Allen Weisselberg, a longtime executive for Donald Trump 's business empire, was taken into custody Tuesday to begin serving a five-month jail term for dodging taxes on $1.7 million in job perks — a punishment the judge who sentenced him said was probably too lenient for a case "driven entirely by greed."
Weisselberg, 75, was promised the short sentence in August when he agreed to plead guilty to 15 tax crimes and to be a witness against the Trump Organization, where he worked since the mid-1980s. His testimony helped convict the former president's company, where he had served as chief financial officer, of tax fraud.
But when he made the sentence official Tuesday, Judge Juan Manuel Merchan said that after listening to Weisselberg's trial testimony, he regretted that the penalty wasn't tougher. He said he was especially appalled by testimony that Weisselberg gave his wife a $6,000 check for a no-show job so that she could qualify for Social Security benefits.
Had he not already promised to give Weisselberg five months, Merchan said, "I would be imposing a sentence much greater than that."
"I'm not going to deviate from the promise, though I believe a stiffer sentence is warranted, having heard the evidence," he added.
Weisselberg, who came to court dressed for jail rather than in his usual suit, was handcuffed and taken away by court officers moments after the sentence was announced. He was taken to New York City's Rikers Island complex, where he was expected to be housed in an infirmary unit. He will be eligible for release after little more than three months if he behaves behind bars.
Weisselberg's sentencing also marked the end of his career at the Trump Organization, where he had been on leave since the fall, continuing to make $1.14 million in salary and bonuses, even as he was testifying against the company. His lawyer, Nicholas Gravante, said that as of Tuesday, the executive and the company "have amicably parted ways."
As part of the plea agreement, Weisselberg was required to pay nearly $2 million in back taxes, penalties and interest, which prosecutors said he has done. Prosecutors recommended a six-month jail sentence, but Merchan said he settled on five months, in part because of mitigating factors, such as Weisselberg's military service and a stint as a public school teacher. In addition, Merchan ordered Weisselberg to complete five years of probation after he leaves jail.
Gravante had asked the judge for an even lighter sentence than the one in the plea bargain, citing Weisselberg's age and "far from perfect health."
"He has already been punished tremendously by the disgrace that he has brought not only on himself, but his wife, his sons and his grandchildren," Gravante said.
Weisselberg faced the prospect of up to 15 years in prison — the maximum punishment for the top grand larceny charge — if he were to have reneged on his deal or if he didn't testify truthfully at the Trump Organization's trial. Weisselberg is the only person charged in the Manhattan district attorney's three-year investigation of Trump and his business practices.
Weisselberg testified for three days, offering a glimpse into the inner workings of Trump's real estate empire. Weisselberg has worked for Trump's family for nearly 50 years, starting as an accountant for his developer father, Fred Trump, in 1973. He joined Donald Trump in 1986 and helped expand the company into a global golf and hotel brand.
A Manhattan jury convicted the Trump Organization in December, finding that Weisselberg had been a "high managerial" agent entrusted to act on behalf of the company and its various entities.
Weisselberg's arrangement reduced his own personal income taxes but also saved the company money because it didn't have to pay him more to cover the cost of the perks.
The Trump Organization is scheduled to be sentenced on Friday and faces a fine of up to $1.6 million.
