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Verse 14

And the three sons of Anak, Sheshai and Ahiman and Talmai, the children of Anak, were forced out from there by Caleb.

Judg 1:10 : 10 And Caleb went against the Canaanites of Hebron: (now in earlier times Hebron was named Kiriath-arba:) and he put Sheshai and Ahiman and Talmai to the sword.
Judg 1:20 : 20 And they gave Hebron to Caleb, as Moses had said; and he took the land of the three sons of Anak, driving them out from there.
Josh 11:21 : 21 And Joshua came at that time and put an end to the Anakim in the hill-country, in Hebron, in Debir, in Anab, and in all the hill-country of Judah and Israel: Joshua gave them and their towns to the curse.
Num 13:22-23 : 22 They went up into the South and came to Hebron; and Ahiman and Sheshai and Talmai, the children of Anak, were living there. (Now the building of Hebron took place seven years before that of Zoan in Egypt.) 23 And they came to the valley of Eshcol, and cutting down a vine-branch with its grapes, two of them took it on a rod between them; and they took some pomegranates and figs.
Num 13:33 : 33 There we saw those great men, the sons of Anak, offspring of the Nephilim: and we seemed to ourselves no more than insects, and so we seemed to them.
Josh 10:36-37 : 36 And Joshua and all Israel with him went up from Eglon to Hebron, and made an attack on it; 37 And took it, overcoming it and putting it and its king and its towns and every person in it to the sword: as he had done to Eglon, he put them all to death, and gave it up to the curse with every person in it.