Malevitz has asked a good question. The different pronunciation of words like flaysh/fleysh or khayn/kheyn is one of the main features defining the border between what is known as “Central Yiddish,” i.e., the Yiddish that was spoken in most of Poland and southward into Transylvania, and the “Eastern Yiddish” (subdivided into “Northeastern” and “Southeastern”) spoken in Lithuania, Latvia, eastern Poland, Belarus, Ukraine and Rumania. According to all the rules, the Hebrew word she’eylah, pronounced shayle to the west of this border, should be sheyle to the east of it. Why isn’t it?
Frankly, I don’t know. We indeed seem to be dealing with a curious anomaly. If one takes similarly vocalized Hebrew words in Yiddish, such as beheymah, “cow,” or geneyvah, “robbery,” they are indeed pronounced behayme and gnayve in Central Yiddish and beheyme and gneyve in Eastern Yiddish. This should have happened with she’eylah and didn’t.
At the same time, one needs to keep in mind that Eastern Yiddish does have an “ay” vowel and that its speakers are routinely used to this sound; they just articulate it in words where Central Yiddish speakers don’t. Thus, for instance, the word for “white,” pronounced vaas in Central Yiddish, with a long “a” vowel like that of “father,” is vays in Eastern Yiddish, and maan, “mine,” in Central Yiddish is mayn in Eastern Yiddish. This distinction, too, forms part of the border between the two dialects.
Moreover, there are even some unusual cases in which, as in shayle, the “ay” of Central Yiddish remains “ay” in areas of Eastern Yiddish, too. In his “Geshikhte fun der Yiddisher Shprakh,” the Yiddish linguist Max Weinreich remarks on the odd fact that the Central Yiddish suffix -hayt, a cognate of the English -hood that roughly corresponds to it, (e.g., kindhayt, “childhood,” frayhayt, “freedom”), remains -hayt in Northeast Yiddish and does not change to -heyt as might be expected, even though this does happen in Southeast Yiddish. And Weinreich comments, “Although this articulation [in Northeast Yiddish] certainly seems to be taken from Central Yiddish, I cannot think of any explanation for it.”
If a great linguist like Weinreich could not explain why the Central Yiddish -hayt failed to become the Northeast Yiddish -heyt, an amateur like myself can be excused for being stumped by the question of shayle. The only possible solution I can think of is one based on the analogy of written forms. If we look at the spelling of the Hebrew word she’eylah, dl`y, we see that, although there are no other similarly vocalized Hebrew words in Yiddish having the pattern of consonant-alef-consonant-heh, there are slightly differently vocalized words that do have this pattern, such as ga’avah, de`b, meaning “pride”; ta’avah, de`z, meaning “lust,” and de’agah, db`c, meaning “worry.” In their pronunciation, moreover, all of these words fit the rules for the Central Yiddish/Eastern Yiddish border — that is, in Central Yiddish they are pronounced gaave, taave and daage; in Eastern Yiddish, gayve, tayve and dayge.
My suggestion with regard to the word shayle, therefore, is that, since Hebrew words in Yiddish are printed (as they generally are in Hebrew) without their accompanying vowel signs, Eastern Yiddish speakers, seeing that the words for “pride,” “lust,” “worry” and “question” all had the same pattern of spelling, may have brought their pronunciation of the last of these into line with the others. That is, since they said gayve, tayve and dayge, and not geyve, teyve and deyge, it may have seemed natural to them to say shayle and not sheyle as well.
Regularizations of pronunciation based on analogies of spelling do sometimes take place in literate cultures. The tendency of some Americans to pronounce the first syllable of “almond” as “ah,” for example, though it strikes many people as affected, comes from the written analogy with words like “calm,” “palm” and “balm.” Perhaps something similar happened with shayle in Eastern Yiddish.