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 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…


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