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I looked it up in Wiktionary, and I've found out that the term "screw over" means "to cheat someone, or ruin their chances in a game or other situation."

I want to know how that term came about? What is its origin? And what does "over" mean here?

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I'm not sure anyone has researched this, but it is presumably related to the phrasal verb "fuck over." Green's dictionary of slang dates "fuck over" back to at least 1965. John Strachey's The End of Empire used it in 1960, though, so it appears to be older.

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screw as such is of a somewhat uncertain origin. The mechanical sense could be an allusion to pig-tails, inasmuch as screws have windings. In this sense, to screw over can be torturing a piece of gear, destroying the nut. As a metaphor, this could easily mean to overstay one's welcome. That would be a plausible null hypothesis.

However, there is a range of German idioms with one refering to scheren "to shear, shave" collocated with über "over", though that's more often barbieren: jemanden über den Löffel barbieren "to screw somebody over".

Röhrich (Redewendungen) explains this, that barbers were generally not deemed trustworthy, and refers to a practice of shoving a spoon under the cheek of the person to be shaved so as to create a smooth surface in the case when there are no teeth to do the job. This doesn't impress me as very believable. Anyway, it means the idiom has a history because Röhrich didn't make it up. If the teeth bit is an implausible folkish element, the practice may simply serve to speed up the process—a quick job, perhaps a botch job.

It is in both cases easier to start from a common sense of cutting—indeed to cut somebody, to skim, to card, to shave a few coins (literally)—rather than to rely on colorful imagery.

There are so many idioms which use über respectively over to mark exaggeration that it may well be coincidence anyway. The same can be said for the sexual euphemism. I'll be fucked if that was on the books in time (NB: ~ up must mean open, as of a wound, which are homophone in German auf).

Besides, Yiddisch has schachern to cover a range of senses such as vb. "barter", adj. "greedy", from Hebrew sāḥar. I can only wonder what its result would be in English because both thiefscant and antisemitic slurs make liberal use of lexical replacement. E.g. German schröpfen "to bloodlet", related to scrape, now also means "to make pay through the nose" as does the literal verbal phrase jmd. zur Ader lassen.

The phonology would be quite a stretch because argot intentionally obscures; at best it connects back to the barber, quacks and other charlatans. Besides, Low German schäkern "to flirt" (and more?) likely belongs to the sense of "barter" vel sim. And, to check somebody out could belong to a related idiom though it has plausible deniability.

If you can find screwy in a sense of "greed", that would be darn close. So far, there is at least a possible parallel to the sexual euphemism. I mean, I get to nail, but to screw? Come on, what are you doing!? Of course this type of coincidence has to be deliberate.

From the word shape it is obvious that sk is at any rate not inherited from Old English, because that would become sh.

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