© Reuters. FILE PHOTO: Former Trump Organization chief financial officer Allen Weisselberg leaves a courtroom in New York on November 15, 2022. REUTERS/Yuki Iwamura
By Karen Freifield
NEW YORK (Reuters) – A longtime Donald Trump executive is expected to be sent to New York’s notorious Rikers Island prison after being sentenced on Tuesday for helping engineer a 15-year tax fraud scheme at the former president’s real estate company.
Allen Weisselberg, the former chief financial officer of the Trump Organization, pleaded guilty in August, admitting that from 2005 to 2017 he and other executives received bonuses and perks that saved the company and themselves money.
Weisselberg is expected to be sentenced to five months in prison, after paying nearly $2 million in taxes, penalties, interest and testimony in the criminal trial of the Trump Organization, which was found guilty on all counts it faced.
The ruling will be imposed by Judge Juan Merchant, who presided over the trial in the New York State District Court in Manhattan. Weisselberg will likely serve 100 days with leave for good behaviour.
Those days probably won’t be easy for Weisselberg, 75, in a prison known for violence, drugs and corruption. Nineteen inmates died there last year.
“You’re walking into a Byzantine black hole,” said Craig Rothfield, a prison counselor who helps Weisselberg prepare for the prison.
50 year relationship
Many New York City convicts facing a year or less behind bars head to Rikers Island, which lies between the New York City boroughs of Queens and the Bronx and holds more than 5,900 inmates.
Rothfeld spent more than five weeks at Rikers in 2015 and 2016 as part of an 18-month prison sentence for defrauding investors and tax authorities when he was CEO of WJB Capital Group Inc.
He now runs Inside Outside Ltd, which advises people facing imprisonment. Another client is Harvey Weinstein, a former Hollywood film producer who was twice convicted of rape.
After his sentencing, Weisselberg will likely be taken to Rikers and trade his street clothes for a uniform and velcro-based sneakers.
Rothfeld said he hopes to separate Weisselberg from the general population, and not put him in a residence with inmates who may not know him but who will know his boss, who is running for president in 2024.
“Certainly Mr. Weisselberg’s 50-year relationship with the former president is very much on our minds,” Rothfeld said.
A spokesperson for the city’s Department of Corrections said the agency’s mission is to “create a safe and supportive environment for everyone who comes into our custody.”
Rikers is scheduled to close in 2027.
Star witness
Weisselberg was the government’s star witness against his employer.
He told jurors that Trump signed bonus and study checks, and other documents at the center of plaintiffs’ case, but that he was not involved in the tax fraud scheme.
Although he is no longer CFO, Weisselberg remains on paid leave from the Trump Organization. He testified last November that he hoped to receive a $500,000 bonus this month.
Weisselberg testified that the firm pays his lawyers. A person familiar with the matter said he also pays Rothfeld. Rothfeld declined to comment.
Trump has not been charged and has denied any wrongdoing. The Manhattan District Attorney’s Office is still investigating his business practices.
Merchan will also judge the Trump Organization on Friday. Fines are limited to $1.6 million.
Weisselberg remains a defendant in New York Attorney General Letitia James’ $250 million civil lawsuit, which alleges Trump and company inflated Trump’s asset values and net worth.
Rothfeld said he advised Weisselberg not to move out of the Rikers because of the danger of violence in the grounds, and not to interfere with conversations between other guests.
“The point is to keep to yourself,” Rothfeld said.