shrewd

c. 1300, Middle English schrewed (“depraved; wicked”, literally “accursed”), from schrewen (“to curse; beshrew”), from schrewe, schrowe, screwe (“evil or wicked person/thing”), from Old English *scrēawa (“wicked person”, literally “biter”). Equivalent to shrew +‎ -ed. More at shrew.

The sense of "cunning" developed in early 16^th c., gradually gaining a positive connotation by 17^th c.

• enPR: shro͞od, IPA^(key): /ʃɹuːd/

• Rhymes: -uːd

shrewd (comparative shrewder, superlative shrewdest)

1. Showing clever resourcefulness in practical matters.
2. Artful, tricky or cunning.
3. (informal) Streetwise.
   • 2003, Ron Ross, Bummy Davis vs. Murder, Inc, page 287:

     Willie is very aware of this fact and lets Johnny Attell know that there is a fly in the ointment, and Johnny, who is a very shrewd article, has his chauffeur drive him to Bradford Street so he can change the kid's mind.

4. Knowledgeable, intelligent, keen.
   • 2011 November 10, Jeremy Wilson, “tEngland Under 21 5 Iceland Under 21 0: match report”, in Telegraph‎:

     The most persistent tormentor was Alex Oxlade-Chamberlain, who scored a hat-trick in last month’s corresponding fixture in Iceland. His ability to run at defences is instantly striking, but it is his clever use of possession that has persuaded some shrewd judges that he is an even better prospect than Theo Walcott.

5. Nigh accurate.

   a shrewd guess

6. Severe, intense, hard.

   a shrewd blow, or assault

7. Sharp, snithy, piercing.

   a shrewd wind

8. (archaic) Bad, evil, threatening.
   • 1596-97, William Shakespeare, The Merchant of Venice, Act III Scene ii:

     Portia:

     There are some shrewd contents in yon same paper,

     That steals the colours from Bassanio's cheek:

     Some dear friend dead; else nothing in the world

     Could turn so much the constitution

     Of any constant man. What, worse and worse!— […]

9. (obsolete) Portending, boding.
10. (archaic) Noxious, scatheful, mischievous.
11. (obsolete) Abusive, shrewish.
12. (archaic) Scolding, satirical, sharp.
    • 1599, William Shakespeare, Much Ado About Nothing, Act II Scene i:

      Leonato: By my troth, niece, thou wilt never get thee a husband, if thou be so shrewd of thy tongue.

• shrewdly
• shrewdness