What kind of future are you investing in? Jesus seemed to praise a clever manager who used underhanded means to secure a profitable and happy future for himself. What's the point of this perplexing parable? The steward very likely overcharged his master's tenants for their use of the land and kept more than his fair share of the commission.
Before news of his dismissal becomes public knowledge, the shrewd steward strikes a deal with his master's debtors. Such a deal won him great favor with the debtors. Since he acted as the landowner's personal agent, such a deal made his master look very generous and forgiving towards those who owed him money. Since the master could not undo the steward's cancellation of the debts without losing face and making his debtors resent him, he praises the steward for outwitting him as a generous and forgiving landowner.
Jesus obviously thought that the example of a very clever manager who took thought for his future well-being would be a perfect illustration for anyone seriously interested in securing their future in God's kingdom. What lesson can we learn from this parable? The dishonest steward is commended for his shrewdness. The original meaning of "shrewdness" is "practical wisdom" or "prudence". It is the ability to deal with a given situation, to see what needs to be done and to do it. Three other parables where Jesus commends this kind of practical wisdom are the parables of the wise builder who built his house on a rock (Matthew 24:7), the wise steward who orders his household well (Matthew 24:45; Luke 12:42), and the wise virgins who remembered the oil for their lamps (Matthew 25:2-9).
Jesus commends his listeners to be wise and prudent not just in the exercise of their material and financial resources, but more importantly in how they use these resources for advancing God's kingdom and the work of the gospel.
Jesus concludes his parable with a lesson on what controls or rules our lives (Luke 16:10-13). Who is the master (or ruler) in charge of your life? Our master is that which governs our thought-life, shapes our ideals, controls the desires of the heart and the values we choose to live by. We can be ruled by many different things – the love of money or possessions, the power of position, the glamor of wealth and prestige, the driving force of unruly passions and addictions. Ultimately the choice boils down to two: God or mammon. Mammon stands for material wealth or possessions or whatever tends to control our appetites and desires. There is one Master alone who has the power to set us free from the slavery of sin and addiction. That Master is the Lord Jesus Christ.
(Adapted from Don Schwager)
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