What does Matthew 20:29 mean?

Matthew describes one last miraculous display of God's power in Jesus before He arrives in Jerusalem. Jesus and His disciples have been on the way to Jerusalem for some time, taking a longer route to get there. Now they are getting closer. Jericho is just northwest of the top of the Dead Sea, about 15 miles from Jerusalem.

The Jericho mentioned here is not the same city destroyed by Joshua and the Israelites as they entered the Promised Land (Joshua 5–6). It is the "new" Jericho, located about a mile to the south.

Matthew and Mark set this scene as Jesus and the disciples are leaving Jericho. Luke, though, describes Jesus as having entered Jericho and passing through it (Luke 19:1). This slight difference can be explained in at least two ways. The most obvious would be that Luke is describing Jesus as entering, "passing through," and then coming out the other side when this interaction happens. The other option is that Luke reported Jesus entering and passing through the new Jericho, while Matthew and Mark describe the company as leaving the old one.

In any case, a large crowd was following Jesus. Large crowds often followed Him in hopes of witnessing miraculous healing or hearing Him teach. This crowd was likely even larger, since many Israelites would have been travelling to Jerusalem for Passover.