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Time for some close reading. It has long been customary to use an apostrophe to indicate omission of a letter, as in “don’t” or “ma’am” A single apostrophe is sometimes used to stand for multiple omitted letters, as in ‘em for them. /1
On rare occasions, multiple apostrophes are used, as in fo'c's'le, from the nautical term forecastle and sha’n’t for shall not, common from the late 18th century to early 20th; the only current example I can think of is “rock ‘n’ roll.” /2
An affectionate or diminutive term for “little” is pronounced “lil,” but how to render it in print is problematic. A consensus seems to have emerged in the mid-20th century to write “Li’l.” /3
There’s an apostrophe standing in for the missing two missing “t”s, but not for the missing “e” at the end of the word; I speculate that’s because that letter isn’t voiced. Thus we have Li’l Abner, Li’l Peach (a convenience store chain) …/4
...Li’l Folks (Charles Schulz’s first comic strip) and Li’l Sebastian ( a horse in the sitcom Parks and Recreation). @fritinancy alerted me to the Schulz strip, as well as to a Wikipedia page listing 76 entertainers, …/5
@Fritinancy ... mostly American and mostly rappers, whose stage name starts with the diminutive for “little.” Amazingly, none spell it Li’l. /6
The spelling is roughly evenly split between Lil (Wayne) and The spelling is roughly evenly split between Lil (Wayne) and Lil’ (Romeo, Bow Wow, and Kim). The thinking behind Lil seems to be that it’s become its own word and doesn’t need an apostrophe anymore,… /7
… similar to the way the shortened form of telephone is rendered ‘phone in early 20th-century books but for a long time has simply been phone. /8
The thinking behind Lil’ seems to be, putting the apostrophe at the end of the word will signal that the original has been abbreviated, never mind specifically how. /9
That seems to be the closest model to what Trump thought he was doing in his schoolyard-bully nickname, Liddle’ Adam Schiff: misspelling the word and putting an apostrophe (which he calls a hyphen) at the end signals a ‘Lil’ pronunciation. /10
But no one in the universe would read or pronounce it that way. In his illiterate stupidity, Trump seems to have stepped out of a Ring Lardner story. But no Lardner character is that idiotic. /end
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