During the GOP MAGA ex-president’s 2nd January 2024 jury trial, he looked adoringly upon his pretty but inexperienced real estate lawyer Alina Habba who acted according to his instructions, doing his bidding. But she was facing the not so pretty opposing counsel Roberta Kaplan, an extremely deft New York trial lawyer, who has been competently and successfully representing the 80-year-old E. Jean Carroll, a former Elle magazine advice columnist who first sued the MAGA ex-president in November 2019 over his public declarations describing her as a liar, someone he wouldn’t look twice at, as he vehemently denied that he had raped her in the mid-1990s in a Bergdorf Goodman department store dressing room in Manhattan.

This second time, E. Jean Carroll, represented by her accomplished counsel Roberta Kaplan, claimed that even after winning the first lawsuit for $5 million dollars in a jury trial against the ex-president, he continued to defame her for daring to hold him accountable for sexual assault, despite the judge having ruled that the ex-president had indeed sexually assaulted Ms. Carroll.

But the MAGA ex-president couldn’t stand the idea that a strong determined woman bested him during the May 2023 trial by jury. So he continued to deny the accusations, claiming he had no idea who she is and that Ms. Carroll was not his “type.” Once, during a CNN town hall broadcast, he called Ms. Carroll’s accounting of the sexual assault as “fake” and labeled her a “whack job.” He and his cult-like followers continued for months to maliciously hound her mostly through the press and via social media.

During the 2nd jury trial, Ms. Carroll’s lawyer Roberta Kaplan asked for another $10 million in compensatory damages and “substantially more.” In early September, Judge Lewis Kaplan ruled (no relation to Roberta Kaplan) that the ex-president’s comments against Ms. Carroll were defamatory.

And for a 2nd time, on January 26, 2026, New York jurists in less than 3 hours, decided in favor of E. Jean Carroll, costing the ex-president $83.3 million dollars. So enthralled is the ex-president with his attorney that he had already paid millions of dollars to her law firm. And this man with suspect judgment is the one whom the GOP party has decided to coalesce around to be its presidential nominee. He’s planning to appeal this ruling.

As per a January 2024 Newsweek article, “Alina Habba Scolded on ‘Evidence 101’ During Court Showdown” by Kate Plummer:

Excerpts:

“Alina Habba, the lawyer representing Donald Trump in his E. Jean Carroll damages trial, was scolded by the judge during a court session on Thursday.”

“Habba, who previously worked in real estate law before becoming part of Trump’s legal team, is representing the Republican in the second defamation trial brought against him by Carroll. In May 2023, the journalist was awarded $5 million in damages after a jury found Trump liable for sexually abusing and defaming the former Elle columnist. The former president has denied sexually assaulting Carroll.”

“Commentators have criticized Habba for her court performance since the trial started, accusing her of making mistakes.”

“One such apparent blunder occurred when she was hit by an objection after attempting to question Carroll about her income from her Substack blog.”

“Ms. Habba, this is Evidence 101,” Kaplan told Habba.

Carroll’s attorneys then had the next ten objections sustained as Habba tried to ask questions.

“Did you not hear me?” Kaplan asked Habba when she talked over one sustained objection.

Habba appeared to make a mistake when referring to documents that had not been put into evidence. Kaplan ordered a recess in proceedings so that she might “refresh” her memory on how to.

“No, we are not going to read out loud a document not yet in evidence,” he said. “We are going to take a break here and you’re going to refresh your memory about how you get a document into evidence.”

She also had a tense exchange with Kaplan when she asked for an adjournment of the trial so that Trump could attend his mother-in-law’s funeral. Kaplan had previously denied that request.

Writing in her Substack newsletter January 17, Joyce Vance, a former U.S. attorney in Alabama, said Habba opened Trump up to “heavy damages,” with her courtroom arguments.

“A more skillful lawyer than Alina Habba might have avoided reminding the jury any more than absolutely necessary that her client sexually assaulted the plaintiff,” she wrote. “But by putting Carroll on trial and suggesting she is the one at fault here—money hungry, attention hungry—she’s given this jury a path forward to impose heavy damages on her client.

A Newsweek analysis of Federal Election Commission records found that between February 2022 and June 2023, Habba’s firm was paid millions by Trump’s political donors to defend him in court. New Jersey law firm, Habba Madaio & Associates LLP, received $3,586,350 from Save America and Make America Great Again, political action committees that back Trump.

As per the January 27, 2024 New York Times report, “In Trump’s Bitter, Yearslong Brawl with Roberta Kaplan, He Keeps Losing” by Maria Cramer and Kate Christobek:

Excerpts:

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 a transcript 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.”

That early skirmish was part of a battle that began in 2019 when the lawsuit was filed; it culminated in a Manhattan courtroom on Friday, when a jury of seven men and two women decided that Mr. Trump should pay Ms. Carroll $83.3 million for defaming her.

Mr. Trump, 77, has a libertine past, a salesman’s flair and an extraordinary instinct for insult. Ms. Kaplan, 57, an openly gay lawyer who married her wife in Toronto in 2005, is methodical and disciplined.

But they are both shrewd, competitive power players in their respective realms, and unusually deft at using the press. They rely on their own outsize confidence to achieve their aims, making their showdowns occasionally charged — and tinged with drama.”

She has represented major corporations and won the groundbreaking 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 five-hour deposition at Mar-a-Lago, Mr. Trump 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, smiling slightly.”

“And I think their attorneys, too,” Mr. Trump responded. “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.”

“In the months that followed, Mr. Trump and Ms. Kaplan would hurl accusations at each other, mainly through court filings, public statements and media appearances. The trial, which began on Jan. 16 in Manhattan, was a chance to see them both in a crowded federal courtroom.”

“And it provided a preview of what this unusual year in politics and history will present to the American public. As a former president and current candidate in the 2024 election, Mr. Trump faces four criminal cases, many of them sprawling and unpredictable, which he is seizing as a stage for his attempted comeback.”

“Mr. Trump elevates (justices and prosecutors) as opponents and tries to make them caricatures to mobilize his most fervent supporters.”

“So far, Ms. Kaplan is the only lawyer to have secured not one, but two verdicts against Mr. Trump.”

“This win is because of Robbie Kaplan and her dazzling team,” Ms. Carroll said in a statement late on Friday.”

“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 sought to diminish Ms. Kaplan, shrugging her off as a shill of the Democratic Party. He called her a friend of Andrew Cuomo’s, an apparent jab at her role in advising him when he was accused of sexual harassment during his tenure as New York governor.”

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

“But during the trial, it appeared 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 a news conference during the trial. She never raised her voice in court but was quick to play clips of that news conference to the jury.”

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

“Seated a few feet away from Ms. Kaplan, he shifted in his chair when she 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, focused solely on the jury and ignored the former president.”

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