It was just before Jennifer and Barry Weisselberg took their vows, in 2004, that Donald and Melania Trump gave them a one-bedroom apartment in Trump Parc East, at 100 Central Park South, across the street from Wollman Rink. It was their wedding present. Or so Jennifer thought at the time; she says she even sent the Trumps a thank-you note for what she perceived to be their incredibly generous gift.

It was only later, on August 7, 2018, in a deposition that was part of her divorce, that Jennifer learned otherwise. That was when Barry testified that the apartment, for which the couple only paid approximately $400 per month in utilities during the eight years they lived there, was owned by the Trump Organization. When asked by Jennifer’s lawyer what the rent for the apartment would have been had it “been rented to a third party,” Barry replied, “I have no idea.” And when asked if the value of that apartment was reported on his tax returns, he answered, “I don’t recall.”

According to a New York City accountant, the “gift” of the apartment is actually “in-kind compensation” and, as such, should have been reported as taxable income on the recipient’s taxes. “I don’t think it’s a gray area,” he says. “You’re working for a company and they’re paying your rent [in effect.] … It’s disguised compensation.”

“It Was Too Enmeshed”

Jennifer’s initiation into Trump World began in 1995 when Barry Weisselberg, then 20 years old and a recent graduate of Nassau Community College, walked into her office at an event-entertainment company in Hicksville, Long Island, to audition for a job as a Bar Mitzvah motivator, someone who could get party guests dancing. At that time, Jennifer had already appeared as a principal dancer on Club MTV, worked with Puff Daddy on the “It’s All About the Benjamins” video, and performed with the Joffrey Ballet, and when she saw Barry’s moves, she was taken aback.

“He wasn’t exactly Patrick Swayze,” she recalls. “We were laughing our asses off. I said, ‘I’m going to give him a chance.’ I regret that. Turns out it’s the only job he ever got on his own.”

At the time, Jennifer resembled a young Pamela Anderson, and soon Barry was bringing her to meet his family. In retrospect, she says, “it was just about his parents thinking that he was successful. ‘I have a girl,’” but at the time she found it charming. “Men like that build you up. They are over the top. They wrap you up in a situation.”

With Barry looking on, Jennifer signs the ketubah at their wedding.

Back then, Barry was living in his parents’ ranch house, in Wantagh, Long Island—in their wood-paneled basement that he had decorated with Pearl Jam posters and a Ping-Pong table—and Jennifer found the family to be unnaturally close. There was Barry; his father, Allen; Allen’s wife, Hilary (whose sister, Stacey Glazer, works for the Trump Organization as a risk-management coordinator); and their younger son, Jack, who works for Ladder Capital, a real-estate-investment trust whose subsidiaries have loaned Donald Trump more than $280 million for four of his properties.

Jennifer says Allen would wander the house in his pink pajamas while Hilary sat on a couch, knitting in her nightgown. But, according to Jennifer, while Allen presents a quiet and buttoned-up demeanor at work, or out at Trump clubs, where he is unfailingly polite, at home he could be quite critical, owing, she believes, to his dissatisfaction with the wide gulf between the gilded life he lives within Trump World and the workaday one that he’s relegated to outside it.

Of their life in the 90s in Wantagh, Jennifer says, “I was in a house where anything goes.... I knew from the beginning it was unhealthy. It was too enmeshed.”

But what she describes as the family’s dysfunctional closeness held a certain appeal, given that her own parents divorced when she was 14 and she rarely saw her father. She and Allen became close, she says. Although, to be sure, they did not communicate nearly as frequently as Allen and Barry.

“Barry calls his father all the time,” she says. “‘Should I order the burrata or not? … Should I order the eggs?’ He doesn’t make any decisions without asking his dad.” According to Jennifer, Barry “always ran to [Allen] like a six-year-old who had fallen down and scraped his knee.”

According to Jennifer, when Allen is not talking to his son, he is talking to Trump.

“They talk tirelessly,” she says, and Trump, she believes, is the focus of Allen’s life. “Allen stopped drinking because Donald doesn’t drink.

When, according to Jennifer, Allen made her marriage to Barry contingent upon her converting to Judaism, she complied. “I convinced myself I was doing it as a discovery,” she says. “I went to the mikvah. Barry said, ‘Don’t ever use this against me.’”

Even though by this point Jennifer knew the Weisselbergs well, she says she still had no idea what she was getting into. “You might think that you’re signing that ketubah and you’re going to have a normal life and a normal marriage, but they slowly eat away at your soul,” she says. “There’s no respect, there’s no gratitude, but yet they maintain full control.... It’s manslaughter of the soul.... It’s insidious.” (The allegations in this story were shared with Allen Weisselberg and Barry Weisselberg. Both declined to comment.)

Allen would seemingly do anything for his son. In 2000, a little more than five years after Jennifer met him, Barry was unemployed. So when his father offered him a $174,000 salary to be an assistant manager at what was then called Trump Rink, he took it.

Donald and Melania Trump gave them a one-bedroom apartment in Trump Parc East, at 100 Central Park South, across the street from Wollman Rink. It was their wedding present. Or so Jennifer thought.

According to Jennifer, Allen told Barry, “You play hockey and you D.J., so it’s a good fit.” “And, really,” Jennifer continues, “at that time when you can’t get another job, it’s not a bad thing that your dad would find a place for you.”

Jennifer and Barry at Trump’s inauguration.

By this point, Barry had moved into Jennifer’s North Bellmore, Long Island, cottage, and it was there, in July of 2000, that she says Barry punched her so hard in her left eye that her eye came out of its socket. “I’ll never forget it,” she tells me. “My whole world stopped, as if I was shot.”

Barry, she says, took her to an eye doctor who repaired her eye. Barry “didn’t want me to go to a hospital,” she says. “That was the day the trauma started.”

According to the family-offense petition that she filed on August 19, 2020, with the Family Court of the State of New York, Jennifer alleges that “the assault [of July 2000] has caused partial blindness in [her] left eye.”

But, according to Barry’s sworn affidavit of June 16, 2018, this incident “never happened and is a complete lie.... Jennifer has been wearing glasses since I have known her and her eyes have been getting worse as she gets older.... The police were never contacted, no report was filed and there were no witnesses to corroborate this fiction.”

While this incident is in dispute, and is now among Jennifer’s claims being investigated by the domestic-violence unit of the Manhattan district attorney, there is little doubt the couple had a contentious relationship. In 2008, for example, the police came to their Central Park South apartment. As per her family-offense petition, Jennifer says, this was because Barry had pushed her “against the apartment window with such force that [she] feared for her life and safety,” while Barry, as per his sworn affidavit, writes that “she, not me, slapped me in the face.” According to Jennifer, police officers came to her apartment unbidden, because they had witnessed Barry attacking her through the apartment’s park-facing windows. But then suddenly Allen and Hilary showed up as well. Jennifer says Allen threatened her not to press charges, and in the end no arrests were made.

“It’s That Dual Life”

In retrospect, says Jennifer, the fact that the Trump Organization wanted Barry living so close to the rink makes sense, given that Barry was Trump’s eyes on the cash. Or, as Jennifer succinctly puts it, the rink was “supposed to be this iconic place in New York City, but it was turned into a cash dumpster for Donald.” (These allegations were shared with the Trump Organization, which did not respond to a request for comment.)

Allen would seemingly do anything for his son. In 2000, a little more than five years after Jennifer met him, Barry was unemployed. So when his father offered him a $174,000 salary to be an assistant manager at Trump Rink, he took it.

According to Jennifer, Barry worked every holiday and every weekend at the rink and longed to work at another Trump property such as Mar-a-Lago. But, she says, “Donald would not let him leave the rinks.... When you’re compensated by Trump with apartments and tuition”—her children’s private-school tuition, she alleges, was paid for in part by Trump and in part by Allen—“you start doing [questionable] stuff, whether it’s … not confronting the taxes head-on and it’s 10 or 20 years, they have got you in a chokehold.... How are you going to leave? Your résumé and W-2 says for 20 years you made $200,000.”

According to Barry’s 2019 sworn statement of net worth, the private-school tuition of their two children was paid for by Allen and Hilary, but Jennifer believes that Allen was reimbursed for at least some of those payments by the Trump Organization. If this were accurate, it might help explain why, in Barry’s sworn deposition of August 2018, when Jennifer’s attorney asked him, “To your knowledge, has Donald Trump personally paid for any of the household [sic] family or your personal expenses during your marriage?,” Barry answered, “I don’t know.”

“It’s that dual life,” says Jennifer. “You’re living in an apartment on Central Park South and then you’re sitting poolside with Don Jr. and his wife at Trump National Briarcliff. It’s that smoke and mirrors of you feel so indebted and you feel so grateful. Allen was acting like he was being so generous, but he is using Donald Trump’s resources and compensating with Donald Trump’s assets. I thought Allen was paying for it out of his salary.... But the truth is that the Weisselbergs were not contributing. It was coming from the Trump Organization. Allen was using Donald Trump’s resources to be the man, the micro-Donald.”

When Trump won the election in November 2016, Jennifer and Barry, along with all the Weisselbergs, headed to D.C. for the inaugural, ball gowns and tuxedos in tow. But, according to Jennifer, Allen was terrified that he’d become co-trustee of a trust—the Donald J. Trump Revocable Trust—that the Trump Organization set up to hold assets for “the exclusive benefit of the president” just days earlier.

“I don’t think he wanted to be responsible for this company,” she says. “But he had to because Donald became president. Then Barry is bragging to me that he’s up in Trump Tower.”

That Mother’s Day, he sent her a card.

“I really hope you know what a great Mom you are,” he wrote. “I wish you wouldn’t be so hard on yourself. You have a great life, great kids, just enjoy it! Don’t sweat the small stuff, be strong, be happy and be proud of what you have accomplished as a mother. These 2 kids are amazing. Without you they wouldn’t be. Look at all the good around you—focus on that, nothing else. Happy Mother’s Day. Love, Barry.”

Five months later, Barry was seeking a divorce.

“It was a setup,” says Jennifer. What Barry really wanted, she says, was to live with his girlfriend, a woman who she says worked as a cashier at Wollman Rink.

Skimming the surface: Trump at Wollman Rink with Mark Halperin.

The nasty divorce and custody battle would lead to horrible claims and counterclaims, and Jennifer was out-lawyered and out-spent, even at times reduced to acting as pro se—representing herself, despite having no legal training.

But for investigators from the offices of the Manhattan district attorney and the New York State attorney general, the legal battle had a major upside: it created on-the-record statements that gave them visibility into potential criminal activity inside the Trump Organization.

For example, when Barry initiated their divorce, he and Jennifer were living in an apartment on West End Avenue whose $7,900 monthly rent Allen was paying—a bizarre situation considering that, at least in Jennifer’s mind, the bookkeeper, Allen, is “the cheapest person on earth.”

And yet, she says, there was Allen, every year on January 1⁠—starting back in 2013, when they first moved in⁠—handing Barry 12 rent checks, each one made out in advance for the coming year.

According to Jennifer, these payments, which totaled more than $500,000 over the course of the six years that her family lived there, were not that different from the monthly checks⁠ through which the Trump Organization reimbursed Michael Cohen—allegedly for his legal services⁠—to pay off Stormy Daniels. Only in this case, Jennifer believes that it was the rent Allen paid for her family’s apartment which may have been the Trump Organization’s money.

According to the New York City accountant, if the rent money were in fact originating from the Trump Organization, “then it’s clearly another case of disguised compensation.” But if the rent money were in fact originating from Allen Weisselberg personally, then the only person who would have to pay tax on that gift of rent would be Allen himself, as when it comes to gifting, “the person receiving the money is not taxed.”

Owing to their grand-jury subpoena of Jennifer last week, the District Attorney’s Office now not only has these rent checks but all of Jennifer’s financial data from her marriage and divorce. And having also subpoenaed Allen’s personal bank records, investigators are now assembling a more complete picture of the Weisselberg finances and how they fit into the Trump Organization puzzle.

In addition to the potential tax and compensation issues resulting from their former homes, there is a third property in which Barry and Jennifer alternated living over the course of a year, as they began sharing fifty-fifty custody of their children, and they never paid for that either: a one-bedroom on East 61st Street owned by⁠—who else?⁠—the Trump Organization.

“Is rent being paid for your use of that apartment?,” Jennifer’s lawyer asked Barry in his August 2018 deposition.

“It’s a corporate apartment that I was given temporarily,” Barry replied.

Jennifer’s attorney persisted: “Is rent being paid for the apartment?”

Barry replied⁠—perhaps predictably, by this point⁠—“I don’t know.”

While people who know both Jennifer and Barry report that Barry is well liked in his children’s school community, it is a reputation that seems difficult to reconcile, not only with his alleged abuse of Jennifer but also with what seems to be his desire to alienate his ex-wife from her children. A clue to at least some of this vast discrepancy may lie in the retainer agreement that Barry signed with Aronson, Mayefsky & Sloan, the law firm representing him throughout the divorce and the ongoing custody litigation. According to the agreement, the firm is authorized to send its bills to “the email address noted above,” which is Allen’s. (Curiously, the Ladder Capital e-mail of Barry’s younger brother, Jack Weisselberg, is listed as well.)

“Allen has been the man behind the machine,” says Jennifer. “Allen’s [goal] in every deal is to protect loose ends for Donald. That’s his art of the deal.” And when it comes to her divorce and custody battle, she says, “I think I’m a loose end they just wanted to tie up.”

That theoretical goal was nearly accomplished last February, when forensic psychiatrist Dr. William Kaplan, who evaluated Jennifer, testified that he was deeply concerned about her, and that “she feels over a long period of time victimized by a conspiracy initiated by her ex-husband Barry, and his family to impoverish her. And … destroy her.” Judge Lori Sattler ordered Jennifer taken in handcuffs to Bellevue Hospital, and granted Barry temporary custody of their children. But after an evaluation, Bellevue determined that Jennifer did not need its care and discharged her from its emergency room.

It was seven months later that Jennifer began cooperating with investigators, including, eventually, the Manhattan district attorney, whose offices are in the same complex where Jennifer’s custody battle continues.

But the bigger irony may be that in financing his son Barry’s litigation against her, Allen Weisselberg may also unwittingly and indirectly be financing his own demise. And if the investigations go the way that many believe they will, and Allen were to flip, they just might also lead to the demise of Donald J. Trump.

Johanna Berkman is a New York–based writer