Allen Weisselberg, one of former President Donald Trump's most trusted and loyal employees, was escorted out of court in handcuffs Tuesday after being sentenced to five months in jail for evading more than $1.7 million in taxes on unreported income in the form of company-provided perks that included the rent on his Manhattan apartment, the leases on cars for himself and his wife and tuition for his grandchildren.
Weisselberg, 75, was sentenced to five months on Rikers Island, New York City's notorious jail complex, followed by five years' probation, after he pleaded guilty in August to orchestrating a 15-year tax scheme while working at the Trump Organization as chief financial officer.
He appeared for his sentencing dressed casually in blue pants, a white T-shirt and an olive green fleece jacket.
"He is obviously dressed the way he is dressed because he expects to be remanded today," defense attorney Nicholas Gravante told the judge.
As part of a plea deal, Weisselberg testified over three days in November against the Trump Organization at its criminal trial, which resulted in a conviction against the company for paying the personal expenses of some executives without reporting them as income, and for compensating them as independent contractors instead of full-time employees.
He was promised a sentence of five months in jail and five years' probation in exchange for his testimony, and agreed to repay nearly $2 million in taxes owed.
"The People believe that Mr. Weisselberg provided truthful testimony about the underlying facts of his allocution and plea," a prosecutor, Susan Hoffinger, said.
Weisselberg walked a fine line during his testimony in the Trump Organization trial. He conceded he evaded $1.7 million in taxes by taking part of his compensation in off-the-books luxuries like rent, car leases and private school tuition. He also said the scheme benefitted two entities of the Trump Organization -- Trump Corporation and Trump Payroll Corporation -- by causing them to have a lower payroll tax burden. However, he said nothing to implicate Trump himself in the scheme.
Weisselbarg "knew and thought in his mind that there were benefits to the companies," Hoffinger told the judge.
Though the plea agreement called for a predetermined five-month jail term, Gravante asked for an additional reduction, citing Weisselberg's lack of criminal history, his military service, his full acceptance of responsibility and, the attorney said, the lack of danger he posed to the community.
"Each month makes a big difference when you're 75 years old, because each week you're incarcerated represents a larger percentage of his life," Gravante said.
"I think the words expressed by Mr. Gravante express my thoughts and my feelings," Weisselberg said.
The judge declined, saying an even stiffer sentence would be appropriate for conduct "driven by greed."
"I would be imposing a sentence much greater than that," Judge Juan Merchan said, citing evidence in the trial of the Trump Organization that Weisselberg arranged a $6,000 payment for his wife so she could later claim Social Security benefits.
"At a time when so many Americans work so hard in the hope they might one day benefit from their contributions to Social Security, your client found a way to get his wife a $6,000 payroll payment so she could one day receive the benefits to which she was not entitled," Merchan said.
Weisselberg, while no longer the Trump Organization's chief financial officer, remained employed with Trump's family real estate firm and expected to make more than $1 million last year in salary and bonuses, according to his testimony at trial.
He pleaded guilty in August to one count of grand larceny in the second degree; three counts of criminal tax fraud in the third degree; one count of scheme to defraud in the first degree; one count of conspiracy in the fourth degree; one count of criminal tax fraud in the fourth degree; four counts of offering a false instrument for filing in the first degree; and four counts of falsifying business records in the first degree.
"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 at the time of his guilty plea. "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."
Weisselberg testified at the trial of the Trump Organization that he reduced his reported salary by the total amount of personal expenses paid and that the company benefitted by paying less in payroll taxes. He also testified his primary motive was greed.
As part of this testimony, he told a story about sitting with Trump in his office on the 26th floor of Trump Tower one day in 2012 when Donald Trump Jr. walked in with checks for his father to sign to cover tuition payments for Don Jr.'s children.
Trump looked over at Weisselberg with a chuckle and said, "I might as well pay for your grandkids too," according to Weisselberg's testimony.
Trump then began paying $100,000 a year for Weisselberg's two grandchildren to attend Columbia Grammar School. Weisselberg did not declare it as income and never paid taxes on it, he testified.
Trump, who was not a defendant in the case against the Trump Organization, denied any wrongdoing and called the case "a continuation of the Greatest Political Witch Hunt in the History of our Country."