3 Surprising Lessons from Jesus’ Weirdest Parable

Hieronymus Bosch, Death and the Miser (detail) (1516)
Hieronymus Bosch, Death and the Miser (detail) (1516)

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?]


  1. So many excellent points. Try Darrell Castle, Constitution Party candidate, if the major parties simply aren’t working out for you. Pro-Life is part of his party’s platform.

  2. This may be completely wrong, but I always saw the master, steward, and debtors as foil characters for God the Father, God the Son, and us faithful sinners saved through Christ’s love. As in, this parable tells a fallen, human story to underscore the holiness of the Gospel’s broader story of salvation. (Kind of like the guy in another parable who finally answers the door in the middle of the night out of sheer annoyance at the person who needs help — that’s not actually how prayer works. Those are imperfect foil characters to illustrate in fallen, human terms how much more perfectly God hears and answers our prayers.)

    When I was a child and first heard about the steward suddenly writing off debts, the first analogy that sprang to mind was Christ “writing off” our sins, not because we earned it or somehow repaid Him — our salvation is unearned and gratuitous. Revisiting the analogy as an adult, I find more elaborate parallels. Instead of writing it off partially like the steward did (by 50% or 20%), Christ forgives us brazenly, utterly and completely. His suffering and death is 100% atonement for our sins. And He does it not to curry favor with us so that we might be able to help Him later, but out of perfect selflessness and love for us. And instead of having to do it secretly and furtively, Christ’s sacrifice for us is with the full knowledge and blessing of God the Father. In the story, the once-positive relationship between the master and steward is now broken and distrustful, but the Father and the Son share a loving relationship. And yet, in spite of the strained relationship between master and steward, the master still finds something prudent and “commendable” about the shrewdness of the steward, and so it’s suggested implicitly that the master begrudgingly honors the undeserved debt forgiveness. So, how much more perfectly does God embrace the sacrifice that his beloved Son makes for us, and welcome us into Heaven through Christ’s perfect atonement?

    (I admit that my allegory sort of falls apart with the last paragraph, which is basically a hodgepodge of advice about not loving wealth, faith/dishonesty in small things/big things, etc. Some have suggested that those are fragments of different paragraphs of scripture that survived out-of-context and were woven together and stuck in there. I dunno. I just try to stick to the parts that inspire me.)

  3. One thing is for sure, this rich man is a very good man. He let’s the criminal manager off the hook with a smirk and a jest, amazed at how crafty he is. No anger is even shown, just amusement.

    As the owner of a business this also has happened to me MANY times. The more charitable I was to those I worked with, the more abuse I usually got. One guy stole $1000.00 and moved out to the area. I worked with him as a friend for about 1 year. I bought a used car for another worker in his extreme necessity, but in no short time he was telling other workers that I’m full if —- with all of my religion. I bought another person a used truck, and worked with him for about a year. And then when I told him I can’t really help him out anymore, he flew off the handle screaming and yelling, as if he never benefitted from me, or I hadn’t ever done anything for him. I fired one guy who was a veteran of the Vietnam war, for the South Vietnamese army. He was also a prisoner of war in a Viet Cong prison camp. Other workers complained to me that every time I left the warehouse He would treat them like a mean tyrant…and would do almost no work himself. I also learned from his very mouth that other Vietnamese gangs were looking to kill him for many crimes he committed in the past, in refugee camps, etc.. After I fired him, he threatened that he would stand by the warehouse gate and kill anyone who took his place…and meant it. He had a huge combat knife that was my partners. One day, about 2 weeks later, he walked up to me, said he had a present for me, and handed me the knife. He then said he wasn’t going to do any thing to anyone. I said OK and kind of wiped my brow. I thought seriously that that might have been the end for me.

    What Jesus said happens all the time in one way or another, with those who own businesses. There is really a lot of theft and abuse, and especially if you are very kind and generous. They get use to it, and then take advantage…especially if they percieve that you will fire them soon. They don’t like to see the charity/party ending for them and so they take even more advantage then usual.

  4. I follow Phil Lawler on twitter, and read his book. He has great insight into current developments in the Church.

    Christians have gradually become aware of the strategic failures of the Pro-Life movement. As a Catholic and Knight of Columbus I can attest to the moral lethargy prevailing today. Lawler describes in his book how, during the 90’s the partial birth abortion ban (which was eventually vetoed by President Clinton) the Knights attempted to exert pressure on Catholic Senators, but were eventually squelched BY THE CATHOLIC HIERARCH. Appeasement has not worked. Beige Catholicism is a joke. The culture must be restored; mere conservation will not work.

  5. ‘be wise as serpents and innocent as doves’

    Why did the early Israelite desert dwellers view the serpent as evil? Why is it considered such a symbol for evil, if not a biological evil in all reality?

    As desert dwellers, pastors and travelers the Israelites had a lot of time on their hands to observe the very few natural resources that survived in the desert climate and environment that they often found themselves in. And having great wisdom, they could not have ignored an analysis of the biology and natural habits of the serpent which was always a threat for them when they worked or travelled. So, the Israelites had abundant time to study the nature of the venomous serpents that were always close at hand in their everyday lives. As a comparison to the serpent they also could not ignore the biology of the many bird’s that flew around them. there was a great biological contrast between these two animals, and they could not help but note this in sacred scripture.

    So what did they see in this observation of the differing physical characteristics of serpents and birds, snakes and doves, for instance? First, and most notable, serpents/snakes have no limbs. But modern biology shows that far back in their evolution they did indeed have limbs, so snakes have undergone a sort of biological regression. That is, at some point they made a biological u-turn, returning to a more or less ‘fish like’ state of biological simplicity. Most other land life did the contrary, and from a state of biological simplicity became ever more developed in biological ‘complexity’, with birds being a good example of this. Birds evolved not only limbs, but those same limbs evolved into wings. So birds and snakes are sort of evolutionary opposites.

    Moreover, a simple study of snake biology shows that not only do snakes lack limbs to touch with, but they also have very poor eyesight to see with. Moreover the cannot even blink, or shield and shade their eyes from the brightness of the Sun’s rays when above ground. in contrast, birds such as doves can blink their eyes and focus their eyesight with great vision and agility; and they can close their eyes so as to rest comfortably even in the bright sunlight.

    Snakes also lack a means of maintaining warmth in their bodies, except through nutrition and metabolism. But snakes don’t eat very often and so also don’t enjoy the simple pleasures of life that birds to, who feed themselves regularly by flying from place to place finding both fruits and insects for their nourishment. Snakes on the other hand, lacking eyesight need to be guided to their food through the use their heat sensing tongues that have evolved to be a type of thermal imaging mechanism to guide them to their prey.

    In some ways, the saying “their God is their stomach” might be applied to the snake, as both the thermal sensing tongue and stomach have evolved to be the predominant sense organ for this interesting creature. Regarding the mouths of snakes, a further observation of the early Israelites would find that they are not capable of vocal communication. On the contrary, birds communicate very beautifully with each other, even singing the most exquisite songs. Snakes do not have this trait, and consequently they are also very unsocial creatures. Their meager social life is pretty much limited to the unique ‘orgy type’ mating… ‘den of vipers’ events…that they have about once per year.

    All of these biological differences between the serpent and the dove can be noted by anyone who has taken the time to observe them in their natural habitat. and even if not in their own ecosystem, and for instance you purchase a pet snake or dove, or parakeet… the differences between these two animals are easy to observe.

    It is also amazing that the Book of Genesis mentions that there was a biological change to the serpent after the ‘fall of Adam’: “thou art cursed among all cattle, and beasts of the earth: upon thy breast shalt thou go, and earth shalt thou eat all the days of thy life.” (Gen 3:14)

    And modern science notes this in a recent finding:

    “…a Yale study from earlier this year (2015) that found snakes evolved on land and not in water, UPI reports. That study used genomes, fossils, and more to determine the ancestors of modern snakes lost their front legs approximately 128 million years ago, though they still had tiny hind legs.” (Science Advances)

    All in all, that snakes lack so many of the physical attributes that make humans happy, lacking almost all of the physical senses, and to boot, many snakes are deadly poisionous to other creatures… what better biological example for evil could be brought forth than the snake? And what better contrast of freedom of movement, beauty and gentleness…than the dove?

    Thanks for bringing this topic up, Joe.

  6. I’ve been thinking more about this parable. I believe it is one for our time. The children of light (i.e. The clergy) do not know how to deal with the present generation. Maybe that is why the Church wants more lay participation.

  7. It’s interesting that the steward is praised for cutting deals with his masters debtors, but later we are told that “one cannot serve two masters”. One cannot compromise with the devil and hope to save his soul.

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