Former President Donald Trump speaks at a rally in Wellington, Ohio, June 26.

Former President Donald Trump speaks at a rally in Wellington, Ohio, June 26.

Photo: Tony Dejak/Associated Press

Donald Trump looked crestfallen amid his victory on election night 2016. As I duly related some weeks later, sociologist Anne Nassauer, applying well-established metrics, told me: “We can only speculate as to why President-elect Trump showed facial expressions of sadness. It is surprising that he showed these expressions directly after his victory in the election.”

Speculating wasn’t hard. This week is why. Mr. Trump, who is not the fool some imagine, knew winning the presidency was a dangerous mishap from a personal legal standpoint. Mr. Trump, until then, mainly tussled with sharpies who wanted only some of his money, not his destruction. He also knew that in our overgrown regulatory state, prosecutors can find something on anybody, even those who conduct their affairs with a scrupulousness foreign to Mr. Trump.

It’s “political,” Mr. Trump says of this week’s charges. Yes, inevitably and partly. That’s why people with Mr. Trump’s deep pockets and checkered history are unwise to go into politics, however much it might benefit the nation to have a broadly welcoming presidential talent pool.

The charges brought by Manhattan District Attorney Cyrus Vance Jr. and New York Attorney General Letitia James are over the top for what amount to tax violations related to employee compensation. Larceny? Who stole what from whom? Mr. Trump’s company and its major-domo, Chief Financial Officer Allen Weisselberg —though not Mr. Trump himself so far—are accused of doling out perks as normal business expenses, thereby avoiding personal income and payroll taxes.

Mr. Trump’s lawyer said, probably accurately, that such complaints usually are settled as a civil matter with the Internal Revenue Service for the reasons alluded to above. The IRS cares mainly about getting maximum money at least cost for its enforcement efforts. Not so elected officials such as Mr. Vance and Ms. James. If the prosecution is a giant net loser financially for the state of New York, that’s fine with them.

If the charges are right, among the expenses Mr. Trump picked up for his employees to maximize the bang for his compensation buck were school tuition, a company Mercedes, and free apartments for employees and their family members.

Mr. Trump would have dispensed these goodies because in New York City, where the top cumulative income-tax rate is 52%, he could cut in half the cost of providing after-tax compensation to a high-level employee.

Tax systems, which both fund the government and shape the incentives that drive the private economy, are too important not to be regarded with extreme practicality. Every tax system operates on the margin between people’s desire to live within the law and their incentive to cheat, which smart tax designers keep in mind.

You will be right to ask: If Mr. Trump is now to be held to this standard of tax honesty, will others? When and if a grand jury gets around to indicting him for offenses reportedly related to how buildings were valued for tax and banking purposes, the same questions will simmer. As the New York Times reported in 2018 after digging through a decade of Trump family tax data, the Trumps use the same appraisers, tax lawyers and accountants that other New York real-estate families use, albeit the others are not so imprudent as to put their heads in the tiger’s mouth by contesting with the nation’s political class for its top prize.

It wouldn’t be right to leave this subject without a passing note. On the same behavior that is rightly treated as offensive if Mr. Trump does it, Congress built the distortion that many diagnose as a root cause of our healthcare-financing maladies: employers being allowed to hand out health coverage to employees as untaxed compensation, which ends up inflating the price of healthcare and disproportionately benefits wealthier taxpayers.

The likelihood that Mr. Trump, for all his incentive to signal otherwise, would run for president again always seemed to me low and seems lower now. His investment in the stolen-election lie struck me as the opportunism of the checkers player, without a plan. He realized if he backpedaled and ran up the white flag his audience would drift away. His ability to reward and punish by mobilizing his supporters would disappear. His way into the minds of 40% of voters would be a power officeholders and office-seekers would no longer have to fear (it’s eroding anyway thanks to the social media freeze-out). I expect when Mr. Trump enters settlement talks with his latest legal assailants, he intends this ability to make trouble or refrain from making trouble will be a bargaining chip on the table too.

While the media focused almost exclusively on Donald Trump's speech at CPAC 2021, there were strong pitches from other potential Republican Party leaders including Kristi Noem, Ted Cruz, Ron DeSantis, Tom Cotton and Rick Scott. Images: Getty/Zuma/AP/Reuters Composite: Mark Kelly The Wall Street Journal Interactive Edition