From Dick Margulis:
The first editor of the Encyclopædia Britannica, a Scot named William Smellie, was a distant relative to my wife, whose surname is Smillie, pronounced smiley (the spelling was changed at some point to avoid bad jokes, apparently). I believe William pronounced it smiley as well. John W. Willey (pronounced wily) was the first mayor of Cleveland (the brand new restaurant where my son is a sous chef is named The Willeyville because Willey bought a tract of land on the city's west side and named it that), and there are some towns in England named Willey, although I don't know that they share the same pronunciation. And a shibboleth here in New Haven is the pronunciation of Whalley Avenue, named for the English regicide Edward Whalley and pronounced whale-y, although Our Lady of the Google Navigator, who is Not From Around Here, rhymes it with alley.
I can't blame people who think my wife's name rhymes with Millie or the restaurant is the willie-ville, nor those who have trouble with Whalley, because the way we were all taught to decode a double-ell is that it makes the preceding vowel what we non-linguists call short. But as I find myself at the confluence of these three examples of this unusual (I think) orthographical feature, I'm just curious what the history of it is, if anyone at Language Log Plaza happens to know.
I'll throw this one directly to our readers, before I embarrass myself by speculating that contrastive consonant length might have survived in some dialects through the time of the Great Vowel Shift. The safe and obvious answer is that the use of doubled consonants to signal short vowels remained erratic well into the 18th century, and some proper names were frozen in spelling before English spelling was otherwise regularized. But is it a coincidence that these three example all involve 'll'?
I'll just note that the OED's list of variants for ale includes alle, aill, aeill, aell, aiell, aill, all, alle, ayill, ayll, aylle:
1535 W. Stewart tr. H. Boethius Bk. Cron. Scotl. II. 660 Of wyne and aill takand thame sic ane fill.
And I'll also note this citation from the OED's entry for wily:
1639 J. Clarke Parœmiologia 285 As willy as a foxe.