What are the ramifications of the B?rachah, "ve'Al Charbecha Tichyeh"?
Ramban: That Eisav will vanquish other nations, and that he himself will be unconquerable. Only Yisrael will be able to stand up to him - until he will be in pain. 1
What did Yitzchak mean when he blessed Eisav, "Vehayah Kasher Tarid u'Farakta Ulon ? "?
Rashi, Targum Onkelos and Targum Yonasan: He meant that when Ya?akov fails to observe the Torah, he (Eisav) will cast off his yoke. 1
Ramban, Rashbam and Seforno: He meant thatr when Ya?akov is too harsh on Eisav, he will cast off his yoke. 2
Da'as Zekenim: He meant that when he (Eisav) will willingly serve Ya?akov, he will cast off his yoke ? so that he will be unable to subjugate him excessively.
Ohr ha'Chayim #1: All Eisav's B?rachos are for when he will serve Ya?akov, or he is subjugated under him. He will cast off his yoke, but then Beis Ya?akov will be a flame [that will consume Eisav - Ovadyah 1:18). This is why it says "Vehayah," an expression of Simchah, for then Shamayim and Aretz will rejoice.
Ohr ha'Chayim #2: He meant that when Ya?akov will rule in the world, 3 he (Eisav) will cast off his yoke, but neither of you will rule over the other.
This is similar to the prophecy during Rivkah's pregnancy, according to Targum Yonasan. Refer to 25:23:3:1.
This is a warning to Yisrael not to transgress the command in Devarim (2:5) against provoking the B?nei Eisav - which they did in the days of David ha'Melech (See Melachim I 11:16).
Ha'amek Davar: The nation called Edom will never be a mighty kingdom, just individuals from Edom will rule over nations ? such as the Caesars of Rome who came from Tz?fo ben Elifaz. TAnd it is through them that Edom will leave the yoke of Ya?akov.
QUESTIONS ON RASHI
Rashi writes: "'When you will be pained' - When Bnei Yisrael transgress the Torah...." How do we know that Esav's claim due to his pain is only valid when the Bnei Yisrael sin?
Gur Aryeh #1: A person only feels pained upon seeing someone else more successful, if he feels that that person does not deserve it, such as a Rasha. (As long as Bnei Yisrael keep the Torah, Esav must admit that they are deserving!)
Gur Aryeh #2: If Esav could remove his yoke any time he felt pained, the blessings Yaakov had received would never take effect! 1
Therefore, we must say that this caveat refers to specific circumstances only, i.e. when Bnei Yisrael do not keep the Torah.