Luke 16's story of the shrewd manager follows several parables in the previous chapter. And I think they all relate.
The Pharisees and teachers of the law have just complained that Jesus hangs out with sinners and tax collectors. So Jesus tells them the parables of the lost coin, the lost sheep, and the prodigal son to communicate why he spends time with these sort of people. They are the lost, needy, and sick. They are those who are seeking answers. And when one repents, Heaven rejoices.
The story of the prodigal son brings in the Pharisees. They are like the older brother who didn't care about God's forgiveness or saving lost souls. They were more concerned about what God owed them. "Look! All these years I’ve been slaving for you and never disobeyed your orders. Yet you never gave me even a young goat so I could celebrate with my friends. But when this son of yours who has squandered your property with prostitutes comes home, you kill the fattened calf for him!" (Luke 15:29-30 NIV).
See, the Pharisees had developed this system of acquiring goods from God: if they obeyed all these laws, then God owed them a prosperous life. In fact, a prosperous life became a sign that God approved of them.
We see that clearly in the older brother's complaint. The real point of his working so hard was to gain everything the prodigal got through repenting. But as Jesus said to them in Luke 16:13, they couldn't serve God and money. Either their end goal was prosperity or their end goal was God.
Jesus was jerking the rug out from under the Pharisees and teachers of the law by showing them that they were merely looking for a way to justify their right to a prosperous life, their right to the pursuit happiness.
The parable of the shrewd manager stands in contrast to the prodigal son story. It's like Jesus turns to his disciples after the story of the prodigal and tells them, "Don't be like the Pharisees. Don't be like the prodigal's older brother. Instead be like this shrewd manager."
In this parable a wealthy man accuses his manager of wasting his possession and calls him in to answer for himself. Before turning over his position, the manager forgives his boss' debtors so that he will have friends after he's fired.
I think Jesus is saying: your time, O Pharisees/Israelites/teachers-of-the-law, on this earth will soon be up, and you'll have to answer for what you've done, your mismanagement of God's things, the poor handling of God's laws and God's people. Therefore, use the Lord's riches—that is, his mercy and forgiveness and withholding of judgement—to forgive the sins of these tax collectors and sinners who don't owe you anything anyway. Do this, so that when you die, you may live peaceably in God's kingdom side by side with them.
It's the invitation of the prodigal's father all over again: "My son, you are always with me, and everything I have is yours. But we had to celebrate and be glad, because this brother of yours was dead and is alive again; he was lost and is found." (Luke 15:31-32 NIV)
Everything the father had was the older brother's already. The shrewd manager had command over his master's money. They were already in a position to receive wealth and pass it on to those in need. I'm not talking about financial wealth here. We're talking about God's wealth. Our money and homes and freedoms and friendships may all be taken from us, but that doesn't mean we've run out of things to give others. We will never run out of God's mercy, love, and forgiveness. We can freely pass that out to those we've previously designate as sinners. We can do this so long as we recognize how much God has already given to us.
It's impossible to do this though—recognize how much grace God has given us—as long as we're making up our own code of conduct and following it rather well. That's what the Pharisees and teachers of the law were doing. They had decided it was okay to divorce for these reasons but not those. Jesus makes mention of how the Pharisees weren't properly using God's standards for divorce in Luke 16:18.
The Pharisees had also decided no one ought to do x, y, and z on the Sabbath. They'd decided you had to stay away from anyone who was sick, and quarantine a certain number of days if you came in contact with unclean people. They'd defined goodness for themselves so that they had the power to say that they themselves were good and thus deserved God's approval and blessings.
Jesus tells them, “You are the ones who justify yourselves in the eyes of others, but God knows your hearts. What people value highly is detestable in God’s sight." (Luke 16:15 NIV)
And what do people value highly? What did the Pharisees value highly? What did the prodigal's brother value highly? Their own work. Their own efforts. Their own striving to prove to God, the world and themselves that they could do what God required.
It's the story of Cain and Abel all over again. God wanted the sacrifice of a pure lamb, but Cain was convinced that God must want the fruit of his own labor.
Be shrewd on this earth lest sin overpower you and convince you that you are responsible for earning God's blessings. We can never earn it. What God wants is perfection—every "stroke of a letter of the Law" to be fulfilled in a person (Luke 16:17 NASB). And none of us can give that to God. Only Christ could and did. He alone fulfilled every minute detail of the law for which God asked.
Therefore, forgive others their debts. Forgive them for the way they haven't followed what you think is right. Forgive them when they apologize and forgive them when they don't. Be shrewd in dealing with other's sins towards you. They aren't robbing you of your just dues anyways; they rob God.
And if they take your coat or demand you walk a mile, go another mile. Coats and legs are gifts from God. What is eternal, no one can take from you.
The alternative to this is the dire story about a rich man and Lazarus found in the rest of Chapter 16.
More on parables: Equal Pay, Our Talents, Throwing Trees in the Ocean, Put on the Fancy Smancy Clothes,
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