PRISON STRIPES: Former Trump Organization CFO headed to New York’s most infamous lock-up
Former Trump Organization Chief Financial Officer Allen Weisselberg has been sentenced to five months in jail for his role in helping his boss — Donald Trump — circumvent the IRS and evade tax laws.
The 75-year-old ex-financial executive is expected to serve his time at New York’s infamous Rikers Island.
Prison consultant, Craig Rothfeld, has been preparing the convicted felon for his time in incarceration.
“You’re going into a byzantine black hole,” Rothfeld said, according to Reuters.
Rothfeld spent time in Rikers himself in 2015 and 2016 after being given an 18-month sentence for defrauding investors of the company he once helmed.
“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,” Reuters reported.
Between 2005 and 2017, Weisselberg received off-the-books compensation from the Trump Organization – including a luxury NYC apartment and private school tuition for relatives.
The former CFO pleaded guilty in August 2022 and paid over $2 million in restitution, penalties, and fines for his complicity.
After serving three generations of Trumps, Weisselberg leaves a less-than-spectacular legacy behind.
Justice Juan Merchan, who oversaw the company’s criminal trial, handed down the sentence for Manhattan District Attorney Alvin Bragg’s star witness.
Though no longer CFO, the longtime loyal Trump executive is still on the former President’s namesake company’s payroll – and testified in November that he hoped to receive a bonus of half a million dollars this month.
Weisselberg’s employer, the Trump Organization, is reportedly paying his legal fees.
Rikers Island is currently home to nearly 6,000 prisoners – many with sentences of less than a year. Known to be a bed of corruption, crime, and drugs, the notorious New York jail is slated to close in 2027.
In December, the Trump Organization was found guilty of all charges brought by the Manhattan DA’s office – including criminal tax fraud.
Bragg attended Weisselberg’s sentencing and is keeping the door open for more charges.
Despite what some consider to be a light sentence for 15 felony convictions and over a decade of financial misdeeds and manipulation – Weisselberg is nowhere near in the clear as a defendant in New York Attorney General Letitia James’ $250 million civil suit against the Trump Organization.
Rothfeld has advised the soon-to-be inmate against mingling with the general population and talking to other inmates.
“The goal is to keep to yourself,” Rothfeld said.
Justice Merchan will be handing down the Trump Organization’s sentence on Friday.
Check back in with Occupy Democrats for the details on that much-anticipated event.
Original reporting by Karen Freifeld at Reuters.
Follow Ty Ross on Twitter @cooltxchick
