I think you're right. He's in a different class than the rank and file, and since he didn't really come up through those ranks, he has no idea how it is down here. At the very least, Trump is a businessman, and at least has an idea that things can cost you real money if you're not careful.
The one example I can cite is his desire to re-instate and expand the ACA. For everyone save those who made nothing and didn't have insurance, that program was a disaster. I can't give you one example of a working person that helped.
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