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Why does Yaakov send messengers to Esav in Seir/Edom when Esav still lives in Canaan and won't move to Edom for another twenty-one years? The shiur argues that Edom is already Eretz Yisrael—promised to Avrohom's descendants in the Bris Bein HaBesarim—and Yaakov sends the angels of Eretz Yisrael to meet Esav on that sacred ground, effectively dividing the inheritance between brothers.
Rabbi Zweig opens the shiur by examining the dual translation of "malachim" in Bereishis 32:4—either messengers or angels. Rashi (רש"י) translates it as angels; Onkelos as messengers. Rabbi Zweig explains that Rashi's reading resolves a textual difficulty: the previous pasuk mentions "Machanayim" (two camps)—one camp of angels from Chutz La'aretz and one from Eretz Yisrael. Ordinarily, these angels do not coexist; when one ascends, the other descends. Yet here both camps remain because Yaakov needs the angels of Chutz La'aretz to send to Esav, who is outside the land. Rashi's reading of "malachim" as angels in the next pasuk explains why both camps are present. The shiur then confronts a chronological puzzle: the pasuk states Yaakov sent messengers "to Esav his brother, to the land of Seir, the field of Edom." Yet according to the later narrative in Vayishlach (Bereishis 36:6-8), Esav does not move to Edom until after Yitzchok's death—twenty-one years after Yaakov's return to Canaan. At the time Yaakov sends these messengers, Esav is still living in Canaan. Why, then, does Yaakov send messengers to Edom rather than to Canaan, where Esav actually resides? The text appears internally inconsistent.
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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.
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Bereishis 32:4, Bereishis 15:18-21, Bereishis 36:6-8
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