The Story of the Dishonest Manager: Luke 16
Beginning with Luke 15, Jesus uses four parables to explain his shocking orientation toward the traitors, criminals, and other outcasts. He identifies with (and invites all of us, including the scribes and pharisees, to join in this identification with) a shepherd who leaves the 99 for the 1, a woman who searches for the precious coin, a betrayed father who welcomes the horrible son, and a fired dishonest manager who makes friends of debtors.
In Luke 15-16, the scribes and the Pharisees, like so many other religious leaders in Christianity, Islam, and other religions, are seen as protective separationists. They are primarily concerned with protecting the borders, keeping the community of faith pure from contamination. They are focused on the purity of the institution and of the faith, and they feel strongly that this is the best way to serve God and to properly respect and honor God's word.
From the point of view of Jesus, the scribes and Pharisees want to keep the riches of the Torah for themselves, separating themsevles from the outcast. He recognizes that they think that they're best serving God by excluding the outcast, the gentile, etc. But he rejects their institutional borders around the community of Torah, just as he rejects how the Saduccees and priests enforce institutional borders around the Temple. Elsewhere, Jesus savagely criticises the Saduccees and priests for twisting the Temple from a house of prayer for all the nations into a private club for the Jewish elite -- they turned it into a den of theives. And here, he savagely criticises the Pharisees and priests for separating themselves from the very ones they should seek an eternal relationship.
Rather than protecting institutional purity by excluding people (analogous to protecting the bottom line for the rich man), Jesus welcomes the impure. Like the father who annoys the older son by throwing a party for the ne'er do well horrible son or the dishonest manager who annoys the rich man by cancelling the debts of his future friends, so Jesus makes friends of traitors, criminals, and other outcasts. Jesus identifies with the dishonest manager. Jesus isn't doing what the scribes and pharisees want him to do. Their focus is on protecting the business (the institution of synagogue and Torah). But he squanders their wealth by forgiving the debtors, spending everything on making eternal friends of the debtors. In the end, he even squanders his own life.
Jesus is focused on building friendships and relationships with the debtors. And he encourages us to do the same. The stories of the lost sheep, lost coin, and prodigal son are not really about the lost sheep, lost coin, and prodigal son. They are rather about a searching shepherd, a searching woman, and a searching father. Likewise, the 4th story is about a man searching for friends that will survive his soured relationship with his employer. All 4 stories are about a desperate searcher, which explains why Jesus welcomes tax collectors and sinners and eats with them.
A subtext in these is this: Faithful wealth is the stuff we take with us into the kingdom: justice, grace, love, relationships, faith, character, righteousness. "Dishonest wealth" isn't so much ill-gotten gain as it is the stuff that has no real, lasting value. The spiritual life is largely
(1) a discovery of the true value of the former, and our transformation around those things, and
(2) a discovery of the false ("dishonest") value of the latter, and our liberation from slavery to them.
Dishonest wealth includes everything we put our trust in that turns out not to be trustworthy: our institutions, our false idols, our prejudices, our money. None of these will go into the Kingdom -- and if we cling too tightly to them, neither will we.
A side note:
One will observe that when Luke sets the scene for the first 3 stories (the stories of a searching shepherd, a searching woman, and a searching father), it appears that Jesus is telling the stories to the scribes and pharisees. But is appears that the story about the searching ex-manager is told to the disciples (16:1).
Perhaps that is because this particular story is the most radical of the 4. Perhaps it is the most damning to the scribes and Pharisees. After all, there is no one evidencing their twisted attitude in the first 2 stories, and in the 3rd, the older brother is definitely a brother, is clearly loved by the father, and his point of view is both normal and sympathetic to any reasonable listener. But in the 4th story, it is clear that the rich man and his searching ex-manager are in an adversarial relationship. The rich man's assessment that his searching ex-manager is cunning ("shrewd") does not imply acceptance, approval, or positive feelings of any sort. He grudging admits that his searching ex-manager has out-foxed him at his expense. Perhaps Jesus tells this story to the disciples, not the scribes and Pharisees, because he does not want to create an even deeper wedge. After all, he invites them into relationship too.
But one cannot say with certainty from the text whether the scribes and Pharisees are present or absent, nor can we say from the text that he's withdrawn from public and is whispering in private to his disciples. Perhaps it's like a children's sermon: Many adults suspect that while the children's homilist speaks directly to the children, the homilist's intention is for the adults to hear it in a deeper, clearer way than the children. Perhaps Jesus turns and speaks to his disciples, with the scribes and pharisees both within earshot and within his peripheral vision.
Moreover, one can't tell from the text whether this is "disciples" in the narrow sense, the close band, or in the broader sense, all those who show up in crowds to listen.
The Lord be with you.