A federal judge in Manhattan told Melania Trump's legal team on Wednesday that pursuing sanctions against journalist Michael Wolff may not be worth the fight, even after the same judge dismissed Wolff's preemptive lawsuit and accused him of courtroom "gamesmanship."
U.S. District Judge Mary Kay Vyskocil, a Donald Trump appointee on the Southern District of New York bench, made clear she could not block the First Lady's lawyers from filing their motion. But she did not hide her skepticism about whether the effort made sense.
The exchange marks the latest chapter in a legal dispute rooted in Wolff's claims about the Trump family and convicted sex offender Jeffrey Epstein, claims the First Lady has forcefully denied and that her lawyers have called frivolous and made in bad faith. The case also raises a pointed question: when a journalist files a lawsuit that a court calls tactical gamesmanship, should there be consequences beyond dismissal?
Vyskocil did not hold back during the hearing, as Courthouse News Service reported. She told the lawyers in her courtroom that the standard for sanctions "places a very high burden on the moving party", meaning Melania Trump would need to produce "clear evidence" that Wolff acted in bad faith.
"I wonder if it's in the interest of the parties to continue litigating in this court."
The judge followed that with a broader observation about litigation culture.
"I think sometimes people get so caught up in the fervor of the moment that they don't really stop and think about the cost-benefit analysis of motions that are contemplated and the burden you put a court to."
She also noted plainly that "the case is now closed." But she acknowledged she "cannot stop a party from filing a motion that it believes in good faith is warranted, except in very rare circumstances that aren't present in this case."
In other words: you can file it, but don't expect an easy win.
Wolff, who has written four books about President Donald Trump since he first took office, filed an anti-SLAPP lawsuit against Melania Trump in 2025. New York's anti-SLAPP statute is designed to block legal action intended to chill free speech. Wolff invoked it after receiving a letter from the First Lady's lawyers threatening a billion-dollar defamation claim.
The journalist had publicly commented that Melania Trump was friends with Jeffrey Epstein and was playing an active role in the administration's handling of the Epstein files. In his lawsuit, Wolff stated that Melania Trump "plays no small part" in "the Epstein story." He also claimed Donald Trump "first slept with Melania Trump on Epstein's private jet."
Wolff did note in his filing that he "never said Melania Trump was involved in any of Epstein's crimes." He also accused the Trump family of creating "a climate of fear in the nation so that people cannot freely or confidently exercise their First Amendment rights."
The First Lady pushed back hard. In a recorded statement released in April, she said: "the lies linking me with the disgraceful Jeffrey Epstein need to end today." The Trump family has faced no shortage of personal legal battles in recent years, and this one clearly struck a nerve.
In May, Judge Vyskocil issued an order dismissing Wolff's anti-SLAPP lawsuit outright. She found that Wolff lacked standing to file the claim because Melania Trump had not actually sued him for defamation. The First Lady's lawyers had threatened a lawsuit, but no complaint had been filed.
The judge went further. She accused Wolff of engaging in an "inappropriate level of tactical gamesmanship" in bringing the preemptive suit. That language landed hard. It suggested the court viewed Wolff's filing not as a genuine defense of press freedom but as a strategic maneuver, one designed to put the First Lady on the defensive before she had even taken legal action.
Wolff is now appealing that dismissal. The status of his appeal, including which appellate court is handling it and whether a briefing schedule has been set, remains unclear from available court records discussed in the hearing.
Meanwhile, the Trump family has endured a string of hostile actions that extend well beyond courtroom disputes, and the First Lady's legal team appears determined not to let Wolff walk away without consequence.
In June, Melania Trump's lawyers wrote to the court stating their intent to seek sanctions against both Wolff and his counsel. The letter laid out the core argument in blunt terms: "Plaintiff's misconduct, and that of his counsel, warrants sanctions."
The lawyers added that "the sanctions should be sufficient to deter repetition and to compensate Mrs. Trump for the costs imposed by their misconduct." They cited what they described as Wolff's "factual misrepresentations, frivolous legal arguments and bad-faith conduct."
The team told the court it plans to file the formal sanctions motion by July 20.
What specific misrepresentations the motion will detail beyond the general characterizations in the June letter has not been disclosed. Nor is it clear whether Wolff has filed any response to the sanctions threat. Those gaps will likely narrow once the motion lands.
Judge Vyskocil's caution from the bench was not a ruling. She did not deny Melania Trump the right to file. But she made the difficulty of the path ahead unmistakable. Sanctions motions in federal court, whether brought under Rule 11, 28 U.S.C. § 1927, or the court's inherent authority, require more than showing the other side lost. They require proof that the losing party acted in bad faith, filed frivolous claims, or made material misrepresentations to the court.
The judge's statement that the standard demands "clear evidence" suggests she will not rubber-stamp the request. Melania Trump's lawyers will need to do more than point to the dismissal itself. They will need to show that Wolff's lawsuit was not just wrong but dishonest.
That is a high bar. But the judge's own dismissal order, in which she used the phrase "inappropriate level of tactical gamesmanship", may give the First Lady's team something to work with. A court that already found gamesmanship might be more receptive to an argument about bad faith than one starting from scratch.
The Epstein connection has been a persistent source of controversy for the Trump family. Wolff's claims about the First Lady's alleged friendship with Epstein and his assertion that the Trumps' relationship began on Epstein's private jet are the kind of allegations designed to generate maximum attention. Melania Trump has flatly denied any link to Epstein's crimes, and no court has found otherwise.
What makes this case unusual is the procedural posture. Wolff sued first, invoking a statute meant to protect defendants from retaliatory litigation. The court found he had no standing to do so because the threatened defamation suit never materialized. Now the defendant, Melania Trump, is the one pressing forward, seeking to punish the plaintiff for bringing a case the court called tactical.
The security and legal threats surrounding the Trump family have only intensified in recent years. Against that backdrop, the First Lady's decision to pursue sanctions reads less like a grudge and more like an effort to establish a precedent: that journalists cannot weaponize anti-SLAPP statutes as preemptive shields for unsubstantiated claims.
Whether the court agrees is another matter. Judge Vyskocil gave Melania Trump a clear win on the merits when she dismissed Wolff's suit. She may be less inclined to extend that win into the penalty phase, particularly with an appeal pending.
The Trump family draws relentless scrutiny, from the press, from political opponents, from litigants looking for leverage. Melania Trump's willingness to fight back in court, even when a judge signals the road is steep, reflects a posture the family has adopted broadly: don't absorb the hit, contest it.
The sanctions motion is due by July 20. Once filed, it will force the court to evaluate not just whether Wolff lost, he did, but whether his lawsuit was so baseless that punishment is warranted. Wolff's appeal of the dismissal adds another layer of complexity, since the underlying legal questions about standing and the anti-SLAPP statute remain live in a higher court.
Judge Vyskocil's warning was clear enough. She told the lawyers in her courtroom to weigh costs and benefits before pressing ahead. Whether Melania Trump's team heeds that advice or bets that the judge's own gamesmanship finding gives them the ammunition they need will become apparent in the coming weeks.
A court that already called the lawsuit tactical gamesmanship shouldn't be shocked when the other side asks for a penalty flag.