Musk is openly antagonistic to any kind of regulation and regulatory bodies. This is all a game to him. Any fines he faces are the price of having fun, to him. It's why whether Twitter succeeds or fails is a moot point. He doesn't actually care about Twitter. It's a toy. It's an RC plane he's flying around, right now, and it's just a matter of time before he intentionally aims it into the ground to see how big of an…
He has not done this with his other large businesses. He has in fact done the opposite, raising them from nothing to hugely successful companies that are also great for humanity. I'm no fanboy - I just call them like I see them. You'll probably mention a few side-projects of his that haven't done much - but he hasn't flown them into the ground either. They're just interesting experiments.
But if you want history of using his money for extreme trolling, just look at the whole Hyperloop thing, where he admitted it was a troll.
He's had a lot of disdain for Twitter in the past. He's laughed at people he's kicked out already. The Twitter story is one giant troll. If, somehow, it manages to get any kind of success, he wins. If it fails, he writes it off and moves on to the next sociopathic experience.