The weirdest and most troubling of Jesus’ parables is almost certainly the parable of the dishonest manager. I’m going to quote the whole thing, because it doesn’t do it justice to simply explain it. At every turn, the parable seems to go in the direction you least expect (Luke 16:1-13):

Then [Jesus] said to the disciples, ‘There was a rich man who had a manager, and charges were brought to him that this man was squandering his property. So he summoned him and said to him, “What is this that I hear about you? Give me an account of your management, because you cannot be my manager any longer.” Then the manager said to himself, “What will I do, now that my master is taking the position away from me? I am not strong enough to dig, and I am ashamed to beg. I have decided what to do so that, when I am dismissed as manager, people may welcome me into their homes.” So, summoning his master’s debtors one by one, he asked the first, “How much do you owe my master?” He answered, “A hundred jugs of olive oil.” He said to him, “Take your bill, sit down quickly, and make it fifty.” Then he asked another, “And how much do you owe?” He replied, “A hundred containers of wheat.” He said to him, “Take your bill and make it eighty.” And his master commended the dishonest manager because he had acted shrewdly; for the children of this age are more shrewd in dealing with their own generation than are the children of light. And I tell you, make friends for yourselves by means of dishonest wealth so that when it is gone, they may welcome you into the eternal homes. ‘Whoever is faithful in a very little is faithful also in much; and whoever is dishonest in a very little is dishonest also in much. If then you have not been faithful with the dishonest wealth, who will entrust to you the true riches? And if you have not been faithful with what belongs to another, who will give you what is your own? No slave can serve two masters; for a slave will either hate the one and love the other, or be devoted to the one and despise the other. You cannot serve God and wealth.

So the passage begins by describing a manager (a “steward,” in some translations) who is being fired for being bad at his job. Due to the man’s limitations and his pride, he decides that his best recourse is to cut deals with his master’s clients so that he can try to leverage this into a job with them.

Ahh, we might think, so that’s why he’s getting fired. I bet the master is going to find out and be furious, and we’ll all learn a lesson about dishonesty, right? Nope. Quite the opposite. The master praises him for his shrewdness.

What on earth is going on?

1. It’s Not Actually Praising Greed or Dishonesty

Let’s get one thing out of the way right off. The parable isn’t literally calling us to steal or to obtain wealth through dishonest means. The passage closes by warning us that we can’t love God and love money, after all. St. Augustine comments,

The steward whom his Lord cast out of his stewardship is nevertheless commended because he provided himself against the future. As it follows, And the Lord commended the unjust steward, because he had done wisely; we ought not however to take the whole for our imitation. For we should never act deceitfully against our Lord in order that from the fraud itself we may give alms.

Instead, “we should understand that if the steward who acted deceitfully, could be praised by his lord, how much more they please God who do their works according to His commandment.”

2. Saints can look to Sinners as a Model

Think of a heist movie, like Ocean’s Eleven or The Italian Job or anything of the sort. Although these movies are fictional, they’re a good reminder that criminals will go to great lengths, and undertake extensive planning, to steal riches. Or think about all of the time, energy, and sheer human ingenuity that people have put into trying to plan (or cover up) the perfect crime: be it murder, theft, or anything else. Think about how much effort and intentionality the seducer puts into his plan to lure the married woman.

Evil often requires a great deal of brilliance. A 2005 film on the Enron scandal was aptly-entitled Enron: The Smartest Guys in the Room. While I never saw the film, I have spoken with one of the FERC commissioners, and it’s true: the guys at Enron were doing things that the regulators had never even dreamed of specifically outlawing. In the end, they went after them with a wire fraud statute that was several decades old.

But it’s not just the big sins that are like this. Even the act of telling a single lie often requires a great deal of additional lying and scheming simply to cover up the original lie.

Now contrast this with how we approach the things of God. We often have this attitude of “I’ll go to Mass… so long as soccer practice doesn’t get in the way.” Remember Cain and Abel? God accepted the sacrifice of Abel because Abel offered God the firstborn of his herd (Gen. 4:4); He rejected the sacrifice of Cain who, instead of giving God the firstfruits of his harvest, simply gave Him “an offering of the fruit of the ground.” (Gen. 4:3). We’re often even worse than Cain – we give God the leftovers… or nothing at all, if there don’t happen to be any leftovers. This is true of tithing, but it’s especially true of time: if we’ve got a little bit of leftover time, we’ll pray.

Imagine what would happen if we spent as much time, energy, effort, and ingenuity into being Saints as the truly wicked put into being sinners. The world would be on fire with sanctity! For that matter, consider how much better saints we would be if treated God’s plans like they were our own, or if we put as much effort into receiving the Eucharist as we would if the priest were instead giving out novelty checks. Theophylact of Ochrid, the 11th century Greek Orthodox Biblical commentator, put it somewhat more dryly: “it is found indeed in the management of human affairs, that we prudently order our own things, and busily set ourselves to work, in order that when we depart we may have a refuge for our life; but when we ought to direct the things of God, we take no forethought for what shall be our lot hereafter.”

3. Naivety and Stupidity aren’t Virtues

One of the most pertinent lines in the Gospel right now is “the children of this age are more shrewd in dealing with their own generation than are the children of light.” We see it all over the place. A young Katy Hudson records a Gospel record and it goes nowhere: it literally sells 200 copies. She abandons Gospel for secular music. After a few years, after having changed her stage name to Katy Perry, she releases a song called “I Kissed a Girl,” and it sells 4.6 million copies in the U.S. alone.

Contemporary Christian art in many of its forms is currently embarrassing. This need not be this case. It wasn’t always this way. While much of the worst contemporary art is religious, the greatest Renaissance and Baroque art is religious.

We Christians are proving to be as foolish and inept in politics as in art. Even though a majority of Americans consistently favor outlawing most or all abortions, the pro-life movement has managed to become “the GOP’s second-class citizens,” in Phil Lawler’s phrasing, and neither of the two major-party presidential candidates (Trump or Clinton), nor the two minor-party presidential candidates (Johnson or Stein) are believably pro-life.* The political and legislative strategies of the pro-life movement (and moral conservatism more broadly) often simply don’t make sense, and Christians in general punch well below their (our) weight on the political scene.

This might not be a major problem if modern Christianity were avowedly apolitical, actively seeking to advance the Gospel radically apart from the corrupt and rotting State. But instead we find Christians evermore putting their hopes in secular Messiahs, political heroes that have managed to disappoint nearly 100% of the time, all while failing to figure out how politics works.

It might sound scandalous for me to say that we need to get our act together and start learning from the Culture of Death. But if you’re scandalized by that, you’re really not going to like what Jesus has to say (Matthew 10:16): “See, I am sending you out like sheep into the midst of wolves; so be wise as serpents and innocent as doves.”

Modern readers have lost the edge that those words originally carried. Serpents, to the Jewish mind, represent the satanic. It’s how Satan is presented in both the first and last book of the Bible (Genesis 3:14-15; Revelation 12:9). Jesus’ point in using serpentine imagery is to remind us that the devil is evil, not stupid. Gen. 3:1 acknowledges as much. And it’s for this reason that 1 Peter 5:8 reminds us to “Discipline yourselves; keep alert. Like a roaring lion your adversary the devil prowls around, looking for someone to devour.” And it’s for this reason that innocence is laudable, but naivety isn’t.

So let’s strive to be as crafty as the devil, but as innocent as the angels.

*At this point, some readers will want to chide me that Trump, despite a lengthy pro-abortion track record, now claims to be pro-life (although not pro-life enough to bring it up during debates or anything). I’ve had multiple people tell me, in all seriousness, that we have to take him at his word because he doesn’t have any legislative track record to disprove his obviously-false claim (apparently, praising Planned Parenthood during the Republican primary wasn’t a big enough clue). In the words of SBC’s Russell Moore, “Why Trump would be more faithful to vows to religious political activists than he has been to people named “Mrs. Trump,” they do not tell us.” To this, I ask: is any other political group in America as willfully gullible as we are? This is what being as wise as a dove looks like. [Mind you, I can still understand why a pro-lifer would vote for Trump as the least-bad of the major-party options; but let’s not be naive about how bad he is, okay?]