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's first vort focused on the question - why do we call Esav "Edom" and his descendants by the same term, simply because he asked for soup which he called "Edom." If Ya'akov had been making pizza and Esav had asked for pizza, would he and his descendants have been called pizza?
R' Frand answered by quoting R' Hutner who explained the difference between Jews and Akum. A Jew will focus on self improvement and understand the totality of the circumstances. But Esav, although aware of the fact that Ya'akov was making this food because their father Yitzchak was in mourning for their grandfather Avraham, was solely thinking about his stomach. He did not care that his father was mourning or that his grandfather died, he just wanted the red stew. And so he became known as Edom.
The second vort related to a Medrash HaGadol which added a post script to the story. The Medrash relates that after Ya'akov traded the Bechorah for the soup, Esav called a town meeting and invited everyone to hear about the trade. He loudly proclaimed that he had obtained Ya'akov's food and drank his wine, in exchange for the Bechorah. He proceeded to laud the transaction and how he had hoodwinked Ya'akov in the deal. In so doing he cemented his rationalization that he had done the right thing.
R' Frand said that this was emblematic of Esav's view of himself as infallible and without fault. He quoted the Ba'al HaTurim who notes that the Gematria of Esav is Shalom - showing that he was always at peace with this actions. Meanwhile, Ya'akov is similar to Akuv (meaning bent or crooked) because he was constantly bent over and examining whether he had done the right thing.
R' Frand's third vort related to the pasuk in Bereishis 27:33 - וַיֶּֽחֱרַ֨ד יִצְחָ֣ק חֲרָדָה֘ גְּדֹלָ֣ה עַד־מְאֹד֒. He quoted the Medrash Tanchuma, which observes that a person does not have חֲרָדָה֘ גְּדֹלָ֣ה unless he had previously had a lower level of fear. The Medrash explains that Yitzchak had a previous fright at the Akeidah when the heavens opened up as his father was about to sacrifice him and he saw the Merkavah.
But why would the realization in this week's parsha cause greater fear?
R' Frand first quoted R' Ya'akov Breish (sp?) who was the Chief Rabbi of Switzerland during and after World War II. When he spoke on Yom Kippur after the war ended, he explained that the two fears are emblematic of two ways that Jews have died off over history. There were Jews who died on the Mizbeach when they gave up their lives Al Kiddush Hashem. But there are also Jews who died because they ate, drank and intermarried with non-Jews. This was the second fear of Yitzchak.
R' Frand gave another explanation, which was his own thought. He said that perhaps Yitzchak was afraid because he suddenly realized that his entire view of Esav was wrong. To this point he had not seen Esav for who he really was, but upon hearing Esav's reaction to the giving of the Berachos to Ya'akov, he saw Esav as the Rasha that he was.
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