Bloomberg Law
June 9, 2023, 8:00 AM

Attorney Roberta Kaplan on Leaving Big Law and Taking on Trump

Vivia Chen
Vivia Chen

Robbie Kaplan, who left her partnership at Paul Weiss in 2017 to start her own practice, is known for taking on high-profile cases with major social impact. In 2013, she argued before the US Supreme Court on behalf of Edith Windsor in the landmark United States v. Windsor case that granted federal recognition of same-sex marriages.

Last month, the founding partner of Kaplan Hecker & Fink won a $5 million civil suit against former President Donald Trump for her client, E. Jean Carroll, involving allegations from the 1990s. The jury found Trump liable for sexual abuse and defamation.

Here are excerpts of our recent conversation, which has been edited for brevity and clarity:

On Facing Donald Trump:

Did you expect to win?
Yes and no. In terms of evidence, it was overwhelmingly in our favor. We had all the witnesses—and he had none. (Editor’s note: Trump didn’t testify and his lawyers called no witnesses.)

Trump said it was a conspiracy. But that theory means all the witnesses had to be liars, and that’s a tough burden to meet. So I was comfortable we would win. But we faced a general societal bias about cases of assault. We also had the issue that it happened a long time ago.

It seemed like Trump was a dream defendant for you, particularly when he mistook Carroll for his ex-wife Marla Maples in an old photo?
He was a dream defendant because he has a habit of lying and getting caught. And a lot of that was captured on video. (Editor’s note: Trump’s video deposition was played for the jury).

As I pointed out in my closing, even when he was caught mistaking E. Jean for his second wife Marla, he said, “Oh, it was a blurry photo”—and that’s just not true.

Roberta Kaplan
Photo: Kaplan Hecker & Fink

He’s wily. He got elected president of the United States. He’s got street smarts. And he knows when to turn on the charm. ... People underestimate him. But he’s not a smart litigant.

What about the deposition?
It was a constant stream of insults directed at me. You’ve known me for a long time, and you know I’m no Zen Buddhist. But I was cool as a cucumber. Trump would go on his tirades, and I’d asked him calmly, “Are you finished now?”

On Women in Law:

It seems you’re part of a trend of big-name female lawyers dropping out of major firms. Does Big Law have a woman problem?
I think there’s been progress in Big Law. Women like [Paul Weiss partner] Karen Dunn are doing well.

I don’t know if it’s a gender issue or if the problem is that we keep sticking by an older model that no longer works. At a huge firm there are lots of conflict issues, and you have to bill by the hour. When I left Paul Weiss, I had a sense there was a fundamental change in the legal market, especially in litigation. I sensed that clients preferred boutiques that had flexibility in how cases would be litigated.

Is your firm different because it’s led by a woman?
That’s a tough question. I certainly hope so. We think about that consciously—from the way we staff cases to thinking about HR issues. We have a six-month parental leave policy, and that’s a big deal for a firm of our size. It matters to us that we are a majority women-owned firm and we think about those issues. I hope our associates agree.

Did you struggle with work/life balance in your career?
To be a great lawyer requires dedication to work at the drop of a hat. It comes with the territory. I don’t know how it can be otherwise.

I think the hardest thing for women litigators is coming up with a style that jurors can relate to. Given the fact I’ve won this most recent trial and the one in Charlottesville with Karen Dunn [a 2021 case against white supremacists in the Virginia city], I think it’s less of a factor. At this point, my style is my style. Whatever the gender ramifications, it’s working.

Do women have different expectations than when you came out of law school?
When I was clerking for Judge Judith Kaye [on the New York State Court of Appeals], I was doing the work of two or three people, and I felt it was unfair. In my conversation with Judge Kaye, she advised me, “You should let it go.” She said she would just go to the bathroom and splash cold water on her face and do her work. I told her that’s not my generation. And I think the younger female lawyers won’t put up with things we did.

Anything else you wanted to achieve in your career?
The one regret is that I never became a prosecutor. I thought I’d be joining the DOJ. In the Hillary Clinton administration.

To contact the reporter on this story: Vivia Chen in New York at

To contact the editor responsible for this story: Gregory Henderson at

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