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 Bamidbar 2:2, the Torah writes that the children of Bnei Yisrael shall encamp, each man by his banner... ("Ish Al Diglo").
Rashi explains that these marching positions based upon the flags were actually assigned by Ya'akov to his children before he died and were the same marching positions that the children traveled in when they left Egypt to bury him (quoting the Medrash Tanchuma).
Rashi makes a similar commentary in Vayechi where he writes that Ya'akov told his children how to travel and they utilized the same formation when they traveled in the desert upon leaving Egypt. Furthermore, Ya'akov instructed them that Levi should be in the middle and that it was unfitting for Yosef to travel in the formation since he was the viceroy. Instead, Ya'akov assigned positions to Efraim and Menashe, in order that there would be 3 tribes traveling on each side of the formation.
R' Frand then asked, but why was it important for the Jews to travel in formation? He answered (quoting a sefer without identifying it by name) that when Ya'akov spoke to his children at the end of his life, Ya'akov told them about their individual strengths and weakness and gave them specific tasks to perform as part of Klal Yisrael. R' Frand remarked that we learn from this how important it is that everyone understand that they have specific roles as society needs people to perform their specific tasks if it is to succeed and people are to live in peace.
R' Frand also quoted a Medrash Rabbah which stated that the giving of the flags was a show of great love by Hashem and it cited to the pasuk in Shir Hashirim where it is written that "I was brought to the house of wine, my flag upon me with love."
The Medrash then quoted R' Yissachar who explained the pasuk in Shir Hashirim as - even if a person is sitting and learning and he skips from page to page or pasuk to pasuk, his skipping is viewed with love by Hashem. R' Frand said parenthetically that a person slugging through Zevachim like Daf Yomi and skips a page because it is too dense or too hard, this is what is referred to by R' Yissachar. This person is still loved by Hashem.
The Medrash also quoted another opinion that tied the pasuk in Shir Hashirim into Kabbalas HaTorah when 220,000 angels descended with Hashem, all in formation. The Jewish people saw this and longed for their flags and formation.
R' Frand quoted the Sfas Emes who tied together these views on the pasuk in Shir Hashirim. He explained that in general a person needs to build their knowledge and skills, step by step. But sometimes a person wants to skip a step and leap forward. When Hashem sees that person who desires to grow by "leaps and bounds" (my words, not R' Frand's) Hashem says, I see that this is hard for you and that you want to skip over some of these steps, I will help you. Similarly, Hashem saw that the people longed to be like the angels, travelling in formation and He said, I will help you to travel like them as well.
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