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"The worst student" is the student who is bad at things. In this case, "worst" simply describes the noun.

Following this logic, your "worst enemy" would be the person who is very bad at being your enemy, thus is actually your best friend. Your "worst enemy" is actually the enemy who is very good at being your enemy. Thus, in this context, "worst" acts to amplify the inherent negative intent of the noun. "Worst disaster" would be another example of this.

Is this just a matter of context or there some science behind the interprettation of a negative adjective applied to a negative noun?

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Don't confuse English language with the mathematical theory. The adjective worst qualifies the noun enemy with even more bad values. So, a worst enemy is more dangerous than a normal enemy.

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  • +1; This seems to be the most concise answer here. I would add that it may help the hurt on your brain if you think of the "worst" affecting the well being of the person speaking. My worst enemy is the enemy that is worst for me. Obviously, this doesn't apply to all cases of "worst," but it may help shift the perspective a bit.
    – MrHen
    Mar 21, 2011 at 18:19
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    As mentioned elsewhere, this question arose while discussing English with my daughter (9 yo). I think I can use this discussion to win the argument - isn't that what parenthood is all about?
    – dave
    Mar 22, 2011 at 0:24
  • A better "mathematical" way to think of it is that "worst" is not a multiplier but an added constant. If something, say "student", is said to be worth 5 "goodness points", and putting "worst" on subtracts 10, then it is reduced to -5 as "worst student", so bad. Doing that to "enemy" which is already worth negative (bad) points, just makes it more negative. But the point is that "worst" isn't doing anything different to the word "enemy" than it is doing to the word "student". It's not like it's acting like a negation in one case and an affirmation in another.
    – The_Sympathizer
    Jan 26, 2017 at 7:32
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The "science behind it" is pragmatics: if you use a word like "worst" you've almost certainly got negative thoughts around.

In principle you might be able to concoct an example of what you're suggesting, but I haven't managed to think of a way. What you can just about do is get "worst" to mean "least effective", as in 

"I've ranked Batman's enemies in terms of how much trouble they give him. 
 The Penguin does best, and Catwoman is easily the worst"

but even there you need to set up quite a lot of context to avoid "worst" suggesting "nastiest".

[I'm not advancing the quote as an opinion, by the way: it's just an example!]

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  • Yeah, this answer provides good reasoning. Language is perhaps more often emotive than mathematical.
    – Noldorin
    Mar 21, 2011 at 17:46
  • I don't think you need to resort to pragmatics. This is a simple question of what worst means. The question starts out with a slight misunderstanding of what it means, based on a single example, and from that mistake we logically proceed to weirdness.
    – Jason Orendorff
    Mar 21, 2011 at 17:55
  • @Jason Orendorff: If this were a "simple" question of the meaning of worst then there wouldn't be a number of conflicting answers, as well as an answer that had 9 upvotes that was deleted by the author when he had second thoughts about it! Based on the context-free meaning of worst, it does not make sense to use worst in "worst enemy". "Worst enemy" does not entail someone that is evil or corrupt like "the worst kind of person" does; my worst enemy could be someone completely honest who is my rival and always causes me frustration. You have to "resort" to pragmatics.
    – Kosmonaut
    Mar 21, 2011 at 20:32
  • By "simple" I just meant there was a more mundane explanation.
    – Jason Orendorff
    Mar 21, 2011 at 21:07
  • @Kosmonaut Pragmatics surely contribute some shade of meaning here, but a dictionary definition suffices to rule out the specific interpretation the question actually asks about.
    – Jason Orendorff
    Mar 21, 2011 at 21:38
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I agree with Colin Fine that this is pragmatically guided; we use the negative modifier because we want to make this negative concept more negative. As it is a matter of pragmatics, the construction cannot be deconstructed on a purely semantic basis in order to justify its use.

So, the worst president will be someone who is the most inferior at being president, but the worst dictator is one who will, purely logically speaking, be the "best" at being a dictator.

This is not only done in the case of "worst". Another example would be:

He had a very bad injury.

Actually, the injury is quite "good" — in the sense that the injury is superior to other injuries — but an injury is a negative thing, so we use "bad" rather than "good".

Note that in some dialects a person can say "he got hurt real good" — here the "logical" good is used, but it basically means the same thing as "he got hurt real bad" (with the negatively agreeing "bad"). Since neither use is sarcastic, if "good" = "good" and "bad" = "bad" regardless of pragmatics, then these two sentences should not mean the same thing.

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  • @cindi: Neither is "bad injury"; it works just like "worst enemy". The other part with "good" is only dependent on dialect.
    – Kosmonaut
    Mar 21, 2011 at 20:16
  • Stephen Hawking: "The greatest enemy of knowledge is not ignorance, it is the illusion of knowledge."
    – John M. Landsberg
    Mar 28, 2013 at 5:12
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"Worst" has a very broad meaning and in this case means something like, "most negative". The meaning seems more intuitive than logical to me, just like most idioms.

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The "worst" also means most corrupt, bad, evil, or ill . So your worst enemy could be your most evil enemy. But this is untrue in many cases and here come other meanings of the word: most unpleasant and most unfavorable. Therefore, your worst enemy even being a very good person can be the most unpleasant, unfavorable or simply the most unfriendly enemy to you.

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  • @Kosmonaut: what do you think about this one?
    – Edwin Ross
    Mar 21, 2011 at 17:05
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I think this is pretty simple: the many meanings of bad and worst overwhelmingly tend toward horribleness and undesirability, not incompetence or logical negation. So given the choice between the two possible interpretations of worst enemy, people will naturally choose the one where the enemy is especially horrible or undesirable.

Sometimes, as in the worst dentist in the county, it happens that the undesirable quality is incompetence. But I can't think of an example where bad means incompetent in a benign sense. You occasionally see something like “Her delightfully bad singing won me over”, but it seems like there's some intentional irony there.

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  • No, a bad example is undesirable. It's not benign.
    – Jason Orendorff
    Mar 21, 2011 at 17:57
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In another case, "greatest" and "best" are not interpreted the same as well.

He was my greatest enemy.

This is often interpreted as "most challenging" or the one who was my enemy the most.

He was my best enemy.

This could possibly be interpreted almost as a joke. My best enemy was an enemy I found funny. "The best enemy to have."

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The meaning is often seeming obvious and clear, but is contextual rather than strictly logical, and can be subjective and up to the speaker to decide and to communicate effectively.

To use your example, "worst" in "the worst student" doesn't necessarily "simply describe the noun". e.g. it could be either something like:

"Ralph was the worst student this term, attending only half the classes and failing the test." (i.e. he was worst at the class requirements)

or

"Of all the ill-mannered students, Jason was the worst student Mathilda had ever encountered." (i.e. Jason was the worst behaved)

A clearer example of this possibility might be:

"Sam received a bad blow to the face." (it's bad because the speaker sympathizes with Sam)

vs.

"Bob landed a good blow on the monster's wing." (it's good because the speaker is siding with Bob)

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