Donald Trump currently has two gag orders against him, but one of them is currently stayed while the appeals process plays out.
Former Acting Solicitor General Neal Katyal believes that it is only a matter of time before Trump upsets these judges enough that he winds up in jail.
Trump now has two gag orders that he is facing, one by Judge Chutkan in the January 6 case and another by Judge Ergonon in the New York fraud case.
The gag order played by Judge Chutkan is being appealed, so Judge Chutkan has agreed to stay the order until the appeals process plays out.
The other gag order, which was actually the first one imposed on Trump, was done after Trump commented on social media about Judge Engoron's clerk.
Trump posted on Truth Social that she was Senator Chuck Schumer's (D-N.Y.) girlfriend. Trump had referred to his post when discussing the case with the media, asking if they saw what "they" were saying about the clerk.
Judge Engoron was livid, slapping the gag order on Trump and demanding the post be taken down, which it was.
However, Trump kept it up on his campaign website, which is when Engoron fined him $5,000.
Trump was then hit with a $10,000 fine for additional comments that Engoron perceived as being about his clerk again, which would violate the gag order. Trump insisted he was talking about Michael Cohen, but Engoron did not believe him and issued the fine.
At that time, Engoron also told Trump that any future violations could result in much stiffer penalties, including jail time.
Katyal slammed Trump while appearing on MSNBC's "Inside" this weekend.
He used Trump as a perfect example as to why gag orders are put in place.
"There are two different gag orders. One, Trump has already violated, the one in New York state, in which he has been now find twice. And then there's a swarm that you're talking about the federal level with Jack Smith. And that one has been put on pause.
"I think Donald Trump has made the best case of anyone. He is witnessing for why you need the gag order in effect. Because the moment that gag order was put on pause, he started developing and attacking people left and right."
Katyal went on to say that he believes that not only will the second order continue to be enforced, but he believes that Trump will continue to violate the gag orders, which could possibly put him in jail, something that Judge Engoron has already threatened.
"So, I think that there is no doubt in my mind that there will be a gag order imposed on Donald Trump. And there also is no doubt in my mind that he is going to violate it repeatedly. Repeatedly to the point where a judge is going to have to confront the ultimate question, are we going to put the former president in jail? and I think there is only one answer to that."
Former Biden Press Secretary Jen Psaki, who was hosting the show, prodded Ketyal for the answer to that question.
"Which is you have to. If he continues this behavior, no other litigant in this country would ever be able to do what he is doing. Judges, I don't care what your politics are, the one thing you understand when you put out that robe is that it is about the legitimacy of the court and about the judicial process."
After the $10,000 fine was issued to Trump and Engoron put him on notice, there was much debate about how much further Trump would be willing to go before zipping his mouth.
My opinion is that he will continue to poke this bear, actually hoping that he gets tossed in jail.
Trump's donors have responded to Trump's indictments by flooding his campaign with money, so the natural thought process is that they will do the same if he is seen being taken away in cuffs.
Legally speaking, however, Trump will be doing himself no favors because most of these cases are doomed at the lower court levels.
If Trump is going to beat these cases, for the most part, it will have to be on appeal, so I think he would be better served to sit on his hands, allow these cases to play out, and not give prosecutors more ammo to use against him when the cases finally do end up in appeals court or even get escalated to the Supreme Court, which is almost a certainty considering the unprecedented nature of these cases.