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.
- beyond what is usual, ordinary, regular, or established
- exceptional in character, amount, extent, degree, etc.; noteworthy; remarkable
- forming an exception or rare instance; unusual; extraordinary
- unusually excellent; superior
- prominent; conspicuous; striking
- 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?
Best Answer
Mostly, but not necessarily. Here are some examples where they have negative connotations:
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:
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:
From an article in Forbes magazine:
From the Free Dictionary's definition of atrocious:
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.