Trump Organization's chief financial officer heads to court as New York state prosecutors close in

Allen Weisselberg, who now faces up to fifteen years in prison, expected to appear before a New York criminal court

By Jon Skolnik

Published September 20, 2021 11:31AM (EDT)

US President-elect Donald Trump along with his son Donald, Jr., arrive for a press conference at Trump Tower in New York, as Allen Weisselberg (C), chief financial officer of The Trump, looks on January 11, 2017. (TIMOTHY A. CLARY/AFP via Getty Images)
US President-elect Donald Trump along with his son Donald, Jr., arrive for a press conference at Trump Tower in New York, as Allen Weisselberg (C), chief financial officer of The Trump, looks on January 11, 2017. (TIMOTHY A. CLARY/AFP via Getty Images)

Trump Organization chief financial officer Allen Weisselberg, as well as a number of the firm's attorneys, is set to appear in a New York state court on Monday.

More than two months after Weisselberg's formal indictment for alleged tax fraud, Monday's appearance marks Weisselberg's first publicly since the charges were brought. It comes on the heels of two state investigations by New York state Attorney General Letitia James and Manhattan District Attorney Cyrus Vance Jr., who have both worked in concert to probe a number of alleged crimes by the Trump Organization, including tax fraud, in Manhattan Criminal Court.

"Beginning from at least 2005 to on or about June 30, 2021, [Weisselberg, the Trump Corporation, Trump Payroll Corp. and ] and others devised and operated a scheme to defraud federal, New York State, and New York City tax authorities," prosecutors wrote, arguing that Weisselberg benefited from an "off-the-books" payment scheme," according to Law & Crime. The scheme allegedly allowed the executive to pay for around $359,058 in tuition expenses for multiple family members, new beds, flat-screen televisions, and more. 

NPR reported that James and Vance are aggressively pursuing the charges. Adam Kaufmann, a former investigations division chief at the Manhattan District Attorney's Office, suggested to NPR that "the district attorney may be considering further charges or defendants."


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Weisselberg, who has already pleaded not guilty to the charges, faces up to 15 years in prison if convicted of grand larceny in the second degree – the prosecutors' most signficant charge, according to The Wall Street Journal. The organization's lawyers have repeatedly called the case politically motivated. One attorney, Alan Futerfas, has further argued that the case should be settled in civil rather than criminal court. 

On Monday, The Wall Street Journal reported that the investigation has also narrowed in on Matthew Calamari, the Trump Organization's chief operating officer. Similar to Weisselberg, Calamari and his son, the firm's chief of security, have both reaped company benefits that may have constituted tax violations, including corporate-sponsored cars and apartments. 

Back in 2019, Trump's former personal attorney, Michael Cohen, testified to Congress that the elder Calamari knew information that would back up claims of Donald Trump deliberately overstating the financial value of his real estate assets – claims that are a part of related civil investigation led by James. 

It is uncertain whether the proceeding against Weisselberg will bear information to warrant a charge against Trump himself. Bloomberg News reported that it's unlikely Weisselberg, 74, will "flip" on Trump because the state is expected to dole out a far lower sentence than the maximum. Other attorneys knowledgeable with the case say that the consequences of turning on Trump might be more severe than the executive's potential prison sentence. 

"It's better for him to take the jail term than suffer the consequences to his bank account if he pleaded guilty," said New York defense lawyer and former federal prosecutor Adam Frisch. 

Weisselberg has worked for the Trump Organization since 1973, starting as a bookkeeper for the former president's father. Trump hired him as CFO, for which he was paid $940,000 a year, around two decades ago.


Jon Skolnik

Jon Skolnik is a staff writer at Salon. His work has appeared in Current Affairs, The Baffler, AlterNet, and The New York Daily News.

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