Donald J. Trump is expected to spend his Monday morning in the courtroom of a New York judge who might soon preside over his criminal trial and, ultimately, throw him behind bars. And that’s not even the legal predicament that worries Mr. Trump most that day.

The hearing in his Manhattan criminal prosecution — in which he is accused of covering up a sex scandal to pave his way to the presidency — comes as he races to fend off a financial crisis arising from a $454 million judgment in…


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