In this week’s parsha, Toldot, we read of the famous story of Isaac giving blessings to his son Jacob. Everyone knows the general story: Isaac has two sons, Jacob and Esau. Esau is the bad guy and Jacob is the good guy. Esau spends his days hunting and killing, while Jacob passes the time immersed in Torah study. Jacob is going to father the Twelve Tribes, whereas Esau is, well, umm… going to try to prevent the burial of his brother Jacob in Hebron, and in general cause a bunch of trouble. 
Towards the end of his life, Isaac, having lost his vision, wants to bless Jacob. Oh, did I say Jacob? That’s who you would think he would want to bless. But in reality, we are told, Isaac wanted to bless Esau, even though he was corrupt. Through some interesting machinations, including dressing her son Jacob up in animal hides, Rebecca “tricks” Isaac into blessing Jacob in lieu of Esau.
Now although Isaac had lost his vision, he certainly had not lost his mind. Isaac was sharp as ever, and was certainly aware of the nature of his son Esau. Why did he want to bless his wicked son Esau?
In order to understand why Isaac wanted to bless Esau instead of Jacob, let us first examine the difference between two famous “bad guys,” Esau and his uncle Yishmael the son of Abraham. Although we often mention these two wicked people in the same breath, they are actually quite different.
Although he is the son of the first Jew, Yishmael is himself not a Jew (see Nachmanides’ commentary at the beginning of the parsha). Esau, on the other hand, is actually considered a Jew (albeit an apostate; Talmud Kiddushin 18a).
This becomes stranger in light of the fact that we are told (Talmud Bava Batra 16b) that Yishmael repented for his wrong-doings during the life of his father Abraham. Esau, however, never repented (and, as mentioned above, he actually tried to prevent Jacob from being buried in Hebron with the Fathers and Mothers; see Talmud Sotah 13a; Rashi on Genesis 27:45).
So what’s the deal? On the one hand, Yishmael actually repented, yet he is nevertheless not considered a child (i.e. Jew) of Abraham; Esau never repented but is considered Jewish!
This difference indicates that Yishmael, in his very essence, was not considered offspring of Abraham; he was a gentile, even though he was born from a Jew (keep in mind, that all this took place before the giving of the Torah at Mt. Sinai, when the Jewish people at large were “born”). Deep within, Esau was considered an heir of Isaac and a Jew.
This “essential Jewishness” of Esau can be explained as follows. As mentioned above, Esau tried to prevent the burial of Jacob in Hebron (Talmud Sotah 13a). At that time, Chushim (the grandson of Jacob), attacked Esau and chopped off his head. Esau’s severed head then rolled in to the Cave of the Patriarch’s and lay to rest in the grave of his father Isaac. The Code of Jewish Law (Yoreh Deah 362:5) states that it is forbidden to bury a wicked person next to a righteous person. The [partial] burial of Esau was not a problem of this sort, however, for Esau’s “head” was righteous.
This interesting story indicates that, as the great sage Rabbi Yonatan ben Uziel explains (in his translation of Genesis 53:1), that Esau was not entirely evil. In fact, his “head” – which represents his source – remains connected to, and belongs together with, the holiness of Isaac.
Despite this holiness of Esau, there was a problem. When his “head”, i.e. his supernal source, became connected to his body in this world, he became perverted and corrupt. Thus, Esau, despite his tremendously high spiritual source, never repented.
It goes one step further: Esau’s spiritual source was actually incredibly holy. In fact, his soul actually contained the source of such righteous people as Onkelos the Convert and the Talmudic sage Rabbi Meir.
Isaac’s purpose in life was to uncover the inherent holiness within the world (thus, he spent time digging wells, by which he uncovered the water hidden beneath the surface). Therefore he loved Esau and wished to bless him, for he felt that if he were to channel the power of his blessing to Esau, it would reveal the tremendous holiness inherent within him.
Isaac’s desire to bless Esau was merely a yearning to reveal the deepest nature of Esau’s holy soul. However, it was not meant to be. Rebecca knew that Esau could only reveal his inherent good when his head, i.e. spiritual source, would be detached from his body, i.e. lowly physicality. Esau was not able to reveal his “head” and thus never repented and was not able to receive Isaac’s blessings. It was only when his head was severed from his body that it ended up in the realm of holiness together with his father in the Cave of the Patriarchs.
This story and the explanation above teaches us an important lesson. Esau, who lived before the giving of the Torah, was considered a Jew, despite his wickedness, simply because he was Isaac’s son. Isaac attempted to reveal the true inner being of Esau. All the more so how we – today, thousands of years after Mt. Sinai – should not focus on where another is currently standing, but we should always focus on another’s “head.”
Not only are we all spiritually higher than Esau on a deep, profound level, but even on the surface level we are more spiritually refined than Esau! We must take this important lesson from Isaac: None of us are beyond the pale of the community. We must always reach out to those who may need our help, be it in a physical, spiritual or psychological way. Always focus on another’s “head” in our attempt to strengthen our community, the Jewish people, and the entire world.
