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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 ...


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."


According to my Lithuanian grandparents, Chelm was a joke name used to make fun of Kelm. The city of Chelm is located in Poland, while the city of Kelm (Kelmé) is located in Lithuania. I don't recall if a reason was given for the switching of names, whether it has to do with mocking Polish in general or whether it was simply a matter of mispronouncing the ...


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


A possible source of this saying is, perhaps, by establishing a connection between two quotes: "A fool is not aware of his folly" (Gemara in Shabbos 13b), therefore if you tell him he is fool, he will be angry, because "Anger rests in the heart of fools" (koheles 7:9)

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