Etymology
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outwit (v.)

"to get the better of by superior wits, defeat or frustrate by superior ingenuity," 1650s, from out- + wit (n.). Related: Outwitted; outwitting. Middle English had a noun outwit "external powers of perception, bodily senses; knowledge gained by observation or experience" (late 14c.; compare inwit).

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outfox (v.)

"outwit, outdo in deception or cunning," 1939, from out- + fox. Related: Outfoxed; outfoxing.

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jockey (v.)
1708, "trick, outwit, gain advantage," from jockey (n.) perhaps in its former secondary sense of "horse trader" (1680s) and reflecting their reputation. Meaning "to ride a horse in a race" is from 1767. Related: Jockeyed; jockeying.
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stratagem (n.)

"artifice, trick," late 15c., from French strattegeme, stratagème "trick, especially to outwit an enemy" (15c.), from Italian stratagemma, from Latin strategema "artifice, stratagem," from Greek strategema "the act of a general; military stratagem," from strategein "to be a general, command," from strategos "general" (see strategy). Related: Stratagematic; stratagemical. The second -a- is a Romanic misspelling (compare Spanish estratagema).

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