Some words undergo severe changes in their lifetime. The word nice, for instance, started its life meaning flighty and foolish, and the word silly once meant happy and blessed.
The word shrewd has bounced all over the place, too. Originally, it meant depraved, wicked, and malignant. Now it’s considered a compliment, as in she’s a shrewd business owner.
From extremely evil, it softened to naughty when applied to children in the 16th century, although applied to animals, it still signified bad-tempered in a vicious way. Then, for some reason, it slowly began to take a more positive spin in 1520: “Seeming to be sheep, and serpently shrewd.” [Calisto & Melib. in Hazl. Dodsley I. 60] The comparison to a serpent still showed some negativity, but the swing to clever and astute was underway.
The word seems to have begun with the shrew-mouse, which medieval lore said would have a malignant effect on both man and beast if it came in contact. Its bite, it was believed, contained venom.
SIDEBAR: Animal Diversity Web -- the shrew
Now available from McFarland & Co.: Word Parts Dictionary, 2nd edition
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