If Convicted, Weisselberg Could Spend the Rest of His Life in Jail; Will he Flip?

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NEW YORK, NEW YORK - JULY 01: Trump Organization finance chief Allen Weisselberg appears in a New York court after turning himself into authorities on July 01, 2021 in New York City. According to reports, federal prosecutors with the Manhattan district attorney's office have charged the Trump Organization, and its CFO Weisselberg, with tax-related crimes. (Photo by Spencer Platt/Getty Images)

On Thursday afternoon, Allen Weisselberg, the longtime chief financial officer of the Trump Organization, was charged with fifteen felony counts including conspiracy, criminal tax fraud and falsifying business records. He’s accused of evading taxes on $1.76 million in perks provided by the former president’s business.

Manhattan prosecutors said the “off-the-books tax fraud scheme” lasted for 15 years. The indictment suggests that other Trump employees received similar perks, like car payments and rent money. The Trump Organization and the Trump Payroll Corporation were also charged.

The 73-year-old Weisselberg faces the prospect of spending the rest of his life jail. Just one of the charges against him – grand larceny in the second degree – carries a 5 to 15 year prison sentence. Weisselberg – and the Trump-owned companies – entered not guilty pleas. Prosecutors confiscated Weisselberg’s passport, who was deemed “a flight risk.” He was then released without bail.

The Boston Globe provides more details on the charges filed against Weisselberg:

According to the indictment, Weisselberg paid for rent on his Manhattan apartment with company checks and directed the company to pay for his utility bills and parking. The company also paid for private school tuition for Weisselberg’s grandchildren with checks bearing Donald Trump’s signature, for Mercedes-Benz cars driven by Weisselberg and his wife, and gave him cash to hand out tips around Christmas.

Such perks were listed on internal Trump company documents as part of Weisselberg’s employee compensation, but were not included on his W-2 forms or otherwise reported and the company did not withhold taxes on their value, prosecutors said.

It’s clear that the ultimate target of the two-year investigation conducted by the Manhattan District Attorney and New York State Attorney General is former President Donald Trump.

In a press release, NY AG Letitia James said the probe continues:

“Today is an important marker in the ongoing criminal investigation of the Trump Organization and its CFO, Allen Weisselberg. In the indictment, we allege, among other things, financial wrongdoing whereby the Trump Organization engaged in a scheme with Mr. Weisselberg to avoid paying taxes on certain compensation. This investigation will continue, and we will follow the facts and the law wherever they may lead.”   

More from Bloomberg on the pressure campaign against Weisselberg, who can provide prosecutors with damning information on Trump and his business dealings:

Trump isn’t named in the charges, but the case may only be the opening salvo by the district attorney, who has been probing possible bank and insurance fraud at the company as well. The charges against Weisselberg significantly ratchet up the pressure on the CFO to cooperate with prosecutors.

Cooperation from Weisselberg could lead to a more expansive case against the company and raise the prospect of a historic and politically charged prosecution of a former president. With a trial unlikely before next year, the CFO will have months to decide whether to fight the charges or plead guilty and possibly strike a deal with prosecutors. A Trump executive for four decades, Weisselberg has unique insight into the former president’s finances and business deals.

The indictment against Weisselberg and the Trump business entities makes clear that prosecutors have a trove of documents, digital files, and grand jury testimony that implicates Weisselberg – and others – in malfeasance. According to the indictment, Trump signed tuition checks made out to the private school of Weisselberg’s grandchildren.

The Trump Organization released a statement calling Weisselberg “a loving and devoted husband, father and grandfather who has worked at the Trump Organization for 48 years.” After he was arraigned on Thursday, Trump released an additional statement asserting, “The political Witch Hunt by the Radical Left Democrats, with New York now taking over the assignment, continues. It is dividing our Country like never before!”