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Sermon Notes and Slides

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He Wept Over the City
Luke 19:28-44
Dr. Tony Chute, Lead Pastor

Overview: The ministry of Jesus begins to culminate with His arrival in Jerusalem. Jesus prophetically instructs His disciples to secure for Him a colt upon which no one has ever sat for the purpose of peacefully presenting Himself as Israel’s Messiah. As He descends the Mount of Olives, crowds prepare the way with great fanfare by spreading their cloaks before Him, praising God for His work among them, and confessing that Jesus is the true King. It seems as if Israel is ready to receive her Messiah, but the religious leaders dampen the excitement by calling upon Jesus to silence His disciples. Jesus then weeps over the city, knowing their rejection of Him will result in the destruction of Jerusalem. In light of these events, we are called to recognize Jesus as our King and to weep over those who face judgment also.

01. The tears of Jesus do not indicate failure of purpose or weakness of resolve; rather, they assure us of Jesus’ undying love for those who could be saved but face judgment instead.

02. The tears of Jesus do not allow us to be indifferent about those who are perishing; rather, they illustrate how we should feel about our own souls and the souls of others.


1. Read Luke 19 in its entirety. What is the connection between Zacchaeus’ conversion and the rejection of Jesus by the Pharisees? Why was the tax collector able to see Jesus as the solution to his sins while the religious leaders were unable to see the same? How does self-righteousness prevent us from seeing our need for a Savior? What hope does this provide for people we know who are broken over their sins?

2. How does the Parable of the Ten Minas (Luke 21:11-27) provide a commentary on Israel’s future? How do Jesus’ words in verses 41-45 echo the lesson of the parable? How should the threat of God’s judgment motivate us to come to Him on His terms? Why do people minimize the threat of God’s judgment today? What judgment do people face who do not turn to Jesus for salvation?

3. Read the account of the Triumphal Entry on Palm Sunday from each of the gospels (Matthew 21:1-11; Mark 11:1-10; Luke 19:28-44; and John 12:12-18). What similarities and differences are evident throughout? What subsequent events indicate that trouble would follow His triumphal entry?

4. Read Zechariah 9:9 and consider how Jesus was intentional about presenting Himself as Israel’s Messiah. What other works did He do in His ministry that pointed to His identity as the Messiah? What is the significance of Jesus fulfilling Old Testament prophecy in His ministry? How does His ability to foretell the future and fulfill prophecy encourage us as we live in times of uncertainty?

5. How would our knowledge of Jesus be poorer if we did not know of His tears over Jerusalem? Do you ever think of God’s love for the world in such terms? Have you ever wept over your own sins or the sins of others? Ask the Lord to place people on your heart to pray for and for them to feel their need of a Savior.

For Further Reading: Andreas Köstenberger, Justin Taylor and Alexander Stewart, eds. The Final Day of Jesus: The Most Important Week of the Most Important Person Who Ever Lived (Crossway, 2014)