People like Trump not just because he's rich but because he's a rich asshole. His obnoxiousness is a feature, not a bug, and can be parsed as any number of things: "Making America tough," "Sticking it to liberal snowflakes," "Shaking up the establishment elites," "Standing up to radical Islam," "Fighting for the common man," whatever. I think underneath all of that there is some beta-dog shit going on whereby pure inarticulate aggression is perceived as strength.
To Trump's fans, it doesn't matter that Obama actually killed thousands of ISIS and terrorist types. Because his demeanor was calm and at times conciliatory, he came across as appeaser/egghead/milquetoast at best (traitor/closet muslim at worst). When Trump said "we're gonna bomb the shit out of ISIS," his base cheered, ignoring the fact that Obama was actually doing precisely that. Hell, they were probably mainly tickled just by his saying "shit."
Sorry to Godwin yet again, but people didn't go for A.H. because he was a nice guy. They went for him because he was a pitbull. He was their pitbull. (Or so they thought.)