David Weinberger blogs about George Bush denouncing 527 groups. David links to Roji pointing out that this is a serious flip-flop from his original position.
David's point is that on the one hand, the 527 groups represent a way to buy influence. On the other hand, limiting the ability for a 527 group to be formed and express a point of view is limiting free speech.
I think the reason we have this conflict is the nature of media today. It shouldn't cost millions of dollars to get your message out; the system should be transparent enough so we know who is behind those messages; and most importantly, those messages should spark dialog and lies and stupidity should be smacked down as fast as urban legends on snopes. The problem with allowing money to buy "free speech" is that the speech is asymmetrical and not deliberative. ...yet.