Sheshai

Sheshai (meaning: whitish or six) was one of the three sons of Anak — the gigantic pre-Israelite inhabitants of the hill country of Canaan — encountered by the Israelite spies at Hebron during the wilderness reconnaissance (Numbers 13:22). The three sons of Anak named are Sheshai, Ahiman, and Talmai, and their stature contributed to the fearful report of the ten faithless spies, who said Israel was like grasshoppers compared to these men (Numbers 13:33).

Sheshai and his brothers were eventually expelled from Hebron by Caleb, who at eighty-five years old claimed the hill country as his inheritance and drove out the three Anakites (Joshua 15:14; Judges 1:10). Their defeat at Caleb's hand vindicates Joshua's minority report from forty-five years earlier that the land could be taken with God's help, and it demonstrates that the very enemies whose size had caused ten spies to despair were entirely within the capability of a man walking in faith.