Commentary - Matthew 21:28-32

Bird's-eye view

In this parable, Jesus puts His finger directly on the central issue He has with the religious leadership in Jerusalem. It is not a matter of doctrinal minutiae, but rather a fundamental issue of the heart, manifesting as rank hypocrisy. Coming right after they challenged His authority, this story is a direct counter-punch. Jesus doesn't just answer their challenge; He turns the tables and challenges the very foundation of their religious standing.

The parable presents a simple scenario with two sons, but it serves as a devastating indictment of the chief priests and elders. They are the son who talks the talk, who has all the right words, but whose actions betray a rebellious heart. In stark contrast, the tax collectors and prostitutes, the deplorables of that society, are the son who initially rebels but then repents and does the father's will. The central theme is that true obedience is not found in pious professions but in repentant action. God is not after lip service; He is after the heart, and a repentant heart will always result in a changed life.

Outline

Clause-by-Clause Commentary

v. 28 “But what do you think? A man had two sons, and he came to the first and said, ‘Son, go work today in the vineyard.’

Jesus begins with a question, "But what do you think?" He is not asking for their idle opinion. He is cornering them, forcing them to render a judgment that will, in the end, condemn them out of their own mouths. This is a masterful rhetorical move. The setup is simple and relatable: a father and two sons. The command is straightforward: "Son, go work today in the vineyard." The vineyard, in Scripture, is a common metaphor for Israel, God's covenant people. The father is God, and the sons represent two different groups within Israel. The command is a call to fruitful obedience, to do the work God has assigned.

v. 29 And he answered and said, ‘I will not’; but afterward he regretted it and went.

The first son's response is blunt, disrespectful, and rebellious. "I will not." This is open defiance. There is no attempt to soften the blow, no excuse offered. It is a raw and honest "no." But the story doesn't end there. "Afterward he regretted it and went." The key word here is "regretted." It signifies a change of mind and heart that leads to a change in action. This is the very picture of repentance. He didn't just feel bad about his insolence; his regret propelled him into the vineyard. His initial words were wicked, but his final action was obedience.

v. 30 And the man came to the second and said the same thing; and he answered and said, ‘I will, sir’; but he did not go.

The second son is the polar opposite of the first, at least in his words. His response is a model of respect: "I will, sir." He uses a term of respect and gives the right answer. He makes the profession of obedience. If you were to judge by words alone, this is the good son. But his actions, or lack thereof, tell the real story. "He did not go." His profession was hollow. It was a lie. He honored his father with his lips, but his heart was far from him. This is the very definition of hypocrisy: saying one thing and doing another.

v. 31 “Which of the two did the will of his father?” They said, “The first.” Jesus said to them, “Truly I say to you that the tax collectors and prostitutes will get into the kingdom of God before you.

Jesus now springs the trap. He asks the chief priests and elders to judge the situation. The answer is obvious, and they give it: "The first." They have just affirmed that action, not words, constitutes true obedience. They have condemned the hypocritical son and vindicated the repentant one. And with their own verdict hanging in the air, Jesus brings the hammer down. "Truly I say to you..." This is a solemn declaration. What follows is a bombshell. The tax collectors and prostitutes, the very dregs of society, the ones who openly said "I will not" to God's law, are entering the kingdom ahead of these religious leaders. Why? Because like the first son, they repented. Their lives were a mess, but they changed their minds and their actions.

v. 32 For John came to you in the way of righteousness and you did not believe him; but the tax collectors and prostitutes did believe him; and you, seeing this, did not even regret afterward so as to believe him.

Jesus now explains the application with unmistakable clarity. The ministry of John the Baptist was the great dividing line. He came "in the way of righteousness," preaching a message of repentance that was in perfect accord with God's law. The religious leaders, the second son, gave lip service to that law but rejected John's call. They "did not believe him." But the outcasts, the first son, the tax collectors and prostitutes, heard John and "did believe him." Their belief was not mere intellectual assent; it was the kind of belief that led to repentance and baptism. And here is the final, damning charge. The leaders saw this. They saw the transformed lives. They saw the fruit of repentance in the most unlikely people. And even then, "you... did not even regret afterward so as to believe him." Their hearts were so hard that even the clear evidence of God's power at work in the lives of sinners could not provoke them to repentance. They were locked into their hypocrisy, content with their verbal "I will, sir," while their feet remained planted firmly outside the vineyard.

Application

This parable is a sharp stick in the eye to any form of comfortable, respectable, nominal Christianity. It teaches us that God is utterly unimpressed with our religious vocabulary if it is not matched by a repentant heart and obedient hands. It is possible to have a perfect church attendance record, to say "amen" in all the right places, to know the catechism backward and forward, and yet to be the second son who does not go into the vineyard.

The good news of this parable is that the door to the vineyard is always open to the one who repents. It doesn't matter how egregious your past rebellion has been. The first son's "I will not" was a flagrant sin, but it was not the unpardonable one. The unpardonable sin is the settled hypocrisy of the second son, who sees the grace of God at work and refuses to "regret afterward so as to believe."

Therefore, we must constantly examine ourselves. Are our actions lining up with our profession? When we are confronted with our sin, is our first instinct to say "I will not," or is it to say "I will, sir" while continuing in our disobedience? The gospel call is a call to be like the first son in his repentance. We have all, at times, said no to the Father. The question is, what do we do afterward? Do we regret, and go? Or do we harden our hearts, content with the mere profession of obedience? The kingdom of God is filling up with repentant rebels, not with respectable hypocrites.