Luke 16:1-8 is notoriously difficult to interpret. Was the manager in the parable dishonest? If so, why did the master commend the manager's act of instructing the master's debtors to alter their bills? On the other hand, how could this dishonest act be shrewd? More disturbing was Jesus' affirmation of this act by creating a teaching out of this parable. Traditional interpretation contends that Jesus was making a point by using a negative example. Interpreters who pay attention to ancient culture and its economic system suggest that the manager's act was not illegal. After surveying the foremost interpretations of this parable, I suggest that the manager was both dishonest and shrewd and that this understanding echoes with the parable's context as well as with Luke's eschatology and theology of wealth.