In this weeks' New York Times, Maureen Dowd does a nice job of explaining how Obama, with the closer-to-ordinary background, has worked to build a more sophisticated image that now is working against him, whereas Clinton, the more privileged, is somehow pulling off that she can better relate to the everyman.

http://www.nytimes.com/2008/05/04/opinion/...

And David Brooks, no fan of either one of them, points out how Sunday's talk show appearances displayed how Hillary is coming off as the more aggressive and, yes, masculine.

http://www.nytimes.com/2008/05/06/opinion/...

This is how George Bush won. By being the one you'd want to have a beer with, and by being the one who you could believe might shoot first and ask questions later. These are apparently the perceptions that win elections, and Hillary seems to be betting--with some success--that America hasn't learned its lesson.