In all my decades of church going, I’ve never heard a pastor or priest preach on this parable. There are reasons for this: it doesn’t provide the Hallmark feels that parables like the Prodigal Son do; pastors can be lazy, and organizing a sermon with this material requires some work to brush away some assumptions; it comes off as anti-Semitic to many people, and pastors are cowardly when it comes to that. I’ll note here that Jesus could be considered one of the most “anti-Semitic” religious leaders in history. It’s a small logical leap in our current intellectual climate to establish “Pharisee”—a group of folks He often spoke to and about—as a dog whistle synonym for “Jew.”
He also said to the disciples, “There was a rich man who had a manager, and charges were brought to him that this man was wasting his possessions. And he called him and said to him, ‘What is this that I hear about you? Turn in the account of your management, for you can no longer be manager.’ And the manager said to himself, ‘What shall I do, since my master is taking the management 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 removed from management, people may receive me into their houses.’ So, summoning his master’s debtors one by one, he said to the first, ‘How much do you owe my master?’ He said, ‘A hundred measures of oil.’ He said to him, ‘Take your bill, and sit down quickly and write fifty.’ Then he said to another, ‘And how much do you owe?’ He said, ‘A hundred measures of wheat.’ He said to him, ‘Take your bill, and write eighty.’ The master commended the dishonest manager for his shrewdness. For the sons of this world are more shrewd in dealing with their own generation than the sons of light. And I tell you, make friends for yourselves by means of unrighteous wealth, so that when it fails they may receive you into the eternal dwellings.
As much as we’d want Jesus to make sure the manager got his comeuppance for cheating his master, that wasn’t the point of the parable. Rather clearly, He said that using any wealth to create social bonds is a good idea—even if that wealth is ill-gotten gain. Jesus even pointed out that they weren’t great folks to begin with: the master was so enamored with his ex-employee’s craftiness that it overshadowed his disgracefulness.
To bring in context from the previous chapter, He was traveling and people were gathering to hear Him talk, so although He was directly addressing His disciples there were others listening in. Later on in this particular chapter, Luke noted a reaction from some Pharisees in the crowd. So there’s the possibility that Jesus was indirectly addressing those folks. This, in itself, is rather shrewd. I’d like to think most of the audience would snicker a bit, or even get a little squirmy, from this sly rhetorical maneuver, like when we might talk about a powerful but pompous fellow to a friend while the blowhard is sitting right next to us.
I like was Ed has to say, from his commentary on the Gospels (PDF):
It was a common teaching among Pharisees that the true mark of God’s favor was material wealth. Naturally, they scoffed at Jesus’ teaching, rejecting His assertion they didn’t serve the Lord. They had a long list of memorized speeches about how this was all according to the Law of Moses. The logic was impeccable, but morally empty. God knew their hearts, which is what really mattered to Him, a factor of humanity they casually ignored. They had their chance. From the day of Moses until John the Baptist came along, it was their opportunity to find the path to the truth, to absorb the higher meanings of the Law and see it pointing to the spiritual side of things. Not only did they miss it; they also got farther and farther away. Their time was past. Now the Son has come, and He is teaching the Way of the Kingdom of God. All the people they had rejected as unworthy were crowding around Jesus, trying to find out how to become a part of this spiritual Kingdom.