The ancient Israelites certainly did. As they stood poised to enter the Promised Land, Moses, in the book of Devarim (Deuteronomy), doesn't sugarcoat the challenge.

He tells them, "and you will inherit nations greater and mightier than you." (Deuteronomy 9:1)

Okay, thanks, Moses. Needed that pep talk.

But what does that statement really mean? The Sifrei Devarim, a collection of ancient legal and exegetical teachings on the book of Deuteronomy, digs into this verse, unpacking its layers of meaning.

The Sifrei breaks down the verse: "‘Great’ in stature, and ‘mighty’ in strength. ‘Than you’: You, too, are great and mighty, but they are greater than you." It's not saying the Israelites are weaklings. Rather, it’s about relative strength. R. Eliezer b. Yaakov uses a perfect analogy: it's like saying, "That man is stronger than this one." Both are strong, but one is simply more so.

So, the Israelites aren't pushovers, but they're facing some serious competition. These nations aren't just a little bigger; they're significantly so.

But then comes a slightly puzzling repetition. The text asks, why is it written "and mightier than you (plural)" when it already says "seven nations more numerous and mightier than you (singular)" in Deuteronomy 7:1? What's the difference between the singular "you" and the plural "you"?

The answer is fascinating. It teaches us that even within those seven nations, there was one that stood out. One that was greater and more formidable than the entire nation of Israel. Wow. Think about that for a moment.

As Amos 2:9 puts it, "And I destroyed the Emori from before them whose height was like the height of the cedars and who was strong as the oaks." The Emori, or Amorites, were giants, physically imposing and seemingly invincible. Ginzberg, in Legends of the Jews, echoes this, painting a picture of these colossal figures whose very presence could inspire terror.

So, what are we to take away from this? The Israelites were heading into a situation where they were, objectively, outmatched. Yet, they were commanded to proceed, to trust, and to overcome. It's a powerful reminder that facing seemingly insurmountable obstacles doesn't necessarily mean defeat. Sometimes, it means that something greater is at play. The Israelites had something the other nations didn't: a covenant with God.

And maybe, just maybe, that's a lesson for us too. When we feel outmatched, outgunned, facing giants in our own lives, maybe it's time to remember what we do have. What inner strength, what faith, what connection to something larger than ourselves can we draw upon? Because sometimes, the biggest battles aren't won with brute strength, but with something far more powerful.