As the start of our sedra attests to, Yaakov sent messengers to Eisav ahead of the grand reunion; to placate Eisav in the hope that Eisav would not fight. Rashi (32:4) tells us that these messengers were actually angels – which begs the question: why did Yaakov not send human messengers? One answer is that Yaakov was trying to be mekarev his twin brother. Yaakov hoped that seeing the spiritual faces of these angels would make Eisav change his ways and repent. Indeed, this is not the first time Yaakov tries to get his brother to mend his ways. One reason why Yaakov was constantly kicking out in the womb whenever Rivkah passed a Shul/Beis Midrash was not for himself (Yaakov was learning Torah with an angel in the womb), but for Eisav – for Eisav to be born in such a place of kedusha and to be influenced by it. Similarly, as Rav Chaim Halpern points out, this was why Yaakov initially planned for Eisav to marry Leah – again, in the hope that Leah would cause Eisav to repent…
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