Why can’t Obama win? Steele says it’s because he’s a bound man who can’t serve the aspirations of one race without betraying those of another. “The black American identity,” says Steele, “is still for the most part grounded in challenging. You never give white people the benefit of the doubt; that’s our power.” And that puts Obama in a tenuous position. If he gives white people the benefit of the doubt, he’ll lose black support; if he challenges white people in a nod to the black community, he’ll lose white support.