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.
In Bereishis 32:15, the Torah describes the gift that Ya'akov sent to Esav - עִזִּ֣ים מָאתַ֔יִם וּתְיָשִׁ֖ים עֶשְׂרִ֑ים רְחֵלִ֥ים מָאתַ֖יִם וְאֵילִ֥ים עֶשְׂרִֽים . R' Frand quoted the Ba'al HaTurim who notes that every word in the pasuk ends in a Mem. The Ba'al HaTurim explains that the reason why they were sent was because they were all blemished - Ba'alei Mumim.
But if you are trying to appease someone, why send blemished animals? The Ba'al HaTurim explains that all of the blemishes were internal.
But how did Ya'akov know that, he did not have x-rays or MRIs? R' Frand answered by quoting the Rama who cites Rabbeinu Yehuda HaChassid who states that if you put your hand on an animal, it puts its head down as its a humble creature. Those animals that did not put their heads down were sent to Esav. This can be seen from the pasuk previously - וַיִּקַּ֞ח מִן־הַבָּ֧א בְיָד֛וֹ.
R' Frand said a second vort which was based on the Ramban who explains that the parsha is a hint for the generations that the way that Ya'akov dealt with Esav should be a roadmap for Jews in the future. When Ya'akov says in 32:9 - וְהָיָ֛ה הַמַּֽחֲנֶ֥ה הַנִּשְׁאָ֖ר לִפְלֵיטָֽה the simple pshat would be to say, perhaps they will escape. But the Ramban explains that it is a promise that they will escape. The Ramban further states that in some lands a king will enact laws against us, but there will be another land for the Jews to escape to. Most recently when Hitler rose to power to Germany, there was the United States to escape to.
The Rabbeinu B'Chaye writes similarly that one should know that this is the script for us for the relationship of Ya'akov and Esav going forward.
R' Frand also quotes the Chinuch who explains that the mitzva of Gid HaNasheh is to remind us that even though Esav's angel struck and injured Ya'akov, still Ya'akov survived. Even though they may damage us, we will survive.
R' Frand also quoted a Medrash that when Ya'akov saw Esav coming from afar, Yaa'kov raised his eyes to the Heavens and davened. Ya'akov then heard in response a promise that in the z'chus of Ya'akov we will be saved.
The Kehillas Yitzchak asked - why is the answer not in your zechus as opposed to in the z'chus of Ya'akov? He answers that Ya'akov prayed - in 32:14 - הַצִּילֵ֥נִי נָ֛א מִיַּ֥ד אָחִ֖י מִיַּ֣ד עֵשָׂ֑ו - I might be saved because of my being his brother and he will have mercy on me. But what will happen in the future? To this, Ya'akov is promised that in your z'chus your descendants will be saved.
R' Frand told a story which it had been said by R' Matisyahu Solomon about his time in Gateshead. Apparently, the yeshiva was not far from the community of Wallsend. Why did it have that name? Because when Hadrian built a wall to protect England from the Romans, this was the end of the wall.
At one point, there was a journalist who went to write a story about Wallsend and the remnants of the wall - which were a pile of stone with moss growing on it. The journalist realized that he had yahrtzeit and needed to say kaddish, so he asked where the closest Jewish community was. He was told Gateshead was about ten miles away. The journalist walked in and heard the boys arguing about what R' Akiva said. He thought to himself - Hadrian built the wall to protect them and the only thing left is a pile of stones. Meanwhile, R' Akiva is still around.
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