Nearly every aspect of Donald J. Trump’s life and career has been under scrutiny from the justice system over the past several years, leaving him under criminal indictment in four jurisdictions and being held to account in a civil case for what a jury found to be sexual abuse that he committed decades ago.
But a ruling on Tuesday by a New York State judge that Mr. Trump had committed fraud by inflating the value of his real estate holdings went to the heart of the identity that made him a national figure and launched his political career.
By effectively branding him a cheat, the decision in the civil proceeding by Justice Arthur F. Engoron undermined Mr. Trump’s relentlessly promoted narrative of himself as a master of the business world, the persona that he used to enmesh himself in the fabric of popular culture and that eventually give him the stature and resources to reach the White House.
The ruling was the latest remarkable development to test the resilience of Mr. Trump’s appeal as he seeks to win election again despite the weight of evidence against him in cases spanning his years as a New York developer, his 2016 campaign, his efforts to overturn his 2020 election loss and his handling of national security secrets after leaving office.
The federal case accusing him of plotting to retain power despite his defeat at the polls three years ago paints him as a threat to democracy, as does a similar prosecution in Georgia. The classified documents case portrays him as willing to obstruct justice to cover up a reckless disregard for the laws that govern the handling of such documents. A New York prosecution stemming from hush-money payments to a porn star in the closing stages of the 2016 election sets out evidence of the kind of political skulduggery he professes to want to eradicate from Washington.
So far none of those cases has discernibly hurt Mr. Trump’s campaign in the race for the Republican presidential nomination, which polls suggest he is leading by large margins. In fact, polls show the indictments have consolidated his support among Republicans. The prosecutions have helped his fund-raising.
Whether the effect of Justice Engoron’s ruling is any different remains to be seen. But his finding imperils both Mr. Trump’s public image and his business empire. The former president now faces not only the prospect of having to pay $250 million in damages, but he could also lose properties like Trump Tower that are inextricably linked to his brand.
Mr. Trump’s lawyer in the case, Christopher M. Kise, called the ruling “outrageous” and said the decision would be appealed. He called it “completely disconnected from the facts and governing law.”
“The decision seeks to nationalize one of the most successful corporate empires in the United States and seize control of private property all while acknowledging there is zero evidence of any default, breach, late payment or any complaint of harm,” Mr. Kise said.
Mr. Trump, in a lengthy post on his social media site, called the statements in the ruling about fraud “ridiculous and untrue,” and said the decision was a political attack against him in the midst of the presidential campaign.
In all of Mr. Trump’s recent legal travails, his typical tactics for self-preservation have largely failed him. When cornered, Mr. Trump has traditionally sought to bluster his way out of trouble, falling back on exaggerations or outright lies to escape.
These methods have served him well in the business and political arenas, where there is often little price to pay for bending the truth and where voters tend not to distinguish between gradations of prevarications. Those methods, though, have been much less effective so far in the courts, which operate according to strict standards of veracity and staid and sober rules.
In straightforward terms, Justice Engoron punctured Mr. Trump’s bubble of protective falsehoods about the way he conducted his business.
“In defendants’ world,” Justice Engoron wrote, “rent-regulated apartments are the same as unregulated apartments; restricted land is worth the same as unrestricted land; restrictions can evaporate into thin air.”
“That is a fantasy world,” the judge went on, “not the real world.”
Mr. Trump’s other weapon of choice — bullying his adversaries — has not fared much better in the courts. This month, federal prosecutors asked the judge overseeing his federal election interference case to impose a gag order on him, citing his “near daily” social media attacks on people involved in the proceeding and the threats they were generating.
Mr. Trump blew past an early warning from the judge in that case, Tanya S. Chutkan, to be mindful about what he said concerning the witnesses, prosecutors and potential jurors in the case. But if he thought he could simply muscle through the judge’s admonition, prosecutors called his bluff. Now Mr. Trump has placed himself on what could be a collision course with the judge that could result in his public statements being curbed in the middle of his presidential campaign.
Mr. Trump is being constrained by the very system he often uses to try to stymie opposition: the courts. In the last two years, Mr. Trump has filed a blizzard of legal actions against news networks, political critics and even the Pulitzer Prize committee. Several of those cases have been dismissed.
But Justice Engoron’s decision hinted at a trait that has longed defined Mr. Trump’s personality and approach to doing business. He has always sought to create his own reality, often getting away with it — up to a point.
In a 2006 lawsuit that Mr. Trump filed against the journalist Timothy O’Brien, the author of the book “TrumpNation: The Art of Being The Donald,” which estimated that Mr. Trump’s net worth was no greater than $250 million, the future president sat for a deposition and made a surprising statement about how he calculates the value of his holdings.
“My net worth fluctuates, and it goes up and down with the markets and with attitudes and with feelings, even my own feelings, but I try,” Mr. Trump said.
A judge ultimately dismissed his suit.
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