My brother in Houston thinks we all drank the Kool-Aid—me, his twin brother in New York City, and our sisters in LA and Vancouver, all of whom kept telling him Obama was not just the better choice but the only choice.

His view was that to pile so many hopes and dreams onto such wispy credentials as Barack Obama possessed was to act in mad defiance of the laws of aspirational physics. A vote for John McCain would, at least, be a vote for who McCain actually was instead of what his idolizers had decided he represented.

Our view was that if you didn’t understand what Obama represented you’d slept through the past half century.

But I couldn’t begrudge my brother his skepticism. I’d seen Obama up close, and he didn’t bowl me over. I’d heard him show up exhausted at a dinner and give a speech that everyone cheered wildly even though it had been really lousy. I’d winced at the precious Annie Leibovitz holiday card bulk-mailed to constituents a couple years ago. When he ran for his party’s nomination for the Senate in 2004, he didn’t get my vote. The fawning over him offended me: it was like nothing I’d seen since 1972, when Dan Walker, who’d issued a report calling the ’68 Democratic Convention a police riot, ran for governor and “reform” Democrats bailed on lieutenant governor Paul Simon (whose sin was accepting backing from party regulars). Not only did Walker wind up in prison after his single term, he was an ineffective governor for those four years and you could cut his administration’s self-regard with a knife.

If 20 straight years of alternating Bush-Clinton administrations hadn’t already been eight years too many, it’s possible I’d never have come around to Obama. But at some point I decided that he was decent enough and smart enough, and such an original, that even Americans who didn’t vote for him would like their country better if he won. That’s what happened with Kennedy in 1960: he beat Nixon by an eyelash, but after he’d been in the White House a few months, millions of Americans who couldn’t bring themselves to vote for Kennedy forgot that they hadn’t.

And there was something else about Obama—he didn’t really give a damn whether I liked him or not. Despite that big grin, he was the least ingratiating Democratic presidential candidate since Kennedy. It was as though he understood that his followers were so determined to see Jesus in him that an air of empathetic self-sufficiency was enough to sustain their fidelity—and it covered him like armor. When he told Hillary Clinton, “You’re likable enough,” I could almost hear him thinking, “But likability is overrated anyway.”

Not since Kennedy has a president-elect so clearly stood for a new generation taking over. In the first season of Mad Men, the election of JFK is an important plot point: it warns the marketers who make their money by pushing America’s buttons that something new is stirring that they need to understand. Season two takes the story through the Cuban missile crisis, and those of us who never miss an episode can’t wait for the cataclysms just ahead: assassination, war, women’s lib, black power. Hey, Don Draper, in your soon-to-be-snickered-at creased white shirt: try selling your cornflakes now!

So far, Mad Men has ignored race—but if the show lasts long enough, race will have to leap out and bite Don Draper in the eye. Jim crow was our national stain as the 50s gave way to the 60s—the gentleman’s agreement that everyone north as well as south colluded in, from political leaders to church leaders to distinguished educators and businessmen to media pundits and Madison Avenue. Best let the south be. If you went down there for the wrong reasons, you could die.

For those old enough to remember jim crow, it’s yesterday. During my senior year in J-school at the University of Missouri, things got particularly ugly in Alabama, and two editors from our student newspaper drove south to take a look and write some stories. Their audacity made me blink. It pointedly reminded the rest of us aspiring journalists that the life we’d chosen could be profoundly serious—it was about going into danger to act as the people’s witness.

One of those student editors was Martin Frost, who went on to become a congressman from Texas, the senior Democrat on the House Rules Committee when Tom DeLay redistricted him out of office in 2004. It was a piece of nastiness I could not forgive DeLay for, and it worked its way into my personal 2008 agenda. As I’m sure all presidential candidates do, Obama toted a lot of baggage he knew nothing about, and some of it was mine. I wanted him to win to vindicate a guy I’d gone to school with.

Forty years after the assassination of Martin Luther King and the riots in Chicago, Washington D.C., and a hundred other cities, America wasn’t suddenly ready for a black president. But progress is an opportunist and the stars were aligned for Obama, who is virtually sui generis—his acculturation being white, African, Hawaiian, and Indonesian, his equilibrium astonishing, and his innermost self unknowable. He’s black almost by choice, and he’s made it the cool choice as well as the necessary one—I don’t think he could have been elected with a white wife.

The night Obama won was surreally mellow in Grant Park. People wandered about stricken dumb by bliss. If you were young you knew you were witnessing history. If you were older you were staggered by how unbelievably generous time had decided to be. Maybe you recalled the infamous “police riot” that had taken place in Grant Park 40 years earlier and alienated everyone it touched. Who there then could have imagined this? Time twists and turns, but when does it ever come back around to a place it once cursed and forgive it?

The election of Barack Obama left me so buoyant it took me a while to find the words. Finally I realized that I hadn’t felt so OK with this country since November 22, 1963. I felt nearly young.

A few weeks later, at a dinner party held by friends who are one degree of separation from Obama’s inner circle, the conversation turned to the mess this country’s in, and our hostess predicted Obama would accomplish things that would make his election look like small beer. I wasn’t so sure. A nation’s troubles come and go, and it’s hard for me to imagine anything Obama might do that would be more transformational than getting himself elected in the first place. The day he’s sworn in, I’ll still be rubbing my eyes.

To that, my brother in Houston would say he thought elections were supposed to be about running the country, not redeeming it. But he’s a man of good will who believes in judging candidates on their merits, and I’m sure if things go well he’ll be open to voting for Obama in 2012. If they don’t, will I be as open to voting against him?v