c. 1300, "wicked, evil," from shrewe "wicked man" (see shrew). Compare 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.