I realize that Eisov was a rasha, but did he have a chance at all to be legitimate?
The parsha of Eisov is an extremely complex one. His head was buried in the Meoras Hamachpeilah, which would imply that he had some sense of legitimacy. Yet, he personified evil and existed as a total opposite to the kedushah of his younger brother, Yaakov. In your question, you focused on whether he “had a chance.”
The posuk in Parshas Toldos states, “Yitzchok loved Eisov.” The ahavah that Yitzchok felt for Eisov was due to his attempt to be mekareiv Eisov. The Maharal in Gur Aryeh writes awesome words with regard to the spiritual dimension of Eisov. He bases his remarks upon the Chazal that when Rivkah passed a house of avodah zarah, Eisov attempted to emerge.
The posuk in Parshas Noach states, “I will not continue to curse the ground, because the inclination of man’s heart is evil from his youth (ki yeitzer lev ha’adam ra mine’urav).” Rashi explains that the word “mine’urav” refers to youth, but specifically stems from a word implying “slithering out.” Indeed, the yeitzer hara only enters a person at the point that he emerges from his mother and enters the world.
The Maharal, based upon this point, wonders about the fetus of Eisov, who, at that point, had no yeitzer hara, yet he wanted to emerge to serve avodah zarah. The Maharal explains that while Eisov at that point lacked a yeitzer hara, he wasn’t merely one who had an inkling towards evil. Rather, he was one who was composed of pure evil. The yeitzer hara only enters a person after birth, but Eisov’s connection was part of his identity and being. Thus, even though he technically lacked an evil inclination, he strived to follow evil as a mere fetus, for that was the essence of his being. His avodah was to overcome his evil nature. He was supposed to negate himself to serve his younger brother and thereby become a cheilek of Klal Yisroel and realize his spiritual destiny.
Seforim explain that within the initial blueprint of Klal Yisroel, the relationship between Yaakov and Eisov was to be similar to the relationship between Yissochor and Zevulun. Zevulun, in a sense, provides the needs for Yissochor’s capacity to learn Torah and in that way could be considered as one who serves him. Eisov was to be the shomeres hapri, the protector and shell of Yaakov, who represented the fruit and true purpose. Had Eisov acted accordingly, he would have accomplished his spiritual task and had a place within the Jewish nation. But he didn’t and thus forfeited his ability to be a part of Klal Yisroel.
There are two instances where Chazal seem to say that Yaakov should have done more to save Eisov. When Eisov met Yaakov’s family in Parshas Vayishlach, his daughter, Dinah, was hidden by Yaakov so that the evil Eisov wouldn’t cast his eyes upon her and wish to marry her. Chazal say that because of this, Dinah was taken by Shechem. Chazal add that had she indeed married Eisov, perhaps she could have brought him back to serve his Creator. It definitely seems that Eisov had a chance to overcome his sense of evil. Dinah was subject to a major tragedy. It would seem that something positive could have resulted had Eisov met Dinah.
There is a Medrash Tanchumah that states an amazing point. The posuk in Parshas Vayeitzei discusses Yaakov fleeing from Eisov and his subsequent exile from his father and the land of Eretz Yisroel. Chazal state that Yaakov had actually gone into golus, similar to one who kills another beshogeig, unintentionally, and is forced to go into exile in the arei miklat, the cities of refuge. Yaakov was guilty of spiritually killing Eisov, albeit beshogeig, through what transpired with the brachos of Yitzchok in Parshas Toldos.
These words of Chazal seem to imply that Eisov was someone who might have “made it,” even though his basic identity and nature of spirituality was pure evil.
Therefore, to answer your question, it would seem from the words of Chazal that Eisov did have a chance, but through his faulty bechirah, he condemned himself to be totally removed from the destiny of Klal Yisroel.
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