He got rid of his PR team at some point, his trans daughter disowned him, and Grimes left him and started going out with Chelsea Manning. I think he got broken. Add wanting to be cool on top of that and you've got a recipe for a billionaire "pick me"
Wasn't there also the thing where he offered a horse to a masseuse if they'd give him a happy ending? A couple days before the story broke he made some statements supporting Republicans then said "watch the left come up with a story to take me down now that I'm a Republican," or something like that. All his political shit has been downhill and ever more unhinged since.
He was always saying side-eye worthy shit, but in a generic rich guy way. His political stuff, before the horse thing, was always progressive-ish. Whether that was what he ready thought, or as the biggest shareholder of an electric car company he knew which side his bread was buttered on, I'm sure I don't know. But it seems like trying to preempt the horse story was the turning point for his public persona.
I originally thought that, but when I read the interview with his daughter- nope. He's always been a queerphobe bigot. Long before she transitioned, when Elon thought she was a gay boy, he constantly berated her for not being masculine enough and just for being queer in general.