It's an evidence of just how hard a time we have with this parable that your Bible very likely inserts a heading before it, along the lines of "The Parable of the Shrewd Manager," or some such thing.
"Shrewd" is more tactful than "Dishonest" (or "Lying, Cheating, Deceitful"); we feel compelled to soften the adjective, since, after all, there's supposed to be something admirable in this figure. After all, the Lord commends him for his behavior, doesn't He?
Well...no, not precisely.
The problem is this: starting with The Rule Notably Never Laid Down By Anybody, i.e., that every parable is an allegory and the key is to find out who's God and who's Jesus and who's the Christian in the parable, and then take it from there—starting from that spurious Rule (no matter how blatantly the biblical text telegraphs otherwise), we get ourselves all in a dither trying to figure out how "God" (though Jesus rather explicitly tells us the boss ISN'T God) could approve of such a lying, deceitful "Christian" (though Jesus rather explicitly tells us the crooked manager ISN'T a "Christian").
Hence the "creativity," the impressive mental contortions, the convoluted warren of ratiocination making out how this pair of crooks could possibly be God and the Christian.
We blithely overlook the screaming fact that Jesus sometimes adduced a parable (which is any kind of comparison, analogy, illustration or, take note, contrast, in story form) in order to depict what God is not like, or to juxtapose the way the world acts with the way God acts. Sometimes God and His children only come into the picture after the parable, by way of the Lord's saying, in effect, "Now, contrary to the folks in that picture, here's how it works for you...."
The parable of the corrupt judge, for example. The corrupt judge isn't God; he's a corrupt judge, a bad guy. And the point of the parable is certainly not to say "God's just like that. [Wait, what?!] So, keep pleading and wheedling because, even though He couldn't care less about you, He will finally give in if only to get you out of His hair, just like the judge who symbolizes Him."
Um-m-m-m-m.....................
No.
Nonsense.
The whole reason for pronouncing the parable at all is to convey, adamantly, that God is not that judge and nothing like that judge. And that, if even a thorough creep like the judge will, in spite of himself, render good, for no better reason than getting some peace and quiet, then...
"HOW MUCH MORE"...
...will your loving Heavenly Father give you what you need?
The "How Much More?" principle is key to a number of the Lord's contrastive parables/illustrations.
Same thing with the man who hated being bothered at midnight. Just to get rid of the annoying neighbor, he gave him the loaves of bread for the unexpected guests. Jesus makes it clear that He is adducing a contrast. God is not the man who wishes you'd just go away and only tosses you a few loaves so he can close the shutters and get back to sleep. God is infinitely more loving and attentive than that.
"If you, being evil, know how to give good gifts to your children, HOW MUCH MORE will your heavenly Father...?"
Now, as for the story of the crooked manager....
The crooked manager is just a crooked manager, scheming, deceitful, remarkably resourceful. The manager learns his boss is on to him, so he takes extraordinary (and, in keeping with his character, deceitful) means to guarantee a soft landing when he gets booted off the estate. I sense that this deviously finagled guarantee implicitly entails blackmail, because if the debtors, afterwards, fail to set this guy up in a cushy post somewhere, he's got the goods on them, i.e., that they colluded with him to deceive his old boss.
But the employer somehow gets wind of the whole scheme and, surprisingly, rather than being infuriated, he shakes his head, with a wry chortle and a grin, and (in my 21st century paraphrase) says, "Why, you-u-u-u sneaky little rat! And here I thought I was a clever so-and-so. Hmm, I may just keep you on (besides, now I've also got something on my debtors that I can use against them, and something on you!). You could be valuable, as long as I keep you on a tight leash...."
As the saying goes, there is honor among thieves....
And the Lord's application/extrapolation of the story underlines that very notion, the "birds of a feather" notion.
Yes, in fact, the birds-of-a-feather notion and the how-much-more? notion are both at work in this parable and its immediate application.
Who are the employer and the crooked manager? They are the children of darkness, the children of this world; they are birds of a feather; they stand on the opposite side of the ledger from the children of light:
"For the children of the world are wiser in their own generation than are the children of light."
That "For" (i.e., "Because") pops up jarringly. It seems to smack you in the face without warning. Even more if we translate the Greek with the less poetic "Because." We have abruptly exited the world of the story, and Christ is summing up its significance for His hearers.
It's not the boss telling the manager "Because...."
It's the Lord telling His followers, "They acted like that because that's how the children of the world act." It's Jesus telling His flock, "I told you this story because I want you to see how quick-witted, efficient and resourceful the children of darkness are in dealing with their own kind and scrambling after their wretched aspirations. The children of the light, by comparison, have a tendency to be hopelessly naive, inefficient, unfocused and timid."
The "For..." telegraphs that this is why Jesus told the parable. That is the explanation.
The children of the world, like this employer and manager, can even appreciate the joke in getting ripped off by each other, since they share the same basic motivations: "I was going to get you, but you got me first, you rascal!"
The appalling tragedy of it is, all that efficiency and resourcefulness is finally for nothing, goes up in smoke on the altar of ephemeral, illusory acquisition and status.
While the children of the Kingdom, the children of the light, ought for their part to be infinitely more determined, and devoted, and single-minded, in pursuit of the never-passing Kingdom riches—by Kingdom means, of course, which excludes the sort of fraud practiced by the manager in the parable.
The clear sense of the "tag-line" is that the children of the light too often fail to compare to the children of the world for determination and single-minded resourcefulness.
Understanding the parable (accurately) as contrastive, rather than robotically allegorical (again, the famous Rule Nobody Ever Gave Us), goes on to make sense out of the continuing discourse, in a way that an (inaccurate) allegorical reading of the parable simply does not.
After Jesus sums up the character of the parable figures, He underlines the contrast by addressing the other side of the ledger:
"I tell you (His disciples, the children of light, namely, not the children of the world), use the mammon of unrighteousness to make friends for yourselves, so that, when it is gone, they will welcome you into eternal dwellings."
Jesus is not urging the disciples, of course, to be as dishonest as the manager in the story, but rather to make the most of everything they have in the world for the sake of everything they have in the Kingdom of God.
By the way, like it or not, believer or non-believer, we are all trading daily in the currency of "unrighteous mammon," i.e., the money and means of a fallen and intrinsically unrighteous world. Unlike the children of the world, however, we have "the light"—the vision, the understanding—to devote all we possess (which is passing away—"You can't take it with you") to the service of God and His Kingdom (which is not passing away—"You can take it with you").
And, when you finally have nothing—as nothing you will surely have ("Naked I came into the world; naked I will leave it")—you will be received into the everlasting homes of the friends you expended your insubstantial worldly resources to win for the Kingdom.
