I’ll be honest—when I was preparing this sermon last week, I kept hoping I’d misread the passage. Surely Jesus wasn’t actually holding up a corrupt accountant as our role model, right? I mean, this guy gets caught stealing from his boss, and when he’s about to get fired, his brilliant solution is… to steal some more, much like the character in the shrewd steward parable.

But there it was in Luke 16, clear as day. And Sunday morning, I had to stand in front of my congregation and explain why Jesus just told us to be more like someone who’s basically running a medieval Ponzi scheme, a striking element of the shrewd steward parable.

I could see people shifting uncomfortably in their seats. Shouldn’t we be talking about integrity and honesty? Shouldn’t Jesus be holding up the Sunday school teacher or the volunteer firefighter as our role model?

As we dive deeper, we uncover the powerful messages within the shrewd steward parable that challenge our understanding of wisdom and resourcefulness.

But here we are, wrestling with a story where the “hero”—if we can call him that—is a manager who gets caught stealing from his boss. When he’s about to get fired, he calls in all the people who owe his boss money and slashes their debts. “You owe a hundred jugs of olive oil? Make it fifty. You owe a hundred containers of wheat? Let’s call it eighty.” He’s basically having a going-out-of-business sale with someone else’s inventory.

And then—this is the part that should really make us uncomfortable—his boss finds out and commends him for being shrewd. Not ethical. Not honest. Shrewd.

The Plot Twist That Changes Everything

Understanding the Shrewd Steward Parable

But Jesus isn’t done making us squirm. He ends this whole parable with something that cuts right to the heart of everything: “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.”

Wait—so this isn’t really a story about creative accounting at all, is it?

It’s about who we’re really working for. The manager understood something we often miss: he was about to be forced to choose between masters, and he chose relationships over reputation, community over personal security. He acted with the kind of urgency that comes from knowing you can’t serve two masters at once.

In a world where we’re constantly told that good people follow the rules and bad people break them, where we’ve been raised to believe that if you just work hard and play by the rules everything will work out, Jesus seems to be saying something scandalous: sometimes the “bad” people understand something about urgency and choosing sides that the “good” people have forgotten.

The Manager’s Brutal Honesty

The dishonest manager has a choice to make. He’s being demanded to give an accounting of his stewardship, and he knows he’s being fired. He’s brutally honest with himself—he can’t do manual labor. It won’t sustain him, and he won’t be good at it.

So he has three choices: defend himself, make excuses, or act decisively.

He chooses option three. He decides to choose relationships. He cuts debts, makes allies, and builds connections he can rely on rather than trying to save his reputation.

And here’s what really gets me: his boss commends him for it. Not for being ethical, but for being shrewd—cunning, strategic, intentionally disruptive. He’s shrewd about what really matters for survival and community.

Now, Jesus isn’t endorsing embezzlement here. But he is challenging our assumptions about what faithfulness looks like. That’s what Jesus does all the time in his parables—just when we think they’re straightforward, he throws us a curveball.

Grace Disrupts Our Categories

God’s love does that too. We talk about grace as God’s love freely given—nothing earned, nothing to work for, just pure gift. And Jesus is trying to tell us that grace disrupts our neat categories of “good” and “bad” behavior.

The manager gets what we sometimes forget: we are all stewards. We’re all caretakers. We’re not owners, and our time is limited. God’s kingdom—the way God shows up in our world—sometimes needs swift, radical action that makes respectable people uncomfortable.

Like the manager, we’re called to act decisively with our resources to build relationships and community, even when it means giving away money we’re “supposed” to save, or helping people we’re “not supposed” to help, or challenging systems we’re “supposed” to respect.

Holy Urgency in Action

This kind of holy urgency isn’t just happening in the world of the Bible. While politicians and experts debate the right way to handle inequality, climate change, and care for our neighbors, ordinary people are already acting with shrewd urgency. Grassroots organizations spring up overnight when disasters strike. Debt forgiveness campaigns emerge over breakfast conversations. Community pantries appear in neighborhoods. Churches quietly help with debt relief.

These folks aren’t waiting for permission or worrying about looking foolish. They’re using whatever power they have to create the world they want to live in, just like the manager.

Shrewd Discipleship

The manager didn’t wait for permission. He didn’t worry about his reputation. He didn’t get paralyzed by the situation’s complexity. He saw what needed to happen and acted with kingdom urgency—as if God’s reign of justice and love were happening right now.

We are invited into that same kind of shrewd discipleship. We’re invited to use our relationships, our resources, and our remaining time here not to preserve our reputation or build personal security, but to build the beloved community that will welcome us all home.

Sometimes the most faithful thing we can do is to act like we are running out of time. Because we are.

And that’s exactly the kind of holy urgency God’s kingdom and our world need right now.

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Here’s what I’m sitting with: What’s one thing you’ve been holding onto—whether it’s money, time, reputation, or comfort—that might need to be “forgiven” or given away to build deeper community? What would shrewd discipleship look like in your life right now?

I’d love to hear your thoughts in the comments. This parable still makes me uncomfortable, and I think that’s exactly the point.