Matthew 22 is a direct extension of Matthew 21. In my Bible i have actually crossed out the chapter number for 22 to de-emphasize the separation. Overall, the day that these chapters represent would have been a day to sell tickets to, pop some popcorn, sit back, and enjoy the show! Things are starting to get interesting!
Jesus begins the discussion with a parable. A kings son is getting married and he invites the important people to the wedding feast, but no one is willing to go. Rather they abuse and kill his messengers. So he destroys them, and he invites strangers from the street… anyone willing to come. The Pharisees know that this parable is directed towards them, so they fire a couple of volleys back. They try to trap Jesus between the law of the land and the sentiment of the people. Jesus walks through that trap pretty easily. Next the Sadducees (who do not believe in the resurrection of the dead) test Him. Jesus not only clears that trap, but He also answers to and clarifies the truth / theology to respond to their confused beliefs. So instead they send in a legal expert to test Him. The legal expert questions Jesus, and of course He answers beautifully. Finally, Jesus asks them a tough question about the Messiah and how the Messiah does not fit their viewpoint / expectations.
All of this silences the pharisees… “No one was able to answer Him a word, nor did anyone dare from that day on to ask Him another question.” He wins the debate. He wins the day, and many of His enemies are now solidified against Him. Ultimately though, it’s all part of the plan, and He prevails.