Summary: Jesus' weeping over Jerusalem in Luke 19:41-44 shows us the compassion of Jesus.

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Jesus’ three-year-long ministry was about to come to an end.

Luke 19:28 is the beginning of Jesus’ final week on earth. It began with his triumphal entry into the city of Jerusalem. The people were rejoicing and praising God with a loud voice for all the mighty works that they had seen Jesus do. They were exuberant about his arrival at Jerusalem. They thought that he was the coming Messiah, but they misunderstood his true mission. They wanted a political Messiah, a political Savior, someone who would free them from Roman oppression. But Jesus was a spiritual Messiah, a personal Savior, someone who would free them from sin and judgment and hell.

As Jesus approached Jerusalem, coming down the Mount of Olives with Jerusalem in view just across the valley, and with all the people still surrounding him, he burst into tears.

Let’s read about Jesus’ weeping over Jerusalem in Luke 19:41-44:

41 And when he drew near and saw the city, he wept over it, 42 saying, “Would that you, even you, had known on this day the things that make for peace! But now they are hidden from your eyes. 43 For the days will come upon you, when your enemies will set up a barricade around you and surround you and hem you in on every side 44 and tear you down to the ground, you and your children within you. And they will not leave one stone upon another in you, because you did not know the time of your visitation.” (Luke 19:41-44)


Eric Wilson, professor of English at Wake Forest University, wanted to become a happier person. He at least wanted a smile on his face, rather than the scowl people were used to seeing. Friends urged him on to a sunny disposition. He purchased books to become happy, watched only uplifting movies, and inserted “Great!” and “Wonderful!” into his conversations.

But none of these things helped, and the professor eventually went back to being his usual melancholy self.

Turning against what he calls “the happiness movement,” he wrote a book titled Against Happiness. He believes Americans are fixated on happiness – to the extent of even fostering “a craven disregard” for whatever shows a mere hint of melancholy.

The happiness movement bloomed in the 1990s, motivated by scientific studies on the brain and the rise of “positive psychology.” But now there’s a backlash against a philosophy that says “normal sadness is something to be smothered, even shunned.” Further study has actually discovered that “being happier is not always better.”

Those who know some discontent are motivated to improve their lot in life and the condition of their community.

“If you’re totally satisfied with your life and with how things are going in the world, you don’t feel very motivated to work for change,” says Ed Diener, an author who has written a book similar to Wilson’s. Deiner notes that when experiencing a negative mood, “you become more analytical, more critical, and more innovative. You need negative emotions, including sadness, to direct your thinking.”

Jesus, of course, had perfect emotions. He did not need to read on how to become happy. Interestingly, the Bible never records Jesus as smiling or laughing. No doubt he did smile and laugh because that is a perfectly good emotion.

Nevertheless, the Bible does record Jesus as weeping. He wept when his friend Lazarus died (John 11:35) and, of course, he wept in our present text. And so, when we read about Jesus weeping, we should pay attention because it teaches us something very important about Jesus and about us.


Jesus’ weeping over Jerusalem in Luke 19:41-44 shows us the compassion of Jesus.

Let’s use the following outline:

1. Jesus Weeps for Unrepentant Sinners (19:41-42)

2. Jesus Warns Unrepentant Sinners (19:43-44)

I. Jesus Weeps for Unrepentant Sinners (19:41-42)

First, Jesus weeps for unrepentant sinners.

In the previous pericope (Luke 19:28-40) Jesus had just walked from Jericho to Jerusalem, a distance of about 17 miles. This journey took place on what we call Palm Sunday. As Jesus and his disciples drew near to Bethphage and Bethany on the east side of Jerusalem, he sent two disciples ahead of him to get a donkey’s colt. You may recall, if you were here the last time I preached, that Jesus’ use of a donkey’s colt was a deliberate claim to be king. He was fulfilling the prophecy of Zechariah 9:9, which states, “Rejoice greatly, O daughter of Zion! Shout aloud, O daughter of Jerusalem! Behold, your king is coming to you; righteous and having salvation is he, humble and mounted on a donkey, on a colt, the foal of a donkey.” Jesus wanted to assert his kingship, and that he was a king coming in love and peace. And, of course, this was not lost on the people in Jerusalem.

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