The Parable of the Two Sons
Matthew 21:28–32
The Parable of the Two Sons
Setting the Scene
The parable is brief, almost deceptively simple. A father has two sons. He asks the first to work in the vineyard that day. The son answers, “I will not,” then later changes his mind and goes. The father makes the same request of the second son. This one answers, “I will, sir,” and never goes. Jesus then asks the obvious question: which of the two did the father’s will?
The listeners answer correctly: the first. Jesus immediately turns the story against them. Tax collectors and prostitutes, He says, are entering the kingdom of God ahead of the religious leaders, because John came “in the way of righteousness” and they believed him, while the leaders did not—and even after seeing the fruit of that belief, they still refused to repent.
The vineyard, the father’s summons, the two kinds of response: these are not casual details. They belong to a moment of public collision in Jerusalem, only days before the cross.
Context
The parable does not stand alone. It is the first of three judgment parables Jesus tells in the Temple after His authority has been challenged (Matthew 21:23–27). The day before, He had entered Jerusalem as king and cleansed the Temple courts. The chief priests and elders now demand to know by what authority He acts. Jesus answers with a counter-question about John the Baptist. When they refuse to answer, He refuses to answer them—and then tells this story.
In Israel’s Scriptures, the vineyard is a standing image for the people of God (Isaiah 5:1–7). The father who summons sons to work is God. The “way of righteousness” that John preached is the summons of the kingdom: repent, for the kingdom of heaven is at hand. The first son represents those who had lived in open disobedience—tax collectors, prostitutes, the religiously disqualified—yet who, at John’s preaching, changed their minds and entered. The second son represents those who had said “yes” to God with their lips, their liturgy, and their public reputation, and then withheld the obedience that the summons required.
The parable is therefore not a general homily on sincerity. It is a verdict spoken to Israel’s shepherds in the house of God, in the last week of Jesus’ public ministry. It belongs with the two parables that follow it: the wicked tenants and the wedding banquet. Together they announce that those who claim the vineyard while refusing the owner’s will will lose what they think they possess.
Observations
Several features of the text repay close attention.
First, both sons are addressed as sons. Jesus does not divide the world into children of God and outsiders. The religious leaders and the public sinners stand inside the same household. The question is not pedigree but response.
Second, the decisive verb is not “said” but “went.” The first son’s initial refusal is honest; his later change of mind produces action. The second son’s courtesy—“I will, sir”—is empty. Matthew’s Gospel has already prepared this contrast: “Not everyone who says to me, ‘Lord, Lord,’ will enter the kingdom of heaven, but only the one who does the will of my Father” (7:21). Words of allegiance, even orthodox words, are not the same as the Father’s will done.
Third, the change of mind is named with a verb that carries the sense of regret that leads to a different course (metamelomai). It is not yet the full New Testament vocabulary of repentance, but it is the movement John demanded: a turning that becomes visible. The leaders saw that turning in others and still would not make it themselves. Their failure is therefore not ignorance. It is refusal after evidence.
Fourth, Jesus’ application is sharper than a mere ranking of sinners. “Ahead of you” does not mean the leaders will enter later if they wait long enough. In the logic of the chapter, those who will not believe John’s witness will not recognize the One to whom John pointed. The door they think they guard is already opening for people they despise.
Fifth, the parable is interactive. Jesus forces the leaders to pronounce the verdict before He names them as the second son. They condemn themselves out of their own mouths. That is how prophetic parables often work: the hearer supplies the judgment that then falls on the hearer.
Questions
The parable leaves several questions that theology cannot hurry past.
If both sons belong to the father’s house, what does sonship actually require? Is covenant identity a status that can be claimed while the day’s work is left undone?
What is the relationship between John’s “way of righteousness” and Jesus’ own authority? Jesus treats belief in John as the test of readiness for the kingdom He Himself brings. Can one honor Jesus while dismissing the repentance John preached?
How should the church hear the second son? The danger is not only first-century priestly hypocrisy. It is any community that recites “I will, Lord” in worship, creed, and moral language, and then does not enter the vineyard of mercy, justice, and costly obedience.
Does the first son’s story offer cheap comfort to those who begin in rebellion? The parable does not praise the initial “I will not.” It praises the later going. Grace is real; so is the demand that grace produce a changed life.
Finally, what becomes of a leadership that sees repentance happening in others and still will not repent? The next two parables answer that question with increasing severity. The vineyard will be given to others who will produce its fruit.
Conclusion
The Parable of the Two Sons is a story about the difference between profession and performance, spoken at the point where Israel’s official religion and God’s present summons collided. The Father still calls sons to work in His vineyard today. Some begin with a hard no and later discover they cannot stay away. Others begin with a polite yes and never arrive.
Jesus’ point is not that sinners are automatically preferred to the devout. It is that the kingdom belongs to those who actually do the Father’s will after they have been summoned—those who, like the first son, change their minds and go. The religious leaders of Matthew 21 had the language of obedience and the appearance of loyalty. What they lacked was the repentance John announced and the faith that would recognize the Son standing before them.
The parable therefore remains a searching word. It asks not first what we have said about God, but whether we have gone into the vineyard. The Father is still speaking. The day is still “today.” The question Jesus put to the Temple authorities is the question the text puts to every hearer: which of the two did the will of the Father?
Related Verses
Saying “yes” without going
Matthew 7:21–27; 23:2–3; James 1:22–25; 2:14–17; Isaiah 29:13; Ezekiel 33:31–32
Doing the Father’s will
Matthew 12:50; John 4:34; 6:38; 1 John 2:17
