15:14a

And Caleb drove out from there the three sons of Anak: The clause Caleb drove out from there indicates that Caleb attacked the three sons of Anak and made them leave Hebron.

the three sons of Anak: The Hebrew word that the Berean Standard Bible translates as sons can refer to a group of descendants. In this verse it is likely that the three sons of Anak refers to three tribes of the descendants of Anak.

Here are some other ways to translate this part of the verse:

Caleb forced three tribes of Anak people to leave there
-or-
Caleb attacked the three tribes of Anak people who lived in Hebron and made them leave

15:14b

the descendants of Sheshai, Ahiman, and Talmai, the children of Anak: The names Sheshai, Ahiman, and Talmai refer to three tribes. Anak was their forefather. These tribes are also mentioned in Numbers 13:22 and Judges 1:10.

Here are some other ways to translate this part of the verse:

Those were the tribes of Sheshai, Ahiman and Talmai, all descended from Anak
-or-
These were the descendants of Sheshai, Ahiman and Talmai, who were descended from Anak

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