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Ok, I am wondering whether "Streetwise" carries any negative meaning.

Streetwise(a): having the experience and knowledge necessary to deal with the potential difficulties or dangers of life in an urban environment. Source

But then, if you Google "streetwise thief", then it will show like 3000 results.

I wondered whether Streetwise person means "the ones who use his life experience and knowledge to deceive other people who are not streetwise"?

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    I've never read it to mean any kind of deceitful activity or intent, without other context. The only negative I can think of is that it might imply a lack of conventional education. A streetwise kid acquired his wisdom, and possibly knowledge, on the street. It also suggests a necessary level of cynicism and mistrust, which could be considered negative.
    – JHCL
    Commented Oct 13, 2015 at 9:34
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    Streetwise/streetsmart can be used in a derogative way when scholars with higher degrees such as PhD describes someone who has less degrees or without any degree. It all depends on the context. I don't think the word itself is negative.
    – user140086
    Commented Oct 13, 2015 at 9:37
  • Booksmart could plausibly be used in a similar way. Imagine you were discussing an awkward friend with somebody, and they used the word "booksmart" to describe them. If the context was right, that could be understood imply not intelligent in other ways.
    – James
    Commented Oct 13, 2015 at 11:28
  • In my opinion, while it is not blatantly pejorative, it does not usually carry a strong positive connotation. And it is sometimes used as a euphemism for being a prostitute or hustler.
    – Hot Licks
    Commented Oct 13, 2015 at 14:16

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Streetwise is not a derogatory term:

  • North American English also street-smart (informal)

  • having the knowledge and experience that is needed to deal with the difficulties and dangers of life in a big city.

    • Kids seem much more streetwise these days.

(OLD)

Streetwise:

  • Having the necessary knack, personality and instinct for survivgal in rough, urban environments.

    • Like all serial killers, he had the ability to sense vulnerability among potential victims; he didn't take the streetwise girls, he was after the younger women. (Ann Rule speaking about Gary Ridgway.)

  • Possessing a style that embodies the life and microculture located within urban settings, typically in the States.

    • You could tell from the way he spat old Tupac lyrics, loitering in the corner with his homies, flipping that Yankees cap on his head like he couldn't give a damn that he was streetwise enough to melt Will Smith.

(Wiktionary)

Streetsmart:

  • (adjective) familiar with the human condition as played out in an urban setting, US 1976. Street smarts (noun) intuitive understanding of human nature as played out in urban US reality.

(Patridge Slang Dictionary)

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