What does Matthew 20:22 mean?

The mother of James and John has asked an enormous thing of Jesus, that her two boys would be seated on his right and left hands in His kingdom (Matthew 20:20–21). Anyone in those seats closest to the king would be the most powerful men in the kingdom under the ruler himself.

He turns away from their mother to address James and John directly. This response shows that Christ understands they are making this request of Him, through their mother. She did not spring this idea on Jesus without their knowledge. She was acting as their agent. This makes even more sense if this woman is Mary's sister, Jesus' aunt, as some scholars suggest may be the case.

Jesus' response feels like an understatement. He tells these two bold men that they do not know what they are asking. He has not come, as they suppose, to set up a political kingdom on earth at this time (John 18:36). They should know that by now. He has told them three times that once they reach Jerusalem, he will be condemned by the Jewish religious leaders, handed over to the Romans for execution, and killed. He has also told them He will be raised on the third day (Matthew 16:21; 17:22–23; 20:17–19).

It's important to be fair about what James and John could have understood at the time. Hindsight is powerful, and our views benefit from completed Scripture and the influence of the Holy Spirit (John 14:25–26). They simply did not grasp why Jesus was saying this or what His death and resurrection would accomplish. Their request reveals not only their own ambition, but also their misunderstanding of what Jesus has taught about how to be great in the kingdom of heaven: childlike humility (Matthew 19:13–15).

Now Jesus asks a pointed question to show they do not understand what they are asking. He is symbolically referring to suffering and judgment, using a common picture from the Old Testament Scriptures. Jesus is asking if they are prepared to suffer as deeply as He is about to: when He will be tortured, sacrificed, and killed on the cross in Jerusalem.

James and John answer, too quickly, that they can drink Jesus' cup of suffering, demonstrating once more their lack of understanding (Matthew 20:23).