I think he's doing fine. Once everyone knows about a stock it no longer outs out as much as it did when it was unknown or a possible bad deal. You make big money in stocks by buying them before they become popular or make a big jump. Not sure how buying Skype was a bad idea either.
I wouldn't be bothered about comments from an financial gambler by the way. It is more important for a company like MS, to know that it is doing the right things, moving in the right direction, continuously innovate and keep its customers satisfied. These factors ensure success and sustainability of a company, not a bald headed buffoon from a hedge fund (many of his creed actually created this financial mess the world is in, and funnily enough even after getting their dirty hands on trillions of dollars of tax payers money they continue to propagate that they are right).
It's common practice in large corporations for the CEO to pad the board of directors with friends and allys. It makes them kind of "firing proof". So, if you were looking for them to say something bad about Ballmer, I wouldn't hold your breath.