I guess I'll go with two...
1. Notch. My god that man has talent. I've watched him build games from scratch on streams. It was inspiring. His space game (0xC, something along those lines) was immediately compelling, even though he struggled to decide on a structure for it. But now he just wants to shit all over Twitter, then roll around in it. He might've started out doing it just to screw with people, like he seems to imply, but if it was an act, he's long-since become the milkshake duck he was "pretending" to be.
2. Boogie. Francis mostly stopped being funny long ago, but I followed Boogie for his blogs, and believed him to be a good person. Even he was forward about his vlog persona being a bit crafted, but that makes plenty of sense. It's a reality of being a successful YouTuber. But man, that faux-Centrism bullshit started creeping in more and more, where "somewhere in the middle is a wonderful place to be," even though "the middle" is actually just a way to subtly enable the worst aspects. Then there was that Vidcon clash where it SOUNDED like he got blindsided, and there's a lot of different accounts, and the woman dealing with targeted harassment as it was. I thought maybe Boogie was still ok, but the follow-ups didn't exactly help his case.
Then he posts a video blatantly titled "Should I take the Red Pill?" That bullshit terminology is meant to appeal to a very specific audience. And in the video, he starts into his "both sides" bullshit, he says, "I swallowed that pill years ago, digested it, pooed it out, and learned some things from it." And he meant about life, not about the mysogynists that champion that term. I dropped my subscriptions to him. I think I checked back once later on just to be sure, but the video was still up, there was no apology. I know Boogie was concerned about holding onto his audience after YouTube revenue tanked, but even if he was faking it, which I honestly doubt he was, he still threw his hat in with an awful crowd. I hope his weight loss surgery goes well, and I hope he seriously rethinks his faux-"centrist" bullshit while he's recovering.
Good one. The sad irony is that he's now an actual case of edgy humour being used for irony purposes (primarily in his general aesthetic), vs all the milkshake ducks out there. So it's easy to lump him into the wrong crowd before realising he is basically against everything that crowd stands for.
Him moving away from the faux-dictator slant was a good idea, even though it did work for him pretty well.
...when/why did you ever like him?
For someone growing up in the 80s, not familiar with the housing lawsuits or his views in general, Trump was kind of a cartoon character, beyond even a pop-culture icon. Like Hulk Hogan, or Mr. T. He had a very recognizable look and mannerisms, was vaguely associated with a cartoonish concept of what "wealthy" was, and in general they did a good job scrubbing his shitty image. Even when they were lampooning him, it was in a goofier "oh he thinks about solid gold toilets" kind of thing. Bloom County had an extended plot about Trump having a brain transplant into Bill the Cat's body after an accident. It led to stuff like this:
A chunk of people grew up with "Trump the Rich Cartoon Character", not "Trump the Racist Pussy-Grabbing Traitor".