Yaakov's Fear and Grief: Understanding Relationships, Emes, and Responsibility for Eisav

This shiur analyzes Parshas Vayishlach, focusing on the Torah (תורה)'s description of Yaakov's dual emotional response when confronting Eisav: "Vayira Yaakov meod vayetzar lo"—he was very afraid and very aggrieved. Chazal explain that his fear stemmed from the possibility that Eisav might kill him, while his grief came from the possibility that he might have to kill Eisav. Rabbi Zweig addresses two fundamental questions that the Rishonim raise on this passage. The first question concerns Yaakov's fear. God had explicitly promised Yaakov in the previous parsha, "I will guard you wherever you go and return you to this land; I will not abandon you until I fulfill everything I have said." Given this divine guarantee, why was Yaakov afraid? The Gemara (גמרא) answers that even when God makes a promise, one must be concerned "shema yigrom hachet"—perhaps sin will cause the loss of merit necessary to deserve that promise. This raises a fundamental contradiction that the Rambam (רמב"ם) highlights: Another Gemara states that any statement God makes for good, even if conditional, must be fulfilled. When God told Moshe "I will make you into a great nation" (contingent on destroying the Jewish people after the golden calf), God ultimately fulfilled this promise even though Moshe's intercession prevented the condition from materializing—Moshe's descendants indeed became numerous. How can we reconcile these two principles?