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The Gambler and the King

Investigating / exploring 2 of Jesus’s most difficult parables that teach us about the strange world of Grace.

“Old David!!” A couple weeks ago, someone came up to me and said “Loved your sermon on Sunday. That was almost like the old David!!” Haha. What the heck is that supposed to mean?! I’m 36. I’m already past my prime?!

Last Week: The King and His Money / This Week: How to Gamble and Win


What are the parables? They are not simple illustrations.

Clever little stories. Sometimes he offered explanations, other times he didn’t. But they’re more than that. Invite us into looking at the world in a new way. – Through the lens of Grace.

Read bible – associate – good guy.

When we read bible, we tend to associate with good guy. Of course we’re the good guy! Brave Israelites & the wicked philistines. Of course we’re the israelites!!! And who’s the bad guy? Well your neighbor, boss, friend, spouse. Someone from another religion.

Parables – challenge things we already thought we knew. Teach us not only about the Kingdom, but also the King!

Jesus told parables not just to help you see, but to help you see slowly. Jesus told parables to keep people from seeing the truths of the Kingdom of God too quickly.

In the week leading up to Jesus’s death, he stopped telling parables, and spoke directly. And he was dead within the week.

Jesus was smart. Of all the other things he was, he was smart too. The Kingdom of God is so radically different than anything else that if it hits us too square, it freaks us out. It scares us.

Emily Dickenson – Tell all the truth but tell it slant.

Tell all the truth but tell it slant —
Success in Circuit lies
Too bright for our infirm Delight
The Truth’s superb surprise
As Lightning to the Children eased
With explanation kind
The Truth must dazzle gradually
Or every man be blind.

Parables is one of the ways Jesus dazzles gradually. Because if he didn’t, his teachings were so radical that we’d reject it.

Some people will never learn anything for this reason: because they understand everything too soon. (Alexander Pope 18th century poet)

We tend to think of the truth as something we’ve already found. Boom! Done! Now I know the truth! So glad that’s done. We file it under the category ‘Things I know.’ But parables come and challenge what we thought was already clear.

Jesus never used the word Grace

You may not know this, but Jesus never once uses the word ‘grace’ in the gospels. Not once. But his LIFE was the embodiment of grace. Jesus was the grace of God walking in sandals. Everything that Jesus did was an expression of grace. – Turning water into wine, healing the leper, raising the dead. Everything Jesus did was an expression of grace.

Parable – Dishonest Manager

This parable directly follows the parable of the prodigal son. It’s literally the next verse. The prodigal son is possibly the most fameous of all of Jesus’s parables. This one MIGHT be the least. That vast majority of Christ followers have no idea what to do with this parable.


“What’s the moral of the story?” None. This story is not concerned with morality. Jesus is not teaching us how to behave, he’s teaching us something about the strange world of grace.

Luke 16:1-8

Jesus told his disciples: “There was a rich man whose manager was accused of wasting his possessions. (Luke 16:1)

So he called him in and asked him, ‘What is this I hear about you? Give an account of your management, because you cannot be manager any longer.’ (Luke 16:2)

“The manager said to himself, ‘What shall I do now? My master is taking away my job. I’m not strong enough to dig, and I’m ashamed to beg— (Luke 16:3)

Which sounds like a great country song. “Too weak to dig and too proud to beg.”

“Hmmm… I’m about to lose my job. What should I do?”

I know what I’ll do so that, when I lose my job here, people will welcome me into their houses.’ (Luke 16:4)

“So he called in each one of his master’s debtors. He asked the first, ‘How much do you owe my master?’ (Luke 16:5)

“ ‘Nine hundred gallons of olive oil,’ he replied. “The manager told him, ‘Take your bill, sit down quickly, and make it four hundred and fifty.’ (Luke 16:6)

“Then he asked the second, ‘And how much do you owe?’ “ ‘A thousand bushels of wheat,’ he replied. “He told him, ‘Take your bill and make it eight hundred.’ (Luke 16:7)

“The master commended the dishonest manager because he had acted shrewdly. For the people of this world are more shrewd in dealing with their own kind than are the people of the light. (Luke 16:8)

Here’s the summary:

There’s a rich man. Lots of parables start that way, have you noticed? Owns land. That’s how he’s rich. Rents out his land to farmers who work the land. Pay their rent in ‘produce’. One in olive oil, one in wheat

He’s so successful that he needs to hire someone to manage the whole thing. Collect the rent, etc. Let’s call him George.

Well it turns George is a crook. ‘Wasting’ the possessions of the owner. Probably a kind of embezzlement. A side business – taking some of the produce and selling it on the side. He gets busted.

So Mr Thompson calls George in and says ‘I know what you’ve been doing and you’re fired. I’ll give you a few days to get your affairs in order, and I’ll need a full account of the books so I can see what’s been happening here.’

George panicking. “Too weak to dig and too proud to beg.” “I’ve got it!” One last trick. – It’s brilliant. In fact at the end – Mr Thompson compliments him for being so smart and sneaky. Many translations say ‘Shrewd’ but that’s just cuz the translated were nervous at using the word ‘Wise’, but that’s what the word is.

It’s the same word Jesus uses the he talks about ‘The WISE man who builds his house on the rock.’ You don’t say the shrewd man. Anyway, george is smart.

He’s the scheme.

“Hey Bob, what’s your rent here? Yeah, 900 jugs of oil a year? Well it’s your lucky day, Mr Thompson has lowered your rent – from now on, you only have to pay 450.'”

And so the farmer says “WHAT?! That’s the best news I’ve heard all month! Make sure to tell Mr Thompson thank for you me! Tell him his generosity has blessed my family!”

Same thing – Next guy 1000 bushels of wheat. – “We know things are hard right now, so Mr Thompson has agreed to make it 800.” – “Wow! Thank you so much!”

BTW the discount – 450 gallons of oil and 200 containers of wheat. – Are the same discount which is about 500 danari. Which is a big discount if you think a danari is 1 days wage. Think about how much you make in a day, multiply it by 500, that’s a big discount.

What he’s planning on is that by doing this, everyone is going to like him, and when he gets fired which he certainly will, he’ll be on everybody’s good side so he can kind of just go from house to house.

Like it says: he was doing this so he would be ‘welcomed into people’s homes.’

And to close the parable, the master COMMENDS the dishonest manager for acting wisely. “For the people of this world are more shrewd in dealing with their own kind than are the people of the light.”

And Jesus gives no interpretation.

Julian the apostate – Roman Emporeor tried to bring the roman empire back into peganism after constantine had led the empire to Christianity.

So no fan of Christianity. He LOVED this parable. He would point to it and say “See!! Jesus isn’t as moral as you all say he is.” And can’t you see that on the surface, he has a pretty good point.

If you try and make this a nice lesson on morality, you run into the problem of Jesus commending a crook for dishonest behavior.

But if you take it for what it is, which is an edgy, almost scandelous story on the nature of grace, you’re on the right track.

What to say? LOTS!

Ok, so what to say about this parable? LOTS!

Parable 4.

So one thing to understand is that this parable is parable 4. of a group of 4 parables that Jesus tells in succession.

  • Lost Sheep (Luke 15)
  • Coin (Luke 15)
  • Son (Luke 15)
  • Dishonest Manager (Luke 16)

Shame ≠ same chapter

It’s a shame we didn’t put them in the same chapter, I think that would have been helpful. Keep in mind that chapter and verse were added later, they weren’t part of the original manuscripts. They’re just there for convinience. You wouldn’t have otherwise been able to flip to a specific section like you can now.

All 4 parables set out to answer this question: What is God like?

I think in a way it’s like a movie franchise with 4 films. People like the first one, people like the second one, they LOVE the third one, and they HATE the fourth one. I can picture people saying “Jesus, it was a great trilogy!!!! And you totally ruined the franchise by adding a fourth!!!”

1st glance – nothing.

At first glance, these stories appear to have nothing to do with each other.

  • Sweet story – about a shepherd looking for his lost sheep
  • Sweet story about a lady who lost her coin.
  • Sweet story – loving father who just wants his son come home
  • Sneaky story – crook – gets commended – dishonest behavior.

But lets look beyond the surface and see that they have a lot in common.

Jesus is a great storyteller. He could have been a great novelist. It seems to me like with these 4 parable, which each new story it gets more and more scandalous till Number 4 where it’s almost absurd.

  1. A shepherd leaving 99 sheep to find 1. Sounds like a bad shepherding decision. But still mostly sweet.
  2. Woman searching for her lost coin. Can anyone guess why this would have been scandalous? Comparing God to a woman?! Oh man.
  3. Prodigal Son who squandered fathers money and brought shame on family, to be welcomed back in without even offering an apology. That’s just madness.
  4. Employee caught embezzling money being commended as ‘wise’.

Similarities w/ Prodigal Son:

So let’s just focus on this story and the story of the prodigal son.

Both main characters betray someone’s trust.

In both that parable of the prodigal son and the parable of the dishonest manager, we both have a person who betrays someones trust.

Both misuse someone else’s possessions.

Both misuse somebody else’s possessions.

Both are failures.

Both failures – one has failed at being a son and the other has failed at being a manager.

Both are saved by mercy or not at all.

And in the end: One receives an unexpected party and the other receives an unexpected compliment. Both teaching us something about the strange world of grace.

Stop Flirting

Ready for me to stop flirting and just tell you what it means?

So again, George is getting fired so he goes to these people and (without prior authorization) cuts their debt to Mr. Thompson, by sometimes as much as 50%. Ok, so what’s he doing? And what’s to stop Mr Thompson from just going back and undoing?

George is gaining the approval and gratitude of others by saying that he and Mr. Thompson had their best interest in mind and lowering their rent.

Imagine in this happened to you – let’s say you’re renting a house. And it’s owned by a man named Mr Thompson. And then one day, there’s a knock on the door, and it’s George, he’s the guy who collects rent for Mr Thompson, and he says ‘Hi David, so you rent this property from Mr Thompson is that right? Yes. And how much is your rent. I say “$900 a month” and he says ‘Ok cool. So I was just talking to Mr Thompson and we agreed that times are pretty tough out here, we thought you guys could use a break, so from now on, just pay us $450 a month.

Put yourself in that situation. How would you feel? Picture someone coming, and appearing to represrent the landlord, and lowering your rent by half, for no other reason than to be kind and generous.

I could even imagine them having a party that night and saying ‘A toast to Mr Thompson! Who lowered our rent because he loves us! And here’s to George who’s always looking out for us!’

Here’s – Brilliant.

Here’s where the plan gets brilliant. George is sneaky.

Mr Thompson finds out. Of course. This is all part of the plan. He finds out George has lowered the rent of his renters. George is a gambler. He won’t have to dig or beg. – He’s going to be a friend of everybody. And he’ll be welcomes in wherever he goes. He can kind of move around from house to house.

Either salvation or jail.

Now Mr Thompson has a choice – two options

  1. Throw George in jail and go around and tell everyone that their rent didn’t actually go down. – George was unauthorized.
  2. “Dang, George is clever. – He’s put me in a corner here. Dang it. Boy that George sure is lucky I’m kind and generous. I guess I’ll just enjoy my new reputation as the best landlord in town and let him get away with it.”

High Stakes gamble.

He’s betting his whole life of 1 thing. What is that one thing?

Betting whole life on one fact: That Mr Thompson is generous. Kind. Merciful. So George was going around delivering good news about Mr Thompson. “Good news! He’s going to lower your rent!”

The manager (George) has gained public favor for himself and for the master (Mr Thompson) as a generous benefactor; if the master punishes the manager now, it would appear to the public that he were doing so because of the manager’s benevolent act. The criminal manager could be jailed, but he wisely stakes everything on his master’s honor as a generous man.
Dr. Craig Keener – NT Professor

SUMMARY George gambled everything on the grace and mercy of Mr. Thompson. And he won.

You might be thinking “HUH?!”

Might be because you’re still looking it at a lesson in morality. Where you’re expecting George to be teaching you how to behave. That’s not whats happening.

Let me try to make it really basic – let’s pretend you were explaining it to a 12 year old. You could say something like : “George isn’t teaching you how to behave. Mr. Thompson is teaching you something about God.”

George isn’t being complimented for being a crook, he’s complimented for gambling on the goodness of Mr. Thompson.

It’s doing precisely what the parable of the prodigal son is doing. The prodigal son is not telling you how you as son ought to behave. So get your inheritance and spend it on booze and women. The story is there to teach you something about the father. And this parable is the same, it’s not trying to tell you how to behave, it’s trying to teach you something about the strange world of grace.

Backstory :

The backstory of this story is this: Jesus would always do this scandalous thing : Sitting down and eat with famous sinners.

Pharisees, these were the good guys in a sense. They were the moral ones. They would look on with scorn. “This man receives sinners and eats with them.” Jesus responds by telling these stories. A story about Lost Sheep, a story about a lost Coin, a story about a lost Son, a story about a dishonest manager.

This helps explain why Jesus was so popular with self-proclaimed sinners.

“Sinners” have a certain advantage.

Sinners have a certain advantage – Jesus never commended sin. But self-admitted sinners have an advantage over people who think they’re just the best all the time. B/C sinners know their only options is to throw themselves on the mercy of God. – That they’re going to make it by grace or not at all. Just like George did.

“Good” people ≠ need gamble on grace.

“Good” people on the other hand, don’t feel the need to gamble on grace. “Good people” always struggle with the idea, we don’t say it, we just think it: “I’m a good guy! I lived a good life! So maybe God kinda owes me.” That will never work.

Grace is good news for people who know they need it and bad news for people who don’t know they need it.

For Example: Let’s imagine Bank of America comes out and says “Hey everyone! We thought about it, and everyone who owes us money, we’re cancelling your debt. We’re bringing back the year of jubilee. Now who would be the people most happy about that? The people who know they have a debt to the bank of course! Let’s say according to your records, the bank owes YOU money. Would it be good news? No of course not.

People who are good in their own eyes don’t need a story like this. This just muddies the water. “You’re gonna let those people in? Ew. Gross.” But if you know you’re a sinner, and you’re going to be saved by grace or not at all. This story the best news ever!

This is what Jesus is doing when it comes to the kingdom of God. He’s saying even guys like George can gamble on my goodness and they won’t be disappointed.

“I never bet against the mercy of God–I don’t like my odds.” (REV. JOSEPH BEACH – Denver)

George bet on the goodness of Mr Thompson and he won big.

Sons of Light

“The master commended the dishonest manager because he had acted shrewdly. For the people of this world are more shrewd in dealing with their own kind than are the people of the light. (Luke 16:8)

Interesting phrase “People of the light.” Some translations say ‘Sons of light’. It’s a phrase Jesus hardly ever uses. He uses it twice. Once here, once in John 12. It’s controversial phrase. We didn’t understand it for a long time until the dead sea scrolls.

We learn about this phrase from the war scroll which is part of the dead sea scrolls. There was a wide-spread belief in Jesus’s day that there was this huge war coming. And it was going to be between the sons of light and the sons of darkness. And the sons of light were going to win the war and bring righteousness to the earth.

This was a belief held by the essenes, and many of the pharisees. Common language ‘The sons of light’. The forces of darkness vs the forces of light. And people who would tell these stories, they always saw themselves as what… ‘Sons of Light’. Of course. Of course we’re the good guys!

Jesus comes and says something quite provocative: “The Sons of Light aren’t very smart.” Now that doesn’t shock you because that’s not a group you identify with. But this was quite provocative. For our day, imagine Jesus coming and saying ‘You know, those evangelical Christians aren’t very smart.’ All of a sudden you’re thinking “What?!?!”

He’s saying ‘You know the self-professed good-guys are actually not very smart.’ – Why? Because they trust in their own goodness. Jesus said at the end that, in a certain way, self-proclaimed sinners are smarter than the self-righteous. “The Sons of Light” The Sons of Light can be tempted to lean on their own goodness. Sinners know they need mercy.

It’s smarter to bet on God’s mercy than on your goodness.

Christianity is not a religion where do-good-ers get by by doing good.

Even though that’s what the pharisees wanted. That’s also what the older brother in the parable of the prodigal son wanted. But Jesus is coming and saying the exact opposite. That the wise ones are the ones who know how much they need to mercy of God.

So if Christianity is not a religion where do-good-ers get by by doing good, then what it is?

Christianity is the mercy and grace of God found in Jesus Christ.

Nothing more, nothing less. If you earn it, it’s not grace. Christianity is betting everything on the mercy and grace of God and coming up big.

This parable means a lot to me, B/C mercy is the reason I’m here. And it’s also the reason you’re here. You bet your whole life on the grace of God, and you won.

In fact, I wonder how many of us today would say “If it were not for the mercy and grace of God, I don’t know where I’d be.”


1. We miss the heart of Christianity the moment we lean on our own goodness.

Because of that, no matter how broken, no matter how messed up you are, you can be confident that you have just as much right to be at the table of Jesus as anybody else.

2. As we follow Jesus, we seek to offer his curious grace to others.

We’re consistently committing ourselves to treat people better than we deserve. Because that’s how we’re treated. We are in the business of forgiving debts, because our debt has been forgiven.

If – feel far – God

As we close – If you feel far from God tonight – Jesus comes and offers you a seat at his table. Yes it’s scandalous. Yes it makes the religious people nervous, but that’s who his is. You come, as the crook, gambling on his grace, and it meets you there every time.

Which of course brings us to the cross. The cross is not just 1 thing, it’s the center of the Christian faith and EVERYTHING flows from that. But one thing the cross is it’s God cancelling the debt that you could never pay.

Closing Statement: (let’s go through all 4)

What is God like?

  • God is like a shepherd looking for his lost sheep, who when he finds the sheep joyfully puts it on his shoulders and carries it to safety.
  • God is like the woman searching the house for her lost coin, who frantically looks day and night to find her precious coin and rejoices when it’s found.
  • God is like the father who eagerly waits for his son to come home, and showers him with kisses when he does.
  • God is like the manager who is abounding in grace and mercy, even to a crook like me.