Evan Vucci/AP
- Ex-CFO Allen Weisselberg, 75, was convicted of rampant payroll tax fraud at Trump’s company.
- A judge will likely order he immediately begin serving 5 months in NYC’s notorious Rikers Island.
- Weisselberg’s jail coach says he is ‘prepared to do his time honorably and quietly.’
Allen Weisselberg, Donald Trump’s top money man for decades, is braced to begin serving an expected five-month tax-fraud sentence on Tuesday at New York City’s notorious Rikers Island complex, his jail coach told Insider.
Weisselberg, 75, is the lone executive going to jail in the Manhattan District Attorney’s Office’s prosecution of a decade-long tax-fraud scheme at the Trump Organization, the former president’s real-estate and golf-resort company.
“He understands he will be taken into custody by the Department of Correction immediately” upon sentencing, said Craig Rothfeld, a prison consultant Weisselberg hired to advise him on his upcoming sentence.
Trump’s former finance chief will walk into the courtroom a free man, but be escorted out in handcuffs, Rothfeld said.
And while he is more accustomed to the Mercedes luxury vehicles the Trump Organization once provided him, Weisselberg will then step into a New York City Department of Correction van or bus for the trip to Rikers.
Rikers is notorious for understaffing, unsanitary conditions, and violence, which have been long documented by journalists; 19 detainees died in custody there last year, many by suicide or suspected overdoses, according to Gothamist.
Weisselberg will stay in his business suit for the trip, Rothfeld said.
Once at Rikers’ admissions facility, the Eric M. Taylor Center, he will be issued the jail’s standard “uniform” of tan pants and a white T-shirt or sweatshirt, and his suit and tie will be vouchered and stowed by staff, Rothfeld said.
“Mr. Weisselberg is prepared to do his time honorably, quietly and without incident so that he may return to his family and loved ones as soon as possible,” Rothfeld said.
Rothfeld, of Inside Outside Ltd., is also a prison consultant for Harvey Weinstein. He has helped the disgraced Hollywood producer navigate New York’s prison system since he was sentenced in 2020 to 23 years for the rape and sexual assault of two women.
Rothfeld declined to describe specifics of Weisselberg’s preparation for what is expected to be a term of 100 days behind bars. Under city law, inmates get a third off their sentences for good behavior.
Himself a veteran of Rikers, Rothfeld did say this — it won’t be easy.
“Rikers is already hard on a 20-year-old,” he said. “Generally speaking, someone in their ’70s will have added challenges.”
A board containing confiscated shanks from Rikers Island is displayed during a press conference with Mayor Eric Adams on Rikers Island on June 22, 2022.
Shawn Inglima/New York Daily News for Getty Images
Weisselberg is hoping to be assigned to an individual cell or to protective custody, Rothfeld said.
“Even if he wasn’t the former CFO and a dear friend of the former president for five decades, everyone who is 75 years old needs to be looked at differently, whether you’re Allen Weisselberg or not,” Rothfeld added.
He’s hoping not to be assigned to one of Rikers’ open dorm rooms, where up to 60 detainees are housed under the supervision of a single correction officer.
The doorms have “20 beds down the left wall, 20 down the right wall and 20 down the middle,” the jail coach explained.
“The majority of people in these dorms are people held without bail due to the violent nature of their crimes,” he said.
“You have competing gang factions, ethnic and racial conflict. It’s a fuse box waiting to go off. And the Department of Correction needs more staffing. It’s not their fault.”
Weisselberg’s jail housing will not be assigned until after his admission.
“The health and safety of our staff and every individual in our custody is paramount to us,” said James Boyd, deputy commissioner for public information for the city Department of Correction.
“Every individual who enters DOC’s custody is housed in accordance with our policies. It is our agency’s mission to create a safe and supportive environment for everyone who enters our custody. “
The Rikers Island jail complex in New York City, with the Manhattan skyline in the background.
Seth Wenig/AP
Weisselberg admitted to running a decade-long payroll tax scam as the CFO of Trump Organization, saving himself $900,000 in taxes and hundreds of thousands of dollars more for fellow second-tier executives at the company.
He was promised a five-month sentence as part of an August plea deal. The deal required he pay $2 million in back taxes and penalties and that he testify truthfully against the company at trial.
In November, Weisselberg took the stand against his company in the same courtroom where he’ll be sentenced after lunch on Tuesday.
Whether he testified truthfully remains open to debate.
Manhattan prosecutors said during closing arguments that Weisselberg “shaded the truth” when he told the jury that he had zero intention of helping the company.
It appears that jurors, too, did not believe that “zero intention” portion of Weisselberg’s testimony — otherwise, they legally could not have convicted him, former Manhattan prosecutors told Insider last month.
New York Supreme Court Justice Juan Merchan has warned that he could impose a higher sentence than five months if he finds Weisselberg failed to testify truthfully.
Weisselberg’s lawyer, Nicholas Gravante, Jr., declined to comment; he has maintained that Weisselberg did testify truthfully.
Prosecutors, too, have declined to say if they will ask for more time, but the office has noted that Weisselberg’s indictment, guilty plea, and truthful description of the payroll tax scheme were crucial to last month’s 17-count Trump Organization conviction.
The Trump Organization now faces up to $1.6 million in fines; Merchan is scheduled to set the amount at a January 13 sentencing.
