Etymology
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ruffian (n.)

1530s, "a boisterous, brutal fellow, one ready to commit any crime," from French rufian "a pimp" (15c.), from Italian ruffiano "a pander, pimp," of uncertain origin, perhaps from a Germanic source related to rough (adj.), but Dutch roffiaan, German Ruffian are said to be from French. Whatever its ultimate source, the English meaning of the word might have been influenced by the similarity of the sound to rough. Related: Ruffianly.

The Romanic words (such as Medieval Latin ruffianus, Provençal rufian, Catalan rufia, Spanish rufian) preserve the sense of "protector or owner of whores," a sense occasionally met in English in 17c. For sense evolution in English, compare bully (n.). Related: Ruffianage; ruffianhood; ruffianism.

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rough (n.)

c. 1200, "broken ground, a rough surface," from rough (adj.). From 1640s as "the disagreeable side of anything." The meaning "a rowdy" is attested by 1837, but Century Dictionary calls this perhaps rather an abbreviation of ruffian conformed in spelling to rough. The specific sense in golf, in reference to the ground at the edge of the greens, is by 1901.

Phrase in the rough "in an unfinished or unprocessed condition" (of timber, etc.) is from 1620s, in rough diamond "diamond in its natural state," which was used figuratively, of persons, by 1700, hence diamond in the rough (by 1874 of persons, in the figurative sense "one whose good character is somewhat masked by rough manners and want of education or style").

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tough (n.)
"street ruffian," 1866, American English, from tough (adj.).
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cut-throat (n.)

also cutthroat, "murderer, ruffian, assassin," 1530s, from cut (v.) + throat (n.). As an adjective, "cruel, murderous," from 1560s. Of card games from 1823. For construction, compare daredevil.

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plug-ugly (n.)

"city ruffian, one of a gang who assaulted people and property in mid-19th century American cities," 1856, originally in Baltimore, from plug (n.), the American English slang name for the tall, silk stovepipe hats then popular among young men, + ugly. Sometimes as the name of a specific gang, but often generic.

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bully (n.)

1530s, "sweetheart," a term of endearment applied to either sex, of uncertain origin; perhaps from Dutch boel "lover; brother," which probably is a diminutive of Middle Dutch broeder "brother" (compare Middle High German buole "brother," source of German Buhle "lover;" see brother (n.)).

Meaning deteriorated 17c. through "fine fellow" and "blusterer" to "harasser of the weak" (1680s, from bully-ruffian, 1650s). Perhaps this was by influence of bull (n.1), but a connecting sense between "lover" and "ruffian" might be "protector of a prostitute," which was one sense of bully (though it is not specifically attested until 1706). "Sweetheart" words often go bad in this way; compare leman, also ladybird, which in Farmer and Henley ("Slang and Its Analogues") is "1. A whore; and (2) a term of endearment." Shakespeare has bully-rook "jolly comrade."

The adjective meaning "worthy, jolly, admirable" is first attested 1680s, and preserves an earlier, positive sense of the word. It enjoyed a popularity in late 19c. American English, and was used from 1864 in expressions, such as bully for you! "bravo!"

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sandbag (v.)

also sand-bag, 1860, "furnish (a riverbank, etc.), with sandbags," from sandbag (n.).

The meaning "pretend weakness" is by 1970s perhaps extended from the poker-playing sense of "refrain from raising at the first opportunity in hopes of raising more steeply later" (1940), which perhaps is from sandbagger in the sense of "bully or ruffian who uses a 'sandbag' (in the sense of a cosh or sap) as a weapon to knock his intended victim unconscious" (1882). Hence "to fell or stun with a blow from a sandbag" (1887). Related: Sandbagged; sandbagging.

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roister (v.)

"bluster, swagger, be bold, noisy, vaunting, or turbulent," 1580s, from an obsolete noun roister "noisy, uncontrollable bully" (1550s, displaced or lost when roisterer began to be used, by 1745; Johnson still has roister as the main form of the noun), from French ruistre "ruffian," from Old French ruiste "boorish, gross, uncouth," from Latin rusticus "rough, coarse, awkward," literally "of the country" (see rustic (adj.)). Ralph Royster-Doyster is the title and lead character of what is or was sometimes called the first English comedy (Nicholas Udall, 1555). Related: Roistered; roistering; riosterous; roisterously.

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droog (n.)
"gang member, young ruffian," a transliteration of the Russian word for "friend," introduced by English novelist Anthony Burgess in "A Clockwork Orange" (1962). The Russian word comes from Old Church Slavonic drugu "companion, friend, other" (source of Bohemian drug "companion," Serbo-Croatian drugi "other"), which belongs to a group of related Indo-European words (such as Lithuanian draugas "friend, traveling companion;" Gothic driugan "do military service," ga-drauhts "soldier;" Old Norse drott, Old English dryht, Old High German truht "multitude, people, army") apparently with an original sense of "companion."
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ribald (adj.)

"offensively abusive, wantonly irreverent, coarse, obscene," of persons, conduct, speech, etc., c. 1500, from obsolete noun ribald, ribaud "a rogue, ruffian, rascall, scoundrell, varlet, filthie fellow" [Cotgrave], mid-13c. (late 12c. as a surname), attested from late 14c. in the sense of "one who uses offensive or impious language, one who jests irreverently."

This is from Old French ribaut, ribalt "rogue, scoundrel, lewd lover," also as an adjective, "wanton, depraved, dissolute, licentious," a word of uncertain origin, perhaps (with suffix -ald) from riber "be wanton, sleep around, dally amorously," from a Germanic source (compare Old High German riban "be wanton," literally "to rub," possibly from the common euphemistic use of "rub" words in venery, from Proto-Germanic *wribanan from PIE root *wer- (2) "to turn, bend").

Other early adjectival forms were ribaldous "riotous, unruly" (c. 1400); ribaldy (early 15c.).

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