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I was under the impression that any object, compound or not, following a preposition such as "to" must take the objective case; therefore, "Give this work to whomever looks idle."

However, in the classic book, The Elements of Style, the following passages states otherwise:

Give this work to whoever looks idle.
In the last example, whoever is the subject of looks idle; the object of the preposition to is the entire clause whoever looks idle.

What am I missing here? Wouldn't the fact that the clause is the object to the preposition "to" make whomever the right choice?

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    The rule I learned many years ago was that the case demanded by the prepositional complement trumps other claims. So 'He looks idle' → 'Give this work to whoever looks idle.' BUT 'The Elbonians abused some of them' → 'Give most aid to whomever the Elbonians abused'. // My advice would be to avoid the awkward-/dodgy-sounding (Orwell advises that this is even more important than maintaining grammaticality) and rephrase. Here, 'Give this work to anyone who looks idle /all those who look idle / all those who seem to have too little to do.' Nov 25 at 12:39
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    Does this answer your question? When whoever vs. whomever fails the he/him test << 'He'll give the key to whoever needs to open that cabinet' is indeed correct. Whomever would be ungrammatical. That follows the actual rule. >> [J Lawler] Nov 25 at 12:43
  • No, it wouldn't. There is no 'rule'. "Whoever" may be preferred, but "He'll give the key to whomever needs to open that cabinet" is grammatical. Indeed it is the preferred alternant in formal style.
    – BillJ
    Nov 25 at 13:13
  • I may add that I found great insight in this link web.ku.edu/~edit/whom.html after posting the question. The 2 rules he provides should, in most cases, solve the problem. Nov 25 at 13:19
  • The expression "who(m)ever looks idle" is a fused relative construction. It's a noun phrase, not a clause, where fused "whomever" is simultaneously head of the NP and subject of the relative clause.
    – BillJ
    Nov 25 at 14:24
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Give this work to who(m)ever looks idle.

Both forms sound a little weird because the construction imposes competing but unsatisfiable requirements: "who(m)ever" must be nominative because it's the subject of "looks", but it must be accusative because it's the head of "who(m)ever looks idle", which is object of the preposition "to" and it can't be both, so you have a quandary.

There's no way to get out of the quandary: you have to infringe one condition or the other. English is not well designed in this respect!

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