Why is it that Yitzchak Avinu, the paradigm of avodas Hashem, originally saw fit to give the brachos to Esav, who, as Chazal teach us, was engaging in constant acts of evil? Furthermore, even if in the eyes of Yitzchak, Esav was worthy of blessing, shouldn’t Yaakov also have been deemed worthy at the same time? Certainly Yitzchak knew that Yaakov was spending his days and nights learning Torah! So why was he seeking only to bless Esav?
One approach is that while Yitzchak Avinu considered both his sons to be virtuous, he viewed them very differently. Esav represented the six weekdays, and spent his time in the fields with the mission to battle and ultimately subjugate the forces of evil. He was in need of a blessing from his father to aid him in this battle.
In contrast, Yitzchak viewed Yaakov — who spent all his time in the beis midrash — as representing Shabbos Kodesh, a day which is the source of all blessings. Totally detached from anything pertaining to iniquity, Yaakov, in the eyes of Yitzchak, wasn’t in need of a blessing.
Rivkah Imeinu saw things differently. She felt that were Esav to be granted the brachos, he wouldn’t use them to subjugate wickedness, but rather to bolster the evil in the world and eradicate the positive, spiritual elements.
She therefore instructed Yaakov to go instead. Yaakov was very fearful, reluctant and unhappy with the idea. Obligated by the mitzvah of kibbud eim, Yaakov obeyed, weeping and against his will. Since Yaakov had no contact with the forces of wickedness, it wasn’t possible for him to overcome any evil desires. But through instructing him to overcome his own preferences and listen to her words, Rivkah was able to gift him the ability to overcome malevolent forces in the future, for himself and his descendants for eternity.
But this wasn’t something that could be possibly be revealed to Yitzchak.
Therefore, Rivkah told Yaakov to don the clothes of Esav, along with foul-smelling pieces of goatskin on his hands and skin. Yitzchak smelled the scent of Gan Eden that came with Yaakov, but he also sensed a bit of the evil smell associated with Esav, which justified the need for a brachah.
Only after Rivkah had made all this possible was Yaakov able to travel to Lavan and spend the next two decades battling and vanquishing the wickedness of Lavan and later fighting with the angel of Esav. For through the efforts of his holy mother, Yaakov now had the ability to fight evil.
But why did Hashem see fit to hide from Yitzchak what Esav was really all about, while revealing it to Rivkah Imeinu?
The Rebbe, Harav Bunim of Peshischa, zy”a, taught that Esav didn’t dress like a coarse peasant; he wore the white clothes of a most righteous individual and said Torah at shalosh seudos…
The evil of Esav was so hidden that even the angels were unaware of it, and neither was Yitzchak Avinu. Like all the other Imahos, Rivka Imeinu was a prophetess, and it was only through nevuah that she learned Esav’s true character.
The question remains, however: Why wasn’t Yitzchak Avinu told this nevuah? In addition, why didn’t Rivkah reveal it to him?
It is because in the highest, loftiest levels in Heaven, the attribute of atzvus — melancholy — is never to be found, only joy and jubilation in the service of Hashem.
In order to be able to bring down a blessing from this lofty sphere, Yitzchak Avinu had to experience true, unmitigated joy. Only if he was under the assumption that both his sons were virtuous would Yitzchak be able to reach the necessary level of simchah to be able to give a brachah from such a lofty level. (Adapted from a teaching of the Shem MiShmuel)
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The Ohr Hachaim Hakadosh gives a very powerful and relevant explanation.
Yitzchak Avinu hoped that granting the brachos to Esav would serve as a conduit for his return to the proper path. Chazal tell us that the tragedy of Dinah was a punishment for Yaakov Avinu’s decision not to allow Dinah to marry Esav, for she might have succeeded in bringing him to righteousness. “Perhaps,” the Ohr Hachaim adds, “it would have worked.”
While Esav is generally perceived as evil incarnate, he was an individual with enormous potential. If he would have used his head to overcome his desires, he could have reached even greater heights than his brother. Tragically, he didn’t, and it was only his head that merited to come to rest in Me’aras Hamachpelah. (According to Kabbalah, with the coming of Moshiach, Esav will merit purification.)
Few would feel that giving brachos is the way to reach a son who has devoted his life to acts of violence and immorality. Yet, from this it would appear that there is no limit to our communal obligation towards our youth, even if, R”l, they have strayed from the proper path. No stone may be left unturned, every obstacle must be removed and the flickering flame of hope never extinguished. In the end it will be clear to all that the efforts were not in vain, for eventually all Hashem’s children will return home.