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There are many stories that are told over about the people who lived in Chelm. They all have the theme of: the people in Chelm were fairly unintelligent. Where did this come from? Is it true? It sounds highly unlikely that a whole city would be more unintelligent then the next city.

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And the neighboring town is Lublin, in which the yeshiva was called "Chachmei (wise men of) Lublin." Always wondered how that fit in... – Shalom Mar 16 '10 at 13:40
There may have been some rivalry or something. Perhaps people from Lublin looked down upon Chelmites? – Seth J Apr 28 '11 at 16:12

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 have been adapted into English under the title "Approaching Infinity," by M. Littman.)

So conceivably, by comparison to R' Shlomo, everyone else in Chelm seemed like a fool!

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Is it possible that it was meant as a sarcastic joke? In the way that the gemara refers to someone as "Moshe" when they said something deemed unlikely, and the way we use "Einstein" to refer to someone not so smart. Could it work the other way, that originally Chelm had a reputation for great scholars like you mentioned, so people sarcastically referred to them as being stupid? – Curiouser Aug 4 '11 at 21:17
@Curiouser: could be, I guess. In that case, it's also conceivable that chassidim had something to do with it, because this same R. Shlomo was known for his sharp opposition to the movement. – Alex Aug 5 '11 at 20:44

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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But then, why wouldn't the stereotype have focused on any of the many other towns in Eastern Europe that were the seats of various chassidic dynasties? – Alex Aug 5 '11 at 20:45

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