Anakim: Defeated by Caleb
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Joshua 14:12, 15
Now therefore give me this hill country that the LORD promised me on that day, for you yourself heard then that the Anakim were there, with great and fortified cities. Perhaps with the LORD’s help I will drive them out, as the LORD has spoken.” / (Hebron used to be called Kiriath-arba, after Arba, the greatest man among the Anakim.) Then the land had rest from war.
Joshua 15:13, 14
According to the LORD’s command to him, Joshua gave Caleb son of Jephunneh a portion among the sons of Judah—Kiriath-arba, that is, Hebron. (Arba was the forefather of Anak.) / And Caleb drove out from there the three sons of Anak—the descendants of Sheshai, Ahiman, and Talmai, the children of Anak.
Judges 1:20
Just as Moses had promised, Judah gave Hebron to Caleb, who drove out the descendants of the three sons of Anak.