To start with, he was a lousy manager. Lost track of inventory; couldn’t keep the books; really had very little idea of where the stuff was that he was paid to steward. No wonder he lost his job.

But, he was also too old for hard, physical labor. What’s more, he had a bit of an ego issue–the idea of having to humble himself and seek public assistance for his daily bread sent a shiver down his spine.

And, to top it all off, his moral compass had no true north on it. Having already wasted his master’s possessions through carelessness, with the time he had left in his job he used his master’s business to win over friends and allies through craftiness. He held a private fire sale for a number of his master’s debtors by reducing what they owed by as much as 20 to 50 percent in the hopes of calling in the favor when the time came for him to need a favor in return.

And yet, this is the guy that Jesus points to in His story and says to His disciples, “Hey! Consider him! Be more like him!”

Honestly, you read this parable and it’s a bid of a head-scratcher. The guy’s a crook. An incompetent, proud, crook. And yet the boss in the story, who paid the price for his employee’s incompetence and his crookedness, “commended the dishonest manager for his shrewdness” (16:8a). So, what’s the point of Jesus’s story?

“For the sons of this world are more shrewd in dealing with their own generation than the sons of light. 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.”

(Luke 16:8b-9 ESV)

Be shrewd. That’s the point.

Jesus wasn’t commending the dishonest manager’s dishonesty. Instead, the story was designed to encourage his followers to be wise. To be prudent. To be thoughtful. To act with intentionality. Mindful of one’s own interests. Planning for the future. In short, to be shrewd.

While he may have only been a so-so steward, the anti-hero of the story aced it when it came to street smarts. He knew that if he used whatever means was at hand (even if it wasn’t his own) to scratch someone else’s back now, he’d have a good shot at someone scratching his back later. He connected the dots between actions now and reward later. So, Jesus holds him up as an example of someone who knew how things worked. Though he was but a “son of this world”, he knew how his world operated. He knew how to plan and invest for his future, even if he had but a limited, temporal, ego-centric view of what that future could be.

Sons of light, says Jesus, would do well to aspire towards modeling the shrewdness of the sons of this world. Not by emulating the dishonest ways of this world, but that they’d benefit from understanding the dynamics of their world, and how the kingdom of light operates.

That the way of the kingdom is to wisely invest now in that which will bring eternal returns later. That sanctified prudence comes from connecting the dots between the opportunity they have on earth to steward temporal treasures, time, and talent in order to store up wealth in heaven which will result in everlasting returns. Understanding why we should wisely, intentionally, purposefully invest now in that which will be used to save sinners and serve saints. Using that which so often corrupts in this world to win that which is incorruptible in the next.

Be shrewd. Know how the kingdom works. Play the long game.

And this too, by His grace, and for His glory.