It is well known among those who closely observe the writing style of newspapers that the New York Times uses an apostrophe in acronyms and initialisms that are plural, such as CD’s or DVD’s.
Less well known is that the paper also uses them when writing out plural letters of the alphabet, which leads to this ridiculousness:
In kindergarten in Jersey City, he was scolded for his stubborn insistence on drawing two-tiered lowercase “a” ’s.
That’s a plural “a” in two-tiered lowercase “a” ’s.
It is a slight irony, as it appears in an article about changing the typeface of road signs to improve their readability, The Road to Clarity.
The first problem is putting the apostrophe and the “s” outside the quote marks: two-tiered lowercase “a’s.” would be slightly more readable. It would allow the space to be removed before the apostrophe, which in any case isn’t really doing a very good job at keeping the double closing quote marks and the apostrophe apart.
Having the quote marks at all reduces readability further: two-tiered lowercase a’s. would be still better.
Of course, using a capital “A” would be still more readable, but it’s the lowercase letter “a” that’s being written about.
You can spell out “H” as “aitch” or “haitch” (depending upon your dialect) and you can spell out “M” and “N,” as in “em-dash” and “en-dash,” but unfortunately, the letter “A” isn’t usually spelled out in English, or else there’d be an even better solution, something like two-tiered lowercase ays. You can’t do that, though, because “ay” is a synonym for “aye” (as in, “Aye, aye skipper!”) and is pronounced the same way, just as it is in “¡Ay caramba!”
UPDATE: Of course, as “bon bon” at the Buffistas.org discussion board has pointed out, the best way to solve this problem is to take away the plural: He was scolded for his stubborn insistence on drawing a two-tiered lowercase “a.”