Specifically, in the first chapter, where the Israelites are poised to enter the Promised Land.

We read, "and the cities to which we will come" (Deuteronomy 1:28). The Sifrei Devarim, a collection of early rabbinic interpretations on Deuteronomy, picks up on this seemingly simple phrase. It asks: what's the point of even saying this? The answer, according to the Sifrei, is that it tells us how to approach conquering these cities – knowing which city to target first and how to approach them strategically. Knowledge is power, even in ancient warfare.

But it’s the next verse, Deuteronomy 1:23, that really gets interesting. It says, "And the thing was good in my eyes." Moses is talking about the decision to send spies into Canaan to scout out the land. It seems like a reasonable plan. Get some intel, know what you're up against.

But here's the kicker: the Sifrei Devarim immediately points out that while it was good in Moses' eyes, it wasn't good in the eyes of God. Ouch.

This raises a huge question. If God didn't approve, why is it even included in Moses's rebuke of the people later on? Why mention something that sounds, on the surface, like a good idea?

The Sifrei offers a brilliant analogy to unpack this. Imagine a man wanting to buy a donkey. He asks the owner, "Will you sell me this donkey?" The owner says, "Yes." Then the buyer asks, "Will you let me try it out first?" Again, the owner readily agrees, even offering to show him how much the donkey can carry on the mountain and in the valley. The owner is being incredibly accommodating!

But, and this is the crucial part, because the owner is too agreeable, too eager to please, the buyer becomes suspicious. There must be something wrong with the donkey if the seller is so willing to let it go and so willing to prove its worth. Instead of going through with the deal, he hands back the money.

And that, says the Sifrei Devarim, is the intent of "the thing was good in my eyes." Moses thought sending spies was a good idea, a sensible precaution. But it revealed a lack of faith in God's promise. It was like "trying out" God, testing His commitment. They were essentially saying, "We trust You, God, but we also want to see for ourselves."

The fact that God seemingly allowed it, didn’t prevent them, made it seem like He was okay with their lack of faith, just like the overly agreeable donkey seller. But it wasn't good. It wasn't the path of complete trust that God desired.

So, what's the takeaway? Sometimes, the easiest path, the one that seems most logical, isn't necessarily the right one. Sometimes, true faith requires us to step forward without needing to "try out" the situation first. It demands that we trust in the promise, even when we can't see the full picture. It’s a powerful reminder that even well-intentioned actions can be rooted in a lack of faith, and that true belief requires a leap, not a test drive.