The birth and development of Yaakov and Eisav led to a historical, difficult relationship, which more often than not, had Eisav’s offspring trying to bring harm upon Yaakov’s offspring. While some enmity stemmed from the struggle over the blessings, most of the tension arose from the fact that the two were born as very different people leading to very different nations, as was prophesied from the time of pregnancy (see Bereishit 25:23).
This background leads to a very difficult question. If a special miracle was needed to allow Rivka to conceive, why did the miracle have to result in the birth of twin boys, considering it was already prophesied that the chosen nation would come from only one of the sons? Let us present one of the possible approaches that stem from the words of Chazal.
Shir Hashirim Zuta (1:15) indicates that Eisav was slated for greatness had he not deteriorated. The Midrash Tanchuma (Shemot 1) blames mistakes in Yitzchak’s parenting for the failure. Yitzchak was concerned that if he would be too strict with Eisav, Eisav would rebel from his father’s path. His approach did not help. Chazal teach us that rebuke can be very effective if one does it in the right way (see Berachot 7a). Perhaps the most poignant advice for dealing with those who have begun to stray is, "One should always have the left hand push away and the right draw closer" (Sota 47a). Had Yitzchak succeeded, there could have been two tribes, albeit not perfectly unified, but creating a situation of healthy rivalry where each one pushes the other to greater heights. Instead, Eisav emerged as he did, leading, two generations later, to Amalek. The rivalry is not healthy, and it will continue until the coming of Mashiach (see Ovadia 1:21).
Taking a look at Eisav, we see that he contained points of fine behavior, even a certain degree of gentleness. His respect for his father was extreme and sincere (see Bereishit Rabba 65:16), and even his hypocritical behavior before Yitzchak stemmed from a good place. It is hard to picture how his coarse behavior in speaking before Yaakov and the major sins he committed (see Bava Batra 16b) fit in.
The solution is that one has a "first-stage nature," which requires educational work to take advantage of – to keep the problematic part in check and to channel the nature in the right direction. Eisav certainly was the son of Yitzchak and the grandson of Avraham, and he inherited many of their fine qualities. Yet, when he did not used his qualities properly, he turned into a "wild donkey" (see Iyov 11:12). The gemara says: "I created an evil inclination, and I created the Torah as a remedy" (Kiddushin 30b). Without Torah, it is not possible to develop properly.
There are groups who speak these days about Jewish awareness. They feel pressure from their lack of satisfaction with their movements’ direction. However, awareness, knowing how their father and their grandfather prayed, is not enough to give significant results. Maybe it will bring them a little respect for their fathers (as Eisav had). But this will not stop them from tricking their fathers to quiet their consciences and continuing to sin horribly. What they need is to actually sit in the tents of Torah, as Yaakov did, and use authentic Torah as a remedy. Education cannot be limited to strokes of the face; there need to be a left hand pushing away and a right hand drawing close. The use of the left is as important as that of the right.
Let us learn from our forefather’s mistake and fix that which is awry now and in the future.