What does Matthew 20:18 mean?

Matthew has reminded us that, despite frequent detours for teaching and healing, Jesus is still headed "up" to Jerusalem. Because of its elevation, Jerusalem was generally said to be "up" from anywhere in Israel. Jesus is not yet there, however. He has more to do before finally arriving to meet the events He describes in this and the following verse.

Jesus says this even more clearly and plainly to the disciples than He has the previous two times (Matthew 16:21; 17:22–23). He wants them to understand exactly what is coming and that He is moving toward it of His own free will. He wants them to remember this.

When they reach Jerusalem, the Son of Man will be delivered over to the chief priests and scribes, and they will condemn Him to be executed. Jesus often refers to Himself as the Son of Man (Matthew 8:20; 9:6; 17:9). He reveals once more that He will be delivered to the Jewish religious leaders. The fact that He will be condemned means His death won't be a sudden stoning or push from a cliff in the heat of the moment. Jesus knows He will face a legal proceeding. A deliberated judgment of death will be rendered in response to a charge against Him.

The fact that Jesus knew all of this was coming tells us at least two things. First, His commitment, His resolve, to carry out the will of His Father and demonstrate God's love for the world (John 3:16) was absolute. He would not just show up and hope for the best. He knew what was coming and kept going toward it. Second, Jesus has demonstrated that He contained all the power needed to keep from being arrested, convicted, and condemned to death. The fact that He knows what is coming shows that He was not overcome.