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. It’s not true, but there you have it.

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........

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