made, and you introduced some of that at trial.

I once heard that when you all took a break for lunch — my understanding is that the deposition was at Trump’s lawyers’ offices — that Trump’s lawyers had arranged lunch for everyone, and Trump got angry about that and had what was described to me by someone else as a “meltdown.” Did that actually happen?

That is true, but two things I have to correct.

One, it was at Mar-a-Lago. And it was not the deposition for E. Jean. It was the deposition the week before in the fraud case.

At E. Jean’s deposition, someone had spoken to him, so they actually provided us a free lunch without any protests.

What happened the week before?

The week before, we were about 11:30 in the morning, and I said, “Sir, I have one more topic I want to cover, but is it okay after I cover that we break for lunch?”

He said something like, “Well, why should we break for lunch? Why can’t we go straight through? Let’s just get this over with.” And I said, “Well, look, I would do that, but there’s a court reporter, there’s a videographer that needs a break, so we’re going to break for lunch.”

And then you can kind of see his brain working. He says, “Well you’re here at Mar-a-Lago. What do you think you’re going to do for lunch?” And I said, “Well, I’ve spoken to your lawyers about that issue, and they graciously offered to provide us with lunch.”

At which point he took the pile of exhibits — which as you know, Ankush, was probably a good two feet high to that point — and just threw it across the table.

Really?

Yeah.

Then they did provide us with a lunch. It was late, but we did get lunch, and then when Trump came back, he said to me, “So how’d you like the lunch?” And I said, “Well, actually, I just had a banana, but thank you very much.”

That’s slightly amusing, as a lawyer, but antics like this occurred in the courtroom — Trump speaking out of turn, leaving the courtroom and so on.

Some of this was in front of the jury —

A lot of it.

Could you tell what they were thinking? Were they shaking their heads? Were they rolling their eyes?

This jury was very hard to read. I think they felt because of their anonymity — and probably because of the seriousness of the case — they must have felt that they shouldn’t look at us. They really looked down. There were some men in the front — seven men and two women — and literally, I don’t think they ever looked up. They were taking notes, and I never met eye contact with any of them.

Oh, wow.

Yeah. They were all very hard to read. It was very interesting.

At the end, after the verdict, as they were walking out and after Judge Kaplan gave them advice [to maintain their anonymity], two or three of them, including at least one of the men sitting in the front who we couldn’t read at all, smiled directly at E. Jean and nodded their heads. That was the first reaction we’d gotten.

But you’re absolutely right, and it really goes to his deposition, too. His misbehavior at the deposition in Carroll — the way that he insulted E. Jean, the way that he insulted me. The way he said to me that I wasn’t really his type, either, and talked about suing me — “very strongly” is what I think he said.

That, combined with how he acted in the trial — which was speaking under his breath, shaking his head, getting up, as everyone knows, about eight or nine minutes into my closing argument. That conduct ...

We’re good lawyers. I’m not saying that the people on our team weren’t good lawyers. And E. Jean was an amazing plaintiff. But the single most important thing that convicted Donald Trump — both from his deposition and from the trial — is Donald Trump’s own behavior.

That’s what it looks like to me, but you know, I don’t want to oversimplify it.

It wasn’t just being nasty to me in the deposition. He basically said about the Access Hollywood tape, “Unfortunately, or fortunately, stars have been able to get away with that for millions of years.”

He literally said that. Think about that. In a case in which he was accused of sexual assault!

It’s the same concept. It’s this concept that he’s just lived his life — and he can’t seem to get around it — based on the assumption that the rules that apply to everyone else don’t apply to him.

At trial, it was even more dramatic because essentially, it was a trial on damages only. Our whole thesis was, “This is someone who acts like a bully and who can’t and won’t follow the rules.” So one would think that when you’re in the courtroom with the jury — acting like a bully and not following the courtroom rules as instructed by the judge — that would be a bad strategy.

Judge Kaplan said to him at one point, “You obviously can’t control yourself.”

I would think — if I were on the jury and I saw this behavior, given the nature of the case — the damages number would be going up in my head in real-time.

Yeah. Oh, there’s no question.

When he left during [my closing] — I didn’t see it happen because I was facing the other way — but when Judge Kaplan announced that he’d left the courtroom, I thought to myself, “Okay, that’s another $10 million.”

Your cross-examination of Trump was very brief, but as you and I know, preparing to cross-examine someone is a very significant project, and what the public and the people at trial see is a tiny sliver of it. Can you talk to me about how you prepared to cross-examine Trump, even though it only ended up being a few minutes?

The hardest part about preparing for the cross of this case was that we didn’t know [what Trump could say]. We had asked Judge Kaplan, I think even before the trial started, in a letter, to help elucidate the topics that were actually relevant and admissible in the case and what would be the scope of what Trump could say if he were to testify.

Judge Kaplan, understandably, waited until the day [of Trump’s testimony] to have any discussion about what Trump was going to be allowed to say. So because we didn’t know, we had to prepare for various things that Trump might be able to say in the courtroom.

I think the hardest thing about cross-exam — I remember talking to the team and going to bed at night and thinking creatively about all these things that we could do with him. But it’s much harder sitting there, frankly, having the discipline to do almost nothing. [Laughing]

At the closing, I said to the jury, “You know, it was a very short cross, but I got a very key fact from that cross. He said he didn’t go to the first trial.” And I said, “What does that mean? And why is he here today? Because today, this trial is about money. And that’s the only thing this man cares about.”

I got rapt attention when I made that point.

You’ve now secured two major verdicts against Trump in less than a year. Federal prosecutors are pushing to put Trump on trial before November.

If that happens, what sorts of suggestions might you have for Jack Smith and his colleagues about how to approach their case and Trump’s defense in a trial?

This isn’t rocket science. You have this guy who is so incapable of behaving like an ordinary litigant and, in those cases, like an ordinary criminal defendant.

I’m sure that they didn’t need our trial to learn this, but to the extent that Donald Trump exhibits behaviors of contempt for the rules and contempt for the court and contempt for the judge, that’s a very good thing.

It was interesting in the closing. Shawn Crowley [a Kaplan co-counsel who handled part of the closing argument] and I had very different strategies that complemented each other a lot. I just tuned Trump out when he misbehaved. I’m very good about separating things in my brain, so I just kind of ignored it.

Shawn in her rebuttal — Shawn, who is quite tall and was wearing high heels, actually pointed at Trump.

I can’t believe she had the guts to do that. She pointed at Donald Trump several times during the rebuttal, like a prosecutor pointing at a criminal defendant.

That’s exactly what I was going to say. She was a prosecutor, right?

Yeah. And apparently, he just had his arms folded, and he was just grimacing at her. And the jury saw that too.

I’m curious about your assessment of the media coverage during the trial. I think there’s a concern in some quarters that the media has effectively adopted a horse-race coverage approach to the legal proceedings, and that that isn’t the best way to serve the public. We get all the stories about Trump storming out of this and that, but maybe the coverage is a little too minute-by-minute — a little too indulgent of Trump’s antics.

I’m not sure I agree with that, but I wanted to put that to you and see what you think.

I don’t know. I think, in certain ways, having the public understand that Trump was misbehaving throughout the trial, like an 8-year-old having a temper tantrum, was a very important thing for people to understand. I understand it’s not going to change the minds of his cult followers, but I think it can change the minds of people who may be in the middle.

One of the flaws — one of the huge mistakes that he made — is he really thought that showing up was going to make a difference. He thought that the jury was going to be like at a MAGA rally. And he could not have been more mistaken in that regard.