Sheshai

Sheshai is one of the three sons of Anak who hold Hebron when Israel arrives at the land. He appears with his brothers Ahiman and Talmai in the spy report, in the conquest narrative, and in the early Judges record of Judah's first campaigns.

The Spy Report at Hebron

The twelve sent into the land go up by the south and reach Hebron, where they encounter the Anakim by name: "And they went up by the South, and came to Hebron; and Ahiman, Sheshai, and Talmai, the sons of Anak, were there. (Now Hebron was built seven years before Zoan in Egypt.)" (Nu 13:22). The trio's presence at Hebron is the report that spreads fear through the camp.

Caleb at Hebron

When Caleb takes the inheritance promised him at Kadesh, the same three names are the ones he removes from the city: "And Caleb drove out from there the three sons of Anak: Sheshai, and Ahiman, and Talmai, the children of Anak" (Jos 15:14). The conquest of Hebron is the conquest of these three.

Judah's Campaign

The Judges-era summary names the same trio in Judah's opening campaign at Hebron: "And Judah went against the Canaanites who dwelt in Hebron (now the name of Hebron formerly was Kiriath-arba); and they struck Sheshai, and Ahiman, and Talmai" (Jdg 1:10). The notice closes the loop opened by the spy report — the men whose presence had once turned the camp back are now defeated at the same city.