Puzzling Passage: Luke 16:1-9
V1-8a – Parable
V8b-13 – Jesus’ explanation
V14 – Further context

The Parable of the Dishonest Manager
He also said to the disciples, “There was a rich man who had a manager, and charges were brought to him that this man was wasting his possessions. 2 And he called him and said to him, ‘What is this that I hear about you? Turn in the account of your management, for you can no longer be manager.’ 3 And the manager said to himself, ‘What shall I do, since my master is taking the management away from me? I am not strong enough to dig, and I am ashamed to beg. 4 I have decided what to do, so that when I am removed from management, people may receive me into their houses.’ 5 So, summoning his master’s debtors one by one, he said to the first, ‘How much do you owe my master?’ 6 He said, ‘A hundred measures of oil.’ He said to him, ‘Take your bill, and sit down quickly and write fifty.’ 7 Then he said to another, ‘And how much do you owe?’ He said, ‘A hundred measures of wheat.’ He said to him, ‘Take your bill, and write eighty.’ 8 The master commended the dishonest manager for his shrewdness. 
For the sons of this world are more shrewd in dealing with their own generation than the sons of light. 9 And I tell you, make friends for yourselves by means of unrighteous wealth, so that when it fails they may receive you into the eternal dwellings. 10 “One who is faithful in a very little is also faithful in much, and one who is dishonest in a very little is also dishonest in much. 11 If then you have not been faithful in the unrighteous wealth, who will entrust to you the true riches? 12 And if you have not been faithful in that which is another’s, who will give you that which is your own? 13 No servant can serve two masters, for either he will hate the one and love the other, or he will be devoted to the one and despise the other. You cannot serve God and money.”
14 The Pharisees, who were lovers of money, heard all these things, and they ridiculed him.

Why it is Puzzling:
The dishonest manager was charged with wasting/ squandering the master’s possessions (v1) and so we assume he is guilty since he made no attempt to defend himself (v3) and the manager’s dishonesty is the central theme of the parable. The dishonest manager then doubled down on his dishonesty by wasting even more of his master’s possessions by cancelling portions of his master’s debtors’ debts so they would owe him favours. In the end, the master commended the dishonest manager even though he was being cheated by him because he found him to have great foresight in planning for his own future; how he was able to take care of himself and secure his future. “Sons of light?” (v8b) are God’s people. Therefore the first impression we get from reading this is: how puzzling it is that Jesus is telling us to make friends using ill-gotten gains (unrighteous/ dishonest wealth) so that when things don’t work out (“when it fails” v9), that they may somehow be of help in eternity. Should God’s people be modeling after the ways of a dishonest manager? Is this corrupt manager supposed to be an example for “sons of light” to follow? Would God promote gaining dishonest wealth? Can using dishonest wealth to make friends somehow aid in us being welcomed in eternity?

Alternative interpretation: 
The use of the term “unrighteous wealth” can mean ill-gotten gains OR wealth in general (earthly wealth is understood to have a corrupting influence and thus is being termed as “unrighteous wealth.” So it does not necessarily mean wealth gained through cheating. Our focus is to learn the principle of the parable and not to model after the bad person. In other words, Jesus’ point is for Christians to learn the principle of generosity in using the Master’s wealth to win friends for eternity. So that when earthly wealth fails (because at some point we will die and earthly wealth will be of no use to us) those friends will be in heaven welcoming you. Therefore, we do not model after the dishonesty part, but model after the principle of being far-sighted. We are to constantly plan ahead; planning for eternity by using our Master’s wealth in the spirit of generosity. The idea of generosity is inferred through the generous debt cancellation of the dishonest manager. He was not stingy with his Master’s resources and that is what made him effective in winning friends.
As a ‘son of this world’ (v8) the dishonest manager knew how this world works. So he used his worldly shrewdness so that he would not end up homeless. Even his worldly master appreciated his shrewdness. Jesus’ lesson is for ‘sons of light’ to be as shrewd in understanding how the kingdom works. So in focussing on the principle expounded, this solves the disturbing notion of emulating dishonesty. The dishonest manager sought to win friends so that they would be of use to him in offering shelter (v4). God’s people are to win friends so that they will see them in the heavenly shelter. Notice how “your own” (v12) is tied to “true riches” (v11) – these likely refer to spiritual responsibilities (Christian ministries) or spiritual children.

The Point:
– Be generous with the Master’s money in soul winning.
– God has made all of His people managers of unrighteous wealth.
– Our unwillingness to use it for soul winning shows that we are serving mammon rather than God (similar to the lovers of money in v14).