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The Trump Organization’s Top Money Man Pleads Guilty to Tax Crime ‘Scheme’

Allen Weisselberg, the Trump Organization’s longtime chief finance executive, answered “yes, your honor” on Thursday when a Manhattan judge asked if he “engaged in a scheme” with the Trump Organization “to defraud federal, New York state, and New York City tax authorities,” as he pleaded guilty to the 15-count indictment in his state tax crimes case. 

Weisselberg’s stunning admission appears to directly implicate the Trump Organization and related companies in criminal activity, such as tax fraud and falsifying business records. 

The bespectacled exec, besuited in an inky navy ensemble with a crisp white shirt and sky blue tie, entered the courtroom around 9:30 a.m. One of his attorneys gave him several reassuring pats on the back prior to the proceeding. After Weisselberg entered the well and took his seat at a table, he appeared in good spirits while chatting with his attorneys. Weisselberg’s mood did not appear to sour when proceedings took off.  When Judge Juan Merchan went count-by-count asking Weisselberg whether he engaged in the crimes, Weisselberg’s voice remained steady. 

This proceeding stems from a 2021 indictment from the Manhattan district attorney’s office accusing Weisselberg and several of Trump’s corporations of tax crimes in what prosecutors described as a “sweeping and audacious illegal payment scheme.” The charges stemmed from the extensive benefits Weisselberg enjoyed in his role as Donald Trump’s head money man. (The Trump Organization and several related companies charged in the indictment have maintained their not guilty plea, so the former president’s eponymous business, and a handful of related corporations, remain indicted.) 

Yostrive exclusively reported Wednesday that Weisselberg would admit he conspired with several of Trump’s companies during his plea proceeding. CNN first reported that Weisselberg’s plea deal required him to testify against Trump’s companies at trial. The New York Times earlier this week broke the story that Weisselberg planned to plead guilty. 

One of the two sources who spoke with Yostrive earlier this week about Weisselberg said his possible trial testimony would be the same as what he said in court this morning. This source also said that while Weisselberg is agreeing to testify as part of his plea deal, it does not mean he definitely will. It’s up to prosecutors whether they call him, which presents possible benefits and risks to the office. 

Prosecutors’ statements in court confirmed Yostrive’s reporting. The prosecution said that Weisselberg’s plea deal required him to fully admit, under oath, that he participated in these tax crimes in a “scheme” with Trump’s companies. They also said that a condition of his plea was that he “must testify truthfully” at trial if called. Under his plea deal, Weisselberg must agree to cough up nearly $2 million in unpaid taxes. The plea agreement also states that Weisselberg won’t be sentenced until after the Trump Organization trial concludes “to ensure compliance” with the testimony requirement.  

Weisselberg’s sentence under the plea deal is five months in jail followed by five years probation. If Weisselberg violates the deal, that sweetheart agreement could go out the window. Merchan warned that Weisselberg could face a far longer sentence if he didn’t hold up his end of the deal. 

On the one hand, Weisselberg’s testimony could well implicate Trump’s businesses. If these Trump companies were found guilty, the fines and penalties could deal a potentially ruinous financial blow. 

At the same time, the Trump companies’ attorneys would have an opportunity to cross-examine Weisselberg — and ask him whether his boss was involved in these crimes. This opens up the door for Weisselberg to deny Trump’s involvement in criminal activity. 

One of the sources insisted Weisselberg would not do anything beyond his testimony to aid in prosecutors’ criminal probe against Trump’s businesses. 

This makes sense, considering Weisselberg’s fealty to the Trump family and the resulting perks. Weisselberg, who worked for the Trumps for about 50 years, lived for free in an apartment on Manhattan’s West Side starting in 2005. The Trump Corporation, which was leasing the apartment, paid for his rent on the pad, as well as his parking garage costs and utility fees, the indictment said.

From 2005 to 2017, Trump’s company also allegedly paid the leases on two Mercedes Benzes that Weisselberg and his wife treated as their personal cars. Trump’s business gave cash to Weisselberg around Christmastime, too, so he could dole out “personal holiday gratuities,” prosecutors said. 

Trump’s company footed the bill for Weisselberg’s personal costs “for his homes and for an apartment maintained by one of his children,” as well, the indictment claimed.  Some of these asks included “new beds, flat-screen televisions, the installation of carpeting, and furniture for Weisselberg’s home in Florida.” The Trump Corporation also paid the private school tuition for Weisselberg’s grandkids, prosecutors said. 

Getting plum benefits as a corporate executive isn’t illegal, of course. Prosecutors said that Weisselberg didn’t declare them on his taxes, however, meaning he pocketed $1.7 million in illegal payments.  

Rebecca Roiphe, New York Law School professor, told Yostrive that Weisselberg’s plea does not mean that Trump will wind up in cuffs. If the trial shakes out in the prosecutors’ favor, however, it’s possible Trump’s companies could collapse. 

“Criminal liability is usually a pretty big deal for a corporation— it’s often a death sentence,” Roiphe said earlier this week. “The penalties could be so significant that the organization cannot survive past it. The penalties can be so high the company just doesn’t exist, and it could ultimately end in the dissolution of the company.”

The trial in this case, which will now just be against Trump’s companies, is scheduled for October. Though the chances of Trump himself being charged in New York seem increasingly slim, he faces possible criminal exposure elsewhere in the U.S.  
Federal agents executed a search warrant of Mar-a-Lago less than two weeks ago, in relation to his allegedly keeping classified documents at his sprawling South Florida estate. Meanwhile, a Fulton County, Georgia, grand jury is probing Trump’s alleged attempted election meddling in the 2020 election.

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