Shelby Steele examines the challenges that Barack Obama must overcome in his bid to become President of the United States in A Bound Man: Why We Are Excited About Obama and Why He Can't Win. Having to cater to both black voters and white voters in what binds Obama, and his dilemma is that he achieved visibility more as a racial icon than as an individual. In his analysis, Shelby Steele discusses his own mixed race background, and he empathizes with Obama's inner conflicts even as he critiques him. He also identifies the two 'masks' that blacks wear in order to seek success and power in the American mainstream: bargaining and challenging, and he argues that Obama is too constrained by divisive racial politics to find his own true political voice - and proposes a way for him to break those bonds and find his own voice.

Shelby Steele is a research fellow at the Hoover Institution, Stanford University, and the author of The Content of Our Character and White Guilt, and a contributing editor at Harper's; his work has also appeared in numerous other magazines and newspapers.