Eshcol
Eshcol stands in the UPDV at two distinct points: as a personal name in the Abram-narrative of Genesis 14, where he is the Amorite brother of Mamre and Aner and a confederate of Abram in the Chedorlaomer-rescue, and as the place-name of a valley in the hill-country near Hebron, into which Moses' spies climb and out of which they cut the single grape-cluster that becomes the lead sample of the land. The same cluster that gives the valley its name afterward names the spy-ascent that turned the first generation away from entry.
The Amorite Brother of Mamre
In the wake of Chedorlaomer's strike against Sodom, the escaped survivor brings the news to Abram, and the household is fixed by the oaks of Mamre with three Amorite brothers as its standing alliance: "And there came one who had escaped, and told Abram the Hebrew: now he stayed by the oaks of Mamre, the Amorite, brother of Eshcol, and brother of Aner; and these were confederate with Abram" (Gen 14:13). Eshcol is named here as one of three Amorite brothers — Mamre, Eshcol, and Aner — and the verse closes with the confederate-clause that binds the three to Abram before a single sword is drawn.
After the rescue and the Melchizedek-blessing, Abram refuses the king of Sodom's spoil for himself, but he refuses on his own behalf only, and he carves out an exception for the men who marched with him: "except only that which the young men have eaten, and the portion of the men who went with me, Aner, Eshcol, and Mamre. Let them take their portion" (Gen 14:24). The three Amorite confederates are named together a second time, and Abram's refusal of personal spoil is paired with an explicit clause leaving the confederates' portion intact.
The Valley of the Cluster
The second Eshcol is a valley in the hill-country, named for what is taken out of it. When the twelve spies sent from Paran reach its ground, the valley supplies the lead specimen of the land's fruit: "And they came to the valley of Eshcol, and cut down from there a branch with one cluster of grapes, and they bore it on a staff between two; [they brought] also of the pomegranates, and of the figs" (Num 13:23). The coming-verb brings the spies into the valley, the cutting-verb takes the one-cluster branch as object, and the bearing-verb requires a two-man staff-carry, so the cluster is exhibited as heavy enough to need two bearers and the cut branch becomes the lead sample of the land.
The narrator then turns the cluster back into the place-name: "That place was called the valley of Eshcol, because of the cluster which the sons of Israel cut down from there" (Num 13:24). The naming-clause makes the valley's title a memorial of the spy-cluster, so that any later mention of "the valley of Eshcol" carries the cluster with it.
The Spy-Ascent into the Hill-Country
Deuteronomy retraces the same ascent in Moses' first-person review. The spies, sent up at the people's request, climb into the hill-country and reach the valley by name: "and they turned and went up into the hill-country, and came to the valley of Eshcol, and spied it out" (Deut 1:24). The ascent-verb and the came-to-the-valley clause fix Eshcol as the staging-ground for the search of the land; the spied-it-out verb closes the action that began with the people's request.
Eshcol as the Site of Discouragement
Moses cites the same valley a second time, deep in the Transjordan negotiation with the sons of Reuben and Gad, and there the place-name has become shorthand for the spy-failure that turned the first generation back: "For when they went up to the valley of Eshcol, and saw the land, they discouraged the heart of the sons of Israel, that they should not go into the land which Yahweh had given them" (Num 32:9). The going-up verb takes the valley as destination, the seeing-verb fixes the spy-view of the land, and the discouraging-clause turns the sons of Israel away from the Yahweh-given land — so the same valley whose cluster proved the land's fruitfulness is named here as the ascent-site whose returning report broke the people's heart against entry.