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Why does Hebrew use the same letter to represent two different sounds: shin and sin? As far as I know, with the exception of when using a dagesh kal, no other Hebrew letter has this property.

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There are actually arguments (a good summary of them is in the paper linked by WAF in his answer about Samech vs. Sin, mi.yodeya.com/questions/4286/…) that two other letters in Hebrew used to share this property: ח and ע. – Alex Nov 30 '10 at 5:38
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No, the other way around: that ח used to represent two different phonemes (roughly, the Ashkenazic "ches" and the Sephardic "het"); and similarly that ע used to represent two phonemes (a Sephardic "ayin" and an Arabic "ghayin"). The main evidence of this is from the Septuagint's transliterations of proper names in Tanach: compare רחל (Ραχηλ, Rakhel) vs. יצחק (Iσαακ, Isaac), and עמרם (Aμραμ, Amram) vs. עמורה (γομορρα, Gomorrah). – Alex Nov 30 '10 at 16:09
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Not an answer to the question, and unrelated to comments above, but I've seen someone who argued that in Rashi's era and place shin and sin were indeed pronounced identically. (Cf. the book of Shof'tim, 12:5–6.) One bit of evidence for this is the fact that rashi always uses shin/sin to transliterate an Old French /s/, which is odd if shin is pronounced /ʃ/ (why not just use samach, which is unambiguous?). – msh210♦ Nov 30 '10 at 16:53
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Yes, I've seen a reference to Horayas Hakorei, by R' Yekusiel of Prague (12th or 13th century), where he says that there were groups of Ashkenazic Jews in his time who merged samech and shin, and also hei and ches. The latter merger, we know from other sources, was typical of the Jews of western Germany (Rhine region) - pretty close to Rashi's area. – Alex Nov 30 '10 at 18:06
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(Citation: Radak to Shof'tim 12:6 mentions the אנשי צרפת שאינן מבינים לקרא השי״ן וקוראין אותה כמו תי״ו רפה. (Thanks to Balashon for (unwittingly) pointing me to this.)) – msh210♦ Dec 1 '10 at 7:40
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http://ancient-hebrew.org/36_creation.html , which I realize a lot of people would not consider authoritive has this idea:

The tongue closes a circle for the Samech, while air streams out from both sides of the upraised tongue for the Shin and Sin. Thus the graphic resembling two air streams split by the upraised tongue in the middle of the mouth.

So same form for the two sounds, just change the dot position to show if you should be breathing in or out for the sound.

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