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The Parable of the Two Sons is actually one of three parables in Matthew 21-22 that are addressed directly to the Jewish leaders who refused to believe in Jesus. We will examine the others – the Parable of the Wicked Vinedressers and the Parable of the Wedding Feast – over the next two weeks.
Introduction: As we have seen in our previous study of a number of Jesus’ parables, it is crucial to understand the context in which each individual parable is told as well as any explanation Jesus may give. Well, today’s parable is no different, and this is why – once again – I will discuss the parable under three headings: 1) the context of the parable, 2) the communication of the parable, and 3) the explanation of the parable.
I. The Context of the Parable (vss. 23-27)
We find the context of the parable in verses 23-27.
NKJ  Matthew 21:23 Now when He came into the temple, the chief priests and the elders of the people confronted Him as He was teaching, and said, “By what authority are You doing these things? And who gave You this authority?”
These leaders were trying to create a dilemma for Jesus. On the one hand, if He claimed that His authority came from God, then they would no doubt try to accuse Him of blasphemy, an accusation they had already considered before. For example:
NKJ  Matthew 9:1-7 So He got into a boat, crossed over, and came to His own city. 2 Then behold, they brought to Him a paralytic lying on a bed. When Jesus saw their faith, He said to the paralytic, “Son, be of good cheer; your sins are forgiven you.” 3 And at once some of the scribes said within themselves, “This Man blasphemes!” 4 But Jesus, knowing their thoughts, said, “Why do you think evil in your hearts? 5 For which is easier, to say, ‘Your sins are forgiven you,’ or to say, ‘Arise and walk’? 6 But that you may know that the Son of Man has power on earth to forgive sins” — then He said to the paralytic, “Arise, take up your bed, and go to your house.” 7 And he arose and departed to his house.
On the other hand, if Jesus said that He got his authority from men, He would not only deny that He was a true prophet, but He would also bring the charge that He really had no authority at all. For they were considered the religious authorities in Israel, and they had clearly not authorized His teaching or actions! Jesus taught as one having authority, but they resisted His authority and were trying to undermine it.

But, as we shall now see, Jesus turns the tables on them:
NKJ  Matthew 21:24-26 But Jesus answered and said to them, “I also will ask you one thing, which if you tell Me, I likewise will tell you by what authority I do these things: 25 The baptism of John — where was it from? From heaven or from men?’ And they reasoned among themselves, saying, “If we say, ‘From heaven,’ He will say to us, ‘Why then did you not believe [πιστεύω] him?’ 26 But if we say, ‘From men,’ we fear the multitude, for all count John as a prophet.”
Do you see how Jesus put them in the same kind of trap into which they tried to put Him? Remember that John had born witness to Jesus that He was the Messiah. So, if they believed John was a prophet from God, then they would have to believe in Jesus too. Since they didn’t believe John, however, they really wanted to say that he wasn’t a true prophet. But this put them in a different bind, because the people believed he was a true prophet. Thus, Jesus was challenging them to take a clear stand before the people on this matter, which they didn’t want to do, and this leads to their answer:
NKJ  Matthew 21:27 So they answered Jesus and said, “We do not know.” And He said to them, “Neither will I tell you by what authority I do these things.”
Jesus had said He would tell them by what authority He did the things that He did, but only if they first answered His question about John the Baptist. Since they didn’t want to give Him a straight answer to His question, He followed through on what He said and gave them no answer to their question.
Yet He doesn’t simply drop the matter. Instead, He tells a short parable and continues to question them in order to highlight the real issue, namely their unbelief.
II. The Communication of the Parable (vss. 28-31a)
We find Jesus’ communication of the parable beginning in verse 28 and extending through the first part of verse 31.
NKJ Matthew 21:28-31a  “But what do you think? A man had two sons, and he came to the first and said, ‘Son, go, work today in my vineyard.’ 29 He answered and said, ‘I will not,’ but afterward he regretted it [μεταμέλομαι] and went. 30 Then he came to the second and said likewise. And he answered and said, ‘I go, sir,’ but he did not go. 31 Which of the two did the will of his father?” They said to Him, “The first.”
The key word here is the word translated regretted in the NKJV. It is the Greek verb metamélomai, which can have one of two senses:
1) It can mean “to have regrets about [something], in the sense that one wishes it could be undone, be very sorry, regret ….”
2) It can mean “to change one’s mind about [something], without focus on regret, change one’s mind, have second thoughts” (BAGD3 #4851, BibleWorks).
Either way the basic idea is one of repentance, as we shall see more fully below. This is why I prefer the first translation, regret, which is followed by the NKJV and the NASB.
At any rate, the point Jesus is seeking to make is pretty hard to miss, even for these spiritually obtuse Jewish leaders. The first son initially refused to obey but then regretted his decision and obeyed, while the second son at first appeared to obey but never actually followed through. The issue is genuine obedience that follows a change of heart verses pretended obedience. Thus, without further ado, we may proceed to Jesus’ explanation.
III. The Explanation of the Parable (vss. 31b-32)
The explanation of the parable is found beginning in the second part of verse 31 and extending through verse 32.
NKJ Matthew 21:31b-32 Jesus said to them, “Assuredly, I say to you that tax collectors and harlots enter the kingdom of God before you. 32 For John came to you in the way of righteousness, and you did not believe [πιστεύω] him; but tax collectors and harlots believed [πιστεύω] him; and when you saw it, you did not afterward relent [μεταμέλομαι] and believe [πιστεύω] him.
There are at least three points that need to be considered here.
First, when Jesus tells the Jewish leaders that “the tax collectors and harlots enter the kingdom before you,” it is somewhat difficult to understand what this means. At first glance He seems to be saying that these Jewish leaders who haven’t believed will indeed enter the kingdom, but only after the the tax collectors and harlots who have believed. But this makes no sense at all in the context, and it also denies the teaching of Jesus and His Apostles elsewhere, which makes it clear that those who do not believe cannot enter the kingdom. This is one reason that D.A. Carson and a number of other noted scholars think that the Greek verb in the last part of verse 31 should not be translated as go before, but rather as go instead of.
But if Jesus should be taken as saying that these sinners will enter the kingdom before the Jewish leaders, I still do not think it necessary to understand His teaching here as saying that these Jewish leaders will indeed enter the kingdom themselves. In this case I think it best to follow Charles Spurgeon here and see Jesus as still holding out hope for these men if they will yet repent and believe. For example, in his sermon on this text, entitled “A Sermon to Open Neglecters and Nominal Followers of Religion,” Spurgeon says:
Oh! beware of saying as some of you do, “I go, sir,” while you go not. I sometimes see sick people who quite alarm and distress me. I say to them, “My dear friend, you are dying; have you a hope?” There is no answer. “Do you know your lost state?” “Yes, sir.” “Christ died for sinners.” “Yes, sir.” “Faith gives us of his grace.” “Yes, sir.” They say, “Yes, sir; yes, sir; yes, sir; yes, sir; yes, sir.” I sometimes wish before God they would contradict me, for if they would but have honesty enough to say, “I do not believe a word of it,” I should know how to deal with them. Stubborn oaks are leveled by the gale, but those who bend like the willow before every wind, what wind shall break them? O dear brethren, beware of being gospel hardened; or, what is the same thing, softened but for a season. Beware of being a promising hearer of the word, and nothing more!
I do not mean to close my discourse by speaking to you in this apparently harsh way, which, harsh as it seems, is full of love to your soul. I have a good word for you too. I trust that you, in this Agricultural Hall, will have a change wrought in you by the Holy Ghost, for although these many years you have made false professions before God; there is yet room in his gospel feast for you. Did you notice the text? “The publicans and sinners enter into the kingdom of heaven before you.” Then it is clear you may come after them, because it could not be said they entered before you, if you did not come after them. If the Lord shall break your heart, you will be willing to take the Lord Jesus for your all in all in just the same way as a drunkard must, though you have not been a drunkard. You will be willing to rest in the merit of Jesus just as a harlot must, though you have never been such. There is room for you, young people, yet, though you have broken your vows, and quenched your convictions. Ay, and you gray-headed people may be brought yet, though you have lived so long in the outward means, but have never given up your hearts to Jesus. Oh, come! This twenty-fourth day of March, may the Lord bring you in this very place, may the Lord lead you to say silently, “By the grace of God I will not be an open pretender any longer; I will give myself up to those dear hands that bled for me, and that dear heart that was pierced for me, and I will this day submit to Jesus’ way.”
Perhaps there are some here even this morning who fit Spurgeon’s description, who know they have been saying all the right things, but who also know that that they haven’t truly believed. If so, I implore you not to put off trusting in Christ any longer. It is time to get real with God!
Second, Jesus gives the reason they would be excluded from the kingdom, namely that they had not obeyed God’s message through John because they had refused to believe. In this they had been worse than the very tax collectors and harlots that they despised so much! Jesus later points out this very same issue:
NKJ  Matthew 23:1-5a Then Jesus spoke to the multitudes and to His disciples, 2 Saying: “The scribes and the Pharisees sit in Moses’ seat. 3 Therefore whatever they tell you to observe, that observe and do, but do not do according to their works; for they say, and do not do. 4 For they bind heavy burdens, hard to bear, and lay them on men’s shoulders; but they themselves will not move them with one of their fingers. 5 But all their works they do to be seen by men.”
Klyne Snodgrass has some helpful application of the parable at this point:
The primary feature of this text is clear. God requires productive and obedient living from his people. Claims and concerns for appearance are not enough. Churches often push for membership and professions of faith but allow (or even foster) a separation between believing and doing. How did people ever get the idea that obedience to the will of God is optional? Many parables, and especially this one, push for integrity of life before God. Talk and external appearance are cheap; what counts is actually doing the will of the father from the heart. Any separation of believing and doing is a distortion of the gospel message and is directly confronted by this parable. A person cannot believe apart from obedience. (Stories With Intent: A Comprehensive Guide to the Parables of Jesus, p. 275)
Third, Jesus also presses home the reason He had previously asked the Jewish leaders about their opinion of John. In the process, he reminds them that they have really already had two opportunities to relent and believe, although they had taken advantage of neither of them.
They had been like the second son in the parable, when they should have been like the first. Even though they had not responded rightly to John’s message in the beginning, they should have regretted it and believed afterward.
In this regard, Jesus is really just reinforcing the very teaching of John the Baptist himself – the teaching they had previously refused to accept. Recall John’s earlier encounter with the Jewish leaders:
NKJ Matthew 3:5-10 Then Jerusalem, all Judea, and all the region around the Jordan went out to him 6 and were baptized by him in the Jordan, confessing their sins. 7 But when he saw many of the Pharisees and Sadducees coming to his baptism, he said to them, “Brood of vipers! Who warned you to flee from the wrath to come? 8 Therefore bear fruits worthy of repentance, 9 and do not think to say to yourselves, ‘We have Abraham as our father.’ For I say to you that God is able to raise up children to Abraham from these stones. 10 And even now the ax is laid to the root of the trees. Therefore every tree which does not bear good fruit is cut down and thrown into the fire.”
Although earlier Matthew had referred to the Jewish leaders in terms of their religious positions – as Pharisees and Sadducees – in the passage before us this morning he identifies them instead by their religious titles or status – as the chief priests and elders of the people. But they were essentially the same groups and thus they are challenged for having committed the same sin, namely that they had professed to be true followers of God and thus workers in His vineyard (in the language of the parable), but they were all talk and no action! They said they would obey God, but when challenged both by John and by Jesus to do so, they refused!
And if this weren’t bad enough, they had not only the witness of John the Baptist and Jesus, but – as Jesus Himself points out – they had the witness of the radically changed lives of many tax collectors and harlots to demonstrate to them the reality and power of the kingdom message that they had been preaching. But they still did not repent and believe! Jesus said that they should have, and this parable challenges them to do so once again.
Conclusion: I would like to close by posing a few questions that we can each ask ourselves. For example, you might want to ask yourself, “Do I profess to believe in Jesus, although I know I have not really repented of my sin?” Or, perhaps you could ask yourself, “Do I claim to have repented of my sin, yet do not follow the Lord in obedience?” If you have not genuinely repented and obeyed the Gospel, then I pray by God’s grace that you too may regret this and trust in Him today.

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