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I am puzzled by the fact that while most earlier usage of лихой have distinctly negative connotations (лиходей, лихой человек is most certainly a villain, лихие времена - bad times, лихоимство - deeds related to extortion, blackmail or racket, лихорадка - fever), more recent meanings seem to be much more at the positive side, like лихость - bravery, dare, лихой скакун - something like dashing charger, or bold steed, "Лихо!" - "Cool!"

Does anybody know how this drastic shift of meaning occurred? Or I am wrong and these polar meanings existed from the beginning? If yes, how to explain this?

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    Similar question: russian.stackexchange.com/q/20609/2104 – Sergey Slepov Mar 29 at 19:17
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    And, in English, how come is "Hot!" a synonym of "Cool!"? :) – Alexander Mar 29 at 20:08
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    @Alexander english.stackexchange.com/a/43066/2038 – Quassnoi Mar 31 at 3:02
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    About negative connotation it's not only ancient сonotation... also see "Лихо Одноглазое" :) About positive connotation.... I don't say specifically, but the mechanism here is clearly the same as for situations when someone is called a "pirate" or "corsair" ... in romantic style:> Although there was nothing romantic about them in fact. Sometimes you can hear "you are evil!" :) - but in fact it means admiration in specifical situation, and the irony here refers only to the very concept of "evil" and situation, not for the recipient :> youtu.be/_ZW-AZ2mNeA :> –  Пилум Apr 5 at 21:46
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    Such shifts in meaning happen not only in Russian: in English, the word "terrific" used to mean "horrible", "awful", not it's more like "great", "very good". The word "sick" is undergoing the same transformation now, e. g. from "a sick person" to "dude, this is sick!" In Japanese, the word "sugoi" changed its meaning similar to "terrific", from "horrible" to "wonderful". – Headcrab Apr 6 at 3:51
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The original meaning of the etymon was "excess, surplus". It is related to the words лишний "excess, spare" and лихва "loan interest".

A word meaning "spare, excess" is a common metaphor for "evil, bad". Compare the French word excès, literally "excess", which also means "an outburst, something done out of boundaries", which is also the source for the Russian word эксцесс. Also compare English "odd" that also means "strange, eccentric".

The meaning of "dashing, audacious" is most probably secondary and derived from "evil", similar how злой до работы means "eager to work", but I could not find any confirmation for this.

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Происхождение слова "лихой"

Этимологический онлайн-словарь Шанского Н. М. приводит два направления развития значений этого слова:

Лихо́й. Общеслав. Того же корня, что греч. leiksanon «остаток». Суф. производное (суф. -s-) от *leik- «оставлять» (см. лишний).

Исходно — «лишний, обильный» > «хороший» > «смелый, удалой» и т. д., с одной стороны, и «лишний, обильный» > «нечетный» > «нежелательный» (в отличие от четного числа) > «несчастный, плохой, злой».

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  • Seems like so far yours is the only acceptable answer. Still, let me wait a bit more. I do find convincing the connection to "left" and "leftover", but even if one understands лишний in the context of в избытке, still I am not so sure how to go from there to хороший, and even less how to arrive at смелый, удалой... – მამუკა ჯიბლაძე Apr 3 at 14:23
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I would like to add, that the recent meaning of "лихой" more like - causing a great effect, and not always in a positive way. For example: "Это был лихой день" means that the day was full of events that causing a great effect, good or bad depends on a context.

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  • Interesting... is it some slang usage or it can be found in some recent literature too? – მამუკა ჯიბლაძე Apr 17 at 5:49
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    I think it is slang usage. For example: Молодежь распивает шампанское, затем в комнату вносят еще несколько ящиков спиртного. Особое рвение в употреблении алкоголя проявляет Ксюша. Начинается лихая гулянка. The phrase "лихая гулянка" means that the party was very exciting, with a lot of events, not boring. Text is from plot description of Килиманджара movie. – OlegJdll Apr 17 at 6:06
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I would like to add to the Quassnoi's answer that excessiveness can sometimes be bad and sometimes be good. I can't agree that 'лихость' can be translated as 'bravery' or 'dare'. Of the words you mentioned I find 'dashing' and 'bold' much closer to an idea rendered by a word 'лихой'. Bravery is a virtue and can't be excessive. One can be excessively bold, though.

So adverb 'лихо' may have positive or negative connotation depending on the context.

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Because if a man is aggressive it is sexually attractive to women (especially, Russian ones). Thus, something bad for the victim is good for the sexual partner.

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