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  • Writer's pictureThe San Juan Daily Star

Trump’s longtime finance chief sentenced to 5 months in jail

Allen Weisselberg, center, the former CFO of the Trump Organization, leaves State Supreme Court in Manhattan on Thursday, Aug. 18, 2022. Weisselberg, who was once one of Donald Trump’s most loyal lieutenants, served the family company for decades but agreed to testify about its tax fraud in exchange for a lighter punishment.


Allen Weisselberg, once one of Donald Trump’s most loyal lieutenants, was sentenced earlier this week to five months at the Rikers Island jail complex for his role in a tax fraud scheme that led to the conviction of the Trump Organization last year.

A state court judge handed down the sentence after Weisselberg, 75, who worked for the Trump family for the past half-century, testified as the prosecution’s star witness at the trial of the company. Weisselberg, its former chief financial officer, had been facing years in prison. Under a plea deal, he agreed to testify in exchange for a punishment that, with good behavior, might last no more than 100 days.

Still, Weisselberg’s lawyer, Nicholas A. Gravante Jr., pleaded with the judge in state Supreme Court in Manhattan on Tuesday to impose a lighter sentence, citing his client’s military service, lack of a criminal record and the many hours he had spent with prosecutors from the Manhattan district attorney’s office preparing for the testimony.

“Each month makes a big difference when you’re 75 years old,” Gravante said.

But the judge, Juan Merchan, rejected the defense’s request and said that had he not promised the sentence of five months in August, the evidence at trial would have prompted him to impose a significantly longer sentence. “The entire case was driven by greed,” Merchan said.

Weisselberg initially will be assigned to the North Infirmary Command, a jail on Rikers Island that houses people with serious medical conditions as well as a portion of the general population.

Once the hearing concluded, Weisselberg, wearing an olive North Face jacket and dark sneakers, hugged Gravante and was placed in handcuffs by court officers and taken into custody. The district attorney, Alvin Bragg, was in the courtroom for the sentencing, sitting near the back with a sober expression on his face.

“In Manhattan, you have to play by the rules no matter who you are or who you work for,” Bragg said in a statement. Noting the company’s conviction at trial, he added, “These consequential felony convictions put on full display the inner workings of former President Trump’s companies and its CFO’s actions.”

The sentencing punctuated a precipitous fall for Weisselberg, who like other Trump insiders before him, had his misdeeds placed under a microscope and ultimately lost his freedom, collateral damage from a wider investigation into Trump himself. Michael Cohen, Trump’s onetime fixer, served time in federal prison, as did the former president’s campaign chair, underscoring the perils of associating with Trump, whose campaign, presidency and family business have been magnets for law enforcement scrutiny.

As an older man with frail health, Weisselberg faces particularly stark consequences: He will serve time at a notorious jail complex where more than a dozen people died last year, with no promise that the district attorney will forgo additional charges against him.

His ties to the Trumps are also becoming tenuous. After a decadeslong entanglement with Weisselberg, who got his start as a bookkeeper for Trump’s father in the 1970s, the Trump Organization has parted ways with him as of Tuesday, according to people with knowledge of the matter.

He has been on paid leave and recently received his annual bonus from the company for last year, one of the people said. He is expected to receive a broader severance package as well.

The company has good reason not to alienate Weisselberg. While his testimony helped convict the Trump Organization, a cardinal sin for the family and those close to it, he has refused to turn on Trump to assist Bragg’s broader investigation into the former president.

Weisselberg, who initially held the title of controller and eventually became chief financial officer, also logged decades of service in which he created the Trump Organization’s accounting department and helped bring the company back from the brink of bankruptcy. And as the district attorney’s inquiry remains active, with prosecutors interested in Weisselberg’s help as they investigate Trump for his role in hush-money payments made to a porn star during his 2016 presidential campaign, it would be risky to cast him aside.

After the sentencing, Gravante said on the courthouse steps that Weisselberg “deeply regrets the lapse in judgment that resulted in his conviction, and he regrets it most because of the pain it has caused his loving wife, his sons and wonderful grandchildren,” adding that he “also regrets the harm his actions have caused to the Trump Organization and members of the Trump family.”

Weisselberg, Gravante said, “is grateful to them for their continued support throughout this difficult chapter of his life.”

As part of Weisselberg’s plea deal — which required him to plead guilty to scheming to defraud, grand larceny, conspiracy and tax fraud — he already paid New York authorities more than $2 million in taxes, penalties and interest that he owed after reaping lavish off-the-books perks from Trump and his company. Those perks, which were at the center of the prosecution’s case, included leased Mercedes-Benzes, an apartment on Manhattan’s Upper West Side and private school tuition for his grandchildren.

The company, which was convicted on all 17 counts of tax fraud and other financial crimes, will be sentenced Friday. It faces up to $1.6 million in penalties.

As it investigated Trump’s business practices, the Manhattan district attorney’s office initially took aim at Weisselberg in early 2021, seeing him as the potential linchpin in a case against the former president.

He was indicted in the tax scheme case that summer after refusing to cooperate. But his stint in Rikers may not alleviate the pressure he faces from the office. Prosecutors are considering a new round of charges against the executive, people with knowledge of the matter told The New York Times last year.

The charges concern potential insurance fraud, and prosecutors hope that, in combination with his time in Rikers, that threat could persuade Weisselberg to finally turn against Trump, people with knowledge of the matter have said.

Prosecutors made no mention of that inquiry Tuesday but credited the former executive for having testified truthfully against the company.

“Mr. Weisselberg provided significant testimony about his culpability, about how the long-running tax scheme was conducted,” said Susan Hoffinger, the lead prosecutor on the case.

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