gangster n.

from Old English gang "a going, journey, way, passage," and Old Norse gangr "a group of men, a set," both from Proto-Germanic *gangaz (source also of Old Saxon, Old Frisian, Danish, Dutch, Old High German, German gang, Old Norse gangr, Gothic gagg "act of going"), of uncertain origin, perhaps from PIE root *ghengh- "to step" (source also of Sanskrit jangha "shank," Avestan zanga- "ankle," Lithuanian žengiu "I stride"). Not considered to be related to go.

The sense evolution is probably via meaning "a set of articles that usually are taken together in going" (mid-14c.), especially a set of tools used on the same job. By 1620s this had been extended in nautical speech to mean "a company of workmen," and by 1630s the word was being used, with disapproving overtones, for "any band of persons traveling together," then "a criminal gang or company" (gang of thieves, gang of roughs, etc.). By 1855 gang was being used in the sense "group of criminal or mischievous boys in a city." In American English, especially of slaves working on plantations (1724). Also formerly used of animal herds or flocks (17c.-19c.). Gangway preserves the original sense of the word, as does gang-plank.

Old English -istre, from Proto-Germanic *-istrijon, feminine agent suffix used as the equivalent of masculine -ere (see -er (1)). Also used in Middle English to form nouns of action (meaning "a person who ...") without regard for gender.

The genderless agent noun use apparently was a broader application of the original feminine suffix, beginning in the north of England, but linguists disagree over whether this indicates female domination of weaving and baking trades, as represented in surnames such as Webster, Baxter, Brewster, etc. (though modern spinster probably carries an originally female ending).

Also compare whitester "one who bleaches cloth;" kempster (c. 1400; Halliwell has it as kembster) "woman who cleans wool." Chaucer ("Merchant's Tale") has chidester "an angry woman" (the 17c. had scoldster). Also compare Middle English shepster (late 14c.) "dressmaker, female cutter-out," literally "shapester," sleestere (mid-15c.) "murderess, female killer" ("slay-ster"). Sewster "seamstress" (Middle English seuestre, late 13c. as a surname, also used of men) is still in Jonson but was obsolete or provincial after 17c. In Modern English, the suffix has been productive in forming derivative nouns (gamester, roadster, punster, rodster "angler," etc.).

rap style generally credited to West Philly hip hop artist Schoolly D, but as for the word itself, his "Gangster Boogie" (1984) used the conventional spelling; NWA was spelling it gangsta by 1988.