Trump Organization chief financial officer Allen Weisselberg—a man who once claimed to be Trump’s “eyes and ears” with regard to his money—has twice cooperated with investigations into the ex-president’s finances. First, he cooperated with the New York attorney general’s probe of the Donald J. Trump Foundation in 2017, which resulted in a $2 million penalty for Trump. And then he cooperated with federal prosecutors’ 2018 inquiry into hush-money payments that Michael Cohen paid on Trump’s behalf to porn star Stormy Daniels (for which Weisselberg received limited immunity and Cohen received a prison sentence).

All this cooperation—for investigations into the dealings of a former U.S. president—and yet most Americans know nothing about the mustachioed Long Island bookkeeper who has kept Trump’s books and paid his bills for more than 30 years, other than possibly having once seen him on The Apprentice, back in 2004.

But if Manhattan district attorney Cyrus Vance Jr. has his way, all that could soon change. Vance, who recently got access to Trump’s tax returns, is conducting a fast-moving investigation into the former president’s finances. He has brought in Mark Pomerantz, an attorney who successfully prosecuted Gambino-crime-family boss John A. Gotti on racketeering charges back in the 90s, to run it.

At the same time, New York State attorney general Letitia James is conducting an investigation of her own, one which sources say is more narrow in scope and could result not only in civil charges but, perhaps, also criminal charges. It’s being run by Gary Fishman, who was chief of the A.G.’s Criminal Enforcement and Financial Crimes Bureau, which prosecutes complex and large-scale financial crimes, and a source close to the investigation believes that this one is further along.

The man in the shadows: Allen Weisselberg, center, chief financial officer of the Trump Organization, who once said he was Trump’s “eyes and ears” in terms of finances.

Together they represent a threat broader than any Trump is known to have faced. Most intriguingly, it appears that significant breaks in these cases are coming from an unexpected quarter: the highly contentious divorce of Allen Weisselberg’s son, Barry, who has spent the past 21 years working for the Trump Organization—as manager of Central Park’s Wollman ice-skating rink. Or at least he did until the end of this month, when the city’s contract with the Trump Organization, which had entitled Trump to operate Wollman (a largely “cash only” business), as well as Lasker Rink and the Central Park Carousel, all of which Weisselberg oversaw, expires. (The city, noting Trump’s role in the incitement of the Capitol insurrection, has chosen not to renew it.)

According to his former wife, Jennifer, Barry’s real job was to be Trump’s eyes on the cash, and as such, she says, once a week he would collect the money, not just from the rink but from all three Trump-run park properties, and walk it to his father’s office in Trump Tower.

“What does Allen do with it?” Jennifer asks. “I don’t think all the cash was reported. It was for Trump. That’s why he wanted [Barry] there so bad.”

The 45-year-old Weisselberg’s divorce from the 49-year-old Jennifer, which has been mired in post-judgment litigation since January of last year, has exposed not only his convoluted finances but also, indirectly, those of his father—and most fortuitously for prosecutors, the murky finances of the Trump Organization itself.

As a result, investigators may use the threat of potential criminal charges against Barry, his father, or both, to put pressure on Weisselberg Sr.—one of Trump’s most loyal and longest-serving aides—to “flip,” turning him into a witness against Donald Trump.

“They got Capone because they got the accountant to flip on him,” says a former assistant district attorney in Manhattan. “That’s an old trick.”

Or, as Jennifer succinctly puts it, “Trump doesn’t care about Allen, but Allen knows every bad thing he ever did.”

She’s now telling prosecutors what she knows—while trying to survive what she claims is an extreme version of the character destruction that those who try to escape the Trump grip all too often suffer.

“It’s All One”

When 18-year-old Jennifer (née Zarnowiec) Weisselberg, a Catholic ballerina from Longwood, Florida, left for New York City just one hour after graduating from high school, in June 1990, she had a single mission: to pursue her dream of becoming a professional dancer.

That she would accomplish her goal only to wind up living the life of a wife and mother may be no great surprise. But that that life would dissolve overnight when, after 14 years of marriage, Barry Weisselberg initiated their divorce via an emergency judicial intervention that he had issued against her before she even hired an attorney, and that he would then, just two years later, take temporary full custody of their two children through yet another emergency judicial intervention, was unimaginable.

Barry Weisselberg takes a break in order to give skating lessons to Miranda Lambert.

Yet perhaps most improbable of all is the fact that she would wind up becoming a witness in both the civil and criminal investigations into a former U.S. president.

It all started last September when, home in Florida visiting family, Jennifer got a call from the Attorney General’s Office. “I did not feel intimidated,” she says. “After what I’ve been through with the men in my life, dealing with the Weissselbergs and Trump, it felt like a business call.”

After several hours-long interviews in which Jennifer was asked questions about Allen Weisselberg, the Trump children, and certain Trump-owned properties, including Mar-a-Lago, 40 Wall Street, and Seven Springs (the Westchester estate), the A.G. requested she provide financial documents that she had accrued over the course of her marriage, and she complied. Soon the Manhattan district attorney would find out she was talking to the New York State Attorney General’s Office, and they would come calling as well.

“Barry doesn’t pay his own bills,” says Jennifer of her former husband. “Not his car, the kids’ school, or the kids’ camp.” It is, she says, his father, the bookkeeper, Allen, who pays. “I’m basically in a divorce with Allen and Allen’s money and Allen’s finances. And they bleed right into the Trump Org.” (Neither Barry nor Allen responded to AIR MAILs requests for comment.)

The Trump Playbook

That the Trump Organization seems to destroy the life of people it no longer needs, or can blame for its own wrongdoing, is no secret. After serving one year of his three-year sentence in a federal prison in upstate New York, Michael Cohen is now, due to the coronavirus, serving the remainder of his sentence in home confinement—in his Trump Park Avenue apartment. Then there’s Stephanie Winston Wolkoff, once Anna Wintour’s Met Ball doyenne, who was also, for a time, Melania’s best friend. She was asked to help plan Trump’s inauguration, only to then find her reputation in tatters when federal prosecutors began investigating how the event’s $107 million budget got spent. When she wrote a tell-all defending herself, the U.S. Justice Department sued her and sought to seize her profits, alleging she had violated an NDA. (The Trump Organization did not respond to Air Mail’s request for comment.)

“They got Capone because they got the accountant to flip on him,” says a former assistant district attorney in Manhattan. “That’s an old trick.”

As bad as these chapters in the Trump playbook are, Jennifer’s story seems the most grotesque. The mother of two has been left with scant financial resources—she recently liquidated her half of Barry’s Trump Organization 401(k) in order to get funds to hire new legal representation—and is on the brink of being evicted from her three-bedroom rental on the Upper West Side, for which Allen Weisselberg is the guarantor.

Given that Barry Weisselberg has not paid her $4,166 monthly alimony since February 1, 2021, and she is not presently working, Jennifer has not paid her rent.

Theoretically, paying is now the responsibility of her guarantor—Weisselberg Sr.—but he has not done so. As a result, her landlord is suing them both for $54,450 in unpaid rent. And because her apartment lease was one of the few things registered in her own name over the course of the last many years—“Barry never put me on a single apartment lease,” she says, nor a bank account, credit card, or car lease because “Allen or the Org., or really just the Org., was paying”—the impact of her breach of contract may be profound. “Allen,” she claims, “is ruining my credit.”

Jennifer and Barry at their wedding, with the Trumps.

Meanwhile, Barry may now be facing some serious finance-related issues of his own. When the district attorney, acting on a grand-jury subpoena, took possession of three boxes of Jennifer’s financial records from her apartment this past Thursday morning, included in the trove was Barry’s October 1, 2020, “statement of net worth” and “statement of income from all sources,” both of which he swore were “true and correct … under oath, subject to the penalties of perjury.” Also attached to these documents were his 2019 tax returns.

According to these documents, Barry’s 2019 pre-tax income was $223,471 and, as per his supplement to Form 1040, his total “withholding from wages”—i.e., taxes—were $59,245, thereby netting him $164,226 post-tax. He also reports annual expenses of $466,500. And yet, even after deducting the $130,272 that he indicates his parents, Allen and Hilary, pay for his children’s private-school tuition and camp, from these annual expenses, Barry is still left with a shortfall of $172,002.

Given that he reports that his bank and investment accounts—excluding his 401(k)—total just $14,123, they do not even come close to making up the difference, leaving this area fertile ground for the investigators and forensic accountants currently combing through the Weisselberg finances. (The Manhattan D.A. has also subpoenaed Allen’s bank records.)

Jennifer, meanwhile, has no health insurance. She has also had past struggles with substance abuse. And, according to a Family Offense Petition that she filed with the Family Court of the State of New York on August 19, 2020, Barry physically abused her during both their marriage and the eight-year relationship that preceded it, allegations that the Domestic Violence Unit in the Manhattan District Attorney’s Office is currently investigating.

That said, in a sworn affidavit on June 16, 2018, Barry insisted that Jennifer’s claims against him “regarding physical abuse” were unfounded—“I have never hit her,” he wrote; “I repeat, I have never raised a hand toward Jennifer”—alleging that she was physically abusive to him. Barry also previously sought an order of protection against Jennifer in October 2017, citing “bodily harm,” but later withdrew the request.

“Trump doesn’t care about Allen, but Allen knows every bad thing he ever did.”

Now, nearly two and a half years after her divorce was supposedly finalized, Jennifer finds herself the subject of abusive litigation, trapped in the misogynist version of a Kafka-esque nightmare.

“What Barry and Allen and their lawyers are trying to do is distract from Trump’s finances,” says Zoe Applbaum, Jennifer’s legal advocate from Steps to End Family Violence, a program run by the human-services nonprofit Rising Ground. “Barry says [Jennifer is] either a drug addict or an alcoholic or mentally incompetent. He says ‘either/or’ to all of them, but he has no proof of any of them, so the court keeps making her take all these tests, which come back clean. He’s throwing things against a wall to see which sticks.... It’s textbook abuse in the sense that domestic violence is about coercive control.”

Other than a single, very brief in-person visit with her two children in a city park this past January 20, which just happened to be the day of Biden’s inaugural, and for which she paid a $1,500 retainer plus a $300 fee to a court-appointed supervisor, Jennifer has not seen her children (other than in court-supervised Zoom calls) since February 5, 2020.

And yet now, more than one year after the judge presiding over her case sent her to Bellevue Hospital for an extensive psychiatric assessment and overnight examination—after which, in the words of her personal psychiatrist, Jennifer was “deemed not to require any acute care and was discharged home”—she is still not allowed to attend any of her children’s school functions, or even give them birthday presents. Once upon a time she was a class parent, a grade representative, a dedicated school volunteer who ran fundraising events, and someone who attended parenting classes. Now she is hardly allowed to be a parent at all.

Sad and messy as all these personal issues are, they may be of great value to prosecutors going after Trump. According to Jennifer, “My divorce and the criminal investigation—it’s all one.”

Johanna Berkman is a New York–based writer