Photo: Chip Somodevilla (Getty Images)

The last time Donald Trump’s longtime friend and informal adviser Roger Stone pissed off U.S. District Court Judge Amy Berman Jackson, he apologized profusely, realizing she could send him to jail pending his criminal trial for lying to Congress.

That time, Stone had posted on Instagram what clearly can be interpreted as a threat against Jackson. The post contained a photo of the judge with the crosshairs of a firearm in the background.

For that little stunt, Jackson issued a full gag order that prohibited Stone from making any public statements about his case, the court, and Special Counsel Robert Mueller’s ongoing investigation into Russian collusion with the Trump campaign in the 2016 presidential election.

Stone said at the time that he was “heartfully sorry,” according to CBS News, and that he was “kicking [himself] over [his] own stupidity.”

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Apparently, Stone wasn’t kicking himself hard enough, because the judge is demanding that his lawyers tell her by Monday why they never mentioned a book that appears to be forthcoming and addresses the Mueller investigation.

In a court order on Friday, Jackson told Stone’s lawyers they would have to explain “why this matter — which was known to the defendant — was not brought to the court’s attention,” Bloomberg News reported.

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Her comments appear to respond to a Feb. 18 Instagram post by Stone promoting a book he wrote called The Myth of Russian Collusion. The post said the book would be on sale on March 1. As Politico pointed out, it appears to be an updated version of a book Stone published in 2017, “with an explosive new introduction” written by Stone.

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Stone appeared before the judge three days after that Instagram post, so there is no way he or his attorneys would have forgotten about it.

It also was reported last week that Stone has a bunch of Proud Boys working for him who have continued to post on social media about the case, which also could be a violation of the gag order. One of them, Rey Perez, attacked the “liberal media” in a tweet just a day after the full gag order was issued and proclaimed Stone’s innocence. It appears that Twitter has since suspended Perez’s account.

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And after former Trump consigliere Michael Cohen testified this week before the House Oversight and Reform Committee about the president’s alleged crimes, Stone sent a text message to BuzzFeed News saying, “Mr. Cohen’s statement is not true.” While brief, that message also appears to be a violation of the gag order. It remains to be seen what the judge will do about all of this.

Stone was indicted in late January by Mueller and charged with lying to Congress, obstruction, and witness tampering.