The appellate judge whose dissent laid the groundwork for a Supreme Court intervention in E. Jean Carroll’s defamation case against President Donald Trump worked in the White House in 2019, when Trump made the defamatory comments. It’s an apparent conflict of interest that’s made even more relevant given the judge’s forceful defense of Trump’s actions at the time.

Judge Steven Menashi, who authored the dissent, didn’t recuse himself from the case — nor does it appear in the court record that he ever revealed his proximity to Trump at the time. But his actions could result in the case being thrown out or even put taxpayers on the hook for the $83 million granted to Carroll following a 2024 civil trial in which Trump was found liable for defamation for denying that he sexually assaulted her.

Carroll scored a temporary victory in her long-running fight against Trump on Wednesday, when a federal appeals court in New York said it would not reconsider one of two defamation cases against Trump. However, a lone Trump-appointed judge penned a dissent that could breathe new life into Trump’s side — without acknowledging his own time in the Trump White House.

Menashi was a special assistant and associate counsel to the president in June 2019, when the administration put out a statement saying that Carroll was merely “trying to sell a new book” and when Trump told a reporter on the White House lawn that “it’s a total false accusation and I don’t know anything about her.” Jurors in Manhattan considered those two statements when they concluded Trump acted with malice and awarded Carroll a massive sum.

The timing means that Menashi — who has been guarded about his interactions with Trump and whatever legal advice he gave the president — was working for the defendant in the case during the exact moment that led to the successful lawsuit.

Carroll’s lawyers did not respond to a request for comment. Calls to Menashi’s staff went unanswered.

On Wednesday, the Second Circuit Court of Appeals refused Trump’s request to have the entire bench reconsider a smaller panel’s decision last year to uphold the massive punitive damages against Trump. That smaller panel had accused the president of “extraordinary and unprecedented conduct” in his June 2019 statements against Carroll, supporting the view that he wasn’t shielded by presidential power when he did so.

However, the decision also came with Menashi’s vociferous 54-page dissent, which planted the seeds for the Supreme Court to weigh in.

In it, he criticized what he called “unauthorized damages, duplicative compensatory damages, and a grossly excessive monetary figure for a defamation claim.” He also highlighted what he called “several errors” in the case that made it “obvious that the president was acting within the scope of his office when responding to reporters at the White House.”

Menashi also disagreed that Trump should be held personally liable in the case. Menashi wrote that it “made no sense” for judges to block then-Attorney General Pam Bondi’s attempt to remove Trump and name the U.S. government as the defendant under provisions in the Westfall Act, which protects government employees from lawsuits while on the job — though the trial judge considered those arguments at length and even had appellate courts in New York and Washington, D.C. weigh in.

But most importantly, he gave Trump’s lawyers the key phrase they need to get the Supreme Court’s attention, writing that the appellate’s support of Carroll “created a circuit split.”

“The Supreme Court may want to consider whether that is how the Westfall Act applies to the president,” Menashi wrote.

The dissent was joined by Chief Judge Debra Ann Livingston, a 2007 appointee of President George W. Bush, and Judge Michael Park, another Trump appointee from his first administration.

Trump has long banked on a trip to the Supreme Court in this case, given that it now heavily tilts conservative and includes three of his own appointees. Menashi even argued that Trump could be shielded entirely by the Supreme Court’s unprecedented 2024 decision vastly expanding the scope of presidential immunity.

“Whatever one thinks about the merits of Trump v. United States, everyone agrees that it represents a significant legal development,” he wrote.

When Menashi was nominated to the bench in 2019, CNN surfaced editorials from his days as a columnist for the conservative New York Sun, in which he attacked feminists, gay rights groups and diversity efforts. He was lambasted by critics as “one of Trump’s most radical picks” and accused of authoring “Trump’s worst policies for immigrants and women.”

But Menashi refused to detail his work for the Trump administration, rebuffing questions from then-Sen. Dianne Feinstein about his interactions with White House aide Stephen Miller and declining to say whether he had anything to do with the administration’s policy that separated migrant families and children at the U.S.-Mexico border.

“I’m not authorized to talk about particular deliberative processes or meetings that occurred within the White House,” he said at his September 2019 confirmation hearing.

Court records in the Carroll case indicate that Trump testified he “did not consult with any other White House or administration official (apart from his wife and daughter) in making the June 2019 statements,” but it’s unclear whether he had any subsequent discussions about his legal exposure with White House lawyers. Trump’s full deposition in the Carroll case has not been made public.