Stone is set to appear Thursday in front of federal Judge Amy Berman Jackson -- just a day after she sentenced his former lobbying colleague Paul Manafort to prison -- for a status hearing that was initially set to hash out pretrial issues and potentially set a trial date.
But Stone's behavior in recent weeks testing the limits of his gag order after he and his attorney plotted a book publicity tour could also dominate the morning's proceedings. The judge is clearly unhappy with him about the book's availability, and has told him he's crossed a line that she already warned him should not be crossed.
Jackson, who's been through situations like this before in Manafort's case, hasn't yet told Stone the consequences, if any. She may on Thursday.
Stone, President Donald Trump's longtime political adviser, was arrested in a predawn raid at his Florida home in January. He pleaded not guilty to obstruction, lying to Congress and witness tampering, and was released on bail.
While he was initially allowed to speak publicly about his case, Jackson slapped Stone's case with an expected but limited gag order. Minutes before it came in on February 15, Stone realized that a new introduction to his book, which was already available through booksellers, critiqued special counsel Robert Mueller and could irk the judge.
Over Presidents Day weekend, Stone promoted the book online, and also posted a threatening photo of the judge with crosshairs over her shoulder on Instagram. She quickly demanded that he come from his home in Florida to court in Washington, and she gave him strict orders on February 21 not to speak about his case, the court or Mueller again while his charges are pending. In the hours and days after that hearing, Stone's legal team debated how the book might fit with the revised, stricter gag order. They hadn't raised the issue with her at the hearing.
"Any violation of this order will be a basis for revoking your bond and detaining you pending trial," Jackson told Stone when she set the stricter gag order. "So I want to be clear: Today I gave you a second chance. But this is not baseball. There will not be a third chance."
Stone's team then waited a week to inform the court of the paperback release of his book about President Donald Trump's election.
"I now find myself on Crooked Special Prosecutor Robert Mueller's hit list because I've advised Donald Trump for the past forty years," Stone says in the new introduction, written this year before his arrest. "Clearly, I was targeted for strictly political reasons."
Jackson so far has slammed Stone's team for failing to tell her about the book sooner and suggested its belated court filing appeared designed to drive book sales -- which have been minimal, according to emails from the publisher.
"There is no question that the order prohibited and continues to prohibit the defendant from making any public statements, using any medium, concerning the investigation," Jackson wrote to Stone last week, after his legal team first told her about the book's availability. "Any costs or consequences that will be occasioned by the court's reiteration of this clear requirement at this late date are also solely attributable to the defendant."
Responding to the court on Monday, Stone's team said it would have been "a bit awkward" to mention the book during the gag order hearing. The legal team insisted that Stone never intended to violate the gag order or hide the book release from Jackson. "Having been scolded, we seek only to defend Mr. Stone and move ahead without further ado," they wrote.
Still, emails from February between Stone's attorneys and his publisher revealed their concern that Jackson could decide to throw Stone behind bars for violating the gag order.
"The mere publication of the new portions of the book could land Roger in jail for contempt of the judge's order," wrote Grant Smith, one of Stone's attorneys, in an email that his legal team included in its latest filing to the judge.
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