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Ex-Trump Organization CFO Allen Weisselberg Gets Five Months Behind Bars, as Judge Bemoans Sentence Couldn’t Have Been ‘Much Greater’

Allen Weisselberg sentencing

Trump Organization’s former Chief Financial Officer Allen Weisselberg arrives to court, Tuesday, Jan. 10, 2023, in New York. (AP Photo/John Minchillo)

Allen Weisselberg, the former chief financial officer of the Trump Organization, will be trading his office in the glitzy Trump Tower for a cell in one of the most scandal-beset prisons in the country after pleading guilty to a series of financial crimes in connection with his work for the former president’s real estate empire.

New York Judge Juan Manuel Merchan on Tuesday sentenced the 75-year-old Weisselberg to five months in prison to be served at Rikers Island immediately. He appeared to dress for that outcome, skipping his usual business suit in favor of a North Face fleece and navy sweatpants.

The judge said that Weisselberg’s testimony at the Trump Organization criminal trial, over which he also presided, gave him pause about the lenient prison sentence he had agreed to hand down in the current case.

“Were it not because I made that promise, I would not be imposing a five-month sentence. I would be imposing a much greater sentence,” Merchan said in court. “Most significantly was the $6,000 payroll payment to Mr. Weisselberg’s wife and the reason I find that so offensive is that it was driven purely by greed.”

Merchan explained how Weisselberg was “earning upwards of seven figures” and clearly “did not need that money.” However, he still “found a way” to make sure that his wife received sufficient payroll income so she could “one day benefit from social security payments she was not entitled to.”

The sentence was previously agreed to by Weisselberg and prosecutors in the Manhattan District Attorney’s Office in exchange for the longtime Trump executive pleading guilty to 15 separate criminal charges and testifying against the Trump Organization and Trump Payroll Corp, which were convicted last month on more than a dozen felony charges.

In addition to the time in prison, Judge Merchan also sentenced Weisselberg to five years of post-release probation and ordered him to make full repayment of taxes, penalties, and interest due to New York City and New York State tax authorities totaling $1,994,321.

With good behavior, Weisselberg may be eligible for release from detention in just over three months.

Prior to the Judge Merchan passing the sentence, Weisselberg’s attorney, Nicholas Gravante Jr., asked the court to further reduce his client’s time behind bars, requesting that Weisselberg be permitted to serve the second half of his prison term under house arrest.

“Aside from fact that he’s 75 years old, Mr. Weisselberg has no criminal history. He does have history of military service and has fully accepted responsibility for actions in this case, poses no danger to community, and has already been punished severely,” Gravante said, adding that what his client has had to endured was “unique for this particular case.”

“The publicity in this case has exponentially increased the severity of punishment that he has had to suffer,” Weisselberg’s attorney told the court.

He then spoke about how Weisselberg’s grandchildren “saw their grandfather being led into court” earlier that morning, and said the shame his crimes brought upon his family “causes him more pain than anything else that’s been imposed on him.”

The only individual currently charged in the Manhattan District Attorney Alvin Bragg’s investigation into the company’s roughly 13-year tax fraud scheme, Weisselberg in August pleaded guilty to one count of second-degree grand larceny, three counts of third-degree criminal tax fraud, one count of first-degree scheme to defraud, one count of fourth-degree conspiracy, one count of fourth-degree criminal tax fraud, four counts of first-degree offering a false instrument for filing, and four counts of first-degree falsifying business records.

In a statement, Bragg described the outcome as evidence that: “In Manhattan, you have to play by the rules no matter who you are or who you work for.”

“Trump Organization Chief Financial Officer Allen Weisselberg used his high-level position to secure lavish work perks such as a rent-free luxury Manhattan apartment, multiple Mercedes Benz automobiles and private school tuition for his grandchildren – all without paying required taxes,” Bragg wrote. “Weisselberg admitted to all counts of the indictment against him and testified in open court that for well over a decade, he carried out a fraudulent tax scheme together with others at the Trump Organization that not only enriched himself and his lifestyle by evading taxes and accountability, but also had benefits for the companies. Now, he and two Trump companies have been convicted of felonies and Weisselberg will serve a jail sentence for his crimes. These consequential felony convictions put on full display the inner workings of former President Trump’s companies and its CFO’s actions.”

The Trump Organization faces sentencing on Wednesday, but former President Donald Trump himself does not currently face any criminal charges. Nearly a year ago, two of Bragg’s former top prosecutors resigned, claiming that the current top prosecutor in Manhattan pressed the brakes when it came to charging the former president. Bragg insists that the investigation continues.

Due in large part to Weisselberg’s testimony, the Trump Organization and Trump Payroll Corp. were convicted on all 17 felony counts charged in the indictment. Both companies were convicted of one count of scheme to defraud in the first degree, a count of conspiracy in the fourth degree, two counts of criminal tax fraud in the third degree, a count of criminal tax fraud in the fourth degree, and three counts of falsifying business records in the first degree.

In addition, the Trump Organization was convicted of a separate count of falsifying business records in the first degree.

Prosecutors called Weisselberg the primary beneficiary of the tax fraud scheme, saying he received approximately $1.76 million in unreported compensation. Some of his perks included rent on a luxury Manhattan apartment, utilities, parking garage expenses, Mercedes Benz cars for himself and his wife, home furnishings, cash for personal holiday tips, and payment of his grandchildren’s private school tuition.

During the Trump Organization trial, Weisselberg’s testimony included a claim that Donald Trump himself played in a role in the fraud scheme, and prosecutors said that Trump knew about it during closing arguments, according to accounts from the trial.

Trump, who was not indicted in connection with the scheme, has repeatedly denied any wrongdoing and described the prosecution of Weisselberg as politically-motivated.

(Photo by Michael M. Santiago/Getty Images)

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Jerry Lambe is a journalist at Law&Crime. He is a graduate of Georgetown University and New York Law School and previously worked in financial securities compliance and Civil Rights employment law.