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The English word "shrewd" (as in "a shrewd businessman") describes someone who is sharp, clever, crafty, or cunning. For example, a shrewd businessman might come up with a coupon offer that seems attractive, but when you read the fine print you realize that it is carefully designed to be difficult to redeem and results in the biggest possible profit for the owner.

Is there a Spanish word that carries all these connotations? Does astuto only cover the idea of being intelligent, or does it also imply the sly cunning that "shrewd" does?

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We use in general "negociante hábil" –  Leandro Jun 29 '12 at 16:53
    
Quizás embaucador –  Juanillo Jun 29 '12 at 19:09
    
an "embaucador" is a cheater. –  Leandro Jun 29 '12 at 19:29

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I think that it would be translated perfectly as "sagaz".

Se aplica a la persona que es hábil e inteligente y se da cuenta de lo que puede ocurrir

"Astuto" would be just "clever", but "sagaz" would include the sharper and deeper connotations like your "but when you read the fine print you realize that it is carefully designed to be difficult to redeem and results in the biggest possible profit for the owner".

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This is the first time that I see this word, "shrewd". By doing a quick search in wordreference.com you can see that it does mean "astuto".

Now if you look for the definition of "astuto" it actually does not mean "intelligent" but the entry reads as:

astuto, ta adj. Hábil, sutil, sagaz

So in my opinion "astuto" would be used properly if you want to use it as calling someone "cunning".

For the sake of completeness, there was a TV show a long time ago, maybe during the 80s, called "Wise Guy" which was actually translated as "El Astuto".

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