Lives of Scripture

Sheshai was one of three sons of Anak -- along with Ahiman and Talmai -- living in Hebron when Moses sent twelve spies to scout the land of Canaan (Numbers 13:22). The spies' report of what they had seen, including "the descendants of Anak," terrified the ten who gave the majority report: "There we saw the Nephilim... and we became like grasshoppers in our own sight, and so we were in their sight" (13:33). That fear, despite Joshua and Caleb's minority report urging Israel to trust God and take the land, led directly to Israel's forty years of wandering as judgment for unbelief (14:1-35). Decades later, when Israel finally entered Canaan under Joshua, Caleb -- then eighty-five years old -- asked for Hebron as his inheritance, specifically because the Anakim lived there and he trusted God's earlier promise that he would drive them out (Joshua 14:6-14). Joshua 15:14 records the fulfillment: "Caleb drove out from there the three sons of Anak: Sheshai and Ahiman and Talmai, the children of Anak." Sheshai's story spans two generations of Israel's history -- first as the reason a whole nation refused to trust God, and finally as proof that the promise Caleb held onto for decades was not wasted.