The lawyer who beat Trump twice stands to make a fortune for doing so

By Lukas I. Alpert

Roberta Kaplan left a career at the pinnacle of corporate law to pursue cases she deemed to have social importance

Roberta Kaplan was once a star litigator commanding high hourly fees at one of the top corporate law firms in the country, representing big companies and other clients with deep pockets. But in 2017 Kaplan decided to strike out on her own so she could have more freedom to take on cases she believed had social importance.

On the surface, it looked as if Kaplan, a prominent proponent of progressive causes, was trading in a lucrative career for something more like public-interest law.

Six years later, Kaplan has scored a stunning double victory against Donald Trump, representing writer E. Jean Carroll, who had accused the former president of raping her in a department-store dressing room in the mid-1990s. Trump has long denied the allegations, saying Carroll was "not my type."

In May 2023, a Manhattan jury found Trump liable for sexual abuse and for defamation stemming from comments he made in 2022, awarding Carroll $5 million. In January, a federal jury ordered Trump to pay another $83.3 million in damages for defaming Carroll, partly through remarks he made following the first verdict last year. When Carroll emerged victorious from the federal court in lower Manhattan last month, Kaplan swung her arm around the former magazine columnist and smiled in front of a swarm of photographers.

The combined $88.3 million in legal awards threaten to put Trump in a financial bind as he heads into the 2024 presidential election poised to be the Republican nominee for a third straight time. At the same time, the victories could be a huge financial windfall for Kaplan, showing that cases she deems to be of social importance might be even more lucrative than working for a huge corporate law firm.

As Carroll's attorney, the 58-year-old Kaplan took the cases against Trump on a contingency basis, meaning she wasn't paid hourly fees like most corporate lawyers and instead will pocket a cut of the winnings. In New York state, lawyers can collect as much as one-third of a jury award plus expenses in a case based on contingency, although many legal experts say the agreed percentage is often lower on awards that are so high.

At one-third of the total in this instance, Kaplan's contingency fee would be $29.4 million.

Through a spokesperson, Kaplan, who goes by "Robbie," declined to discuss the financial terms of her representation, noting that the cases and the value of the awards are subject to appeal. Trump, who called Kaplan a "political operative" and "a disgrace" when she deposed him, has filed an appeal in the first case and has vowed to appeal the second.

Carroll placed the credit for the victories solely at Kaplan's feet.

"This win is because of Robbie Kaplan and her dazzling team," Carroll said in a statement following the $83.3 million verdict.

From Wall Street to social advocacy

For 148 years, Paul, Weiss, Rifkind, Wharton & Garrison has been a legal force in corporate America. Based in the canyons of midtown Manhattan, it has nearly 1,000 lawyers working for big clients, such as private-equity firms Apollo Global Management (APO), Carlyle Group (CG) and KKR (KKR). The law firm generates $1.8 billion in revenue each year, according to the National Law Journal, as its lawyers relentlessly grind out hourly fees. Its profits per partner stand at $5.725 million, according to the American Lawyer.

The firm, often referred to as Paul Weiss, is also known for leaning left and being active politically. One of its most prominent partners is Robert Schumer, whose brother, Chuck Schumer, is the Senate majority leader and the senior Democratic senator from New York. Some former Paul Weiss lawyers now hold positions in the Biden administration.

Kaplan joined the firm in 1992 and made partner in 1999, working long hours on litigation matters for clients including JPMorgan Chase (JPM), T-Mobile (TMUS) and Airbnb (ABNB). Paul Weiss backed Kaplan as she pursued public-interest work and scored major, culture-changing victories. She committed significant energy to advocacy cases while at the firm.

In 2013 the firm supported Kaplan's representation of Edith Windsor in a landmark civil-rights case in which the Supreme Court struck down a key provision of the 1996 Defense of Marriage Act that had barred same-sex couples from enjoying marriage benefits under federal law. In the years that followed, while still at Paul Weiss, Kaplan litigated several LGBTQ-rights cases around the country.

But by 2016 she wanted to spend more time focused on such cases than her corporate work at Paul Weiss would allow, people familiar with the matter said. The firm, while supportive of her mission, preferred that she keep more of her focus on the lucrative corporate-litigation matters at which she excelled, those people said.

The time felt right for Kaplan to go out on her own, they said.

"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," Kaplan was quoted as having told Bloomberg Law last year.

Kaplan declined to comment, and a spokesperson for Paul Weiss didn't respond to MarketWatch messages seeking comment.

'We will collect the judgment'

When Kaplan launched her firm in 2017, then called Kaplan & Co. and now known as Kaplan Hecker & Fink, she said she envisioned a business that merged a private commercial legal practice with a public-interest practice.

"Unfortunately, there's no shortage of social-justice issues to litigate," Kaplan told the New York Law Journal at the time.

Today, according to a firm spokesperson, about a third of its workload involves what it considers to be advocacy cases, such as Carroll's. Other such cases include pro bono representation of nine victims of white-supremacist violence at the "Unite the Right" rally in Charlottesville, Va., in 2017, for whom Kaplan helped secure a $26 million award. She also has represented an unnamed victim of convicted sex offender Jeffrey Epstein, as well as President Joe Biden's daughter, Ashley, in a case involving the theft of her diaries.

She represented Trump's niece, Mary Trump, in a suit alleging he had defrauded her out of tens of millions of dollars in an inheritance. In addition, Kaplan briefly represented actress Amber Heard in a defamation case brought by her ex-husband, actor Johnny Depp.

The rest of the firm's work consists of more traditional corporate litigation, where a small firm would typically make most of its money. Among its clients on that side of the business include the Metropolitan Transit Authority, which it defended against a lawsuit brought by the state of New Jersey against New York City over a plan to institute a congestion-pricing fee for drivers coming into parts of Manhattan.

Kaplan has also represented spirits maker Diageo North America (UK:DGE) (DEO).

Switching back and forth between social-rights advocate and corporate litigator has had its pitfalls. In 2021, Kaplan stepped down as chairwoman of Time's Up, a nonprofit that supports victims of sexual harassment, after it emerged that she had provided advisory services to an effort to discredit an accuser of former New York Gov. Andrew Cuomo.

Since its founding, Kaplan's firm has grown from three to 63 lawyers, its spokesperson said. Several of them came from Paul Weiss, and the firm also counts some well-known legal figures, such as constitutional-law expert Lawrence Tribe, as being "of counsel," a category that denotes an affiliation with a law firm.

One partner, Joshua Matz, served as counsel to Democrats in the House of Representatives in drawing up articles of impeachment against Trump in both of the impeachment cases against the then-president.

The Carroll cases potentially represent the biggest financial wins Kaplan has scored since hanging up her own shingle - a remarkable victory for a boutique firm that has made social-justice cases the core of its business.

Regardless of how Trump's appeals play out, the Carroll cases have already taken a bite out of Trump financially. Trump has incurred $76 million in legal costs over the past two years stemming from the wide array of criminal and civil prosecutions he faces. More than $27 million raised in the last six months of 2023 to support his presidential campaign has instead been used to cover legal costs, according to campaign-finance filings.

Trump has been required to post the full $5 million award as a bond in order to appeal the first Carroll decision. He would also need to secure a bond for the full $83.3 million to pursue an appeal in the second Carroll case.

"We're pretty confident we'll get the money," Kaplan told "Good Morning America" after scoring the second $83.3 million award. "We might not get it right away. But, one way or the other, he owns a lot of real estate. It can be sold. We will collect the judgment."

-Lukas I. Alpert

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04-18-24 1517ET

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