As Ya’akov’s encounter with Eisav draws to a close, Ya’akov tells his brother, “Ya’avor Na Adoni Lifnei Avdo…Ad Asher Avo El Adoni Sei’irah,” “Let my lord (Eisav) go ahead of his servant (Ya’akov)… until I come to my lord at Sei’ir” (BeReishit 33:14). In other words, Eisav should go on to Sei’ir, and Ya’akov will catch up to him there. However, Ya’akov never ends up meeting Eisav at Sei’ir; why did Ya’akov lie to Eisav?
Rashi (ad loc. s.v. Ad Asher Avo El Adoni Sei’irah), quoting the Midrash (BeReishit Rabbah 78:14), explains that during the days of Mashi’ach, Eisav will be judged at Har Sei’ir. This, explains Rashi, is when Ya’akov (meaning the Jewish people) will meet up with Eisav. Rashi also quotes the Gemara (Avodah Zarah 25b), adding that just as Ya’akov told Eisav he would go to Sei’ir, but in the end went only until Sukot, if an idol worshipper questions a Jew as to where he is traveling, the Jew should respond with the name of a place more distant than his actual destination. The implication of this Gemara is that Ya’akov lied in order to protect himself and his family from having another encounter with Eisav.
The Maharsha seems perturbed by Rashi’s explanation. It appears that the Gemara and the Midrash actually contradict each other! The Gemara suggests that Ya’akov lied for his family’s protection, while the Midrash states that Ya’akov was telling the truth, that in the future they will, in fact, meet up in Sei’ir. The Maharsha asks, how can it be that Rashi combined both answers when they are seemingly contradictory?
The Maharsha reconciles the contradictory statements of the Gemara and the Midrash by explaining that Ya’akov gave what he believed to be a false statement when he said that he will meet up with Eisav at Sei’ir. However, since he was such a great person, any statements he made, even false ones, would ultimately be fulfilled. This is why in the future, during the Messianic era, Eisav will stand in judgment at Har Sei’ir – to make Ya’akov’s statement true.
Rav Menachem Mendel Schneerson of Lubavitch writes in his Sefer Torat Menachem that there is a major difficulty with the Maharsha’s answer. He writes that it is very hard to understand because the Midrash states that we should do exactly as Ya’akov did. How is that possible? Ya’akov told a “truthful lie,” ultimately fulfilled only because of his greatness. How can we, if placed in that situation, expect that our lie will come true with time? Furthermore, based on the Pesukim alone, Eisav didn’t seem to show any animosity toward Ya’akov, so what motivation was there for him to lie at all? We must instead conclude that Ya’akov did, in fact, tell the truth, and he told it at a level that an average person can emulate. If this is so, we still must reconcile this with the fact that Ya’akov did not go to Sei’ir, but went only to Sukot. Rav Schneerson explains that Rashi writes that Ya’akov was “Hirchiv,” literally, “broadened,” his journey, implying that it was delayed. Taking into account this interpretation, we can now understand Rashi and how Ya’akov never did lie: Ya’akov was saying that his journey to Sei’ir would be delayed until the time of Mashiach.