As you read Matthew through chapter by chapter, you notice certain recurring themes. At the very end of chapter 19 Jesus says, “But many who are first will be last and the last first.” Then, just a few verses later, Jesus says, “So the last will be first and the first last” 20:16. Taken on the surface, these statements are essentially repetitions of one another – just reversed in their order. But when you look at this in context, Jesus is applying this reversal motif to very different situations.
The first statement, Matthew 19:30, comes on the heels of Jesus’ interaction with the rich young ruler. Jesus’ words to that man cause Peter to wonder, “Is following You really worth it? What’s in it for me?” Jesus wants Peter to know (and all of us) that no matter what you sacrifice in this world, God will superabundantly reward you – both in this world and especially in the world to come. Thus, when Jesus says “many who are first will be last and the last first” he making a point about how the Gospel will result in a massive reversal of fortunes: devoted followers like Peter will gain immensely (the last will be first), while the rich who reject Jesus’ call will lose everything (the first will be last).
The second statement comes in the context of Jesus’ parable of the laborers in the vineyard. All the groups work for a different amount of time but all are paid the same – and most are paid with surprising generosity. When it comes time to pay those who worked the longest, they are offended because they do not receive more than those who worked the shortest. It seems to me that Jesus is telling this parable to combat the pride and entitlement mentality of Christian disciples who serve the ‘longest’. Longest could mean having a Jewish family heritage rather than a Gentile heritage, or possibly following Christ from a young age, rather than turning to Christ at an older age. My study Bible suggests the following: “It is probably correct … to see here a warning that Jesus’ early followers (such as the Twelve) should not despise those who would come later.” If they do despise others and approach heaven with this entitlement mentality, even these ‘first’ ones will be disappointed – they will be ‘last’. But for those who enter into the joy of heaven depending entirely on God’s generous grace, even at the eleventh hour, these will be first in joy and gratitude.
The Gospel is the story of the first (the Son of God) who chose to become last (on the cross). But by his resurrection from the dead, the last became first (at his resurrection), a foretaste of the good world to come. The Gospel turns our world’s thinking and expectations on its heads!