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Why did the spies mention Amalek first when describing the inhabitants of Eretz Yisroel? The Midrash compares this to reminding someone of a painful punishment. The shiur develops the paradox that Amalek both won and lost their war with Israel, resolving it through understanding the two-day battle structure.
This shiur explores a Midrash analyzing why the spies mentioned "Amalek yoshev be'eretz HaNegev" when reporting on the inhabitants of Eretz Yisroel. The Midrash offers a mashal of a child who misbehaved and was punished with a strap - when you want to frighten him again, you remind him of that strap. Similarly, mentioning Amalek was meant to instill fear in Bnei Yisroel by reminding them of their previous encounter. The Midrash also explains that Amalek was positioned on the border because Eisav, their grandfather, had instructed them to "catch them on the road" (lekadman laderech). This strategic positioning was designed to attack Klal Yisroel while they were traveling and vulnerable, rather than when they were settled in their own territory.
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Parshas Shelach - Amalek yoshev be'eretz HaNegev
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