Prominent Theologians' answer to: What is "The Parable of the Shrewd Manager" about? The Parable of the Shrewd Manager (full text below) is perhaps one of the hardest parables to interpret. At first glance it seems to be about rewarding dishonesty!
What lesson is Jesus teaching His followers with this parable? Has any prominent theologian (eg Matthew Henry, NT Wright) explained this parable?

Luke 16:1-14
Jesus told his disciples: “There was a rich man whose manager was accused of wasting his possessions. So he called him in and asked him, ‘What is this I hear about you? Give an account of your management, because you cannot be manager any longer.’
“The manager said to himself, ‘What shall I do now? My master is taking away my job. I’m not strong enough to dig, and I’m ashamed to beg. I know what I’ll do so that, when I lose my job here, people will welcome me into their houses.’
“So he called in each one of his master’s debtors. He asked the first, ‘How much do you owe my master?’
“‘Nine hundred gallons of olive oil,’ he replied.
“The manager told him, ‘Take your bill, sit down quickly, and make it four hundred and fifty.’
“Then he asked the second, ‘And how much do you owe?’
“‘A thousand bushels of wheat,’ he replied.
“He told him, ‘Take your bill and make it eight hundred.’
“The master commended the dishonest manager because he had acted shrewdly. For the people of this world are more shrewd in dealing with their own kind than are the people of the light. I tell you, use worldly wealth to gain friends for yourselves, so that when it is gone, you will be welcomed into eternal dwellings.
“Whoever can be trusted with very little can also be trusted with much, and whoever is dishonest with very little will also be dishonest with much. So if you have not been trustworthy in handling worldly wealth, who will trust you with true riches? And if you have not been trustworthy with someone else’s property, who will give you property of your own?
“No one can serve two masters. Either you will hate the one and love the other, or you will be devoted to the one and despise the other. You cannot serve both God and money.”
The Pharisees, who loved money, heard all this and were sneering at Jesus.
From Mathew Henry's Concise Commentary:

Whatever we have, the property of it is God's; we have only the use of it, according to the direction of our great Lord, and for his honour. This steward wasted his lord's goods. And we are all liable to the same charge; we have not made due improvement of what God has trusted us with. The steward cannot deny it; he must make up his accounts, and be gone.
This may teach us that death will come, and deprive us of the opportunities we now have. The steward will make friends of his lord's debtors or tenants, by striking off a considerable part of their debt to his lord. The lord referred to in this parable commended not the fraud, but the policy of the steward. In that respect alone is it so noticed. Worldly men, in the choice of their object, are foolish; but in their activity, and perseverance, they are often wiser than believers.
The unjust steward is not set before us as an example in cheating his master, or to justify any dishonesty, but to point out the careful ways of worldly men. It would be well if the children of light would learn wisdom from the men of the world, and would as earnestly pursue their better object.
The true riches signify spiritual blessings; and if a man spends upon himself, or hoards up what God has trusted to him, as to outward things, what evidence can he have, that he is an heir of God through Christ? The riches of this world are deceitful and uncertain. Let us be convinced that those are truly rich, and very rich, who are rich in faith, and rich toward God, rich in Christ, in the promises; let us then lay up our treasure in heaven, and expect our portion from thence.

My understanding from this commentary is that the manager's goal didn't change - he wanted a comfortable lifestyle without working too hard - and used his Master's resources for his own purposes. Even when he was caught - and was about to lose the position that enabled him to achieve his nefarious goal easily, he made another plan, a very clever plan, and tried to win the affections of his master's debtors by slashing their debts - probably guaranteeing that someone would give him free board and lodging for a while.
Jesus is certainly not holding this man up as a shining example of morality, but of using his brains to try every possible method of achieving his aim. The aim was not noble, but his persistence and shrewdness in pursuing the aim was. What should we take from this then? We should learn from anyone - even those we want to label as &quot;worldly&quot; or &quot;sinful&quot; - to work hard and be shrewd in how we pursue God's aims.
The other aspect of this parable is using the stuff of this world for eternal purposes - In the first fraudulent scheme the manager was simply skimming the master's funds and putting them in his own pocket. His thinking was entirely in the pleasures of the here and now. Once he saw his cushy position coming to an end he started using the money to make friends to provide for him at the end of his present &quot;life&quot; when he no longer had any control.