Why did Jesus weep over Jerusalem?

In Luke 19, as He approaches Jerusalem, Jesus weeps — knowing its coming destruction. In this sermon, Dr. Toby Holt explains why the Lord mourned over the city, and what it reveals about His heart and His warnings.

Questions this sermon answers:

1. Why did Jesus weep? Because Jerusalem had rejected Him and did not recognize "the time of your visitation" — and judgment would follow.

2. What happened to the city? Within a generation its walls were broken and its temple burned, just as Jesus foretold.

3. What does this mean for us? That Christ takes no pleasure in judgment; He grieves over the lost — and calls us to recognize the day of His visitation.

"Now as He drew near, He saw the city and wept over it, saying, 'If you had known, even you, especially in this your day, the things that make for your peace! But now they are hidden from your eyes.'" — Luke 19:41-42 (NKJV)

Speaker: In Luke 19, as He approaches Jerusalem, Jesus weeps — knowing its coming destruction. In this sermon, Dr. Toby Holt explains why the Lord mourned over the city, and what it reveals about His heart and His warnings.

A few weeks ago, we celebrated Palm Sunday, the day that Jesus entered into Jerusalem at the

outset of his Passion Week. Now, on the day that Jesus entered into Jerusalem, amidst all the palm

branches, amidst all the cries of Hosanna, the people, as they cried out and as they waved the

branches and the like, the people may have hoped that this one, or one very much like him, would

come to the city and deal with and contend with who? The Romans. When Jesus entered into Jerusalem,

you have to remember, this was during the historical context of the oppression under which the Israelites lived.

They lived under the boot of Rome.

When the people got excited because one was coming into town, when the people thought about their greatest need,

they identified that need as someone to come to deal with Rome.

The Israelites, they knew their society was corrupted.

The Israelites knew that their society was corrupted.

They knew that things were not right in their midst.

They knew that there was evil, but they identified that evil as the Romans.

And the Roman Empire that was in their midst.

Now, the good news, the good news is that Jesus did come to confront corruption.

However, the bad news was that Rome wasn't the corruption that he came to deal with.

Rome was not the corruption that Jesus was concerned about,

and Rome was not the reason that Jesus wept.

You see, the most corrupt thing, as Jesus looked out at the city,

as he approached it on that day,

the most corrupt thing that he saw in Jerusalem,

it wasn't the Roman influence. The most corrupt thing in Jerusalem was the religious practices

of his own people. If you were to describe the city of David at the time that the Messiah entered

into it, spiritually speaking, it's been said that this was a wasteland of worship. This was a place,

it had all the markings of religious society. It had a temple. It had sacrifices up to the rafters.

It had priests with tall pointy hats. It had Pharisees standing on the corners. If you were

to walk into Jerusalem, you would have said, wow, what a religious place. The problem was it was an

inch deep. The problem was it was a bunch of habits and activities and sacrifices, but with no heart

behind them. The problem was that it was God's own people who had forgotten God. They'd forgotten who

He was, what he said, what he wrote, and what it meant for them. And the proof that they'd forgotten,

the proof that their hearts were a million miles away from God, is that within a week of his son

entering into the city, they killed him. And that was Jerusalem. It's not like he went among the

ammonites, the Canaanites, the Hittites, the Jebusites. It was his own people. And they killed

Him within a week of him setting foot. When he looked out the city, he did not weep a single

tear because of Caesar. When he looked at the city, he didn't weep a single tear because of

roman oppression. When he looked out of the city, it wasn't paganism, it wasn't secularism, it wasn't

humanism, it wasn't the media, it wasn't any number of other things that caused him to weep. It was

the spiritual condition of his own people it was flatlining and they knew it not see if you were an

israelite in the first century you probably didn't share Christ's tears if you're an Israel in the

first century you thought you were doing fine that God was well pleased with you it's the Romans that

He didn't like that would have been your perspective God loves us God is pleased with us we're doing

great all things considered it's the Romans it's the Romans he doesn't like if God's gonna be angry

somebody he'll be angry with Rome well yes God was angry with Rome and in due time he would deal

with Rome but not before he used Rome to destroy Jerusalem to burn it to the ground the city the

people the temple within it this morning we're going to consider that this morning we're going

to talk about this and one of the observations we're going to consider is this that the greatest

threat to Israel, if you had asked an Israelite of the first century, they would have said Rome

or some other nation or some other people or something like that. Wrong. The greatest threat

to first century Israel, the greatest threat to fifth century Israel, the greatest threat to

Israel in David's time, Solomon's time, Ahab's time, Christ's time, the greatest threat to them

was not some other nation. It was not some other army. It wasn't the power of the Canaanites. It

wasn't how tall Goliath was. It wasn't how deep the Red Sea ran. It wasn't how wide and high Jericho's

walls were, the greatest danger, the greatest threat, the greatest opposition to Israel was

not external to Israel. The greatest danger is what would happen if they forgot God and how God

promised he would respond. This is true in our day as well. In a moment, I'm going to read verse 41

and we're going to work our way through it, but I'll say this at the outset. This is true in our

day as well. In our day, we could think that, you know, the greatest problem that we have in the

church wow it's the politicians that we don't like it's the media if only the media was better

maybe secularism humanism some other ism maybe it's what they're teaching college or what have

you maybe that's the problem I can assure you I can assure you this a strong church could deal

with all that if God could sustain his people if he could part red seas if Goliath could be

knocked over with a stone if the Canaanites could fall before the Israelites no matter how numerous

they were, if God could take and preserve and protect his people across all those centuries

and all those opposition and do everything they said he would, if that was true in his day,

then in our day, a strong church can absolutely deal with humanism and secularism and paganism

and atheism and opposition and politics and the media or what other forces might collaborate

against us. A strong church can withstand all that. But what if the church is not strong?

What if just like first century Israel, the visible church has the appearances of religiosity, stained glass pews and all that, but is really Ichabod, the glory has departed.

When or if that should happen to a church, a denomination, when or if that should happen?

When the visible church loses its sight on its Savior and undermines or subjugates its doctrines to something lesser, something worldly.

When a church does that, when a nation does that, when a denomination does that,

it doesn't have to worry about man anymore.

It has to worry about God.

That, that's what Jesus knew was the danger, the sword of Damocles that hung over Jerusalem.

That was the danger, the wrath of God due to sin.

Let's look at verse 41 and work our way through it.

Verse 41, now, as he drew near to the city, he saw the city and he wept over it.

You know, across the pages of history, the greatest friend that you could ever want is who?

I heard Jesus. I'd also accept God.

The greatest friend across the pages of history, the greatest friend that the people could ever have or ever want was God.

Every time they faced some opposition, some wall too high, some giant, some army, what have you,

so long as the right man was on their side, so long as God was with them, they could face and overcome anything.

The greatest friend you could ever have, then or now, as a church or as an individual,

the greatest friend you could ever have is God.

But guess what?

The greatest enemy you could also have is God.

You see, when God's people walked with him in days past,

Scripture says that they were blessed beyond measure.

Things went well for God's people when they listened, when they obeyed.

If you look back at the books of the Kings and the Chronicles and Joshua and Judges and the like,

when you look at these historical records, you see something.

You see that when the people were faithful, when they read the book and learned from the book and

talked about God and followed his laws and did what he said and didn't do what he told them not

to do, when they were walking with God, things went well. There was a one-to-one correlation

between their faithfulness and how well things were going on in the world around them. But the

reverse is also true, that when they turned from God, when they turned from God, things did not

go well for them. The thing is, as often as that cycle repeated, just go to the book of Judges

alone and you'll see that cycle time and time and time again. As often as you would think that they

would have learned their lesson, as often as you would think that this time they got it, this time

they'll be faithful now that they've returned to the Lord. Well, the thing was, the hearts were

deceitfully wicked and hearts would turn and they frequently did. There was times in the Old Testament

where despite having God's word before them, despite all the privileges of being God's chosen

people, the kings and the leadership just threw all that out the door. There was a king, his name

was Jehoiakim. Now Jehoiakim was one of those many kings that we call one of the bad kings, one of the

naughty kings of Scripture. Now this king, this king, he had Scripture read to him. So he came in

with a scroll and began to read God's word. And you know what he did? Instead of just plugging up

His ears or leaving the room he took it one step further he took out a knife he took that knife and

He began to slice the scroll into strips he took a knife and he cut through the Word of God and then

and then as if that wasn't bad enough then he took the strips that he had cut and he threw them into

the fire in a microcosm that's what God's people have been doing on and off for centuries and they

had been doing it in Christ's own time as well. They still had a temple. They still had sacrifices.

They still had men in tall pointy hats. They had that. And yet God was not with them to the degree

that they killed his son when he walked into town. That was the spiritual condition. And they knew it

not. They didn't understand how bad things had got. They thought things were okay. They weren't.

They thought things were fine. They were not. And they did not know the hour of their visitation.

They did not know the hour of their visitation.

And so Jesus wept.

Verse 41, he draws near and he weeps.

Let's look at verses 41 through 44.

Now as he drew near, he saw the city, wept over it, saying,

if you had known, even you, especially in this your day, the things that make for your peace,

but now they're hidden from your eyes.

For days will come upon you when your enemies will build an embankment around you,

surround you, close you in on every side, and level you, your children within you, to the ground.

I will not leave one stone

one stone upon another

because you did not know the time of your visitation

if you had only known the things that make for your peace

if there's one thing that the Israels knew very little about over the years

it was peace. God had promised them that when they were faithful, that things would go well.

This was the nature of the covenant. God had called His people out, out of this world and

promised them that if they were faithful, if they listened to their word and inclined their steps to

follow the word, that things would go well for them. God had promised them that when they were

faithful, they would have peace and rest all around from their enemies. Conversely, disobedience would

lead to war, and persecution, and oppression, and exile, and death. Over the years, Israel routinely

picked door number two. Over the years, Israel routinely picked that which they ought not,

even though they knew better, and even though history and Scripture told them, told them what

would happen if they turned their back against God. In fact, it told them what would happen if

not only did they ignore God, but they became rebels and enemies of God. You know, the war is

and contentions that they had with the other nations, Philistines and Moabites and Ammonites

and Hittites and the like, that was nothing. That was nothing compared to what would happen if they

were so intent on making God their adversary. And if you kill his prophets, if you reject his word,

if you elevate traditions over Scripture, as was the norm in Christ's day, if you kill the prophets,

you reject his word, you elevate traditions over Scripture, if you kill his own son, you can rest

assured there are consequences. It's those consequences that Jesus is anticipating in

verses 41 through 44. And it brought no joy to his heart to know they were coming. Make no mistake,

this is part and parcel why he wept. It brought no joy in his heart to know what was coming,

what the results of their decisions would be. He had longed to gather them close like a mother hen

gathers the chicks close. That was his desire, but they would have no part of it. So because of

their actions, because of their animosity toward the throne of heaven, he said this in verses 41

through 44. The days will come when your enemies will build an embankment around you. They will

surround you. They will close you on every side. They will level you and your children within you

to the ground. They will not leave you one stone upon another because you did not know

the time of your visitation. 70 AD, as most of us know, 70 AD, within the lifetime of many who

heard him, these verses would be fulfilled. 70 AD, Titus Flavius, the son of the Roman emperor

vespasian he attacked first of all the forces surrounded the city then after starving them out

a bit they conquered the city and finally they burned the city slaughtered the people and in the

midst of the city even the temple even God's own temple burned as well consider that for a moment

the temple of God the same temple that the people would cry out the temple Lord the temple Lord the

temple of the Lord, that same temple burned at the hands of who? At the hands of He who it glorified,

He who it typified. It burned on His watch, at His own volition. Why would He do that?

This is His temple. You would think of all the things He'd preserved, that might have been on

the list. Why did He burn it? There's more answers to that than we have time to describe, but at the

very least, He burned it because the people had desecrated it. The people had a form of godliness,

we talked about that earlier. They had the form. They had the accoutrements. They had the scrolls and Scriptures and temple and sacrifice and all that.

They had the form of godliness, but they were clearly denying the power of.

They'd been given the Scriptures, but they subjugated that to traditions.

The people had sacrificed animals all day long up to the heavens, and yet they couldn't recognize the Lamb of God when it walked in their midst.

John the Baptist got it. The rest didn't.

The people had the appearance of religiosity, but they had lost their religion.

And as a result, because of all that, which had been inculcated from the leadership over years on down,

because of all that, the people could not recognize, could not sense, could not perceive

the Son of God, God incarnate, God in the flesh, right when they were looking in the eyeball.

Their hearts were dead. Their hearts were dead.

And this is the sin, this inability to recognize.

This is the sin that Jesus said would cost them.

It says, not one stone will be left upon another because you did not know.

The hour of your visitation. Among all the other reasons he could have gave,

that was foremost. The temple's going down, the city's

going down, and the reason it's going down

is because you did not know the hour of your visitation. Let me ask

you a relevant question. Let me ask you a thinking question.

If God was willing to burn his own temple to the ground, if God was willing to burn

His own temple to the ground when his glory was on the line, when his word was being disparaged and his holiness

impugned. What nation, what institution, what denomination do you think can pursue a similar

trajectory and avoid a similar fate? Let's look at verses 45 and 46. Then he went into the temple

and began to drive out those who bought and sold in it, saying to them, it is written, my house,

my house is a house of prayer, but you, you've made it a den of thieves. You know, when I was

younger, I was fascinated with this text. And it's usually because when you read about Jesus,

He is so patient and kind and gentle. And he goes and he visits with the sinners and the tax

collectors. And he dines with folks that were on the fringes of society. That's been nice,

who were outside the fringe of society. He reached out to them. He was caring. He fed the 5,000. He

healed the lepers. He did all that stuff. He was so wonderful and patient. And because that's true,

any moment you see when he demonstrates anger stands out

because that didn't seem to be the norm of his interaction with his people.

Well, here he demonstrated anger.

And because it is somewhat rare, it must be really important.

It must be really a big deal.

What prompted Jesus to go into the temple and drive out those within it?

Well, if you want to understand this event here in verses 45 and 46,

I want you to understand something you might not be familiar with.

This is not the first time he had done this.

You know, you might have thought, you know, growing up, you hear the stories of Jesus going into the temple.

You might have thought that was like some one-off event.

One time he goes in and he chases them out.

Not so much.

This happened twice.

If you go back, if you were to look at John 2, the very start of John's Gospel,

you would see what most Reformed scholars believe is a separate incident by which he did roughly the same thing.

In John 2, we read these words.

The Passover of the Jews was at hand, and Jesus went up to Jerusalem.

And in the temple, he found those who were selling oxen and sheep and pigeons,

and he found money changers sitting there.

And making a whip of cords, he drove them out of the temple with the sheep and the oxen.

And then he poured out the coins and the money changers.

He overturned the tables, and he told those who sold the pigeons,

take these things away. Do not make my Father's house a house of trade.

And his disciples remembered that it was written.

Zeal for your house will consume me.

Zeal for your house, zeal for worship,

zeal for what we're here to do

would consume him to the point where he'd get angry.

When he'd get angry, when those would dare

to cast that worship underfoot,

make it a marketplace, den of thieves.

Now, we don't have time to talk at length

about what the money changers were doing.

The simplest explanation is this,

that the reason the money changers were there

was that if you went to the temple and you wanted to provide an offering,

make a tithe and the like, you did it in Jewish money.

Well, you typically had Roman money, so you exchanged it.

However, the people who exchanged it with, they took a piece of the action.

So in effect, they were claiming a percentage off of what was otherwise people's tithes.

And that decision to make a marketplace, that was bad enough.

But in Jesus' mind, the bigger problem was where they did it.

It wasn't just that they were doing that.

It was where they were doing it.

They were doing this.

The outer court of the temple. They were doing it in the place that was to be devoted

to prayer. They had repurposed it.

They had repurposed it for something carnal and worldly. Something

pragmatic that they thought they needed and would help them out in order to go about their business.

Well, Jesus says, no! Zeal for your house, O God.

Zeal for your house, my Father, will consume me. Jesus was zealous

for worship. This is a God who took out Nadab and Abihu when they made strange

fire. Don't think that God is cavalier towards how he's worshiped. He's not. And Jesus, the time in

which he was angry was when worship was besmirched by the people, treated as something other than it

was, something carnal. He had zeal, zeal for the house of God. I wonder, do you think as you cup

your ear to the greater church world outside these doors, as you cup your ear to what you hear,

whatever that is, do you detect the sounds of those who are zealous for the house of the Lord

or, or those who are pragmatic. Much of what is going outside within the broad scope of the

evangelical world is not zeal for the house of the Lord, but pragmatism and the elevation of

worldly thoughts, worldly deeds, worldly doctrines. And I can tell you with confidence that when that

happens, it arises like a foul stench before the nose of our God. We have brought money changers

into the temple. Let's look at verse 47-48. And he was teaching daily in the temple. But the chief

priests, the scribes, and the leaders of the people sought to destroy him. And they were unable to do

anything, for all the people were very attentive to hear him. You know, there's a cruel irony that

stands on verse 47. You know, if you had said that the Messiah would come into first century Israel,

you would have thought, I'm sure they would have thought, that the people most likely to recognize Him and love Him and worship Him and the like, that it would have been priests, right?

You would have thought that if Jesus came in, the Messiah had come in, that the first people to recognize Him for who He was and adore Him as such would have been the priests.

Because they were the ones most often in the Word, the pastoral equivalent in that day, that that would have been the ones who would have figured things out.

You know, scribes and priests and the leadership, the religious elite that they would have figured out and then they would have passed that on to the laity.

That's not what we see here.

What we see here is a cruel irony that the very people who you would have thought would be the first to recognize and worship and bow down to Jesus were the ones who wanted to destroy him.

If you were Jesus, how frustrating would that have been?

You know, you're the high priest, right?

You're the great high priest.

You come in, and these guys, these other priests, these guys whose office you are the ultimate fulfillment of, not only don't recognize you, but want you dead.

For Jesus, this had to be frustrating.

To know that the leadership was where the problems were gestating here in Jewish society.

Again, as a side note, this sort of corruption of ecclesiastical leadership,

it's not an accident or a coincidence.

If you're the evil one, you're no dummy.

You know you start at the top.

You work your way down.

That's certainly what happened here.

Now, we could linger on that observation.

We could linger on the errors of the religious leaders.

But I'd rather linger as we close this morning on what we see in verse 48 that's encouraging.

What you might call the spiritual hunger of the people who were drawn to him.

Even as the leaders wanted him dead, there were those who had a spiritual hunger

and they were drawn to what he was saying.

So verse 47 says that the leaders sought to destroy him.

But verse 48 says that the people, people like you and I, were attentive to hear him.

You know, there was a lady at one of my previous churches who had terminal cancer.

You might have thought that cancer would have shrunk her faith.

She was relatively young, 40s, and you might have thought that the cancer would have shrunk her faith.

You might have thought that the diagnosis would have left her hopeless because she didn't have a long time frame to work with.

Well, she didn't have a lot of time, and she did have a lot of reason to be bitter.

And yet, what I found in talking and counseling with this woman in between chemo trips and the like,

was that even though the trajectory of her health hadn't changed,

at the same time, the trajectory of her hope and her relationship with God improved each day.

God used a trying circumstance, a trying time to bring her closer to Himself.

And the best way I can describe is to say that she had this gnawing hunger to know more about her Maker, to understand Him better.

In the same way in the first century or our century, there's a lot of people whose circumstances are good and there's a lot of people whose circumstances are bad.

God can use whatever circumstances, and in my experience it's oftentimes bad ones, to bring people closer to Himself.

To bring people closer.

They realize they're hungry, especially in the midst of trials.

We understand we're hungry, and we understand that there's nothing outside these doors that can fulfill us.

Well, when Jesus spoke to those with this sort of spiritual hunger, in verse 48,

what he said resonated with them.

Jesus was saying something that none of the priests were saying.

He was saying something none of the Pharisees were saying.

He was giving dying, hurting, lost people words of hope and encouragement.

Even in the midst of Roman oppression and opposition,

even in the midst of whatever the world might throw at their door,

He was extending to them a lifeline.

And many, in the midst of their hurts and their pains,

they reached out for it and they grabbed it.

When Jesus spoke, he not only spoke words that were true,

but he spoke with the authority that comes from on high.

And when he told people, in my Father's house are many mansions.

When he told people he was going to prepare a place for them.

When he told people of that undiscovered country.

When he told people that a day and a time was appointed when all tears would be wiped away.

In the midst of the tears they were crying then, they gave them hope.

They knew that the story ends well.

They knew that no matter what would happen, whether it was in 70 A. D., 90 A. D., the 21st century,

that God's on his throne and he still loves sinners and calls them to himself.

Jesus called them to himself.

And when he opened his mouth, people came from miles and miles around to listen.

Into the darkened world in which they lived, under the boot of Rome, came light and truth.

And they seized upon it because in the crucible of their pain, to borrow an old term,

the crucible of their pain, here was someone who not only cared about them, cared for them.

He not only had sympathy for what they were going through,

He had empathy as one who lived amongst them and who would die for them.

There's no one else that loves you the way that he does.

Again, as we close here, Jesus said, he said things like this in Matthew 5.

He said, blessed are the poor in Spirit.

No Pharisee ever said those words, but Jesus did.

He said, blessed is the poor in Spirit,

for theirs is the kingdom of heaven.

Blessed are those who mourn.

Blessed are those who grieve, for they shall be comforted.

Blessed are the meek, for they shall inherit the earth.

For those who are grieving, those who are hurting today,

this is medicine, good medicine.

It does our hearts well to know that grieving is not the end.

Hardships are not the end.

The pain of today is not what tomorrow will hold.

Our grieving, according to God who made the heavens and the earth, our grieving will end.

Our comfort will be restored.

Our losses, our losses will expire, and they will result in reunions with those that we've lost.

The poor in Spirit will be raised up, strengthened, encouraged.

He's doing so today in small ways.

It will reach a culmination, and it's not that far off.

That's exciting.

Verse 48, Jesus called hurting people close.

They came and listened.

This morning, the question is, is he calling you?

This morning, are you aware of a spiritual hunger within you?

Hunger perhaps to turn to him for the first time or perhaps to return to him from afar.

Whatever the case, you will find him just where he's always been.

His arms extended towards you.

Let's pray.