Trump Lawyer Says Judge’s Alleged Conflict of Interest Could Affect Defamation Verdict

Former President Donald Trump's lawyer Alina Habba takes questions from the press during a break from court in New York on Oct. 17, 2023. Timothy A. Clary/AFP via Getty Images

Alina Habba, former President Donald Trump’s lawyer in his recently concluded defamation lawsuit, is questioning the presiding judge over a potential conflict of interest that could prove to be crucial to secure a new trial in the case.

The defamation trial ended on Jan. 26, with a panel of nine jurors ordering President Trump to pay the plaintiff, writer E. Jean Carroll, $83 million in damages. Ms. Carroll had sued the former president in 2019 over two of his statements in which he denied sexually assaulting her.

On Jan. 27, the New York Post ran a story alleging that Judge Lewis Kaplan, who presided over the defamation case, was once a mentor to the plaintiff’s lawyer, Roberta Kaplan (no relation), when the two worked together at the same law firm in the 1990s.

Ms. Habba then wrote to Judge Kaplan, asking for more clarity over the issue since a relationship between the judge and Ms. Kaplan could be a conflict of interest in the case.

“The underlying defamation case tried last year, and the damages trial completed last week, were both litigations in which there were many clashes between Your Honor and defense counsel,” Ms. Habba said in the Jan. 29 letter. “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.

“This issue is particularly concerning since Plaintiff’s other lead counsel, Shawn Crowley, served as Your Honor’s law clerk, and we were previously advised that Your Honor co-officiated her wedding.”

What the Law Says

Ms. Habba pointed to U.S. Code 28 Section 455 regarding the disqualification of a justice, judge, or magistrate judge. The code states that such officials should disqualify themselves in “any proceeding in which his impartiality might reasonably be questioned.”

One of the situations where the judge shall disqualify themselves is when a lawyer with whom the judge previously practiced law is the lawyer of an ongoing case.

“Here, without knowing more information (or having a specific factual denial by Your Honor that you had a mentor-mentee relationship with Ms. Kaplan), we are unable to flesh out our position concerning what specific relief should be requested, including, but not limited to, moving for new trials on the issues of liability and damages,” Ms. Habba wrote.

“Surely, however, this Court should provide defense counsel with all of the relevant facts. At a minimum, this information could certainly prove relevant to President Trump’s forthcoming Rule 59 motion.”

The Rule 59 motion is a request for a new trial.

In a statement to the New York Post, a spokesperson for Ms. Kaplan denied that the attorney’s relationship with Judge Kaplan was of any significance.

“They overlapped for less than two years in the early 1990s at a large law firm when he was a senior partner and she was a junior associate and she never worked for him,” the spokesperson said.

In her letter, Ms. Habba pointed out that the Trump legal team intends to appeal that the court was “overtly hostile” toward the former president and his defense counsel while exhibiting “preferential treatment” toward Ms. Carroll’s counsel.

“Indeed, the rulings, tone, and demeanor of the bench raised significant concerns even before the New York Post’s investigative journalism unearthed these new facts.”

A Heated Case

During the conclusion of the trial, Judge Kaplan and Ms. Habba engaged in a heated debate just before the plaintiff’s closing statement. The judge asked her to stop talking and eventually warned that she was “on the verge of spending some time in the lockup. Now sit down.”

The day before the trial’s conclusion, tensions erupted between the defense and Judge Kaplan. Ms. Habba wanted to call President Trump as a last witness. However, Judge Kaplan insisted that the former president promise he would not say certain things, like denying sexual assault allegations.

“Ms. Habba, I will decide what he has a right to do. That is my job, not yours,” the judge said.

When President Trump eventually was allowed to testify, it was kept brief. Judge Kaplan asked Ms. Habba to guarantee that her client would not incite people to harm Ms. Carroll.

When President Trump replied, “No, I just wanted to defend myself, my family…,” the judge struck from the record every word after “No.”

President Trump denounced the court ruling in a Jan. 27 post on Truth Social.

“Absolutely ridiculous! I fully disagree with both verdicts, and will be appealing this whole Biden Directed Witch Hunt focused on me and the Republican Party. 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!”

In May 2023, another jury ruled that President Trump was liable to pay $5 million to Ms. Carroll in a separate defamation incident that took place in October 2022. They also found him liable for “sexual battery.”