Etymology
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picaroon (n.)

1620s, "rogue, thief, cheat, adventurer; pirate, sea-robber; small pirate ship," from Spanish picaron, augmentative of picaro "rogue" (see picaresque); also see -oon.

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trick (n.)

early 15c., "a cheat, a mean ruse," from Old North French trique "trick, deceit, treachery, cheating," from trikier "to deceive, to cheat," variant of Old French trichier "to cheat, trick, deceive," of uncertain origin, probably from Vulgar Latin *triccare, from Latin tricari "be evasive, shuffle," from tricæ "trifles, nonsense, a tangle of difficulties," of unknown origin.

Meaning "a roguish prank" is recorded from 1580s; sense of "the art of doing something" is first attested 1610s. Meaning "prostitute's client" is first attested 1915; earlier it was U.S. slang for "a robbery" (1865).

To do the trick "accomplish one's purpose" is from 1812; to miss a trick "fail to take advantage of opportunity" is from 1889; from 1872 in reference to playing the card-game of whist, which might be the original literal sense. Trick-or-treat as a children's Halloween pastime is recorded from 1927 in Canada. Trick question is from 1907.

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hoax 
1796 (v.) "ridicule; deceive with a fabrication," 1808 (n.), probably an alteration of hocus "conjurer, juggler" (1630s), also "a cheat, impostor" (1680s); or else directly from hocus-pocus. Related: Hoaxed; hoaxing.
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jilt (v.)
"to deceive (especially after holding out hopes), discard after encouraging," 1670s; earlier "to cheat, trick" (1660s); of uncertain origin (see jilt (n.)). Related: Jilted; jilting.
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fun (n.)
"diversion, amusement, mirthful sport," 1727, earlier "a cheat, trick" (c. 1700), from verb fun (1680s) "to cheat, hoax," which is of uncertain origin, probably a variant of Middle English fonnen "befool" (c. 1400; see fond). Scantly recorded in 18c. and stigmatized by Johnson as "a low cant word." Older senses are preserved in phrase to make fun of (1737) and funny money "counterfeit bills" (1938, though this use of the word may be more for the sake of the rhyme). See also funny. Fun and games "mirthful carryings-on" is from 1906.
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fob (v.)
"to cheat," late 14c., from obsolete noun fobbe "cheat, trickster" (late 14c.), which perhaps is from Old French forbeter "to deceive, trick, dupe." Alternative etymology holds that the word is perhaps related to German foppen "to jeer at, make a fool of" (see fop); or from German fuppen, einfuppen "to pocket stealthily," which would connect it to fob (n.).

Meaning "to put or shift off (something) by pretense" is from 1650s; to fob (someone) off "put him off deceitfully" is from 1590s. Related: Fobbed; fobbing.
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gold-brick (n.)
"gold in the form of a brick," 1853, from gold (adj.) + brick (n.). Meaning "shirker" is from 1914, World War I armed forces slang, from earlier verb meaning "to swindle, cheat" (1902) from the old con game of selling spurious "gold" bricks (attested by 1881).
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finagle (v.)
"get dishonestly or deviously," 1926, American English, possibly a variant of English dialectal fainaigue "to cheat or renege" (at cards), which is of unknown origin. Liberman says finagle is from figgle, phonetic variant of fiddle "fidget about," frequentative of fig. Related: Finagled; finagling.
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jape (n.)
mid-14c., "a trick, a cheat;" late 14c. "a joke, a jest; a frivolous pastime, something of little importance" (late 14c.); see jape (v.). By 1400 also "depraved or immoral act; undignified behavior; bawdiness." Related: Japery "jesting, joking, raillery, mockery" (mid-14c.).
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take (n.)
1650s, "that which is taken," from take (v.). Sense of "money taken in" by a single performance, etc., is from 1931. Movie-making sense is recorded from 1927. Criminal sense of "money acquired by theft" is from 1888. The verb sense of "to cheat, defraud" is from 1920. On the take "amenable to bribery" is from 1930.
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