How offensive is the word Bastard? And when did it become more of an offense than a term used for child out of wedlock?
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I suppose it's an Old phrase from used in French bastart. In medieval Latin it called bastardus, or probably bastum which is the same as "pack saddle," the idea probably being of a child produced from a relationship with a traveler.
Bastard is a very old term of French origin. The way we use is today as a general term of offence is from 1830:
"illegitimate child," early 13c., from Old French bastard (11c., Modern French bâtard), "acknowledged child of a nobleman by a woman other than his wife," probably from fils de bast "packsaddle son," meaning a child conceived on an improvised bed (saddles often doubled as beds while traveling), with pejorative ending -art (see -ard).
Not always regarded as a stigma; the Conqueror is referred to in state documents as "William the Bastard." Figurative sense of "something not pure or genuine" is late 14c.; use as a vulgar term of abuse for a man is attested from 1830. As an adjective from late 14c. Among the "bastard" words in Halliwell-Phillipps' "Dictionary of Archaic and Provincial Words" are avetrol, chance-bairn, by-blow, harecoppe, horcop, and gimbo ("a bastard's bastard").
Bastard is an offensive expression but it can be used, with care, as a jocular expression:
(informal, offensive) an obnoxious or despicable person
(informal, often jocular) a person, esp a man: lucky bastard
(informal) something extremely difficult or unpleasant: that job is a real bastard.