Prosecutors Are Turning Up the Heat on the Trump Organization Employee Who Could Take Trump Down

As part of its criminal investigation into possible bank, tax, and insurance fraud by Donald Trump, Cyrus Vance Jr.’s Manhattan District Attorney’s Office has for months been working to flip Allen Weisselberg, the company’s longtime CFO who has described himself as the ex-president’s “eyes and ears” at the firm. Last month a seemingly significant development occurred on that front when Jennifer Weisselberg, Allen’s former daughter-in-law, turned over a trove of documents to Vance‘s office concerning the finances of both Allen and his son, fellow Trump Organization employee Barry Weisselberg. As The Washington Post reported, said 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 [Barry managed] and working to ascertain whether the proper taxes were paid.” Asked during a 2018 divorce deposition about whether taxes were paid on the Trump-owned apartment where he’d lived for free, for example, Barry said he wasn’t sure. Pressed to clear up discrepancies between what he said he earned and what he reported on tax forms to the IRS, the younger Weisselberg could only offer, “I’m not an accountant. I know what I make. I’m not too sure of certain things.”

In other words, Vance’s office is currently in possession of the kind of information that could conceivably get one of Trump’s highest-ranking employees to cut a deal with prosecutors, and according to The Wall Street Journal, there may be more where that came from:

New York prosecutors have subpoenaed a Manhattan private school as they seek the cooperation of the Trump Organization’s chief financial officer in their investigation of former president Donald Trump and his company, according to people familiar with the matter. The subpoena seeks information from Columbia Grammar & Preparatory School, where grandchildren of Trump Organization CFO Allen Weisselberg are students, the people said. From 2012 to 2019, more than $500,000 of the children’s tuition was paid for with checks signed by either Mr. Weisselberg or Mr. Trump, the two children’s mother, Jennifer Weisselberg, told The Wall Street Journal. She is the former wife of Mr. Weisselberg’s son Barry.

Ms. Weisselberg said she told Manhattan prosecutors that she and Barry understood the tuition payments to be part of her ex-husband’s compensation package at the Trump Organization, where he worked. Former prosecutors not involved in the probe said the Manhattan District Attorney’s Office could be examining whether the Weisselbergs evaded taxes with the tuition-payment arrangement.

While none of the Weisselbergs have been accused of wrongdoing, as the Journal notes, “prosecutors often seek the cooperation of someone possibly involved in a crime to obtain confidential information and provide a potential road map to records or documents. Typically, prosecutors offer a potential defendant leniency in exchange for their help. Putting pressure on a possible defendant’s family is one way to encourage cooperation.” People who know Allen Weisselberg told the Journal that he is loyal to the Trump Organization and were skeptical of the idea of him turning on the former president. On the other hand, he already cooperated with prosecutors investigating Trump on two separate occasions—during both the 2018 federal probe into hush money payments and the 2017 New York attorney general’s investigation of the Donald J. Trump Foundation, which was ultimately forced to shutter. As Weisselberg’s ex-daughter-in-law said last month: “Trump doesn’t care about Allen, but Allen knows every bad thing he ever did.”

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