Read: Luke 16:1-8
Jesus’ parables often had a twist or shock value to them that would help in the memorization of the parable. For instance, in the last parable, the Parable of the Loving Father, none of the listeners were expecting the father of the prodigal son to receive his son in such a way. They all expected the father to be tough and a disciplinarian in his son’s return home. The Parable of the Shrewd Manager again has shock value, for none of the Lord’s listeners expected the story to have a twist at the end.
Jesus spoke of a wealthy landowner who is distant from his estate of perhaps hundreds or thousands of acres of land. He has an employee, a steward or manager, who is supposed to be managing his business affairs to the betterment of the landowner. This man had been appropriately trained in handling significant financial matters, writing out tenant agreements to farmers, making loans against the harvest on the lands, the managing of debts, and keeping detailed financial books. The wealthy landowner gets word that the manager is cheating him out of some of the proceeds of the land. Like the young prodigal, this manager was squandering the owner’s goods. He is called to appear before the landowner, and in the face–to–face meeting, he was confronted with his embezzlement and told that he was out of a job; he is sacked or fired.
We should not think that this land-owner is a picture of God, for not all the details of parables represent someone or something. We are only to get the main point, which comes at the end of the story. The master found out the manager was “wasting his possessions” (v. 1), but the owner then makes a mistake. He does not tell the man to clear his desk and have him escorted off the property. Instead, he was given time before his final day. No manager today would make that mistake with an employee found mismanaging company funds. Jesus didn’t say that the master had evidence of his embezzlement, but it is intimated from the text and the following narrative. The master decides that he needs to review the books to determine further how deeply the manager had gone in his betrayal of the master’s trust. This delay gives the manager time to think of what he will do while he is still in the master’s employ. He sits down and begins to take inventory of his present circumstances, and he thinks of his future. He concludes that soon he will have nowhere to live. Most managers lived on the land that they were tending. He also will have no money, and thirdly, his reputation will be gone once word gets out. A bright idea comes to him.
There is no mention of the manager having a family, but with a responsible job overseeing land tenants, we can logically say that he was not a young person. He had several skills that could be only be acquired with time and experience. He was not young anymore, so he lacked the strength to do a manual job like digging. He didn’t want to beg, either. That would hurt his pride and self-image. This manager became deceitful over the time he had been embezzling his master, so he still thinks of how he can benefit himself with his existing resources while they are still at his disposal. He is a “wheeler-dealer,” so to speak. Even though he is fired, he is still able to “cook the books.” The wealthy owner should have sent someone in authority to collect the records to safeguard the business. In today’s terms, he was being asked on a specific day to bring along the records of all the business transactions and then clear away his desk.
Before his final day, he decided to use what was at his disposal in the present time to better position himself in the future. He would falsify the books and use his master’s assets. He shrewdly went to the first person, and upon agreeing the man owed a hundred measures of oil, he told him quickly to rewrite it to be fifty measures, instead. This amount is the proceeds from about 150 olive trees, approximately 900-1,000 gallons of oil, or around the wages of three years for an ordinary person. He cut the man’s debt to half of what he owed. He then went to the next person, and they agreed that he owed one hundred measures of wheat, i.e., 1,000 bushels of wheat, taking 100 acres to produce. He tells him to rewrite the debt to eighty (vv. 5-7). All those who were listening to Jesus that day would have been wondering what the land-owner would do to the manager when he finally got the books and saw the depth of the cheating.
All of them were shocked to hear the next words out of the mouth of Jesus:

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