Just days ago, the judge overseeing former President Donald J. Trump’s prosecution on charges of seeking to subvert the 2020 election admonished him against violating the conditions of his release put in place at his arraignment — including by making “inflammatory statements” that could be construed as possibly intimidating witnesses or other people involved in the case.

But Mr. Trump immediately tested that warning by posting a string of messages on his social media website, Truth Social, that largely amplified others criticizing the judge, Tanya S. Chutkan.

In one post, written by an ally of Mr. Trump’s, the lawyer Mike Davis, a large photo of Judge Chutkan accompanied text that falsely claimed she had “openly admitted she’s running election interference against Trump.” In two other posts, Mr. Trump wrote, “She obviously wants me behind bars. VERY BIASED & UNFAIR.”

After eight years of pushing back at a number of institutions in the United States, Mr. Trump is now probing the limits of what the criminal justice system will tolerate and the lines that Judge Chutkan sought to lay out about what he can — and cannot — say about the election interference case she is overseeing. He has waged a similarly defiant campaign against others involved in criminal cases against him, denouncing Jack Smith, the special counsel who brought two federal indictments against him, as “deranged”; casting Fani T. Willis, the district attorney of Fulton County, Ga., as “corrupt”; and even singling out witnesses.

Some lawyers have said that if Mr. Trump were an ordinary citizen issuing these attacks, he would be in jail by now. The question is whether Mr. Trump will face consequences for this kind of behavior ahead of a trial.

“He is absolutely in my view testing the judge and testing the limits, almost daring and taunting her,” said Karen Agnifilo, who has a three-decade legal career, including as the chief assistant in the Manhattan district attorney’s office. Ms. Agnifilo added that Mr. Trump is so far benefiting from his status as a candidate for office, facing fewer repercussions from the judges in the cases than other vocal defendants might.

So far, Judge Chutkan has merely warned Mr. Trump against making “inflammatory statements” about the case or people involved with it, saying she would do what she needed to keep him from intimidating witnesses or tainting potential jurors.

She has also told Mr. Trump’s lawyers that she may be forced to agree with the government’s proposal to go to trial sooner than they like as a way to protect the jury pool.

Otherwise, her options range from ignoring Mr. Trump’s comments to finding him in violation of his conditions of release. That could entail punishing Mr. Trump by fining him or even by sending him to jail, a move that would be complicated not only by politics but also by the presence of his Secret Service detail.

Judge Chutkan has warned Mr. Trump against making “inflammatory statements” about the case or people involved with it.Credit…Administrative Office of the U.S. Courts, via Associated Press

Judge Chutkan made clear last week that the boundaries of Mr. Trump’s free speech rights, even as a political candidate, would have to give way to the rules of the court.

“Mr. Trump, like every American, has the First Amendment right to free speech, but that right is not absolute,” she said. The limits, she added, included obeying the release conditions imposed at his arraignment and following her protective order governing the disclosure of discovery evidence in the case.

“The fact that he’s running a political campaign currently has to yield to the orderly administration of justice,” she said. “And if that means that he can’t say exactly what he wants to say about people who may be witnesses in this case, that’s how it’s going to have to be.”

Steven Cheung, Mr. Trump’s communications director, scoffed at any suggestion that Mr. Trump might be testing the bounds.

“‘President Trump was right’ isn’t just a catchphrase, it is fact,” he said. “From the fake dossier to the debunked Mueller investigation to the Russia hoaxes to the impeachment scams to Hunter Biden’s laptop to Crooked Joe Biden’s shady foreign dealings, President Trump has been proven time and again he is the only person who will speak truth to power.”

For years, while he was investigated by the special counsel Robert S. Mueller III over whether his 2016 campaign conspired with Russia and for possible obstruction of justice, Mr. Trump repeatedly attacked Mr. Mueller and his team, as well as members of his own Justice Department. At one point, in late 2018, Mr. Trump retweeted an image with Mr. Mueller and the deputy attorney general, Rod J. Rosenstein, behind bars.

But at the time, the chances that Mr. Trump, as a sitting president, would face indictment were slim to none, and he conducted his behavior behind the shield of the White House. With a Justice Department legal opinion dating to the Nixon era concluding that a sitting president could not be indicted, Mr. Trump faced little risk.

Now, despite four criminal investigations and four indictments, Mr. Trump — the dominant front-runner for the Republican nomination — has continued with one of the moves he uses routinely: attacking someone he considers a threat. He and his advisers have argued it is his right as a candidate and his speech should not be curtailed because of that. (One of the few people Mr. Trump has not assailed in his cases is Judge Aileen M. Cannon of the Southern District of Florida, who oversees the classified documents case. Mr. Trump himself nominated Judge Cannon to her position.)

“The problem he has is anybody — testifying truthfully or not — who could ding him slightly or take him on frontally, is an adversary who has to be demolished,” said Ty Cobb, a lawyer who worked in the Trump administration during the Mueller investigation and saw firsthand how little regard Mr. Trump had for directions trying to curtail his behavior. “He doesn’t understand anything about the propriety of how to live a life. He’s at war perpetually — 24/7.”

William P. Barr, who was Mr. Trump’s attorney general, added, “Even as president, he would not keep his public comments about pending cases within proper limits.” This was so pronounced during the presidency that Mr. Barr publicly said Mr. Trump’s tweets about his convicted adviser, Roger J. Stone Jr., were making it “impossible” for Mr. Barr to do his job.

One of Mr. Trump’s lawyers in the case before Judge Chutkan, John F. Lauro, acknowledged that trying to change Mr. Trump’s behavior was unlikely.

“With President Trump, because of the campaign and I would say because of his personality, it’s impossible for him not to speak out on the issues. So it does present unique circumstances,” Mr. Lauro said on a recent podcast with the lawyer David Oscar Markus, which was recorded days before the hearing with Judge Chutkan. “My approach as a lawyer is obviously very different than his as a candidate. But he feels strongly that he needs to speak out. And he also in particular looks at this prosecution as a political prosecution. So as a result I think in his mind it’s sort of fair game from a political perspective to make these comments.”

Even before Mr. Smith was appointed special counsel, Justice Department officials worried that Mr. Trump would stress-test the judicial system if he was ever charged. Prosecutors had little doubt Mr. Trump would castigate them, along with witnesses and judges, to vent his anger, but also as part of a strategy of dragging opponents into a brawl over what he could and could not say to bolster his claim that the department was seeking to muzzle and destroy him.

In pointing to the more lenient treatment afforded to Mr. Trump, Ms. Agnifilo cited Sam Bankman-Fried, the cryptocurrency entrepreneur who recently had his pretrial release agreement revoked after a judge found that he had engaged in witness intimidation.

“Trump is clearly being treated differently,” Ms. Agnifilo said. “I’ve never seen a defendant being treated the way Trump has been treated in my 30-year career.”

It is not uncommon for defendants to have their bail revoked for disobeying the conditions of their release by taking drugs or committing other crimes. It is also not uncommon for defendants to be jailed for intimidating witnesses in their case like Mr. Bankman-Fried.

But it is uncommon for defendants to be punished for making inflammatory statements about judges or prosecutors if only because they are typically given warnings before penalties are issued and tend to heed those warnings. And in the case of Mr. Trump, he is a defendant who is also a political candidate who faces two prosecutions involving the administration of one of his opponents.

As a grand jury in Georgia prepared to indict Mr. Trump on Monday in the state investigation into his efforts to cling to power, he suggested on Truth Social that former Lt. Gov. Geoff Duncan “shouldn’t” testify despite being subpoenaed.

“Straight up telling a subpoenaed witness not to testify — that’s not kosher,” Mr. Cobb said.

At a hearing on Friday, Judge Chutkan suggested she would need to see a motion, filed by Mr. Smith, before taking any actions to hold Mr. Trump accountable for statements he has made on social media — although in theory she could act on her own. The special counsel’s office, in previous legal filings and statements in court, has made clear that it is closely monitoring Mr. Trump’s public statements.

Mr. Lauro expressed concern at the hearing that the various restrictions could unfairly keep Mr. Trump from giving voice to full-throated political arguments on the campaign trail. He even suggested that limiting what Mr. Trump could say about the case would “provide an enormous advantage to President Biden in the middle of a campaign.”

The judge seemed unpersuaded.

Samuel W. Buell, a law professor at Duke University and a lead federal prosecutor in the Justice Department’s case against Enron, said that even if Mr. Trump’s most recent messages about Judge Chutkan — ones in which he merely reposted messages from others — did not cross the line themselves, the former president was clearly pressing the boundaries of antagonizing the judge.

Mr. Trump is “walking the line” in a way “to make it difficult for her, never giving a single, clear example that can be used as a basis for ruling, but always continuing to push the envelope,” he said.

Glenn Thrush contributed reporting.

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