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6

I've always speculated that it came from the fact that at one time Chelm had a very wise rabbi, named R' Shlomo (d. 1717). He is famous for his book Mirkeves Hamishneh, a commentary on the Rambam's Yad Hachazakah; appended to it is a work called Kuntreis Breichos Becheshbon, which analyzes difficult mathematical problems in the Torah. (Parts of the latter ...


4

A possible source is Proverbs (9:8) אַל תּוֹכַח לֵץ פֶּן יִשְׂנָאֶךָּ הוֹכַח לְחָכָם וְיֶאֱהָבֶךָּ "Criticize not the scoffer lest he hate you; criticize the wise and he will love you." Another close one (26:4) אַל תַּעַן כְּסִיל כְּאִוַּלְתּוֹ פֶּן תִּשְׁוֶה לּוֹ גַם אָתָּה "Answer not the fool with his foolishness lest you too resemble him."


1

I heard that the reason was because they were a Chassidic city, and in "popular culture", chassidim weren't known to be smart.



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