NEW YORK -- Allen Weisselberg, a longtime executive for Donald Trump's business empire, was sentenced Tuesday 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 Gravante Jr., pleaded Tuesday with the judge in state Supreme Court in Manhattan to impose a lighter sentence, citing his client's military service, his 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 he regretted that the penalty wasn't tougher. He said he was especially appalled by testimony that Weisselberg gave his wife a $6,000 check for a no-show job so that she could qualify for Social Security benefits.
Had he not already promised to give Weisselberg five months, Merchan said, "I would be imposing a sentence much greater than that."
"I'm not going to deviate from the promise, though I believe a stiffer sentence is warranted, having heard the evidence," he added.
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 was handcuffed by court officers and taken into custody. The district attorney, Alvin Bragg, was in the courtroom for the sentencing.
"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 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 former lawyer, served time in federal prison, as did the former president's campaign chair.
STARK CONSEQUENCES
As an older man in frail health, Weisselberg faces particularly stark consequences: He will serve time at Rikers Island, 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.
The Rikers Island compound of 10 jails on land in the East River, just off the main runway at LaGuardia Airport in Queens, has been plagued in recent years by violence, inmate deaths and staggering staffing shortages.
Though just 5 miles from Trump Tower, it's a world away from the life of luxury Weisselberg had built -- a far cry from the gilded Fifth Avenue offices where he worked and the Hudson River-view apartment where he lived.
The Trump Organization punished him only nominally after his arrest in July 2021, reassigning him to senior adviser and moving his office. He even celebrated his 75th birthday at Trump Tower with cake and colleagues in August, just hours after finalizing the plea agreement that ushered his transformation from loyal executive to prosecution witness and, now, jail inmate.
His ties to the Trumps are also becoming tenuous. After a decades-long 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.
INVESTIGATION CONTINUES
While his testimony helped convict the Trump Organization, 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.
The district attorney's inquiry remains active, with prosecutors interested in Weisselberg's help in their investigation into payments made to a porn star during Trump's 2016 presidential campaign.
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.
Weisselberg's testimony at trial, which spanned three days in November, was crucial for prosecutors, who had argued that the executive had manipulated his pay to avoid his full tax burden and had done so in part to benefit the company.
In one instance, Weisselberg told jurors that, after receiving money from Trump to pay his grandchildren's private school tuition, he had made sure to reimburse the organization.
"The amount of money I was being given was too much, and I thought the right thing to do was pay the company back," Weisselberg said.
Toward the end of the trial, a prosecutor, Joshua Steinglass, compared Weisselberg's motivations with that of a musician.
"A professional musician in an orchestra -- she plays the best she can because she wants to succeed," Steinglass said, adding, "But an ancillary benefit is that it makes the whole orchestra sound better."
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 provide testimony regarding 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.
The Trump Organization is scheduled to be sentenced Friday and faces a fine of up to $1.6 million.
Information for this article was contributed by Ben Protess, Jonah E. Bromwich and William K. Rashbaum of The New York Times and by Michael R. Sisak of The Associated Press.