After Jesus answers a group of Jewish leaders who challenged Jesus’s authority, the questioners remained silent. They refuse to answer the question of the source of John the Baptist’s authority. Jesus therefore presses them by questioning these chief priests with the brief parable of the two sons. Jesus asks them to respond to a “theological / philosophical” puzzle, which he will tie into John’s ministry and those that have repented of their sins because of the preaching of John.
A father asks two sons to go work in a field, one says that he will, but does not, the other says he will not, but feels guilty and does go to work. To refuse to do what a father asks is insulting to the father, and it in fact an act of rebellion. “The surprise is the father tolerates this” (Nolland, Matthew, 861). To work in the family vineyard is something a father would expect his sons to do.
The first son initially refuses, but “changes his mind.” This word (μεταμέλομαι) is not the normal word for repentance in the New Testament although it is similar. There is a sense of regret in the word (TDNT 4:626), maybe “to have second thoughts.” Jesus will use the word again in verse 32, the elders who rejected John have not “changed their minds” or regretted that decision and followed Jesus.
The second son responds positively, “I will go sir.” He is apparently a respectful and obedient child. But he never does go to the vineyard and work. If the first son was insulting, this son is overly polite and appears obedient, but he is not. The word “sir” is the word normally translated “lord” (κύριος) and was used generally the way we might use the word sir today. The translation is a good one, but it obscures some very critical parallels in Matthew’s gospel.
There are several people in Matthew who refer to Jesus (or a character in a parable that is by implication either Jesus or God) as “lord.” Simply to call on Jesus as “sir” is not enough, there must be a transformation of a person’s whole being to become a part of the Kingdom of heaven (Matt 7:21-22; 25:11-13; 25:44).
The second son is “all talk and no deeds.” The first son refused, not make any promise yet ends up doing the deeds that are expected of him.
Which son did want the father wanted (21:31-32)? The obvious answer is that the one who went and work for the father is the one that did the will of the father. The scribes that respond are condemning themselves with this answer, since clearly the son that does not go into the field represents them.
What is unusual (to me at least) is that neither son is the ideal. Which would you rather have, a child that refuses to obey but eventually does, or a son that says the right words, but never obeys in the end? The third possibility is a son that says that he will obey and then actually does what he says that he will do. Perhaps this is the case of the person who has entered the kingdom of heaven, they can promise to obey God and they can follow through on that promise with obedience.
What is the meaning of the Parable of the Two Sons? The point of the contrast is between the religious establishment and the under-class, Jesus does not have the third possibility in mind here. There would logically be a fourth possibility, the one who refuses to obey and never repents either. This might be the unsaved person that dies in their unbelief, but they are even further from the point of the parable!
There are two other possibilities, a son who does immediately what he is told, and a son who refuses and never changes his mind. It is possible there were followers of Jesus who immediately followed him and never turned back (Peter and the other disciples?) and others heard Jesus and immediately dismissed him as “not the Messiah” (Sadducees? Caiaphas?). But the parable is not concerned with the best or worst examples, it is the people in the middle who are called to respond to Jesus.
There is good news for both sons: the father did not punish them for their insult. This demonstrates the patience of God, like the father he wants both children to go to the vineyard and he is willing to wait for them to change their mind.
The bad news is the time of God’s patience is running out. The chief priests and elders must decide now who Jesus is. In a few days, they will do just that as they shout to Pilate for Barabbas to be released and Jesus crucified (Matt 27:20).