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I think Trump is a person who is often misinterpreted if you are not from or not familiar with how people from the Northeastern region speak and I can see how that could pose an issue. He's definitely a New Yorker and more generally a New Englander, and not everyone in the United States is familiar with how they communicate / convey their thoughts to others in that region.

He says stuff, yes, but I can see how some groups of people (or people from certain regions of the United States) don't get it when he's joking or intentionally exaggerating for emphasis or to make a point. If Trump is guilty of anything, its assuming that all the people in the United States, regardless of which part they are from or have lived in, understand the cultural, linguistic and personality (with respect to communication) differences from New England to other parts of the country.

Applying Occam's razor, I just think he's opportunistic and intellectually challenged.

Everybody is entitled to their opinion. :)