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"law" is pronounced as /lɑ/ if you speak with the caught-cot merger, so, logic suggests "lawyer" should sound like /lɑjɚ/, as "lawyer" is basically "law" + "yer"

For me, the difference between /lɑjɚ/ and /ˈlaɪ.ɚ/ is just the backness of /ɑ/.

There are however, speakers that realize the American /ɑ/ as a central /ä/*, meaning that /lɑjɚ/ is realized as /läjɚ/ which sounds like /ˈlaɪ.ɚ/.

So, can "lawyer", for some speakers, can sound like "lier"?

(*I believe it's one of the northern cities vowel shifts?)

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    It’s probably not universal (nothing ever is), but lawyer is definitely not law + yer for me. As a word, law is /lɔː/ (with merger, /lɑː/), whereas lawyer /lɔɪ.ər/, not /lɔː.jər/ and thus not affected by the ᴄᴏᴛ–ᴄᴀᴜɢʜᴛ merger. Lawyer rhymes with coyer (i.e., first syllable rhymes with boy) and has an entirely different syllable structure from lier (or liar, which is probably the more common homophone). Commented Apr 7, 2018 at 13:59
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    @Janus: there are definitely Americans who pronounce lawyer as /lɔː.jɚ/ and not /lɔɪ.ɚ/. The question is whether any of these Americans have a COT-CAUGHT merger where /ɔ/ is realized as [ä], so their pronunciation is [läː.jər], which sounds a lot like /ˈlaɪ.ɚ/ Commented Apr 7, 2018 at 14:11
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    It probably won't happen in the Northern Cities vowel shift. That doesn't have the COT-CAUGHT merger, so law is pronounced [lɒ] and not [lä] (which would be the first part of lot). Commented Apr 7, 2018 at 14:19
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    @JanusBahsJacquet For folks who pronounce boy with a more closed /boɪ/ not /bɔɪ/, lawyer becomes /loɪər/ or /lojər/. By losing the connection with law /lɔː/ we think of a lawyer as someone who does something or other with “loys”, whatever those are. :) See also Tom Sawyer, where nobody now knows there were ever once any saws /sɔːz/ involved in that profession because of how the more open /ɔ/ has become a more closed /o/ in Tom’s surname.
    – tchrist
    Commented Apr 7, 2018 at 15:09
  • @tchrist Even for those of us who don’t have a closer /o/ vowel there, the disconnect is real—I didn’t connect lawyer with law until… well, until some age that I’m old enough to remember. I remember the ‘aha’ moment, so I almost certainly grasped the connection through spelling, not pronunciation. Commented Apr 7, 2018 at 15:12

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logic suggests "lawyer" should sound like /lɑjɚ/, as "lawyer" is basically "law" + "yer"

Since when is English pronunciation logical? As Wiktionary notes, outside of the South lawyer is pronounced in American English as /ˈlɔɪ.ɚ/ (phonemically). Liar, meanwhile, is transcribed by Wiktionary as /ˈlaɪ.ɚ/; some dictionaries don't list lier, but Wiktionary transcribes it as a homophone of liar. The diphthongs /ɔɪ/ and /aɪ/ are not affected by the cot-caught merger. Wiki doesn't list, and I'm not aware, of any American accents that merge /ɔɪ/ and /aɪ/, so outside of the South these two are certainly not homophones.

In the Southern US, per Wiktionary, lawyer can be pronounced /ˈlɔ.jɚ/. Such accents generally lack the cot-caught merger, though they may have the rod-ride merger (see Wikipedia), which would merge /ɑ/ and /aɪ/. Hypothetically, if a speaker did have both the rod-ride merger and the cot-caught merger, then lawyer (/ˈlɔ.jɚ/) would indeed be a homophone of lier/liar (/ˈlaɪ.ɚ/); the presence of the /j/ isn't particularly relevant, since the diphthong /aɪ/ would end in a glide anyway. But I suspect that such speakers are fairly rare, since accents with one merger generally lack the other.

There is also a merger between /aɪər/–/ɑr/ in some Southern AmE dialects; this can merge tire and tar, but not lier/liar and lawyer, since the latter has two syllables.

(As a general reminder: even in speakers that, as you say, realize the American /ɑ/ as a central [ä], we would still transcribe that phoneme as /ɑ/; slashes are for phonemes and square brackets are for phones. I think your question may have gotten this distinction confused.)

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