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Why did Yaakov send angels—not servants—to Esav, and why was he afraid if those angels could overpower Esav's men? The shiur reads Vayishlach with Rashi (רש"י)'s mehalech: the malach'im were the angels of Eretz Yisrael who had just greeted Yaakov, sent to negotiate from strength. Yaakov's fear was real only until he defeated the sar shel Esav; afterward, his position was secure.
Rabbi Zweig opens with a close reading of the word "vayishlach" in Bereishis 32:4. The root shin-lamed-chet can mean "send away" (severing control) or "send out" (as an agent who reports back). Targum Yonasan ben Uziel translates it here as "shalaḥ" (sent away), not "sheder" (dispatched as an agent), suggesting Yaakov was not expecting a report back—he was simply informing Esav that he was coming. Rashi (רש"י)'s comment on verse 6 ("lehagid ladoni") confirms this: Yaakov's message was not a request ("May I come?") but a declaration ("I am coming"). The word "lefanav" (before him) indicates that Yaakov himself would follow—his agenda was to arrive, not to ask permission. This raises the question: Why did Yaakov send messengers at all? If he was simply announcing his arrival, why not come directly? And why did the messengers return (verse 7) if they were not agents sent to report back? The answer is that the messengers returned only because circumstances changed: they discovered that Esav was not peacefully waiting in Seir but was marching toward Yaakov with four hundred men. Had Esav been where Yaakov thought he was, the messengers would not have returned—they were fulfilling a one-way mission of announcement.
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Bereishis 32:4-8 (Parshas Vayishlach)
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