However, now that it's done, I don't doubt his earnest or abilities to drive twitter forward. In any case it will be very interesting to watch.
On the other hand, how would he cash out his gamble? You cannot announce that you want to buy 100% of the company stocks, and then start selling off the 9% that you already have, that would be a dead giveaway that the offer is not serious.
Maybe no one will want to hire him as CEO, if that's what you're referring to. But he can just buy another company if he wants to be CEO of it.
Elon Musk? A credible CEO?
And here I was thinking shitposting wasn't allowed on HN.
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.