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The Parable of the Two Sons – Matthew 21:28–32

During the early part of His ministry, Jesus spoke plainly to the people of Israel, offering the Kingdom of Heaven openly if they would receive Him as their Messiah. His teachings were direct, calling for repentance, faith, and readiness for the promised Kingdom. However, as Israel’s religious leaders hardened their hearts—accusing Him even of performing miracles by the power of Satan—Jesus began to teach in parables. These parables concealed truth from those who had rejected Him while revealing deep mysteries of the Kingdom to those who believed. This fulfilled the prophecy of Isaiah, where it was said that the people would hear but not understand, see but not perceive.

These parables, then, were not given as Church-age doctrine but as teachings about the mystery phase of the Kingdom—the form it would take between Israel’s rejection of the King and His eventual return. Though spoken to Israel before Christ’s death and resurrection, these parables will regain fresh significance during the Tribulation period, when the 144,000 sealed Jewish evangelists and the Two Witnesses will proclaim the coming Kingdom of Christ to both Jews and Gentiles. The parables will once again serve as powerful tools to reveal God’s plan for those ready to listen.

Words: 1403 / Time to read: 7 minutes


The Parable of the Two Sons

As Jesus neared the end of His earthly ministry, He engaged in sharp confrontations with the religious leaders of Israel. It was during this period—just days before His crucifixion—that He spoke the Parable of the Two Sons. With simple imagery and profound meaning, Jesus exposed the hypocrisy of those who claimed obedience to God but refused to truly follow His commands. The parable stands as a powerful call to genuine repentance and faithful response to God’s invitation.

In the story, a father asks his two sons to go and work in his vineyard. The first son responds with defiance, saying, “I will not.” Yet later, he changes his mind, repents, and goes. The second son, in contrast, offers a polite and respectful reply: “I will, sir.” But despite his words, he does not go. Jesus then asked His audience, “Which of the two did what his father wanted?” The answer was clear. It was the first son—the one who, though initially rebellious, ultimately obeyed.

Jesus’ audience, composed of religious leaders and others gathered in the temple courts, could not miss the point of His question. But what followed pierced them deeply. Jesus declared that tax collectors and prostitutes—the very people the religious elite despised—were entering the Kingdom of God ahead of them. These outcasts had heard John the Baptist’s call to repentance and responded, while the leaders had rejected it. The parable served as both an indictment and a warning: outward professions of obedience meant nothing without true repentance and action.


The Kingdom Message and Dispensational Significance

This parable speaks directly to Israel and its Kingdom program. The father represents God, the vineyard symbolizes Israel’s national calling and responsibilities, and the two sons illustrate two contrasting groups within the nation. The first son depicts those who once rebelled against God—such as tax collectors, prostitutes, and sinners—but who ultimately repented and embraced the message of the Kingdom. The second son embodies the religious leaders and others who professed loyalty to God but rejected His messengers and refused to obey His call.

The connection to John the Baptist is particularly significant. John came preaching repentance in preparation for the arrival of the Kingdom, and his ministry was a dividing line in Israel. Those who believed his message aligned themselves with God’s purposes, while those who rejected it—especially the religious elite—were exposed as disobedient.

Looking ahead, the parable also foreshadows what will happen during the future Tribulation period. Once again, Israel will be called to repentance and readiness for the return of the King. The 144,000 Jewish evangelists, along with the Two Witnesses, will proclaim the gospel of the Kingdom. As in Jesus’ day, many will reject that message, but a remnant—those who respond in faith like the first son—will turn to their Messiah and be welcomed into the Kingdom.


The Contrast Between Words and Deeds

The brilliance of this parable lies in its simplicity. The two sons represent two types of responses to God’s call. One openly defied his father but later repented and obeyed. The other said all the right things but failed to follow through. This contrast exposes the heart of the matter: what God desires is not empty words or outward displays of piety, but true repentance demonstrated through obedience.

The religious leaders of Israel were masters of external religion. They made public displays of their devotion, prided themselves on their knowledge of the Law, and enforced rigorous standards upon others. Yet when the call to repentance came—from John the Baptist, and then from Jesus—they hardened their hearts. Meanwhile, those deemed unworthy by society were the very ones who humbled themselves, repented, and entered the Kingdom.


Cultural and Historical Context

In the agrarian society of first-century Israel, sons were expected to work alongside their fathers, particularly in family vineyards or fields. To refuse a father’s command was not just disobedience—it was dishonor. But actions mattered more than words. A son who initially refused but ultimately obeyed was considered righteous in his deeds, whereas a son who agreed verbally but failed to act brought shame upon himself and his family.

Jesus’ choice of tax collectors and prostitutes as examples was no accident. These individuals represented the most despised in Jewish society—those seen as collaborators with oppressors or moral failures. That such people would enter the Kingdom ahead of the religious elite was unthinkable to His audience, and yet it was precisely the point. The Kingdom of God welcomes the repentant, no matter their past, while closing its doors to the proud and self-righteous who refuse to submit to God’s call.


The Broader Biblical Message

Though the parable speaks to Israel’s response to the Kingdom invitation, its truth resonates throughout Scripture. Paul later wrote of how Gentiles, who had not pursued righteousness, attained it by faith, while Israel, striving for righteousness through the Law, failed because they did not pursue it by faith (Romans 9:30-32). James reminded his readers that faith without works is dead—a truth vividly portrayed in the son who spoke well but failed to act (James 2:14-26). And Jesus Himself taught repeatedly that not everyone who says “Lord, Lord” will enter the Kingdom, but only those who do the will of the Father (Matthew 7:21).


Application and Reflection

This parable challenges every reader to examine the sincerity of their response to God. It is not enough to claim allegiance or offer respectful words. What matters is the heart’s repentance and the life’s obedience. God’s Kingdom is not inherited by those with the right pedigree or outward appearance, but by those who truly hear His call and respond.

For Israel, both in Jesus’ day and in the future Tribulation, the lesson is clear: true sons of the Kingdom are those who do the will of the Father, no matter their past. And for all who read this parable today, it is a sobering reminder that God sees beyond words and appearances—He looks at the heart.


Want to Go Deeper?

This post is adapted from my book, The Parables of Jesus: Covert Communication from the King (Grace and Knowledge Series, Book 7), where I explore each parable’s dispensational significance and prophetic meaning in greater depth.

Read the full book on Amazon →


All Scripture quoted from:
New International Version (NIV)
Holy Bible, New International Version®, NIV® Copyright ©1973, 1978, 1984, 2011 by Biblica, Inc.® Used by permission. All rights reserved worldwide.


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