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Allen Weisselberg leaves a courthouse

Former Trump Organization CFO Allen Weisselberg leaves the Manhattan Criminal Courthouse in a mask after pleading guilty to criminal charges tied to a tax fraud case involving the company's business dealings. (Photo: Timothy A. Clary/AFP via Getty Images)

Ex-CFO Allen Weisselberg Pleads Guilty to 15 Felonies, Set to Testify Against Trump Organization

The former executive will serve only five months on Rikers Island if he testifies in the upcoming criminal trial of the business.

Jessica Corbett

Former Trump Organization Chief Financial Officer Allen Weisselberg on Thursday pleaded guilty to 15 felonies related to tax fraud in New York state court and is set to serve only five months in jail on Rikers Island if he testifies during the trial of the ex-president's family business.

"Criminal liability is usually a pretty big deal for a corporation—it's often a death sentence."

"Today Allen Weisselberg admitted in court that he used his position at the Trump Organization to bilk taxpayers and enrich himself," said Manhattan District Attorney Alvin Bragg in a statement. "Instead of paying his fair share like everyone else, Weisselberg had the Trump Organization provide him with a rent-free apartment, expensive cars, private school tuition for his grandchildren, and new furniture—all without paying required taxes."

"This plea agreement directly implicates the Trump Organization in a wide range of criminal activity and requires Weisselberg to provide invaluable testimony in the upcoming trial against the corporation," Bragg continued. "Furthermore, thanks to the incredibly hard work and dedication of the team prosecuting this case, Weisselberg will spend time behind bars. We look forward to proving our case in court against the Trump Organization."

Weisselberg, who also faces five years' probation, admitted to charges including grand larceny, criminal tax fraud, conspiracy, and falsifying business records from 2005 through June 2021. He will be required to pay nearly $2 million in taxes, penalties, and interest to New York City and state tax authorities before his sentencing. Bragg's office said the state will recommend prison time if the 75-year-old fails to abide by the conditions of his plea deal.

"In one of the most difficult decisions of his life, Mr. Weisselberg decided to enter a plea of guilty today to put an end to this case and the yearslong legal and personal nightmares it has caused for him and his family," said his lawyer, Nicholas A. Gravante Jr. "Rather than risk the possibility of 15 years in prison, he has agreed to serve 100 days. We are glad to have this behind him."

The Associated Press reported that "Weisselberg said nothing as he left court, offering no reply when a journalist asked him whether he had any message for" former President Donald Trump—who is a target of various other investigations but has not been charged in this case.

"The plea deal does not require Mr. Weisselberg to cooperate with the district attorney's broader criminal investigation of Mr. Trump, and his admissions will not implicate the former president," The New York Times explained. "His willingness to accept jail time rather than turn on Mr. Trump underscores the extent of his loyalty to a family he has served for nearly a half-century, and it helped stymie the larger effort to indict Mr. Trump."

The newspaper added:

In refusing to cooperate against Mr. Trump, Mr. Weisselberg fended off intense pressure from prosecutors. They saw Mr. Weisselberg as the ideal cooperator in their wider investigation focused on the former president and his business practices: He entered the Trump orbit in the early 1970s as a junior bookkeeper for Mr. Trump's father and climbed the ranks at the Trump Organization in the decades that followed, developing an encyclopedic knowledge of its finances.

Despite not securing Mr. Weisselberg's cooperation, the Manhattan district attorney... may still gain a victory from the deal. Prosecutors now can point to Mr. Weisselberg's admissions that he conspired with the Trump Organization—damning evidence against the company—when they face off at trial. And Mr. Weisselberg, an accountant who served a vital role as the company's financial gatekeeper, will be branded as a felon.

Just ahead of Weisselberg's anticipated plea, New Law School professor Rebecca Roiphe told Rolling Stone that "it is another Trump person being convicted of something, and it also reflects on him more than just the company he keeps. This is obviously conduct that occurred separately from his presidency and has to do with how he conducted his businesses. Whether or not he was directly involved in these actions, or knew about them or was criminally liable for them, it's serious and significant."

"It should—and does—bear upon his reputation as a businessperson in New York. Assuming they can convict the organization as well, it can have direct consequences on his business and his work and his business's ability to continue in New York," Roiphe said of Trump. "Criminal liability is usually a pretty big deal for a corporation—it's often a death sentence. The penalties could be so significant that the organization cannot survive past it. The penalties can be so high the company just doesn't exist, and it could ultimately end in the dissolution of the company."

Jury selection for the Trump Organization trial is scheduled to start October 24, noted Bragg's statement, which also thanked the city and state finance departments as well as New York Attorney General Letitia James and the investigators from her office.

During a deposition last week for a civil inquiry James' office is conducting into the Trump Organization's business practices, the former president invoked his Fifth Amendment right against self-incrimination over 440 times.

"I once asked, 'If you're innocent, why are you taking the Fifth Amendment?'" Trump said last week. "Now I know the answer to that question. When your family, your company, and all the people in your orbit have become the targets of an unfounded, politically motivated witch hunt supported by lawyers, prosecutors, and the fake news media, you have no choice."

The deposition came just days after Federal Bureau of Investigation agents raided Mar-a-Lago, Trump's Florida residence, and removed several boxes of materials, including classified documents. The search warrant indicates he is being investigated for potential violations of the Espionage Act, obstruction of justice, and unlawful removal of government records.

Meanwhile, the congressional select committee investigating the January 6, 2021 attack on the U.S. Capitol could also refer the twice-impeached former president—who is widely expected to run again in 2024—to the U.S. Department of Justice for criminal charges.

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