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

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

Allen Weisselberg Appears In Court For Tax Fraud Charges - Credit: Curtis Means/pool/Getty Images

Allen Weisselberg Appears In Court For Tax Fraud Charges – Credit: Curtis Means/pool/Getty Images

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.

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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.)

“Today Allen Weisselberg admitted in Court that he used his position at the Trump Organization to bilk taxpayers and enrich himself,” Manhattan District Attorney Alvin Bragg said in a statement after the plea proceeding. “Instead of paying his fair share like everyone else, Weisselberg had the Trump Organization provide him with a rent-free apartment, expensive cars, private school tuition for his grandchildren and new furniture – all without paying required taxes.”

“This plea agreement directly implicates the Trump Organization in a wide range of criminal activity and requires Weisselberg to provide invaluable testimony in the upcoming trial against the corporation,” Bragg also said. “Furthermore, thanks to the incredibly hard work and dedication of the team prosecuting this case, Weisselberg will spend time behind bars. We look forward to proving our case in court against the Trump Organization.”

Rolling Stone 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 Rolling Stone 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 Rolling Stone’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 Rolling Stone 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.

As he left the Downtown Manhattan courthouse on Thursday, Weisselberg did not say anything. He walked arm-and-arm with one of his attorneys, Mary E. Mulligan.

“In one of the most difficult decisions of his life, Mr. Weisselberg decided to enter a plea of guilty today to put an end to this case and the years-long legal and personal nightmares it has caused for him and his family,” one of Weisselberg’s attorneys, Nicholas Gravante, Jr., said in a written statement after the plea. “Rather than risk the possibility of 15 years in prison, he has agreed to serve 100 days. We are glad to have this behind him.”

A spokesperson for the Trump Organization issued a statement that praised Weisselberg and framed the proceedings as a politically motivated with hunt against the ex-president.

“Allen Weisselberg, a long time, trusted employee of The Trump Organization, is a fine and honorable man who, for the past 4 years, has been harassed, persecuted and threatened by law enforcement, particularly the Manhattan District Attorney, in their never ending, politically motivated quest to get President Trump.  In the history of our country, no prosecutor has ever brought a criminal case against a person for failing to report a company car, a company apartment or so-called ‘fringe benefits’,” the statement began.  “Yet, the Manhattan D.A. not only seized upon this opportunity, but went so far as to threaten Mr. Weisselberg’s children (who have done nothing wrong) in an attempt to pressure Mr. Weisselberg to say bad things or make up lies about President Trump. Mr. Weisselberg, who just turned 75, in an effort to put this matter behind him and get on with his life, decided that the best course of action—for himself and his family—was to plead guilty.”

The spokesperson insisted on the companies’ innocence. “The two Trump companies that the Manhattan DA has been targeting, however, will not be taking a plea for the simple reason that they have done nothing wrong.  As a result, we now look forward to having our day in court, which, quite interestingly, has been scheduled for October 24 — just days before the mid-term elections.”

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