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I searched in The American Heritage Dictionary of the English Language for win’s definitions to see it’s usage but I couldn’t figure out whether it can be used sarcastically with a negative connotation or not.

Ex:

Can I say, “I won lots of down votes”?

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    it can be used sarcastically, for sure (your example makes lots of sense.) I can't quite figure out what you mean by "pejoratively." – hunter Jun 19 '14 at 8:01
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    @hunter, just wanted to say with a negative connotation but maybe pejorative is not the appropriate word. – Lucian Sava Jun 19 '14 at 8:07
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    Virtually, any words can be used ironically. I guess I prefer saying ironically to sarcastically here; however, it would depend on the speaker's intention. See also: en.wikipedia.org/wiki/Irony#Verbal_irony_and_sarcasm. – Damkerng T. Jun 19 '14 at 9:38
  • @DamkerngT., It’s still arguably as said in the link you provided. Thank you, it's a good link indeed. – Lucian Sava Jun 19 '14 at 9:47
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Sure you can. Sarcasm is essentially saying the opposite of what you mean, but in a certain tone which reveals your true feelings. There's no reason you can't employ win in this fashion. Winning something has positive polarity (no or not doesn't appear in the sentence) but it doesn't entail positive emotions (the result might make you feel bad).

Your example I won lots of downvotes does just that. You've "won" (been awarded or successfully acquired) something you don't want, so the outcome is undesirable.

You might also use win sarcastically to describe a hollow or meaningless victory:

I heard you won the tournament, great job!
Oh yes, I won a crushing victory... because nobody else showed up to compete.

The implication here is that the second person didn't really win at all as there was no competition. There's a negative connotation because joining a tournament and winning by default tends to make one quite cranky.

Someone extremely cruel might say you won! very sarcastically to someone else finishing in last place or performing exceptionally poorly. Similarly, someone doing something trivial or stupid and acting as if they had made a great accomplishment might receive a dry remark of congratulations, you win the prize.

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Good question. The word 'win' can be used in negation if the competition or the contest is of winning something bad or badly!

The sentence I won lots of down votes is okay if the goal was to win the downvotes.

Originally, the word is used in a positive way. However, in some contexts, it's used to mention getting/gain something but still in a negative way. An example:

Representative Richard A. Gephardt of Missouri spent $18 million in his presidential campaign, which ended after he won fewer than 14,000 votes in Iowa. That works out to about $1,300 per vote, which would be enough to buy every voter a chicken, a pot and a full-featured stove.

He won the title of the worst actor and constructions the like use win in a negative way but ultimately due to the nature of the competition/concept, it's actually positive. I daresay, win is always positive.

A tongue-in-cheek remark in the headlines that uses 'win' but sarcastically:

Razzies: Will and Jaden Smith "win" worst actor honors

  • Should we always use quotation marks like in the link you provided to draw attention that it’s used sarcastically or is just a matter of style? – Lucian Sava Jun 19 '14 at 9:15
  • @LucianSava It's a matter of style and emphasis. Quotes make sarcasm explicit and obvious. Sometimes we want to be more subtle about it. The catch is that sarcasm can be difficult to detect in written English, because it makes heavy use of non-literary components like tone of voice or body language. – Esoteric Screen Name Jun 19 '14 at 9:29
  • certainly, it's just a matter of style. – Maulik V Jun 19 '14 at 9:55
  • The sentence I won lots of downvotes is okay even if the intent is to avoid downvotes. For example: "I decided to schedule the board meeting on Friday afternoon, at 4 PM." Answer: "I'll bet that won you a lot of enemies!" That works, even if the meeting's organizer wasn't trying to lose friends. – J.R. Jun 19 '14 at 16:08

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