Luke 16:1-13. One of Jesus' most puzzling parables. A rich man discovers his estate manager has been wasting his possessions and demands an accounting — essentially firing him. The steward, knowing he is about to be unemployed, goes to his master's debtors and unilaterally reduces their debts: 100 measures of oil becomes 50; 100 measures of wheat becomes 80. His goal is to make friends among the debtors so that when he is fired they will welcome him into their homes. When the master finds out, astonishingly, he "commended the dishonest manager for his shrewdness" (v. 8). Jesus' application: "For the sons of this world are more shrewd in dealing with their own generation than the sons of light."
The Unjust Steward parable has generated more interpretive sweat than any other. Key question: how can Jesus commend dishonest behavior? Several interpretive keys. (1) The master commends the shrewdness, not the dishonesty. The steward's moral fraud is not praised; his wit and decisive action in a crisis is. Jesus is making a single-point comparison: if a worldly man can be so clever in securing his earthly future, Christians should be at least as clever in securing their eternal future. (2) Make friends by means of unrighteous wealth (v. 9) is Jesus' command: use your money — which will not last — to build relationships that will last into eternity. Give to the poor, fund mission, invest in disciple-making. Your bank account is going to zero the day you die; use it now for the kingdom while you can. (3) The final verses are the most quoted: "One who is faithful in a very little is also faithful in much... If then you have not been faithful in the unrighteous wealth, who will entrust to you the true riches? ... No servant can serve two masters... You cannot serve God and money" (vv. 10-13). The parable is ultimately a stewardship sermon: you are managing someone else's property (God owns your wealth; you are trustee), and how you handle money now will determine what God entrusts to you eternally. Money is a test, and most people are failing.