Summary: The parable of the dishonest steward is perhaps the most uncomfortable one to preach on. But, there may be more there to learn than we had previously thought.
A man took his seat in the theater, but he was too far from the stage. He whispered to the usher, "This play is a mystery, and I like this type of play so much I really watching them close up so I can catch all of the dialogue. If you’ll get me a better seat I’ll give you a handsome tip."
So, the usher moved him into the second row, and the man quietly handed him with a quarter.
The usher looks at his tip for a second… and then leaned over and whispered in the man’s ear: "The wife did it."
APPLY: There’s something about that joke that makes us say: “alright.” The usher may have been ripped off but he got his revenge in a cunning, clever… one might even say shrewd way.
I. We live in a world that often understands and appreciates shrewdness and cunning in others. In fact, many movies and plays have clever plot twists where their heroes or heroines do some shrewd thing to thwart evil – and the audience applauds. Shrewdness is considered a valuable skill.
But here in Luke 16 (quickview)  we have a parable where Jesus tells us about a shrewd manager… and something inside of us seems to rebel. How can we be enthralled by a cunning, dishonest manager who basically rips off his employer AND THEN (as Jesus tells us) ends up being commended for his actions?
The story starts out with a steward mismanaging his master’s money. AND when it becomes obvious he’s going to lose his job, he cheats his employer even further by collecting outstanding debts of others… BUT only partially.
One man owes 800 gallons of olive oil. The dishonest manager tells the debtor to reduce his bill to 400 gallons. And then I suspect he quietly told the man "Make sure you remember who did this for you.”
Another man owes 1000 bushels of wheat and the steward has him reduce the bill to 800. Once again you can sense the reminder "Make sure you remember who did this for you."
He does all this to make friends so that when he loses his job, he’ll have a place to live when he gets fired by his present master.
Most preachers (including me) would rather NOT preach this text. In fact, it makes many people so uncomfortable, that they try to rework the story.
1. One commentator I read suggested that the master had been dishonest – and that this manager was simply behaving like his employer. That was somehow supposed to excuse this man’s behavior.
2. Others whom I read implied that the story of the dishonest steward was simply Jesus’ way of saying: even a bad man can be a good example. (In this case, an example of what not to do!)
II. But, I think there’s a 3rd possibility here. I believe when Jesus told the story of the dishonest steward he had somebody special in mind. At the end of His story we see that Jesus has hit his mark. “The Pharisees, who loved money, heard all this and were sneering at Jesus.” (Luke 16:14 (quickview) ).
Why were the Pharisees sneering? Jesus said it was because they "loved money."
I believe initially the Pharisees would have loved this story. This "dishonest manager" was their kind of man - a survivalist. He was the type of man who would do whatever was necessary to survive, to get ahead.