The November 17 issue of the New Yorker has several good articles on Obama and the 2008 Presidential Election. You can read most of them online. Here's the Table of Contents.
I particularly recommend David Grann's "The Fall: John McCain’s choices" and Ryan Lizza's "Battle Plans: How Obama won."
Best of all, however, is a long article by the Editor of The New Yorker, David Remnick, entitled, "The Joshua Generation: Race and the campaign of Barack Obama."
Much has been made of Obama being African-American, but we sometimes forget that his life experience has been that of a person with a white mother and a black father. Obama himself spends most of his first book, Dreams from My Father, talking about this fact and how he struggled in his attempts to navigate the contours and difficulties of being bi-racial. Perhaps coming from a bi-racial family myself, and hearing stories from my father and aunt, I was particularly struck by this aspect of Obama's book.
Remnick covers a lot of ground in his article, but his look at Obama's bi-racial background and how it's played out in his career and in the 2008 election was, for me, the most interesting part.
The historian David Levering Lewis, who has written biographies of King and Du Bois, told me that after reading Obama’s books he had the sense of a young man almost alone in the world, trying to find a place. “The orphanage of his life compels him to scope out possibilities and escape hatches,” he said. “This very smart mother was somewhat absent, and certainly the father was, and the grandfather marched with Patton, but he was not a rock. Obama is in the world almost solo and he learns to negotiate.”
- - - -
As [Harvard professor Randall] Kennedy followed Obama’s career, he was struck by the uniqueness of his background and how it may have affected both his temperament and his public appeal. “He’s operating outside the precincts of black America,” Kennedy said. “He is growing up in Hawaii, for God’s sake. And then, when he comes to the mainland and tries to find his way, he has to work at it. He does have to go find it. He is not socialized like other people. I can’t help thinking that he might have thought it a burden at the time, but maybe some of the things he missed out on were a benefit to miss out on. For one thing, he didn’t absorb the learned responses, the learned mantras and slogans, the learned resentments of that time that one got in college.”
- - - -
“I don’t think Barack’s candidacy was like any other candidacy,” Axelrod said. “He was the first African-American to come along as a legitimate contender whose candidacy was viewed in the broadest terms.” In his Senate race, Obama had campaigned hard and successfully in southern-Illinois towns nearer to Little Rock than to Chicago, and in white areas of northwest Chicago where Harold Washington had been booed in 1983, when he first ran for mayor. “Barack would come back from these white towns and say, ‘They’re just like my grandparents from Kansas,’ ” Axelrod said. “That’s one of his gifts: there is no room he walks into where he doesn’t feel comfortable and make the people feel that way. It’s both his personality and his background—one contributes to the other. There’s no doubt that being biracial contributes to a sense that he doesn’t compartmentalize people by race or ethnicity or background.”
Even black leaders who were initially wary of him came to recognize his advantages. “His background helped,” Al Sharpton said. “He had a primary understanding of peoples that we may not have had. He could meet with me and then with a representative from Kansas and understand the nuances as well as the content of both conversations.”
It's an excellent article - give it a read.