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Why does Yaakov send messengers to Esav in Eretz Edom when the parsha later shows Esav still lived in Canaan for another twenty-one years? The shiur resolves this by explaining that Edom was already "Eretz Yisrael" at the Bris Bein HaBesarim—transferred to Avrohom's descendants immediately, though the Jewish people would only settle the seven lands initially. Yaakov thus sent the angels of Eretz Yisrael to divide the inheritance: Canaan for Yaakov, Edom for Esav.
The shiur opens with a textual problem in Parshas Vayishlach. The opening pasuk states that Yaakov sent malachim (either angels or messengers—Rashi (רש"י) translates as angels, Onkelos as messengers) "el Esav achiv artza Se'ir s'dei Edom"—to Esav his brother, to the land of Se'ir, the field of Edom. Yet later in the parsha (perek 36, pasuk 6–7), after Yitzchok's death twenty-one years later, the Torah (תורה) describes Esav leaving Canaan and moving to Eretz Edom "mipenei Yaakov achiv"—because of his brother Yaakov, as their holdings were too large to dwell together. This creates a glaring contradiction: if Esav was still living in Canaan throughout those twenty-one years and only moved to Edom afterward, why does Yaakov send messengers to him in Edom at the beginning of the parsha? Esav's residence and citizenship were in Eretz Yisrael; Edom may have been a vacation home, but not his primary dwelling. Rabbi Zweig addresses Rashi's interpretation that Yaakov sent angels rather than human messengers. Rashi's position is supported by the end of the previous parsha, where the Torah describes Yaakov encountering two camps of angels (Machanayim)—the angels of Chutz La'aretz and the angels of Eretz Yisrael. Normally, these two sets of angels do not remain together; when one group descends, the other ascends. Yet here both camps are present. Rashi explains that the angels of Chutz La'aretz remained because Yaakov would need them to send to Esav in Edom, which is outside Eretz Yisrael proper. This reading ties the two pesukim together and explains why there were two camps of angels at once.
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Bereishis 32:4 (Parshas Vayishlach), Bereishis 15:18 (Bris Bein HaBesarim), Bereishis 36:6-7
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