Question: "What did Jesus mean when He said the first will be last and the last will be first?"
Answer: Jesus made the statement “many who are first will be last, and many who are last will be first” (Matthew 19:30) in the context of His encounter with the rich young ruler (Matthew 19:16–30). After the young man turned away from Jesus, unable to give up his great wealth (verse 22), Jesus’ disciples asked the Lord what reward they would have in heaven, since they had given up everything to follow Him (verses 27–30). Jesus promised them “a hundred times as much,” plus eternal life (verse 29). Then He said, “But many who are first will be last, and many who are last will be first” (verse 30).
Jesus reiterated this truth in Matthew 20:16 at the end of the parable of the laborers in the vineyard, a story designed to illustrate the last being first and the first being last. What exactly did Jesus mean when He said, “Many who are first will be last, and many who are last will be first”? First, we should eliminate what He did not mean. Jesus was not teaching that the way to get to heaven is to live a life of poverty in this world. Scripture is clear that salvation is by grace through faith, not of works (Ephesians 2:8–9)—and independent of one’s financial status. Also, Jesus was not teaching an automatic reversal of roles in heaven. There is no heavenly law wherein the poor and oppressed must rule over the rich and powerful. The rich aren’t always last in heaven, and the poor aren’t always first. Nor will believers who enjoy wealth and prestige on earth be required to somehow be abased in heaven. Earthly rank will not automatically translate into an inverse heavenly rank.
When Jesus told the disciples they would be greatly rewarded in heaven for what they had given up on earth, He was contrasting their sacrifice with the rich young ruler’s lack thereof—the young man had been unwilling to give up much of anything for Christ’s sake (Matthew 19:16–22). God, who sees the heart, will reward accordingly. The disciples are an example of those who may be first, and they happened to be poor (but their poverty was not what makes them first in heaven). The rich young ruler is an example of those who may be last, and he happened to be rich (but his wealth was not what makes him last).
The Lord’s statement that the last would be first and the first last might also have held special meaning for Peter, who had just spoken of having “left all” (Matthew 19:27). Perhaps Jesus detected in Peter’s statement a bit of boasting—Peter was on the verge of becoming spiritually complacent—as the rich young ruler was, but for a different reason. Jesus’ response in verse 30 may have been an indirect warning to Peter to always find his sufficiency in Christ, not in his own sacrifice. After all, without love, even the greatest sacrifice is worthless (1 Corinthians 13:3).
In the chapter following Jesus’ statement that the first will be last and the last will be first, Jesus tells a parable (Matthew 20). The story concerns some laborers who complain that others, who did not work as long as they, were paid an equal amount. In other words, they saw their own labor as worthy of compensation but considered their companions’ labor to be inferior and less worthy of reward. Jesus ends the parable with the statement, “The last will be first, and the first last” (Matthew 20:16). The most direct interpretation, based on the content of the parable, is that all believers, no matter how long or how hard they work during this lifetime, will receive the same basic reward: eternal life. The thief on the cross (Luke 23:39–43), whose life of service was limited to a moment of repentance and confession of faith in Christ, received the same reward of eternal life as did Timothy, who served God for years. Of course, Scripture also teaches that there are different rewards in heaven for different services, but the ultimate reward of eternal life will be given to all equally, on the basis of God’s grace in Christ Jesus.
There are several ways in which “the first will be last and the last first” holds true. There are some who were first to follow Christ in time yet are not the first in the kingdom. Judas Iscariot was one of the first disciples and was honored to be the treasurer of the group, yet his greed led to his undoing; Paul was the last of the apostles (1 Corinthians 15:8–9) yet the one who worked the hardest (2 Corinthians 11:23). There are some who were first in privilege yet are not first in the kingdom. Based on the terms of the New Covenant, the Gentiles had equal access to the kingdom of heaven, although they had not served God under the Old Covenant. The Jews, who had labored long under the Old Covenant, were jealous of the grace extended to the Gentile “newcomers” (see Romans 11:11). There are some who are first in prestige and rank yet might never enter the kingdom. Jesus told the Pharisees that the sinners they despised were being saved ahead of them: “Truly I tell you, the tax collectors and the prostitutes are entering the kingdom of God ahead of you” (Matthew 21:31–32).
What Jesus is teaching in Matthew 19:30 is this: there will be many surprises in heaven. Heaven’s value system is far different from earth’s value system. Those who are esteemed and respected in this world (like the rich young ruler) may be frowned upon by God. The opposite is also true: those who are despised and rejected in this world (like the disciples) may, in fact, be rewarded by God. Don’t get caught up in the world’s way of ranking things; it’s too prone to error. Those who are first in the opinion of others (or first in their own opinion!) may be surprised to learn, on Judgment Day, they are last in God’s opinion.