A judge could toss Trump in jail. The question is whether one dares.

Donald Trump in a 2016 debate infamously warned Hillary Clinton that, if he were president, “you’d be in jail.” A little more than seven years later, he appears bent on challenging judges who actually have the power to land him there himself.

But could it really get to that point? There is little question judges will seek to exhaust other options, but there is also increasingly little question Trump will continue to test their resolve with his attacks on judges, prosecutors, witnesses and others.

And his current and former allies appear to be girding for the likelihood of this tug-of-war with the judges escalating. One is even predicting Trump will go to jail. The former president has in recent weeks responded to a pair of limited gag orders with his typical defiance and provocation.

A judge in his New York civil case has fined Trump twice, for a total of $15,000, over his attacks on a law clerk. The Trump team initially left a post on his campaign website that violated the gag order. Then Trump made veiled comments the judge ruled had referred to the clerk.

In his federal election interference case, Trump responded to a judge pausing another limited gag order by issuing comments that would transparently have violated it had the pause not been in effect. When the judge reinstituted the gag order this week, Trump seemed to quickly violate it by attacking a potential witness, his former attorney general William P. Barr.

The Trump campaign told The Washington Post that Trump had not been aware the gag order had been reimposed when he called Barr “dumb,” “weak” and “gutless” on Truth Social on Sunday night. But the post remained live as of Wednesday morning, two and half days later.

What unites all of these instances is, to be charitable, a distinct lack of care on the part of Trump when it comes to abiding by the limits placed on his speech. You could certainly be forgiven for thinking Trump is being intentionally provocative and defiant. He has throughout his political career sought to exploit plausible deniability, sending coded messages to his base to say things without explicitly saying them.

New York Supreme Court Justice Arthur Engoron has wagered that is precisely what happened in the case over which he is presiding. He barred Trump from attacking his staff, and Trump proceeded to attack the judge and “a person who is very partisan sitting alongside him.” The clerk sits right next to Engoron.

Trump was called to the stand and claimed he was talking about his former lawyer, Michael Cohen, who had been serving as a witness near the judge. The judge rejected this claim, calling the explanation from Trump “not credible” and noting that Trump otherwise had no problem invoking Cohen by name. Engoron, in initially fining Trump for violating the gag order, warned that penalties could include “holding Donald Trump in contempt of court, and possibly imprisoning him.”

Current and former Trump allies seem to acknowledge where this could be headed. While appearing on Newsmax on Tuesday, Trump lawyer Alina Habba was asked about his potentially being jailed for violating gag orders. She insisted it is not something his legal team had given much thought to, while offering the kind of answer that suggests they had indeed. (She suggested the Secret Service might prevent his jailing.)

Fox News host Jesse Watters on Tuesday devoted a whole segment on the prospect of Trump being jailed, while saying, “Do you think Donald Trump is going to respect a gag order? He does not see a gag order as a threat. He sees it as a challenge.”

Former Trump White House lawyer Ty Cobb on Monday outright predicted Trump would land in jail. Cobb said on CNN, “Ultimately, I think he’ll spend a night or a weekend in jail.” He added, “I think it’ll take that to stop him.” Cobb certainly has experience in dealing with Trump. Other lawyers who have served Trump have also hinted broadly their client could be unwieldy at best.

Earlier this year, Trump lawyer Joe Tacopina had acknowledged an “ill-advised” Trump social media post featuring a picture of Trump holding a baseball bat next to a picture of a prosecutor. “I’m not his social media consultant,” Tacopina said.

Another Trump lawyer, John Lauro, has alluded to the fact that Trump does not always follow advice with his public comments. “To the extent that I can make any appropriate suggestions to a client, I do. But as we know,” Lauro said, “sometimes clients follow our suggestions, sometimes they don’t.”

Should that continue to be the case, with Trump challenging or outright flouting gag orders, judges have a number of options. The simplest option is one we have already seen: escalating fines. Trump is wealthy, but this would seem to be the most readily available tool, and Trump previously complied after Engoran fined him $110,000 for defying a subpoena. Whether such fines would be as compelling with Trump facing criminal conviction and a potential prison sentence is very much an open question.

Catherine Ross, an expert on gag orders at George Washington University, suggested a judge could also confine Trump to an apartment or house without social media. “That would be gentler than prison, but with many of the same restrictions,” she said.

Again, this would be dicey given that it would prevent Trump from traveling for his campaign. Another drastic but potentially compelling option would be threatening to expedite a trial. The federal election interference case in which Trump faces a limited gag order is set for March.

The Trump team has sought to move it to a much later date, and holding it earlier could place it in the heart of the early presidential contests. But this would not only feed into his allegations that these trials are timed to hurt him politically, it could also feed the claim that his legal team was not given sufficient time to mount a robust defense.

Obama administration attorney general Eric Holder suggested recently the judges could move to restrict access to social media. But the idea that Trump would literally be barred from a preferred method of speech could be problematic practically and also potentially lead to public backlash.

Holder, in the same interview this week, played up the other options and, unlike Cobb, downplayed the idea that the former president would ever go to jail, even as he agreed that an ordinary person would indeed be facing such a sanction.

“I would be extremely reluctant to take a person who is a former president, the leading candidate of one of our major parties, and put him in jail,” Holder said. Judges likely will be too. But Trump has a talent for forcing people into unavoidably horrible decisions they would rather not have to make.