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Why did Amalek position themselves on the border 200 years before the Jews would enter Eretz Yisrael? The Midrash reveals Esav's strategic insight: attack when people are traveling and psychologically vulnerable. Being "baderech" means being emotionally crushed, lacking the security of place, family honor, and wealth that give people strength to fight.
This shiur explores a fascinating Midrash that reveals the strategic depth behind Amalek's attack on the Jewish people. The Midrash explains that Amalek positioned themselves on the border of Eretz Yisrael not spontaneously, but as part of a 200-year plan initiated by their ancestor Esav. Esav commanded his grandson Amalek to position themselves "lekadmon laderech" - to meet the Jews on the road and attack them while traveling. Rabbi Zweig analyzes several compelling questions raised by this Midrash: Why did Esav give this command 200 years in advance? Why did Amalek need to relocate when they could have simply traveled to attack the Jews wherever they were? And most fundamentally, what is the strategic significance of attacking people "baderech" (on the road)?
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