It’s interesting that Matthew gives more time to the events of Tuesday than any other day during Holy Week. John prefers to spend time in the upper room with Jesus and the disciples on the night He was betrayed. Perhaps the significance of Matthew’s perspective gives us a pointed warning to the false teaching in contrast to everything that Jesus has said. Matthew is showing us the increasing opposition Jesus is facing while presenting His call to repent and live for the Kingdom of Heaven.
As already mentioned, Jesus begins this Tuesday by explaining to His disciples the meaning of the withered fig tree. He had upset the religious leaders by accepting the worship of the people on Sunday, He ran the money changers out of the temple on Monday, and now He’s headed back into the temple to confront the religious leaders, but this time, they are armed and ready to take Him down.
First, they tried to trap Jesus with a political question: “Who should we pay taxes to?” Notice that they made sure the Herodians were close by. The Herodians were the supporters of the illegitimate ruling party established by the Roman government. The Pharisees and Herodians didn’t even get along.
Then, the Sadducees, who didn’t even believe in the resurrection, asked Jesus a theological question: “Is there going to be marriage after the resurrection? And, if so, what about people who had multiple marriages?” Jesus’ answer is consistent with His prevailing message: In order to be a disciple of Christ, we must deny ourselves (Matthew 16:24).
After watching the Sadducees get pummeled, the Pharisees ask a legal question: “What is the greatest commandment in the Law?” Jesus summarizes the law by saying, “You shall love the Lord your God with all your heart and with all your soul and with all your mind.” and then, “You shall love your neighbor as yourself.” This cuts to the heart of the Pharisees who had no love for God or the people they were called to serve.
Jesus then turns to the crowds that had gathered to expose the religious leaders. Jesus predicts the destruction of the temple and prophesies a dark future as Satan seeks to reclaim the kingdoms of this world, all while reminding us of the importance to be ready and focused on the promise of the Kingdom of Heaven.
Today is a day of introspection. We must examine ourselves and make sure that we are not living as the Pharisees did with an external righteousness that neglects the heart. These ‘Woes’ are warnings to us against our own propensity towards hypocrisy.