Top Trump Executive Sentenced to Five Months in Tax Fraud Case

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Longtime CFO Allen Weisselberg cooperated with prosecutors in their case against the former president’s businesses.

A Manhattan judge has sentenced longtime Trump Organization chief financial officer Allen Weisselberg to five months in jail for his role in helping the former president’s businesses evade taxes for much of the last decade. Following the sentencing on Tuesday afternoon, Weisselberg, 75, was taken into custody and transported to New York City’s Rikers Island jail to begin serving his time. Weisselberg was also given five years probation and ordered to pay $2 million in restitution. 

Weisselberg could have faced as much as 25 years in state prison based on the initial charges against him, but last summer he pleaded guilty and agreed to testify against his former employer—the Trump Organization. However, he did not agree to testify against his former boss, Trump. Last month a jury found two Trump-owned corporations guilty on nine counts of tax fraud; Trump was not charged personally in the case. The companies will be sentenced later this week, although they have appealed the conviction.

The case centers around a scheme under which Trump’s companies would pay top executives, like Weisselberg, less money in salary, but make up the difference by giving them fancy perks like Mercedes-Benzes, apartments, and even tuition for Weisselberg’s grandchildren. Employees ended up paying lower taxes for the same overall level of take-home compensation. At the trial for the Trump companies, defense attorneys argued that this scheme only benefitted Weisselberg and other executives who received the perks. But prosecutors contended that it actually provided a huge benefit for the Trump Organization, too, because it allowed the companies to boost executives’ pay for about half the cost of a taxable salary increase.

After Weisselberg pleaded guilty to participating in the scheme, Trump kept him on the company payroll—and in fact offered him a large bonus to be paid out following the trial. For much of the run-up to the Trump Organization trial, attorneys on both sides studiously tried to avoid making the case about Trump personally. But almost immediately upon the start of the trial, defense attorneys began referencing Trump—specifically praising him for being generous to Weisselberg even after his guilty plea. This gave prosecutors an opportunity to go after Trump, and they painted a picture of the Trump Organization as a workplace subsumed by a “culture of fraud.”

At one point, prosecutors showed jurors paperwork signed by Trump indicating that he had approved of a request by one employee to reduce that employee’s salary by $75,000—the exact amount of rent the employee would have owed for a Trump-owned apartment he was living in rent-free. 

“Mr. Trump explicitly sanctioning tax fraud! That’s what this document shows!” Manhattan assistant district attorney Joshua Steinglass told the jury.

On Tuesday, as expected, prosecutors endorsed the five-month jail sentence they had negotiated with Weisselberg in exchange for his helpful testimony. Following the formal sentencing by New York judge Juan Merchan, Weisselberg was handcuffed and led away. 

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