After three parables in response to a challenge to his authority, the Pharisees and Herodians plot to entangle Jesus with a political question with no safe answer: paying taxes to Caesar. For Pharisees and Herodians to join forces is a little like Hillary Clinton and Donald Trump joining forces against a common enemy. Impossible!
This is a plot (συμβούλιον, literally, “take council”) to capture Jesus (v. 15). Matthew uses this word five times (12:14; 22:15; 27:1, 7; 28:12), each time describing a plot against Jesus. The idea is of plotting, etc. This incident was foreshadowed in 12:14, just after Jesus declared that the Pharisees were committing an unforgivable sin.
The plot should trap Jesus by his own words. The verb (παγιδεύω) is only used here in the New Testament, elsewhere it is used for snaring birds with a net (BrillDAG). The word evokes the image a net entangling something so that they cannot get out of a trap. We have all said things we immediately regret, then try to back out of what we said and end up saying something even worse.
The Pharisees flatter Jesus before asking the question (v. 16). This is not at all unusual (especially if this is a younger disciple) and the questioner does not say anything untrue about Jesus. Jesus is true and he does teach the way of God truthfully. “The way” may refer to the way of righteousness (Psalm 1, for example). Jesus is not swayed by appearances, literally, “to look at the face of men.” This usually means “does not show favoritism.”
After laying on the flattery, they ask the question: Is it lawful to pay taxes to Caesar or not? (v. 17). The question asks for a decision based on the Law, does the Mosaic Law require us to pay taxes to Rome? If Jesus answers yes, then he sounds “pro-Rome” and risks being attacked by the patriotic crowds gathered for Passover. If he says no, then he risks being arrested by the Romans as an anti-Rome rebel.
What was the problem with taxes? Taxation was both a political and religious issue in the first century. In A. D. 6, a Galilean Jew named Judas led a revolt against paying taxes to Rome (Acts 5:37; Josephus, Ant. 18.1). For Judas the Galilean, any tax paid to Rome was a symbol of subjugation. His sons were executed in AD 46 (Ant. 20.5.2) and his grandson was involved in the First Jewish Revolt (Menachem ben Judah, JW 2.433-450). Rome set high taxes in Palestine since the region was troublesome (Nolland, Matthew, 896).
Josephus, Jewish Wars, 2:118 Under his [Archelaus, AD 6] administration it was that a certain Galilean, whose name was Judas, prevailed with his countrymen to revolt; and said they were cowards if they would endure to pay a tax to the Romans, and would, after God, submit to mortal men as their lords. This man was a teacher of a peculiar sect of his own, and was not at all like the rest of those their leaders.
Acts 5:37 After him Judas the Galilean rose up in the days of the census and drew away some of the people after him. He too perished, and all who followed him were scattered.
Another issue may have involved the imagery used on Roman coins. A Roman denarius almost always used an image of the emperor and propaganda calling the Emperor a son of the divine Augustus, the savior, etc. In all cultures, money is propaganda. Rome used coinage to create the image of an all-powerful empire responsible for peace and prosperity. “The Essenes refused to use the denarius, ‘saying that they ought not either to carry, or behold, or fashion an image” (Davies and Allison, Matthew 3:216, but they cite no source for this).
Jesus responds with great wisdom (22:18-22). He is fully aware this is a trap and that the whole crowd is waiting for his answer. Jesus calls them hypocrites. The hypocrisy of the Pharisees is the theme of Matthew 23. The word originally referred to an actor, someone playing a role, a “pretender” (BDAG). The Pharisees asking the question are pretending to be respectful towards Jesus, but they are full of malice and want to trap Jesus into saying something worthy of arrest and maybe even execution.
Jesus asks then to show him a “coin for the tax.” A Roman denarius is a common coin worth about day’s wage for a laborer. In Matthew 20:1-2, the owner of a vineyard promised some workers a denarius for working one day in his vineyard. It is not unusual a Pharisee would have a Roman coin. Even if they hated Rome, they still needed the coins to buy and sell. (Imagine visiting China and refusing to use money with Mao’s picture on it.)
Jesus declares, “Give Caesar what is due to Caesar.” What happens if you do not “Render unto Caesar”? Jesus is saying something like “pay Caesar what you owe him.” Some people in the audience might think “we owe him nothing” while others see taxes as payment for the service the Romans provide (roads, aqueducts, military protection). Could someone pay the taxes without worshiping Caesar? A Pharisee might say yes: if we pay the taxes then Rome leaves us alone and we can study Torah in peace. A Herodian would agree as well, they are the local government benefiting from Roman taxes, although they might have been more inclined to offer more deference to the emperor (there was an Augustan Temple in Caesarea, for example).
Jesus then adds, “But give to God what is due to God.” If Jesus is right about paying taxes to Rome because they are obligations which are due, then how much more important are one’s obligations to God! In the context of the first century, one’s obligation to God might include the Temple Tax (which Jesus paid, Matthew 17:24-27, for example).
Consider all of Jesus’s teaching in Matthew: one’s obligations to God go far beyond money (tithes and offerings). There are several times in the book Jesus’s demands from the true disciples go far beyond the Pharisees, for example.
In the context of the parables in Matthew 21-22, the Pharisees and Herodians who are asking him this question are not giving to God what he is due, they are hypocrites. Since they rejected Jesus as Messiah, they are not “rendering unto God.”