The Gambler (Tuesday Night Service)

Over the last few years, I’ve been on a journey. A journey to understand the life and teachings of Jesus.

Rare – teachings – Jesus.

As I’ve grown, I’m amazed by how rarely the teaching of Jesus come up in the typical Christian church. Safe stories of Jesus. Tons of Paul. A little Old Testament, and a little Jesus.

The words of Jesus should be the most important of all the words. Jesus is the only perfect picture of God.

Some issue – culture.

Some issue in culture – we use OT stuff, we use Paul stuff. But it’s strange how the words of Jesus don’t seem to come up.

Well what did Jesus say?

  • “Seems like Jesus is contradicting the OT” – Go with Jesus.
  • “Seems like Paul is contradicting Jesus” – Go with Jesus.


Designed to catch us in our blindness

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.

Parables – challenge things we already thought we knew.

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.

Tonight : Parable of the Dishonest Manager : The Gambler

NOT – MORALITY STORY “What’s the moral to 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

Then Jesus said to the disciples, “There was a rich man who had a manager, and charges were brought to him that this man was squandering his property. (Luke 16:1)

So he summoned him and said to him, ‘What is this that I hear about you? Give me an accounting of your management, because you cannot be my manager any longer.’ (Luke 16:2)

Then the manager said to himself, ‘What will I do, now that my master is taking the position away from me? I am not strong enough to dig, and I am ashamed to beg. (Luke 16:3)

I have decided what to do so that, when I am dismissed as manager, people may welcome me into their homes.’ (Luke 16:4)

So, summoning his master’s debtors one by one, he asked the first, ‘How much do you owe my master?’ (Luke 16:5)

He answered, ‘A hundred jugs of olive oil.’ He said to him, ‘Take your bill, sit down quickly, and make it fifty.’ (Luke 16:6)

Then he asked another, ‘And how much do you owe?’ He replied, ‘A hundred containers of wheat.’ He said to him, ‘Take your bill and make it eighty.’ (Luke 16:7)

And his master commended the dishonest manager because he had acted shrewdly; for the children of this age are more shrewd in dealing with their own generation than are the children of light. (Luke 16:8)

What to say?

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

Immediately follows – prodigal son.

1st – It’s important to know that this parable immediately follows the parable of the prodigal son.

Right after the parable of the prodigal son. Perhaps the most famous. This might be the least. Possibly the most confusing parable so most people just move on.

Linked – Jesus’ language. It’s a bummer it’s a new chapter, you know those are added later, but if they were together, it might have helped us understand.

But we had to celebrate and rejoice, because this brother of yours was dead and has come to life; he was lost and has been found.’ ” (Luke 15:32)

Then Jesus said to the disciples, “There was a rich man who had a manager, (Luke 16:1)

1st glance – nothing.

Ok, so at first glance, these two stories have nothing to do with each other.

  • A sweet story of a loving father and his son
  • A sneaky story of a dishonest manager.

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

Jesus is a great storyteller.


  • Both 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’s possessions. Both misuse somebody else’s possessions.
  • Both are failures – Being – son / manager. 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.

In end : One receives an unexpected party and the other receives an unexpected compliment.

Both teaching us something about the strange world of grace.


Here’s the summary:

Rich man.Owns land.

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’.

  • 1 in olive oil
  • 1 in wheat

Mr Thompson

So successful — manager.

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. And I need you to turn in 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.’

Anyway, george is smart.

Here’s the scheme.

“Hey Bob, what’s your rent here? Yeah, 100 jugs of oil a year? Well it’s your lucky day, Mr Thompson has lowered your rent – just pay me 50 jugs of oil.'” 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 100 containers of wheat. – “We know things are hard right now, so Mr Thompson has agreed to make it 80.” – “Wow! Thank you so much!”

What doing?

Ok, so what’s he doing? And what’s to stop Mr Thompson from just going back and undoing?

He’s getting the approval of others – as if he and Mr Thompson had their best interest in mind and so lowering their rent.

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

Imagine in this happened to you – let’s say you’re renting a house. 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.

If he pulls it off, he’ll be saved. If he doesn’t, he’s going to jail. 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. Either salvation or jail.

Mr Thompson – choice.

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. Well I guess I’ll just enjoy my new reputation as being kind and generous. And let him get away with it.”

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

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!”

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. No, he’s trying to teach you something about the strange world of grace.

Explain – 12 year old. :

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 complimented for being a crook, he’s complimented for gambling on the goodness of Mr. Thompson.

Backstory :

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

Pharisees – would look on with scorn. “This man receives sinners and eats with them.”

Jesus responds by telling these stories

  • Lost Sheep
  • Coin
  • Son
  • Dishonest Manager

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

Sinners have an 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 on the other hand, don’t feel the need to gamble on grace.

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

EXAMPLE. – Immigration This is not a political point, merely an EXAMPLE. But let’s pretend that there was a nation – let’s say the U.S. that decided – Amnesty for all illegal immigrants. What group of people would that be good news for? – Illegal immigrants. They would say ‘Woohoo!!! Cuz I knew the only reason I’d ever get in is if somebody would give me a break.’

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.

End :

And his master commended the dishonest manager because he had acted shrewdly; for the children of this age are more shrewd in dealing with their own generation than are the children of light. (Luke 16:8)

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 – need mercy.

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

“Sons of light” — No edge. “Evangelical Christians” Sinners – Smart

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.


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’re confident that you have just as much right to be here as anybody else.

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

Are you someone who treats people like they deserve? If you’re not treating people better than they deserve, don’t you dare say you’re speaking for Jesus. We’re consistently committing ourselves to treat people better than we deserve. Because that’s how we’re treated.

Jesus is full of Mercy.

That’s one of things the incarnation is about. So we can finally know what God is like.

Read matthew, mark, luke, John.

Mercy is almost overwhelming.

  • Merciful to sinners, tax collectors, prostitutes,
  • Merciful to Peter – betrayed Him.
  • Merciful to Matthew – corrupt tax collector.
  • Merciful to Simon – Violent Revolutionary
  • Merciful to the Woman caught in adultery.

The only people that Jesus was not merciful toward was people who were unmerciful.

Thus – beatitude “Blessed are the merciful, for they shall receive mercy.”

Jesus is consistently merciful towards even the most horrific of sinners. Provided that their sin is not being unmerciful.

Here’s my advice: If you’re going to be a sinner, pick a sin other than being unmerciful. Certainly seems to be a sense that the severity you use with other people is the same severity that you receive.

For if you forgive other people when they sin against you, your heavenly Father will also forgive you. 15 But if you do not forgive others their sins, your Father will not forgive your sins. (Matthew 6:14)

That sobers me up REAL quick.

Practical example

Let me try to think of a practical example:

Especially in a time of change, which is what we’re in, how many people would admit that there’s things that are wrong in our nation?

MOST of us WANT the broken things here to be made right.

And that’s a Godly desire – “Blessed are those who hunger and thirst for Righteousness and Justice”

In our WANTING to fix what’s broken, there will be disagreements on how that should be done.

We’re americans in here. Most of us.

  • How many people know there’s things in America that are broken?
  • How many people in here have an idea on how it can be made right?

How many of you know that not everybody agrees with your idea?

So you have 2 people, sitting right next to each other in Outlet in 2016 and have drastically different ideas of what constitutes justice.

So what we do? – Offer each other MERCY.

“Passion for justice can become a vicious battleground where people get hurt. And even separate good friends.”

You can say the right thing in the wrong spirit, and be the wrongest person in the room.

I know wrongest isn’t a word, but it didn’t have the same PUNCH when it’s grammatically correct.

When the longing for justice banishes mercy, we have abandoned the Jesus way.

B/C again, mercy is the reason you’re here. You gambled on the grace of God, and you won.


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.

Presence of God – great equalizer.

The Good News of the Gospel of grace cries out: we are all equally, privileged but unentitled beggars at the door of God’s mercy! (Brennan Manning)

The table of the Lord is the great equalizer. Because no matter how Holy you are, no matter how long you’ve been following God, you come to his table simply because he invites you.

As close, spend a minute with Him – finding your way to gratitude. – We’re all capable of gratitude, and we all have much to be grateful for, but we’re all much less grateful than we should be. So spend a moment remembering God’s goodness. What do you have to be grateful for. And sit there, and feel it, and thank him for it.