"When Eisav heard his father's words, he let out a most loud and bitter scream" (27:34).
Our Sages, sensitive to even minor failings in our biblical heroes, saw a parallel between this verse and one appearing well over a thousand years later. "And he (Mordechai) let out a loud a bitter scream" (Esther 4:1). The conclusion they drew from this use of language was that the pain and suffering Yaakov caused Eisav would have repercussions for Yaakov's descendants, who would suffer in their turn under Persian rule. Our actions, for better or worse, do ultimately bear consequences.
The Netziv questions this midrash, not for its suggestion of vicarious punishment, but on its definition of Yaakov's sin. If Yaakov or his future offspring were to be punished the pain he caused, it should be the pain of Yitzchak, not Eisav, for which Yaakov is culpable.
Was not Yaakov, by lying to his father, the cause of "Isaac was seized with a violent fit of trembling" (27:33)? While one might argue that Yaakov was justified in his treatment of Eisav, our rabbis saw it quite differently. Yet they seem to have seen nothing wrong with the fact that Yaakov caused much pain and anguish to his father. How strange! Was not Eisav a sinner, who had, in any case, sold the birthright to his brother? Was not Yaakov justified in his actions towards Eisav?
The Netziv explains that Yaakov's behaviour falls under the category of Aveirah Lishma, sinning for the sake of G-d. In limited circumstances, our rabbis teach that one may-or should we say, must-sin for some noble goal with pure intent. In these situations, our rabbis go so far as to say that such a sin is greater that a mitzvah done lethargically. Yes, Yaakov lied and deceived, but in his unique circumstances, these actions were not only justifiable but laudatory. Yaakov had a moral dilemma: he had to choose between truth, and loyalty to his mother who embodied the ultimate truth of his mission. He was troubled by the knowledge that obeying his mother would cause pain to his father; he did so only because this sin was truly for the sake of heaven.
However, the Netziv explains that Yaakov had no such misgivings or tremors of guilt in seeing Eisav suffer. He may have even felt a little joy by getting even with his undeserving brother. Thus, his deceit toward Eisav was no sin for the sake of heaven. He caused him pain and felt no remorse in doing so. And for this, he was to be punished. Eisav's sins and faults were irrelevant in this context. We must feel the pain even of those who do not feel our pain.
It is worth noting that our custom to blow the shofar 100 times is based on a rabbinic teaching that the mother of Sisrah cried 100 tears. The pain of our enemy's mother is real, even though we must fight her offspring. But we must eradicate evil to purify the world, not to get even with those whom we despise, even if they are despicable. This is a spiritual level that is hard to attain, and not even Yaakov could fully achieve it.
All of us, especially those of us in positions of leadership, must make decisions that potentially cause pain to many. There is no other way to lead: leadership means making difficult decisions. This is fine, provided our motives are for the sake of heaven, to improve our relations with G-d and man. But if our motivation is to increase our business contacts, or to get back at somebody, or to attain personal glory, then we must bear the guilt of the untold suffering we cause. It for this reason that Judaism attaches so much importance to the concept that those engaged in tzarchei tzibur -rabbis, politicians, and community lay leaders, for example-do so B'Emunah, faithfully. If a leader cannot meet this standard, it really is time to move on.
The Netziv understands that those whose public actions are motivated primarily by personal gain fall under the Talmudic category of those of whom it is said, "it would have been better had they not been created". Yaakov was punished for smiling as Eisav got what he deserved, a minor infraction indeed. While there are few, if any, Eisavs in the Jewish community, at times we must cause people pain. But we must ensure that doing so is very painful for us. Deriving pleasure from the pain of others is something that could affect the Jewish people for thousands of years to come.