Chazal (Midrash Rabbah 1:15) relate that when Klal Yisrael was about to wage war against the descendants of Eisav, Hashem showed Moshe Rabbeinu the mountain where the Avos, Patriarchs, were buried. Moshe understood that the location of the burial place prevented Klal Yisrael from battling Eisav. Apparently, it was in Eisav’s zechus, merit, for honoring Yitzchak Avinu (and by extension Avraham Avinu). This is the meaning of Rav lachem sov es hahar hazeh; “Enough of your circling this mountain.” This means the mountain provides a reason to consider Eisav to be off limits. This was all the result of his Kibbud Av.
Another Midrash (Tanchuma Kedoshim 15) seems to present an additional reason for protecting Eisav from Klal Yisrael. The Midrash notes that Hashem never withheld reward from a person – regardless of his negative spiritual, ethical or moral standing. We see this from Eisav who emitted three tears when he heard that he lost out on his father’s blessings (actually it was only two tears, since the third tear remained welled up in his eye). Chazal imply that Eisav’s tears earned him the reward of good fortune.
Horav A. Henoch Leibowitz, zl, reconciles both Midrashim, suggesting that Eisav’s reward for honoring his father was augmented when he cried three times. It was because Eisav honored his father that he realized the significance of the blessings – which catalyzed his tears upon losing the blessings. Thus, the tears elevate the Kibbud Av, which earned him and his descendants’ protection from the Jews. The Rosh Yeshivah derives a powerful lesson from here. Eisav warranted the blessings due to his extraordinary commitment to the mitzvah of honoring his parents. When he saw that he lost the blessings, he became emotional and emitted three tears. The pain that Eisav expressed over losing the blessings became a source of reward for him, thus elevating his mitzvah of Kibbud Av, which resulted in his passion for the blessings. We see from here that pain derived as a result of a mitzvah magnifies the reward that one receives. It is not just the pain that one experiences while performing the mitzvah that gains him reward, but, even afterwards, pain that is sustained as a result of the mitzvah will gain him reward. Eisav had no idea that he would one day have pain because of his Kibbud Av. The three tears were related to his Kibbud Av, but experienced later; yet, they catalyzed his future reward.
Eisav merited that his land was not invaded by the Jewish army due to his exemplary Kibbud Av. The Midrash (Devarim Rabbah 1:15) quotes Rabban Shimon ben Gamliel who posits that no person showed as much respect to his parents as he did. Nonetheless, said the sage, “My honoring my father paled in comparison to that of Eisav, for I would wear my regular street clothes when I honored my father, while Eisav donned his finery when he approached Yitzchak.” If this is the case, why then did Rabban Shimon ben Gamliel not follow suit and also put on his finery when he served his father? After all, what is right is right. Rather than talk about what he should have done – why did he not do it?
The Rosh Yeshivah asks a similar question concerning Mar Ukva who states (Chullin 105a), “I am worse than my father, like vinegar compared to wine. When my father ate meat, he would not eat cheese until the next day, while I will eat cheese at the next meal. (Obviously, it was after the halachically allotted time of separation between meat and milk. While Mar Ukva’s father waited 24 hours between meat and milk, Mar Ukva would eat the same day at a later meal.) The question is: If Mar Ukva was lauding his father’s behavior, stressing that his father was very devout, why did not Mar Ukva accept upon himself to emulate his father’s devotion and also wait 24 hours between meat and milk?
The Rosh Yeshivah explains this based upon a mussar (ethical character refinement) principle, established by the Slabodka school of mussar. They taught that one should not skip spiritual plateaus to ascend above his actual level. In other words, do not act more religious than you really are, because you will err and think that you belong on this elevated spiritual plane – when, in fact, you are unprepared for its demands. This can bring one to haughtiness by thinking he is better – on a loftier spiritual plane – than others. This does not mean that one should refrain from mitzvah performance; rather, he should not go overboard until he is certain that he belongs, and is prepared to serve, on this level.
Apparently, these two sages were not prepared to go beyond executing the mitzvah in full accordance with halachah. They felt that piety was a step above them.