Why does it astound you that opportunities go to the opportunists?
I think that what you're seeing here is that gifted people do eventually catch a break and luck into a lofty and well-paying job. And then their employer starts telling them what to work on (because, after all, people don't pay you for being smart - they pay you to do things for them), and they don't have time to work on the cool-but-relatively-useless public-domain stuff. From the outside, it looks like they've suddenly become utterly untalented, ill-suited, and miserable. But from the inside, they're just as smart as they ever were, it's just that their talents have been redirected into invisible things that people will actually pay for.
I used to do cool stuff like teach folks how to write Scheme interpreters in Haskell or port Arc to Javascript or spend half a day re-implementing Tetris on a webpage. Eventually enough people noticed that I got a nice job at Google. I still work on cool stuff, but nobody notices anymore, partly because everybody takes the fact that Google Search just works for granted and because I work with enough other talented people that I can't claim sole credit for anything I do anymore.
If Gwern wants a job at Google, I'll be happy to refer him.