Former President Donald Trump must pay nearly $355m (£281m) to New York state for lying about the values of his properties, a judge has ruled.
Judge Arthur Engoron also banned him from serving as a company director or taking out loans from banks in the state for three years.
The New York real estate mogul escaped having some of his companies dissolved, which could have meant bankruptcy.
Speaking from his Florida estate, Mr Trump said he would appeal the ruling.
"A crooked New York state judge just ruled I have to pay a fine for $355m for having built a perfect company," the former president said from Mar-a-Lago on Friday, calling the ruling a political witch hunt.
"It's a very sad day for - in my opinion - the country."
In the ruling on Friday, Judge Engoron referred to previous allegations of wrongdoing in justifying the large amounts he ordered the defendants to pay, writing that they "are likely to continue their fraudulent ways" unless he imposed a "significant" penalty.
He made specific reference to the Trump Organization's conviction in a criminal tax fraud case in 2022, where a jury found it had enriched its top executives with off-the books benefits for more than a decade.
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"Their complete lack of contrition and remorse borders on pathological," Judge Engoron wrote in an at times scathing 92-page decision.
Later he said: "The frauds found here leap off the page and shock the conscience."
Still, Mr Trump's empire was spared from one of the worst potential outcomes - the cancellation of its business licences, known as the corporate death penalty.
Instead, the judge ordered two tiers of oversight - an independent monitor to report to the court for up to three years and a separate independent director of compliance to be installed.
The judge is also requiring Mr Trump pay interest on the profits he made by committing the fraud (known as "prejudgment interest"), which could bring the final amount penalty total to around $450m.
Along with what Mr Trump has been ordered to pay, his two adult sons and co-defendants, Donald Jr and Eric, must each pay $4m. They are barred for two years from doing business in New York, while another co-defendant, Allen Weisselberg, the former chief financial officer of the Trump Organization, has been ordered to pay $1m.
Additionally, Mr Trump, his company, and its affiliates cannot apply for loans in New York for three years.
Both of Mr Trump's sons denounced the ruling on social media, with Donald Jr claiming the judgment was politically motivated and Eric calling the judge "a cruel man".
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In her civil case, New York Attorney General Letitia James, a Democrat, had accused all four defendants and the wider Trump Organization of massively inflating property values and lying on financial statements so they could borrow large sums of money at favorable interest rates. She had asked for a fine of $370m.
Speaking on Friday, she said: "There cannot be different rules for different people in this country, and former presidents are no exception."
"Donald Trump may have authored the art of the deal, but he perfected the art of the steal," she told a news conference.