What does Matthew 22:15 mean?

Given the three parables Jesus has just delivered (Matthew 21:28, 33; 22:1), this verse should come as no surprise. Jesus told those stories in the temple to a group of religious authorities. In the parables, Jesus first pictured Israel's spiritual leaders as a son who says "yes" to his father but does not actually obey. He pictured them as tenants who kill the landowner's servants and son, rather than paying their rent. Finally, He pictured them as people chosen by a king to attend the wedding feast of his son, yet who refuse to the point of violence and are declared unworthy. All of these depict groups like the Pharisees, scribes, and Sadducees as hypocritical and rebellious against God, despite their lofty reputations with the people.

The Pharisees want Jesus out of the picture. They conspire looking for a way to trick Jesus into making a public gaffe. Ideally, they'd like to fool Jesus into saying something which will upset His crowd of followers: those who think He is the Messiah, and who hope He will soon overthrow the Romans and return Israel to glory. If they cannot do that, their next best option is getting Jesus to say something which sounds like rebellion against the Romans. Then, the Romans will arrest and execute Him.

Ironically, the Pharisees plotting against Jesus only confirms what He has said about them in the previous parables. They are actively—even violently—rejecting the Son of God as the Messiah (Matthew 21:38–39). The following verses show these men are willing to be deceptive to accomplish their goal.