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Parshat Vayshlach – Wrestling Until Dawn

בס”ד

Genesis 32:4-36:43

This Torah portion is both a continuation of the narrative concerning Jacob, the matriarchs and their children, as well as a series of prophecies and mystical secrets hidden within that narrative. Jacob, while moving his family back to the land of Canaan, and on the path to encounter his brother Esau, has a supernatural encounter.

The verse states, “and Jacob was left alone, and a man wrestled with him until dawn” (Genesis 32:25). Yet this “man” was not a man at all; it was an angel. And it was not just any ordinary angel. In the Midrash, we discover that it was the angel specifically designated over Esau—the שרו של עשו, saro shel Esav. We know this because when Jacob finally meets Esau, he makes a somewhat odd statement, “for truly, I have seen your face, and it is as though I have seen the face of an angel, and you are pleased with me” (Bereshit Rabba 77:1; Genesis 33:10). Looking at Esau, it was as if Jacob had seen the face of angel—because the angel did resemble Esau.

The significance of Jacob’s momentary struggle with the saro shel Esav has to be understood according to its two component parts, the first being the struggle itself, and the second being the fact that it ended at dawn. When the angel discovers that he cannot overcome Jacob, he gives Jacob a prophecy that his name would eventually be changed to Israel, meaning, “one who wrestles with angels”. This was not only a match between Jacob and an angel, but the spiritual forces of Esav and Yisrael. It was a microcosmic representation of the struggle of Israel with the nations of the world throughout history.

This pattern of the exile and redemption of Israel appears to be cyclical, but it is limited to four instances: Egypt, Babylonia, the Greek Empire and the Roman Empire. And history is linear and finite. “Dawn”, in the narrative, refers to the period leading up to sunrise. But it also hints at a time in the future when salvation will “dawn” for Israel.

There is a verse in Psalms, which reads, “[it is good] to speak of Your kindness in the morning, and Your faith at night” (Psalms 92:3). “Morning” represents a time of clarity, when G-d’s Kindness is apparent. Therefore, we can speak of it, we can point clearly to it. On the other hand, “night” represents times of darkness, when G-d’s Kindness is hidden from view. During those times, we have to rely on faith to help us through. For Israel, “night” represents exile, while “morning” represents redemption. Thus, the “dawn” mentioned in our verse represents the bright future that lays ahead for Israel, and by extension, the rest of humanity.

When Rebecca was pregnant with her twins, she was told, as a prophecy, “one nation shall be stronger than the other nation.” (Genesis 25:23). What this means is that the forces of Esau and Jacob never rule concurrently. One is always stronger than the other, as Rashi comments, “they are never equal in greatness. When one rises, the other falls” (ibid.).

Fortunately, we are also given the key to understanding what influences this balance of power. When Isaac blesses Esau, he tells him, “You shall serve your brother, but when you have dominion, you will break his yoke from your neck” (ibid., 27:40). Rashi quotes the Midrash, and explains that, if and when the Children of Israel fail to uphold the Torah, the spiritual descendants of Esau can justifiably claim that their ancestor Jacob has been given the birthright unfairly. (Rashi, ibid., Bereshit Rabba 63:7). If Israel “rises”, meaning, attains leadership in the world, it is only for the purpose of increasing the awareness of G-d amongst humanity. Therefore, if the Children of Israel fail to fulfill this mission, they do not deserve the upper hand. But if they do fulfill the Will of G-d, it is fitting that they have it, since it is for the benefit of all mankind.

On a deeper and more personal level, “Israel” and “Esau” represent two forces at work in the lives of all human beings, otherwise known as the yetzer tov, the “good inclination” and the yetzer hara, the “evil inclination”. It is the job of every human being to empower his or her good inclination, and to subjugate the evil inclination, harnessing its power to serve G-d. Only then can these two forces co-exist in harmony.

“And these are the generations of Esau; Esau is Edom” (Genesis 36:1). The nation that descended from Esau was Edom. But, like Amalek, who also makes his debut in this Torah portion, Edom represents a spiritual entity, whose mission and outlook have been taken up by many nations and cultures throughout history. Of the tribal chieftains of Edom is Magdiel, which is identified as Rome (Rashi, ibid.). The Roman Empire, a mortal enemy of Ancient Israel, and the subsequent Western civilization that arose from it, personifies Edom, or Esau, in the world.

The fourth and final exile of the Jewish people is referred to as galut Edom, the exile [imposed by] Edom. It began with the destruction of the Second Temple by the Roman imperial forces in 70 CE and continues to this day. A retrospective view of history to the present reveals that the West has truly been in ascendancy, from its Greco-Roman origins to the infusion of its ideas into the collective subconscious of humanity. And the heritage of the West has indeed brought much good to the world: democracy, government, law, science, education, medicine, art, music and humanism. It would be overly simplistic to view history as a spectator sport, and the struggle between Edom and Israel as a standoff between opposing teams.

This is because the moral foundation of the West, its spiritual heritage, is to be found in the Torah itself, in its Judaic origins. When prominent cultures lose their moral bearings, when they cease being accountable to the values that justify their existence, they are endangered; history is moving in the direction of the ultimate redemption. For this reason, it also does not matter if you are Jewish or Gentile. Whether or not you will rejoice when that day comes is not a matter of genetics or ethnicity, nor a factor of your political affiliation. Iit depends only on whether you have made Torah your beacon in life and have placed G-d at the center. The ultimate leadership must belong to G-d Himself.

The haftara for this week is the Book of Obadiah, which is one chapter long, and deals only with the downfall of Esau and Edom. It is a prophecy given to Obadiah because he himself was an Edomite convert, and therefore was fitting to prophesy about them. Our Sages tell us, “Obadiah dwelled amongst two evildoers, Ahab and Jezebel, and did not emulate them. This incriminates Esau, who dwelled amongst two tzaddikim, Isaac and Rebecca, and did not emulate their ways” (Sanhedrin 39b).

Jacob said to Esau, “may my lord go before me…until I come to my lord at Mount Se’ir” (Genesis 33:14), yet we never see this happen. Rashi asks, “when will Jacob meet Esau? When the messiah comes, as the verse states (Obadiah 1:21), “and saviors shall ascend Mount Zion to judge Mount Se’ir”, at which point, “and the kingship will be G-d’s”. May we all be blessed to hold fast to the Torah and to partake of the joy of redemption.


By Rabbi Tani Burton


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