Imo the greatest cause of the rift between how supporters and detractors view Trump is caused by his image of being one, if not the, last great hustlers in America

Hustler as in guy who makes money off random shit, however he can, through sheer gumption and street smarts

As a preamble, there are 2 main "life tracks" in the US:

1. Being groomed and prepped for a narrow set of roles within a larger organization from a young age

2. A chaotic, deprived life where one "makes do," does random jobs and gets by any way one can, with no "specialization"

Group 1 is the meritocrats and credentialists, those who value process, deep but narrow knowledge and certifications above all

Group 2 is the hustlers, those who just care about the end result, money and standing, but largely not how you got there, The Hustle

Trump's image places him in the second camp, since it's entirely nebulous (in the public consciousness) how he got so rich/famous. People know he's a real estate and casino guy, but what's his official job (before president)? He just appears to be doing everything and anything

This rubs group 1 the wrong way, as they're used to processes and credentials. A guy who does just whatever and succeeds is offensive to them, especially now that so many of them are downwardly mobile and failing hard despite doing what they were told their entire lives was right

Not so for people who grew up in chaotic circumstances, who were thrust into life with no plan and in any case no money to follow a plan. For them, the image of Trump is an idol. He's the successful hustler, someone who hustled not just to stay alive, but to thrive and get rich

The inverse is also true. For the hustlers, someone like Obama (and most politicians) is too slick, too "in the machine," too on the single-minded career track to be palatable

This also affects left vs right views on small businesses vs corporations, ie hustlers vs The Machine

And yes I know Trump was born rich and went to Wharton etc, I'm strictly talking about the cultivated image here, how the public and various demographics perceive them