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.