The following is a brief summary of some 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 discussing Yaakov and Esav as young men, the Torah states in Bereishis 25:27 that Esav became an "Ish Yodea Tzayid" (a man who knows trapping) and "Ish Sadeh" (a man of the field), whereas Yaakov was an Ish Tam who sat in the tents.
Rabbi Frand asked - why does the Torah's description of Esav include the use of the word "Ish" twice, while Yaakov is only called "Ish" once?
Rabbi Frand answered by quoting a sefer called Mishchas Shemen, which in turn offered the following introduction to its answer. In the early 1960's, President Kennedy talked about how they wanted to put a man on the moon. A certain person asked the Shutzer Rebbi if man will ever walk on the moon. The Rebbi answered by quoting a pasuk from Tehillim which states that the heavens are for Hashem and the earth is for man.
After the lunar landing in 1969, the person again sought an answer as to how man could walk on the moon. As the Shutzer Rebbi had passed away years earlier, the man approached the Bialer Rebbi and asked - was the Shutzer Rebbi wrong? The Bialer Rebbi said no - he was not wrong. The fact that a man can walk on the moon does not mean that the moon was a place that he could live. The astronauts who are walking on the moon need to have oxygen pumped into their pressurized suits. The astronauts cannot dwell or live on the moon without assistance, they are permanently tied to the Earth.
The Mishchas Shemen explained that Yaakov was a man of the tents. Everywhere that Yaakov went, he had a connection to his simple lifestyle from his Torah learning. It is for this reason that Yaakov was a shepherd, again a tie to a simple Torah lifestyle.
On the other hand, Esav was an Ish Yodea Tzayid - he was a man who trapped people by pretending to be something that he was not, a simple man of the field. Esav used his outer appearance to try to trick people and take advantage of them.
R' Frand next quoted a letter written by Rav Hutner to one of his talmidim. The former student had written to Rav Hutner to express his concern that the student was living a double life, since the man was in the professional world and was no longer sitting and learning full time. Rav Hutner responded, no you are not living a double life. Your secular life is being sustained and supported by the learning that you did while you were in the Beis Medrash and the learning that you find time to do now.
R' Frand closed this portion of the vort by telling a story about Dr Wallach who was previously involved with Shaarei Tzedek hospital in Jerusalem. There was a story about a man who was on a gurney, waiting to go in for surgery. The man was approached by Dr Wallach, who asked him his name so that he could daven for the man. The story was related to a gadol who said - how wonderful it is that Dr Wallach can make a kiddush Hashem by having his Torah life influence his public persona.
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