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…
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