Option A: Son is right, and the market is wrong. WeWork is a ~$50b company, and after a bit of hardball SoftBank will own 70% of it for a very affordable $15b (or whatever it is). And once the market catches on, WeWork's valuation will quintuple overnight, netting the Vision Fund a nice profit and Son the right to be very, very smug.
Option B: The market is right, and Son is wrong. WeWork is a ~$10b company, which through a fit of almost comic mismanagement Son has managed to pay ~$15b for (and still owns only a bare majority). With a lot of work (and thanks to getting rid of Neumann), it might one day be worth enough SoftBank/the Vision fund is (barely) not below water, but even that's iffy.
I'm no expert, and while on paper option B does look pretty compelling, let's say maybe option A is right after all. In which case...
...given that Son is just a uniquely talented visionary, and saw potential that nobody else (and especially not other potential investors) saw, uh...why in the hell did he keep investing at higher and higher valuations? Like, if the market is just dumb and can't see that WeWork is worth $50b, not $10b, then....why invest at a $50b valuation? Unless it was just a glorified pump-and-dump all along (ie, Son never thought it was worth $50b, but he thought other people could be fooled into thinking it), in which case, why invest now? Does he think he's going to get a second bite at the apple? It's really hard to imagine us all being here in 18-36 months going "wow, WeWork sure has turned things around, I think their IPO will price at $60b!" Right? Isn't the WeWork hype irrevocably gone?
This whole thing is so odd. Is it really as simple as "we're just piling billions of dollars up and setting them on fire because we love expensive bonfires"? Is that it?