Horav Y. Hutner z.t.l. makes note of the fact that the expression “aluf”, chief, is used only in regard to the descendants of Eisav. The descendants of Yishmael, however, are referred to as “nasi”, prince”. He explains that this disparity in terminology had catalyzed a disparity in their relationship to Am Yisrael.
In the Talmud, Sanhedrin 99a, Chazal interpret the term, “aluf,” to be a sovereign without a crown. Eisav merited the name of monarch in a limited sense. He will survive as a nation until that day when “the saviors will ascend Har Tzion to judge Eisav’s mountain, and the kingdom will be Hashem’s.” (Ovadiah 1:21) On the other hand, Yishmael was only bestowed the title of “nasi,” which is primarily an honorary appellation with no power attributed to it.
Eisav inherited something tangible. He is identified as the beneficiary of Har Seir. Conversely, regarding Yishmael the Torah states, “Banish the maid servant (Hagar) and her son (Yishmael) for he, the son of this maid servant, will not inherit.” (Bereshis 21:10)
Horav Hutner expounded on this contrast, in light of Bnei Yishmael’s bloodthirsty desire for a share in Eretz Yisrael. He explained that Eisav, who received his own tangible inheritance, has no motivation to demand a portion in our Holy land. Yishmael, who received no share in the land, perseveres in his implacable hatred toward Bnei Yisrael, violently demanding a share in the land, from its true inheritors.