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Matthew 19:16 – 20:34 – The First Who Are Last

The Men Who Turned the World Upside Down Are Come Here Also!

When Paul and Silas preached the good news of Jesus in the pagan city of Thessalonica in the 1st century, their opponents stirred up a mob who dragged a recent convert into court with the cry, “These men who have turned the world upside down have come here also!” (Acts 17:6). If we took seriously what Jesus says in Matthew 19:16 – Matthew 20, people would believe we had turned the world upside down as well.

Jesus Upends Conventional Wisdom

But many who are first will be last and the last first. – Matthew 19:30

So the last will be first, and the first last. – Matthew 20:16

But whoever would be great among you must be your servant, and whoever would be first among you must be your slave, even as the Son of Man came not to be served but to serve, and to give His life as a ransom for many. – Matthew 20:26-28

He seems to speak in riddles and enigmas. What does He mean that the first will be last and the last be first? Is He planning a revolution that will make “the haves” into “have-nots” and vice versa? How will the slave be first among you? Is He planning a society that rewards losers?

Even in our Christian ears, we do not really believe He meant to say what it sounds like He said. We live so much in this age and are influenced by it so much that what Jesus said sounds foreign to us.

It sounded that way to those who first heard it as well.

The Rich Young Ruler

Jesus & the Rich, Young Ruler

A young man who seemed to have it all came to Jesus with an important question: “Teacher, what good deed must I do to have eternal life?” Sounds serious, doesn’t it? “Lord, let me know some great feat I can accomplish for You that will bring me eternal life!” Tell me how many tracts I need to pass out – or how many orphans I need to care for – or ….

What Jesus told him just blew him away – literally. It was so radical that the enthusiasm of the young man evaporated. What’s more, Jesus’ disciples were also astonished, as they asked, “Who then can be saved?” If it is harder for a rich man to be saved than for a camel to go through the eye of a needle, who indeed can be saved?

The point is that the rich, young man wanted to save himself by something he would do. That was impossible. Salvation is by God’s gift, not our doing. What is impossible for us is possible for God.

Jesus closed that conversation by saying, “But many who are first will be last, and the last first.”

Workers in the Vineyard

He immediately launched into a parable to explain that. We call it the Parable of the Workers in the Vineyard. The owner of the vineyard certainly did not seem to act in a rational way. One group of workers was there all day working for an agreed wage. You might say they had a labor contract. Others came later, some even as late as the last hour of the day. These later ones worked only with a promise from the owner that he would give them “whatever is right.”

When the end of the day came, he lined them up to receive their pay going from the late arrivals to the first to begin. He paid the late comers exactly what he had contracted to pay those who started early. When the first to begin came up for their pay, he gave them what he had contracted.

Are you surprised that they were disappointed? After all, they worked all day in the heat – and some of the others worked only one hour. Yet, the owner of the vineyard paid all of them the same. I expect I would have been asking about it as well!

Jesus also closed this parable with the same saying: “The last will be first, and the first last. For many are called, but few chosen” (Matthew 20:16).

The point of the Parable is that God does not run His kingdom according to human expectations. The later workers worked by faith in the promise of the owner. The first worked by negotiated contract. The later workers were rewarded by the good will and grace of the owner; the first workers earned what they were paid. Which is better? To try to earn salvation (like the rich young man in Matthew 19), or to throw yourself on the grace and mercy of God, trusting Him to do what is right?

Let Us Sit at Your Right & Left in Your Kingdom

Then, the disciples themselves gave Jesus another opportunity to teach His upside-down way of doing things. Two of them came with their mother to ask for special places in the kingdom at the right hand and left hand of the Lord Himself.

When the other ten heard about it, they were indignant. Do you blame them? Jesus taught about greatness through submission. The greatest of all must be the slave of all.

Jesus used Himself as the example and standard of this principle. The disciple is to be like his Master. We are to follow Jesus – bearing a cross. Paul developed this teaching in Philippians 2:5-11. “Let this mind be in you that was also in Christ Jesus.” He emptied Himself of divine glory to become a man – and a servant among men who became obedient to the point of death on a cross. For this reason, God exalted Him.

He set the pattern. He became the most highly exalted because He became the suffering servant of all. So must I, if I would be His disciple.


  1. Most do not live as if they believe Jesus meant what He said in the section covered in this lesson? How would our lives change if we took these things seriously?
  2. What did the rich, young ruler expect Jesus to tell him? He said he had kept all the commandments. Did he expect Jesus to tell him he was a good boy and that everything was hunky-dory for him? Or what?
  3. What was so shocking to the disciples about what Jesus said when the young man turned away? Does it shock us that such a morally upright, religious leader did not have eternal life?
  4. For many years, I looked at the different times to begin working in the vineyard in the parable as the time of life in which one obeys the gospel. A few years ago, I began to see it as a parable of God’s grace and man’s trust in God. How do you see this parable? Where are you in it?
  5. The parable again has the last being first and the first last. Does this parable help you understand this paradox? If so, how does it help?
  6. Why did Jesus say the ways of the Gentiles, who pushed themselves ahead of others, were not to be the way of His disciples? How do His disciples become great?




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