E. Jean Carroll Hints At How Donald Trump Could Have Won Their $90 Million Court Battle

E. Jean Carroll, the woman who has repeatedly prevailed in her legal battles against the president, suspects she could have lost if Donald Trump had taken the stand.

The journalist and advice columnist recently reflected on her court drama with the politician, noting that he would have had the advantage of winning over the jury members, who hailed from Republican-leaning cities and towns, if he had testified.

Fortunately for E. Jean Carroll, President Donald Trump chose to ignore his lawyer's advice and opted for golfing rather than defending himself in court. His decision was an expensive mistake he would never forget, as his accuser was awarded nearly $90 million in damages.

Carroll addressed her victory over Trump in her sexual abuse and defamation lawsuit during a recent appearance on Cat Greenleaf's "Soberness Story Hour" podcast. The live taping of the episode occurred at the Algonquin Hotel on Thursday.

The journalist told the host that Trump had good cards to ensure he won the case, from his fantastic defense attorney Joe Tacopina to the jury members hailing from Republican-leaning cities and towns. However, she believed the president lost because he chose not to testify.

"He could have won. But he didn't follow Joe Tacopina's advice. He didn't come home from Ireland," Carroll explained. PageSix reported that she was referencing Trump's decision to continue golfing on the Emerald Isle instead of testifying near the end of their first trial in 2019.

Carroll emphasized Trump's chances of winning the legal battle, claiming he was skilled at defending himself and making a compelling case, given his successes in the White House. "He could have won over at least one juror and gotten a hung jury," she added.

As for why Trump did not stop golfing in Ireland to testify in the sexual abuse and defamation lawsuit, Carroll believed he was scared of being cross-examined by her lawyer, Roberta Kaplan, because the legal rep "would have ripped his head off."

The drama between Carroll and Trump started in 2019 when she first went public with her sexual abuse claims. The journalist's winning streak began in 2023, when a federal jury in New York found the president liable for sexual abuse and defamation and awarded her $5 million.

Carroll's second victory came in January 2024, when a jury found Trump liable for defamation after he slammed the first verdict and labeled his accuser a liar. The Blast covered the story, reporting that Trump was livid after the jury awarded Carroll an additional $83.3 million in damages. 

The POTUS slammed the verdict as "Absolutely ridiculous!" in a heated social media rant, stressing that he disagreed with both verdicts that found him liable for sexual abuse and defamation. He declared he would appeal "this whole BidenDirected Witch Hunt."

"Our Legal System is out of control, and being used as a Political Weapon. They have taken away all First Amendment Rights. THIS IS NOT AMERICA!" Trump added.

Despite his arguments, former Assistant U.S. Attorney Andy McCarthy warned that he could end up paying more in damages if he continued to attack Carroll.

Following Carroll's second legal victory and the nearly $90 million in compensation, The Blast shared that her next move was to hurt Trump. The advice columnist announced her decision to donate the entirety of her compensation to causes the president hated.

Carroll claimed she would do so because she hoped her actions would "cause him pain." Additionally, she planned on setting up a fund for women who have been "sexually assaulted" by Trump and vowed to file another defamation case if his public attacks continued.

However, Trump refused to cough up a single penny without a fight and filed a $91.63 million bond in March 2024.

The Blast reported that he implored the court to recognize the bond and not force him to pay Carroll the awarded sum in damages until his appeal was heard at the US Court of Appeals for the Second Circuit.

Carroll's third victory against Trump occurred in September 2025 when three judges on the US Court of Appeals for the Second Circuit unanimously decided to uphold the jury's verdict. CBS covered the story, reporting that Trump's arguments were refuted.

The appeals court emphasized in its decision that Trump "made several disruptive comments and gestures in front of the judge and jury." The defamatory statements included him denying Carroll's sexual abuse claims and insisting she falsely accused him. 

As stated, the drama between Carroll and Trump began in 2019 when she went public with her sexual abuse allegations. She claimed the politician had forcefully inserted his fingers into her at a department store decades ago.

Will Donald Trump continue to appeal the nearly $90 million verdict or pay E. Jean Carroll?