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Verse 14

Caleb drove out the three sons of Anak: Sheshai, and Ahiman, and Talmai, the children of Anak.

Judg 1:10 : 10 Judah went against the Canaanites who lived in Hebron (now the name of Hebron before was Kiriath Arba); and they struck Sheshai, and Ahiman, and Talmai.
Judg 1:20 : 20 They gave Hebron to Caleb, as Moses had spoken: and he drove out there the three sons of Anak.
Josh 11:21 : 21 Joshua came at that time, and cut off the Anakim from the hill country, from Hebron, from Debir, from Anab, and from all the hill country of Judah, and from all the hill country of Israel: Joshua utterly destroyed them with their cities.
Num 13:22-23 : 22 They went up by the South, and came to Hebron; and Ahiman, Sheshai, and Talmai, the children of Anak, were there. (Now Hebron was built seven years before Zoan in Egypt.) 23 They came to the valley of Eshcol, and cut down from there a branch with one cluster of grapes, and they bore it on a staff between two; [they brought] also of the pomegranates, and of the figs.
Num 13:33 : 33 There we saw the Nephilim, the sons of Anak, who come of the Nephilim: and we were in our own sight as grasshoppers, and so we were in their sight."
Josh 10:36-37 : 36 Joshua went up from Eglon, and all Israel with him, to Hebron; and they fought against it. 37 They took it, and struck it with the edge of the sword, with its king and all its cities, and all the souls who were in it. He left none remaining, according to all that he had done to Eglon; but he utterly destroyed it, and all the souls who were in it.