The parable of the dishonest steward appears in the Gospel of Luke, and is very interesting:

Then he also said to his disciples, “A rich man had a steward who was reported to him for squandering his property. He summoned him and said, ‘What is this I hear about you? Prepare a full account of your stewardship, because you can no longer be my steward.’ The steward said to himself, ‘What shall I do, now that my master is taking the position of steward away from me? I am not strong enough to dig and I am ashamed to beg. I know what I shall do so that, when I am removed from the stewardship, they may welcome me into their homes.’ He called in his master’s debtors one by one. To the first he said, ‘How much do you owe my master?’ He replied, ‘One hundred measures of olive oil.’ He said to him, ‘Here is your promissory note. Sit down and quickly write one for fifty.’ Then to another he said, ‘And you, how much do you owe?’ He replied, ‘One hundred kors of wheat.’ He said to him, ‘Here is your promissory note; write one for eighty.’ And the master commended that dishonest steward for acting prudently. “For the children of this world are more prudent in dealing with their own generation than are the children of light. I tell you, make friends for yourselves with dishonest wealth, so that when it fails, you will be welcomed into eternal dwellings.”

This is a perplexing parable because Jesus is drawing a lesson from a dishonest man, which presents the difficulty of figuring out which parts we’re supposed to copy and which parts we’re not. And other questions like, “why did the master praise the dishonest steward for giving away his property?” To figure this out, we need to look at what actually happened: yes, the dishonest steward gave away some of his master’s property by canceling some of the debt, but he didn’t give it all away. And he could have.

In modern times, when a person is fired, the usual procedure is to lock them out of all of the computer systems of a business before telling them that they’re fired, so they can’t do anything bad on their way out. But the master doesn’t do this with the dishonest Steward. Instead, he leaves him Steward until he has drawn up a full account of his stewardship. Why?

Because the master didn’t know what he had.

In order to know what was his, he needed the dishonest steward to tell him. The dishonest steward was thus in a position to give away everything. If he told his master, “I’m sorry, but you’re broke” the master did not know better.

Further, since he was still steward, he was within his rights to entirely cancel the debts of the people whose debts he partially forgave. It was not honest, but it was his right. So why didn’t he entirely cancel out the debt of those debtors?

We’re not told, of course, but there is a strong hint in the fact that he did not forgive the same amount to both debtors. He forgave one half his debt and the other a fifth of his debt. Since he was praised for being prudent, we must assume that he forgave different amounts because of reasons specific to each, that is, because it was prudent. Perhaps the one could only repay half anyway, and the other could repay four fifths. Perhaps the one who was forgiven half had done something for the master earlier while the one who was forgiven a fifth hadn’t. We don’t know, but we must presume that the actions made sense in context.

And what about this from the master’s perspective, when he hears about it? Had the Steward canceled the entire debt, he would be very angry at the dishonest steward. But he was left with two thirds of what he was owed, which was far better off than he might have been. It’s not optimal, but if the master was realistic—and he seems to have been realistic—he got rid of the steward far more cheaply than he might realistically have and better than many have. (Just look up the history of how many sports figures were left penniless by dishonest business managers.) Moreover, he might even have received some small benefits from the forgiveness of the debt in addition to the money he got back. If the one who was forgiven half of his debt had done something for the master, that debt is now paid. If the debtor was only able to pay half, he might now get the half promptly. If nothing else, in not making a fuss over the canceled portion of the debt, he might at least receive good will from the debtor in case the situation is ever reversed and the master is the one who owes. It’s possible that he got rid of the dishonest steward even more cheaply than we know.

This also shows a great deal of understanding of human nature on the part of the dishonest steward, because consider what happens next: he’s going to ask the people whose debts he reduced for a job. That’s a delicate thing to do when he was just fired for dishonesty. Sure, they have reason to like him, but at the same time a job for many years can easily cost a lot more than twenty kors of wheat, especially if the guy is dishonest. Critically, he shows that while he’s dishonest, he’s not too dishonest. If the debtors are at all reasonable, they know that it’s very hard to find a completely honest man—consider how long Diogenese looked without finding one—so one who is only a bit dishonest is a reasonable choice. And he proved himself to be only somewhat dishonest by his actions when the metaphorical fecal matter had hit the artificial wind generator, i.e. when he was deeply stressed and might have been desperate or resentful.

Putting this all together, we can see what Christ referred to when he said that the children of his world are more prudent in dealing with this generation. The dishonest steward knew how people thought and acted, and acted accordingly. In modern terms, his psychology was good, even if his morals were not. He knew how to effectively manipulate people; he manipulated them with the truth. The great advantage of manipulating people with the truth is that, when they find out, they are not angry with you.

And here we come to the part to imitate: the common name for manipulating a person to his own benefit is “supporting” him. We, each of us, have an influence on the people we meet in this life, and if we will their good, we should support them. To do that, we must be able to understand things from their perspective, and how we and they and the things under our control relate, and then use the truth to manipulate them to their benefit. That is, to effectively support them.

I think that this also sheds some light on what Jesus says after—to use dishonest wealth to make friends so we will be welcomed into eternal dwellings. All wealth—all possessions—always have some dishonesty about them because we never do a perfect job. Everything we make, or deliver, or do for another is always, because of our human weakness, at least slightly less than it should be. But this does not completely invalidate it; there is still good that we can do with it and if we use it well—that is, prudently—it can make people better off and it’s worth doing this. And it’s not easy to do this and it’s worth putting the effort into doing it well.

This stands against the mistake of being “so good that you’re good for nothing,” that is, so fixated on purity that you never accomplish anything good. That’s not to say that one should choose to be dishonest; heaven forbid. But it does mean that there are limits to how much one should allow the fear of what is technically called “remote material cooperation” to prevent one from ever doing anything.