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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’?”

Written by Jon Bloom
Read more at Desiring God

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