The Anakims had in the course of Joshua’s campaigns in the south been expelled from “this mountain,” i. e. the mountain country round Hebron, but they had only withdrawn to the neighboring cities of Philistia Joshua 11:22. Thence, 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 following.
Related Commentaries of Joshua 14:12
Joshua 14:12
12 Now therefore give me this mountain, whereof the LORD spake in that day; for thou heardest in that day how the Anakims were there, and that the cities were great and fenced: if so be the LORD will be with me, then I shall be able to drive them out, as the LORD said.