"There was a certain rich man who had a steward, and an accusation was brought to him that this man was wasting his goods. So he called him and said to him, 'What is this I hear about you? Give an account of your stewardship, for you can no longer be steward.' Then the steward said within himself, 'What shall I do? For my master is taking the stewardship away from me. I cannot dig; I am ashamed to beg. I have resolved what to do, that when I am put out of the stewardship, they may receive me into their houses.' So he called every one of his master's debtors to him, and said to the first, 'How much do you owe my master?' And he said, 'A hundred measures of oil.' So he said to him, 'Take your bill, and sit down quickly and write fifty.' Then he said to another, 'And how much do you owe?' So he said, 'A hundred measures of wheat.' And he said to him, 'Take your bill, and write eighty.' So the master commended the unjust steward because he had dealt shrewdly. For the sons of this world are more shrewd in their generation than the sons of light" (Luke 16:1-8).
Contextually, it can be shown that these words were spoken to an audience that included Jesus' disciples as well as tax collectors, sinners, Pharisees, and scribes (cf. 15:1,2; 16:1,14). This parable was primarily given as a warning against the love of money. It also emphasizes the need to use our God-given material things wisely in preparation for eternity.
The rich man certainly represents God and all humans are His stewards. This is the case because everything and everyone belong to God (cf. Psa. 24:1). Thus, humans are merely stewards (i.e., managers) of the things God has entrusted into our care (i.e., life, time, money, resources, talents, etc.). God has granted all humans certain blessings and He expects them to be used responsibly to His glory; that is, He requires faithfulness in His stewards (cf. I Cor. 4:1,2).
An accusation was brought against a steward who was allegedly "wasting" the rich man's goods. Surely the rich man is angry (and rightly so), for he had placed his trust in this steward to properly manage his goods, but now he is hearing reports that his confidence has been misplaced.
The steward does not deny the accusation or attempt to prove it wrong; in fact, based on his actions in Luke 16:3ff, there is no doubt that the claims against him are true. He is essentially asked to turn in those things pertaining to his stewardship. Let us never forget that all will be asked to give an account of their stewardship someday (cf. II Cor. 5:10).
"What shall I do?" - The steward immediately starts considering his options. He knows that he needs to plan for his future now! He doesn't consider anything with hard physical labor to be a viable option for him as an occupation (either because he was too lazy or just too weak because of past luxurious living). His specific reference to digging should be understood as an allusion to agricultural labor (since this required a lot of turning over of earth or "digging"). The wicked steward, because of his pride, is ashamed to beg though we quickly learn that he is not ashamed to steal!
He came up with the bright idea of making his master's debtors his debtors so that when he was cast out of his position as a steward certain ones would treat him well since they owed him a favor.
"So he called every one of his master's debtors to him" (Luke 16:5). Although the text only gives the details of two debtors coming to him, there were probably many more than that (considering the wording). The first debtor owed 100 measures of oil. Some have estimated this to be under $200 in American money. This is quite a sum, however, since the daily wage of a working man was equivalent to less than a quarter.
"Take your bill, and sit down quickly and write fifty" (Luke 16:6). This activity must be done in haste while the wicked man still had authority as a steward and also so he would not get caught in further dishonesty. A 50% reduction represented a large sum of money that would put the debtor under obligation to the steward.
Although the numbers are different, the same thing is done with the second debtor (and, by implication, all of the other debtors). We assume that the debtors didn't ask any questions of this steward. They probably just considered this a lucky break and went away delighted.
We will continue studying this parable in our next lesson.