Important to point out that the troop contingent in Jerusalem was much higher during the Passover.  More than enough to put down anything less than an all-out insurrection by the greater part of the populace, and there is no possibility Jesus had anywhere near that much support.  I think probably a few hundred people were genuinely interested, and most of them not all that committed.  If it was a few thousand, and they were all deeply committed to Jesus, the disciplined Roman troops could still quell them without much difficulty.  In the event, even his disciples, who were certainly devoted to him, abandoned him, knowing they were up against insuperable odds (and Jesus had taught them to be nonviolent).  

If we posit that he did have a lot of support, then why did so few Jews in Jerusalem convert?  Because the crucifixion convinced them he was a false Messiah?  Okay, then killing him was clearly the right course of action for the temple leaders and Pilate to take.  If you told them “This will lead to a new religion that becomes dominant in Rome in a bit under three hundred years and will give Jews everywhere a lot of grief”, and they believed you–well, we know of all kinds of much more horrible consequences stemming from our current actions, in a lot less than three hundred years.  People tend to pay much more attention to immediate consequences than long-term ones.  

Jesus caused enough of a tumult to make him a problem, but not enough to make killing him a worse problem.  That can be said with reasonable certainty.  

The temple authorities were the ones going after Jesus, and they would not engage in an unsanctioned execution–too much risk of blowback.  The Romans could remove Caiaphas from his position as high priest at any time. He lasted 18 years in that position, indicating that he knew how to keep on their good side.  There may have been unsanctioned stonings and such, but they would come from other quarters (zealots), not the temple priesthood, which is trying to keep the more hotheaded Jewish factions in check. 

Odds are, the decision to condemn Jesus came much less from any personal irritation Caiaphas and his fellow priests felt with Jesus’ off-license preaching (there were many other such annoyances) than fears he would (intentionally or not) cause trouble that Pilate would have to put down, and blame them for not keeping their own people in check, which was supposed to be their job, as the Romans saw it.  This would imply Jesus did attract a lot of interest from the people when he came to Jerusalem, due to his remarkable personal charisma (without which we wouldn’t be having this discussion), and the bold originality of his teachings, which would have intrigued (and perhaps also angered) many Jews, during a volatile time of the year. 

There is no record of any major unrest in Jerusalem during this time period.  But Passover was always turbulent there, because of the large number of people coming in from outside the city to celebrate the feast, and emotions running high, since the Jews didn’t want a foreign pagan authority overseeing their religious activities in any way. 

So what happened with Caiaphas and Pilate with regards to Jesus should probably be interpreted as a collaborative act.  Each is solving a problem for the other.  Pilate would be pleased that Caiaphas is doing his job, finding a troublemaker, condemning him, then turning him over to the secular authority–the system works!  Each is proving his authority, sending a warning to potential Messianic pretenders (which for both of them implies someone claiming temporal kingship over Palestine and attempting to overthrow Roman rule–and the existing temple authority.  (Something not only Jesus would have liked to see, Caiaphas would have had many detractors other than Christians.)

The interesting thing for me is the story in Luke about Jesus telling his disciples to obtain swords.  They bring two, and he says that will suffice.  Suffice for what?  Not an insurrection.  Not even a minor fracas.  Is he going to multiply them like the loaves and fishes? 

My personal theory (feel free to ignore it) is that Jesus never intended any rebellion, but he wanted to create the appearance of one–because he wanted to be arrested, believing that what followed would lead to God sending the Son of Man to inaugurate the Kingdom.  He remained nonviolent–violent people cannot enter the Kingdom–but there is no virtue in refraining from violence when you don’t have the potential to inflict it.  Much of what he is described as doing in these final weeks sounds to me like a staged performance, meant to attract attention from the authorities–and it all went as planned until he was there dying on the cross–and God didn’t intervene.