The Odds Of Donald Trump’s CFO Flipping and Helping Send Him to Prison Just Shot Up

One of the key figures in prosecutors’ quest to actually put Donald Trump behind bars is Allen Weisselberg, the longtime Trump Organization chief financial officer. With the company for decades, Weisselberg has described himself as Trump’s “eyes and ears” at the firm and presumably, in the event that any laws had ever been broken, would know about them. In fact, as his ex-daughter-in-law, Jennifer Weisselberg, put it to Air Mail earlier this year, “Allen knows every bad thing [Trump] ever did.” That kind of witness would obviously prove invaluable to the government officials trying to make their case, which is why, unsurprisingly, Manhattan District Attorney Cyrus Vance Jr. has been working for months to “flip” Weisselberg and get him to cooperate against the ex-president. And while it’s not clear where Vance’s office is in its efforts, it appears the Trump Organization CFO may soon be under intense pressure to cooperate with the office of New York Attorney General Letitia James, which just happens to be collaborating with the D.A.

The New York Times reports that Weisselberg is officially under criminal investigation by James’s office, which is examining if taxes were paid on “fringe benefits” Trump gave him, including cars and thousands of dollars in private school tuition for at least one of Weisselberg’s grandchilden.

Per the Times:

The focus on perks and Mr. Weisselberg overlaps with the Manhattan district attorney’s long-running criminal fraud investigation of Mr. Trump and his family business. The district attorney’s office has been investigating the extent to which Mr. Trump handed out fringe benefits to some of his executives, including Mr. Weisselberg, and whether taxes were paid on those perks…In general, fringe benefits—which can include cars, flights, and club memberships—are taxable, though there are some exceptions. Companies are typically responsible for withholding such taxes from an employee’s paycheck.

Rather than risk bumping into each other, the two investigative offices recently began collaborating, another person with knowledge of the matter said. Two assistant attorneys general from Ms. James’s office have joined the district attorney’s team, which has been seeking to turn Mr. Weisselberg into a cooperating witness against Mr. Trump and the Trump Organization, people with knowledge of that effort said…. In addition to the fringe benefits, Ms. James and the district attorney, Cyrus R. Vance Jr., have examined whether Mr. Trump’s company inflated the value of his properties to obtain favorable loans and lowered the values to reduce taxes.

For months, Mr. Vance’s office has pursued Mr. Weisselberg as a potential cooperating witness, people with knowledge of that effort have said. Mr. Vance’s prosecutors, who have paid particular attention to Mr. Weisselberg’s fringe benefits, subpoenaed records from Mr. Weisselberg’s bank and the private school in Manhattan that his grandchildren have attended, The Times has reported. Mr. Weisselberg’s former daughter-in-law, Jennifer Weisselberg, has said that prosecutors had asked her about the tuition payments as well as gifts her ex-husband, Barry Weisselberg, received from Mr. Trump, including an apartment on Central Park South and several leased cars.

As The Washington Post reported in March, Vance’s office—and now, seemingly James’s—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 additionally be focused on both Barry Weisselberg and the other son of the CFO, Jack Weisselberg, “a tactic that could be an effort to increase pressure on the elder Weisselberg.” Jack works at Ladder Capital Finance, which, according to the Post, happened to loan the Trump Organization more than $270 million. Barry—the ex-husband of Jennifer—is a Trump Organization employee who managed the Wollman ice rink for the company before the city ended its contract. Last month, Jennifer turned over a trove of financial documents to Vance’s office, which 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,” she said. And according the Post, those documents contain some extremely interesting information regarding laws that may have been broken:

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 [his divorce] 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,” Barry said in the deposition that he and Jennifer lived for free in Trump-owned apartments while they were married, adding that he had no idea how taxes on the property were handled. (Additionally, his father, Allen, paid some 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.)

According to analysis of the financial documents by Air Mail, the information contained within raise more questions than they answer, including about the possibility of tax fraud:

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.

When it comes to Barry’s gig for the Trump Organization, his ex-wife told reporter Johanna Berkman that Barry’s key responsibility was to keep an eye on the cash at Trump-run park properties, which he would pick up weekly and bring to his father’s office at Trump Tower. “What does Allen do with it?” Jennifer asked. “I don’t think all the cash was reported. It was for Trump. That’s why he wanted [Barry] there so bad.”

Earlier this month, the Manhattan D.A. subpoenaed the private school Allen Weisselberg’s children attend; according to his ex-daughter-in-law, from 2012 to 2019, more than $500,000 in tuition payments were paid for with checks signed by either Weisselberg or Trump, which could have been a way for the Trump Organization to avoid taxes.

Neither Allen nor Barry Weisselberg have been accused of wrongdoing, and Allen Weisselberg‘s lawyer declined the Times’ request for comment. Barry Weisselberg declined Air Mail’s request for comment. People who know the Trump Organization CFO have told The Wall Street Journal that he is loyal to the company and were skeptical of the idea of him turning on the ex-president. On the other hand, Weisselberg already has cooperated with prosecutors investigating Trump on two separate occasions—during the 2017 New York attorney general’s investigation of the Donald J. Trump Foundation, which was ultimately forced to shutter, and the 2018 federal probe into hush money payments. While Barbara Res, a former executive vice president at the Trump Organization, told the New York Daily News last month that Weisselberg “thought Trump was a God” and “drank the Kool-Aid,” she added that there are likely limits to his loyalty. “I don’t believe he would commit perjury,” she said.

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