The Parable of the Shrewd Manager

Luke 16:1-8:
Jesus told his disciples: “There was a rich man whose manager was accused of wasting his possessions. ² 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.’
³ “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— ⁴ I know what I’ll do so that, when I lose my job here, people will welcome me into their houses.’
 ⁵ “So he called in each one of his master’s debtors. He asked the first, ‘How much do you owe my master?’
 ⁶ “‘Nine hundred gallons^[a] of olive oil,’ he replied.
“The manager told him, ‘Take your bill, sit down quickly, and make it four hundred and fifty.’
 ⁷ “Then he asked the second, ‘And how much do you owe?’
“‘A thousand bushels^[b] of wheat,’ he replied.
“He told him, ‘Take your bill and make it eight hundred.’
 ⁸ “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.

If we understand the parable's social setting, we'll see that his actions are not dishonest, just shrewd. By shrewd, I mean calculated to insure one's own self-interest. I think this parable disrupts our usual definition of what acting in our own self-interest means in light of the reversal of fortunes the kingdom of God will bring.
In ancient Palestine, there was a complex social, economic relationship among landowners, stewards, peasants, and merchants. The wealthy landowners sought to get as much profit as possible from their holdings and tenants. The steward was the middleman between the landholder and the merchants and tenants in the exchange of goods and services such as buying and selling grain, oil, and crops and collecting rents. If he was able to get an additional take for himself in these transactions, the master didn't mind; in fact he expected it. As long as the master's profits kept rolling in and the steward did not get too conspicuous in his consumption, the master was fine with the steward's benefiting from each deal. As for the merchants and tenants, they were in a relatively powerless position, unable to directly confront the master. Their target, when they were disgruntled or felt put upon, was the steward, the master's retainer.
The steward's position in this complex social network was both privileged and vulnerable. He had a relatively high standard of living, a benefit of his being able to read and write and his training by the master, but he was completely dependent on the goodwill of the master. He himself states it in verse 3. "What will I do now that my master is taking the position away from me? I am not strong enough to dig, and I am ashamed to beg." We might assume that he is whining here, selfishly unwilling to engage in honest labor. He is actually just stating the fact that he is not prepared by physical training or by the habit of hardship to compete with the peasant labor pool for the hardest, most menial of jobs: digging. His strength gone, he would be reduced to begging, and, in short order, would die because of the malnutrition and disease that came with poverty. His situation is dire. Something must be done to prevent this future. No one can do it but him.
While there is desperation in the steward's action, there is also premeditated, self-interested shrewdness. He calls the debtors in one by one, not giving them the chance to compare notes and collaborate against him ahead of time. He knows that his reduction of what they owe will not ensure their permanent goodwill and hospitality toward him. At best it may postpone his poverty for a short time as they invite him to a couple of meals. He may be hoping that the master cannot blame him for not extracting the interest, since to do so would be an admission that his steward, with his blessing, had been condoning charging interest, in violation of the Torah. He may be hoping his actions could make it possible for him to secure another position as a steward for another member of the landowning elite, thereby saving him from a life of hard labor.
While there is desperation in the steward's action, there is also premeditated, self-interested shrewdness. He calls the debtors in one by one, not giving them the chance to compare notes and collaborate against him ahead of time. He knows that his reduction of what they owe will not ensure their permanent goodwill and hospitality toward him. At best it may postpone his poverty for a short time as they invite him to a couple of meals. He may be hoping that the master cannot blame him for not extracting the interest, since to do so would be an admission that his steward, with his blessing, had been condoning charging interest, in violation of the Torah. He may be hoping his actions could make it possible for him to secure another position as a steward for another member of the landowning elite, thereby saving him from a life of hard labor.