It took Donald Trump less than 24 hours to test the boundaries of Judge Juan Merchan’s gag order in his New York criminal trial.

In two posts on his Truth Social account, the former president attacked Merchan for issuing the gag order – and he went after the judge’s daughter for her liberal political work, exploiting the ambiguous language in the order that didn’t explicitly forbid discussion of Merchan’s family.

On Monday, Merchan pushed back, expanding the gag order to cover his family – though the judge remains fair game for Trump – and attempting to limit Trump’s vitriol two weeks before the trial is set to begin.

Merchan’s need to issue a second gag order highlights the significant and unique challenge that Trump poses for the judge overseeing the unprecedented first criminal trial in US history of a former president and current presidential candidate.

In the past six months, Trump has sat in a half-dozen different courtrooms before judges overseeing his four criminal and two of his civil cases, along with a federal appellate court. A CNN review of Trump’s appearances shows how the former president has taken repeated steps both inside and outside the courtroom to test the limits of judges – and the judicial system – trying to rein him in.

“He really pushes the boundaries. He walks up to the line and doesn’t quite cross the line, but he stomps on it – and in essence, taunts the court,” said Karen Friedman Agnifilo, a CNN legal analyst and former prosecutor in the Manhattan district attorney’s office.

Inside the courtroom, Trump has been admonished and threatened with removal for being disruptive. He’s testified twice, once delivering repeated rants mimicking his campaign speeches, and another time confined to a tightly scripted, three-minute affair. He’s walked out during an opposing lawyer’s closing argument. In another case, he delivered part of his own lawyers’ closing argument against the judge’s explicit instructions.

Outside the courtroom, Trump has repeatedly railed against the charges he faces in front of cameras and attacked all of those involved on social media.

Trump’s attacks against Merchan went so far as to draw a rare rebuke from a sitting federal judge last week.

“It’s very disconcerting to have someone making comments about a judge, and it’s particularly problematic when those comments are in the form of a threat, especially if they’re directed at one’s family,” US District Judge Reggie Walton told CNN’s Kaitlan Collins on “The Source.”

‘You have to set boundaries’

The two judges who have had Trump as a defendant in their courtroom the past six months used different tactics to try to rein him in.

Judge Arthur Engoron, who oversaw New York Attorney General Letitia James’ civil fraud case, was often visibly agitated with Trump’s antics and issued a gag order, but also let the former president have his say.

Trump would leave the courtroom at nearly every break and stop at cameras outside, criticizing the New York attorney general, her case and the judge overseeing it. Trump would extend his complaints to social media, including going after Engoron’s clerk shortly after the trial began. Engoron issued a gag order on commentary about court staff that covered his clerk, fining Trump twice for breaking it.

When Trump testified at the trial, he delivered political speeches instead of answering questions, a routine that quickly exasperated Engoron, who threatened to have Trump removed as a witness for being non-responsive.

But Engoron then changed tactics, sitting back and not interrupting Trump’s political missives while the attorney general’s lawyer slogged through questions to Trump. Engoron also let Trump briefly speak in court during closing arguments – even though he’d already rejected a formal request – where the former president gave a five-minute speech before Engoron finally cut him off.

Judge Lewis Kaplan, by contrast, kept stricter control of Trump and his attorneys during the federal E. Jean Carroll defamation case, at one point threatening to remove Trump when he was being disruptive during Carroll’s testimony.

Merchan’s courtroom demeanor falls somewhere between Engoron and Kaplan, according to lawyers who have appeared before the judges.

“The judge is going to have a discipline issue on his hands throughout this trial, the same way a parent has to struggle sometimes … with disciplining children,” said Elie Honig, a CNN senior legal analyst and former prosecutor. “You have to set boundaries, and you have to enforce them.”

Trump has appeared three times before Merchan since he was indicted a year ago by the Manhattan district attorney, who charged him with 34 counts of falsifying business records over the reimbursement of hush money payments made to adult film star Stormy Daniels before the 2016 election. Trump has pleaded not guilty and denies having an affair with Daniels.

Merchan, 61, has been a judge in New York city’s criminal court since 2009. He has overseen cases already involving the Trump Organization and its former chief financial officer Allen Weisselberg.

Agnifilo, who appeared in Merchan’s court dozens of times when she was a prosecutor, described him as a “judge’s judge” who keeps a professional distance and doesn’t inherently favor the prosecution or the defense.

“He’s not chit-chatty or someone who pals around with anybody,” Agnifilo said. “He’s sort of mild-mannered and professional in the best possible way. At the same time … he will absolutely do what’s necessary to make sure that the trial goes efficiently, smoothly and fairly.”

‘Threatening, inflammatory, denigrating’

Trump’s social media posts are often an issue, especially given security concerns.

In Trump’s federal election subversion case, Judge Tanya Chutkan, who has faced death threats and had her security increased last year, issued a partial gag order similar to Merchan’s.

“Even amidst his political campaign, Defendant’s statements pose sufficiently grave threats to the integrity of these proceedings that cannot be addressed by alternative means,” Chutkan wrote.

Merchan’s opinions limiting Trump’s speech pointed to the comments he’s made in all of his cases, citing Trump’s “threatening, inflammatory, denigrating” statements toward those involved.

“It is no longer just a mere possibility or a reasonable likelihood that there exists a threat to the integrity judicial proceedings. The threat is very real,” Merchan wrote on Monday.

Trump responded, as he so often does, with a post on Truth Social Tuesday morning attacking the judge, which is still allowed under Merchan’s order.

“This Judge should be recused, and the case should be thrown out,” Trump wrote. “There has virtually never been a more conflicted judge than this one.”

Trump has not gone after the judges in his other two criminal cases. In the federal classified documents case, Trump has appeared several times before Judge Aileen Cannon, whom he appointed. Trump has not yet been in court with Georgia Judge Scott McAfee in the Fulton County racketeering case, where a potential trial would be televised, unlike the other three criminal cases.

‘You just can’t control yourself’

Unlike Engoron, who was overseeing a bench trial in the civil fraud case, Kaplan had to be cognizant of the jury during the second Carroll defamation case in January.

As a result, Kaplan kept a tight rein on all of the attorneys and Trump. He was quick to admonish them if they stepped out of bounds and at one point threatened to remove the former president from the courtroom if he interrupted the trial after Carroll’s attorneys complained they could hear Trump muttering at the defense table that the case was part of a witch hunt.

The judge advised Trump to control himself, saying he could forfeit his right to be in the courtroom if he continued.

“I hope I don’t have to consider excluding you from the trial or at least from the presence. I understand you’re probably very eager for me to do that,” Kaplan said.

“I would love it,” Trump shot back.

“I know you would. You just can’t control yourself in these circumstances, apparently,” Kaplan responded.

The discussions over Trump’s testimony at the defamation trial were also wrapped in tension.

Before trial, the judge limited what Trump would be able to testify about – including denying that he raped Carroll. Kaplan ruled that Trump could not try to relitigate the prior case, which he chose not to attend, where a jury found Carroll proved Trump had sexually assaulted her.

Trump was on the stand for less than three minutes, but the judge negotiated the precise questions and answers for at least 10 minutes beforehand.

“I want to know everything he is going to say,” Kaplan said.

In the middle of that discussion, before the jury was brought in, Trump raised his voice and said unprompted, “I never met the woman. I do not know who this woman is. I wasn’t at the trial.”

Once on the stand, Trump answered the questions and stopped abruptly when the judge cut him off. When Carroll’s attorneys tried to ask Trump questions about the first trial he did not attend, his lawyers objected. Trump turned toward the jury and shook his head from side to side.

Trump did not make ancillary comments while the jury was in the courtroom, but he had one more protest to make. Less than five minutes into Carroll’s lawyer’s closing argument, he abruptly walked out of the courtroom. The judge briefly stopped Carroll’s lawyer to note for the record that Trump had left.

Less than seven hours later, a jury returned a whopping $83.3 million verdict against Trump for defaming Carroll.