The New York Times article I've linked quotes someone who raises questions about a one-size-fits-all no contribution policy for employees. Olbermann is not a straight news reporter. He's transparently partisan. Does it really matter if he puts his money where his mouth is? Also, what is MSNBC going to do about Joe Scarborough, who apparently gave to Republican candidates in 2006?
If you care: I think Olbermann made a mistake. Even when you're partisan and your opinions are clear I think it's best not to make political contributions in the areas you cover. Having a financial stake in the game just seems different somehow. There's also the potential for making it appear you might have received a favor from a candidate for a contribution. I made a political contribution once — to Hillary Clinton's campaign for U.S. Senate in New York. I was pretty sure the Times had little influence in New York. Perhaps I should have kept my record clean. Oh, OK, it wouldn't have been totally clean. I think I gave Jim Lendall $10 once for one of his early quixotic political races, maybe for city board against Sandy Keith.
But before you righties get all in a lather: If an opinionated commentator should be removed from his cable TV job for making political donations, whatcha gonna do about Fox's Mike Huckabee? The money may come from his PAC, but it's still money he's doling out.