Roberta Kaplan, a legal force, was Carroll's lawyer and Trump's arch-enemy

The encounter quickly turned ugly.

In October 2022, Roberta Kaplan flew to Donald Trump's Mar-a-Lago estate in Florida to question him under oath in the defamation lawsuit filed against him by her client, writer E. Jean Carroll, after she accused him of it. sexually abuse her.

“She's not my type,” Trump said when asked whether he raped Ms. Carroll in a dressing room at Bergdorf Goodman department store in New York in the mid-1990s.

Then he shrugged, looked at Mrs. Kaplan, and pointed at her.

“You wouldn't be my choice either, to be honest,” he said, according to transcripts of the deposition. “I would never have any interest in you under any circumstances. I am honest when I say it.”

She started another question, paused, and reminded him, “I'm a lawyer.”

Mrs. Kaplan, an openly gay lawyer who married her wife Rachel Lavine in Toronto in 2005, faced more invective from Mr. Trump during the five-hour statement. He called her 'a political agent', 'a disgrace'. When she asked him if he meant Ms. Carroll when he said in June 2019 that people who make false rape allegations “had to pay a high price,” he said yes.

“And I think their lawyers too,” Mr. Trump replied, smiling slightly. “I think lawyers like you are a big part of it because you know it's a fake case.”

Mrs. Kaplan did not respond.

It was a clash between two New Yorkers, both formidable fighters and talkers, but in different ways. While Mr. Trump, 77, has a salesman's flair for bombast and an instinct for insult, Ms. Kaplan, 57, is methodical and disciplined. An experienced litigator, she has represented major corporations and in 2013 won a Supreme Court case in which married same-sex couples received federal recognition for the first time. She has said that, as a lawyer, “I really am like a dog with a bone'- never letting go once her teeth lock together.

In the For months following the Mar-a-Lago statement, Mr. Trump and Ms. Kaplan hurled accusations at each other through lawsuits, public statements and media appearances.

The trial, which began Jan. 16 in a federal courtroom in lower Manhattan, was the first chance to see them in the same room.

And on Friday, it was Ms. Kaplan who emerged victorious when a jury of seven men and two women decided that Mr. Trump should pay Ms. Carroll $83.3 million for defaming her.

“This victory is thanks to Robbie Kaplan and her brilliant team,” Ms. Carroll said in a statement late on Friday.

Since Mr. Trump was elected president in 2016, he has faced investigations led by prominent lawyers such as Robert S. Mueller III, the former FBI director, and Jack Smith, the special counsel. But so far, Ms. Kaplan is the only lawyer to secure not one, but two verdicts against Mr. Trump.

“There is a way to stand up to someone like Donald Trump, who cares more about wealth, fame and power than respecting the law,” Ms. Kaplan said in a statement Friday after the jury's verdict against the former president . “Standing up to a bully takes courage and bravery; it takes someone like E. Jean Carroll.”

Last May, another jury awarded Ms. Carroll more than $5 million, finding that Mr. Trump sexually assaulted her and then defamed her by calling her a liar.

Ms. Kaplan was a partner at Paul, Weiss, Rifkind, Wharton & Garrison before founding her own law firm in 2017. Over the years, her clients have included the Minnesota Vikings football team, JP Morgan Chase & Company, T-Mobile and other corporate giants. Until she represented Ms. Carroll, she was best known for her representation of Edith Windsor, the gay rights activist whose challenge to the Defense of Marriage Act was one of two key cases that led the Supreme Court to grant federal recognition to married same-sex couples in 2013 . .

Ms. Kaplan is a prominent voice in the #MeToo movement and has also defended clients against allegations of sexual abuse. In 2020, she represented Goldman Sachs Group when the company was sued over allegations that the bank's legal counsel covered up sexual misconduct claims against the chief executive.

Mrs. Kaplan, born in Cleveland and graduated from Harvard and Columbia University Law School, has said she always knew she would become a lawyer. This was partly because she was a born talker, sometimes to the chagrin of her family. In an interview on the podcast “Original jurisdictionMs. Kaplan recalls her grandmother once telling her when she was young, “Robbie, you know I love you, but can you just be quiet for three minutes?”

“And I said something like, 'No grandma, I can't do that. I just can't help it. I like to talk,'” Ms. Kaplan recalled.

That includes Mr. Trump, in his own way. The son of a Jamaica Estates developer, he burnished his playboy image in the 1980s, becoming a fixture in nightlife venues and in the tabloids. As a businessman, he exaggerated his real estate achievements, who made his mogul's image national thanks to reality television. As president and candidate, he belittled political opponents and demonized the media, much to the delight of his followers. And when Ms. Carroll accused him of rape in 2019, he called her a liar trying to sell a book.

At the end of the 2022 statement, Mr. Trump seemed unfazed by Ms. Kaplan, whom he shrugged off as a Democratic Party shilling. He called her a friend of Andrew Cuomo, an apparent joke about her role in advising him when he was accused of sexual harassment, an entanglement that led her to resign from Time's Up, an organization created to combat sexual abuse combat and promote gender equality.

“I behave appropriately toward women,” Trump said confidently. “Let's see how this all turns out.”

But during the trial, it was clear that Ms. Kaplan had approached Mr. Trump. He shook his head repeatedly in the courtroom and scoffed during her direct examination of Ms. Carroll. She watched calmly as the judge threatened to throw Mr. Trump out of the courtroom after one of her co-counsel, Shawn Crowley, complained that the former president made derisive comments about Ms. Carroll within earshot of the jury.

During the trial, he delivered tirades at press conferences. She never raised her voice in court, but quickly played clips of those press conferences for the jury.

On Friday, during her closing arguments, he finally had enough.

He shifted in his seat as Ms. Kaplan said that the hatred Ms. Carroll received was the inevitable result of Mr. Trump's lies. He scoffed when Ms. Kaplan said that Mr. Trump’s lawyers had the audacity to suggest that Ms. Carroll should be grateful for the attention. And when Ms. Kaplan said that Mr. Trump was acting as if the rules and laws did not apply to him, Mr. Trump stood up and walked out of the courtroom.

The display of temper left courtroom spectators staring in disbelief at the former president's breach of decorum. The judge noted for the record that Mr. Trump had left.

But Ms. Kaplan continued with her closing, sharply addressing the jury and ignoring the former president.

“Whatever Donald Trump thinks and whatever Donald Trump says, the rules apply to him,” she said.

Less than seven hours later, after the verdict was read, Ms. Carroll took Ms. Kaplan's hands and the two women hugged each other tightly.

They nodded to some of the judges, and some nodded back.

Mr. Trump was not there. He had already left before the jury returned with its verdict.