Trump and His Family Are Fined $355 Million for Fraud—and a Lack of Remorse That “Borders on Pathological”

New York Supreme Court Justice Arthur Engoron ordered Donald Trump to pay $355 million in fines for business fraud in an excoriating decision on Friday that also imposes major penalties on the former president’s family and business associates. Both Eric Trump and Donald Trump Jr. are each liable for $4 million, while former CFO Allen Weisselberg is on the hook for $1 million.

The ruling, if upheld, marks the end of the Trump Organization as we know it: Engoron barred Trump from serving as an officer in any New York corporation or legal entity for three years, and prohibited him from applying for loans from any financial entity in the state. The judge has effectively hobbled the entire Trump corporate empire.

The lawsuit that culminated in Friday’s sweeping decision was brought by New York Attorney General Letitia James, who spent years building a case against the former president’s business. James argued that Trump and his associates consistently overvalued their assets by millions of dollars, defrauding banks and investors while enriching themselves. Engoron sided with James in a September ruling, determining that Trump was liable for a wide range of fraudulent conduct. He then conducted a trial to determine the appropriate punishment for each defendant. (The case was tried without a jury.)

During trial, members of the Trump family took the stand to defend their father’s business dealings, with little success; Engoron declined to credit their testimony in his Friday opinion, noting that Eric Trump actually reversed himself on the stand after evidence emerged that he had lied under oath. Trump himself took the stand, as well, assuming a combative and antagonistic pose toward the judge, whom he publicly derided as a partisan hack. The former president, Engoron wrote in his Friday opinion, “rarely responded to the questions asked, and he frequently interjected long, irrelevant speeches on issues far beyond the scope of the trial. His refusal to answer the questions directly, or in some cases, at all, severely compromised his credibility.”

This theme of mendacity and impenitence ran throughout Engoron’s ruling. In a remarkable passage, he wrote that the Trump family’s “complete lack of contrition and remorse borders on pathological. They are accused only of inflating asset values to make more money. The documents prove this over and over again. … 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.” This refusal to admit to their unlawful misdeeds persuaded Engoron that they “will engage in [fraud] going forward unless judicially restrained.” He therefore affirmed his earlier decision to have an independent monitor, the retired judge Barbara Jones, oversee the business’s finances and assets.

The $355 million penalty is, to put it mildly, substantial, and not the first time this year Trump has been ordered by a court to cut a check with two commas and at least seven zeroes on it. Just last month he was ordered to pay out over $83 million after losing the defamation case brought by the writer E. Jean Carroll. That was actually the second penalty Trump was compelled to pay her: A New York jury previously found that Trump sexually assaulted and defamed Carroll, awarding her $5 million in damages.

Some quick back-of-the-envelope math here shows just how dire the self-proclaimed multibillionaire’s financial situation is getting. Reporting from late October pegged Trump’s cash holdings at $425 million. This most recent penalty from New York state, combined with the two verdicts in the Carroll cases, tally to $438 million. And actually, it’s worse than that, since Engoron stipulated that Trump is prohibited from borrowing money from any New York bank for the next three years. That ban will handicap his attempt to appeal. Moreover, New York law could force him to pay a hefty 9 percent interest rate on the judgment, which would push the original $355 million north of $450 million.

Trump will undoubtedly appeal Friday’s decision, and he is not required to post bond while he does so. However, if he fails to post bond, the state can begin collecting on the judgment in 30 days’ time. At that point, Attorney General James can seize Trump’s assets, including real property; in other words, his real estate holdings in New York, like Trump Tower, are vulnerable to seizure and potential sale.

There are numerous cases still pending against the former president. The millions of dollars still forthcoming in attorneys’ fees alone now look financially ruinous, and have already been a major drain on his campaign coffers: His political fundraising committees spent $50 million in 2023 alone to cover legal fees, diverting much-needed money away from his presidential campaign. In his federal court cases, Trump has deployed a successful tactic of endless delays to avoid judgment; in New York, his obstructive tactics have failed spectacularly. The state judiciary has shown little interest in running interference for him and his associates, and there is a very strong chance that Engoron’s penalties will be upheld, in large part or in full, once all appeals are finished. Short of a criminal conviction, it is difficult to imagine a more devastating legal and financial blow to Trump.