As the New York criminal investigation into the Trump Organization deepens, a parallel battle is quietly playing out in the city’s family court, where lawyers are trying to muzzle one of the government’s key witnesses—and cast doubt over her mental health.
Jennifer Weisselberg, the ex-wife of Trump employee Barry Weisselberg—and former daughter-in-law of one of Trump’s closest business confidants, Allen Weisselberg—has told investigators that executives at the Trump Organization were rewarded with untaxed perks.
Her documents and grand jury testimony were crucial to last month’s indictment of her former father-in-law, the corporation’s chief financial officer. And she has repeatedly explained to journalists how the tuition for her children’s private school was an untaxed corporate gift paid in lieu of salary.
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But all the while, she’s said these things at great personal risk; since March 19, Jennifer Weisselberg has been under a judge’s gag order to shut her up.
“Defendant, Jennifer Weisselberg, shall refrain from having any discussions or interviews whatsoever with the press about the parties’ children… the custody proceeding… or her motivation for giving interviews insofar as it concerns the children,” reads the order, signed by New York County Supreme Court Justice Lori S. Sattler.
But if she can’t talk to journalists about her children—or even her “motivation” for speaking to journalists—then she can’t explain to the public how the Trump Organization allegedly broke the law. And she’s the only person who witnessed these alleged crimes and is willing to speak publicly.
The gag order does not limit her from speaking to investigators. But three sources familiar with the divorce proceedings describe the gag order as part of a broader campaign of witness intimidation. Attorneys separately representing her ex-husband and children have repeatedly demanded court-mandated mental evaluations and drug tests for Jennifer Weisselberg. And these sources say these orders smear her character ahead of a potential criminal trial where she would be expected to testify against the company.
The Trump Organization and its CFO, Allen Weisselberg, were charged with criminal tax fraud, falsifying business records, and scheming to defraud the government. According to the June 30 indictment, the company paid its CFO off-the-books by, among other things, covering the cost of his grandkids’ tuition at the Columbia Grammar and Preparatory School. Jennifer Weisselberg claims to know the intimate details of that financial arrangement, but she’s legally barred from discussing it on the news.
The gag order was issued in her divorce case against Barry Weisselberg, the manager of the Trump Organization’s Wolman ice rink in Central Park. The case has been ongoing since 2017 but got nasty when it morphed into a custody battle that continues today.
Jennifer Weisselberg has been fighting the gag order in court without success. As her previous attorney, Aimee Richter, put it at a hearing in May: “What we have here is a concerted effort to keep my client quiet.”
“So it’s come full circle; lost her children, lost all her money, she is going to lose where she’s lived for the last year and… now, she’s losing her right to speak,” Richter said in court.
What appears to have set off this chain of events were emails from NBC News correspondent Tom Winter and then-CNN producer Sonia Moghe. In those emails, the reporters asked Barry Weisselberg’s lawyer about the ex-couple’s expensive corporate apartment—one of the company perks under investigation—and mentioned the ongoing custody case.
Those emails immediately made their way to Karen Rosenthal, a court-appointed attorney tasked with independently representing the children’s interests. Rosenthal wrote to the judge’s law clerk, asking the court to step in.
“I seek the court's intervention to prevent Ms. Weisselberg from discussing the custody proceedings or the children as it relates thereto,” she wrote in an email reviewed by The Daily Beast.
The very next day, the judge issued the gag order. The document indicates it was made with the “consent of the parties,” but subsequent court hearings show that Jennifer Weisselberg opposes the measure.
In past interviews with journalists, the mother of two has answered questions about the joint investigation by the New York attorney general and Manhattan district attorney. In the course of doing so, she also mentions how Trump personally signed checks that would pay for her children’s tuition, a point that was detailed in the indictment against the company.
But Rosenthal, the attorney independently representing the couple’s children, objects to press interviews that mention how the children attend Columbia Prep—and allegations that Trump paid for it. In court proceedings, Rosenthal has described Jennifer Weisselberg’s decision to speak publicly as a decision “to prioritize her 15 minutes of fame” over the privacy of her children, a move that is “embarrassing them on a daily basis.”
“That is supposed to be their safe place, to go to school and learn. No. Now, it’s about who paid the bill,” Rosenthal said at a hearing on May 26, in which she requested that the judge punish the mother by holding her in contempt of court.
Rosenthal and the ex-husband’s lawyer, Peter Stambleck, both requested that the judge seal off the courtroom from the public, barring journalists from reporting on what happens inside. The judge decided against that. But the issue came up again at a hearing the next month on June 7, when the judge herself said, “Obviously, the press is allowed to be here and they are here.” But she also noted, “I find the whole thing somewhat disturbing.”
Jennifer Weisselberg and her current attorney, Duncan Levin, declined to comment on this story. Barry Weisselberg and his attorney, Stambleck, did not respond to questions.
Reached by email on Saturday, Rosenthal, the attorney representing the children, stressed that “no one in the pending post judgment of divorce litigation is in any way trying to silence Ms. Weisselberg.”
“I will do anything and everything necessary and legal to protect my young clients from emotional harm,” she wrote.
But a legal advocate for Jennifer Weisselberg sees things differently.
Zoe Applbaum, who has been monitoring the case since February as a volunteer for the nonprofit STEPS to End Family Violence, said the gag order is part of an effort to harass and intimidate the mother of two.
“It’s a silencing tactic,” Applbaum said. “They’re bullying her and they’re being completely one-sided. They’re putting her in the hot seat so Barry doesn’t have to be.”
Applbaum also noted that Stambleck and Rosenthal, who separately represent the father and children, have “constant requests for drug tests and mental evaluations” that seek to smear the mother—and potentially put into question whatever testimony she could bring during a criminal trial of the Trump Organization and Allen Weisselberg.
“It’s an invalidation of her voice. If you order a bunch of evaluations, it’ll look like a person is mentally ill,” Applbaum said.
Three people familiar with the case who spoke to The Daily Beast on condition of anonymity expressed suspicions that Barry Weisselberg and the Trump Organization could be utilizing these lesser-known court proceedings to derail the government’s investigation by harming a witness with damning testimony.
Rob Georges, an attorney who represented Jennifer Weisselberg in her initial talks with the Manhattan DA, criticized the legal skirmish playing out in family court.
“It seemed like she was being treated unfairly. They’re trying to discredit her,” he said.
So far, however, this case has actually been helpful to investigators. As The Daily Beast reported, Barry Weisselberg’s previous testimony in the divorce confirmed that the Trump Organization covered the cost of several luxury apartments.
The judge, already frustrated at the public scrutiny of her courtroom, has tried to distance the case before her from what could turn out to be the most highly publicized criminal case currently making its way through the justice system.
“This is a custody case. This is a case about two children. This isn’t a case about Donald Trump or the Trump Organization,” the judge said in May.
