Even before his Monday afternoon Instagram post, Roger Stone was already shaping up to be anything but a conventional defendant. | Andrew Caballero-Reynolds/AFP/Getty Images Legal ‘He’s on edge’: Roger Stone silencing expected after barbed comments Even Stone’s friends expect a sweeping gag order after a Monday social media post criticizing the judge overseeing Stone's fight against Robert Mueller's charges.

Roger Stone scored a small legal victory last Friday, but it took him only four days to blow it.

Now, even Stone’s friends expect the longtime Donald Trump associate to get hit with a sweeping gag order preventing him from commenting about his case on Thursday at an emergency hearing in Washington that the judge called after him posting a threatening message about her on Instagram.


There’s even a worst case scenario in which District Court Judge Amy Berman Jackson sends the self-proclaimed GOP dirty trickster to jail.

That’s the reality the 66-year-old Stone faces despite his attempts to walk back a Monday afternoon social media post that complained about “Deep State hitman Robert Mueller” and the “Obama appointed Judge” — and featured an image of Jackson with what looked like crosshairs in the corner — by deleting the message and then issuing Jackson a formal apology.

His post came less than 100 hours after Jackson decided to limit Stone’s commentary only while he was at the courthouse — widely perceived as a win for Stone at the time.

“He’s on edge. Roger probably needs to be slapped on the wrist,” said Tyler Nixon, a longtime friend and counsel to Stone.

Stone, whose barbed commentary has been tied to fundraising pleas, is “learning the contours of what he can get away with saying and legitimately raise money for his defense and frankly protest what he legitimately believes to be a miscarriage of justice in his prosecution,” Nixon said.

“It’s a fine line and I’d hope the judge will enable him to make the couple mistakes and take it seriously,” he added.

But it’s not clear Jackson will give Stone any more chances.

Jackson, an appointee of President Barack Obama, has earned a no-nonsense reputation in the Mueller probe cases she has overseen, including charges against former Trump campaign chairman Paul Manafort and Rick Gates, Manafort’s campaign deputy. In that case, she slapped a gag order on Manafort and Gates, as well as their attorneys, just days after Mueller’s initial indictments were filled. She later sent Manafort to jail after the special counsel accused him of witness tampering — that’s where the 69-year old longtime GOP operative has remained ever since.

The judge has a wide latitude in terms of how to deal with Stone. Jackson can give him a stern warning or impose the same kind of restrictive gag order that she issued Friday for Mueller's and Stone’s lawyers — but not for Stone himself — and potential case witnesses. She also could impose restrictions on Stone like requiring him to wear a GPS monitoring device or limiting his travel — Jackson already has set parameters that require him to get the court’s permission to venture beyond South Florida, New York or the D.C. region. A fine or jail aren’t out of the question either.

“The gag order may be the lesser of his eventual problems if it turns out that when they investigate his conduct the prosecutors could decide that that constitutes an effort to intimidate or threaten the judge,” said Shanlon Wu, a defense attorney who previously represented Gates.

A spokesperson for the U.S. Marshals Service said the department responsible for protecting federal judges is aware of the threat Stone allegedly made against Jackson. But it declined to discuss any specific threats or how it protects judges.

Even before his Instagram post, Stone was shaping up to be anything but a conventional defendant. He’s spent the weeks since his indictment last month going on national television and doing interviews from his South Florida driveway. In court, his lawyers have filed motions objecting to Jackson’s assignment to their case and accusing Mueller of releasing Stone’s indictment before it had secured court approval.

Stone’s legal strategy, his friends and allies say, was born after observing Manafort’s legal strategy.

“Roger watched other people defend themselves quietly and lose,” said Michael Caputo, a former Trump 2016 campaign adviser and longtime Stone friend who has been questioned in the Mueller investigation. “He’s made the conscious decision to speak loudly and clearly about his innocence throughout the entire process.”

Mueller’s team indicted Stone late last month on charges of lying, obstruction of justice and witness tampering — crimes that could get him more than four years in prison if he is convicted. Preparing for trial, the special counsel’s prosecutors had sought a gag order on Stone out of fear his comments would affect the fairness of a trial.

Stone’s latest predicament is of his own making. The image of Jackson posted on Instagram on Monday seemed to feature crosshairs in the corner. Others noted that the picture came from a conspiracy theory website that has an anti-Jewish perspective.

He later deleted the photo and posted a version without crosshairs. By the end of the evening, though, Stone had deleted that photo, as well, and his lawyers submitted an apology to the court.

“Please inform the Court that the photograph and comment today was improper and should not have been posted,” Stone wrote in Monday night’s court filing. “I had no intention of disrespecting the Court and humbly apologize to the court for the transgression.”

In an email to POLITICO, Stone said he would attend Thursday’s hearing as ordered.

“I have no further comment at this time,” he wrote.

One of Stone’s lawyers, Bruce Rogow, said he’d also be in attendance Thursday but did not answer a question about a potential shakeup on Stone’s legal team in the wake of Monday’s incident. Two other Stone attorneys didn’t respond to requests for comment, though both are restricted from speaking about the case under the gag order.

In interviews on Tuesday, Stone’s friends chalked up the Instagram post to a mistake that’s been widely misinterpreted by the media as an attack on the judge. They say Stone was trying to get across that Jackson was appointed by Obama.

“That’s what he wanted to get across. But it can certainly be interpreted differently,” said Annemarie McAvoy, another attorney who was on Gates' defense team. “That’s why as an attorney you want the client to only speak through you or with close supervision.”

Stone needs to come to terms with the fact his every move is being scrutinized and could be used against him, Nixon said.

“I’m not going to defend what was put up. My advice is not to have done that,” he said. “There’s an adjustment period Roger is having to get used to.”

Wu, a former federal prosecutor, predicted Stone would eventually recognize the legal peril he faces by excessively commenting on his own case. “He might kick and fuss a little bit in the beginning but once he gets a whiff of reality he’s going to cave,” Wu said. “I don’t think he’s going to show himself to be some sort of warrior for a First Amendment cause.”

Others doubt whether Stone would ever take his lawyers’ advice and stop discussing the case. McAvoy said Jackson’s initial ruling Friday set up Stone for the legal morass he’s now in.

“She gave him just enough rope to get himself into trouble,” she said. “I don’t know if he’s capable of keeping his mouth shut. It’s just not in his personality and it’s very hard to force someone to change his personality.”

Jackson on Friday signaled she’d be keeping close tabs on Stone, noting that while her initial order allowed him to keep talking about the case, she retained the power to amend her order “if necessary.” She also warned Stone that any excessive public comments could come back to bite him if he complained later on about excessive pretrial publicity that he himself caused.

In the longer term, McAvoy said Stone should be mindful that has publicly targeted the judge who would be sentencing him if he ends up pleading guilty or a jury convicts him on Mueller’s charges.

“She’s not going to forget that,” McAvoy said. “There’s a fine line between an aggressive defense and upsetting the judge to the extent that you then have payback from the judge during sentencing.”