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A New York judge on Friday handed Donald J. Trump a crushing defeat in his civil fraud case, finding the former president liable for conspiring to manipulate his net worth and ordering him to pay a penalty of nearly $355 million plus interest that could wipe out his entire stockpile of cash, The New York Times reported.

The decision by Justice Arthur F. Engoron caps a chaotic, yearslong case in which New York’s attorney general put Mr. Trump’s fantastical claims of wealth on trial. With no jury, the power was in Justice Engoron’s hands alone, and he came down hard: The judge delivered a sweeping array of punishments that threatens the former president’s business empire as he simultaneously contends with four criminal prosecutions and seeks to regain the White House.

Justice Engoron barred Mr. Trump for three years from serving in top roles at any New York company, including portions of his own Trump Organization. He also imposed a two-year ban on the former president’s adult sons and ordered that they pay more than $4 million each. One of them, Eric Trump, is the company’s de facto chief executive, and the ruling throws into doubt whether any member of the family can run the business in the near term.

The judge also ordered that they pay substantial interest, pushing the penalty for the former president to $450 million, according to the attorney general, Letitia James.

Mr. Trump will appeal the financial penalty but will have to either come up with the money or secure a bond within 30 days. The ruling will not render him bankrupt, because most of his wealth is in real estate, which altogether is worth far more than the penalty.

Mr. Trump will also ask an appeals court to halt the restrictions on him and his sons from running the company while it considers the case. In a news conference from his home in Mar-a-Lago on Friday evening, he attacked Ms. James and Justice Engoron, calling them both “corrupt.”