What does Matthew 22:19 mean?

A group of Pharisees, along with some Herodians, have set a trap for Jesus. Through flattery and deception, they pretend to seek arbitration for a dispute (Matthew 22:15–16). Their loaded question is whether it is "lawful" for a faithful follower of God to pay taxes to the pagan, oppressive Roman government. This tax—like those who helped Romans collect it (Matthew 9:11)—was deeply despised by the Jewish people. Some Israelites suggested they should defy the Roman government, believing they should trust God to send the Messiah to free them from Rome and return them to the glory days of Israel. The Pharisees hope these people will be offended if Jesus declares that Old Testament law requires them to pay this tax.

On the other hand, the Herodians wanted to keep the trust of Rome by keeping order in Israel. They wanted everyone to behave and to keep paying their taxes. If Jesus said not to pay the tax, the Herodians might have Him arrested and turned over to Rome as a rebel. Either outcome would suit the desires of Jesus' enemies.

Jesus seems especially disgusted with this feeble attempt to trip Him up (Matthew 22:18). In somewhat dramatic fashion, He asks to see a coin that could be used to pay the tax, planning to use it as a visual aid (Matthew 22:20–21). More than one currency was in use in Israel at this time. The Jewish people did not like to use money with foreign gods on it and some had rebelled over the issue in AD 6. They lost that battle, so the Roman tax could now be paid only with the silver Roman denarius.