So after they had assembled, Pilate said to them, “Whom do you want me to release for you, Jesus Barabbas or Jesus Who is called the Christ?” – Matthew 27:17 (NET)
Jesus, called the Christ, was Jesus, the one being called “the Messiah.” All of Pilate’s hearers, and most likely Pilate himself, knew exactly what was implied by this title. This would not have been the first “Christ” or “Messiah” with whom Pilate had dealt, and it would probably not be the last one as well, as Pilate was the procurator of Judea at a time when Jewish national expectations were at a fever pitch, and messianic contenders---all of whom, save one, turned out to be nothing more than pretenders---were presenting themselves on a semi-regular basis, in their desire to usher in the kingdom of God, enthrone their king in the line of David, throw off their pagan oppressors, and finally bring Israel’s historical purpose (as they saw it) to its climax, resulting in national Israel ruling over all nations.
It’s an interesting side-note that Matthew provides, writing that Pilate “knew that they had handed Him (Jesus) over because of envy” (27:18). Jesus’ popularity with the masses, and His unwillingness to enter into league with any of the leaders or rulers or popular movements of the day, was a source of irritation for those that wanted to be in control of any potentially successful messianic movement, or who wanted to suppress such movements due to the positions that they were currently holding.
Jesus’ interaction with Pilate is fascinating. Pilate asks Jesus “Are You the King of the Jews?” (27:11b) Jesus replies, “You say so” (27:11c), which is an expression of affirmation. This is a rather damning admission on Jesus’ behalf. In that time, anybody that would have admitted to such a thing would have been swiftly dealt with through crucifixion, whether they proclaimed themselves King of the Jews, the Greeks, or the Gauls. Any claim of kingship was seen as a rival claim to the supreme rule of Caesar, and so would not be allowed to stand. Jesus would have been well aware of this. At the same time, Pilate would have had to been thinking that this was the first time that he found himself dealing with a would-be Jewish messiah, that was not conducting overtly revolutionary activities in support of his aspirations to kingship. There was no band of armed men around Jesus. He had not taken up arms. There were no overt or even implied threats of force or demands against the Roman rulers of Israel, yet here this Man was claiming to be something that was going to result in His crucifixion. Pilate would hear Jesus being “accused by the chief priests and the elders” (27:12b), while also making note of the fact that, to them, Jesus “did not respond” (27:12b). In all this, we find that Pilate “was quite amazed” (27:13b).
As he is in this state of amazement, we head back to the original question: “Whom do you want me to release for you, Jesus Barabbas or Jesus Who is called the Christ?” Having already made note of the fact that Jesus had no armed band of followers, and that He was not acting as Israel was expecting their messianic king to act, the people responded with “Barabbas!” (27:21b). You see, Barabbas was being held for insurrection. He was imprisoned, and most likely awaiting death, having been charged with the type of things that the people wanted to see Jesus doing, which was attempting to effect the overthrow of Roman rule through violent rebellion. Jesus was not doing that, so yes, though He had healed the sick and restored people to life, He had also stirred up hopes that He was apparently not going to fulfill, so “away with Him! If He is going to fail to do what we expect our messiah to do, He is a failure and must suffer the fate of all failed messiahs.” “Crucify Him!” (27:22b) “Crucify Him!” (27:23b)
Pilate, with knowledge that Jesus had truly done nothing that would provide sufficient and legitimate grounds for the infliction of such a punishment, had said, “Why? What has He done?” (27:23a); but the tide of popular opinion had turned. Ironically, there was always the under-current that Roman action against popular, potential messiah figures would induce rioting by the populace, as riot and revolution was the goal of those that rose to prominence under the messianic banner. In this case, however, Pilate was seeing that the people were going to riot if he failed to crucify this particular, potential messiah (27:24). This was a strange turn of events. These people, in all of their expectations and fervor, were now demanding an unjust execution, in the absence of evidence of violence and attempted overthrow.
As we move forward in the story, we find Barabbas released, with Jesus flogged and handed over to be crucified (27:26). Having been handed over, “They stripped Him and put a scarlet robe around Him, and after braiding a crown of thorns, they put it on His head. They put a staff in His right hand, and kneeling down before Him, they mocked Him: ‘Hail, king of the Jews!’” (27:28-29). While we see rightfully see this as the mocking for which it was clearly intended, we can also understand the pragmatism on display. Pilate, like most politicians, was concerned for his position and his future, and imperial actions such as crucifixions were most likely accompanied by reports to his superiors in Rome. So just to be on the safe side, seeing as how he had condemned this man to crucifixion for His claim to be a king---though there was no evidence ready at hand that suggested any harm to Rome or to Caesar in this statement---a coronation ceremony was conducted, with all the necessary royal emblems and honors. Now, having been presented as a king, by and to Roman soldiers no less, this Jesus fellow could safely be sent to the cross and Pilate, having “washed his hands before the crowd” (27:24b), could be done with the whole messy ordeal.