Allen Weisselberg, former Trump Organization CFO, faces sentencing Tuesday

Allen Weisselberg, the former chief financial officer of the Trump Organization and Donald Trump’s right-hand man for decades, is expected to be sentenced to jail for fraud Tuesday afternoon.

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 testify against the company that employed him for nearly half a century. 

In exchange for Weisselberg’s testimony, prosecutors agreed to recommend a sentence of five months in New York’s Rikers Island jail, followed by five years’ probation. He must also pay $1.9 million in back taxes and fines. The charges against Weisselberg could have led to years in prison if he had been convicted at trial.

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.

Weisselberg’s three days of testimony in mid-November included detailed explanations of the various schemes, which began in 2005. 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.

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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.