Experts say a cash crunch in coming weeks could thrust the former president’s business into greater uncertainty than it has seen in decades

Hours after a New York judge ordered Donald Trump to pay a $355 million penalty for submitting false data to financial institutions, the former president railed against the decision during a fundraiser at his Mar-a-Lago Club with some of the Republican Party’s wealthiest donors.

Trump claimed at that Feb. 16 gathering that the judge in the civil fraud case had made history by ordering him to pay such a staggering sum, according to two people who were there. He suggested that the judgment was so severe that the public would consider it unfair and rally in support. Over and over, he returned to the penalty, livid at its size.

The episode offered a glimpse of Trump’s preoccupation with a legal decision that threatens his wealth and has thrust his business empire into greater uncertainty than perhaps any time since the 1990s, when his Atlantic City casinos fell into extreme debt, leading six of his companies to file for bankruptcy.

Trump, who built his business and political identities around boasts of financial savvy, now faces an immediate cash crunch of more than a half-billion dollars — the combined cost of two legal battles that will now test the limits of his personal wealth.

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