I think that is wishful thinking, a product of a desire on Sullivan's part to escape history, a classic Romantic, indeed "Transcendentalist" urge.
The truth about Obama is that he is a symbol of the victory of one side. Obama's candidacy is the Iwo Jima, if you will, for the side of the Boomer war that has, after more than three decades, "overcome some day": the hippies, the war protesters, the drop-outs, the integrationists, those hairy, messy, starry-eyed kids who moved to San Francisco with flowers in their hair (well, the ones that got past the drugs).
Read the whole thing. I think my response would be that an integration of the best of the 1960s (and a rejection of the worst) is exactly the post-boomer synthesis I'm talking about. And a former president of the Harvard Law Review, Senator and foreign policy realist does not strike me as a hairy, messy starry-eyed kid. Not that there's anything wrong with hairy, messy starry-eyed kids, of course.