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How Jennifer Weisselberg could cause Donald Trump's downfall

The ex-daughter-in-law of Trump's CFO could be the first domino to fall.

UPDATE (Aug. 18, 2022, 10:53 a.m. ET): Former Trump Organization CFO Allen Weisselberg pleaded guilty on Thursday to criminal charges tied to his indictment in a tax fraud case involving the company's business dealings. As part of his plea, Weisselberg will pay nearly $2 million in taxes, interest, and penalties and serve five months in jail.

Jennifer Weisselberg spent last week making the rounds at media outlets to announce that she has been interviewed "multiple times" about the finances of former President Donald Trump and the Trump Organization. Word on the street is that prosecutors in the Manhattan district attorney's office are looking to flip the chief financial officer of the Trump Organization, Allen Weisselberg, whose son Barry was married to Jennifer for 14 years.

Allen is Trump's longest-serving executive at the Trump Organization; he has gone from being just a bookkeeper in 1973 to his current role atop the company. He is known for his loyalty and years of service not only to the former president but also to his father, Fred Trump. Barry and Jennifer divorced in 2018, and by her own admission, the "bitter" divorce battle resulted in her losing custody of her children. So while this is all very dramatic, the question remains: Why would Manhattan DA Cy Vance be interested in what Allen Weisselberg's former daughter-in-law has to say?

The short answer is that Jennifer could serve as a Rosetta Stone for this whole investigation, becoming an invaluable key to translating previously indecipherable documents. In August 2019, a New York grand jury issued a subpoena to Mazars USA LLP, Trump's personal accounting firm, seeking Trump's tax returns from 2011 until the present. After a legal battle that went all the way to the Supreme Court, Mazars produced millions of pages of documents, including tax returns, financial statements, engagement agreements, documents relating to the preparation and review of tax returns, and work papers and communications related to the tax returns. Vance also received the source documents for the tax returns, including raw financial data.

That windfall is huge, as Vance is reported to be focusing his attention on possible tax fraud by the Trump Organization. He is also reported to be looking into potential bank fraud and other schemes to defraud, including the misrepresentation of the valuation of properties and other assets to obtain loans and other tax breaks.

The records turned over so far will remain confidential as part of the grand jury investigation, but you can rest assured that Mark Pomerantz, whom Vance hired as a special assistant district attorney to assist in this investigation, will be combing through the records to find evidence of any malfeasance on the part of Trump, his associates and his company. Pomerantz prosecuted the infamous mob boss John A. Gotti — fitting given the comparisons between Trump and the moblike system he uses to run his life and business. Vance has also hired forensic accounting specialists at FTI Consulting to help analyze the records.

Meanwhile, former Trump "fixer" Michael Cohen is reported to have spoken with Vance's team on eight different occasions. Cohen has indicated that Allen Weisselberg was a party to several conversations between Cohen and Trump and that he could be a source of direct information about what Trump said and did over decades. Cohen has also emphasized Allen's importance to a potential prosecution of Trump and his businesses, as the CFO knows where the proverbial bodies are buried in Trumpland.

Vance has issued new subpoenas in recent weeks to get as much transparency into Trump's business dealings as possible. It's obvious that Vance hopes for evidence that would persuade a grand jury to return an indictment alleging criminal offenses. And the best people who can interpret these documents and answer the "why" and "how" and "who" questions are those who knew Trump and worked intimately with him over the years.

As a true "insider" and someone who had 25 years of insight and exposure to Trump and his personal dealings, Jennifer Weisselberg can explain some of the moves Trump has made over the years. But her real value for investigators isn't so much in what Trump might have said or done in front of her. It's what her ex-father-in-law might have said about Trump and his business at the dinner table, during family vacations spent together or on telephone calls. She can share the details of her life and her interactions with Trump and the Trump children, as well as countless others, acting as a gateway to help Vance get to Allen.

The best people who can interpret these documents and answer the “why” and “how” and “who” questions are those who knew Trump and worked intimately with him over the years.

Consider the following: Weisselberg told NBC News that she believed that as a wedding present, Trump gifted her and her ex-husband an apartment overlooking Central Park. For seven years, they did not pay any rent and had to pay only for their utilities. Their apartment sold for $2.85 million in 2014 and was listed at $4,950 a month for rent before the sale, according to New York City housing records. Her ex-husband, Barry, managed Trump's ice rink, Wollman Rink, in Central Park before the city ended its contract with the Trump Organization this year. Generally speaking, things like free rent are viewed as taxable income for employees, unless there is a tax exception — which seems doubtful here.

Weisselberg also claims that Trump and her former in-laws paid for most of their living expenses while they were married. She told Reuters that she has provided to Vance's team, among other things, the tax and financial records for her and her ex-husband. Prosecutors can now not just look for improprieties in reporting in those filings but also compare them to the tax disclosures by Trump and the Trump Organization. (Weisselberg also said she has spoken with New York Attorney General Letitia James, whose office is conducting a civil inquiry into the Trump Organization.)

Thanks to Jennifer, one of Allen Weisselberg's children may wind up looking down the barrel of potential criminal charges. Nothing incentivizes a parent more than having a child in jeopardy. And if Allen can save his son by helping Vance, then maybe Trump has cause for concern.