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The 5th definition of smooth in Macmillan:

showing disapproval relaxed and confident in a way that usually persuades people to do things. This word shows that you do not trust people like this

Steven's a bit too smooth for my liking.

a smooth operator (=someone you cannot trust)

However, I have run into examples like this:

We need to be really smooth in the meeting today if we want to close the deal.

He’s smooth! Did you see how he just got that girl’s phone number?

It doesn't look like smooth is used in a disapproving way.

What do you make of it?

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Yeah, I think the dictionary is applying negative connotations inappropriately here.

I agree with the relaxed and confident definition, but leave it at that; it can be used for either good or bad purposes.

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  • This point might be clearer given some contrast: "Steve is too smooth for my liking, but John is not smooth enough." The "smooth" could be replaced by "confident" or "competent". The sense of disapproval comes from that confidence or competence being excessive. Everything in the quoted definition except for the words "showing disapproval" applies to both "too smooth" and "not smooth enough" -- the part that shows disapproval is the "too". – Gary Botnovcan Nov 30 '14 at 18:01
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Really, the word in these cases are perceived from a perspective.

Just to make a case and build my argument.

The definition you provided would be more like a con artist. The example you gave below is more like a negotiator.

Given that both a con artist and negotiator do essentially the same thing, persuede people, the context and stigma related to the words themselves essentially create a 'good' and 'evil' connotation.

For the word smooth specifically in your examples, it is purely based on context and perspective. It carries a 'bad' undertone, much the same as the word 'sly'. However, it is not inherently 'evil'.

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