Think it depends whether you think it was through skill or luck. Obviously there's always a bit of both, but here it seems that there was a fair bit of coin tossing involved. But then again, you generally (note generally) don't make big money without taking big risks.
Politics aside, it's undeniably impressive what he's achieved, but personally I wouldn't be happy with top dogs of a company I owned having so many other things to distract them. I think since buying Twitter, he's just taken on too much.