Meet the Woman Who Could Send Donald Trump to Prison

As the Manhattan District Attorney’s criminal investigation into potential bank, tax, and insurance fraud by Donald Trump ramps up, there are a number of key figures whose names likely sends shivers down the ex-president’s spine (or would if his handlers had actually explained the seriousness of the situation to him, rather than keeping him in a hermetically sealed bubble wherein he’s only told the election was stolen from him and some day soon he’ll be crowned President for Life). Obviously, one of those people is Cyrus Vance Jr., the veteran D.A. running the investigation who obtained Trump’s tax returns in February. Another is Mark Pomerantz, the prosecutor brought onto the case who helped put John Gotti behind bars. Additionally, there’s Morgan Magionos, who helped bring down former Trump aide Paul Manafort. Yet perhaps the most worrisome figure is an individual who hits closer to home, whom Trump has known for years—Jennifer Weisselberg, the former daughter-in-law of longtime Trump Organization CFO Allen Weisselberg.

As The Washington Post reported last month, Vance’s office has been “delving deeply into the personal and financial affairs” of the senior Weisselberg, with the goal of getting him to flip and become a witness against Trump. The D.A. is said to be focused on two of Weisselberg’s adult sons, “a tactic that could be an effort to increase pressure on the elder Weisselberg.” One of those sons is Jack Weisselberg, who works at Ladder Capital Finance, which, according to The Washington Post, happened to loan the Trump Organization more than $270 million. Another is Barry Weisselberg, a Trump Organization employee who managed the Wollman ice rink for the company before the city ended its contract. On Thursday, Barry’s ex-wife, Jennifer Weisselberg, reportedly turned over a trove of financial documents to Vance’s office, which, according to Jennifer, contain information for her ex-husband’s bank accounts and credit cards, as well as his statements of net worth and tax filings. “My knowledge of the documents and my voice connect the flow of money from various banks and from personal finances that bleed directly into the Trump Organization,” Jennifer said last week. And according to a new report, those documents contain some extremely interesting information with regard to laws that may have been broken.

Per the Post:

Those records were entered into the couple’s divorce proceedings, which began in 2017, and some were obtained by The Washington Post this week along with a transcript of the deposition Barry Weisselberg gave as a part of that legal process. The documents show an array of payments and perks that Barry Weisselberg and his family received as a result of his employment for Trump’s company over 18 years, likely raising key questions for investigators analyzing the finances of the cash-only skating rink and working to ascertain whether the proper taxes were paid…. In the deposition, Weisselberg acknowledged making errors in explaining information about his finances. He said, for instance, that he had forgotten that he shared an investment account with his father and he misstated his salary, prompting interjections from his attorneys when repeatedly confronted with contradictory information, the transcript shows.

He could not answer some questions about his taxes, the transcript shows. When asked whether taxes had been paid on the corporate apartment where his family previously lived, he said he wasn’t sure. Asked how the company determined the size of his bonuses, which tallied about $40,000 annually from 2015 to 2017, he said he had “no idea.” When pressed in the deposition to explain discrepancies between what he said he earned and what he reported on tax forms for the Internal Revenue Service, he said: “I’m not an accountant. I know what I make. I’m not too sure of certain things.”

Despite earning $200,000 a year for “as long as he could remember,” Weisselberg said in the deposition, according to the Post, that he and Jennifer lived rent-free in Trump-owned apartments, adding that he did not know how taxes on the property were handled. (In addition, his father paid most of his living expenses, including $7,900 in monthly rent for a non-Trump-owned apartment where the couple later lived, $49,000 a year for each of his kids to attend private school, $25,000 each for overnight camp, $2,200 for his daughter’s Hebrew school, and $546 a month for a leased Range Rover.) Speaking of Barry Weisselberg’s financial situation, the documents Vance’s office got a hold of last week have raised a number of questions, according to Air Mail:

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.)

As for Barry Weisselberg’s job managing the Wollman Rink, his ex-wife has suggested he was a gofer for Trump‘s crimes:

According to…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.”

Neither the senior or junior Weisselberg responded to Air Mail’s request for comment, nor did the Trump Organization. Last month, Jennifer Weisselberg told Insider, of the Trump business: “They want you to do crimes and not talk about it and don’t leave. It’s so controlling. And both [the District Attorney and New York Attorney General] have discussed that because they need to know how they operate.” As for Allen Weisselberg, who had described himself as Trump’s “eyes and ears” at the company, he’s already cooperated with prosecutors investigating Trump on two previous occasions— with the 2018 federal probe into hush money payments and the 2017 New York attorney general’s investigation of the Donald J. Trump Foundation, making him a worrisome target of the D.A. “Trump doesn’t care about Allen, but Allen knows every bad thing he ever did,” his ex-daughter-in-law told Air Mail.

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