One of the charges brought by the high priest, Caiaphas, and his retinue, against Jesus was that he had encouraged the people not to pay taxes to Rome (Luke 23:2). It seems that the episode which lay behind this false charge was an exchange between the chief priests and Jesus a few days earlier in the Temple precincts (Luke 20:20-26; Mark 12:13-17; Matt. 22:15-22).
Through his Parable of the Wicked Tenants (Luke 20:9-19; Mark 12:1-12; Matt. 21:33-46), Jesus had warned the leadership of the Temple of the inevitable consequences of their abuses of power. Those in authority recognized the thinly veiled critique. However, they could not move openly against Jesus because of his popularity among the crowds of Jerusalem; they “tried to lay hands on him at that very hour, but they feared the people” (Luke 20:19; cf. 22:53; Acts 5:26).
Instead, the chief priests attempted to trip Jesus up by questioning him in public concerning the obligation to pay taxes to the Roman Empire. These taxes were a bitter pill for the Jewish nation to swallow. They represented the loss of freedom and subjugation to a pagan nation. Josephus reports that only a few years earlier, a certain Judah of Gamala (Acts 5:37) had instigated an uprising in the Galilee in reaction to the census for taxation initiated by Quirinius, the governor of Coele-Syria (cf. Luke 2:2):