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” in His response to the disciples’ asking what reward they would have for giving up everything to follow Him (Matthew 19:27-30; Mark 10:28-31). He reiterated this truth in Matthew 20:16 at the end of the parable of the laborers in the vineyard. This statement is not, as many believe, a description of the reversal of earthly roles in heaven. There is no hierarchy in heaven wherein the poor and oppressed will rule over the rich and powerful when we get there. Nor will those believers who enjoy wealth and prestige on earth be somehow abased in heaven. Earthly rank will not automatically translate into heavenly rank.
When Jesus told the disciples they would be greatly rewarded in heaven for what they had given up on earth (Matthew 19:27-29), He was making a contrast with the rich young ruler, who was unwilling to give up much of anything for Christ’s sake (verses 16-22). The “last” in this world—the disciples in their poverty—would be “first” in the kingdom of heaven. Conversely, the “first” in this world—the self-sufficient rich—would be the last to find the kingdom.
In Matthew 20, Jesus’ parable concerns some hard-working individuals who complain that others, who did not work as long, were paid an amount equal to what they received. 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 no matter how long or how hard a believer works during his lifetime, the reward of eternal life will be the same given to all—an eternity of bliss in heaven in the presence of God the Father and the Lord Jesus Christ. 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 the apostle Paul. Of course, Scripture also teaches that there are different rewards in heaven for different services, but the ultimate reward of eternal life will be achieved by all equally.
Many commentators point out that Jesus’ statement in Matthew 20:16 can be applied to the Jewish/Gentile cultural milieu. 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.” Elsewhere, Jesus makes it clear why the “sinners” were being saved ahead of the pious: because of their repentance and faith, “the tax collectors and the prostitutes are entering the kingdom of God ahead of you” (Matthew 21:31-32).