Trump CEO Weiselberg Prepares for Rikers Island Jail

NEW YORK, Jan 10 (Reuters) – A longtime Donald Trump executive is expected to be sent to New York’s notorious Rikers Island prison after being convicted on Tuesday of helping engineer a 15-year tax fraud scheme at the real estate of the former president.

Alan Weiselberg, the Trump Organization’s former chief financial officer, 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.

Weiselberg is expected to be sentenced to five months behind bars after paying nearly $2 million in taxes, penalties and interest and testifying in the criminal trial against the Trump Organization, which was convicted on all charges it faced.

The sentence will be imposed by Judge Juan Murchan, who oversaw the trial in New York State Court in Manhattan. Weiselberg will likely serve 100 days with time off for good behavior.

These days probably won’t be easy for Weiselberg, 75, in a prison known for violence, drugs and corruption. Nineteen inmates died there last year.

“You’re going into a Byzantine black hole,” said Craig Rothfeld, a prison consultant who is helping Weiselberg prepare for the arrest.


Many New York inmates facing a year or less behind bars head to Rikers Island, which is located between the New York boroughs of Queens and the Bronx and houses more than 5,900 inmates.

Rothfeld spent more than five weeks in Rikers in 2015 and 2016 as part of an 18-month sentence for defrauding investors and tax authorities when he was CEO of the now-defunct WJB Capital Group Inc.

He now runs Inside Outside Ltd, which advises people facing imprisonment. Another client is Harvey Weinstein, the former Hollywood film producer convicted twice of rape.

After he’s sentenced, Weisselberg will likely be taken to Rikers and trade his street clothes for a uniform and sneakers with Velcro straps.

Rothfeld said he hopes Weiselberg will be separated from the general population and not housed in a dormitory with inmates who may not know him but will know his boss, who is running for president in 2024.

“Certainly Mr. Weiselberg’s 50-year relationship with the former president is on all of our minds,” Rothfeld said.

A spokesman for the city’s Department of Corrections said the agency’s mission is “to create a safe and supportive environment for everyone who enters our detention center.”

Rikers is scheduled to close in 2027.


Weiselberg was the government’s main witness against his employer.

He told jurors that Trump signed bonus and training checks and other documents at the heart of prosecutors’ case, but 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 in November that he hoped to receive a $500,000 bonus this month.

Weiselberg testified that the company is paying his lawyers. It also pays Rothfeld, a person familiar with the matter said. Rothfeld declined to comment.

Trump has not been charged and denies wrongdoing. The Manhattan District Attorney’s Office is still investigating his business practices.

Murchan will also denounce the Trump Organization on Friday. Penalties are capped at $1.6 million.

Weissberg remains a defendant in New York Attorney General Letitia James’ $250 million civil suit alleging that Trump and his company inflated the value of Trump’s assets and net worth.

Rothfeld said he advised Weiselberg not to go outside at Rikers because of the risk of violence in the yards and not to interfere in conversations between other inmates.

“The goal is to keep to yourself,” Rothfeld said.

Reporting by Karen Freifeld; Editing by Richard Chang

Our standards: Thomson Reuters Trust Principles.

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