Sheshai was one of the three Anakite giants living in Hebron when the Israelites arrived in Canaan. He was a descendant of Anak, and his name is mentioned among the fearsome giants reported by the spies. Sheshai was eventually driven out by Caleb, who conquered Hebron.
When Moses sent twelve spies into the land of Canaan, they came to Hebron where Sheshai, Ahiman, and Talmai, descendants of Anak, lived. The spies reported that they felt like grasshoppers compared to the giants.
22They went up through the Negev and came to Hebron, where Ahiman, Sheshai, and Talmai, the descendants of Anak, lived. (Hebron had been built seven years before Zoan in Egypt.)
23When they reached the Valley of Eshcol, they cut off a branch bearing a single cluster of grapes, and two of them carried it on a pole between them, along with some pomegranates and figs.
33We even saw the Nephilim there—the descendants of Anak come from the Nephilim. In our own eyes we seemed like grasshoppers, and so we seemed to them.
The report about Sheshai and the other Anakites caused great fear among the Israelites, and the people refused to enter the promised land. This led God to condemn that generation to wander in the wilderness for forty years.
2All the Israelites grumbled against Moses and Aaron, and the whole congregation said to them, "If only we had died in Egypt! Or if only we had died in this wilderness!
3Why is the LORD bringing us to this land, only to fall by the sword? Our wives and children will become plunder. Wouldn't it be better for us to go back to Egypt?"
36none except Caleb son of Jephunneh. He shall see it, and to him and his children I will give the land he set his foot on, because he followed the LORD wholeheartedly."
12So give me this hill country the LORD spoke of that day, for you yourself heard then that the Anakites are there, with large fortified cities. It may be that the LORD will be with me, and I will drive them out, just as the LORD said."
14So Hebron has belonged to Caleb son of Jephunneh the Kenizzite as an inheritance to this day, because he followed the LORD, the God of Israel, wholeheartedly.
13To Caleb son of Jephunneh, Joshua gave a portion among the people of Judah, as the LORD had commanded him: Kiriath Arba, that is, Hebron—Arba being the ancestor of Anak.
The tribe of Judah marched against Hebron and defeated Sheshai, Ahiman, and Talmai. This confirmed God's promise that the Israelites would overcome the giants in Canaan.