I did a lot of research on internet regarding the connotation of word shrewd. It can have negative as well as positive connotation.It depends on the context of the passage. For instance,

A shrewd real estate agent

A shrewd business man

Another usage of shrewd is for decisions, policies, judgements etc. Well, I was looking for this particular usage on dictionary and found this. Second usage has confused me a bit as it is mentioned that shrewd activities are marked as artful and cunning practices. Now the word cunning has purely negative connotation. So I want to know how do native speakers use this word? Specially I am confused about its usage with activities. For Instance - a shrewd policy or a shrewd decision. An example for negative usage of shrewd could be this sentence

The union was known for its shrewd negotiating tactics. (calculating, underhanded)

On Twitter, he said it was a “brutal conspiracy and a shrewd scheme” that allowed Mr. Modi’s “suit-boot friends to convert their black money into white”.

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    It's a declining usage anyway, so as a learner you might want to take the easy way out and just ignore this word. But as you correctly say, connotation depends on the context. It also varies from person to person (for many different reasons). On average, if you see references to a shrewd policy or a shrewd decision, they'll be "approving". But as a question for ELL, it's Off Topic POB (Primarily Opinion-Based). May 11, 2020 at 11:41
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    @FumbleFingers Reinstate Monica...Sometimes I ask well researched questions and still they are downvoted. As a non-native speaker of english language my questions cannot match the question level of native speakers. Its disappointing sometimes.Now should I delete this question? May 11, 2020 at 13:03
  • Well, someone's upvoted my comment, but despite what I wrote there, I didn't vote to close the question myself (and so far nor has anyone else). I can understand you might want to delete the question if you're getting downvotes (which may reduce your reputation points, thus restricting your use of this site). But that's not happening, so I don't think you have any good reason for deleting it. Just because I wasn't very "encouraging" above doesn't mean you should abandon all hope! :) May 11, 2020 at 13:22
  • @FumbleFingers Reinstate Monica..I have decided to follow your first advice. As a learner I must learn to distinguish between what is useful and what is not. I am going to skip this word for now. One last question for you, Do you know any resource where I can look for words which are currently used. Any website or book will be best. May 11, 2020 at 14:37
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    @SudhirSharma I still don't agree that shrewd negotiating tactics are bad. They're good. I don't think that calculating is negative either. And I definitely disagree that underhanded has any place there as a synonym … As for "a brutal conspiracy and a shrewd scheme," that's just two different things. It doesn't mean they are equated with each other. For instance, something that combines both of my points is this: The philanthropist was known for her shrewd business savvy and investment in charities. Or: His cunning plan was smart, and good for everyone. May 11, 2020 at 17:10

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First, I disagree slightly with FumbleFingers. I believe shrewd is in regular usage. Per https://books.google.com/ngrams/graph?content=shrewd&year_start=1800&year_end=2008&corpus=17&smoothing=3&share=&direct_url=t1%3B%2Cshrewd%3B%2Cc0#t1%3B%2Cshrewd%3B%2Cc0, its usage has been slightly declining over the past 40 years, but it is, in no way, archaic.

On to the connotation. Shrewd does not imply underhanded or cheating. For example, a shrewd legislator isn't blackmailing people. She is using her knowledge of parliamentary procedure in order to increase her chances of getting her agenda passed into law. If you were of the opposite political party, you might crinkle your nose in disgust at her shrewdness, but only because she's not on your side.

Cunning is not a direct synonym, as cunning usually includes misrepresentation/lying, which shrewd usually does not include. For example, someone making $1 million selling vitamins that he implies helps with Covid 19 might be referred to as "cunning". Whereas a shrewd businessman would be someone who bought stock in Zoom the minute they heard of the outbreak. Both are making money on human misery, but there is, for most people, a distinct moral difference.

I would also agree with FumbleFingers that the phrase "shrewd businessman" might have a negative connotation for some, but that this has more to do with the "businessman" aspect. At least in the US, there is a significant portion of the population who see business as primarily exploitative, so someone who is very good at it must be morally questionable.

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