Allen Weisselberg, a longtime executive for Donald Trump and the star prosecution witness in the criminal trial of the former president's real estate company, was sentenced on Tuesday to five months behind bars for helping engineer a wide-ranging tax fraud at the Trump Organization.
Weisselberg, 75, was expected to be sent to New York's notorious Rikers Island jail after pleading guilty last August to all 15 counts he faced in an agreement with prosecutors. The Trump Organization's former chief financial officer admitted that from 2005 to 2017 he and other executives received bonuses and perks that fraudulently saved the company and themselves money.
Weisselberg admitted to evading taxes on $1.76 million of income. He has paid about $2 million in taxes, penalties and interest as part of his punishment.
The Trump Organization was convicted last month on all counts it faced at a trial overseen by Justice Juan Merchan in a New York state court in Manhattan.
In sentencing Weisselberg, Merchan said that had the executive not agreed to the five-month term last August in his plea deal, the judge would have imposed a much longer sentence based on the trial testimony.
Merchan singled out Weisselberg for putting his wife on Trump's payroll so she could receive undeserved Social Security benefits. Other perks for the Weisselbergs included a luxury Manhattan apartment and multiple Mercedes-Benz vehicles.
"The reason the court finds it so offensive is it was driven by greed," despite Weisselberg's already "earning over seven figures," Merchan said.
Though no longer CFO, Weisselberg remains on paid leave from the Trump Organization. Merchan is set to sentence the company on Friday, though penalties are limited to $1.6 million.
Weisselberg wore an olive green North Face jacket and a blue mask at his sentencing. Once at Rikers, he would likely be given a uniform and sneakers with Velcro straps.
He will likely serve 100 days in jail with time off for good behavior. Those days probably will not be easy. Lying between the New York City boroughs of Queens and the Bronx, Rikers is known for violence, drugs and corruption.
The jail houses more than 5,900 inmates, and 19 inmates died there last year. The city's corrections department has said its mission includes keeping inmates safe. Rikers is scheduled to close in 2027.
"You're going into a byzantine black hole," said Craig Rothfeld, a prison consultant helping Weisselberg prepare for lockup.
Rothfeld spent more than five weeks at Rikers in 2015 and 2016 as part of an 18-month sentence for defrauding investors and tax authorities at a company he once led.
He now runs Inside Outside Ltd, which advises people facing incarceration. Another client is Harvey Weinstein, the former Hollywood movie producer convicted twice of rape.
Rothfeld said he hopes Weisselberg will be segregated from the general population, and not placed in a dorm with inmates who may not know him but will know his boss, who is seeking the presidency in 2024.
"Certainly Mr. Weisselberg's 50-year relationship with the former president is on all our minds," Rothfeld said.
Weisselberg testified that Trump signed bonus and tuition checks, and other documents at the heart of prosecutors' case, but was not in on the tax fraud scheme. He also testified that he hoped to get a $500,000 bonus this month, and that the company is paying his lawyers.
Trump was not charged and has denied wrongdoing.
Manhattan District Attorney Alvin Bragg, whose office prosecuted Weisselberg and the Trump Organization, attended the sentencing. Bragg's office is still investigating Trump's business practices.
"In Manhattan, you have to play by the rules no matter who you are or who you work for," Bragg said in a statement.
Weisselberg remains a defendant in New York state Attorney General Letitia James' $250 million civil lawsuit that accused Trump and his company of inflating asset values and Trump's net worth.
