Village Lawyer Takes on Trump


Village Attorney Roberta Kaplan is Making Trump’s Life Extremely Difficult


Over the last weeks, in a Federal courtroom at Foley Square, the first of multiple legal actions pending against Donald Trump has finally made it to trial. At the heart of the case is a tenacious woman, E. Jean Carroll (who has been willing to be bashed because she didn’t scream and didn’t immediately call the police when allegedly raped by a billionaire) but also a long-time resident of the Central Village, Roberta Kaplan. If you passed Kaplan on the street, walking with her son and wife, you would not think “powerhouse lawyer.” But you really wouldn’t want to get in her way.

On the other side of Donald Trump’s turbulent presidency, Kaplan has been a key player in making his life miserable. Leaving aside his indictment in Alvin Bragg’s corporate fraud, “hush money” indictment, the potential indictment in Georgia for trying to fix the 2020 Presidential election, the Federal January 6 insurrection investigation being conducted by Special Prosecutor Jack Smith, the Mar-a-Lago classified document grand jury and a civil probe by New York Attorney General Letitia James, what has taken the lead is a trio of lawsuits that allege rape, defamation, fraud and more fraud—all of which are helmed by one attorney. Kaplan’s clients include writer E. Jean Carroll, who filed an Adult Survivor’s Act and defamation case after Trump claimed she was “totally lying” about her allegation that he raped her a quarter-century ago in a Bergdorf Goodman dressing room, and  Mary L. Trump, Donald’s niece, who claims that Trump and two of his siblings deprived her of an inheritance worth millions (this case is presently on appeal).

“I became the go-to person to sue the president,” Kaplan told the Washington Post which reported that she said this with “considerable relish.” She is in many ways the ideal legal adversary to take on Trump. Kaplan is a brash and original strategist, with neither a gift for patience nor silence, a crusader for underdogs who has won numerous legal awards. In the Carroll case, Kaplan has survived efforts by Trump to dismiss the case, delay the case and to resist her ability to question him in a pre-trial deposition (only snippets of which we have seen so far).

Before the presidency, Trump was often as engaged in legal tussles as he was in real estate, suing and threatening to sue his way out of financial trouble. With a return to private life, he will no longer be protected by the office and will have to deal with these lawsuits.

For much of her career, there was little in Kaplan’s professional bio to suggest she would become an attorney suing behemoths. According to the Washington Post, Kaplan, known to all as Robbie, is a self-described “traditionalist, in pearls, pumps and pre-coronavirus, superior blond highlights, who long worked as a top commercial litigator at Paul, Weiss, one of the nation’s preeminent firms, where the fees tend to be if-you-have-to-ask-you-surely-can’t-afford-us.”

But she became increasingly identified as an advocate for liberal causes and innovative legal strategies. She is a lesbian, an observant Jew, and a die-hard Democrat for whom 12 hours constitutes a light workday. In her Washington Post interview, Kaplan spoke about how she got there. “My maternal grandmother always hated a bully… One really good job for going after bullies is to be a lawyer.”

Since launching her own firm six years ago, Kaplan has initiated a constellation of cases against powerful, often intimidating forces: white supremacists, major Hollywood players, the president of the United States. Legal writer Dahlia Lithwick calls her “an attorney general for the resistance.”


Stanford University law professor Pamela Karlan says of their frequent legal conversations: “Robbie’s not calling about feelings. She wants to fix it first. She’s the least diffident person I’ve ever met. Plenty of smart people worry about failing. They worry about every little thing. Robbie doesn’t worry about that. In a really disarming way, she doesn’t care if people view her as hyperaggressive.”

Kaplan remains most celebrated for the Edie Windsor case that, in 2013, successfully struck down the Defense of Marriage Act, paving the way with stunning alacrity for the legalization of same-sex marriage two years later to the day.

In 2017, Kaplan launched her own boutique (i.e., small) firm, still a rarity among female corporate lawyers, creating an unusual model that combines lucrative commercial litigation with a progressive public-interest practice. Free from the agendas of risk-averse institutional clients, Kaplan and her colleagues could take on any case they believed had merit.

Not long after her firm was formed, the horrific Charlottesville hate rally and murder erupted. Believing that Trump’s Justice Department seemed unlikely to seriously investigate and prosecute the people responsible for the violence during the “Unite the Right” rally and counterprotest—he infamously claimed there “were very fine people, on both sides”—Kaplan announced to friends and colleagues: “I want to sue Nazis.”

Within days, Kaplan and her team flew to Virginia. The firm adopted an outside-the-box approach and sued two dozen avowed neo-Nazis, white supremacists and associated groups, invoking the 1871 Ku Klux Klan Act to argue that they conspired for months to commit racially motivated violence, thereby making it more of a challenge for the organizers to adopt free speech as a defense. She won a $26 million verdict.

Suing the powerful has brought repeated threats.

When E. Jean Carroll first met with Kaplan, the lawyer quickly understood her client’s objective. “I don’t give two flying figs about an apology,” Carroll says. “I am dying to get him in a deposition. I want him to say that I’m not a liar. I just want him to admit that he lied and that, yes, it happened.” Kaplan is working hard to get him there.

“I’m ready. I’m excited,” says Kaplan. In the Carroll case, Kaplan believes that Trump’s proclivity for false and misleading statements—with more than 30,000 of them during his White House term, according to The New York Times—will be tested when he is under oath.

Kaplan is celebrated for her candor. She’s active in LGBTQ causes, recently serving as the board chair of the Gay Men’s Health Crisis. She has publicly cheered about her “big gay Jewish wedding” in 2005 to Rachel Lavine, who serves on New York’s Democratic Committee representing Greenwich Village and Soho. She has a 16-year-old son named Jacob and a goldendoodle. On Sunday mornings, she participates in a Talmud discussion group with her rabbi.

“What makes a good litigator and lawyer is being a pessimist and risk-averse because you need to be looking at problems around the next corner,” says Pamela Karlan, a professor at Stanford Law School who helped prepare Kaplan for the Supreme Court argument in United States v Windsor. “Robbie has been as successful as she is because she doesn’t appear to be that kind of thinker. She’s an optimist.”

Kaplan hasn’t made perfect choices, but right now she is a hero, and an enabler of justice.

Carroll views her lawsuit as symbolic. She told the Post, “It’s for all the women in the country who have been harassed or assaulted by powerful men, and feel helpless to do anything about it…I don’t have to be brave,” she says. “Because Robbie Kaplan is brave for me.”