The potential charges would include whether Trump's company properly recorded and paid taxes on benefits Weisselberg and other executives received, like tens of thousands of dollars in private school tuition for one of his grandchildren, rents on apartments, and car leases.
According to the Times, prosecutors have been building a case against Weisselberg for months in an attempt to pressure him to cooperate with the investigation into the former president. As a longtime Trump Organization employee, Weisselberg is assumed to have inside knowledge about Trump's dealings that could prove useful to investigators seeking to prove that the former president or his employees committed a crime.
If Vance proceeds, these would be the first criminal charges filed against Trump's company in the course of the Southern District of New York's highly publicized investigation into Trump and his business dealings.
Trump's lawyers reportedly met with prosecutors Thursday in an attempt to persuade them to abandon plans to drag the Trump Organization to court over what may be a trivial matter. Legal experts specializing in tax law told the Times that it would be "highly unusual to indict a company just for failing to pay taxes on fringe benefits." None of the experts could cite a recent example of another company facing similar charges over perks like company cars.
"Still, an indictment of Mr. Trump's company could deal a significant blow to the former president just as he has flirted with a return to politics," the Times acknowledged, a point Trump will doubtlessly use in his longstanding and ongoing complaints that the investigation into his businesses led by Vance, a Democrat, is a partisan "witch hunt."
After the Times published its report, Trump's lawyer, Ronald Fischetti, blasted the potential charges in a statement to NBC News after noting that "there are no charges that are going to be leveled against Mr. Trump himself."
"The corporate office will plead not guilty and we will make an immediate motion to dismiss the case against the corporation," Fischetti said. "Mr. Trump is outraged that they are still going after him by going after his company where he has loyal employees for decades.
"It looks like they are going to come down with charges against the company and that is completely outrageous," Fischetti said. "I've been practicing for over 50 years and I've never seen a case like this where they would indict or charge an individual or a company on tax evasion for using a company car or company apartment and then tie it to the company that he is working for without any evidence that what he did benefited the company."
Fischetti said New York prosecutors were persecuting Weisselberg because he would not turn on Trump.
"They could not get Allen Weisselberg to cooperate and tell them what they wanted to hear and that's why they are going forward with these charges," Fischetti said. "And they could not get him to cooperate because he would not say that Donald Trump had knowledge or any information that he may have been not deducting properly the use of cars or an apartment."
Last month, District Attorney Vance convened a grand jury to review the evidence from his investigation into Trump's business dealings and decide whether to indict the former president. It is unclear if more potential criminal charges will be announced against the Trump Organization or the former president.