This week's parsha concludes with the death of Yishmael. Referring to Yishmael, the last verse states "al pnei chol echav nafal," literally translated as "over all his brothers he dwelt." Rashi picks up on the peculiar terminology used ("nafal" usually means falling or dying), and contrasts it with "yishkon" (literally to dwell) used in the angel's prediction to Hagar concerning the birth of Yishmael. To explain, Rashi cites a medrash that says that until Avraham died, Yishmael's dwelling is referred to as as "shachen," after Avraham's death, Yishmael's dwelling isconveyed as "nafal." The Kli Yakar questions whether the two expressions should be in reverse? It wasn't until Avraham's death that Yishmael repented. Would it not be proper for the period of life that Yishmael sinned to be articulated as "nafal"? The Kli Yakar proposes that these words may actually have the opposite connotations. "Yishkon" could mean to dwell with self-confidence, sure of oneself and not recognizing error. This was the case until Yishmael repented and then he was "nafal," subdued - he now recognized his faults. However, the Kli Yakar's explanation might hint to something much deeper.
Rabbi Yitzchak Hutner in Ma'amarei Pachad Yitzchak on Succos, quotes a Ba'al Haturim on the above verse: "The reason for the juxtaposition of "al pnei chol echav nafal," to "v'eileh toldos Yitzchak (and these are the offspring of Yitzchak)," is to tell you that only when Yishmael falls, then will ben Dovid (moshiach) arise - who is from the offspring of Yitzchak." Rabbi Hutner says that from the words of the Ba'al Haturim arises a very interesting question. We are well aware of the special dynamics of the relationship between Ya'akov and Eisav. It is understood clearly from Shem's prophecy in next week's parsha, "ul'om mil'om ye'ematz," that when one falls the other will rise. If such a dynamic exists between Yishmael and Yitzchak as well, why is it not stated clearly in the Torah?
Rabbi Yitzchak Hutner answers that Eisav and Yishmael are positioned very differently from each other. Yishmael's children are "nesi'em,"chieftains for their nations. Eisav's children, on the other hand, are "alufim," which the Talmud in tractate Sanhedrin explains to mean as "kings without a crown." Although his descendants did not deserve to serve as kings, they were royalty nonetheless - by virtue of their dictatorship. By contrast, Yishmael's offspring may have been in lofty positions, but they never became kings. This difference is because only Eisav became an inheritor, while Yishmael was sent away from the house of Avraham. That is why concerning Eisav's offspring the verse says "These are the chiefs of Edom... in the land of their possession." Whereas by Yishmael the verse merely says "These are their names by their open cities and their strongholds." There is nothing signifying possession/inheritance of land for Yishmael.
This has multiple ramifications. The Rambam points out that it is only the Christians (descendants of Eisav) that contest ownership of the Written Torah, claiming that they are the true keepers of the "bible." They dispute the Oral Torah that explains "b'Yitzchak v'lo kol Yitzchak," "in Yitzchak -but not all of Yitzchak," to the exclusion of Eisav. Yishmael is not involved. The Torah is clear that he will not inherit. On the other hand, being that the progenies of Eisav inherited land, they will not fight for ownership of Eretz Yisrael. The offspring of Yishmael are therefore eternally jealous of their lack of inheritance and will contest every bit of land owned by the Jewish People.
Rabbi Hutner goes on to say that because Yaakov and Eisav contest ownership of the Written Torah, it makes perfect sense that their struggle is stated explicitly in the Torah. Whereas Yishmael cannot lay claim to the written Torah, therefore his fight is only hinted to in the Written Torah.
Rabbi Yitzchak Hutner concludes, that now we can understand the medrash quoted by Rashi, as mentioned earlier. The reason why the Torah uses the word "nafal" after the death of Avraham is because it is after death that the inheritors become clear. It was now obvious that Yishmael will not inherit.