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Allen Weisselberg, former Trump Organization CFO, sentenced to 5 months in jail

Allen Weisselberg, the former chief financial officer of the Trump Organization and Donald Trump’s right-hand man for decades, was sentenced to five months in jail for fraud and tax crimes on Tuesday, nearly two months after he testified against the company that employed him for almost half a century.

Weisselberg pleaded guilty in August to 15 counts of fraud and tax evasion after reaching an agreement with Manhattan prosecutors in which he promised to cooperate. In exchange for his testimony, prosecutors agreed to recommend a sentence of five months in New York’s Rikers Island jail, plus five years of probation. Judge Juan Merchan imposed the sentence during a hearing in Manhattan Criminal Court on Tuesday. 

Weisselberg arrived in court wearing a dark green fleece, white undershirt and blue jeans. Susan Hoffinger, an assistant district attorney, told the court that prosecutors “believe that Mr. Weisselberg provided truthful testimony about the underlying facts of his” crimes and “outlined significant benefits to the Trump Corporation and Trump Payroll Corporation.” Hoffinger said Weisselberg had also paid $2 million in back taxes and fines.

Nicholas Gravante, an attorney for Weisselberg, had asked the judge to consider imposing a shorter sentence or confining Weisselberg to house arrest. The charges against Weisselberg could have led to years in prison if he had been convicted at trial.

“He has already been punished tremendously by the disgrace that he brought, not only on himself, but on his wife, his sons and his grandchildren,” Gravante said. “The publicity in this case — which really doesn’t relate to Mr. Weisselberg, it’s his employer — has exponentially increased the severity of the punishment.”

Two Trump Organization companies were convicted on Dec. 6 of a combined 17 counts related to tax fraud. A unanimous jury found that the company used a variety of methods to skirt its payroll taxes by giving executives untaxed bonuses and luxury perks worth millions.

Former Trump Organization Executive Allen Weisselberg Sentenced In New York City
Former Trump Organization CFO Allen Weisselberg arrives for a sentencing hearing at Manhattan Criminal Court on Jan. 10, 2023, in New York City.

Michael M. Santiago/Getty Images

Weisselberg’s three days of testimony in mid-November included detailed explanations of the various schemes, which began in 2005 and lasted until 2018. He described receiving bonus checks for hundreds of thousands of dollars, signed by Trump, but logged as if Weisselberg were an independent contractor. Weisselberg said the funds delivered as independent contractor payments were used to set up Keogh retirement plans, tax-deferred pension accounts designed for people who are self-employed.

Weisselberg and other executives lived rent-free in luxury apartments and drove high-end cars on the company dime. The jury agreed with prosecutors that the valuable digs and luxe benefits represented untaxed compensation.

In a moment that prosecutor Joshua Steinglass would later claim implicated Trump himself, Weisselberg described how Trump and two of his children signed checks to pay up to $100,000 for private school tuition for Weisselberg’s grandchildren. 

Weisselberg said he then instructed the company’s controller to deduct the $100,000 from his salary, allowing him to report a smaller income. Copies of some of the checks signed by the Trumps were shown in court.

Weisselberg said the first time Trump signed a tuition check, Weisselberg told him, “Don’t forget, I’m going to pay you back for this.” The payback, he said, was reducing his salary, and vicariously the company’s payroll liability.

The Trump Organization blamed Weisselberg, arguing that he acted alone. Lawyers for the company said frequently during the trial that “Weisselberg did it for Weisselberg” — a phrase later referred to by a prosecutor as the defense’s “mantra.”

In a statement after its Dec. 6 conviction, the Trump Organization pointed to Weisselberg’s testimony that he’d “betrayed” the company’s trust and “acted ‘solely’ for his ‘own personal gain.'”

“The notion that a company could be held responsible for an employee’s actions, to benefit themselves, on their own personal tax returns is simply preposterous,” the company said.

Trump said on Dec. 6 in a statement that he was “disappointed” and that the company would appeal its conviction.

He accused prosecutors in the heavily Democratic city of targeting him, and using Weisselberg’s crimes as an excuse.

“New York City is a hard place to be ‘Trump,'” said Trump.

Following Tuesday’s hearing, Gravante, Weisselberg’s attorney, told reporters that his client “regrets the harm his actions have caused the Trump Organization and members of the Trump family” and is “grateful to them for their continued support throughout this difficult chapter of his life.”

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