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This particular parable has probably raised more questions and concerns than any other. Usually, Bible students want to know how Jesus could use the behavior of an irresponsible and conniving manager ("steward") as an example for his disciples. The answer to this question is related to the rich man's admiration for his steward's "shrewdness"--I think "cleverness" might be a better word. He certainly acted wisely in regard to his own self-preservation. There are two issues here we have to discern if we are going to benefit from this passage. First, it was not the steward's specific actions that his master admired, but the wisdom that formed his actions; namely, (1) he knew he would soon be out of a job, (2) he could not imagine himself in any other form of employment, (3) discerning his future, he took actions in the present, and (4) he ingratiated himself (made friends) with his master's debtors so that they would think well of him--or perhaps obligated--when he came looking for work. It was this looking ahead and planning for the future that both the master and Jesus commended. In fact, Jesus' observation that "the children of this world are more shrewd in dealing with the world around them than are the children of light," refers precisely to this facet of the steward's actions. The Lord's disciples know the future that is coming--death and judgment--, yet do little to prepare themselves for it. (For a good elaboration on this point, read the last story Jesus told in this same chapter, vv. 19-31.) I think that answers your question, James, but I also feel it's important to notice the second issue. Jesus drew a comparison between two very different contexts. One context is this world, in which "unrighteous mammon" is a necessary resource that can be used for good. The other context is heaven ("everlasting habitations" NKJV) and "true riches" (vv. 9-13). The points that Jesus stresses are: (1) think about your future and plan and act wisely in light of it, (2) use the resources you have in this world to prepare a warm reception for yourself in the next, and (3) faithfulness (trustworthiness--unlike the steward) in our commitment to God is necessary if we hope to be entrusted with heaven's true wealth. Short answer: It was not the steward's wrongdoing that made a good impression on his master, but his foresightedness.
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