Say what you want about Matt Cutts. Matt Cutts was assigned the role to be the face of google whether intentional or unintentionally. Think about what kind of position that is. He is the face in one of the most recognized corporations in the world. In my opinion google could not have picked anyone better. As much as I sometimes question google and get fustrated, you simply can not say Matt Cutts is bad at what he does. He is a warm, likeable guy and he does interact with webmasters a whole lot more than you would think is possible. He is on twitter daily answering questions from webmasters. Sure he does not answer everybody but that is utterly impossible.
Matt Cutts is great at what he does. Say what you will about him, if I owned a company I would be very lucky to have someone like him to be the face of it. It is pretty much a thankless job. He is on twitter, he has a personal blog in which he actually replies to users comments. He used to be on forums helping out webmasters etc. Matt Cutts is not to blame for webmasters websites faltering. So long as the good websites outweigh the bad ones, he is doing his job and from an unbiased standpoint, I would say he is doing his job very well.
Do I care about his 30 day challenges? Heck no. Do I care about what video games he is playing? No I dont but he does often talk about what is going on at google and the webmaster videos are a great idea.