JUST MOMENTS AGO THAT TRUMP DID IN FACT VIOLATE THE GAG ORDER NINE TIMES. AND FINING HIM $1,000 FOR EACH OF THE VIOLATIONS. LET'S BRING IN NBC NEWS CORRESPONDENT VAUGHN HILLYARD, FORMER PROSECUTOR CHARLES COLEMAN, AND ATTORNEY AND LOYOLA LAW SCHOOL PROFESSOR JESSICA LEVINSON. VAUGHN, LET'S START WITH THE GAG ORDER. BRING US ALL THE DETAILS. >> Reporter: THE DISTRICT ATTORNEY'S OFFICE, ANA, BROUGHT FORWARD TEN DIFFERENT ALLEGATIONS OF SOCIAL MEDIA POSTS MADE BY DONALD TRUMP OVER THE COURSE OF TWO WEEKS THAT THEY ALLEGED VIOLATED THE GAG ORDER AGAINST HIM THAT BARRED HIM FROM ATTACKING POTENTIAL WITNESSES AS IT PERTAINED TO THESE CRIMINAL PROCEEDINGS AS WELL AS JURORS OR POTENTIAL JURORS. AND OF THOSE TEN ALLEGATIONS BROUGHT FORWARD BY THE DISTRICT ATTORNEY, NINE OF THEM WERE FOUND BY JUDGE MERCHAN TO HAVE VIOLATED THE GAG ORDER PLACED ON DONALD TRUMP. IN HIS SEVERAL PAGE ORDER, JUDGE MERCHAN WRITES THAT DONALD TRUMP WILLFULLY VIOLATED THE ORDERS, NOT ONLY ATTACKING POTENTIAL WITNESSES, STORMY DANIELS AND MICHAEL COHEN, BUT ALSO BY DISCUSSING THE JURY AND THE IMPLICATION THAT TO A CERTAIN EXTENT THERE COULD HAVE BEEN INDIVIDUALS WHO WERE TRYING TO MAKE THEIR WAY ON TO THIS JURY IN AN EFFORT TO TAINT THEM. LIBERAL ACTIVISTS THAT THEY WERE REFERRED TO. THE JUDGE DETERMINED THAT REPOSTS BY DONALD TRUMP, SOME OF THOSE VIOLATIONS WERE IN FACT STATEMENTS MADE BY DONALD TRUMP. AND THAT HE WAS NOT CLOAKED WITH SOME PROTECTION BECAUSE HE WAS SIMPLY REPOSTING THEM, BUT BY DOING THAT ACT, HE THEREFORE WAS AFFIRMING THE CONTENT OF THOSE VERY POSTS. AND NOW THIS IS NOTABLE. NUMBER ONE, 9:30 A.M. EASTERN TIME, THIS UPCOMING THURSDAY, THERE IS ANOTHER HEARING ABOUT POTENTIAL OTHER VIOLATIONS THAT THE D.A.'S OFFICE ALLEGES DONALD TRUMP HAS VIOLATED. AND AS YOU NOTED, EACH FINE WAS JUST $1,000 FOR EACH OF THE VIOLATIONS. AND JUDGE MERCHAN IN HIS ORDER MADE IT CLEAR THE COURT IN THE STATE OF NEW YORK DOES NOT HAVE THE DISCRETION TO INCREASE THAT FINE AMOUNT AND NOTING THAT SOMETIMES THE INDIVIDUAL, WHO IS FOUND TO BE HELD IN CONTEMPT, PERHAPS A $1,000 FINE DOES NOT HAVE THAT MUCH CONSEQUENCE TO THAT INDIVIDUAL. DONALD TRUMP NAMELY ONE OF THOSE INDIVIDUALS. AND THAT IS WHERE IN THE LAST LINE OF HIS ORDER, HE VERY EXPLICITLY WRITES HERE, QUOTE, BECAUSE THIS COURT IS NOT CLOAKED WITH SUCH DISCRETION, IT MUST THEREFORE CONSIDER WHETHER IN SOME INSTANCES JAIL MAY BE A NECESSARY PUNISHMENT, SENDING AN EARLY SIGNAL THAT HE IS AT LEAST CONSIDERING IF DONALD TRUMP WERE TO CONTINUE WILLFULLY VIOLATING THIS GAG ORDER, THAT HE WOULD CONSIDER JAIL TIME FOR DONALD TRUMP AS THIS COURTROOM AND ITS JURY AND THE PROSECUTION AND THE DEFENSE TEAM MOVES FORWARD AND PROCEEDS THEIR WAY THROUGH THIS TRIAL. >> JESSICA, JUST GETTING YOUR INITIAL REACTION TO THIS RULING. >> MY INITIAL REACTION IS THAT THIS IS A JUDGE WHO IS SERIOUS ABOUT IMPOSING GAG ORDERS AND VIOLATING GAG ORDERS. AND I THINK THIS IS FRANKLY EXACTLY RIGHT. IF YOU LOOK AT THOSE SOCIAL MEDIA POSTS, IF YOU LOOK AT THE REPOSTS AND IF YOU COMPARE THOSE TO WHAT WAS PROHIBITED UNDER THE GAG ORDER, I THINK IT MAKES ALL THE SENSE IN THE WORLD THAT THE JUDGE WOULD SAY THERE IS A VIOLATION HERE. I THINK WE HAVE SEEN FROM THE VERY BEGINNING THAT THIS IS A JUDGE WHO IS SERIOUS ABOUT CONTROLLING HIS COURTROOM, WE SAW THAT IN TERMS OF THE PACE OF JURY SELECTION, WE HAVE SEEN THAT AGAIN WITH RESPECT TO THE IMPOSITION OF THE GAG ORDERS, AND, YOU KNOW, WITH RESPECT TO THE COMMENT BY THE JUDGE THAT SOMETIMES THAT MONETARY PENALTY ISN'T ENOUGH TO GET SOMEBODY'S ATTENTION, SO THERE IS ALWAYS JAIL TIME, ON THE ONE HAND, THAT DOES SEEM BIG AND SIGNIFICANT, ON THE OTHER HAND, I WILL SAY, THOSE ARE THE ONLY TWO OPTIONS FOR A GAG ORDER, RIGHT? IT IS PAY MONETARY PENALTIES AND TAKE THE THING DOWN OR TAKE THE THING BACK IF YOU CAN, AND IT IS JUST, I THINK, REALLY A REMINDER THAT JAIL TIME IS ALWAYS A POSSIBILITY HERE. >> AND, CHARLES, WE SHOULD NOTE THERE WERE TEN INITIAL ALLEGATIONS OF VIOLATIONS. THE JUDGE CLEARLY LOOKED AT EACH ONE INDIVIDUALLY, DECIDED ONE OF THOSE DIDN'T AMOUNT TO A VIOLATION OF THE GAG ORDER, THE NINE OTHERS DID. HE TOOK A WEEK TO BRING THIS RULING. SO, HE APPEARS TO HAVE BEEN VERY, VERY CALCULATED AND THOUGHTFUL ABOUT WHAT HE WANTED TO HAND DOWN HERE. HE INSTRUCTED TRUMP TO REMOVE THE POST THAT HE FOUND IN VIOLATION BY 2:00 TODAY. CAN'T IMAGINE THIS IS GOING OVER VERY WELL WITH THE FORMER PRESIDENT. >> NO, ANA, BUT AT THE SAME TIME, I REALLY FEEL LIKE FOR HIM AND HIS DEFENSE COUNSEL THIS SHOULD NOT BE A SURPRISE. IF YOU'RE LOOKING AT HOW THE GAG ORDER HEARING WENT LAST WEEK, IT DID NOT GO WELL FOR THEM AND THEY WOULD HAVE HAD TO EXPECT THAT ON SOME LEVEL THEY WOULD WANT TO BE FOUND IN CONTEMPT. I DO THINK THAT WHAT JUDGE MERCHAN DID IN THIS ORDER BY LAYING OUT A PATH GOING FORWARD AND HINTING AT THE NOTION OF INCARCERATION FOR DONALD TRUMP, IT IS A GOOD THING, BECAUSE IT DOESN'T NECESSARILY MEAN THAT THE NEXT TIME THAT HE VIOLATES THE GAG ORDER SHOULD IT HAPPEN THAT HE'S GOING DIRECTLY TO JAIL. BUT IT DOES LAY OUT THE FOUNDATION FOR THAT ULTIMATELY BEING SOMETHING THAT JUDGE MERCHAN RULES ON AND SENDS HIM TO PRISON -- SENDS HIM TO JAIL AT LEAST, SHOULD HE CONTINUE TO VIOLATE THE ORDERS. I THINK THIS WAS THE RIGHT CALL. I THINK LIKE I SAID, EVEN THOUGH THE FORMER PRESIDENT MAY NOT NECESSARILY BE HAPPY ABOUT IT, I WOULD IMAGINE THAT HIS DEFENSE ATTORNEYS ARE NOT SURPRISED AT THIS ORDER GIVEN HOW POORLY THE GAG ORDER HEARING WENT LAST WEEK. >> AND SO, DANNY, DANNY CEVALLOS IS JOINING US, CRIMINAL DEFENSE ATTORNEY, WHAT DO YOU THINK THIS MEANS FOR THE UPCOMING GAG ORDER HEARING THAT IS ON THURSDAY FOR THESE FOUR ADDITIONAL PENDING GAG ORDER VIOLATIONS? >> WELL, IT SETS THE BAR. WE WERE WAITING FOR A DECISION ON THE FIRST GAG ORDER. WE HAD AN IDEA WHERE THE JUDGE WOULD BE IN TERMS OF EVEN DEFINING WHAT WOULD BE A VIOLATION OF THE GAG ORDER FOR THE SECOND GAG ORDER HEARING. JUST TO GIVE YOU AN EXAMPLE, I WONDERED WHETHER THE JUDGE WOULD CONCLUDE THAT REPOSTING SOMETHING AS OPPOSED TO JUST POSTING SOMETHING WOULD CONSTITUTE A VIOLATION OF THE GAG ORDER. WE HAVE NOW LEARNED THAT ACCORDING TO THE ORDER, A REPOST CAN VIOLATE THE GAG ORDER. IT IS INTERESTING, BECAUSE PEOPLE REPOST THINGS ALL THE TIME, THEY DON'T NECESSARILY MEAN THEY'RE ENDORSING IT. BUT, CONTEXT IS EVERYTHING, AND YOU CAN PROBABLY CONCLUDE THAT WHEN DONALD TRUMP REPOSTS SOMETHING FAVORABLE ABOUT HIMSELF, THEN HE IS SPEAKING AND ENDORSING THAT. AND THEN IN ADDITION, YOU HAVE SOMETHING THAT REALLY WASN'T REPOSTING WHEN HE REPOSTED WITH HIS OWN WORDS THE JESSE WATERS QUOTE WHICH HE CHANGED, AND WHEN YOU DO THAT, IT GETS INTERESTING BECAUSE THIS FEELS MORE LIKE A COPY RIGHT ARGUMENT WE'RE MAKING, DID HE CHANGE IT, DID HE ADD TO IT, DID HE PUT HIS OWN SPIN ON IT, BUT THESE ARE ALL GOING TO GOVERN HOW THE JUDGE LOOKS. IT BECOMES ESSENTIALLY THE LAW OF THE CASE NEXT WEEK AND FOR THE WEEKS AFTER BECAUSE I DON'T KNOW WHO AMONG US DOESN'T THINK THAT NEXT WEEK WILL BE THE FINAL GAG ORDER HEARING. I'M SURE THESE WILL BE ON A ROLLING, ONGOING BASIS. IT SEEMS LIKE THE JUDGE JUST PLANNED ON IT ONCE A WEEK TO DEAL WITH GAG ORDER VIOLATIONS. BUT WE KNOW NOW THIS SETS A FLOOR. WE KNOW WHERE THE JUDGE'S MIND IS IN DEFINING WHAT IS AND IS NOT A