Riding on a humble beast of burden is not the way in which most people would expect a king to enter into His reign, but that is exactly how the Lord of glory entered His. Though almost no one could see it at the time, Jesus' arrival in Jerusalem on Palm Sunday marked the beginning of the final events that would lead to His exaltation (Matt. 21:1–11).
When we say that almost no one could see it at the time, we are not speaking of what the crowd of Passover pilgrims first thought when they saw Jesus approaching Jerusalem on a donkey. The greatest king in their history, after all, often rode through the Holy City and the Promised Land in a similar manner (2 Sam. 13:29; 1 Kings 1:33). Thus, the people who cried "Hosanna to the Son of David!" on Palm Sunday expected a mighty, conquering king, one who would throw off the yoke of their Gentile oppressors just as David had defeated the Philistines centuries earlier.
Yet the people failed to see the true import of the Davidic king riding on a lowly beast of burden. Yes, David was a conquering king, but he defeated his enemies not in his own strength but in the strength of the Lord. Moreover, for all of his military prowess, David could not provide permanent rest to his people. After his death, his son Solomon enjoyed peace for a time, but this golden age came to an end when God brought enemies against Solomon to discipline him for his idolatry (1 Kings 11:9–40).
The true enemies that had to be defeated were not pagan Gentiles but rather sin and death. This could not be done on a white horse and with great armies. Instead, it took humility, a willingness to take the form of a servant and submit to the punishment that God's people deserve for their sin (Phil. 2:5–11). Only by receiving the worst that sin and death could throw at him could the Davidic king "outsmart" our enemies. In thinking that they were gaining the upper hand, sin, death, and even Satan himself did not see that their actions were ultimately working under the sovereignty of God so that His wrath would be satisfied in the death of His Son. They did not see that by killing Jesus they were actually ensuring their own defeat, for the Son of David whom they murdered was stronger than death itself. Passing through death, He conquered it by rising again. Jesus took the worst that His foes could do and triumphed over it. His humble entry into Jerusalem in fulfillment of Zechariah's prophecy anticipated His final conquering act.
Throughout Scripture we find that humility is the path to victory and exaltation. The world does not expect to find true strength in those who are humble, but God has a way of taking what sinners do not find glorious and using it to reveal His glory and honor. If we would take up the cross of Jesus and follow Him truly, we must likewise seek to find strength only in the Lord by humbling ourselves before Him and others. May God give us the grace to do this.