Throughout his political career, Donald Trump has claimed to have an encyclopedic understanding of many subjects, but the Republican is especially proud of his tax-policy expertise.
"I think nobody knows more about taxes than I do, maybe in the history of the world," Trump told voters in May 2016. He added five months later, "I understand the tax laws better than almost anyone."
Five years later, the former president's core business, the Trump Organization, is under criminal indictment, with New York prosecutors alleging that the business engaged in a 15-year-long tax fraud scheme. It was against this backdrop that Trump held a rally in Florida over the holiday weekend, lashed out at prosecutors, and as the Washington Post noted, "appeared to acknowledge the tax schemes while questioning whether the alleged violations were in fact crimes."
"They go after good, hard-working people for not paying taxes on a company car," he said at a rally in Sarasota, Fla. "You didn't pay tax on the car or a company apartment. You used an apartment because you need an apartment because you have to travel too far where your house is. You didn't pay tax. Or education for your grandchildren. I don't even know. Do you have to? Does anybody know the answer to that stuff?"
Joyce Vance, a former federal prosecutor and an MSNBC legal analyst, highlighted a video of the former president's comments and added, "Somewhere, a defense lawyer is beating his head into a brick wall, over and over."
As a rule, attorneys whose clients are under indictment have a few simple rules, starting with the most obvious: shut up. Criminal defendants have a right to remain silent, and their lawyers prefer that they exercise that right for a reason: the accused may say things in public that prosecutors will hear and use in court.
In this instance, the Trump Organization and its CFO stand accused of orchestrating an extensive tax-fraud scheme. While the defendants have all pleaded not guilty, that didn't stop Trump himself from standing on a Florida stage and suggesting to thousands of his followers that the schemes actually occurred.
His apparent defense -- to the extent that this could be characterized as a defense -- was that he "doesn't even know" whether the alleged criminal schemes were illegal, his earlier boasts about knowing more about taxes, "maybe in the history of the world," notwithstanding.
The problem is not just that Trump seems to believe he can talk his way out of this mess, it's also how familiar these circumstances are. It was nearly three years ago when The Atlantic's Adam Serwer wrote, "Donald Trump can't stop telling on himself." As regular readers know, it was a notable observation precisely because Trump has publicly disclosed his own misdeeds on multiple occasions.
Nick Akerman, a former Watergate prosecutor, said part way through Trump's term, "What he's been saying in public is the kind of thing I used to prosecute people for doing in private."
I can only assume that the district attorney's office in Manhattan hopes the former president just keeps talking.
Correction: I'd originally misstated the Trump Organization's plea. The above text has been corrected.