Those who mistake Obama’s stint as a community organizer as evidence of a pie-in-the-sky, naïve idealism have got it exactly backwards. In Chicago, he learned a realpolitik approach to civics—an organizing style predicated on realism, power, and confrontation. It is this clear-eyed political approach that contrasts so strongly with his gauzy, lets-all-get-along campaign rhetoric.

But it also may work in opposition. So far, Obama been a cipher, a post-ideological vessel into which liberals off all stripes can pour their fondest post-racial hopes. But what does he really believe in? Is there any core idea there, besides ambition? And if there is a core, is it old-school liberal, wide-eyed realist, post-partisan centrist, or something in between?

Put more cynically, is he an authentic urban organizer at heart, someone who sees politics merely as the quickest path to revolutionary change? Or has he been co-opted by power—just another ambitious pol using whatever he can weave from his biography to close the sale with voters and donors? …

If he maintained his ideals through Harvard—if he believed so strongly in his task of civil rights and community organizing that he couldn’t even be delayed by two years in the high courts—then maybe he retained them through the US Senate. Maybe he is, as they say in the business (always with a touch of irony), the real thing.

And then there’s another explanation—one more decidedly nefarious: He was desperate to start a political career. He didn’t want to be detoured by a high-end legal practice, and the chit of a SCOTUS clerkship wasn’t nearly as important as establishing urban credibility on the South Side of Chicago for his upcoming election (which would almost certainly involve a strong challenge from a civil rights-era black politician and—lo!—it did!). He was too impatient and ambitious for the Supreme Court. He had set his sights much higher and, back then— possibly like today—he was looking for the shortest root to power. He couldn’t be bothered with the Supreme Court….

I’m a little surprised no one in the media or blogosphere has asked this question. It is one thing to eschew a Big Law job. It’s another to eschew a golden ticket that can open doors in the law, business, academia, and politics. Yet Obama appears to have done so. I don’t know why. But the answer may say a lot about him.

Upon reading this article all that came to mind was “How Clinton of him”. Everything is an oversight until the political microscope comes out looking for some dirt before a significant election. What does this say about Obama’s character?

Meanwhile, the Cambridge parking director has nothing but kind words for the former delinquent:

“I think it’s fabulous he finally paid them,” Susan Clippinger told the Boston Globe of the presidential candidate’s reckoning with the parking office of $375 in fines and fees. “I think others who owe us money should pay us, too.”