What does Matthew 22:16 mean?

The Pharisees want Jesus out of the picture one way or another. Despite His indirect—and, according to them, blasphemous—claims to be the Messiah and the Son of God, they can't arrest Him directly. Jesus is just too popular with the people for the moment. Earlier encounters showed that these religious leaders are more interested in political power than in honesty (Matthew 21:25–27). If they can get Him to say anything that sounds like rebellion against Rome, however, the Romans might remove Jesus for them. The Roman Empire was more than willing to execute Jewish rebels attempting to start an uprising.

Jesus, of course, was not trying to cause an uprising (John 18:36). That's one reason this plot by the Pharisees will not work. Still, they take a shot. They send some of their disciples to Jesus, along with representative from a group known as the Herodians. These Jews were loyal to the Herods and wanted Rome to give the kingship of Israel back to them. To that end, they did not want to do anything that would make Rome feel threatened by the Jewish people.

This mixed group approaches Jesus and begins with flattery. They respectfully call him "Rabbi," meaning "Teacher." They flatter His teachings and wisdom, as well as His independence and bravery. The setup makes it seem as if they are asking Him to settle a dispute between them and the Herodians. In political arenas, this kind of trickery is common; the group is trying to lower Jesus' guard by saying He is so smart and truthful and unworried about what others think that He is the perfect arbiter for the question they are about to pose.

Likely, the Pharisees assumed Jesus would not believe any flattery they might use. So, they sent their students, rather than approach Jesus directly. In their minds, Jesus was more likely to fall to flattery from younger people. Of course, He does not, and would not (Matthew 22:18).