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When I take the word 'extraordinary', 'exceptional' and 'outstanding' literally, it simply means something 'out of the ordinary', 'rare and/or unusual', or something which 'stands out from the rest', but not necessarily conferring any positive connotations. And indeed this is reflected in the dictionary.

Extraordinary

  1. beyond what is usual, ordinary, regular, or established
  2. exceptional in character, amount, extent, degree, etc.; noteworthy; remarkable

Exceptional

  1. forming an exception or rare instance; unusual; extraordinary
  2. unusually excellent; superior

Outstanding

  1. prominent; conspicuous; striking
  2. marked by superiority or distinction; excellent; distinguished

However, very rarely do I see text use these three words, by themselves, without conferring a positive connotation (see the second definitions). If they choose to convey something as out of the ordinary without carrying a positive connotation, they'd use words such as 'striking', 'unusual', 'uncommon' or 'strange'.

You can of course attach negative connotations using, for example, 'exceptionally bad' to attach 'exceptionally' to the first definition. But if I say, this taste is 'extraordinary', you'd immediately associate it with being positive, while it might just be plain weird.

So are the 'literal' definitions of these words, in and of itself, now obsolete?

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    How extraordinary that you think so. I personally find nothing exceptional about using the more literal senses of at least the first two. Outstanding payments aside, however, I’d agree that the literal meaning of outstanding is at least archaic. – Janus Bahs Jacquet Mar 7 '15 at 14:59
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    I think this is Off Topic (Primarily Opinion-based). Or a peeve, given thousands of written instances of an outstanding failure – FumbleFingers Mar 7 '15 at 15:09
  • @FumbleFingers I have never read such a phrase use in normal usage, LSNED. If you go on the web search, most of the results are from books, and not very common books I may add. – dayuloli Mar 7 '15 at 15:12
  • @dayuloli: Obviously an outstanding success is far more common - so much so that dictionaries would invariably specifically refer to the "positive associations" usage. But the answer to your actual question can only be "Not always", and everything else is just opinions. – FumbleFingers Mar 7 '15 at 15:44
  • ...and you don't really need exceptional circumstances to find examples of your other words being used in neutral/negative contexts. – FumbleFingers Mar 7 '15 at 15:49
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Mostly, but not necessarily. Here are some examples where they have negative connotations:

A new, extraordinary tax was imposed by the government.

Theirs was an exceptionally stupid idea.

You have outstanding debts.

Granted, the last one is cheating since this is a different meaning of outstanding, but it is certainly not a good connotation.

As a general rule, those words carry good connotations because very often being different from the norm is considered as better than the norm. However, as usual, context is everything:

He is an extraordinarily bad father.

She is an exceptionally bad mother.

They are outstandingly bad parents.

In other words, while these terms do indeed most often carry a good connotation, they can and will be understood to carry a bad one in the right context.

My gut feeling is that of the three, outstanding is the one least likely to be associated with a negative connotation (though it will be understood if used in such a context), while both exceptional and, even more so, extraordinary can more often be used in such a way.

Finally, some real world examples:

  • From the Free Dictionary's definition of egregious:

    1. outstandingly bad; flagrant: an egregious lie.
  • From an article in Forbes magazine:

    The OECD's Extraordinarily Bad Report On Inequality And GDP Growth

  • From the Free Dictionary's definition of atrocious:

    1. Exceptionally bad; abominable: atrocious decor; atrocious behavior.

As pointed out by @JanusBahsJacquet below, my examples above are all about the adverb and not the adjective. True, that is cheating. Of the adjectives, extraordinary is the one most often used for neutral or bad connotations while outstanding (in the sense mentioned in the OP) and exceptional are indeed almost always positive in the absence of qualifiers.

Extraordinary on the other hand, is really quite often used negatively. In addition to extraordinary tax, you also have extraordinary circumstances, extraordinary request, extraordinary needs, none of which imply anything good.

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    Most of your examples are kind of cheating: just because the literal meaning of the adjective starts to be eclipsed by the derived sense, it doesn’t necessarily follow that the corresponding adverb has to follow suit. All these three adverbs are just emphasisers, really, and thus more or less impervious to positive/negative slanting—the adjective they modify handle that. As adjectives, though, they have to have a positive/negative slant. – Janus Bahs Jacquet Mar 7 '15 at 15:34
  • I totally agree with everything you said here. Context is everything as always. I think what I really meant to ask is if those words are used by themselves, are they always positive. In your examples, you used 'exceptionally stupid', 'extraordinary tax' etc. The 'stupid' and 'tax' themselves carry negative connotation, which sways the meaning of the preceding words. – dayuloli Mar 7 '15 at 15:35
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    @dayuloli well, extraordinary is the most neutral of the three. It is often used to describe bad things. Extraordinary circumstances for example, is more often bad than good. – terdon Mar 7 '15 at 15:37
  • @JanusBahsJacquet fair enough. I admit that outstanding and exceptional are almost always good in the absence of qualifiers. Extraordinary, however, is quite often used in a negative or neutral way. See updated answer. – terdon Mar 7 '15 at 15:42
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    The examples such as "extraordinarily bad, stupid, etc." still show a usage that implies "to a greater extent than normal," rather than "to a lesser extent." A greater extent of "bad" or "stupid" is negative, but still within the meaning of "extraordinary" as "more so than usual," rather than "less so." That having been said, what we now call "special needs children" have been called in medical literature "exceptional," implying less capability than most children have, but that's a fairly archaic usage. – Steven Littman Mar 7 '15 at 21:53

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