When Shrewdness is Rewarded

Sermon 406 St. Martin’s 160 (Riverway) 9/21/25

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. 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.' 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. I have decided what to do so that, when I am dismissed as manager, people may welcome me into their homes.' So, summoning his master's debtors one by one, he asked the first, `How much do you owe my master?' He answered, `A hundred jugs of olive oil.' He said to him, `Take your bill, sit down quickly, and make it fifty.' 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.' 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. And I tell you, make friends for yourselves by means of dishonest wealth so that when it is gone, they may welcome you into the eternal homes.

"Whoever is faithful in a very little is faithful also in much; and whoever is dishonest in a very little is dishonest also in much. If then you have not been faithful with the dishonest wealth, who will entrust to you the true riches? And if you have not been faithful with what belongs to another, who will give you what is your own? No slave can serve two masters; for a slave will either hate the one and love the other, or be devoted to the one and despise the other. You cannot serve God and wealth."

Luke 16:1-13

The White Sox Game The summer after my sophomore year in college, I took a road trip out west by myself. I packed up my dorm room in about 15 minutes into one suitcase and two boxes, and put it in the bed of my truck, and then hit the road.  

I started early in the morning, with the goal of reaching Toledo by nightfall. By the afternoon, I was making great time and was nearing Toledo earlier than I expected. I then realized my favorite baseball team was playing in Chicago that night. I was still four hours away, but I thought I could make it just in time for the first pitch. So, I booked for the South Side of Chicago.

As I got off the exit, nearing the White Sox ballpark, I was frantically looking for a parking space. The game was about to start in five minutes. Right then, a nice gentleman waved me over to this perfect spot on the street that no one had gotten to yet.

I asked him how much it was, and with a friendly smile on his face, he said, “Just $30.” That was a deal because of how close it was to the stadium. I was ecstatic. I had made it just in time and found the perfect spot.

After giving the nice man his money, I was looking for something in the back of my truck and was telling him how I had driven all the way from Boston that day. I thought he would be impressed, and was waiting for his reply, but when I turned around, he was gone. In fact, I could see him running down the street in a full sprint.

I then looked up to see a sign in bold letters saying “No Gameday Parking.” All the spaces around me were empty for a reason. And come to think of it, the guy who waved me down didn’t have a flag or vest of any sort, actually, he wasn’t wearing a shirt at all!

Yes, this picture is from that infamous day.

I thought about it some more. I was decked out in Red Sox gear, my truck was red, and it had a huge Red Sox sticker on the back. I might as well have had “Sucker” written on my forehead as I was driving through the streets of Chicago.

I learned a valuable lesson that day: Don’t be so naïve.

Jesus famously said, “Be as wise [or as shrewd] as serpents and as innocent as doves.”[i] The snake in the Garden of Eden is described as being crafty and shrewd as well. In that tale, he uses his wit to manipulate and deceive humanity away from the good purposes of God.

Why would Jesus then tell us to be as shrewd as the deceiver? Isn’t that antithetical to sheep who are supposed to follow the Good Shepherd?

The same question can be asked about the parable we heard this morning. What is Jesus actually commending—and even recommending—in this very strange story? Is Jesus giving us a free pass to be dishonest in our business dealings as long as we outwit others? Should we all be outside of the Astros’ stadium trying to scam every out-of-towner that comes our way?

I think there is more going on here, and for the rest of our time, I'd like us to delve into this story to see what Jesus is really trying to tell us.

Luke 16 To set the scene, it is important to note that this parable immediately follows the story of the Prodigal Son. Some even consider our parable as an appendix to the Prodigal Son.

Just as there is a wayward son, there is a wayward manager. Both act recklessly, wasting the wealth of another until it leads to their own ruin, which raises the climactic question of how they will be received by the one whose trust they have broken.

Our parable is in conversation with the one that preceded it, and if we recall the gracious and forgiving nature of the Prodigal Son’s father, then we shouldn’t be shocked by the reaction of the manager’s boss at the end of our parable.

In the first story, we discover a valuable lesson about the unrelenting love of the Father. In the second, we learn how we are to act as his children in this world. You really need both parables to understand Jesus’ larger point.

And so, let’s look at the first couple of verses:

Jesus told his disciples: “There was a rich man whose manager was accused of wasting his possessions. 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.’

Word has gotten back to a rich man that the steward of his estate—a man whom he has given an immense amount of power and trust— has been utterly wasting it all. He calls in the reckless manager and fires him on the spot.

The manager was not only losing his job, but likely losing his home, which would’ve been on the master’s estate. In the blink of an eye, this man is now in a real pickle: he is jobless and homeless.

It’s unclear if this man helped manage a large farm or was more of a banker's agent for the rich man, but part of the demand to “give an account,” as our passage says, meant that he needed to hand over the account books. 

Usually, there would be days of negotiations before he was officially let go, but this time, the manager doesn’t push back; he has been caught red-handed and is silent. He heads off to collect the account books and return them to his master.

As he walks away, his survival instincts kick in. Because of his dire situation, he’s got to think of something fast.

“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— I know what I’ll do so that, when I lose my job here, people will welcome me into their houses.’

Thankfully for the man, his firing was done in private. Only he and the master know his situation, and luckily for him, he still has the account books in his possession. Everything the manager does from this point onward is illegal; he does not represent his master, but the people he negotiates with are unaware of this crucial change.  

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

“‘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.’

Parable of the Unjust Steward by A.N. Mironov

One by one, he meets with those who owe his master a portion of their crop—and in great haste—he begins slashing their debts. Nine hundred gallons of olive oil would’ve fetched 500 denarii—a year and a half’s wages. That’s not a small discount.

He does the same with others and ensures that they write it down with their own handwriting in the book; this is a legal transaction, and he has their signature to prove it.

Each time he does this, the people walk around with a huge smile on their faces, and word begins to spread around town. Just think about it: Have you ever been forgiven a debt? At the very least, have you ever dreamed of a debt being cut in half in an instant?

Financial debts can weigh on us; they are a burden that we carry, and they not only shape how we live our lives in the present, but they also shape whether we have a positive or negative view of the future.

The shrewd manager in this instance is the bearer of unexpected—and in some ways life-changing— good news. He gains favor from everyone simply by being the master’s evangelist and by showing everyone just how gracious the master is.

As one after another’s debt is significantly reduced, it almost feels like the Year of Jubilee, and the town can’t help but sing the praises of the generous master.

The master’s approval rating is through the roof because of what his former manager has done. It may not have been the ethically right thing to do, but it was certainly clever.

The Master’s Response When the manager finally returns and hands him the account books, what is the master's reaction supposed to be? He could be angry and tell everyone that it was all a lie and they still owed him everything as before—which would’ve made them bitter and angry against him for his perceived greed.

Or he could ride the wave of admiration with no one the wiser as to whose idea it really was. And so,  

“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.”

His earlier conduct is still condemned because the master doesn’t rehire him on the spot, but he does praise him for his confidence in the master’s gracious nature. The manager knew that his master was a good and generous man. Just like the Prodigal Son, this manager believed that he would be dealt with graciously when he returned to the master, and his gut feeling was right.

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Does this parable encourage us to keep sinning because we know we will be forgiven? Can we take advantage of God’s good graces as the manager took advantage of his master’s?

The Apostle Paul resolutely says, “By no means!” Because we have been linked to Christ through our baptism and share in his death, so that “just as Christ was raised from the dead through the glory of the Father, we too may live a new life.”[ii] We are to live a new life in this old world.     

So what’s the lesson?

We know that Jesus doesn’t want us to mimic the dishonesty of the manager because he lumps him in with “the people of this world” at the end of this parable.

But the point is clear: the people of this age are so good at securing their future for themselves through their shrewdness that the children of the light should also be wise and resourceful in their relationship with God and one another.

Another way of saying it: don’t be so naïve! Compared to the actions of the dishonest manager, how much more so should we—as people buried and raised to new life in Christ—commit ourselves to God’s kingdom as if our life depended on it, trusting the gracious nature of our Lord.

We should have the same urgency in our actions, use every bit of our intellect, skill, and yes, relationship capital, for the glory of God.

The people of this age will do whatever it takes for quick returns and large profits, while the children of light have invested in something far more secure, even if it’s just behind the veil of this mortal life.    

As Jesus said, “Do not store up for yourselves treasures on earth, where moths and vermin destroy, and where thieves break in and steal. But store up for yourselves treasures in heaven…For where your treasure is, there your heart will be also.”

The shrewd manager represents us at our best and our worst. We can use our skills for our own betterment or to reflect the generosity of our Lord. We can share the amazing news of God’s generosity with others and see how it changes lives…or we can selfishly hold it to ourselves as if it were only intended for us.

We can come before the throne of God either in fear of his righteous judgment, knowing that we should be condemned for our sin and deceit in this life, or in humility and faith, we come before our Heavenly Father in the sure confidence of his mercy and forgiveness, because of Jesus Christ, who is our only mediator and advocate.

You are a child of the light. Your debt has not been cut in half; it has been completely wiped clean.

You are a child of the light. It may be hard to live as one in this present evil age; nevertheless, you are called to bear the true light that enlightens all things, no matter how dark things get in this sinful and broken world.

You are a child of the light.

You are a city on a hill.

And so, “Let your light shine before others, that they may see your good deeds and glorify your Father in heaven.”[iii]

[i] Matthew 10:16

[ii] Romans 6

[iii] Matthew 5:16

Much of the cultural background came from Jesus Through Middle Eastern Eyes.