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Can one shorten, in informal writing, a phrase like “Smith’s is the best among the ones I’ve seen” to “Smith’s’s best among the ones I’ve seen”, using double ’s contraction?

I myself doubt it’s possible—I’ve never seen something like this in the wild. That said, it’s non-trivial to look this up online for obvious reasons (search engines are not of much help with one-letter apostrophe combinations), so I thought I’d ask.

2

I doubt you'll be able to find some comprehensive guideline to the use of contractions in informal writing. You "can" do lots of things—for example, abbreviating please to "pls" or "plz", or your to "ur" or "yur" or "yr".

I wouldn't recommend ever using "’s’s".

In general, I don't see much value in using apostrophes to indicate reduced vowels outside of the standard use of possessive "’s" in words like "witch's". That's the only way to spell possessives like that, so fine, that's the way it is.

But in the case of "is" or "has" vs. "’s", you have a choice, and choosing to use "’s" doesn't really seem useful to me when it doesn't even indicate a reduction in the number of syllables. In a sentence like "It's the best", the apostrophe indicates the elision of a vowel sound—the sentence has a different rhythm from "It is the best," and I think it can sometimes be somewhat useful to be able to indicate that. In contrast, in a sentence like "This's the best", the apostrophe has to be read as representing unstressed [ɪ~ə], so the sentence sounds basically the same read aloud as "This is the best"—most people would automatically use a reduced vowel in "is" anyway unless you used some device like italics to mark that it is stressed.

People reduce vowels in function words all the time, and we don't usually indicate it in our writing—for example, in the previous paragraph, I didn't write "useful t' me when it doesn't even indicate ' reduction in th' number 'f syllables", even though I would pronounce reduced vowels in all of these places.

People do sometimes write and as 'n', but that reduction is a bit more salient than the reduction of [ɪ] to [ɪ~ə]. And in any case, that spelling is I think most common in short titles and so on, not in running text.

As I said, this is just my opinion—people do sometimes use apostrophes in contexts where I find them unnecessary, such as "would've" (pronounced pretty much the same in most contexts as "would have") and "I'd've" (pronounced pretty much the same in most contexts as "I'd have")—but I think most people would agree with me about the unnecessariness of "’s’s" because it just looks so strange, and typing an apostrophe instead of " i" doesn't even save much effort or space.

Somewhat similar: It seems natural to say "who'd've" in speech, but is this incorrect?

2

No, you can't. Writing is a system that is dependent on speech. In speech you can't double up the phoneme indicating the possessive case and the contracted form of "is" because they sound the same. If you try, one meaning or the other will dominate, depending on the context. Try saying to yourself (without thinking of apostrophes) "smiths best among the ones I've seen", and I think what you'll hear can be paraphrased as "the ones of Smith's that are the best among the ones I've seen" - the possessive meaning. Then try "smiths the best among the ones I've seen", and you'll hear the contracted "is".

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    In various contexts, the apostrophe is used to represent a reduced vowel rather than a strict absence of sound. For example, the word "boss’s" is not pronounced the same as "boss". I assume someone who wrote "“Smith’s’s" would be intending to represent the sound "Smiths-ihz". – sumelic Sep 17 '17 at 22:27
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    @sumelic But that rather begs the question (in the sense that logicians detest) of why you’d bother abbreviating it to begin with. As you yourself say in your answer, Smith’s is would almost certainly be pronounced the exact same way, so why opt for the fairly unsightly Smith’s’s if you’re just going to represent a pronunciation that would be implied with the normal spelling? – Janus Bahs Jacquet Sep 17 '17 at 22:34

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