The Parable of the Two Sons

The Parable of the Two Sons

The Parable of the Two Sons.

“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.’ He answered and said, ‘I will not,’ but afterward he regretted it and went. Then he came to the second son and said likewise. And the son answered and said, ‘I go, sir,’ but he did not go. Which of the two did the will of this father?” They said to him, ‘The first.’ Jesus said to them, ‘Assuredly, I say to you that tax collectors and harlots enter the kingdom of God before you. For John came to you in the way righteousness, and you did not believe him; but tax collectors and harlots believed him; and when you saw it, you did not afterward regret it and believe him.”  (Matthew 21:28-32).

CONTEXT. What a day! It started with Jesus’ Triumphal Entry into Jerusalem. A huge crowd welcomed Him like a conquering king, or more accurately, like a long-awaited messiah. It wasn’t merely a large crowd of people, it was “a very great multitude,” and they were spreading cloaks and tree branches on His path as he trotted into the city on a donkey. The people were chanting ‘Hosanna in the highest!‘ as all of Jerusalem was astounded at the arrival of the great Prophet, long expected from the prophecy of Moses (Deut. 18). Once Jesus slid off the donkey, He immediately stormed into the Temple and physically drove out those there who were turning the House of Prayer into a local marketplace. Soon afterwards, when everyone was holding their breath about what He would do next, all the blind and crippled in the area came to Jesus in the Temple, and He healed them all. The children got into the act next as they were caught up in all the excitement surrounding Jesus, crying out “Hosanna to the Son of David!” Despite the intense zeal and righteous indignation Jesus demonstrated, He somehow remained approachable as the blind and crippled and the children all felt comfortable in coming to Him.

The chief priests and scribes were indignant as they witnessed all these events, but they did nothing to stop the crowd in elevating Jesus to the role of Messiah and Prophet. The day drew to a close, and Jesus spent the night in nearby Bethany. He returned to Jerusalem in the morning and quickly cursed, of all things, a fig tree. The tree symbolized for Jesus the Temple leadership, and this was a sign that the Lord was condemning the Temple leaders for their lack of spiritual fruitfulness and their hypocrisy. The leaders once again approached Jesus at this time and asked Him where He got the authority to do all that He had done. As often happened, Jesus didn’t give them a straight answer. Instead, Jesus told them a little story about a father with two sons. The story is told directly to the chief priests and scribes, and was meant to pinpoint their failed spiritual leadership.

IRONIES. The disobedient son ended up doing the Father’s will, while the obedient son ended up being rebellious. The disobedient son changed his mind and repented of his attitude. The obedient son changed his mind and had no intention of repenting. The disobedient son realized he was not righteous, and went about doing the right thing. The obedient son thought he was righteous enough to do whatever he wanted. So, the disobedient son ended up being obedient, while the obedient son ended up being disobedient. Jesus said that the village outcasts, those the Temple considered to be great sinners, ended up a part of the truly religious in-crowd, and the Temple heroes ended up on the waiting list to the kingdom. Those who one would assume would be last in line jumped to the front, while those who were expected to be at the front were moved to the back. The repentant sinners entered the kingdom ahead of the unrepentant believers. Both sons changed their minds, the first for the good, the second not so much. The one did God’s will, the other didn’t. In both cases the sons did exactly the opposite they said they would do. The disobedient son ended up being celebrated for his humble repentance, and the obedient son ended up being rejected because of his deceit and hypocrisy.

GOD’S WILL. Jesus affirmed the son who ended up doing the father’s will, and He reproved the son who ended up refusing to do God’s will. This little parable seems to be a story that illustrates the teaching in Matthew 7:21: “Not everyone who calls out to me ‘Lord, Lord’ will enter the kingdom of heaven. Only those who actually do the will of my Father in heaven will enter.” The first son rebelled but then did His will. The second son said, ‘Yes, Lord, Yes, Lord!’ but then revealed an inner heart of rebellion and didn’t do what God asked. God approves of those who put faith into action in order to proves one’s status off the heart. How does one discern what God’s will is? Prayerfully study scripture, read God’s mind, and then live into that. Understand from the Bible what God expects of you, and do likewise, with God’s help. Use the good mind God gave you, seek righteous counsel, and decide from there. “Don’t be squeezed into the mold of this present age, imitating the ideals and opinions of the culture around you. But be inwardly transformed by the Holy Spirit through a total reformation of how you think. This will empower you to discern God’s will...” (Romans 12:2).


  1. If you were tempted to do one or the other, would you say no to a parent’s request and then change your mind, or would you say yes to a request and then rebel against it?
  2. Or instead, have you found yourself doing the same things as both sons in this parable?
  3. Is it predictable that the humble rebel obeyed, and the self-righteous rebel lied? Why?
  4. The father gave a second chance to the disobedient son, an opportunity to change his mind. Have you ever felt that you weren’t given a second chance after using poor judgment?
  5. The sinful outcasts jumped to the front of the line, while the religious folks had to wait to enter the kingdom. Does this mean that the religious rebels will still enter the kingdom eventually, even if it’s after the repentant sinners?
  6. To be ignorant of Scripture is to be ignorant of God’s will. Do you agree with that statement? Why or why not?