See the marginal references.

The three sons of Anak - See on Joshua 14:15 (note).

And Caleb drove thence the three sons of Anak,.... Some think this was after the death of Joshua, and is here inserted by some other person divinely inspired, and thoroughly acquainted with this fact, that the gift and the possession of this place might appear in one view; but it rather seems to be done before:

Sheshai, and Ahiman, and Talmai, the children of Anak; the very same giants Caleb saw at Hebron, when he was sent a spy into the land, Numbers 13:22; for these may as well be supposed to have lived to this time as himself, unless it can be thought that they were the sons of those men, called by their fathers' names; and though they were driven out when Joshua took Hebron, yet while he was engaged in making other conquests, or however before he died, they regained the possession of that city, and of the parts adjacent to it, from whence Caleb, with the help of his tribe, expelled them, conquered, and slew them, Judges 1:10.

Thence, i.e., out of Hebron, Caleb drove (ויּרשׁ, i.e., rooted out: cf. יכּוּ, Judges 1:10) the three sons of Anak, i.e., families of the Anakites, whom the spies that were sent out from Kadesh had already found there (Numbers 13:22). Instead of Caleb, we find the sons of Judah (Judaeans) generally mentioned in Judges 1:10 as the persons who drove out the Anakites, according to the plan of the history in that book, to describe the conflicts in which the several tribes engaged with the Canaanites. But the one does not preclude the other. Caleb did not take Hebron as an individual, but as the head of a family of Judaeans, and with their assistance. Nor is there any discrepancy between this account and the fact stated in Joshua 11:21-22, that Joshua had already conquered Hebron, Debir, and all the towns of that neighbourhood, and had driven out the Anakites from the mountains of Judah, and forced them back into the towns of the Philistines, as Knobel fancies. For that expulsion did not preclude the possibility of the Anakites and Canaanites returning to their former abodes, and taking possession of the towns again, when the Israelitish army had withdrawn and was engaged in the war with the Canaanites of the north; so that when the different tribes were about to settle in the towns and districts allotted to them, they were obliged to proceed once more to drive out or exterminate the Anakites and Canaanites who had forced their way in again (see the remarks on Joshua 10:38-39, p. 86, note).

And Caleb {e} drove thence the three sons of Anak, Sheshai, and Ahiman, and Talmai, the children of Anak.

(e) This was done after the death of Joshua, Jud 1:10,20.

15:14 Drove thence - That is, from the said territory, from their caves and forts in it. These giants having either recovered their cities, or defended themselves in the mountains. Three sons of Anak - Either the same who are mentioned, Numb 13:33, and so they were long - lived men, such as mainly were in those times and places: or their sons, called by their father's names, which is very usual.

14. drove thence the three sons of Anak-rather three chiefs of the Anakim race. This exploit is recorded to the honor of Caleb, as the success of it was the reward of his trust in God.

15:13-19 Achsah obtained some land by Caleb's free grant. He gave her a south land. Land indeed, but a south land, dry and apt to be parched. She obtained more, on her request, and he gave the upper and the nether springs. Those who understand it but of one field, watered both with the rain of heaven, and the springs that issued out of the earth, countenance the allusion commonly made to this, when we pray for spiritual and heavenly blessings which relate to our souls, as blessings of the upper springs, and those which relate to the body and the life that now is, as blessings of the nether springs. All the blessings, both of the upper and the nether springs, belong to the children of God. As related to Christ, they have them freely given of the Father, for the lot of their inheritance.