The penalty caps a three-month trial in a lawsuit brought by New York Attorney General Tish James. It comes just weeks after a federal jury in a separate case ordered Trump to pay $83.3 million in damages to the writer E. Jean Carroll over defamatory statements he made while president in response to her rape accusation.

And combined with the $5 million penalty Trump was ordered to pay to Carroll in a separate trial last year, it means the frontrunner in the Republican presidential primary now owes $443.1 million in judgments. (Trump is appealing the earlier Carroll verdict, and he has vowed to appeal the verdicts in both the more recent Carroll trial and the civil fraud trial.)

It’s not clear if Trump has enough cash on hand to pay those penalties without selling any assets.

In addition to the penalties aimed at Trump himself, Engoron imposed measures that may significantly alter the operations of the Trump’s family business, the Trump Organization. Engoron banned Trump’s two adult sons, Eric Trump and Donald Trump Jr., who are executive vice presidents of the company, from running New York companies for two years and fined them more than $4 million each. And he ordered a court-appointed monitor to continue overseeing the company’s operations for another three years.

Engoron also fined former Trump Organization executive Allen Weisselberg $1 million.

A lawyer for Trump, Chris Kise, said the former president plans to appeal the verdict, calling the decision a “tyrannical abuse of power.”

“The Court today ignored the law, ignored the facts, and simply signed off on the Attorney General’s manifestly unjust political crusade against the front-running candidate for President of the United States,” Kise said in a statement.

In a pretrial ruling last fall, Engoron found that Trump systematically inflated his assets on financial statements, so the trial focused largely on whether those fraudulent statements were used as a basis for banks like Deutsche Bank to give Trump preferential terms on loans that he wouldn’t have received if his net worth had been lower.

Because it was a bench trial, meaning there was no jury, Engoron alone decided the verdict and the scope of the penalties. James had asked the judge to issue a $370 million penalty.

In his written decision Friday, Engoron took aim not only at Trump and the other defendants’ actions, but also at their reaction to the accusations contained in the lawsuit.

“Defendants did not commit murder or arson. They did not rob a bank at gunpoint. Donald Trump is not Bernard Madoff. Yet, defendants are incapable of admitting the error of their ways. Instead, they adopt a ‘See no evil, hear no evil, speak no evil’ posture that the evidence belies.”

James’ case included accusations that Trump’s financial statements overvalued several flagship properties, including his own triplex apartment in Trump Tower. According to evidence presented during the trial, Trump’s financial statements claimed the apartment was 30,000 square feet, when the true size was just under 11,000 square feet. James’ lawyers introduced a document Trump signed in 1994 that provided the true size of the property.

Trump’s primary defense, which he has repeated publicly and which he invoked during an angry and rambling turn on the witness stand, is that his financial statements contained “very, very powerful” disclaimers and therefore weren’t intended for use by banks or insurers.

The trial in state court in Manhattan was the first trial Trump attended since leaving office and the first at which he testified. Trump’s adult children also testified.

The trial was at times a raucous affair, punctuated by Trump and his lawyers’ repeated criticism of the judge’s principal law clerk, whom they disparaged as an improper influence on the judge and biased against the defense. Those criticisms, particularly a social media message Trump posted featuring a photo of the clerk, prompted the judge to implement a pair of gag orders — one barring Trump from speaking about the clerk and the other preventing his lawyers from doing so.

The judge found Trump violated the gag order twice, fining him a total of $15,000. In evaluating the second violation, Engoron called Trump to the witness stand to testify, an unexpected turn that resulted in the judge finding that Trump was “not credible” as a witness.

In addition to his focus on the clerk, Trump frequently attacked Engoron himself throughout the trial, both in social media messages and to the judge’s face. During his testimony, Trump suggested one of Engoron’s pretrial rulings was “ very stupid” and told him, “It’s a terrible thing you’ve done. You know nothing about me.” Trump continually ignored the judge’s repeated instructions to provide direct answers to questions, instead giving rambling responses that often sounded more like clips of Trump’s campaign rallies.

And at the end of the trial, Trump even delivered his own unsanctioned closing argument in defiance of Engoron’s efforts to corral the former president, accusing Engoron of having his “own agenda” and berating the judge.