Matthew 19:16-20:16

16 Now behold, one came and said to Him, “Good Teacher, what good thing shall I do that I may have eternal life?”

17 So He said to him, “Why do you call Me good? No one is good but One, that is, God. But if you want to enter into life, keep the commandments.”

18 He said to Him, “Which ones?”

Jesus said, “ ‘You shall not murder,’ ‘You shall not commit adultery,’ ‘You shall not steal,’ ‘You shall not bear false witness,’ 19 ‘Honor your father and your mother,’ and, ‘You shall love your neighbor as yourself.’ ”

20 The young man said to Him, “All these things I have kept from my youth. What do I still lack?”

21 Jesus said to him, “If you want to be perfect, go, sell what you have and give to the poor, and you will have treasure in heaven; and come, follow Me.”

22 But when the young man heard that saying, he went away sorrowful, for he had great possessions.

23 Then Jesus said to His disciples, “Assuredly, I say to you that it is hard for a rich man to enter the kingdom of heaven. 24 And again I say to you, it is easier for a camel to go through the eye of a needle than for a rich man to enter the kingdom of God.”

25 When His disciples heard it, they were greatly astonished, saying, “Who then can be saved?”

26 But Jesus looked at them and said to them, “With men this is impossible, but with God all things are possible.”

27 Then Peter answered and said to Him, “See, we have left all and followed You. Therefore what shall we have?”

28 So Jesus said to them, “Assuredly I say to you, that in the regeneration, when the Son of Man sits on the throne of His glory, you who have followed Me will also sit on twelve thrones, judging the twelve tribes of Israel. 29 And everyone who has left houses or brothers or sisters or father or mother or wife or children or lands, for My name’s sake, shall receive a hundredfold, and inherit eternal life. 30 But many who are first will be last, and the last first.

20 “For the kingdom of heaven is like a landowner who went out early in the morning to hire laborers for his vineyard. 2 Now when he had agreed with the laborers for a denarius a day, he sent them into his vineyard. 3 And he went out about the third hour and saw others standing idle in the marketplace, 4 and said to them, ‘You also go into the vineyard, and whatever is right I will give you.’ So they went. 5 Again he went out about the sixth and the ninth hour, and did likewise. 6 And about the eleventh hour he went out and found others standing idle, and said to them, ‘Why have you been standing here idle all day?’ 7 They said to him, ‘Because no one hired us.’ He said to them, ‘You also go into the vineyard, and whatever is right you will receive.’

8 “So when evening had come, the owner of the vineyard said to his steward, ‘Call the laborers and give them their wages, beginning with the last to the first.’ 9 And when those came who were hired about the eleventh hour, they each received a denarius. 10 But when the first came, they supposed that they would receive more; and they likewise received each a denarius. 11 And when they had received it, they complained against the landowner, 12 saying, ‘These last men have worked only one hour, and you made them equal to us who have borne the burden and the heat of the day.’ 13 But he answered one of them and said, ‘Friend, I am doing you no wrong. Did you not agree with me for a denarius? 14 Take what is yours and go your way. I wish to give to this last man the same as to you. 15 Is it not lawful for me to do what I wish with my own things? Or is your eye evil because I am good?’ 16 So the last will be first, and the first last. For many are called, but few chosen.”


I remember when I was a young boy, my father told me about how the Bible said the last shall be first, and the first shall be last. I am certain he explained what it meant to me, but I was terribly confused. It seemed like a riddle. I had no idea what it meant. What does that phrase mean? What is Jesus telling us about His kingdom. There is something about an underdog story that everyone loves. It is innate to human nature. We love David and Goliath. Some day we’ll love to tell the story of how the tiny Minnesota Twins finally defeated the mighty New York Yankees in the playoffs. That is sort of what this inversion looks like. The mighty powerful and wicked who are at the top are going to be thrown down. And the lowly and despised will be raised up. The last being first and the first being is last is God turning the tables on the world. And in our passage today, Jesus gives us a glimpse of what that looks like.

The Rich, Young Ruler (v. 16-26)

Remember the setting of our scene here, Jesus has left Galilee, He has left the rural backwater, the flyover country, and is in Judea, the center of wealth and power in Israel. This is where the political and religious elite in Israel were at. So, it is no surprise that one young man from this wealthy elite comes and finds Jesus as He is in Judea. And he has a question for Him. “Good teacher, what good thing must I do that I may have eternal life.” “Hey, Jesus, there has to be some giant good deed I can do, right? Some monumental feat that will earn it for me and them I’m good, right?”

Somewhat surprisingly, Jesus does not directly address the young man’s error. He doesn’t tell him “listen, pal, you’re never gonna be able to earn it.” He doesn’t do that, not directly, anyway. Instead, what does He do? He takes issue with the young man calling Him “good,” and He tells him the way to life is keeping God’s commandments.

The young man presses Him. “Which commandments?” Is he asking because there are some he’d really rather not keep? Or because he thinks Jesus might tell Him one is more important than another? Jesus then tells him commandments 5-10. But He makes a slight change to the tenth commandment. Or rather, He applies it. What does a commandment to “not covet” mean if not to love your neighbor as yourself rather than loving your neighbor’s stuff and hating your neighbor. That is the heart of the commandment. Love those around you as much as you love yourself.

Hearing this list, the young man tells Jesus that he has kept the commandments. Most people at this point “oh no you have not! All have sinned.” Yes, that is true, but Jesus doesn’t go there. The rich young man has demonstrated that he has the righteousness of the Pharisees. He has kept the commandments. But Jesus wants this young man’s righteousness to exceed the righteousness of the Pharisees.

He tells the young man if you want to be perfect or complete, go, sell everything, give to the poor and invest your great wealth in heaven. And then come, follow me. And how does the young man respond? Does he give away everything he has to follow Jesus? No, he goes away sorrowful, because he loved all his stuff.

Jesus tells His disciples that it is hard for a rich man to enter the kingdom of heaven. He doubles down and says it is easier for a camel to go through the eye of a needle than for a rich man to enter the kingdom of heaven. In an attempt to lessen the force of the statement, many people cite some gate in Jerusalem as “the needle’s eye” but as far as anyone can tell no such thing existed. Jesus is telling his disciples that stuff and money make it extremely difficult for people to repent and believe. Wealth brings power, and comfort, and ease of life. That is not something people usually give up readily.

Ironically, this passage is one that is so often used by extremely envious and covetous people to justify their hatred of their neighbor. So, before we go any further, Jesus is not saying that everyone with wealth has to go sell it all and live the rest of their life in poverty. He is not saying that people who have worked extremely hard all their lives are not allowed to enjoy nice things with the fruit of their labor. What He is saying is that wealth makes repentance and faith difficult.

Jesus’s saying makes His disciples astonished. These are not rich men, but they wonder how anyone can be saved. Jesus tells them with men, it is not possible. That camel is not gonna fit through the needle’s eye. But with God, it is possible. And we see this throughout the New Testament. There are many wealthy people who come to faith. Many leaders in the church in Acts had large wealthy households. But we also see what wealth does to people with Ananias and Sapphira, who say they have sold everything and given it to the church, but lied and are struck dead. Being rich can be a great blessing with which you can do so much to help many people, but being rich can also be a great danger to your soul.

Treasure in Heaven for Christ’s People (v. 27-30)

Peter tells Jesus that, unlike the rich, young man, the disciples have left everything for Jesus. He wants to know if they will be rewarded. And Jesus tells them that in the regeneration, those who follow Him will sit beneath Him. The disciples specifically will rule over the twelve tribes of Israel. And everyone who gives up something for Jesus’ sake will receive that back a hundredfold. If that rich young ruler gave up his billions, in the regeneration, he’d have hundreds of billions. Instead, he who was first will be last. 

The Parable of the Vineyard (20:1-16)

Jesus then tells a parable which fleshes this out. The kingdom of heaven is like a landowner (a rich man!) who went out before dawn to get laborers. He offers a denarius to them for a days work and they say great! Then he goes out a few hours later and finds more laborers and tells them he’ll give them a decent wage. He continues this throughout the day. Then he finds some men without work right before dusk and offers them a fair wage. Then it came time to pay them, and the ones who only did an hour of work got a denarius. And a denarius to those who only did 3 hours work. Then a denarius to those who did 6 hours, 9 hours, and then finally it got to the guys hired for the full day, who had agreed to a denarius, got paid. And they grumble because they worked all day and only got a denarius. The vineyard owner told them they agreed to it, and it is his money and he can give it to whomever he wants. The issue is with them, not him. They are filled with greed and envy.


That is what Jesus means by the last being first and the first being last. Everything becomes inverted. Those at the very top, who appear to have it all will come away with nothing, while those at the very bottom, who appear to have nothing, will come out on top. In the context here, the elite of Judea, those who oppose Jesus and who lead Israel to sin and will engineer His murder are the first-hour men. The rich young ruler represents them. God has been abundantly gracious to them, yet in the end they resent Him. And the even greater irony for them and the rich young ruler in particular is that all their wealth, all the riches at their command within one generation will all be taken from them. The historian Josephus tells us about the horrors of the destruction of Jerusalem, that many rich Jews would swallow their gold and try to sneak through the Roman lines only to be caught by the Romans who would then rip open their bellies while they were still alive to get their money. The first really did become last. All of it was very soon going to be taken from them. The rich young ruler desperately wanted to hold on to what he could not keep and did not care that it cost him what he could never lose.

But the disciples are like the last-hour men, men who had nothing, who had been unemployed all day but now have been blessed by the generous landowner. They have given up everything for Jesus and will be rewarded for it. Men who had very little, now become the men on the very top.

The kingdom of heaven inverts the kingdoms of men. Those at the top in worldly kingdoms are often last in the kingdom of heaven and those at the very bottom of worldly kingdoms are at the top in the kingdom of heaven.

In our own day this is true as well. There are many people at the very top in politics, in business, in entertainment, in academia who have nothing but disdain for Jesus Christ and His people. It is very hard not to notice it. The things of God are routinely mocked, if they are thought of even at all. To be a Christian today is to be low-status. You are not cool or well-thought-of or even respected for sincere faith in Christ. If anything you will be despised. But what does Jesus say to the disciples? Whatever those who believe in Him lose for His sake, will receive it back 100-fold in the regeneration. This certainly includes the mockery and shame heaped on you for believing in Jesus. Whatever indignity you suffer for Christ’s sake you will receive back 100x in glory in the regeneration. Do you ever think about it that way? That all that you give up for Jesus, all the things you hand over to Him that the rich, young ruler would not, you are going to get back in a massive return, if you have faith. Trusting in Christ is literally the investment of a lifetime. But it is an investment that will pay off. Because Jesus Christ rose from the dead. So trust in Him, believe in Him, devote your life to His kingdom, and you will have treasure stored up in heaven. In the name of the Father, the Son, and the Holy Spirit. Amen!