Donald Trump and the judge presiding over his hush money trial are staring each other down with profound implications for the former president, the coming election and the rule of law in the United States.

Juan Merchan is now closer than any judge in American history to putting an ex-president behind bars after laying down a red line he says he may have no choice but to enforce if Trump does not start obeying the rules.

Merchan on Monday found Trump had yet again violated a gag order that precludes attacks on witnesses, the jury and others, days after he fined him $1,000 each for nine previous transgressions. But he noted that the defendant wasn’t getting the message and warned he would have to escalate if necessary and appropriate in the future, as much as he sees the option as a “last resort.”

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The timing of the judge’s warning was significant because several moments of maximum stress are approaching for Trump with testimony expected soon from his former lawyer Michael Cohen and former adult film star Stormy Daniels.