The Trouble with Jesus

by Constance Hastings

Business Smarts
September 16, 2025

The Trouble with Jesus: He will use whatever he can, even stories from the shady side of life, to get people to understand what God desires for the world. 


Jesus, so much about you is contradictory. You set high moral standards in loving others and God, and still seem to favor people who live in the dirt, lost ones you call them. You teach we should help these people that no one else wants, while you tell the rich to divest of all they’ve got for those who haven’t anything. Wouldn’t that leave everyone in the same sinking boat? You tell us to hate those closest to us in favor for complete devotion to God. All of this is like shooting surgical knives into the soul and taking away what makes the heart beat.


Not so. Yes, adjustments are required. Jesus asks for a reorganization of priorities. His story of the shrewd manager comes from another direction. True, at first reading, it may not seem to meet the mold of the high and holy. But it does get your attention.


Ripping Off the Boss

A rich man (who else, right?) finds out his manager had been stealing from him. The boss tells him to get his final account together because he’s going to get canned. With that prospect, the manager does some quick thinking. Physical labor was not a recourse, nor did he relish begging, so he had to get creative.


Now, here’s the clever thing. He calls in his boss’ debtors. One owed eight hundred gallons of olive oil. The manager reduced it to half that amount. Another owed a thousand bushels of wheat. That bill was reduced to eight hundred.


When the rich man hears about it, he actually admired what the guy did. Jesus’ commentary surprisingly is likewise; “And it is true that the citizens of this world are more shrewd than the godly are.”


Workplace Corruption

So Jesus thinks this arrangement, actually cheating his boss even more, is a good idea? Seems like Jesus is getting a little shady here. And why would the rich boss think he was so clever and smart for doing so?


Try coming at this story from another perspective. Yes, the guy was a cheat and a thief. His business practices were not on the up and up. Today, the IRS would be all over it. At any rate, he did get caught, and he’s getting fired because of it. It’s the consequence for his choice.


Jesus doesn’t come down on him for being a bad person. In this guy’s world, he’s only there to get the best deal for himself. He doesn’t have the capacity to think anybody else would have done differently. His sociopathic tendency can’t conceive it; moral empathy isn’t in his wheelhouse. He just does what’s smart in his own situation.


What the shrewd manager realized, albeit not how most people come to this understanding, is he needed some friends and really fast. He needed them to be on his side, to take care of him, ones who’d be loyal to him because he had sided with them in their need. So he did that for which he’d soon be able to call in his favors. He made friends. Now Jesus says he seems to have figured it out better than “the godly” people. It’s another slam. Are you getting this now?


Christ, but you are good at this. So the manager was the original “make friends and influence people” proponent. Wealth in the end is temporary, whether earned honestly or not. It’s not going to last, even if you die with boats and boatloads of it. But relationships, friendships are better than piles of gold. Your people, the ones with whom you’ve shared and shared life, the ones who will have your back because they know you’ve had theirs, will last.


Precisely. “Use your worldly resources to benefit others and make friends.” That point has already been made. But take note of how far it will go. “In this way, your generosity stores up a reward for you in heaven.” God takes note on how we live.  And if relationships with people are vital, even more so is one’s relationship with God. Money is a big bad distraction from that.


 “You cannot serve both God and money.”

God wants your focus, devotion, love above all else. For Jesus, money, wealth, possessions were illustrative of how that does or does not happen. He knew the hold it had on his listeners as much as it does on people today. Teaching like this speaks where people live.


Time and time again, Jesus preached and taught about this topic.  He paired a story about a lost sheep with a lost coin.  Losing livestock is one thing, but everyone can relate to losing money. Contractors know the risk in investments.  “Count the cost,” he said. Dishonest employees who cook the books are a big business worry. People have strong opinions about it.


Make the Connection

“Unless your are faithful in small matters, you won’t be faithful in large ones.”


If people were as concerned about their relationships with God and neighbor as they were about their bank accounts and financial portfolios…? Answer that one on your own.


Luke 16:1-13


Named 2024 Notable Book Award by Southern Christian Writers Conference!

The Trouble with Jesus: Considerations Before You Walk Away by Constance Hastings

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