Albert Barnes Commentary Joshua 14:12

"Now therefore give me this hill-country, whereof Jehovah spake in that day; for thou heardest in that day how the Anakim were there, and cities great and fortified: it may be that Jehovah will be with me, and I shall drive them out, as Jehovah spake." — Joshua 14:12 (ASV)

The Anakims had in the course of Joshua’s campaigns in the south been expelled from “this mountain,” that is, the mountain country around Hebron, but they had only withdrawn to the neighboring cities of Philistia (Joshua 11:22). From there, they had, as must be inferred from the text here, returned and reoccupied Hebron, probably when Joshua and the main force of the Israelites had marched northward to deal with Jabin and his confederates. Caleb finally drove out this formidable race and occupied Hebron and its dependent towns and district permanently. See (Joshua 15:13 and following).