I mean I was aware of him before 1990 and really could not understand how he was famous or successful. My brother is older than me and Trump came up on the news one day and he said "he's either a criminal or his bankers are idiots". We grew up quite a ways from NYC if you're wondering.
The older you are the more insane this timeline seems. I knew he'd get elected. Racism and sexism put him over the top. Still felt like I was going crazy watching it.
Spoilers for future seasons: they try pretty hard to replicate the ratings bonanza of Chancellor Hitler storyline, but it veers way off into weird nonsense, and instead of any sort of satisfying conclusion eventually everyone just gets tired of him and he spends his last years muttering to himself at increasingly sadder and sadder rallies for his remaining geriatric fans.