“And Hebron was given to Caleb just as Moses said. And he dispossessed from there the three sons of Anak.”
From the account in Joshua 15:14, we know the names of these three sons: Sheshai, Ahiman, and Talmai. We also know that these sons of Anak are associated with the Nephilim (Numbers 13:33) and were responsible for the fear that the original spies into the Promised Land had. The cowardly spies referred to them as giants — “we seemed as grasshoppers to them!” (Numbers 13:33). Obviously they were exaggerating to try and place fear into the hearts of the others. It is ironic that it is Caleb (who had warned the people not to fear the sons of Anak 40 years prior) who will defeat them in God’s plan.
What is often misunderstood is that “Nephilim” does not mean “giant,” nor is it a reference to the offspring of fallen angels and men (as some people would read the early verses of Genesis 6. The phrase, “sons of God,” is most commonly a reference to believers in the scriptures and thus Genesis 6 speaks of the line of Seth intermarrying with the line of Cain — a problem seen over and over again in the scriptures.
In Hebrew, the term “Nephilim” means, “those who fall upon others.” The best description of them would be that of marauders — vicious thieves and robbers who fall upon their prey, attack them, and pillage. Such are the makings of a people that have walked away from the teaching and commands of God. Biblical and extra-Biblical history is filled with such people — the Vikings, the Huns, the Nazis, and even Isis today. And much like Caleb did in his day, we must not fear them, but instead stand against their wickedness and defeat their influence while also taking the Gospel of Jesus Christ into their midst, for without Christ there will be no lasting change in the hearts of men.
Thus, the sons of Anak are dispossessed and Caleb settles into their land — all to the glory of God. The sad thing is that as we continue to read this re-telling of the conquest, it becomes more and more apparent that there are many who are not being driven out — and the idols and the pagan customs remain in the land, which will sadly influence the people in generations to come.