Weisselberg, a Trump executive, gets ready to go to jail on Rikers Island.

Reuters, NEW YORK, January 10 – An executive who worked for Donald Trump for many years was convicted on Tuesday for helping to plan a 15-year tax fraud scheme at the former president’s real estate company. He is likely to be sent to New York’s notorious Rikers Island jail.

Former CFO of the Trump Organization Allen Weisselberg entered a guilty plea in August and acknowledged that from 2005 to 2017 he and other executives got bonuses and benefits that helped the business and themselves save money.

Following the payment of about $2 million in taxes, fines, and interest as well as his testimony at the criminal trial of the Trump Organization, which was found guilty on all counts, Weisselberg is anticipated to get a term of five months in prison.

Justice Juan Merchan, who presided over the trial in a New York state court in Manhattan, will impose the punishment. Weisselberg most likely would receive a 100-day sentence with credit for good behaviour.

Weisselberg, 75, would likely have a difficult time during those days at a prison infamous for its violence, narcotics, and corruption. Last year, 19 prisoners there passed away.

You’re entering a byzantine black hole, said Craig Rothfeld, a jail expert who is assisting Weisselberg with preparations for detention.


Rikers Island, which is home to more than 5,900 prisoners and is located between the boroughs of Queens and the Bronx in New York City, is where many criminals sentenced to one year or less in prison go.

As part of an 18-month term for cheating investors and tax authorities while serving as the CEO of the now-defunct WJB Capital Group Inc., Rothfeld spent more than five weeks in Rikers in 2015 and 2016.

His current business, Inside Outside Ltd, counsels those who face incarceration. Harvey Weinstein, the former Hollywood film mogul who was twice found guilty of rape, is another client.

Weisselberg will probably be sent to Rikers after being given his sentence, where he will exchange his street clothing for a uniform and a pair of velcro-fastened sneakers.

Weisselberg is running for president in 2024, therefore Rothfeld said he hopes he will be kept apart from the general population and not housed in a dorm with other prisoners who may not know him but will.

All of us are thinking about Mr. Weisselberg’s 50-year friendship with the former president, Rothfeld added.

To “provide a safe and supportive environment for everyone who enters our custody,” according to a representative for the city’s Department of Correction.

The closure of Rikers is slated for 2027.


The main government witness used against his employer was Weisselberg.

He said before the jury that Trump signed other crucial documents, including tuition and bonus checks, but was not involved in the tax fraud plan.

Weisselberg is still on paid leave from the Trump Organization despite no longer serving as CFO. He expressed hope for a $500,000 bonus in testimony from November.

Weisselberg claimed in court that the business is paying his attorneys. Rothfeld is also being paid, according to a source with knowledge of the situation. Rothfeld opted not to respond.

Trump has said he did nothing wrong and was not charged. His business practises are currently under investigation by the Manhattan District Attorney’s office.

On Friday, Merchan will also impose a penalty on the Trump Organization. The maximum fine is $1.6 million.

Weisselberg is still included as a defendant in the $250 million civil action brought by New York Attorney General Letitia James, who claims that Trump and his business overstated asset prices and Trump’s net wealth.

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