After all the suspicion and anticipation, it was not a conspiracy involving Russia, widespread money laundering or a sweeping allegation of racketeering and corruption.
Instead, it was an investigation that uncovered the alleged abuse of run-of-the-mill perks — like car leases, apartments and school tuition — that transformed Donald J. Trump’s family business from real estate branding empire to criminal defendant.
On Thursday, prosecutors from the Manhattan district attorney’s office announced charges against the Trump Organization and its chief financial executive, Allen H. Weisselberg, alleging a scheme lasting over a decade in which Mr. Weisselberg failed to pay taxes on close to $2 million worth of perks and bonuses as the company benefited from helping him do so.
While there is no indication that Mr. Trump himself will face criminal charges anytime soon, the district attorney, Cyrus R. Vance Jr., has said that “the work continues,” and the former president will remain the focus of the investigation as prosecutors exert pressure on Mr. Weisselberg to cooperate. Mr. Trump has escaped numerous law-enforcement inquiries over the better part of three decades, and he could well do so again. Even so, the case brought by Mr. Vance on Thursday has already struck at the heart of Mr. Trump’s public image — the business of the businessman — in a way no other investigation has done.
The fallout could be significant. An indictment against a company — let alone a conviction — can jeopardize relationships with banks and business partners. The former president is facing down hundreds of millions of dollars in loans that need to be repaid, and the legal threat to his business could deal a blow to his finances.
And the charges could play into Mr. Trump’s decisions about his political future. In the past, his grievances have served as both personal motivation and political tool, and as he fought Mr. Vance’s subpoenas for his tax returns all the way to the United States Supreme Court, he added the investigation to the laundry list of legal troubles he recited for supporters. Indeed, some Republicans close to the former president believe he will now be better insulated from those he calls “New York radical-left prosecutors” if he campaigns for president in 2024, and aides said that anger over the indictment could well motivate him to run.
But several allies and advisers believe he would not risk losing another general election. On Wednesday, shortly after the indictments were filed, Mr. Trump said at a Fox News town hall that he had made a final decision on whether to run. He did not say what the decision was.
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Mr. Trump said in a brief interview on Thursday afternoon that the indictment was “a terrible thing for our country, and people are very angry about it.”
“Allen Weisselberg’s a very good man, and he’s been treated horribly,” he said, characterizing the indictment as political persecution.
Mr. Trump did not respond directly to a question about whether the organization had systematically avoided its tax burdens, as it stood accused of doing, but called the case “ridiculous.”
His reluctance to discuss the allegations in depth stood in contrast to his gloating after a real estate rival, Leona Helmsley, was charged with tax crimes in 1989, prompting Mr. Trump to call her a “disgrace to humanity.”
While the charges unveiled on Thursday represent a climax of sorts, they may also mark another step in the district attorney’s broader, continuing investigation into the former president, in which he has been joined by the New York state attorney general, Letitia James. The inquiry is focused on whether Mr. Trump effectively kept two separate sets of books: one for his bankers, in which he overstated the value of his properties, and another for the tax authorities, in which he understated them.
Mr. Weisselberg, who is approaching his fifth decade working for the Trump family and would know those books better than almost anyone, has been under intense pressure for months as prosecutors use every tool at their disposal to turn him into a cooperating witness. But the executive, whom a former co-worker described as a “disciple” for his devotion to Mr. Trump, will now have to weigh that loyalty against the prospect of spending time in prison.
Tax experts have said it is unusual to bring a criminal case solely on the failure to pay taxes on such perks, known as fringe benefits. However, those familiar with the methods of Mark F. Pomerantz, the experienced prosecutor Mr. Vance tapped to help lead the investigation, say that Thursday’s indictment could represent the starting point of a broader case.
“It certainly could serve as a building block. In any case involving an organization, you’re going to indict people and try to flip them,” said Robert S. Litt, a former federal prosecutor and Justice Department official who has been friends with Mr. Pomerantz for decades. “They’ve more or less thrown the book at Weisselberg, and if the proof is strong enough and his concern about going to jail strong enough, he may decide to save himself at the expense of others.”
Mr. Vance’s lawyers had to wait their turn. Though their investigation opened in summer 2018, they were asked by federal authorities looking into related issues to stand down. The following year, the Manhattan prosecutors’ efforts were stalled once more when Mr. Trump sued to block a subpoena for his financial records, setting off a 17-month legal battle that went to the Supreme Court twice. And of course, there was a pandemic disrupting foundational work Mr. Vance’s office could have done while waiting for the court to make its decision.
The prosecutors shifted emphasis over time, from the hush money payments made to the pornographic film star who said she had had an affair with Mr. Trump, to the potential tax and bank-related fraud that court documents suggested had intrigued them as they dug into whether the company manipulated the valuation of its properties.
But in February, the Supreme Court ruled against Mr. Trump for the second and final time. And once Mr. Vance had Mr. Trump’s tax returns in hand, there was a fundamental logic to his office’s work. His prosecutors had been focused on possible financial crimes that would require that they prove intent.
Mr. Trump, famously, does not use email or texts, or keep written records that could reveal his intent to a jury. So the prosecutors directed their attention to the executive who knows more about the Trump Organization’s business dealings than anyone else and whose knowledge could become evidence were he to become a witness: Mr. Weisselberg.
“This is a very standard approach when you’re dealing with any kind of organization, whether it’s the mafia or whether it’s a corporation,” Mr. Litt said. “You work your way up the ladder and see how high you can get.”
David Enrich contributed reporting.
