WASHINGTON _ As a self-described Republican dirty trickster, Roger Stone spent decades gleefully and gratuitously inspiring ire among his critics and opponents.
Now the former political adviser to President Trump is struggling to stay out of jail while awaiting trial in the Russia investigation.
Stone is due back in federal court on Thursday to face U.S. District Judge Amy Berman Jackson, who is overseeing his case and appears to be running out of patience with him.
He first angered the judge last month with an inflammatory Instagram post that included a crosshairs symbol next to her head. In response, Jackson tightened her gag order and barred Stone from saying almost anything in public about the case.
But Stone is in hot water again because he failed to tell Jackson about the imminent publication of a book called "The Myth of Russian Collusion," an updated version of a tome that was first released shortly after the 2016 election.
The book includes a new introduction that takes direct aim at special counsel Robert S. Mueller III by calling him "crooked."
An exasperated Jackson demanded more information about the book, and Stone's lawyers asked her forgiveness in a court filing on Monday.
"Having been scolded, we seek only to defend Mr. Stone and move ahead without further ado," they wrote.
It's unclear whether Jackson will agree with them. While overseeing the cases involving Paul Manafort and Richard Gates, the chairman and deputy chairman of Trump's campaign, she strictly policed gag order infractions.
Jackson sentenced Manafort, who pleaded guilty to conspiracy charges in September, to prison on Wednesday.
There could also be trouble over another Instagram post highlighted by prosecutors working for Mueller and the U.S. attorney's office in Washington, who are jointly handling the case.
The March 3 post showed a picture of Stone and the question "Who Framed Roger Stone?" _ a homage to the popular 1988 live action/animated feature film, "Who Framed Roger Rabbit."
Stone's gag order allows him to profess his innocence and raise money for his legal defense fund, but he's otherwise barred from commenting about his case in public.
Stone has pleaded not guilty to seven charges involving lying to the House Intelligence Committee about his conversations involving WikiLeaks, the organization that released thousands of hacked Democratic Party emails during the presidential campaign.
In their latest court filing, Stone's lawyers submitted emails about his book, which was originally called "The Making of the President 2016."
The publisher pitched the idea for an update in December as a way for Stone "to set the record straight, clear his name, reach a wider audience and make some money."
Stone was underwhelmed, complaining that the original printing didn't sell well and "never even recaptured the promotional costs." He added, "I have no confidence I would make a penny."
But with the help of his lawyer, Grant Smith, who also represents him in the Russia investigation, Stone negotiated a deal to write a new introduction and reprint the book with a new title.
On Jan. 13, Stone emailed Tony Lyons of Skyhorse Publishing to say he was putting "the final touches" on the introduction and it's "substantially longer and better than the draft sent to me by your folks."
Better or not, Stone's language in the introduction now risks violating the judge's gag order, which was tightened on Feb. 21.
It was only then that Smith began demanding more information about the book's release to figure out what to tell the judge.
"The mere publication of the new portions of the book could land Roger in jail for contempt of the judge's order," Smith wrote to the publisher on Feb. 26. "I need this immediately. This is not some made-up emergency."
Lyons told him that about 14,000 copies had been shipped across the country and an electronic version had already been made available online "long before the gag order."
"So we should be good, right?" Lyons wrote in an email.
"Hopefully," Smith responded.
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