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c.1300, "wicked, evil," from shrewe "wicked man" (see shrew). Cf. crabbed from crab (n.), dogged from dog (n.), wicked from witch (n.). The sense of "cunning" is first recorded 1510s. Related: Shrewdly; shrewdness. Strutt's "Sports and Pastimes of the People of England" (1801) has a shrewdness of apes for a company or group of them. Shrewdie "cunning person" is from 1916.