Thrice-indicted former President Donald Trump seems intent on testing the rules that apply to tampering with witnesses and intimidating judges.

Despite being warned about such things, he shows no sign of slowing down, effectively daring the legal system to do something about it.

A week ago, Trump lodged a vague threat on his social media site Truth Social, writing, “IF YOU GO AFTER ME, I’M COMING AFTER YOU!” He also attacked his former vice president, Mike Pence, for Pence’s apparent testimony in the federal Jan. 6 case. And he baselessly accused a Georgia prosecutor of an affair with a gang member.

Republican presidential candidate former President Donald Trump speaks as he visits the Iowa State Fair on Aug. 12, in Des Moines, Iowa. Charlie Neibergall/Associated Press

Now, Trump has turned his attention to the judge who warned him about intimidation tactics, as well as a key witness in the Georgia case in which he faces possible indictment within days.

On Sunday afternoon, Trump promoted a post on his Truth Social platform that falsely accused the judge in the federal Jan. 6 case, Tanya Chutkan, of having “admitted she’s running election interference against Trump.” Later, Trump called Chutkan “highly partisan” and “VERY BIASED AND UNFAIR,” while citing comments from her purportedly backing up the “election interference” allegation.

Separately, Trump on Monday morning stated in a Truth Social post that a witness slated to testify before a Georgia grand jury this week, former Georgia lieutenant governor Geoff Duncan, a Republican, “shouldn’t” testify. Trump did so while faulting Duncan for not going along with Trump’s efforts to overturn the 2020 election.

The question, as it often is with Trump, is whether he has gone too far – and where the line is for those charged with determining where it is.

Experts say the situation could be coming to a head.

Trump made his comments about Chutkan after he was explicitly told to abide by limits on what he can say about the federal Jan. 6 case.

Trump signed a pretrial release form acknowledging that it would be a crime to “intimidate or attempt to intimidate a witness, victim, juror, informant, or officer of the court.” A judge is an officer of the court.

“This could be interpreted as an attempt to intimidate Judge Chutkan,” said Joshua Dressler, a law professor at Ohio State University.

But Dressler said he doubted that Chutkan would find Trump to be in violation, in part because it would train the focus of the proceedings on her.

“Beyond that, an attempt to intimidate requires proof that the actor (here, Trump) had the specific intent to intimidate,” Dressler said. “Trump, of course, can say that he is merely expressing his negative views about her, which he has every right to do, and that he is not attempting to intimidate her.”

Dressler’s comments track with Chutkan’s comments in court last week, in which she reserved most of her warnings for potential attempts to intimidate a witness or juror, rather than herself.

Trump’s attack also focused on Chutkan’s statements during a previous Jan. 6 case, in which she cited defendants’ “blind loyalty to one person who, by the way, remains free to this day.” But as Politico’s Kyle Cheney notes, Chutkan is hardly the only judge to offer such comments.

The rhetoric comes a week after Trump previously tested instructions regarding his pretrial release.

He made his “IF YOU GO AFTER ME, I’M COMING AFTER YOU!” comment less than 24 hours after a magistrate judge told him it would be “a crime to intimidate a witness or retaliate against anyone for providing information about your case to the prosecution.”

Trump both signed his pretrial release form and swore that he would comply with those instructions. A day after the above post, he turned his attention to disputing Pence’s alleged testimony that Trump told him he was “too honest” when he refused to try to overturn the election on Jan. 6, 2021.

The government has not accused Trump of attempting to intimidate witnesses, but it has cited these comments while seeking a protective order in the case. Chutkan last week ordered Trump and his lawyers to “take special care” to avoid intimidating witnesses and potential jurors.

“I will take whatever measures are necessary to safeguard the integrity of these proceedings,” she said.

Rather than explicitly threatening Trump with legal sanctions or a gag order, Chutkan instead suggested that such comments might create more urgency to go to trial quickly to ensure an impartial jury. That would run counter to the desires of the Trump legal team, which has pushed for a much later trial date than the one the government has called for.

Trump has yet to be indicted in the Georgia Jan. 6 case, and so no such instructions have been issued. But his comments regarding that case also appear to push the bounds of what it means to influence a witness.

“I am reading reports that failed former Lt. Governor of Georgia, Jeff Duncan,” Trump said, misspelling Duncan’s first name, “will be testifying before the Fulton County Grand Jury. He shouldn’t.”

Trump added: “I barely know him but he was, right from the beginning of this Witch Hunt, a nasty disaster for those looking into the Election Fraud that took place in Georgia. He refused having a Special Session to find out what went on, became very unpopular with Republicans (I refused to endorse him!), and fought the TRUTH all the way. A loser, he went to FNCNN!”

Georgia law makes it a crime “knowingly to use intimidation” with intent to “influence, delay, or prevent the testimony of any person” or “cause or induce” someone to “withhold testimony.”

The matter appears to turn on whether Trump intended to use intimidation, just as it does in the Chutkan example. Trump certainly has a long history of verbally attacking or otherwise guiding witnesses who could provide information against him.

Special counsel Robert S. Mueller III in his Russia investigation report focused on multiple examples of Trump’s conduct toward witnesses, while ultimately deciding it wasn’t his place to accuse Trump of obstructing justice, regardless of the evidence. When Trump attacked former Ukraine ambassador Marie Yovanovitch during her 2019 congressional testimony, she called it “very intimidating.”

Trump’s comments are also hardly the first to test the limits of what the legal system will permit with regard to his current legal jeopardy. In addition to his false claim about Chutkan, he has baselessly suggested drug use by special counsel Jack Smith and last week baselessly suggested that Fulton County, Ga., District Attorney Fani Willis had “an affair” with a “gang member.” (Willis is the prosecutor who may soon bring charges against Trump.)

Comments like that would normally pose significant problems for a defendant.

Former federal prosecutor Peter Zeidenberg said the situation with Trump, witnesses and Chutkan is unusual, in part because defendants are “normally scared to death about being preventively detained.” Trump, meanwhile, has made free speech and his supposed persecution a cornerstone of his public defense, and forcing him to stop could feed into his narrative.

“I would not be surprised for a hearing to be called by Judge Chutkan … in which she really admonishes Trump to his face,” Zeidenberg said. “After that, it is anyone’s guess how this could escalate.”