Back then he had a PR firm working for him, getting him cameos and good press. But in 2020 he fired them deciding that his own "radically awesome" personality doesn't need any filtering.
Personally I don't think Elon is the worst billionaire, he's just the one dumb enough to not have any PR (since 2020). They're all pretty reprehensible creatures.
The watershed moment for me was when he pretended to be a top tier gamer on Path of Exile. Anyone in the know saw right through it, and honestly makes me wonder if we just spotted this behavior because it's "our turf", but actually he and people like him just operate this way in absolutely everything they do
Peter Thiel who thinks the Pope or Greta Thunberg might be the antichrist, and that freedom is incompatible with democracy
I think you did not understand his argument. He said it is a great danger that people might unite behind an antichrist like figure.
Any number of past mega-rich were probably equally nuts and out of touch and reprehensible but they just didn't let people find out. Then Twitter enabled an unfiltered mass-media broadcast of anyone's personal insanity, and certain public figures got addicted and exposed.
There will always be enough people willing to suck up to money that they'll have all the yes-men they need to rationalize it as "it's EVERYONE ELSE who's wrong!"