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Why does the Midrash say Yaakov's hand grasping Esav's heel caused Avrohom Avinu such grief? The shiur develops a fundamental distinction: Avrohom sought to be "father of nations," creating an independent Jewish infrastructure, while Yaakov's approach means Jews take leadership within the goy's pre-existing political system. This explains both historical patterns of antisemitism and why Esav specifically resents Jewish presence in Western civilization.
The shiur opens with a perplexing Midrash discussing the pasuk describing Yaakov's birth with his hand grasping Esav's heel. When asked who will rule after Rome, the Roman emperor is shown a written answer referencing this verse. The Midrash states this caused "tzaras hatzaddik" (the grief of the righteous one). The Yefei Toar suggests this refers to Yaakov's suffering, but Rabbi Zweig challenges this interpretation on multiple grounds: Why would showing a pasuk require writing on paper? What is the nature of the "tzara" mentioned? Rabbi Zweig proposes that "oto tzaddik" refers not to Yaakov but to Avrohom Avinu, a usage found explicitly in Gemara (גמרא) Berachos 10a regarding the phrase "shelo yomar oto tzaddik." This reframes the entire discussion. The fundamental insight is that "v'yado ochezes b'akeiv Esav" (his hand grasping Esav's heel) means the Jew doesn't create his own independent political infrastructure when dealing with Esav/Rome, but rather gets pulled along in the wake of the goy, taking over leadership within the pre-existing system that Esav established.
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Why does the Midrash connect Pharaoh's expulsion of the Jews to the mitzvah of shiluach hakan? The shiur develops a chiddush that Pharaoh's sin wasn't only drowning the children, but the insensitivity of expelling the parents afterward. The deeper analysis reveals that Pharaoh may have valued the Jews greatly and wanted to control them—making his expulsion an act of tremendous cruelty, not liberation.
Why does Moshe respond to the splitting of the sea with shirah rather than praise or thanksgiving? Rashi's use of "al libo" reveals that shirah is an emotional expression—a response of love to love. When Hashem shows personal care, the only adequate response is "I love You too," not mere gratitude or praise, and this principle applies to all relationships.
Bereishis 25:26
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