I like Obama, in that buddy I'd have a beer with kinda way. As a President, not so much. As with pretty much all politicians, he's "owned" by too many special interests. He's also fallen for the scare tactics of departments like the NSA and Homeland Security.
I believe Dubya's problem was similar. He put too much stock in what Cheney was telling him, instead of thinking for himself. IMO, Cheney is one of the most evil people to ever walk this earth. He was just better at hiding in the shadows.