Before we read, I want to establish the context. A young man approaches Jesus in verse 16, asking about what it takes to inherit eternal life. After a bit of conversation, Jesus ends up telling the man to sell his possessions and give to the poor. Unwilling to do so because of his riches, the young man leaves sorrowfully.

Now, let us read Matthew 19:23–20:16.

Choose your reward.

In 19:30, when Jesus speaks of the “first” who will be last, He means those who are rich, successful, and well-to-do in this life. Many people will receive their reward in the present age. They have chosen when to be “first,” and in the resurrection, they will be last.

By contrast, the poor fishermen of Galilee, so despised by their own society and culture, will be the greatest in the Kingdom of God, as will anyone who sacrifices contemporary joys for Christ’s sake.

The theme of sacrificing this life for a future life occurs throughout Jesus’s preaching. He consistently calls us to reject pride and self-fulfillment in the here-and-now. Instead of doing your prayers and alms to be seen of men, conduct them privately, so that God will be the one to reward you.

“Blessed are you when people insult you and persecute you, and falsely say all kinds of evil against you because of Me. Rejoice and be glad, for your reward in heaven is great; for in the same way they persecuted the prophets who were before you.” (Matt 5:11–12)

“Beware of doing your righteousness before men to be noticed by them; otherwise you have no reward with your Father who is in heaven.” (Matt 6:1)

Notice that this is the core of what Jesus told the rich young man as well. The young man chose for himself what king of reward he wanted: a physical reward.

I think perhaps the best verse to remind us of this principle is Matthew 6:19–21.

“Do not store up for yourselves treasures on earth, where moth and rust destroy, and where thieves break in and steal. But store up for yourselves treasures in heaven, where neither moth nor rust destroys, and where thieves do not break in or steal; for where your treasure is, there your heart will be also.” (Matt 6:19–21)

Be humble and patient with your Christian brethren.

So Jesus tells Peter all these things, and reminds him of the blessings of following Him. And He tells the disciples that the first shall be last—meaning those who are first in this life will be last in God’s eyes.

And yet… what if those rich men do come along and obey the gospel?

Now we see the purpose of this parable. I do not believe that Jesus is talking about whether there are degrees of reward in Heaven. No, this parable is (at least primarily) about the attitudes of the workers.

The workers who begin at first seem to be the Twelve. They’ve been with Jesus since the very beginning. They’re sacrificed quite a lot to serve Him, but they understand the heavenly reward. “But,” Peter asks, “what will there be for us?” You can hear the pride and indignation starting to swell up.

Hence Jesus presents this parable. Just as with the parable of the prodigal son, we see that the one who has been faithful longer resents the one who was initially unfaithful.

Yet a key difference is that in the parable of the prodigal son, the elder brother represents the Jews who were unaccepting of the Gentiles. In this parable, it seems that the out-of-line party represents the Apostles—and us as well, should we be guilty of the same attitudes.

“Now accept the one who is weak in faith, but not for the purpose of passing judgment on opinions.” (Rom 14:1)

Most likely, we will encounter and deal with plenty of Christians who are not fully wise.

God will welcome you at any time.

It is never too late to run to God.

This parable teaches us that God will not short-change you if you return to him late in your years or after living a horrible, sinful lifestyle.

“So He told them this parable, saying, “What man among you, if he has one hundred sheep and has lost one of them, does not leave the ninety-nine in the open pasture and go after the one which is lost until he finds it? And when he has found it, he lays it on his shoulders, rejoicing. And when he comes home, he calls together his friends and his neighbors, saying to them, ‘Rejoice with me, for I have found my sheep which was lost!’ I tell you that in the same way, there will be more joy in heaven over one sinner who repents than over ninety-nine righteous persons who need no repentance.” (Luke 15:3–7)

God finds great pleasure when his children return to Him.