Virginia Postrel has some insightful things to say about Presidential glamour.  About Obama she says:

Postrel: Yes, President Obama is a very glamorous figure. Glamour is a particular form of illusion. It’s an illusion that tells a truth about the audience’s desires, and it requires mystery and distance. During the campaign people projected onto Barack Obama whatever they wanted in a president or even in a country. Lying is usually a bad thing, but they would project onto him that he was lying about his positions because he secretly agreed with them: “Anyone that smart has got to be a free trader at heart. He’s just saying this to pander to those idiots. He can’t really mean it.”

You’ve seen, as he’s taken office and tried to govern, this back and forth where he is consciously or unconsciously trying to maintain his glamour—which requires a kind of distance from the political process so that people can continue to see him as representing them, regardless of their contradictory views—while actually trying to be president, which means you have to decide what to do about Guantanamo. You have to decide what health care bill you’re going to back. You have to decide all these things, and you’re going to make somebody disillusioned. This morning I saw that the former editor of Harper’s is about to write a book, The Mendacity of Hope, attacking Obama from the left. That’s the power and the downside of glamour.

Also here’s what she has to say about Reagan’s glamour:

Postrel: There were two glamorous presidents in my lifetime besides Obama. The first was JFK, and he dealt with this problem by getting killed. That was something I didn’t want to mention in an article about Obama. There were lots of problems in the Kennedy administration and lots of secrets that were being hidden that came out later. But because he was assassinated, the glamour stayed.

The other glamorous president of my lifetime, I would argue, was Ronald Reagan. And he managed to govern because he actually did stand for some specific ideas that brought a broad consensus of supporters together. He was still a figure of distance and mystery, to the extent that his authorized biographer, who followed him around for years, was unable to get at what the man was really like and wrote a semi-fictionalized biography with fake characters. But there was a core of identifiable beliefs that enabled him to govern and to maintain this sort of glamour, particularly to the Reagan coalition. Libertarians would say, “well, he’s really more libertarian,” and social conservatives would say, “well, he’s really more socially conservative.” But he did have specific beliefs that held those people together. They didn’t hold together so well after him.