I think Donald Trump's heyday was the 80s. I knew him in my childhood and adolescence in the 2000s and early 2010s, but he didn't mean that much to me.I think the general cultural perception of him was just as a rich guy. Occasionally you'll hear a line in a rap song and just chuckle a little, like hah that was a different time. The lines are usually about getting money, or calling oneself the "Black Trump" because you have a lot of money. Idk, tbh I can't think of any off the top of my head except for Mac Miller releasing "Donald Trump" in 2011 and Kreayshawn mentioning Ivana Trump in Gucci Gucci also in 2011, but they're definitely out there.
I think he got the hogs on his side by just repeating the shit they had been saying for years, whether in their Tea Party circles during the Obama years, or on messageboards like 4chan. Or you could go back to the talk radio of the 90s and stuff and hear the same stuff being said. He was just speaking the hogs' language, and so of course they ate it up. Plus, he was able to ride the American assumption that wealth=competency. All those kulaks with their car dealerships look up to a guy like Trump just because they want to be him. When he says he makes the best deals, they say of course he does, if you have that much money you must be doing something right.