OU TORAH Vayishlach / Chanukah By Rav Moshe Twersky, HY"D

Rashi explains that Yaakov was not just hopeful that, in the event Eisav would smite the first encampment, the second encampment would survive, but he was confident of that fact because Yaakov planned, “I will fight against him”. What was the guarantee, though? Yaakov put a days’-travel space between the two encampments. Why? Back in parshas Toldos, Rivkah told Yaakov to flee, and added, “Why should I lose both of you on the same day?” In other words, Rashi explains there, if Eisav will try to kill Yaakov, Yaakov would kill him first, and then Eisav’s sons would kill Yaakov. The underlying message, though, of her words is that she knew b’ruach ha’kodesh that Yaakov and Eisav would die on the same day. Therefore, reasoned Yaakov, if I will fight against Eisav and he will manage to kill me, that means he too will die on that day, and he therefore will not have an opportunity to wipe out the other encampment which is a day’s distance away. In fact, Chazal tell us that Eisav lived longer than Yaakov. Yaakov was only brought to Mearas HaMachpeilah months after he died. When Eisav challenged his entry, Chushim ben Dan drew his sword and chopped off Eisav’s head. So, really, Rivkah’s nevuah was not going on the day of their respective deaths, but was in reference to the same day of burial. (From Rebbetzin Twersky)