Roberta Kaplan knows how to win in court—and beat Donald Trump

Long before Roberta Kaplan won not one but two verdicts against Donald Trump, it was evident she had the temperament to square off against a garrulous figure like the former president.

“When I was a little kid, I spent a lot of time with my mom’s mom,” Kaplan recalls. “And there’s this famous story in our family. When I was three years old, I think, I was with her, and she looked at me one day and said, ‘Robbie, can’t you just be quiet for a minute? Is it possible for you to be quiet just for one minute?’ And I looked up at her and I said, ‘Grandma, I’m sorry. I really can’t. I just can’t help myself. I really like to talk a lot.’”

Eventually, Kaplan discovered that she could be paid—quite handsomely, as it turned out—to talk for a living. In college, she briefly considered becoming a historian. But she wanted to live in New York City, and she was hesitant about dedicating her life to the study of Russian history. “There [are] not a lot of bright spots,” she says. “I thought it might be just too depressing to spend my life focused on Russian history, rather than beating bad guys in court.” She had also taken note of Sandra Day O’Connor’s appointment to the Supreme Court in 1981, when Kaplan was in high school. “I remember thinking that was a big deal,” she says, “and that there really would be opportunities for women in the law.”

Kaplan went on to embody that over the course of a 25-year career at the elite law firm Paul, Weiss, Rifkind, Wharton & Garrison, where she represented major corporate clients, such as JPMorgan Chase and Airbnb, and made a name for herself as a high-powered litigator. But she arguably became most famous for the groundbreaking civil rights case that she argued on behalf of Edie Windsor before the Supreme Court in 2013, which deemed the Defense of Marriage Act (DOMA) unconstitutional and paved the way for marriage equality just two years later. (Kaplan later chronicled that win in her book, Then Comes Marriage: United States V. Windsor and the Defeat of DOMA.)

Looking back on that case today—amid unrelenting political attacks on LGBTQ rights and on the queer community—is “bittersweet,” Kaplan says. “On the one hand, it was an enormous victory for the equal dignity of LGBTQ people in this country; without it, I don’t think we would’ve gotten marriage equality,” she adds. “On the other hand, today we have a very different Supreme Court, and we do not have even close to a majority of votes who I think would have voted for the Windsor case.”

After representing Windsor—and winning multiple cases in the state of Mississippi, striking down bans on same-sex marriage and adoption by LGBTQ couples—Kaplan was itching to pursue more cases that championed progressive causes. In 2017, once Trump was elected president, she decided it was the right moment to strike out on her own and start her firm, Kaplan Hecker & Fink. “I just wanted to have a smaller, nimbler firm where we could do more of what I wanted to do, including fighting Donald Trump,” she says. “I can’t believe I had the guts to do this. I just decided, ‘Okay, I guess if I don’t do it now, I’m never going to do it.’”

Kaplan also gleaned that Trump’s election would bring “unprecedented challenges” to democratic values, and she wanted to do her part. To help fund those public interest and pro bono cases, Kaplan has continued working with such Wall Street giants as Goldman Sachs—an arrangement that she says isn’t in conflict with her firm’s overall mission. “I treat every one of my clients exactly the same,” she says. “My job is to fully dedicate myself to my client’s interests and to always do what’s in my client’s best interest.” In fact, she says some of the companies she counts as clients (including Uber and Airbnb) are not only aligned with the progressive causes underpinning the firm’s public interest cases, but are also drawn to her track record of beating figures like Trump in court.

Since launching her firm, Kaplan has taken on—and won—cases against the white supremacists who marched on Charlottesville, Virginia, in 2017; and the state of Florida, in a lawsuit that curbed the reach of the “Don’t Say Gay” law enacted by Governor Ron DeSantis in 2022. More recently, Kaplan prevailed again when representing the Center for Countering Digital Hate in response to a lawsuit brought by Elon Musk; in March, a judge dismissed the case as Musk’s attempt to “unabashedly and vociferously” punish the nonprofit organization for exercising its right to free speech.

To hear Kaplan tell it, her success in the courtroom can be traced in part to her “outside the box” approach, in a field defined by constraints. “I had an art teacher in high school who told me I should never take another art class as long as I live,” she says. “But I am creative in one way, I think. I have a real ability to be able to think outside those strictures.”

Kaplan also prides herself on being persistent, like a “dog with a bone”—though she met her match in writer E. Jean Carroll. “I’m one of the most stubborn people you could ever meet,” she says, “but there’s one person I know who’s more stubborn than I am, and that’s E. Jean Carroll.”

That dogged resolve came in handy as Kaplan and Carroll faced off against the former president during two trials over the past year. Trump had not appeared in person at the first trial in early 2023, when he was found guilty of sexually abusing Carroll and ordered to pay $5 million in damages. But Kaplan had a sense of what to expect going into the subsequent defamation trial, which Trump attended almost in full. During a deposition for a prior case, Trump had said to Kaplan, “See you next Tuesday,” a phrase often used as a euphemism for a vulgar insult that can’t be printed here. (He was not, in fact, seeing her the next Tuesday.) “Thank God, I had no idea what it meant at the time—because I would’ve lost my temper,” she says.

When it came time for the deposition in the defamation case, she says, Trump would “go on and on”—and for the most part, Kaplan would let him. “At a certain point, I would say, ‘Are you done yet? Because I have another question,'” she recalls. “Which would drive him insane.”

Over the course of the deposition, Trump threatened to sue her; after doubling down on his claim that Carroll wasn’t his “type,” he added that he wouldn’t be interested in Kaplan, either. “If you are a woman litigator in my generation, you have to figure out a way to deal with things like that from the very beginning,” she says. “I’ve never been in a deposition like [that], for sure. But being in a deposition with a recalcitrant, stubborn, hostile witness who was insulting me? That was not even close to my first time.”

That kind of behavior continued into the trial, according to Kaplan and news reports of the proceedings. While the trial was underway, Trump had continued attacking Carroll online and on the campaign trail. Even in the courtroom, Trump was not bound by decorum, as he muttered insults and walked out in the middle of Kaplan’s closing argument.

When speaking about the trial, however, Kaplan is quick to return to Carroll, praising the fortitude she showed through years of endless legal proceedings—and during the trial, when she came face-to-face with Trump for the first time in nearly three decades. It was a moment that Kaplan had anticipated while preparing Carroll for her testimony; leading up to the trial, there had come a point when Carroll seemed to have a bit of a breakdown during trial prep. “She was almost having a hard time speaking, and we realized that it was because she was actually afraid to have to confront him,” Kaplan says. “So we worked with the same expert who we had used at the first trial, a psychological expert who deals in trauma.” When Carroll eventually took the stand at trial, Kaplan says, it was “the best testimony I’ve ever seen.”

That testimony didn’t just help Carroll secure a win. It also led to the jury ordering Trump to pay Carroll more than $83 million in damages—a huge sum that Kaplan says she didn’t anticipate. “I was shocked and thrilled by that number,” she says. “There’s only one reason for that number, and that reason is Donald Trump.” (Trump is currently appealing both verdicts; despite the outcome of the trials, he has continued to make public statements about Carroll and deny the sexual abuse, which Kaplan has previously said could open him up to another defamation lawsuit.)

Carroll’s case also helped draw attention to the Adult Survivors Act, which temporarily lifted the statute of limitations on sexual assault charges—the law that allowed her to sue Donald Trump over those allegations in the first place. Carroll, who had advocated for the law and helped get it passed, was one of the first to bring a lawsuit. By the end of 2023, over 3,700 lawsuits had been filed as a result of the law, including other high-profile cases against former governor Andrew Cuomo and rapper Sean “Diddy” Combs. (It’s not clear how many lawsuits had been filed prior to last May, when Carroll won the first trial, but an estimate from early 2023 put the figure at just under 70.)

Beyond the impact on survivors, Kaplan views Carroll’s case as a lesson in the importance of standing up to bullies. “Donald Trump may be the world’s number one bully, but he’s not the only bully,” she says. “I would argue that Elon Musk is also a bully. It’s important for people to stand up to bullies like that because the only way to beat a bully is to stand up. And we don’t want a society or a country that is ruled by bullies.” Still, despite the outcome and significance of her case, Carroll has maintained that survivors of assault have to decide for themselves whether speaking up and pursuing legal action is the best path for them—that it’s a “personal decision,” Kaplan says.

For Carroll, it was the right choice. Kaplan sees parallels between Carroll’s case and the fight that she took to the Supreme Court over a decade earlier—and not just because Kaplan’s wife says she’s good at “seeing the strength in old ladies.” Both Carroll and Windsor were clear-eyed about how their personal fights were in service of a greater cause. “One thing they both really had in common was this bravery, courage, and the determination to get justice, and not only for themselves,” Kaplan says. “They both had an inherent sense that their fight was everyone’s fight. And that’s why both those cases, I think, will end up in history as being so important.”