Why Jesus Weeps Over Jerusalem (Luke 19:41-44)

Why Jesus Weeps Over Jerusalem (Luke 19:41-44)

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.

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.

More than likely they 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 is to say this is the second to last verse God spoke for over 400 years. So, you can imagine the attention it received, and it prophesied God would send Elijah back. The verse is prophesying 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, and this is one of those moments that you really need to think about to understand how dramatic it was. In the midst of this shouting, worshiping, multitude was a weeping King. Why is that? It makes absolutely no sense. This is the opposite of what we would expect to read. A moment that should have been filled with joy is instead filled with intense sadness. Jesus’ behavior is so shocking, because the Jews misunderstood Old Testament Prophecies of Jesus’ Coming. The Jews want to be saved from Rome, but Jesus is coming to save them from the true and greater enemies we face: sin and death. So, even though:

  • It looks like they were accepting Jesus, they were rejecting him.
  • It looks like they were honoring him, but they were dishonoring him.
  • It looks like they loved him, but they hated him.

Because they completely misunderstood Jesus’ first coming, he said:

Luke 19:44b because you did not know the time of your visitation.”

This is another way of saying they did not understand Jesus’ first coming. They completely misunderstood who Jesus was and what he was doing.

The Jews Rejected Peace When They Rejected the Prince of Peace

Luke 19:42 saying, “Would that you, even you, had known on this day (referring to the day prophesied by Daniel’s Seventy Weeks) the things that make for peace! But now they are hidden from your eyes.

The word “Salem” in the name Jerusalem is shalom, which means peace. So, there is a play on words. The city whose name means peace would not be experiencing peace. Jesus said they did not know what would make for their peace. It would have meant peace for them if they received him as their Messiah. But because they are going to reject him and call out for his crucifixion in a few days, they are rejecting the peace they could have had. Go forward five days to when Jesus was before Pilate:

Matthew 27:24 So when Pilate saw that he was gaining nothing, but rather that a riot was beginning, he took water and washed his hands before the crowd, saying, “I am innocent of this man’s blood; see to it yourselves.” 25 And all the people answered, “His blood be on us and on our children!”

You wouldn’t believe it if it wasn’t recorded, but Pilate was trying to STOP Jesus from being crucified, but the Jews were so intent on seeing him crucified Pilate believed he had to turn Jesus over to them to prevent a riot. That’s how much they despised Jesus at this moment: they were going to riot if they could not murder him.

They didn’t just ask for Jesus’ blood to be on them, they also asked that his blood would be on their children. And this is exactly what they have gotten over the last 2,000 years.

Psalm 122:6 Pray for the peace of Jerusalem! “May they (referring to the Jews) be secure who love you! 7 Peace be within your walls and security within your towers!”

The opposite of these verses has happened. It is very fitting to be reading this account with the tragic events unfolding in Israel. Every day I see new articles about the Jews being killed.

Jesus Saw the Jews’ Coming Judgment

Jesus describes happening 40 years after they reject him:

Luke 19:43 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 44a and tear you down to the ground, you and your children within you. And they will not leave one stone upon another in you

This is a prophecy of Rome’s successful siege of Jerusalem under Titus in 70 AD. Sieges were horrible experiences. All the supplies were cut off, which led to starvation and then death. Bodies would pile up which led to disease and more death. The conditions would become so bad that the people in the city would finally surrender. Jesus said the Romans would “Hem [the Jews] in on every side.” This is exactly what happened. The siege prevented anyone from escaping:

Many of those who tried to flee were crucified.

William Hendrickson, Luke, page 878

When Jesus said the Romans would “tear you down, you and your children within you,” he was referring to them even killing pregnant mothers.

The siege lasted 143 days. After that the Romans killed 600,000 Jews and took thousands more captive to be sold in Egypt or used as sport for the lions in the amphitheaters:

All hope of escaping was now cut off from the Jews, together with their liberty of going out of the city. Then did the famine widen its progress, and devour the people by whole houses and families; the upper rooms of women and infants that were dying by famine, and the lanes of the city were full of the dead bodies of the elderly; the children also, and the young men wandered about the market places like shadows, all swelled with the famine, and fell down dead wheresoever their misery seized them.

Flavius Josephus. The Works of Flavius Josephus. Translated by. William Whiston, A.M. Auburn and Buffalo. John E. Beardsley. 1895.

Jesus said they would not leave one stone upon another. This refers to the Romans destroying the temple. All that was left was one wall, which we have come to know as the Wailing Wall.

The [Roman] Emperor ordered the entire city and the temple to be razed to the ground, leaving only the loftiest of the towers…and the portion of the wall enclosing the city on the west…all the rest of the wall that surrounded the city was so completely razed to the ground as to leave future visitors to the spot no reason to believe that the city had ever been inhabited.

Josephus, History of the Jewish War, VII.1-3

The Romans built the city of Aelia Capitolina on the site of Jerusalem’s ruins, and for many years they wouldn’t allow Jews to enter, except on one day per year, the anniversary of the destruction of the temple when they could come and mourn bitterly.

The Romans did this during Passover, which allowed them to trap even more Jews who were visiting the city for the occasion. I confess this is speculative, but because Jesus was crucified on Passover, and the siege took place on the anniversary of the Jews rejecting Jesus, it is possible many Jews would back, remember Jesus’ words, and make the connection that this happened because they rejected him.

Consider the tragedy: The time of their visitation was supposed to be the greatest moment in Jewish history because they finally received their Messiah. But instead, it brought unimaginable judgment and suffering. And THIS is why Jesus wept over Jerusalem.

It was probably like this: Jesus was traveling on the donkey from Bethphage to Jerusalem. When he came within sight of the city he began to weep because he could see many of the peaceful dwellings. He knew the people were going to be killed, the pregnant women and children. He knew Jerusalem was going to become a smoldering, hideous ruin, with thousands upon thousands of the city’s inhabitants executed in gruesome ways. Others would be taken captive, and some would argue that the things that happened to them were even worse than death. Jesus could see all this, and it was heartbreaking to him.

How Did Jesus Weep Over Jerusalem?

We understand that there are different ways to weep. This is why we have so many words for weeping: crying, sobbing, whimpering, wailing, or bawling. To capture the different ways people weep, there are different Greek words.

A basic rule of Bible interpretation is to determine the meaning of words by looking at their use elsewhere in Scripture. Whenever possible, an example from the same book of the Bible is preferred, because often the author and time of writing will be the same for both uses of the word.

One word for weep, or cry, is boaō (pronounced buh-ah-oh). Let me show you two places this word is used. Look one chapter to the left at Luke 18:7. This is the parable of the persistent widow:

Luke 18:7 And will not God give justice to his elect, who cry (boaō) to him day and night? Will he delay long over them?

This is blind Bartimaeus on the side of the road:

Luke 18:38 And he cried (boaō) out, “Jesus, Son of David, have mercy on me!”

When Jesus weeps over Jerusalem, he doesn’t weep like the persistent widow to the judge, or like blind Bartimaeus to Jesus. The word used in Luke 19:41 to describe Jesus weeping over Jerusalem is the Greek word klaiō (pronounced kly-oh).

Peter denies Jesus in Luke 22:54-60, and then:

Luke 22:61 And the Lord turned and looked at Peter. And Peter remembered the saying of the Lord, how he had said to him, “Before the rooster crows today, you will deny me three times.” 62 And he went out and wept (klaiō) bitterly.

Jesus wept over Jerusalem with the same bitterness that Peter wept over his denials. It doesn’t mean that Jesus knew he did something wrong like Peter knew he did something wrong. Instead, it means Jesus experienced similar grief over the slaughter that he knew was coming to the Jews that Peter experienced over denying Christ.

Luke 23:26 And as they led him away, they seized one Simon of Cyrene, who was coming in from the country, and laid on him the cross, to carry it behind Jesus. 27 And there followed him a great multitude of the people and of women who were mourning and lamenting for him. 28 But turning to them Jesus said, “Daughters of Jerusalem, do not weep (klaiō) for me, but weep for yourselves and for your children. 

Few things, if any, in all human history would be as dramatic or moving as watching Jesus carry his cross. I think most of us probably would not even have the words to describe what it would be like to witness that event. While many of the Jews called out for Jesus’s crucifixion, these women would have been some of the few who believed, and they wept over what they saw. Their weeping was so moving to Jesus, that while exhausted from carrying his cross, he still expended the energy to tell them not to weep for him, but for themselves and their children.

Jesus is referring to the slaughter we have been talking about, that the Jews will experience in 70 A.D. He says that’s what they should be weeping over. But the point is the way they were weeping over Jesus carrying his cross is like the weeping Jesus does over Jerusalem.

Weep in Hell or Have Your Tears Wiped Away in Heaven

I know this has been a heavy post, and I want to leave you with some encouragement. I was thinking about heaven and hell, and how they are both associated with weeping:

Luke 13:28 In that place (hell) there will be weeping and gnashing of teeth.

Hell seems to be a place of constant weeping. But when God describes heaven, we are repeatedly told our tears will be wiped away:

  • Isaiah 25:8 The Lord God will wipe away tears from all faces
  • Revelation 7:17 God will wipe away every tear from their eyes.
  • Revelation 21:4 He will wipe away every tear from their eyes, and death shall be no more, neither shall there be mourning, nor crying, nor pain anymore.

People commonly quote this verse when they want to point out that there is no suffering in heaven. That’s correct and I do think it is a wonderful truth to reflect on, especially when we are suffering. But I think one of the other beautiful truths from this verse relates to the intimacy we will experience with God.

Let me illustrate it this way. Over the years that I taught elementary school, I saw students cry. Sometimes they cried because they got hurt playing, someone said something mean to them, they were upset about their grade, or they were sad about a punishment they received. I think I had good relationships with my students, but there were not very many of them that I would feel comfortable leaning in and wiping away their tears. But that seems to be the closeness we will experience with God throughout eternity.

So, it seems like we have a choice. We can spend eternity in hell where there is weeping and gnashing of teeth, or we can repent of our sins and believe in Jesus and have all of our tears wiped away.

Do you have a question or thought? If so, please let me know. I do my best to respond to each comment.

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Subscribe to Scott's Podcast
Subscribe to Scott's Newsletter

… and receive a free ebook. 
You can unsubscribe anytime.

Newsletter subscription for Scott LaPierre with Seven Biblical Insights