Introduction: Destiny for Sale
The divergence between Esav and Yaakov doesn’t even wait for “Day One” to express itself. Already in the womb, Esav clamors to get out when Rivka walks by a place of idol-worship. He comes out of the womb blood-red and grows up to pursue a path of violence and vice. His antagonism and enmity towards Yaakov ultimately become formulated in a “halachah” of their own which states: “Esav hates Yaakov.” It is a halachah that Esav’s descendants and spiritual heirs have fulfilled punctiliously throughout the ages, often adding their own embellishments.
It is very easy to survey all this and never ask if things could have been any different for Esav; in other words, to consider whether or not he was effectively doomed from the start to become the wicked person that he did. It should only take a moment’s reflection to recognize that if everyone has free-will, then so did Esav. Indeed, were this not the case and he had no choice but to follow a path of wickedness, he could not then be faulted or indicted for doing so. Apart from this, we consider the fact that only was he the son of both Yitzchak and Rivka, he was at least part of the answer to years of heartfelt prayer on their part. Additionally, numerous lofty individuals were counted among his progeny, including the righteous Antoninus and the Tanna R’ Meir.
What all this means is that although Esav undoubtedly had deeply embedded tendencies towards violence and wrongdoing, he also has the capacity to overcome and control them, channeling them toward productive purposes. As the sages point out, a later personality in Tanach who receives exactly the same appellation as Esav – “אדמוני (ruddy)” was David Hamelech, who used those very qualities to wage war against the enemies of Israel. In other words, while there is no question that Esav’s character was vastly different from that of Yaakov, this only means that his challenges and possibilities were likewise very different, but no less noble or praiseworthy.
Indeed, it was with this in mind that Yitzchak desired to give the blessings to Esav. If we look at the contents of the blessings, they appear to be simply an abundance of material prosperity – מִטַּל הַשָּׁמַיִם וּמִשְׁמַנֵּי הָאָרֶץ – from the dew of the heavens and the fat of the land etc. How do these things form the contents of the coveted blessing of Yitzchak? What is even more puzzling is that, at the end of the parsha, even after Yaakov has received the blessings and Esav asks his father if there is any blessing left for him, Yitzchak responds by essentially blessing him with exactly the same things – מִשְׁמַנֵּי הָאָרֶץ יִהְיֶה מוֹשָׁבֶךָ וּמִטַּל הַשָּׁמַיִם מֵעָל – of the fat of the land shall be your dwelling and of the dew of the heavens from above! Were those not the very things with which he had already blessed Yaakov?
The key difference between these two blessings is the way the original blessing begins: “וְיִתֶּן לְךָ הָאֱלֹקִים מִטַּל הַשָּׁמַיִם – And God shall give you from the dew of the heavens etc.” The blessing lies not in the material assets themselves, but in the way that they come to the person – directly from Hashem. With the recipient of these things mindful of Hashem as their Bestower, the sense of connection that ensues will remind and exhort him toward using them in the service of Godly pursuits.
This was Yitzchak’s plan to provide Esav with the basis for channeling his physical tendencies towards moral and spiritual living. Unfortunately, what Esav had been concealing from Yitzchak over the course of all those years was the fact that he had long since abdicated any notion of doing so, embracing rather a life of temporal and material enjoyment. This is something that Rivka sees much more clearly than Yitzchak, leading her to conclude that if Esav receives the blessings he will only squander and abuse them, and therefore it is Yaakov who should be the one who receives them.
More specifically, Rivka sees not only the lifestyle that Esav has chosen, but that he has adopted an attitude which effectively guarantees that he will never develop any good that is inside of him…
Groomed to Perfection
As a prelude to the chapter which deals with the blessings, the Torah relates the following:
וַיְהִי עֵשָׂו בֶּן אַרְבָּעִים שָׁנָה וַיִּקַּח אִשָּׁה אֶת יְהוּדִית בַּת בְּאֵרִי הַחִתִּי וְאֶת בָּשְׂמַת בַּת אֵילֹן הַחִתִּי
And Esav was forty years old, he took a wife Yehudis the daughter of Beeri the Hittite, and Bosmas the daughter of Elon the Hittite.
It is noteworthy that the verse sees fit to inform us of exactly how old Esav was when he got married. Rashi comments:
Esav was compared to a pig… when the pig crouches down it stretches out its hooves to say, “See, I am pure!”… For forty years Esav had been snatching women from their husbands and violating them. Now, when he became forty, he said, “My father married at forty, I will do likewise.”
We see that the only area of kosherness in which Esav invests is that of appearing kosher, something we have witnessed in his ongoing charade before his father. Not only does this emphasis divert all of his spiritual energy away from actually being or becoming kosher, it effectively seals the path which would allow him to do so. There is only so long Esav can grant exclusive focus to convincing people that he is a moral person before he himself comes to believe it. In this regard, Esav is both the perpetrator and the victim of his deceit. Once he fully believes that he is as kosher as he looks, any introspection with a view to self-improvement is practically impossible – for why spend time developing a product that is already perfect?
Rivka notes this fatal flaw, because she has seen it before. It was a trademark of the master of appearances with whom she grew up – her brother, Lavan. Time and again, we see that Lavan can perpetrate any crime and then not only defend it, but assume the moral high ground when doing so. After agreeing to give Rachel to Yaakov for seven years’ work and then substituting Leah at the last moment, when confronted by Yaakov the next day, Lavan simply answers: “We do not act that way in this place, to give the younger [sister] before the older one.” Just like that! Lavan is saying to Yaakov: “I know you specified Rachel in your terms, but that is immoral and insensitive. I was sure you we not actually asking me to be involved in an immoral enterprise. Were you? Yaakov, I will say that I am disappointed in you. I hope you won’t let me down again. You may now marry Rachel – for another seven years’ work, naturally. Please try and be a good husband, and I hope we never have to speak of this business again.”
Likewise, when Lavan chases after Yaakov to kill him at the end of Parshas Vayetzei, which he is prevented from doing, he explains the background to his pursuit as the fact that Yaakov ran away and did not give him a chance kiss his daughters and grandchildren goodbye!
For people like Lavan and his spiritual heir, Esav, introspection and self-improvement are simply unfathomable. Recognizing this quality in Esav only too well, Rivka realizes that for him to receive the blessings cannot have a good outcome and will only lead to more wickedness on his part.
Wedded to Failure
This disposition of Esav receives tragic expression in another of his weddings, this one at the very end of the parsha. After Yaakov succeeded in receiving the blessings from Yitzchak, the Torah recounts:
וַיַּרְא עֵשָׂו כִּי רָעוֹת בְּנוֹת כְּנָעַן בְּעֵינֵי יִצְחָק אָבִיו . וַיֵּלֶךְ עֵשָׂו אֶל יִשְׁמָעֵאל וַיִּקַּח אֶת מָחֲלַת בַּת יִשְׁמָעֵאל... לוֹ לְאִשָּׁה.
And Esav saw that the daughters of Canaan were evil in the eyes of Yitzchak, his father. So Esav went to Yishmael and took Machlas, the daughter of Yishmael… as a wife for himself.
Another wedding! This is a very interesting way to conclude this section of the Torah. After all the events of that day, whose repercussions would echo and reverberate throughout history, the final event we are told about is Esav marrying again.
Why does Esav keep getting married?
The Shem MiShmuel explains. Yaakov receiving the blessings from Yitzchak was a bitter disappointment for Esav. In spite of his best efforts over the course of many years to win his father over, Yaakov had still outdone him. What followed was a moment of reflection for Esav. What is wrong with him that Yaakov keeps on getting the better of him? He thought and thought, and finally he found the answer: NOTHING was wrong with him! The answer, therefore, must be that he is being held back by someone else, i.e., that he is married to the wrong woman. If only he had the right wife, everything would work out for him. It is a very sad moment indeed, and one which encapsulates the path Esav had chosen for himself. Upon being presented with a rare opportunity to finally consider what was wrong with his life, he could only use it to focus instead on what was wrong with his wife.
Possibility of Partnership?
Taking this discussion one stage further, numerous commentators explain that not only did Esav have the potential to live a good and moral life, he moreover had the capacity, together with Yaakov, to be part of the legacy of Avraham and Yitzchak. What this means is that while Yaakov would devote himself to spiritual pursuits, Esav would oversee the more practical and temporal aspects of maintaining the nation.
Support for this approach would appear to be forthcoming from a comment of the Midrash Yalkut Shimoni in Sefer Yeshoshua. The Midrash states that term “גדולה – greatness” is mentioned in conjunction each of the Avos. When it comes to Yaakov, the Midrash cites the verse “וַיִּגְדְּלוּ הַנְּעָרִים – The lads grew up.” The Midrash then notes that this verse refers to both Yaakov and Esav, commenting:
ועשיו היה בכלל, אלא שקלקל במעשיו
Even Esav was [originally] included, except he corrupted his ways.
The Midrash is informing us that Esav was originally part of the greatness associated with Avraham and Yitzchak, but subsequently abdicated and forfeited this role.
In this regard, Yitzchak’s blessings were intended not only to help Esav live a meaningful life, but to allow him to fulfill his role in maintaining the material prosperity and security of the future Jewish people. The full implications of this idea is that when Rivka sees that Esav has neither interest in nor prospects for being part in that future, and therefore arranges for Yaakov to receive the blessings, Yaakov thereby assumes both roles. Indeed, from that day, he is forced to leave the spiritual environs of the study hall and travel to an alien and hostile location where he must deal with the likes of Lavan.
This will also explain an additional matter. The sages inform us that Leah was originally intended to marry Esav, except that she prayed and wept incessantly that this outcome be averted, which it ultimately was. The meaning behind this is had Esav assumed his role in the building of the Jewish people, Leah would have been his wife and partner in this venture. In the end, with Esav rejecting that path and Yaakov assuming both roles, he then came to marry Leah as well as Rachel.
Trading Roles in Exile
The full extent of the reversal that took place with Esav is brought home when contemplating a comment of the Midrash, whereby Yitzchak’s words to Esav when sending him out to hunt for food before receiving the blessings contain an allusion to the four exiles the Jewish people would endure:
“Your utensils” – this is Bavel
“You sword” – this is Persia
“And your bow” – this is Greece
“And go out to the field” – This is Edom
Why are these four exiles being alluded to at this stage? Because the blessings Yitzchak was planning on bestowing upon Esav were for purposes of assisting him in fulfilling his role within the temporal arena of the Jewish experience, including waging war against the enemies of Israel, as represented by the four exiles. And now let us consider: Esav was by this stage so estranged to such noble pursuits that not only did he not play his role in warring against the four exiles, he actually ended up spearheading the fourth and most bitter of them all – the Exile of Edom.
Although the full extent of blind anti-Semitism remains a source of heartbreaking bafflement that defies comprehension, a significant part of its core is understood as the exception those people take to the Godly message our people bears in the world. Perhaps the deepest animosity thus emerges from the corner of Esav, for whom the rejection is not only of the message itself, but also of the role which he himself could have played in promoting it. This places Esav as our final and most bitter antagonist, whose ultimate downfall will mark the final redemption itself, as we say in our prayers, citing the prophet Ovadiah:
וְעָלוּ מוֹשִׁעִים בְּהַר צִיּוֹן לִשְׁפֹּט אֶת הַר עֵשָׂו וְהָיְתָה לַה' הַמְּלוּכָה
The saviors will ascend Mount Zion to judge the Mountain of Esav, and the kingdom will be Hashem’s
May it happen speedily in our days!
 Sifrei, Beha’alosecha sec. 69, sited in Rashi to Bereishis 33:4.
 Shmuel I, 16:12.
 Bereishis 27:28.
 Ibid. verse 39.
 R’ Dovid Cohen shlit”a, Mizmor le’Dovid, Parshas Toldos.
 Bereishis 26:34.
 Ibid. 29:26.
 Ibid. 31:28.
 Ibid. 28:8–9.
 Parshas Toldos 5672, s.v. “vayar Esav.”
 See Ohr Gedalyahu, Asufos Maarachos, Sifsei Chaim and Ben Melech to our Parsha.
 Sec 23.
 Bereishis 25:27.
 Bereishis Rabbah 70:16.
 Ibid. 65:13.