The following is a brief summary of some of thoughts said over by R' Frand on the parsha this evening. I have attempted to reproduce these vorts to the best of my ability. Any perceived inconsistency is the result of my efforts to transcribe the shiur and should not be attributed to R' Frand.
R' Frand began the vort by noting that the parsha seems to have a superfluous statement at the end of the pasuk which describes the sale of the Bechora as after recounting the transaction the Torah states וַיִּ֥בֶז עֵשָׂ֖ו אֶת־הַבְּכֹרָֽה.
R' Frand first quoted Rashi and the Sifsei Chachamim who write that the Torah wanted to underscore that Esav was Mevazeh (loosely translated as despised) the Bechora. But this still does not seem to be much more than commentary.
R' Frand then quoted R' Boruch Sorotzkin in the Sefer HaBina V'HaBeracha who states that this is an indicia of Esav's mentality. R' Frand introduced this concept by quoting R' Bukspan who had tipped him off to a Medrash HaGadol which states that after completing the transaction, Esav bragged about it to groups of people, saying - look how I ripped off Ya'akov. I got an entire meal from him in exchange for the worthless role of being the Bechor.
We know that there are times that a person will make a mistake which may be driven by desperation or even just poor planning. Afterwards the person will realize that he made mistake and could either admit that it was not a good decision ... or rationalize that it was a good result.
It was not in Esav's nature to admit to making a mistake. Instead, he strengthened his resolve by bragging to others about how he rooked Ya'akov.
R' Frand quoted the Shem MiShmuel who noted that after Yitzchak gave the blessings to Ya'akov, the Torah writes that Esav married the daughter of Yishmael. But why did this occur now and why do we even need to know that he added another wife? He answered that Esav blamed his lot on the fact that he had married a daughter of Canaan which in retrospect was not a good move since Avraham had told Eliezer that they were not appropriate for Yitzchak. He thought that maybe he had not merited the berachos because his children were the offspring of a nation which was cursed. To remedy the situation he married the daughter of his uncle.
This was yet another example of Esav blaming others for his misfortune and failing to realize that his actions were the reason for his downfall.
The Shem MiShmuel quoted his father the Avnei Nezer who cited the Ba'al HaTurim which writes that the gematria of Esav is Shalom. The Avnei Nezer explains that Esav's nature is say to - all is good, I have done nothing wrong and peace will be with me.
R' Frand closed the vort by noting that after Avraham has his name change we are no longer allowed to refer to him as "Avram" but after Ya'akov is called Yisrael we still see he is called Ya'akov at times. Why? Because as an Akov he saw himself as crooked and in need of being straightened and he lived his life striving to better himself.
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