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Why was Amalek living in the Negev instead of their homeland in Har Seir when the spies arrived? Rashi (רש"י)'s mashal reveals that Amalek had been strategically positioned there for 200 years. This wasn't random hostility but a calculated multi-generational plan orchestrated by Esav to intercept the Jewish people on their return to Israel.
This shiur examines a perplexing detail from Parshas Shelach: why the spies first reported that "Amalek dwells in the south" rather than describing the land itself. Rashi (רש"י) provides a mashal comparing this to a child who was beaten with a strap - when you want to frighten him later, you remind him of that strap. Amalek represented the "strap" that had previously struck the Jewish people. Rabbi Zweig initially questions this mashal, noting that when Amalek attacked at Rephidim, the Jews ultimately defeated them with divine help. How can a defeated enemy serve as a source of fear? The resolution lies in understanding that without Moshe's raised hands providing miraculous intervention, Amalek was actually overpowering the Jewish people. The victory came only through direct divine assistance, not natural military strength. This made Amalek a genuinely frightening adversary - like a child who fears a bully even after his father saved him, because the father might not always be there.
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Parshas Shelach 13:29
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