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Trump Will Face His Greatest Fears as Two Legal Threats Coincide Monday

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 another case. The New York attorney general, Letitia James, who brought that civil fraud suit against the former president and his family business, might begin to collect as soon as Monday.

To avoid a mortal threat to the Trump Organization, Mr. Trump must persuade another company to post a bond on his behalf, promising that it will cover the judgment if he loses a pending appeal and fails to pay. Yet Mr. Trump’s lawyers in court papers said that securing the bond would be a “practical impossibility,” because he would need to pledge some $550 million in cash and liquid investments as collateral to the bond company — an admission that laid bare the former president’s cash crunch.

Unless Mr. Trump strikes an 11th-hour deal, Ms. James could freeze his bank accounts, and begin the long and complicated process of seizing some of his properties. And barring Mr. Trump’s lawyers achieving an improbable legal triumph, the judge in his criminal case could set a trial date for as soon as next month.

The twin threats — on the same day, in the same town — crystallize two of Mr. Trump’s greatest and longest-held fears: a criminal conviction and a public perception that he does not have as much cash as he claims.

For decades, Mr. Trump employed a broad array of tactics to keep those fears at bay, learning from his well-connected father and his own ruthless lawyer and fixer, Roy M. Cohn. After fending off local and federal investigations, not to mention financial ruin, Mr. Trump came to believe that any problems could be solved by personal connections — and a whole lot of money.

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