Chutzpah
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Chutzpah is the quality of audacity, for good or for bad. The word derives from Yiddish khutspe used by Jewish people originally from Eastern Europe, which in turn derived from Hebrew חוצפה universal to Jews throughout history, and by now it has taken on wider usage having been spread through film, literature and television.
Though originally referring to a negative quality, the word chutzpah has developed some interesting positive connotations in English usage. Whereas in Hebrew chutzpah is used indignantly, to describe someone who has outstepped the boundaries of accepted polite behaviour for selfish reasons, in English chutzpah can be spoken in admiration of non-conformist but gutsy audacity. Leo Rosten in The Joys of Yiddish defines chutzpah as "gall, brazen nerve, effrontery, incredible 'guts,' presumption plus arrogance such as no other word and no other language can do justice to."
One humorous definition of chutzpah is generally given as: "a boy is on trial for murdering his parents, and he begs of the judge leniency because he is an orphan."
Controversial lawyer Alan Dershowitz entitled his bestselling book of essays Chutzpah, a title many find to be highly befitting.
Though there are several near-synonyms for chutzpah, none of them capture the particular ambivalent blend of the Yiddish.
Some nice tries: