The meeting turned ugly fast.

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

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

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

“You wouldn’t be a choice of mine either, to be honest with you,” he said, according to transcripts of the deposition. “I would not, under any circumstances, have any interest in you. I’m honest when I say it.”

She began another question, then paused and reminded him, “I’m an attorney.”

Ms. 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 deposition. He called her “a political operative,” “a disgrace.” When she asked him if he had been referring to Ms. Carroll when he said in June 2019 that people who make false accusations of rape should “pay dearly,” he said yes.

“And I think their attorneys, too,” Mr. Trump responded, smiling slightly. “I think the attorneys like you are a big part of it, because you know it’s a phony case.”

Ms. Kaplan did not respond.

It was a clash of two New Yorkers, both of them formidable combatants 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 won a 2013 Supreme Court case that granted same-sex married couples 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 are engaged.

In the months that followed the deposition at Mar-a-Lago, Mr. Trump and Ms. Kaplan would hurl accusations at each other through court filings, public statements and media appearances.

The trial, which began on 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 as the victor when a jury of seven men and two women decided that Mr. Trump should pay Ms. Carroll $83.3 million for defaming her.

“This win is because of Robbie Kaplan and her dazzling 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 like Robert S. Mueller III, the former F.B.I. director, and Jack Smith, the special counsel. But so far, Ms. Kaplan is the only lawyer to have secured 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 on 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 had sexually abused 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 representing Edith Windsor, the gay rights activist whose challenge of the Defense of Marriage Act was one of two landmark cases that led the Supreme Court to grant same-sex married couples federal recognition in 2013.

A prominent voice in the #MeToo movement, Ms. Kaplan has also defended clients against accusations of sexual abuse. In 2020, she represented Goldman Sachs Group when the company was sued over accusations that the bank’s general counsel had covered up sexual misconduct claims against its head of litigation.

Ms. Kaplan, a native of Cleveland and a graduate of Harvard and Columbia University’s law school, has said she always knew she would be a lawyer. That was in part because she was a born talker, sometimes to the exasperation of her family. In an interview on the podcast “Original Jurisdiction,” Ms. Kaplan recalled her grandmother once telling her when she was young: “Robbie, you know I love you, but can you just be quiet for like three minutes?”

“And I said something like, ‘No grandma, I can’t. I just can’t help myself. I love to talk,’” Ms. Kaplan recalled.

So does Mr. Trump, in his own way. A son of a Jamaica Estates developer, he burnished his image as a playboy in the 1980s, making himself a fixture at night spots and in the tabloids. As a businessman, he exaggerated his real estate achievements, taking his mogul’s image national thanks to reality television. As president and a candidate, he belittled political opponents and demonized the media, 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 deposition in 2022, Mr. Trump seemed unfazed by Ms. Kaplan, whom he shrugged off as a shill of the Democratic Party. He called her a friend of Andrew Cuomo, an apparent jab at her role in advising him when he was accused of sexual harassment, an entanglement that prompted her to resign from Time’s Up, an organization founded to fight sexual abuse and promote gender equality.

“I act appropriately with women,” Mr. Trump said confidently. “Let’s see how this all turns out.”

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

He delivered tirades at news conferences during the trial. She never raised her voice in court but was quick to play clips of those news conferences to the jury.

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

He shifted in his chair when Ms. Kaplan said the hate that 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 nerve to suggest that Ms. Carroll should be grateful for the attention. And when Ms. Kaplan said that Mr. Trump acted like the rules and laws didn’t apply to him, Mr. Trump stood up and walked out of the courtroom.

The display of temper caused courtroom onlookers to stare 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 her closing, crisply addressing the jury and ignoring the former president.

“No matter what Donald Trump thinks, and no matter what Donald Trump says, the rules do apply to him,” she said.

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

They nodded at some of the jurors, and some of them nodded back.

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