The Rich Young Ruler & Zacchaeus

Zacchaeus and the Rich Young Ruler: Two Encounters With Jesus, Two Very Different Responses

Katie Brubaker: Welcome to the Smarter Generosity podcast. I’m Katie Brubaker.

Eric Fleshood: And I’m Eric Fleshood.

Katie: I’m really excited about our conversation today.

Do you remember when we were little kids in Sunday school and learned that song about Zacchaeus? “Zacchaeus was a wee little man,” and he climbed up into a sycamore tree because he wanted to see Jesus.

Then Jesus says, “Zacchaeus, you come down!” As though He’s angry with him, right? That was always the best part of the song, when everybody shook their finger.

Eric: I remember that.

Katie: That’s what I grew up knowing about Zacchaeus.

But in a previous episode, we talked about the rich young ruler. And not too long ago, somebody suggested that it would be interesting to compare these two men because they had similar starting points but very different outcomes.

I had never really thought about that before.

Eric: It is a fascinating comparison.

We’re actually going to do something a little different today. We haven’t come into this conversation with a fully developed script or all the answers worked out.

We thought it would be interesting to explore these two stories together, in real time, and see what we discover.

What was different about these men? Why did they respond so differently to Jesus?

Katie: Because I think that Sunday school song is a little misleading when it comes to Zacchaeus.

Eric: In what way?

Katie: The more I’ve learned about Zacchaeus, the more I like him.

For one thing, the song ends with Jesus saying He’s coming to Zacchaeus’s house. But that’s not where the actual story ends. We miss everything that happens afterward.

So maybe that’s a good place to start. Let’s walk through both stories.

Eric: Absolutely.

Katie: Zacchaeus was a tax collector, which meant he wasn’t a very popular person.

He was working within the Roman tax system, which made him appear to be aligned with the people oppressing his own community.

Tax collectors also had a reputation for collecting more than they were required to, and Zacchaeus was very wealthy.

So here’s a man who has wealth and power, but probably isn’t particularly well-liked.

Then he hears that Jesus is coming through town.

He’s curious and wants to see Him, but there’s a large crowd, and Zacchaeus is short. Scripture actually tells us that.

So he climbs a sycamore tree to get a better view.

As Jesus passes by, He looks up at Zacchaeus, calls him by name, and tells him that He’s coming to stay at his house.

To our modern Western ears, inviting yourself to someone’s home might sound a little rude. But in that culture, this was an incredible honor.

Zacchaeus is overjoyed. He comes down from the tree and welcomes Jesus into his home.

Eric: And then what happens?

Katie: He encounters Jesus personally, and something changes.

Zacchaeus recognizes his wrongdoing and responds with this extraordinary act of generosity and restitution.

He’s ready to make things right with the people he’s harmed.

Eric: That’s right.

The story is in Luke 19, and Zacchaeus says to Jesus:

“Look, Lord! Here and now I give half of my possessions to the poor, and if I have cheated anybody out of anything, I will pay back four times the amount.”

Think about that. Four times the amount.

I wonder how that compares with what the Old Testament law required in circumstances like his. I’d be curious to explore that further.

But what’s immediately clear is that Zacchaeus is having an extraordinary response to his encounter with Jesus.

Katie: And I love what Jesus does here.

Imagine the reaction of the crowd when Jesus points to Zacchaeus and announces that He’s going to spend time with him.

This is probably the last person anybody would expect Jesus to choose.

Zacchaeus was seen as a sinner and a traitor to his own people. And Jesus singles him out, calls him by name, and chooses to spend time with him.

I’m sure the crowd wasn’t thrilled.

Eric: Right. He would have been considered one of the most irreligious people in that community.

And yet look at what happens.

Zacchaeus is so moved by his encounter with Jesus that he voluntarily gives half of his possessions to the poor.

Nobody asked him to do that.

Katie: That’s the part I find so remarkable.

Eric: It was his spontaneous response to getting to know Jesus.

Now, should we look at the other story?

Katie: Absolutely. Let’s talk about the rich young ruler.

Eric: This story appears in several places in the Gospels. I’m looking at Matthew 19, where he’s described as a rich young man.

He comes to Jesus and essentially asks, “Teacher, what good thing must I do to get eternal life?”

Jesus directs him toward the commandments.

He mentions commands such as not murdering, not committing adultery, not stealing, and not giving false testimony.

And the young man responds by saying that he’s kept all these commandments.

He’s essentially saying, “I’ve done all of that. I’ve checked those boxes. What am I still missing?”

Jesus then tells him that if he wants to be perfect, he should sell his possessions, give to the poor, and come follow Him.

And then we get one of the saddest verses in Scripture.

Matthew 19:22 says that when the young man heard this, he went away sad because he had great wealth.

Jesus then goes on to talk about how difficult it is for a rich person to enter the kingdom of heaven, using that striking picture of a camel passing through the eye of a needle.

What a contrast between these two encounters.

Katie: Before we get too far into his response, I want to ask about the word perfect.

Because we know that human beings can’t earn salvation through their own perfection.

And yet Jesus tells this man, “If you want to be perfect,” and then gives him this instruction.

I’ve wrestled with that before.

What do you think Jesus is getting at?

Eric: I think Jesus is speaking to a man who believes he has the ability to achieve perfection through obedience.

He seems to be striving for that.

He’s saying, “I’ve kept all these commandments. Now tell me what else I need to do.”

He wants another rule he can follow, another box he can check.

So Jesus gives him something extraordinary.

He tells him to sell his possessions, give everything to the poor, leave behind the life he’s built, and follow Him.

It’s a complete change of direction.

And the young man walks away sad because he has great wealth.

Katie: What’s interesting to me is how differently Jesus approaches these two men.

With Zacchaeus, Jesus doesn’t give him a list of instructions. He simply tells him that He’s coming to his house.

But with the rich young ruler, Jesus gives him a specific instruction that addresses the very thing standing between him and following Jesus.

The young man calls Jesus “Teacher.” He’s approaching Him as someone who can tell him what he needs to do.

And Jesus recognizes that his wealth has a hold on his heart.

That’s the thing he isn’t willing to release.

Eric: I love what you’re pointing out because someone could read this passage and come away thinking that Jesus is incredibly demanding.

They might ask, “How could Jesus ask someone to do that? Is He asking all of us to sell everything and give it away?”

But what you’re recognizing is that Jesus’ heart is for this man.

He’s trying to rescue him from his enslavement to wealth.

Katie: Which is what He was doing with Zacchaeus.

Eric: Exactly.

But the results were very different.

These two men started in somewhat similar circumstances. Both were wealthy. Both held positions of influence.

But they would have been perceived very differently by the people around them.

Katie: The rich young ruler probably would have been seen as someone who had God’s favor.

He had wealth and social standing, and he appeared to be religiously faithful.

Zacchaeus, on the other hand, would have been viewed as a traitor to his people.

Eric: That’s right.

Katie: Do you think those different backgrounds influenced how they responded to Jesus?

Eric: That’s a great question.

They certainly came from different backgrounds, and Jesus understood each of them.

But I think the more interesting difference is how they approached Him.

The rich young man comes to Jesus looking for something to do.

Katie: That’s what he’s asking for.

Eric: Exactly. So Jesus responds to the kind of question he’s asking.

But Zacchaeus doesn’t come to Jesus asking, “What must I do?”

What is Zacchaeus doing?

Katie: He seems genuinely curious.

He wants to see who Jesus is.

And then he appears completely surprised that Jesus singles him out and wants to spend time with him.

I think that personal encounter is what brings about his response.

He’s getting to know Jesus rather than asking Jesus to give him something to accomplish.

Eric: That’s an important distinction.

The rich young man comes looking for a rule to follow.

His question is essentially, “What can Jesus tell me to do so that I can receive eternal life?”

But Zacchaeus seems much more interested in knowing who Jesus is.

And Jesus responds by creating an opportunity for fellowship.

He says, “Let’s go to your house. Let’s spend time together.”

I think that’s a significant difference.

Katie: And isn’t that just like us?

I know I can approach my spiritual life from that same performance-oriented mindset.

I want to know what to do.

Give me the checklist.

Did I read my Bible? Did I pray? Did I do the things I’m supposed to do?

It’s easy to focus on accomplishing spiritual tasks rather than taking time to encounter Jesus Himself.

Eric: Let me ask you something, Katie.

Which of these two men would you rather be?

Would you rather live like the rich young ruler or like Zacchaeus?

Katie: Well, I’d like to start out with everything the rich young ruler had and be wise enough to respond like Zacchaeus!

But that’s not usually how it works.

The rich young ruler had wealth, status, and what appeared to be a respectable religious life.

Zacchaeus didn’t have that kind of reputation.

But when it came to their encounters with Jesus, their hearts responded very differently.

I’d obviously much rather experience what Zacchaeus experienced.

Eric: Although we shouldn’t give Zacchaeus too much credit for who he was before that encounter.

Remember, this was a man who had likely cheated people out of their money.

He was participating in a corrupt system and had benefited tremendously from it.

That’s the man who climbed into the tree.

Katie: Absolutely.

But when he encountered Jesus, he responded.

It reminds me of Paul’s conversion.

Before Paul became a follower of Christ, he had done terrible things. But then he encountered Jesus, and everything changed.

There’s a transformational moment in both stories.

Zacchaeus received Jesus.

Eric: Literally.

He received Jesus into his home.

He welcomed Him and entered into fellowship with Him.

And look at the freedom and joy that followed.

Who wouldn’t want to live from the heart the way Zacchaeus does in this story?

Katie: That’s what stands out to me.

There’s this incredible freedom in Zacchaeus’s response.

He’s not saying, “I have to do this because it’s the rule,” or “This is what I need to do to be a good religious person.”

He’s responding out of joy.

He freely offers half his possessions to the poor and promises to make restitution to anyone he’s cheated.

That response feels like an overflow of the grace and mercy he’s experienced through Jesus.

The word that comes to mind when I read the story is abundance.

There’s an abundance of joy, generosity, and freedom in his response.

Eric: I think that’s exactly why this comparison is so valuable.

When we start asking questions about stewardship and generosity, it’s easy to move immediately toward principles and rules.

What’s the command I’m supposed to follow?

What’s the biblical principle I need to apply?

What passage of Scripture should I memorize?

But these two stories remind us that it all comes back to a personal encounter with Christ.

There’s simply no substitute for that.

And sometimes that relationship answers questions in ways we never could have anticipated.

We may not even be asking the right questions to begin with.

Katie: I think that’s especially important when we bring the conversation back to biblical stewardship.

We can’t really separate faithful stewardship from our relationship with Jesus.

Whether we’re thinking about our finances, our families, or our marriages, stewardship is much bigger than checking off a list of responsibilities.

It touches our entire lives.

And that means it requires an ongoing relationship with Jesus, not simply a checklist of things we’re supposed to do.

Eric: That’s right.

And maybe this is a good place for us to finish.

We’d love for people to listen to this podcast. We’d love for these conversations to encourage people and help them grow.

But if someone has a choice between spending time listening to Eric and Katie talk about Jesus or actually spending time at the feet of Jesus, we’d much rather they spend time with Him.

That’s really the point we’re trying to make.

Katie, thank you for bringing this idea to the table. I’m glad we had the opportunity to explore these passages together.

Katie: Thank you, Eric. We’ll see you next time.

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This transcript has been edited for clarity and readability. Verbal fillers, repeated phrases, and post-recording conversation have been removed.