Jesus once told his disciples an odd parable where he used a dishonest manager as an example of how we should be shrewd with our money. What did he mean? Imagine his disciples Simon (the Zealot) and Matthew (the tax collector) discussing this parable.

“Matthew, you know more about these things than I do. Why did the Master commend the dishonest manager’s shrewdness?”

Simon’s question stung a little, and Matthew’s look said so.

“Oh. I didn’t mean that the way it sounded,” said an embarrassed Simon.

Simon and Matthew were unlikely friends. And they hadn’t liked each other much in the beginning.

Simon had been a zealot with a lethal hatred of the Romans. He had once sworn himself to the sacred cause of driving them out of Israel. But even more than the Romans, Simon loathed Jews who helped the Emperor subjugate and pillage God’s people. Jews like Matthew.

Matthew had collected taxes for Rome — and himself. He had simply seen it as a shrewd and lucrative career move. Prior to Jesus calling him from his booth, Matthew had had zero time for the idealism of foolish zealots like Simon. Theirs was a utopic delusion — a handful of angry Jews taking on Caesar’s legions. It was a death wish, an appointment with a Roman cross.

Now the former zealot and former tax collector were fast friends. Only Jesus could have made that happen.

“What did you mean?” Matthew asked.

“I just meant . . . you used to be . . .”

“A shrewd dishonest manager?”

“I’m not saying you were just like . . .”

“Stop tripping over yourself, Simon,” said Matthew, laying aside the vestiges of his pride. “I was every bit as shrewdly dishonest and worse. I know it. It’s just painful to remember what I used to be. So which master are you saying commended the manager?”

“Well, that’s where I’m confused,” replied Simon. “It almost sounded like Jesus commended the self-protective actions of the manager. But I know that’s not right. How is this corrupt scoundrel supposed to be an example for ‘the sons of light’?”

Matthew smiled and said, “Generosity.”

“Generosity?” said Simon incredulously. “The only thing he was generous with was his master’s money!”

“Exactly. Simon, that’s our Master’s point. The manager used his master’s money to win favor with those who could provide him a place to live when he lost his job.”

“And that’s supposed to be a good thing?” said Simon, confused.

“No, Jesus isn’t saying the man’s dishonesty was good. He’s saying that, as a ‘son of this world,’ the man knew how this world works. He used worldly shrewdness so he wouldn’t be homeless, and even his worldly master appreciated his cunning. Jesus is saying that the ‘sons of light’ need to be at least as shrewd about how the kingdom works.”

“Which is completely different,” said Simon.

“Completely,” agreed Matthew. “But what we do is similar to what the dishonest manager did.”

“You mean we’re generous with our Master’s money.”

“Right.”

Simon thought for a moment. “So, in a sense it’s another way of saying, ‘sell your possessions, and give to the needy’ so that we will have ‘a treasure in the heavens that does not fail’ (Luke 12:33). Shrewd ‘sons of light’ give away ‘unrighteous wealth’ and make friends of God, who is our eternal dwelling (Deuteronomy 33:27).”

“Exactly. That’s the financial shrewdness our Master commends.”

Our heavenly Master has made us all managers of “unrighteous wealth” (Luke 16:9). As John Piper says,

The possession of money in this world is a test run for eternity. Can you pass the test of faithfulness with your money? Do you use it as a means of proving the worth of God and the joy you have in supporting his cause? Or does the way you use it prove that what you really enjoy is things, not God? (“Preparing to Receive Christ”)

These are questions we all must ask ourselves, because Jesus wants us to be shrewd with our money (Luke 16:8–9). Kingdom shrewdness looks like this:

“Fear not, little flock, for it is your Father’s good pleasure to give you the kingdom. Sell your possessions, and give to the needy. Provide yourselves with moneybags that do not grow old, with a treasure in the heavens that does not fail, where no thief approaches and no moth destroys. For where your treasure is, there will your heart be also.” (Luke 12:32–34)