In a way, Trump is a paradox. Here’s a billionaire, a guy from the North East, ivy league educated, living in cities
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Living in a city and being conservative is not a paradox. There are countries where people in cities want small government and people in low population areas want big government.
https://twitter.com/kennethfield/status/970827334038237184/photo/1
Generally speaking, urban areas vote more liberal, even in more conservative states such as Texas where all the major cities are Democrat.