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A good rule of thumb for anyone running a small or large business is to never be in a position where you have to say, “One of our top executives is a convicted criminal.” Unfortunately for the Trump Organization, that’s exactly the situation it is about to find itself in, as Allen Weisselberg, its longtime chief financial officer, pleaded guilty on Thursday to running a yearslong tax scheme with Donald Trump’s family business. And if you are thinking this sounds like bad news for the ex-president, you are thinking right!

While Weisselberg’s plea deal does not require him to cooperate with the Manhattan district attorney’s broader criminal investigation against Trump the man, he will likely be a central witness during the government’s trial against the Trump Organization in October, where, per The New York Times, “he will have to testify about his role in the scheme to avoid paying taxes on lavish corporate perks” if he is called as a witness. While the Trump Organization has pleaded not guilty to the cornucopia of crimes it was charged with in July 2021—including conspiracy, grand larceny, and multiple counts of tax fraud and falsifying records—it’s pretty clear that having one of its most powerful employees detail the many crimes he committed while working for the joint will not be great for its defense.

If Weisselberg tells the truth during the trial—i.e. he tells the jury about how, as CFO of the company, he engaged in a scheme to compensate himself and other executives with off-the-books perks for which taxes were not paid, and personally dodged taxes on $1.76 million of income over the last 15 years—he’ll be given a five-month prison sentence, of which he would probably only serve 100 days, according to the reported details of the plea deal. He’d also have to fork over nearly $2 million in taxes, penalties, and interest. Among the perks Weisselberg received as part of the scam were an apartment on the Upper West Side, leased Mercedes-Benzes, and private school tuition for his grandchildren. When the indictment against Weisselberg and the Trump Organization was unsealed last year, it showed the company kept actual spreadsheets of its alleged crimes. Responding to the news at the time, company executives Don Jr. and Eric Trump argued that people dodge taxes all the time and it’s not a big deal; they also claimed that the $1.76 million that Weisselberg avoided paying the IRS was “pennies on the dollar.”

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While the DA’s criminal investigation against Trump himself has seemingly lost speed, the veteran prosecutor who resigned in February insisted it wasn’t for a lack of evidence, saying in his resignation letter: “The team that has been investigating Mr. Trump harbors no doubt about whether he committed crimes—he did.” Manhattan district attorney Alvin Bragg, who took over the office in January, said in a statement in April that the probe was ongoing.

Trump’s allies look on the bright side

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