The thing is, I was thinking the same thing over 30 years ago. Further than that, when I was in high school, he was fairly much in the news or other media all the time; when I was in college someone ran an op-ed in the student paper extolling Trump’s virtues and going on about what a loser Garry Trudeau is and, (then) hypothetically, wouldn’t we all be so much better off if Trump were president and not Trudeau? (I’m not so certain that author would’ve been happy with their preference about 30 years later.)
I hadn’t & wouldn’t have given Trump a 2nd thought 
until 2005 or so (maybe a bit earlier), when Letterman was showing a clip from The Apprentice. I saw the hair (which Letterman probably pointed out) & wondered “my gracious, what the hell’s happened to Donald Trump?” And “where’d they pull him out of?” as he seemed such a has-been by then. OTOH maybe he’d remained popular all along and, not caring anyway, I simply didn’t realize.
Fast-forward to the Obama presidency, 2010 or so, and there was seemingly no microphone, megaphone etc. that someone did not want to give to this bigoted, buffoonish game show host/property owner that plays a billionaire on TV.
(I recall a pizza commercial somewhere along the way. I’ve never seen Home Alone in its entirety and none of its sequels.)
