Former President Donald Trump used to call himself one of the nation's foremost experts on taxes, but at a rally in Sarasota, Florida, on Saturday night, he seemed baffled at the idea that having your company pay for private school in Manhattan for your grandchildren might be considered taxable income. Trump also appeared to acknowledge the thrust of the crimes Manhattan prosecutors charged his company and CFO, Allen Weisselberg, with last week: fraudulently avoiding paying taxes on $1.7 million worth of income, booked in a second secret ledger.

Why would he admit that out loud, on camera? Trump "has a very long history of conflating legal issues with public relations issues," New York Times reporter Maggie Haberman told CNN on Monday. He will "repeat the charges out loud and say there's nothing wrong with it, say that everybody does it," but the difference now is that "an indictment has been filed" against Weisselberg and the Trump Organization, Trump himself is "still under investigation, and he no longer has a shield of prosecution" from when he was president. 

Trump may never personally be charged but "what he has just done is basically acknowledge that yes, he was making these payments, he's trying to argue they were for something else but most lawyers would tell somebody connected to a case like this the less you say, the better," Haberman said. "That's just never his style. He always believes he's gonna convince someone. He's taking a risky gamble right now," though, because "if this goes to trial, there will be a jury, there will be a jury that will likely be less predisposed to see things his way than, say, Republicans senators in an impeachment trial." 

Trump probably thinks the same playbook he's been using for nearly 50 years will work once more, Haberman said, but he "is obviously very worried. If he weren't worried, he wouldn't be talking about it at a political rally." 

Unfortunately for anyone who is or will be charged at the Trump Organization, "these cases get litigated in the courts, not in rallies," former prosecutor Elie Honig said later on CNN. Trump's "bizarre statement" Saturday night was "a partial admission — he admits the core facts that yes, we pay people off the books and no, we did not pay taxes on it" — and it "absolutely can be used against him in court."