Jesus weeps over Jerusalem in Luke 19:41-44. After the triumphal entry, in the midst of the shouting, worshiping, multitude, was a weeping King. Jesus saw the Jews' coming judgment for rejecting him in five days.

Table of contentsThe Bible Contains Vivid Descriptions of Men CryingJeremiah’s Weeping Is a Type of Jesus’ WeepingWhy Did Jesus Weep Over Jerusalem?The Jews Rejected Peace When They Rejected the Prince of PeaceJesus Saw the Jews' Coming JudgmentHow Did Jesus Weep Over Jerusalem?Weep in Hell or Have Your Tears Wiped Away in Heaven

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Jesus weeps over Jerusalem in Luke 19:41-44, because he saw the Jews' coming judgment for rejecting him in five days.

We had our tenth child, Hudson Taylor LaPierre at the end of October. So far, he has been a great baby. But if he cried a lot, it wouldn’t surprise us because we expect babies and infants to cry.

We understand God created men and women differently. Women tend to be more sensitive and emotional than men. Because of that, we are not surprised when women cry. But because we don’t expect men to cry, at least not as much as babies or women, there can be something dramatic, and even moving about men, especially grown men, crying.

The Bible Contains Vivid Descriptions of Men Crying

When David and his men were hiding from Saul, they returned to Ziklag where they were staying with their wives and children. They found Ziklag burned to the ground and their wives and children kidnapped:

1 Samuel 30:3 When David and his men came to the city, they found it burned with fire, and their wives and sons and daughters taken captive. 4 Then David and the people who were with him raised their voices and wept until they had no more strength to weep.

This isn’t what we normally think of as weeping. Weeping doesn’t sap all your strength. David and his men wept, or probably more like sobbed or wailed, until they were completely exhausted.

When you consider the type of men these were, I think their weeping looks even more dramatic. They were used to killing other men with swords or their own hands when they were close enough to look in their faces. These included David’s mighty men who had been hardened by war, hunger, thirst, fighting, and fear of death. But there’s no record of anything driving them to this point before.

But now they weep like this because they know their wives and children were captured by some of the wickedest people in history: the Amalekites. If there was ever a group you would want to keep as far away from your family as possible, it was them. They were so evil that decades earlier God commanded Saul to exterminate them. But because he failed, they were able to attack David and his men’s families.

Another example that stood out to me was when Esau realized he would receive no blessing, because he gave away his birthright:

Genesis 27:34 As soon as Esau heard the words of his father, he cried out with an exceedingly great and bitter cry and said to his father, “Bless me, even me also, O my father!…38 Have you but one blessing, my father? Bless me, even me also, O my father.” And Esau lifted up his voice and wept.

Esau was another man’s man. He was a hunter. He was hairy, even as a baby. You know you’re a man’s man when you’re hairy even as a baby. But when he learned that he would receive no blessing from his father,  he wept loudly. It is sad picturing a grown man sobbing and begging his father to give him something.

I also thought about Job’s friends because they wept, not for themselves, but for Job. When they heard the news about what happened, they went to visit him:

Job 2:12 When they saw him from a distance, they did not recognize him. And they raised their voices and wept, and they tore their robes and sprinkled dust on their heads toward heaven.

These grown men wept loudly for their friend because his trials left him unrecognizable to them.

Jeremiah’s Weeping Is a Type of Jesus’ Weeping

Jeremiah has the unique distinction of being known for his weeping:

Matthew 16:13 Jesus…asked his disciples, “Who do people say that the Son of Man is?” 14 And they said, “Some say John the Baptist, others say Elijah, and others Jeremiah or one of the prophets.” 

Let’s briefly talk about each of these guesses, because they give us a unique insight into how people viewed Jesus during his earthly ministry.

First, some people said he was John the Baptist. John 10:41 says John never performed a miracle. So, they didn’t think Jesus was John because Jesus and John performed miracles.

They more than likely thought Jesus was John because of their similar preaching. They both preached repentance and truth regardless of how it was received and confronted the religious leaders.

There are multiple reasons people could have guessed Elijah. Elijah and Jesus were both famous miracle workers. They were known for bold, uncompromising preaching. Elijah went up to heaven in a whirlwind without dying, which made it easier to believe he returned as Jesus. Finally, and most significantly, there was an Old Testament prophecy that Elijah would appear again:

Malachi 4:5 “Behold, I will send you Elijah the prophet before the great and awesome day of the Lord comes.

This is the second-to-last verse of the Old Testament, which means it is the second-to-last verse God spoke for over 400 years. So, you can imagine the attention it received. The verse prophesied God would send Elijah back, and it prophesied of Elijah returning as one of the two witnesses in Revelation 11. But the people in Jesus’ day didn’t have the book of Revelation, so Elijah was a logical guess.

The third person they named is Jeremiah. We know Jeremiah resembles Jesus, because of the rejection, betrayal, and suffering they both experienced. But the problem is, Jesus had not experienced much rejection, betrayal, and suffering when they said this. All of that is still in the future. So why did people think they were the same person? I think it was because of their sorrow. Jeremiah is the author of Lamentations, and Jesus is:

Isaiah 53:3 He was…a man of sorrows and acquainted with grief.

Like Jeremiah, Jesus was known for his sensitivity and tenderheartedness. Nine times in Matthew, Mark, and Luke, we read about Jesus’s compassion. Just using Matthew’s gospel:

Matthew 9:36 When he saw the crowds, he had compassion for them, because they were harassed and helpless, like sheep without a shepherd.

Matthew 14:14 When he…saw a great crowd, and he had compassion on them and healed their sick.

Matthew 15:32 Jesus…said, “I have compassion on the crowd because they have been with me now three days and have nothing to eat.”

Jesus was deeply compassionate, and we don’t see his compassion for people any better than when he weeps over Jerusalem. I like shadows and types of Christ. Initially this lesson said that Jeremiah is a type of Jesus, but I changed it because as I studied this week, it seemed like not only did Jeremiah prefigure Jesus, Jeremiah’s weeping over Jerusalem prefigures Jesus’ weeping over Jerusalem:

Jeremiah 9:1 Oh that my head were waters, and my eyes a fountain of tears, that I might weep day and night for the slain of the daughter of my people!

Jeremiah said he wept for all the Jews who would be slaughtered. He’s talking specifically about when Babylon sieged Jerusalem, destroyed the temple, slaughtered countless Jews, and took many others captive. Let me illustrate this by describing someone and then asking you who I am describing.

Jerusalem would be sieged and then broken into. The temple would be destroyed. Hundreds of thousands of Jews would be slaughtered, and thousands more would be taken captive. A man thought about this and wept. Who is the man?

I could be talking about Jeremiah, the weeping prophet, as he thought about what would happen to Jerusalem at the hands of the Babylonians in 600 BC.

I could be talking about Jesus, the weeping Savior, as he thought about what would happen to Jerusalem at the hands of the Romans in 70 A.D.

Just as Jeremiah was brokenhearted over what was going to happen to the Jews in his day, so too was Jesus brokenhearted over what was going to happen to the Jews in his day.

Many Old Testament events prefigure or foreshadow New Testament events. The similarities between the Babylonians attacking Jerusalem, destroying the city and the temple, slaughtering the Jews and taking many of them captive in Jeremiah’s day is so similar to the Romans doing the same thing to Jerusalem in 70 A.D. that it looks as though the Old Testament event foreshadows the New Testament one.

Why Did Jesus Weep Over Jerusalem?

We are jumping into the middle of the triumphal entry:

Luke 19:37 As he was drawing near—already on the way down the Mount of Olives—the whole multitude of his disciples began to rejoice and praise God with a loud voice for all the mighty works that they had seen, 38 saying, “Blessed is the King who comes in the name of the Lord! Peace in heaven and glory in the highest!” 39 And some of the Pharisees in the crowd said to him, “Teacher, rebuke your disciples.” 40 He answered, “I tell you, if these were silent, the very stones would cry out.”

There were probably thousands of people, and it says they were rejoicing and praising God with loud voices. There is no other celebration like this in the Gospels. The response was so staggering the religious leaders couldn’t handle it. This was Jesus’ coronation, so if the people were silent, creation itself would respond.

All the Gospels record Jesus’ Triumphal Entry, but Luke records something completely shocking that is not in the other Gospels:

Luke 19:41 And when he drew near and saw the city, he wept over it,

You will get much more from your Bible reading if you picture what is being described,