Lawyers who know Roberta Kaplan say they weren't surprised when she agreed to represent writer E. Jean Carroll in her litigation against former President Donald Trump, even though it meant being the subject of intense media scrutiny. Kaplan, her friends say, isn't the type of person to be intimidated.

"Robbie is absolutely fearless," says Pamela S. Karlan, co-director of the Supreme Court Litigation Clinic at Stanford Law School, who is a former co-counsel of Kaplan's and a longtime friend. "When she's taken on politically charged cases, she's done it because she felt it was the right thing to do. She will do what's right and isn't scared about the backlash."

Kaplan, 58, had had high-profile wins long before she agreed to represent Carroll. For 25 years, she was a litigator at Paul, Weiss, Rifkind, Wharton & Garrison, where she represented major corporations. In 2017, she left to create Kaplan Hecker & Fink, a boutique litigation firm.

In 2013, she achieved a U.S. Supreme Court victory in U.S. v. Windsor, in which the high court granted same-sex married couples federal recognition. The case is often considered a precursor to the court's 2015 ruling in Obergefell v. Hodges, which legalized gay marriage.

In 2018, she co-founded the Time's Up Legal Defense Fund, which provides support to victims of workplace sexual harassment and discrimination. Kaplan stepped down as chair of the board of directors of Time's Up in 2021 after an investigation revealed she had advised then-New York Gov. Andrew Cuomo in his efforts to fight harassment allegations.

In June, Kaplan made headlines again when she announced she was leaving Kaplan Hecker & Fink with partner Tim Martin to co-launch Kaplan Martin, a civil litigation, investigations and strategic advisory firm. Kaplan said the old firm had become too bureaucratic for her and that she'd been in conversations for months about starting a new firm that focused on civil as opposed to white-collar litigation, which had become the primary focus of her former partners. 
 

The New York Times, using multiple unnamed sources, described Kaplan as stepping down from her old firm after facing complaints that she had mistreated and insulted other lawyers.

Kaplan brushed off the criticisms. In a July interview with the ABA Journal, Kaplan said she hoped that in her lifetime, or her son's lifetime, "We will progress to a stage in our society in which people are no longer interested in 'women who yell' stories.

"I acknowledge that from time to time, when I am under stress, I yell, and I acknowledge that I have high standards," Kaplan said, adding that all her clients were moving with her to the new firm.

When asked to comment on the New York Times article, former law partners Julie Fink and Sean Hecker said they wished "our former partners well as they move forward and look forward to collaborating on work for our clients."

Opposing counsel describe Kaplan as a powerful foe.

"She can be a difficult adversary. She is also exceptionally bright, straight-talking, quickly grasps both sides of a case, is realistic about her client's position and open-minded towards creative resolutions," says Andrew T. Miltenberg, a partner in the New York City office of Nesenoff & Miltenberg. He says he's been in court against Kaplan in more than a dozen cases, including several pending matters.

Kaplan admits that underneath it all, she isn't always confident.

"Every time I have to wait for a jury verdict, I get despondent," she says. “It's the worst torture.”

During a five-hour deposition in 2022 at his Florida estate, Mar-a-Lago, Trump called Kaplan "a political operative" and "a disgrace," according to the New York Times.

But Joe Tacopina, who has represented Trump in a few matters, including one of Carroll's lawsuits, describes Kaplan as "the best lawyer" he's ever opposed. He says she has "a keen sense of strategy and is likable."

The Carroll suit "was a deeply contested case with high tension," Tacopina says. “I thought we would be at each other's throats, but while we fought hard, we treated each other with respect. I came out of it with a sense of admiration.”

Kaplan didn't originally have representing Carroll, a former magazine columnist, on her radar. After Carroll's memoir accusing Trump of sexual assault was released in 2019, Trump said he'd never met Carroll and that she wasn't telling the truth. Conservative lawyer George Conway, a vocal Trump critic once considered for two roles in his administration, was at a party with Carroll when he suggested she contact Kaplan to discuss her situation.

When Kaplan met Carroll, she found the columnist "smart, charismatic and charming," and agreed to represent her.

"I thought to myself, 'Let's bring this case,'" Kaplan says. As it turns out, Kaplan ended up representing Carroll in not one but two cases, both in the U.S. District Court for the Southern District of New York.

In May 2023, Trump was ordered by a Manhattan federal jury to pay Carroll $5 million for sexually abusing and then defaming her. The jury, however, did not find that Trump was liable for raping Carroll.

In the second case, Judge Lewis Kaplan found Trump had defamed Carroll repeatedly in 2019. The decision about damages went to a federal jury in Manhattan. In January 2024, the jury found Trump liable for $83.3 million to Carroll in punitive and compensatory damages. Kaplan expects to recover the damages. She declined to comment on her fee arrangement with Carroll.

The vitriol around the litigation was challenging.

"The atmosphere surrounding the jury trials was a whole different universe from anything else I have ever experienced," Kaplan says. "The crazy publicity, the press, the nuttiness–I just tried to separate myself from all of that. I didn't comment. I focused on the evidence and persuading the jury."

Carroll testified that she received hostile messages, including threats to rape and murder her.

"My primary concern was about E. Jean's safety," Kaplan says.

Kaplan, born and raised in the Cleveland suburbs, was talkative as a child.

"The story in my family … is that when I was about 3 years old, my grandmother got a little frustrated with me one day and said, 'Robbie, all you do is talk. Can't you stop talking for two minutes?'" Kaplan says. "I said something like, 'Grandma, I just can't stop.'"

Sometime later, Kaplan says, she realized lawyers are paid to talk. She thought maybe being a lawyer would be "the right job" for her.

Judaism also played a large role in her childhood, as it still does. She had a bat mitzvah and became more religious while attending Harvard College, where she studied Russian language, history and literature. During a year of studying in what was then the Soviet Union, she met with refuseniks, Jews trapped in the Soviet Union because they were barred from emigrating and freely practicing their religion.

In May, it was announced that Kaplan would represent Columbia University in its effort to defend itself in a Jewish student's lawsuit over the school's handling of protests on campus. The proposed class action alleged the school failed to provide "a safe in-person learning environment" during weeks of protests.

In July, a judge granted a joint motion to dismiss the Southern District of New York complaint. According to an earlier court filing, Columbia agreed to offer walking escorts across campus through its Public Safety Escort Program for students who request it because of protest activity. Also, the university will have the authority to authorize "alternative access and egress points" to and from campus, the filing states.

Kaplan says she represents Columbia in a number of lawsuits relating to the campus climate after Hamas' Oct. 7, 2023, surprise attack on Israel.

She also represented Columbia in several breach of contract claims brought by students who attended the school during the pandemic and wanted tuition refunds. In March 2022, a settlement was announced that provided thousands of Columbia students a fee refund for spring 2020 and provided the university with relief from further litigation with the settlement class.

Additionally, Kaplan represents universities in lawsuits related to Title IX, the landmark gender equity legislation of 1972.

Another client is Ashley Biden, President Joe Biden's daughter, whose diary was stolen in 2020. In 2022, two Florida residents pleaded guilty to conspiring to commit interstate transportation of the stolen diary, which they sold to the conservative investigative group Project Veritas before the 2020 election.
 

After graduating magna cum laude from Harvard, Kaplan attended Columbia Law School, graduating in 1991. She went on to clerk for U.S. District Judge Mark L. Wolf and New York Court of Appeals Chief Judge Judith S. Kaye.

In 1992, she joined Paul Weiss, making partner in 1999 at age 32. She had worked at Paul Weiss initially as a summer associate helping with a pro bono death penalty appeal in Texas. She describes herself as quickly "hooked" on the world of litigation by that experience. During her years at the firm, she helped companies such as American International Group Inc. and Morgan Stanley with their securities, bankruptcy and regulatory issues. She also was lead trial counsel for the California Public Utilities Commission in its claims against Pacific Gas & Electric Co. during the California energy crisis.

While chair of Paul Weiss' Women's Initiatives Committee, she helped change the firm's flextime, mentoring and day care policies.

Marty London, who retired from Paul Weiss in 2005 and is still of counsel, says Kaplan was, from the start, an outstanding lawyer and a person who brought with her “a little sunshine.”

Martin Flumenbaum, also of counsel at Paul Weiss, worked with Kaplan for many years. He particularly noticed how well she connected with her clients, and he describes her personality as a combination of charisma, energy and empathy.

"She has a way with people that gets them to trust her while she's being totally sincere," Flumenbaum says. "She has the ability to get anyone to open up, even adverse witnesses."

He also says her success as a litigator is in part due to how she prepares a case for trial.

"Our profession requires an enormous amount of attention to detail; it's not showing up in court," Flumenbaum says. “Robbie's not afraid to get her hands dirty in terms of details and documents. She does the preparation that is 95% of succeeding in a case.”

Kaplan is married to a woman. They have been together for 25 years and have one son. In 2009, she agreed to represent Edith Windsor, a lesbian widow. In 2007, Windsor married her longtime partner, Thea Spyer, in Canada, where same-sex marriage was legal, and their home state of New York recognized the marriage. But Section 3 of the Defense of Marriage Act prevented the U.S. government from doing so. When Spyer died in 2009, Windsor owed $363,000 in estate taxes she would not have had to pay had they been a man and a woman who were married.

The case, U.S. v. Windsor, made its way to the Supreme Court in 2013.

Kaplan called on Karlan, a seasoned Supreme Court litigator who has been mentioned as a possible Supreme Court nominee, for help in preparing the case to go the high court. They didn't know each other at that point.

"One of the things that is important for a lawyer is to know when you don't know something," Karlan says. "Robbie was an incredibly experienced litigator but had not done any work at the Supreme Court. I was impressed that someone as capable as Robbie was perfectly secure reaching out to other people in areas where they had more experience than she did."

Karlan ended up joining the legal team as co-counsel.

At one point, Karlan says, she and Kaplan were discussing oral arguments.

"She said to me, 'Do you think I can do it?' and I knew if I said no, she would want me to do it," Karlan says. "I said, 'Of course you can do it.' When you think about it, there aren't a lot of people who would give up arguing a case before the Supreme Court, but she was perfectly prepared to do that if people thought she couldn't do the best job."

Kaplan argued the case before the Supreme Court and won.

In a 5-4 decision, the high court ruled that the Defense of Marriage Act's Section 3 violated "basic due process and equal protection principles applicable to the federal government," Justice Anthony Kennedy, the swing vote for several cases in that decade, wrote for the court's majority.

The court didn't make a broad ruling in Windsor for same-sex marriage, but the decision meant that any federal law referring to marriage or a spouse also had to apply to legally married same-sex couples. It meant that married same-sex couples could file joint federal tax returns and receive other federal benefits and protections.

The case has been credited with paving the way for the high court's ruling two years later in Obergefell v. Hodges, in which the majority struck down state bans on same-sex marriage.

Kaplan left BigLaw in 2017 but remained in New York City to build a boutique litigation firm.

Kaplan says she left Paul Weiss because she "had a sense that the world was changing with respect to commercial litigation." She felt that companies were increasingly turning to boutique firms to handle "a diversity of litigation."

Another reason Kaplan started her own firm: She wanted the freedom to handle pro bono litigation as it popped up to fight the new Trump administration.

"I had a sense there would be a need to defend the rule of law during a Trump presidency," Kaplan says.

Indeed, as Kaplan was setting up her law firm, white nationalists converged on the University of Virginia in Charlottesville to protest the removal of a statue of Confederate Gen. Robert E. Lee. The rally lasted two days and included protesters carrying torches and chanting "Jews will not replace us," according to the Associated Press.

Kaplan co-represented students, local residents and clergy suing individuals involved in the rally.

Dahlia Lithwick, author and senior editor for Slate magazine, was living in Charlottesville at the time. She'd become friendly with Kaplan years earlier, but got closer to her when Kaplan wanted to help ensure there were legal consequences for the people involved in the rally's violence.

"Robbie really believes … that the law can get us to a fairer and more just world," Lithwick says. "And she really hates bullies."

Kaplan's team delved into hundreds of text messages and leaked communications from the social media platform Discord in the lead-up to the rally.

"I wanted people to see how dangerous white supremacy is and how widespread it had already become," Kaplan says. “I wanted people to see there were consequences.”

The jurors deliberated for three days in November 2021 before finding that the defendants had engaged in a conspiracy to commit harm under state law. The jury also found that some of the defendants had engaged in race-based harassment or violence. But the jurors could not agree on whether there was a racially motivated conspiracy to commit violence under federal law.

The jury reached a $26 million verdict against the defendants, including $12 million in punitive damages against the man who drove a car into a crowd of counterprotesters, killing one.

In December 2022, a federal judge ordered the damages reduced to $2.35 million due to a state law limitation on punitive damages. In July, the Richmond, Virginia-based 4th U.S. Circuit Court of Appeals restored more than $2 million of the damages.

Trump was seven months into his presidency when the rally occurred. Speaking about it at an August 2017 press briefing, he said that there was blame on both sides, and he had "no doubt about it."

No fan of Trump, Kaplan describes her concerns for what she describes as his part in dismantling the public's trust in the rule of law and the court system. In general, she worries that belief in the institutions that hold society together—such as the courts and the legal system—have been fraying in recent years. Unapologetically patriotic, Kaplan says that every lawyer needs to be a little brave when it comes to protecting democracy.

"I don't care what your politics are, we should all be able to agree as lawyers that there is such a thing as the rule of law and that the importance of it in our democracy can't be overstated," Kaplan says. “Every one of us should be making the case every single day that the rule of law is important. Every one of us should be fighting to retain it.”