*Scripture verses covered in this section's commentary are noted in italics

Matthew 21:28-32 meaning

Verses covered in this passage:

  • Matthew 21:28
  • Matthew 21:29
  • Matthew 21:30
  • Matthew 21:31
  • Matthew 21:32

Jesus tells a parable about two disrespectful sons of a vineyard owner. Both are told to go work in the vineyard by their father. The first said he wouldn’t go, but later repented and did. The second said he would go, but never went. Jesus then asked the priests and elders which of the two sons actually obeyed. They gave the correct answer. Jesus then explained its meaning to everyone in the temple.

The parable in Matthew 21:28-32 is unparalleled in the gospel accounts.

The chief priests and elders had just confronted Jesus in the temple about His authority (Matthew 21:23). They were trying to trap Him. Jesus cleverly avoided their trap and promised to answer their question if they would first tell Him if they thought John the Baptist was a divine prophet or not (Matthew 21:24-25). They declined to answer His question out of fear of being exposed as hypocrites or displeasing the crowd (Matthew 21:25-27). Jesus then declined to answer their question (Matthew 21:27) before telling them two parables.

The first of these two parables is often called “the parable of the two sons” (Matthew 21:28-30). The second is often called the “the parable of the vineyard” or “the parable of the vine-growers.” The second parable is also sometimes called the “parable of the landowner” (Matthew 21:33-40; Mark 12:1-11; Luke 20:9-16). Both parables were about the kingdom of God. They were addressed to and mainly concerned the chief priest, elders, and the Pharisees (Matthew 21:45). It was these groups who had opposed Jesus, and whom He had just thwarted.

The first parable was short. Jesus sandwiched it between questions directed toward the Sadducees. He introduced the parable by asking them: But what do you think? (v 28). His question put the priests on notice that He was interested in their opinion about the parable He was about to tell them. If they would not answer His question about John the Baptist’s authority, then perhaps they might be willing to say what they thought about a made-up story.

The parable was about a man and his two sons. The man was the owner of a vineyard. In the agricultural civilization of Israel, vineyards were commonly family businesses. And in Jesus’s parable, this family was in the vineyard-business. The two sons worked for their father, but they also worked for themselves, because they were the inheritors of the vineyard.

The man came to his first son and said to him, Son, go work today in the vineyard (v 28). But his first son replied, I will not. This was disrespectful and disobedient. The son’s in-your-face rebelliousness broke the harmony of fellowship between him and his father. But afterward, once the son considered what he had done he regretted saying what he said and the tension that he caused. And he then repented of his rebellion and went and did go work that day in the vineyard as his father (v 29) had asked him to do.

The man came to the second and said the same thing (v 30). But the second son gave the opposite response of his brother. The second son told his father “I will go, sir, (v 30) when he was asked to go work in the vineyard. His answer was not only the correct and obedient answer it was also said with an apparent tone of respect. However, he disguised his disrespect. After saying this, he did not go work the vineyard as his father asked (v 30).

Neither son was perfect. Both showed disrespect. But their offense was shown in different ways. The first son was disrespectful and noncompliant in his initial response to his father, but he then ended up obeying his father’s request. The second son was deceitful when he feigned respect and signaled an intent to obey his father. He disguised his disrespect with the right words, which made his disobedience the more hurtful. After lying to his father, the second son did not go (v 30) and do what he promised, while the first son repented of his disobedience and did what his father asked him to do.

Jesus concluded this short parable by asking the chief priests and elders: Which of the two [sons] did the will of his father? (v 31).

They responded simply with ‘the first.’ Their answer was correct. The first son was the one who did his father’s will, despite the initial disrespect. He ultimately obeyed his father when he went to go work today in the vineyard.

Jesus built upon the obvious correctness of the priests’ and elders’ answer. And calling upon His own authority, told them a shocking truth. Truly I say to you that the tax collectors and prostitutes will get into the kingdom of God before you (v 31).

The tax collectors and prostitutes (v 31) were represented by the first son in the parable. Tax collectors worked for Rome and benefited from Rome’s oppression of the Jews. Jesus’s disciple Matthew, the author of this Gospel account, was a tax collector (Matthew 9:9). Tax collectors were generally viewed as sinful betrayers of God and His people. Prostitutes were also despised by the priests and elders for their lifestyle that sought to make a living through their sin with others. Both tax collectors and prostitutes transgressed God’s commandment to love your neighbor as you love yourself (Leviticus 19:18). And yet it was the tax collectors, prostitutes, and other sinners who repented when they heard the gospel message from Jesus and John. This of course included the author, Matthew. It is not surprising that Matthew chose to include this parable in his gospel account, since he was a tax collector who repented and followed God.

Meanwhile the religious leaders were represented by the second son who feigned respect and promised obedience but did not go and do the will of God. The priests and elders were like what the Lord said of Israel to Isaiah. They claimed to respect and follow God with their words, but did not follow Him in their deeds:

“Because this people draw near with their words
And honor Me with their lip service,
But they remove their hearts far from Me,
And their reverence for Me consists of tradition learned by rote.”
(Isaiah 29:13)

Jesus further clarified this point when He stated the facts about John the Baptist and his ministry. This connected with the prior episode where Jesus asked the priests and elders about John’s authority. How each son responded to John’s message showed their true heart. John’s message was “Repent, for the kingdom of heaven is at hand” (Matthew 3:2). Jesus then said to the Jewish leaders, For John the Baptist came to you in the way of righteousness and you did not believe him; but the tax collectors and prostitutes did believe him (v 32). The belief of the tax collectors and prostitutes (v 32) was demonstrated by their repentance and baptism. In saying this, Jesus explained His statement how the tax collectors and prostitutes will enter the kingdom prior to the Jewish leaders.

Because these sinners repented like the first son in the parable, they went to work in God’s kingdom, (represented by the vineyard) before the unrepentant and unbelieving Sadducees and Pharisees. That’s how the tax collectors and prostitutes will enter the kingdom of God first. The “religious” sinners were like the second son, who only claimed to follow God with their words but not their heart or actions. Jesus makes clear that they will not get to enter God’s kingdom until they repent.

And youJesus said, addressing the priests and elders—after seeing the sinners repent did not even feel remorse afterward so as to believe John the Baptist (v 32). Jesus pointed out the remarkable but sad fact to these unrepentant religious leaders that even now they were refusing to repent. They remain outside the kingdom instead of repenting and entering it as other sinners were doing.

These religious leaders were behaving like the fruit tree that Jesus cursed on His way into the city, and unless they repented, they too would wither, never to produce fruit again (Matthew 21:19). Tragically, their blindness led to additional blindness, as was also the case in the continuing verse from Isaiah.

“Therefore behold, I will once again deal marvelously with this people, wondrously marvelous;
And the wisdom of their wise men will perish,
And the discernment of their discerning men will be concealed.”
(Isaiah 29:14)

In adding this parable, Jesus indirectly, but clearly, answered both His own question to the priests and elders about the source of John’s authority (Matthew 21:25), as well as their question to Him about His authority (Matthew 21:23). In this parable, John’s “baptism” and Jesus’s authority “to do these things” were both from God.

Biblical Text

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.’ 29 And he answered, ‘I will not’; but afterward he regretted it and went. 30 The man came to the second and said the same thing; and he answered, ‘I will, sir’; but he did not go. 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. 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 feel remorse afterward so as to believe him.

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