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How did the spies find miraculous giant clusters of grapes in Eretz Yisrael when the land was owned by Goyim? The Midrash explains that Eshkol was called by that name 400 years earlier because he was Avrohom's ally. His support enabled Avrohom to spread monotheism, creating a connection to Klal Yisrael that allowed the land to respond even before the Jewish people entered.
The shiur explores a puzzling Midrash on Parshas Shelach that explains why the spies were able to find miraculous fruit in Eretz Yisrael despite the land being inhabited by Goyim. The Midrash states that Eshkol was given his name (meaning 'cluster') 400 years earlier because HaKadosh Baruch Hu foresaw that Jewish spies would take grape clusters from his territory. Rabbi Zweig raises fundamental questions about this teaching. Why should Eshkol be named after an event that would contribute to lashon hara about Eretz Yisrael? The grape clusters were used by the spies to argue that the land was abnormal and dangerous, not to praise it. Furthermore, why name someone after a future event rather than their current merits as Avrohom's loyal ally?
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Parshas Shelach - Nachal Eshkol
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