Parable of the Two Sons Explained

A changed mind.

That’s what it would have taken—a shift in perspective—and the religious leaders of Jesus’ day could have altered the trajectory of their lives and begun the process that leads to eventually entering the Kingdom of God.

Two thousand years have passed, and that barrier hasn’t changed. The fundamental roadblock to meaningful spiritual growth has always been an unwillingness to change our minds, surrender our own way of thinking and embrace a different way.

Jesus’ parable of the two sons, found in Matthew 21:28-30, drives this point home.

Context and the parable of the two sons

Jesus’ original audience for this parable was the chief priests and the elders (Matthew 21:23). They were considered the religious elite—men who thought they were a cut above the rest.

In reality, they were deluded about how spiritual they were. They needed forgiveness as much as everybody else, including the tax collectors and harlots they notoriously looked down on.

So this parable was Jesus’ attempt at giving them a blunt reality check: “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” (Matthew 21:28-30).

One son outright refuses—rebellious and obstinate—but later has a change of heart and does what he was asked. The other son agrees enthusiastically—talks big—but in the end, never shows up. Polar opposites.

Jesus’ question to the chief priests and elders was simple: “Which of the two did the will of his father?” (verse 31).

They couldn’t argue with the obvious: “The first.”

Yet one of the most encouraging takeaways from the parable is that God always honors true repentance. And with that answer, they backed themselves into a corner. They had just acknowledged a universal truth they had been failing to apply to themselves all along: who you are, or who you claim to be, means nothing. What matters is what you do.

Jesus wasted no time in making the connection for them. He told them that the tax collectors and the prostitutes would enter the Kingdom of God ahead of them. “For John came to you to show you the way of righteousness, and you did not believe him, but the tax collectors and the prostitutes did. And even after you saw this, you did not repent and believe him” (verse 32, New International Version).

Did the shoe fit?

Let’s take a closer look at the second son to see why Jesus used him to illustrate the religious leaders.

There’s no doubt the second son had all the trappings of being the model son. First, he gave the right answer to his father: “I go.” This was apparently a family-owned vineyard where children were expected to help care for the crop.

But that’s not all. He also addressed his father as “sir” (kyrios in the Greek), a word that carries the sense of “my lord.” This son didn’t just agree to work; he seemed to show deep respect for his father.

All the signs were there—he gave the expected answer, displayed the right intent and showed a measure of deference.

But when it came time to act, he did nothing.

And in that, the second son became the spitting image of the religious leaders. They proudly declared themselves to be children of Abraham, claimed to have the righteousness God required and spoke as if they were fully devoted to His service.

But did they actually do God’s will? Not really. Not underneath. They were all about outward show and big talk.

And Jesus didn’t have to look long and hard for proof. He pointed them to the perfect example—their response to John the Baptist.

John’s message can be summed up in one word: repent (Matthew 3:2). Change your mind. Not about frivolous things, not about harmless personal preferences, but about who you are at your core—about the choices you make, the path you walk, the sin you cling to.

Repentance is about more than just feeling bad. It’s about doing something. It means a complete course correction—turning away from sin and aligning with God’s standards.

And that was the issue for the chief priests and elders. That kind of action required admitting they were wrong. It required changing their minds.

They weren’t willing to do that.

The ones who truly served God

There is a positive example to follow in all this. It’s the one set by the tax collectors and harlots, who more broadly represent the repentant sinner.

Because their sins were more blatant and obvious, they’re depicted as the son who openly rebelled against his father and refused to work in the vineyard. But the difference? They eventually recognized their wrongs, changed their minds, and did what was asked of them. As Jesus put it so simply, they regretted what they had done.

We don’t have the exact stories of the individuals Jesus was referring to, but Luke gives us a glimpse of how regret was demonstrated among those who listened to John.

“So the people asked him [John], saying, ‘What shall we do then?’

“He answered and said to them, ‘He who has two tunics, let him give to him who has none; and he who has food, let him do likewise.’

“Then tax collectors also came to be baptized, and said to him ‘Teacher, what shall we do?’

“And he said to them, ‘Collect no more than what is appointed for you.’

“Likewise the soldiers asked him, saying, ‘And what shall we do?’

“So he said to them, ‘Do not intimidate anyone or accuse falsely, and be content with your wages’” (Luke 3:10-14).

Apparently, these groups didn’t think it was enough to profess something or make an empty claim. This was repentance in action. They recognized that their behavior and their past way of thinking—their sense of right and wrong—needed to change.

And instead of just talking about it, they actually did something about it.

The result would be an immense reward. They had Jesus’ promise that if they stayed the course, they would one day enter the Kingdom of God—ahead of those who refused to change their minds.

Jesus said early on in His ministry, “Not everyone who says to Me, ‘Lord, Lord,’ shall enter the kingdom of heaven, but he who does the will of My Father in heaven” (Matthew 7:21).

His will is that we all repent and seek out the forgiveness that comes through His Son, Jesus Christ.

Lip service versus true service

The parable of the two sons is about two kinds of people: those who claim to obey God but don’t follow through and those who initially reject Him but later come to repentance. Jesus makes it clear which group is preferable.

Which one do we identify with?

Change isn’t easy. One of the big obstacles the religious leaders ran into was their self-righteousness. They were so convinced of their own merit that they couldn’t see their own flaws. Their pride blinded them to their true spiritual condition.

And because they didn’t see their need to change, they couldn’t change.

But their spiritual gaps were there. And in the end, it cost most of them the opportunity to become disciples of Jesus Christ.

Yet one of the most encouraging takeaways from the parable is that God always honors true repentance. Nowhere does Jesus sugarcoat extortion, adultery or any other sin. Those are real offenses—behaviors that make us ineligible for the Kingdom of God (1 Corinthians 6:9-10).

But the core of the gospel is this: those sins don’t have to define us. We aren’t locked into our past. We can take action. We can do something about it.

And it starts with changing our minds.

“The time is fulfilled, and the kingdom of God is at hand. Repent, and believe in the gospel” (Mark 1:15, emphasis added).