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Beit Midrash
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But the Hebrew of the phrase, "Lama zeh tish’al lishmi," is quite unusual. The word "zeh-this" seems superfluous here; the sentence would make much better sense without it if it simply said: "Lama tish’al lishmi?"
Now, we know that there are no punctuation marks in the Torah; in fact even the separation between words is subject to interpretation. So, if you read the last word ("lishmi") as two words instead of just one, you get the phrase, "lama zeh tish’al li: sh’mi," meaning, "‘Why Do You Ask Me This?" is, in fact, my actual name!"
To explain: Rashi identifies Yakov’s adversary as Esav’s guardian angel, a malevolent figure who means to do harm to Yakov & his (Torah) way of life. And so, his self-declared name, & essence, make a lot of sense. For the philosophy of, "Don’t ask me any questions!" is indeed a serious threat to Torah learning & the acquisition of spiritual knowledge. It is davka via the asking of probing & penetrating questions that we confront & challenge the subject at hand, & ultimately arrive at the truth.
Every Yeshiva student who has ever learned Gemara knows that the Rebbe gives you one point for a great answer, but two points for a great question!
Too often, students are told, "Why do you ask me this? Don’t ask me any questions! Accept whatever you are told, without any doubt or delay!" To question authority is deemed heresy, blasphemy, apikorsis! But that is a very wrong & dangerous attitude; the entire Talmud, in fact, is one long series of questions - & the search for answers.
After the Exodus from Egypt, Moshe tells Bnei Yisrael (Ex. 13:14): "V’haya ki yish’alcha bin’cha machar laymor: Mah Zot?" And it shall be, when your child asks you tomorrow what is this (the Pesach ritual), you shall tell him….etc." With a touch of Rabbinic license, we can read the phrase a bit creatively: "When your child asks you a question, then you know there will certainly be a tomorrow," a bright future for the Jewish People.
The mark of a Jew, no question, is the Question Mark.
Rabbi Stewart Weiss
Was ordained at the Hebrew Theological College in Skokie, Illinois, and led congregations in Chicago and Dallas prior to making Aliyah in 1992. He directs the Jewish Outreach Center in Ra'anana, helping to facilitate the spiritual absorption of new olim.

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