If you fast forward in the Text to 1 Samuel 15, there’s a story about Saul and the Amalekites. He is told to “utterly destroy them” by the Prophet Samuel; Saul refuses, so Samuel has to intervene.
This story is unusually violent if you don’t know the context. The rationale for their annihilation is given in 1 Samuel 15:2: “I will punish Amalek for what he did to Israel, how he set himself against him on the way while he was coming up from Egypt.”
That leads the reader back to Exodus 17, where Amalek fought against Israel at Rephidim. This story is summed up in Deuteronomy 25:17-19, where Moses mentions that Amalek ambushed them along the way and targeted the weaker stragglers near the end of the baggage train. God promises to blot them out from under the sun because of it (Deut. 25:19).
Originally descended from Esau (Genesis 36:16), the nation of Amalek is an ancient and continual enemy to the Israelites. They’ll attack Israel again in the very next chapter (Numbers 14:45), and will continue to do so until the Simeonites finally eradicate the last of them in 1 Chronicles 4:43.
With that in mind, it makes sense that the spies call out the nation of Amalek as “living in the land of the Negev,” as one of the first peoples they encountered during their trek into the land. The Negev is in the southern region of Canaan, which is what gave them such easy access to the wandering Israelites.
While the threat of the Amalekites is large and foreboding, it’s best seen in its context withthe other nations: the Hittites, the Jebusites, the Amorites, and the Canaanites. The conglomeration of these nations—and their geographical markers—gives the impression to Israel that any venture into Canaan will result in them being immediately surrounded.
Which is exactly what happens. In the book of Joshua, when they penetrate into Canaan, they do so by crossing the Jordan River from the east. They cut straight towards Jericho, and the nations to the north and south eventually band together (in their respective regions) in a bid to push back Israel.
That’s the image that the spies brought back to the rest of the people. In their eyes, Canaan was not only fully inhabited by nations that were already used to constant conflict, they were also dealing with multiple cultures that were deeply entrenched in the area. Uprooting them would be a challenge, to put it mildly.
Caleb saw a different path. Instead of seeing people that were entrenched in the land, he saw people that were ripe to be plucked, just like the grapes they carried with them. He saw them as heavy obstacles, to be sure, but none more powerful than His God.
In the end, the spies were right. Physically, they couldn’t match up with the nations that were already there. But Caleb was even more right: The nations couldn’t match up with Jehovah.
