Judge Arthur Engoron’s warning that repeated violations of a gag order will result in “possibly imprisoning” President Trump brings the 45th commander in chief closer than he has ever been to the inside of a jail cell.

That warning, and the imposition of an accompanying $5,000 fine, were spelled out in a Friday afternoon order. Judge Engoron is presiding over the civil fraud case brought by New York’s attorney general, Letitia James. He imposed a partial gag order on Mr. Trump a little more than two weeks ago for what he calls “an untrue, disparaging, and personally identifying” post about his law clerk.

That post, made to Mr. Trump’s social media platform Truth Social, featured a picture of the clerk, Allison Greenfield, alongside Senator Schumer. Mr. Trump baselessly called Ms. Greenfield the Senate majority leader’s “girlfriend” and linked to her private Instagram account. 

Judge Engoron notes that 17 days ago, when the order was issued, he ordered Mr. Trump to remove the post immediately,” and the former president represented that he had. Judges are customarily protective of their clerks, recent law school graduates who work closely with them and often write the first drafts of their opinions.  

In court, Judge Engoron related that he learned that the “offending post was never removed” from DonaldJTrump.com. This, he reckons, “is a blatant violation of the gag order.” The jurist adds that “incendiary untruths can and have led to serious physical harm. I will now allow the defendant to explain why this should not end up with serious sanctions or I could possibly imprison him.”

The offensive post had been deleted from Truth Social, but remained for 17 days on Mr. Trump’s campaign website. Mr. Trump’s attorney, Christopher Kise, attempting to avert a carceral outcome, called the lingering post “truly inadvertent,” and explained that the “Truth Social post was taken down when the court asked” and that Mr. Trump “never made any more comments about court staff, but it appears no one took it down on the campaign website.” Mr. Kise called that oversight “unfortunate” and the result of “campaign structure.”

Judge Engoron was not persuaded by that line of argument. In court, he noted that “Donald Trump is still responsible for the large machine, even if it is a large machine.” In his order, he reckons that even giving Mr. Trump the “benefit of the doubt, he still violated the gag order.” He adds that “we are way beyond the ‘warning’ stage when it comes to the order.

Judge Engoron did not issue a decision with respect to contempt during the Friday morning hearing, but one could come as soon as later in the day. Mr. Trump also faces a gag order at the District of Columbia, where Judge Tanya Chutkan has promised “serious sanctions” in the event it is violated.

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This article has been updated from the bulldog edition.