Long (Matthew, Westminster Bible Companion) writes concerning the rich man story, which also applies to our text: “… we must realize that, when the young man encounters Jesus, two very different worlds collide: this world, with all its prevailing customs and values, and the radical new way of life called for in the kingdom of heaven.” [p. 220]
This radical life comes at a price. Peter understands that and so he asks, “what about us who have already given up everything,” Jesus points to the life within the kingdom and then concludes that the called-for reversal will also be evident in the order of blessing on entering the kingdom: “But many who are first will be last, and the last will be first.” (Mt 19:30)
While the context for the kingdom in Mt 19 is seen “when the Son of Man is seated on his throne of glory,” But it is not just in the end of days. Matthew also grounds the radical reversal of all cultural understandings in the here-and-now. In a time (then and now) when wealth is seen as a measure of blessing, most commentators note the importance of Mt 19:16-30 – the encounter with the Rich Man. I short, when Jesus tells him “If you wish to be perfect, go, sell what you have and give to (the) poor, and you will have treasure in heaven. Then come, follow me.” The rich man goes away sad.
As that encounter ends, Mt 20:1 begins with the word “for” (gar) which implies a connection to what goes on before. It denotes a reason. Perhaps we could even say that it introduces an answer to the question: Why will many who are first be last and the last first (see 19:30; 20:16)? It may be as simple as the idea of being “paid,” not by what one does – either by doing good deeds or keeping the commandments or working in the vineyard – but by the graciousness of God/landowner.
Both the story of the young man and the parable of the employer picture the triumph of grace. The young man is a fine specimen who “has it all”: youth, money, morality, a sense that there is still something more, an interest in eternal things. Matthew resists the temptation to make the disciples (and his own church) look the better by painting the man in dark colors. He was a good, sincere, wealthy young man, and every church would be glad to “get” him. What did he lack? He anticipated being given one more commandment, one final achievement, and then his quest would be fulfilled. Not just the young man, but also the reader is surprised when he is told that he lacks all, that his salvation is impossible. At one level, the story communicates that salvation is not any kind of achievement, that on human terms entering the kingdom is not merely hard, but impossible. It is only when this “no” to all human claims is heard that the “yes” of God can be heard: But for God all things are possible. Binding this pronouncement to the call to discipleship keeps it from being cheap grace.
The rich young man is a picture of the rejection of grace by one who prefers to justify himself. The parable of the landowner and the laborers is a picture of the resentment of grace toward others by those who have worked long and hard themselves.