There still were Canaanite peoples who lived in the valleys and they had iron chariots. Judah was unable to drive them out and capture their lands. Caleb, the confident vocal leader of Judah, was able to secure Hebron as his personal inheritance as Moses promised.
Caleb defeated three prominent sons of Anakim. Just as Judah was unable to fully drive everyone out of the valley, the children of Benjamin also didn’t fully drive out the Jebusites who were living in Jerusalem.
In the end, Israel did not get rid of all the Canaanites who lived in Gezer, Kitron, and Nahalol. The most they were able to do was to put those people under them in servitude. The Amorites forced the tribe of Dan to stay in the mountains and they controlled the valley.
Caleb Defeated Three Prominent Sons of Anakim
They also secured Mount Heres, but the house of Joseph finally grew strong enough to prevail over the Amorites and made them tributaries. The Amorites were able to keep the lands from Akrabbim to Sela, up to the higher places.
After the death of Joshua, the children of Israel began to move away from the God of Israel. The following generation did not even know the LORD or any of the things the LORD had done for Israel.
This angered the LORD greatly and thus God allowed other nations to invade Israel and take their possessions. The LORD allowed Israel to face oppression from their surrounding enemies until they returned to HIM.
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