shrewd

Meanings

1. Showing clever resourcefulness in practical matters.
2. Artful, tricky or cunning.
3. streetwise, street-smart.
4. Knowledgeable, intelligent, keen.
5. Nigh accurate.
6. Severe, intense, hard.
7. Sharp, snithy, piercing.
8. Bad, evil, threatening.
9. Portending, boding.
10. Noxious, scatheful, mischievous.
11. Abusive, shrewish.
12. Scolding, satirical, sharp.

Etymology

From Middle English schrewed (“depraved; wicked”, literally “accursed”), from schrewen (“to curse; beshrew”), from schrewe, schrowe, screwe (“evil or wicked person/thing”), from Old English sċrēawa (“wicked person”, literally “biter”). Equivalent to shrew + -ed. More at shrew. The sense of "cunning" developed in early 16ᵗʰ c., gradually gaining a positive connotation by 17ᵗʰ c.