Trump Attorney Looks For Conviction To Be Overturned In E. Jean Carroll Case

 January 31, 2024

In a legal twist that seems to unravel more with each passing day, former President Donald Trump finds himself again in the throes of a contentious court battle.

An $83.3 million defamation lawsuit against Donald Trump has sparked controversy over the judge's alleged past mentorship of the plaintiff's lawyer.

Questions Raised Over Judge's Impartiality in Defamation Suit

The story broke when Trump's attorney, Alina Habba, raised concerns about Judge Lewis Kaplan's impartiality. Kaplan, who is presiding over the current case, allegedly once mentored Carroll's lawyer, Roberta Kaplan. This purported connection, unearthed through a New York Post story, dates back to when both Kaplans worked together at a New York City law firm in the 1990s.

Habba voiced her concerns about the potential conflict of interest stemming from the unreported mentor/mentee relationship. Moreover, she highlighted the ties between Judge Kaplan and another of Carroll's lead counsels, Shawn Crowley, who previously served as Kaplan's law clerk and whose wedding Kaplan co-officiated. Disclosing such connections is crucial in ensuring a fair trial, according to Habba.

The defense attorney referenced federal law and Canon 3 of the Code of Conduct for United States Judges, which mandates judges to recuse themselves from cases where their impartiality might reasonably be questioned. Habba's findings and subsequent claims are poised to form the basis of an appeal, suggesting that Judge Kaplan's conduct during the trial was biased against Trump's defense.

Clashes in Court and the Appeal Strategy

Throughout the jury trial against Trump, reported clashes between the defense and Judge Kaplan have only added to the tension within the courtroom. Alina Habba has signaled her intention to argue that Kaplan's alleged hostility towards Trump's defense and preferential treatment towards Roberta Kaplan should result in an appeal.

If Your Honor truly worked with Ms. Kaplan in any capacity — especially if there was a mentor/mentee relationship — that fact should have been disclosed before any case involving these parties was permitted to proceed forward.

Addressing the concern, a representative for Roberta Kaplan minimized the significance of the relationship with Judge Kaplan. It was clarified that the two had worked briefly in a large firm, with no direct working relationship, as Roberta Kaplan was a junior associate and Judge Kaplan was a senior partner then.

The Ongoing Disputes and Potential Remedies

The legal entanglements between Trump and Carroll have been complex and multifaceted, encompassing multiple lawsuits and appeals. A notable event in this ongoing saga was a jury awarding Carroll $5 million in a case where Trump was found to have sexually assaulted but not raped her. That case is currently under appeal.

Trump, who has consistently denied ever meeting Carroll, found himself on the other side of a lawsuit when he sued Carroll for defamation after she publicly claimed rape. This suit was halted by Judge Kaplan, who stated that the jury's decision demonstrated the claim of rape to be 'substantially true.'


The defamation lawsuit against Donald Trump has taken a contentious turn with the revelation of a possible undisclosed past mentoring relationship between the presiding judge and the plaintiff's lawyer. Trump's legal team, led by Alina Habba, has questioned the impartiality of Judge Kaplan and suggested the existence of a conflict of interest.

With multiple legal clashes and a substantial $83.3 million at stake, Habba plans to appeal based on these concerns, particularly highlighting the alleged hostility from the judge. The broader context includes a series of ongoing disputes between Trump and Carroll, with previous cases leading to significant awards and appeals. This case continues to unravel, demonstrating the ever-complex and often unpredictable nature of high-profile legal battles.

About Aileen Barro

With years of experience at the forefront of political commentary, Robert Cunningham brings a blend of sharp wit and deep insight to his analysis of American principles at the Capitalism Institute.

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