Meaning of the Parable of the Two Sons in Matthew 21

The parable of the two sons in Matthew 21:28-32 is about a father who instructs his sons to work in the family vineyard.

The first son refuses to work but later has a change of heart and obeys.

The second son says he’ll work, but never does.

Jesus shows how those often labeled as “lost” or “sinners” (like harlots and tax collectors) are like the first son. Despite their outwardly visible struggles with sin, they receive salvation because they believe in Jesus and repent.

The religious leaders are like the second son. They claim to serve God but neglect His people, oppose His messengers, and see no need to repent, thinking they’re fine as they are. So, despite appearing religious, they miss the one way to salvation.

This isn’t the most discussed parable. In fact, due to its name, it’s often confused with the parable of the prodigal son. And while they do have some overlapping themes, this parable has its own distinct message.

So let’s read through it and see what there is to learn:

• Reading Jesus’ words
• The context of the parable
• What the parable means
• Why it matters for Christians today
• Where we go from here

We’ll start by walking through the passage in the New Testament.

The parable passage

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Here’s how the parable goes in Matthew 21:

“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 and said likewise. And he answered and said, ‘I go, sir,’ but he did not go. Which of the two did the will of his 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 of righteousness, and you did not believe him; but tax collectors and harlots believed him; and when you saw it, you did not afterward relent and believe him” (verses 28-32, NKJV).

This parable has the added bonus of Jesus explaining the primary message. But even so, there’s a bit more to discuss. And it can make a difference in how we view obedience to God.

So let’s look at what was going on at the time that prompted the telling of this short story.

Historical context of the parable

We can find some clues to this parable by looking at all passages in Matthew 21. We know Jesus was in Jerusalem because He made His triumphal entry right before this (21:1-11).

That means He was on the turf of the Jewish religious leaders—those who claimed to be God’s representatives to the Jews in Israel. They were called chief priests and elders in verse 23, and this group would have included sects like the Pharisees and Sadducees.

Jesus was speaking directly to them in this parable, but there were likely crowds of commoners there, too. They followed Jesus everywhere (21:8-14).

And the patterns in the surrounding verses can also help us see why Jesus told this parable.
Here’s a breakdown of Matthew 21:

1. Jesus enters Jerusalem, riding on a donkey. The common people flock to Him in the hopes that He is the promised Messiah (verses 1-11).

 

2. While in Jerusalem, Jesus stands up to those doing business and ripping off poor people in the temple. The common people again praise Jesus as Messiah and come to Him for healing. But the religious leaders grow angry at the disruption to their system and want Jesus to silence those who praise Him (verses 12-17).

 

3. Jesus passes a fig tree that’s full of lush leaves but not bearing fruit, so He causes it to wilt. It sparks a teaching moment with His disciples about the power of faith (verses 18-22).

 

4. Religious leaders question Jesus’ authority to do miracles. Jesus responds by asking them about John the Baptist’s authority to baptize. The leaders don’t believe John was God’s prophet. But they know the onlookers do, so they refuse to answer. In turn, Jesus doesn’t answer their questions about His authority (verses 23-27).

 

5. Instead, Jesus tells the parable of two sons—one who obeys the father’s will and one who doesn’t (verses 28-32)

 

6. Jesus tells a parable about wicked vineyard workers who end up killing the owner’s representatives, and finally his son. And as a result, the vineyard owner replaces them with new workers. Jesus compares this to how He’ll replace the Jewish religious leaders with those who will faithfully serve as God’s representatives (verses 33-43).

Do you see the pattern?

These passages parallel two generalized classes of people. The commoners, who look to Jesus as the Messiah, represent one class. And the religious leaders represent the second. Most of them appear righteous but don’t recognize God’s presence or authority.

As per tradition, the common people looked to the religious leaders as God’s representatives. They knew a lot about Scripture and they followed strict religious customs. But the leaders separated themselves from anyone who didn’t seem good enough. There was no love or humility. They prioritized their pride and religious customs over shepherding God’s people (i.e., they were selfish).

The chief priests and elders were like the fig tree—full of show but making no positive difference. Bearing no real fruit.

They despised and resented Jesus because He had great influence over the people—as John the Baptist had. So instead of joining forces with Him, they protected their own power. They destroyed God’s true representatives, like the wicked vineyard workers did.

Meanwhile, most of the common people and “obvious sinners” recognized Jesus as their Messiah. The religious leaders saw no hope for them, but Jesus embraced them.

And that sheds light on the full significance of the parable of the two sons.

The Main Point of the Parable of Two Sons

This parable is about the two actual classes or categories that will exist until Jesus returns—those who sincerely desire God and those who don’t. Here’s what each part of the parable represents:

• The father represents God.

• The father’s vineyard represents the earth.

• The work is the Christian duty to spread the good news about the Messiah to others.

• The first son represents the harlots (prostitutes) and tax collectors (publicans). But this is really a “catch-all phrase designating all the social and religious outcasts.” It’s those who are painfully aware of their guilt and repent.

• The second son represents the self-righteous religious leaders. But this son can represent anyone who claims to serve God but doesn’t make any effort to do His will or acknowledge the need to repent.

• Themes include pride, obedience, and hypocrisy—to name a few.

• Characteristics of God include unconditional love, forgiveness, a devotion to seeking out those who need help and healing, and a desire for genuine obedience.

Neither son in the story is perfect—as no human being is perfect (Romans 3:23). Both sons in the parable disobey their father at some point. But there’s a difference. The first son repents and fulfills his duty, showing himself a true son to the master of the vineyard. But the other son is content with his good intentions. It’s as if he thought his words were enough.

Oof. Let that sit for a moment. Despite his right answer, it didn’t impact his actions.

The prostitutes and tax collectors were better off for acknowledging their imperfections and being willing to change. Their humility allowed the Holy Spirit to open their eyes to God’s power at work in John the Baptist and Jesus.

Even the smallest sin leads to death (James 2:10, Romans 6:23). But the leaders saw no need for forgiveness because others appeared worse (Luke 18:9-14). In their pride, they shut out the influence of the Holy Spirit. And it put them in much greater spiritual danger than those they looked down on.

And worse, they still claimed to represent God, even though they neglected the highest of all their responsibilities. They distanced themselves from those who seemed less worthy instead of serving them. And they opposed Jesus and John the Baptist—who obeyed the call to work in God’s vineyard and tend His people.

This exclusivist mindset is another reason they rejected Jesus. They couldn’t imagine supporting anyone who would welcome a tax collector or harlot.

That’s why Jesus often called religious leaders “hypocrites” (Matthew 23). They accepted the role of shepherd to God’s people, but never followed through.

Yet God didn’t give up on these hard-hearted leaders:

“Tactfully but purposefully, Jesus led them, as He so often did, to condemn themselves (see v. 41), so that they might view their conduct in its true light.”

Jesus reveals three things about God’s character through this parable:

1. A desire to save everyone: Jesus tries to open the eyes of stubborn religious leaders to their need for a Savior.
2. Accountability: God expects His followers to live faithful lives according to His instructions.
3. Forgiveness: The parable shows no one is too sinful for God’s forgiveness (Matthew 21:31-32). Only our own stubborn pride and lack of belief can keep us from it.

And the parable of the two sons isn’t the only place in the Bible where we find two parallel types of people.

Additional Scripture examples of the “two sons”

Several people in the Bible mirror the two sons represented in Matthew 21:28-32. Let’s do a quick Bible study of three instances:

1. The Good Samaritan vs. the priest and Levites
2. The Prodigal Son vs. the older brother
3. David vs. Saul

We find the Good Samaritan parable in Luke 10:25-37. In this story, a Jewish man gets left for dead by robbers. Three men pass by the injured man: A priest, a Levite, and a Samaritan.

The priests and Levites are like the second son (or religious leaders). They claim to be servants of God, yet they won’t even stop to serve someone in need. Meanwhile, the Samaritan is like the first son (harlots and tax collectors). Though hated by the Jews, he even puts himself in potential danger to help one of them.

There’s also overlap between the two sons parable and the prodigal son parable in Luke 15:11-32. The first son (tax collectors and harlots) is like the younger, or “prodigal” son. And the second is like the older brother (religious leaders).

The younger son leaves his father’s house to live a rebellious life on his own terms. But he later has a change of heart and humbly returns to his forgiving father. Meanwhile, the older brother doesn’t think his fallen brother is worthy enough for his father’s love.

The lives and mindsets of David and Saul are two real-life examples of these two sons. David is like the first son and Saul, the second. God anoints them both as King over His people at different times. And God sent them both messengers to guide them. They also both make dreadful mistakes (1 Samuel 13:13, 2 Samuel 11:26-27).

David always humbled himself, took ownership, and asked God for forgiveness (2 Samuel 24:10, 12:13). As a result, the Bible calls him a man after God’s own heart (Acts 13:22).
Meanwhile, Saul was stubborn and not humble (1 Samuel 15:22-23). He never gave true confessions—but tried to justify himself or blame others for his mistakes (1 Samuel 13:11-12; 15:24). And like the religious leaders, Saul even tried to kill God’s chosen (1 Samuel 18:10-11).

As a result, though he and David were both sinners, Saul was completely lost (1 Samuel 15:16:14; 28:6).

Now let’s see how this translates to today.

How the Parable of the Two Sons applies today

The lessons of this parable (like all the parables of Jesus) are timeless. The sons represent two general groups of people that live life in this world. And at the Second Coming, it will be revealed who is who—and those hiding behind religious facades and personas will be exposed.

Whatever “class” we might feel more familiar with—or whichever class other humans might assign to us—this parable gives up hope that we can come to God for forgiveness in whatever state we’re in.

Throughout our lives, we could bounce back and forth between groups. Sometimes we’ll be like the tax collectors and acknowledge our need for Jesus. Other times—maybe without even realizing it at the moment—we can become stubborn and proud, disregarding God’s will. We can even end up rejecting God’s workers if they don’t meet our standards or traditions.

But this parable has good news for both classes.

Jesus wouldn’t have told this parable if He didn’t care about the religious leaders. He wants to soften our stubborn human hearts (Ezekiel 36:26). Then we’ll respond to the Holy Spirit and follow. But it’s our choice. We must ask God for help in surrendering our will to Him every day (1 Corinthians 15:31).

It’s also clear Jesus has a special place in His heart for social outcasts. He tells all to come to Him—not only those who seem perfect (Matthew 9:12-13; 11:28). Jesus says, “Whoever comes to me I will never cast out” (John 6:37b, ESV).

God welcomes anyone who will believe and accept Jesus as their Savior.

The parable of two sons also reveals what true, faith-filled obedience to God is.

The chief priests appeared obedient by their religious knowledge and pious lives. But the sinners with all their baggage were more obedient simply by believing. And by obeying the call to repent.

God’s version of obedience means coming to Him and letting Him transform us. In the process, we’ll realize how much we need God’s mercy. And we’ll start showing His mercy to others (Hosea 6:6).

It’s not enough to call ourselves “Christian.” Christianity isn’t about names or appearances.
Both sons in the parable considered themselves sons of the Master vineyard owner. But only one took the role seriously by representing their father in the vineyard.

If we don’t represent our heavenly Father and show others the way to Jesus, are we really Christians?

What can get in the way of us representing God?

Anything can—even things that seem good. For example, our busy schedules, career goals, or a desire to protect our reputation can all blind us.

It’s easy to picture the second son as a slacker. But for all we know, maybe he was like Martha. She rushed her time with Jesus because she was “anxious and troubled about many things,” (Luke 10:41-42, ESV).

We can’t let our plans and personal importance become more important than obeying God (Luke 17:26-27).

So, what’s the secret to not becoming (or remaining) like the second son?

Both the Old Testament and New Testament promise that God can help us obey (Philippians 2:13, Ezekiel 36:27). But that requires connection. Jesus says if we keep Him at the center of our lives, He’ll work through us to bear good fruit (John 15:4). And we won’t end up withered like the fig tree—which looked good but lacked substance (John 15:6).

The parable also makes it clear God doesn’t want us to separate ourselves from Him when we make mistakes. In fact, we shouldn’t.

When the first son realized his mistake, he didn’t go and hide in shame for a few days. He immediately joined his father in the vineyard. Jesus can only forgive us and heal us if we come to Him in our broken state (James 4:8, 1 John 1:9, Proverbs 28:13). And He draws near to us when we come to Him in a humble spirit (Psalm 34:18).

The sooner we return to God, the sooner we can get to work in the vineyard. And that means connecting other struggling sinners with their Savior.

Obeying God’s will in our daily lives might feel like a sacrifice at first. But it brings lasting joy as we share the Gospel with others (Psalms 40:8; Acts 20:24).

Two Sons, Two Choices

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The parable of the sons comes down to two choices. We can pay lip service to God like the second son did. We can say we’ll serve Him, but resist His leading.

Or like the first son, we can acknowledge that we fall short and serve our Father in faith that He makes up for whatever we lack. It teaches us that God doesn’t compare us on an arbitrary “goodness” scale. He doesn’t measure prostitutes against Bible scholars. It’s about a humble spirit, a willingness to repent, and a longing to do God’s will.

In many ways, this parable is a wake-up call to us all. When we become Christians, it’s easy to get comfortable with religious routines. And if our focus drifts toward checklists and rituals, we become less attuned to the Holy Spirit’s leading.

God has millions of sons and daughters around the world who claim to believe in Him. And we all represent His kingdom of heaven here on earth. Yet, Jesus told His disciples, “The harvest is abundant, but the workers are few” (Matthew 9:37, CSB).

We also know from this parable that there’s hope for every person alive. Jesus longs to heal, forgive, and adopt us as sons and daughters—no matter what we’ve done. So let’s take Him up on His offer.

And when we understand what it means for God to adopt us through Jesus Christ, we’ll want to share the good news as we serve others. That’s what Jesus commissions us to do in His vineyard (Matthew 28:18-20).

Want to know more about why Jesus taught with fictional stories?

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