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The King Who Cried

February 26, 2023

The King Who Cried

Passage: Luke 19:28-44
Service Type:


LUKE 19:28-44


Good morning, River City! It’s again my privilege to preach the word of God today. I’m excited about this message today, so please pray with me and for me and we will dive right in. 


If you’re new to River City, we are going v by v, ch by ch through the book of Luke. If you’re new to the Bible, go about ¾ of the way back, and open it up. If you see names you don’t know how to pronounce, keep turning to the right till you see Matthew, Mark, Luke. 


We are about to enter Act 4 of the book of Luke. 

  • Act 1 would have been about Jesus’ birth and his growing up years. We saw an angel show up to Zechariah the high priest, and then read his prophecy that after 400 years of silence, the Lord has visited Israel, and provided redemption for his people, raising up salvation in the family tree of King David, just like the prophets talked about. We also watched Jesus, growing in wisdom and understanding, and displaying an affinity for the house of God… his Father.


  • Act 2 then would have been his public ministry, starting with his own baptism. Act 2 carried all the way through the end of chapter 9 as Jesus performs miracles, teaches, heals, etc, mostly around the region north of the Sea of Galilee, choosing his 12 apostles to be the inner circle, and then Act 3 begins as he sets his face toward Jerusalem one last time. 

  • Act 3 would be that journey to Jerusalem. During this journey, on multiple occasions, he has not just been teaching his students, but is allowing them to participate in his work, giving them authority over evil spirits, sicknesses, and so on, as they spread the word of his ministry. 


Also throughout Act 3 are Jesus’ predictions that he will in fact suffer and die in Jerusalem. In 18:31, he told the 12 disciples, listen, we’re headed to Jerusalem and everything written about the Son of Man in the prophets will be accomplished. They don’t get it yet, but he’s told them this a couple of times. 


And all along the way, Jesus has been indicating that his ministry, his life, comes with a choice. You have to make a decision about him. 


As the curtain starts to close on Act 3, Jesus tells a parable that brings piercing clarity to the fact that every person will be held accountable for their response to Jesus. We looked at this last week, and the story he told was that of a nobleman who traveled to a far country to receive for himself authority to be king and then to return. He called ten of his servants together, gave them some money, and told them to “engage in business until he came back.”


That is what Luke is referring to in verse 28 when he begins, “When he had said these things


Luke 28-34


This is a bit of a strange scene here, isn’t it? Jesus has been on the move for the past couple of weeks or so, working his way 80-100 miles from the region north of the Sea of Galilee, South to Jerusalem. And now, right before he can see the city, did his legs wear out? Why does he need to get something to ride now, and not earlier in the trip? And secondly, is Jesus stealing this donkey? Untie it and bring it. If someone goes, “hey! That's not your donkey!” You just say, “the Lord needs it.” 


Matthew, Mark, and John give additional details to this story that help make sense of what is happening here, but putting them all together, it looks like there are two reasons Jesus pauses here to get a young donkey to ride on: 


  1. Jesus is fulfilling a prophecy. Zechariah 9:9, which says ​​9 Rejoice greatly, Daughter Zion! Shout in triumph, Daughter Jerusalem! Look, your King is coming to you; he is righteous and victorious, humble and riding on a donkey, on a colt, the foal of a donkey.  Remember 18:31 – Everything written about me must be fulfilled. So Jesus is actively doing what fulfills scripture, and therefore declaring himself as the King. John’s gospel tells us that the disciples with Jesus are not making this connection right now. They might be confused too why he needs a donkey all of a sudden. It wasn’t until after the resurrection that they would realize what was happening here. 
  2. Thirdly, it’s to show that everything about to happen in Act 4, in Jesus’ final week before his death, is all intentional. There is not a single thing out of his control; not a single thing will happen that is not divinely ordered, including the conversation the disciples will have when they untie the donkey. Everything is directed and ordered, and the disciples find things exactly as Jesus has said.


35 Then they brought it to Jesus, and after throwing their clothes on the colt, they helped Jesus get on it.  Donkeys are just awkward. Even Jesus needed help getting on one.


Look back at verse 11 in chapter 19… this crowd is expecting that the messiah’s kingdom is coming right now. They expect something big is going to go down here in Jerusalem, they expect that Jesus will free them from Roman occupation and set up his throne (LMW, 388). 


Luke 19:36-38 


And in response to the crowd calling Jesus the King who comes in the name of the Lord…


Luke 19:39-40


Connecting to the story of the minas from last week, here is Jesus, with authority to be King, cresting the Mount of Olives, the Son of God returning to Jerusalem, back to his Father’s house, to see how the servants are doing… And they are completely missing it. 


The Mt of Olives is higher than the city of Jerusalem, so there’s a great vantage point from the top of it where you can look across the valley to the city. Jesus came over the top of the Mt of olives, to this vantage point, and he can see the city. He sees the walls, the Temple, the smoke from the sacrifices, he maybe hears some shouts from the marketplace, even the screams of someone being crucified by Romans, he sees Herod’s palace… 41 As he approached and saw the city, he wept for it, 


Think about what this city represents. It’s where his Father’s house is. The city where God literally shows up in a cloud in the inner room of the temple. It’s the place where God has communicated with his people for hundreds, even thousands of years; where King David and Solomon and Jehosophat and Josiah all ruled from. If you took every prophecy, every covenant promise, every mighty act of God and narrowed it all down to one city, it would be this one. 


They were expected to engage in business until the Messiah came, but for centuries, the business they’ve been engaging in was spiritual idolatry and corrupt temple worship; assimilation into Greco-Roman culture and practices, erecting temples and shrines to other gods, intermarriage with other nations and religions… it’s become a spiritual cesspool. 


God had sent prophet after prophet after prophet to this city to warn them of their actions, even allowing the city to be captured and overthrown 600 years before this moment because they have been notorious for killing prophets. They have been pushing away the weak, not taking care of the orphans and widows, and basically have the same attitude the servants did back in verse 14… “We don’t want this God to rule over us.” 


And Church, that’s what sits at the bottom of sin. We don’t want God to rule over us. Sin is not a mistake, like oops, shouldn’t probably have done that. Sin is a blatant rebellion against a holy God. We might not always think of it as that, but it is. That’s what makes sin so deadly. That’s why sin doesn’t make us bad, it makes us spiritually dead. 

  • The couple who sleeps together before they are married, the man or woman engaged in pornography, is effectively saying God’s ways for holiness, his plans for marriage and his purposes for sex do not apply to us – we’d like to handle this our own way. It's a sin against God. 
  • The person who cheats on his taxes sins against God by saying, I will need to take action to help myself financially because honesty and holiness are going to be too costly. It's a sin against God.
  • The child who throws a tantrum on the floor at the grocery store or on the playground is not a kid with a “bit of a temper.” The teenager who sulks into their bedroom, slams the door, and threatens to self-harm – both of these children are sinning against God by making their life all about themselves, and by manipulating their parents or teachers into giving them what they want. We are not born inherently good. 


At the bottom of every sin is a desire to not be ruled by anyone. I enjoy living in this country, but I think one of the greatest cultural idols of the United States is the idol of freedom. What started out as the freedom to worship without being controlled by the state, has somehow now come to mean that no one can tell us what to do or what to think, no one can tell you what gender you are, no one can tell you what to do with your body, no one can tell you who you can love, and each person is their own king or queen. If someone speaks out against it, call it hate speech and cancel them, because I am free to be who I want to be. 


All of that stems from a desire to not be ruled by anyone; worshiping the idea of throwing off all restraint and doing life on MY terms, not on God’s terms. And that, my friends, is active, self-centered, intentional rebellion against the one, true, Holy, holy, holy, most high, three in one God of the Bible, and it deserves his wrath. Oh he’s patient and kind and doesn’t get angry quickly, but sin demands his righteous judgment.


The only possible way to avoid getting crushed by the wrath of God, is that God himself would have mercy on the people who reject him. It’s the only way. We can’t do enough good things to outweigh one sin against a holy God. When God’s word calls something sin, and you or I say, “Oh, Come on, what does it hurt – I don’t see what the big deal is”, we diminish the holiness of God. We’re saying, “oh, he’s not that holy that he would be angry about this.” 


The only way out of the crushing wrath of God is if God has mercy on sinners, and praise God, mercy is on the way in the person of a middle-eastern, single man around 33 years old, trying to keep from falling off the back of a young donkey.


As he crests the Mt of Olives, and looks over this city that God loves, with so much history and significance, and his heart just breaks right there in the middle of the road. 


Some of you have watched your children or your best friend or grandchildren or spouse walk away from Jesus and choose sin or destructive behavior instead. You have some idea of what Jesus is feeling here as he weeps for the city of Jerusalem. This would not be something the crowd missed, like it was a tear rolling down his cheek. The word used here refers to full sobbing (Bock, 1560). Everyone within eyesight would have seen Jesus’ shoulder-shaking, nose-blowing, heart-broken crying. 


Not exactly what you think of when you hear the words, Triumphal Entry. I’m not sure why all of our Bible’s use that as the heading for this section. I think a better title would be: “The Unfailing-Love-of-a-Compassionate-God-Mixed-With-Anger-And-Sadness Entry” because the nation of Israel, represented by this city, has rejected him as her king. He knows that within a couple days, this same crowd that now sings his praise will demand he be crucified. 


Through his tears, Jesus says…


Luke 19:42-44


Remember Zechariah’s prophecy at the beginning of this whole thing? “The Lord has visited Israel, and provided redemption for his people, raising up salvation in the family tree of King David,” and the majority of the nation of Israel, again referencing Jesus’ story back in verse 20, has taken the Lord’s visit, his promises, the prophecies, stuffed them in a handkerchief, and buried them in the ground of the law, and missed out on what would truly bring them peace. 


Wholeness. Right relationship with God both now and in the age to come. This peace cannot be found anywhere other than submitting to King Jesus. And if you refuse his rule and reign still to this day, peace will be hidden from your life. If you refuse to turn your back on living life according to your own terms, and turn toward living life according to God’s terms, peace with God will be unavailable to you, both now and when you die. 


Again to the parable, v26 – The peace Jerusalem could have had has been missed. Even the temporary circumstantial peace they now have will be taken from them. V27, They refuse to recognize Jesus as King (God in the flesh) and instead of peace, they will receive destruction (Bock, 1561). 


Jesus’ prophecy of this destruction in verses 43-44 would come true about 40 years later in 70AD, when Jewish zealots, still looking for circumstantial peace, tried to mount a revolt against Rome. After a few years of this, Rome said enough of this… they built a siege wall around Jerusalem, forcing starvation and sickness, and soon battered through the walls flattened the city, burned the temple, and carried off everything in it. According to history, the Roman soldiers had to climb over piles of Jewish bodies as they chased the survivors out of the city (http://www.eyewitnesstohistory.com/jewishtemple.htm). Jesus’ prediction came to pass. 


Jesus sobbed for the people of the city that day because they had, and would again over the next couple of the days, reject the very person who could bring them peace.


So the question I leave you with today is this: Where have you been looking for peace? Is your peace purely political too? When those liberals are gone, then things will be like they’re meant to be. If we had this person as President. Or mayor. Or administrator. Or if the school board would do this. If I had a better house. Better car. A better job. Better kids. A different spouse. Just a spouse. Any one. A different body. More money. If I could just move to somewhere warmer, and not have to work. Mmm. That would be peace. 


See we all do it. We all look to something to bring us wholeness and peace. 


Right here, looking over the city, with crowds of people singing his praises, Jesus could have turned that donkey around, and said, hey everyone, I changed my mind. These people are sort of lousy anyway. Let’s move on out of here, go set up camp in a city where they actually want me. I’ll multiply some more loaves and fish, and we’ll just enjoy the peace and quiet.


Praise God that Jesus isn’t turned off by lousy people. Praise God that Jesus didn’t turn around that day. Psalm 145 says “The LORD is gracious and compassionate, slow to anger and abounding in faithful love…his compassion rests on all he has made.” It was that faithful love for Jerusalem and for you and for me that motivated Jesus to stay the course, to keep going into the city, where he knew he would be rejected, mocked, spit on, beaten, and crucified for the sins of those who would put their faith and trust in him, doing what was necessary for them to be saved and have peace with God.


It’s that faithful love – that commitment to redeem lousy people that we celebrate every time we participate in communion. We do this once a month here at River City, and it’s not something we do because we are saying, “God, we’re going to try to do better this month.” It’s not something we do, where we’re saying to each other, “Look how spiritual I am. I have figured out how to stop sinning.” We don’t participate in this meal because we’ve figured out how to stop sinning – we participate in this meal because try as we might, we can’t stop sinning! Daily, we still depend on Jesus’ unfailing, faithful love and compassion for those he has made. 

We take this bread and this cup to say that as the Savior sobbed that day, he sobbed for me and for you. It was my sin that he had to die for. My pride; my greed; my lust; my desire to have my own needs met; It was my search for peace and wholeness somewhere other than the person and work of Jesus that he had to die for. If I was the only sinner on the planet, he still would have had to die to cover my offenses against a holy God. And yet, with all the authority of heaven available to him, Jesus humbles himself, goes to the cross, and allows himself to be tortured to pay the price for my sins – past, present, and future – and then rises from the grave and treats me as if I’ve never sinned one time, telling me in Romans 8:1 that I will never again be condemned for what he covered at the cross. 


It’s something absolutely outrageous, called grace. And it’s available in unlimited supply to anyone who will acknowledge Jesus as Lord, confess your sin, and run home to the Father who has been waiting for you all this time. You won’t get a lecture; you won’t be disowned; you won’t be scolded for your unbelief. You’ll be hugged and kissed and lavished on because Jesus paid the bill for your rebellion. 


If you haven’t seen just how incredible that is, if you have not received this gift of grace by believing in Jesus as God’s son, believing that your sin deserves judgment and death, and believing that in Jesus, all wrongs are made right, then as we participate in this small meal together, please just pass the elements on by. This meal isn’t for you. 

This meal is for those who have said YES, PLEASE!!! to this gift of grace. If you are saying that right now, maybe for the first time in your life, maybe for the 1000th time in your life, even if you’re repenting again this morning for the same thing you repented of the last 100 times we’ve done this – then THIS MEAL IS FOR YOU! You are invited by Jesus Christ himself to participate in this today.


Kids - credible profession; seen evidence of a heart change.




Darrell L. Bock, Luke: 9:51–24:53, vol. 2, Baker Exegetical Commentary on the New Testament (Grand Rapids, MI: Baker Academic, 1996)


Leadership Ministries Worldwide, The Gospel according to Luke, The Preacher’s Outline & Sermon Bible (Chattanooga, TN: Leadership Ministries Worldwide, 1996)


Matthew Westerholm, The Triumphal Entry Before Jesus, April 14, 2019, (https://www.thegospelcoalition.org/article/triumphal-entry-before-jesus)