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The Obama Reader
Barack Obama at Harvard Law

Obama at Harvard Law

Joe Wrinn/AP

No wonder Obama won—the guy’s been on message since he was 28.

January 15, 2009

Over Thanksgiving weekend I went to the Lane Tech basketball tournament and watched with a couple of college coaches.

As the games went on, I listened in awe as the coaches surveyed the parade of skinny Derrick Rose wannabes and honed in on the talent they thought might be worth recruiting. They agreed that a lanky junior who came off the bench for one of the better teams had the most potential. “I know he can’t shoot—but you can work with him on that,” said one of the coaches. “He’s over six feet and growing and he ain’t afraid. It’s all upside with him.”

I’d like to think that when it comes to politics I have the same nose for talent, the same almost preternatural ability to project which one of the dozens of wannabe Richard Daleys or Harold Washingtons will rise to the top of Chicago’s political scrap heap.

But alas, I have to admit that when it came to Barack Obama—the most gifted politician of my lifetime—I blew it.

I first laid eyes on him on September 22, 1989. It was at a conference organized by the magazine Illinois Issues to discuss the state of community organizing in the post-Harold Washington era.

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The Rising Star The Rising Star | When the Next Derrick Rose Is Right Under Your Nose
No wonder Obama won—the guy’s been on message since he was 28.
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That April Daley had been elected mayor in the first municipal election since Washington’s sudden death in 1987. It was still too early to foresee just how much power Daley would accumulate, so the conference focused on what developing communities could do to consolidate the gains they’d made under Washington. (Little did we know that the mayor would effectively crush community organizing in Chicago . . . but that’s another story.)

There were about 20 of us sitting around a table in a conference room in downtown Chicago. Most of us had written articles for Illinois Issues that would be collected, along with a transcript of our discussion, for the book After Alinsky: Community Organizing in Illinois.

Obama, sitting to my left, wore a white shirt and a thick dark tie; he was 28 but his baby face made him look younger. I didn’t know much about him at the time, but now, having read Dreams From My Father, I know he’d just finished three years as community organizer in Roseland, a poor African-American neighborhood on the far south side. And that, like so many young activists before and since, he was giving it up for law school—at Harvard, in his case.

When it was his turn to speak that day, he talked about the trials and tribulations of trying to organize low-income black communities. I wasn’t impressed. To be honest, I’ve always been attracted to the Sammy Glicks of Chicago politics—the street fighters who scratch and claw their way to the top. But then as now, Obama was a different kind of cat. Smooth and calm, he shielded his ambition behind a veneer of cool. Not that he didn’t enjoy being listened to—I remember thinking that he sounded like a windy sociology professor with nothing particularly insightful to say. If you had told me he was going to become president, I would have said sure, right after I win the Nobel Prize for literature.

In fact, I was late to see his potential even after he launched his political career. Other Reader writers—Hank De Zutter, Edward McClelland (then writing as Ted Kleine), and Grant Pick—were much more enthusiastic about young Obama. As I watched him rise from obscure state senator to failed congressional candidate to surprise U.S. Senator to presidential candidate, I wondered: Is this wimp ever going to take a tough stand? I like my pols to stick it to the man—my favorite alderman is still Leon Despres, and he retired in 1975. But Obama rarely raised a peep of protest even in the face of the scandals, boondoggles, controversial school closings, and wholesale removals of black communities that have marked the Daley years.

It’s true, he came out against the war in Iraq in 2002. But at the time he was getting ready to run in the Democratic primary for U.S. Senate in one of the most liberal states in the country, so he really didn’t have much of a choice. When he won the Senate seat in 2004, I pegged him as lucky. Blair Hull and Jack Ryan, the two front-runners, were brought down by embarrassing revelations pulled from their divorce files. After Ryan abandoned his campaign, state Republican leaders, clueless as ever, replaced him with Alan Keyes. I could have defeated Alan Keyes. Without campaigning.

When Obama announced he was launching a presidential campaign in 2007 from the capitol steps in Springfield, I still thought the guy was too chicken to stand up to Mayor Daley—so I figured he’d never get tough with the Clintons. And I predicted that even if he somehow stumbled into the nomination, the national Republicans would annihilate him.

As you can see, at every stage I underestimated Obama. But I didn’t realize by exactly how much I’d underestimated him until I drove to Iowa last January for the caucuses.

On January 2, the day before the caucuses, I caught an Obama rally in a hotel banquet room in Coralville, a town just outside of Iowa City, home to the University of Iowa. I couldn’t believe what I saw—it defied everything I’d come to believe about how race intersects politics in this country. It wasn’t just that the room was packed; it was that it was packed with white people, and their excitement bordered on euphoria. They didn’t care that Obama was black—or maybe they liked him precisely for that reason. Either way, his race was hardly an impediment.

When Obama took the stage, they stomped their feet, cheered, and clicked their cameras to capture the moment for posterity. But I barely paid attention to what he said because I was fascinated by how he said it. He’d honed his style and delivery. He was folksy, having fun—not a trace of the sociology professor. Obama had clearly been studying stand-up comics; instead of standing behind the podium, he glided across the stage, microphone in hand. He understood just when to pause to allow the absurdity of a Republican position—on health care, for instance—to set in with his audience. He’d learned not to talk over their reaction.

Scarlett Johansson, who’d flown in to endorse him, showed up during the speech. A little later she gave a brief pep talk to some of the volunteers in a smaller room in the hotel. “This is just so important,” she stammered, obviously as starstruck as everyone else. Afterward she went to the campaign headquarters in Iowa City to make phone calls. As word of her presence spread, the room filled with volunteers—suddenly everyone wanted to make calls, or to watch Johansson make them: “Hi, I’m Scarlett Johansson, and I want to know if we can count on you to caucus for Barack . . . ”

It was obvious that while I’d been so skeptical the rest of the country—or at least Iowa—had been swooning. Obama’s campaign had become a crusade. He was using new media to reach his audience—the kids in the Iowa office were getting daily video updates on their Facebook sites. (Within a few weeks they were all posting and reposting “Yes, We Can” by Will.i.am.)

That night the Iowa City volunteers—some of whom had been working their precincts since the previous summer—called voters until midnight. The rules in Iowa are pretty liberal: if you go to college there you can vote there, regardless of where your parents live. The university was on winter break when the caucuses were held, but it didn’t even matter: students returned to Iowa City in droves from other parts of the state, Wisconsin, and Illinois. No other candidate had an organization or following in the same league. In retrospect, Hillary Clinton didn’t have a chance.

On January 3, I watched a caucus at the University of Iowa’s student union, where one desperate Clinton supporter tried to win over undecided voters by linking Obama to Tony Rezko. He might as well have been speaking another language—I may well have been the only other person in the room who’d even heard of Rezko. “He’s this really sleazy guy who helped Obama buy a house on the south side of Chicago,” the guy explained. “You’ll hear about him. Trust me, the Republicans will make a really big deal about him if Obama’s the nominee . . . ”

We were only a couple hours from the Illinois border, but Chicago politics had never seemed so alien, so irrelevant, so far away. I mean, who cares about south-side land deals when you’re trying to change the world?

Obama won 80 percent of the vote in the student union on his way to taking Iowa. And then, well . . . you know the rest of the story.

I returned to Iowa City for the general election in November. By this time Obama’s organization had been going round the clock for months, registering new voters and badgering folks into voting early. For the final push, volunteers went door-to-door reminding people to get to their polling places, each of which was monitored by at least one lawyer and two poll watchers from the Obama campaign.

At seven—two hours before the polls closed—field organizers dispatched volunteers to make one last sweep of the dormitories. I was following Wes, a sophomore from Evanston, as he knocked on every door on the girls’ floor, until an RA asked us to leave with a promise to call the police if we didn’t. “Technically,” he said, “this is solicitation.”

With less than an hour before the polls closed, Wes and his roommate James were sent back out to rouse any late-voting stragglers. They stumbled about in the dark in some god-forsaken precinct where the few people they found at home were annoyed—of course they’d all been to the polls. Wes got a call on his cell from his father telling him Pennsylvania had gone to Obama. Not long after that we saw a guy standing on his porch smoking a cigarette. “Forget it, dude,” he said. “Everybody’s voted. It’s over.”

They held their celebration party at the local Sheraton. I think every lefty in the state was there, including one codger old enough to remember campaigning for Henry Wallace in ’48. When the big screen showed Obama stepping onto the stage in Grant Park, the room erupted. People were hugging one another, openly weeping—even me.

A few weeks after the election I found the old book After Alinsky, the one that included the transcript of my one moment with Obama nearly 20 years ago. Reading it again gave me a jolt. It was all there: the strategy he would follow, like a recipe, to the top. Suddenly it was obvious that even then the guy had a plan. If community organizers were to be successful, he said, they had to look beyond Chicago, “get bigger horizons, start to understand how they connect up with other people.” They had to think beyond the small victories: “You have to link up winning that stop sign . . . with the larger trends, larger movements in the city or the country.” They needed to reach out to the marginalized, using more than the conventional media: “We have to figure out some medium to reach black youth.” They had to learn from Republicans how to project a consistently positive image: “I think the culture of the right wing now thinks about it, Ronald Reagan thinks about it. We don’t understand it, we don’t think about rethinking ourselves, projecting ourselves.” Above all else, they had to get into politics. “Politics is a major arena of power,” Obama said that day. “That’s where your major dialogue, discussion, is taking place. To marginalize yourself from that process is a damaging thing.” He was even mildly critical of Harold Washington and Jesse Jackson, emphasizing that black leaders have to reach beyond the black base: “Instead of just bringing blacks into the board room, he [Washington] should have been helping to foster in the black community the sense that they need to organize even more and build even more and broaden their base.”

If I’d been listening a little more carefully back then, if I’d not been so focused on what I wanted to say or so irritated by what a few of the other speakers had said, I might have realized that the skinny kid in the fat tie was on to something—that I had in fact stumbled on the next Derrick Rose of Chicago politics.

Oh well. There will be others, and I’ll spot the next one—you’ll see. In the meantime, I’ve got to give Obama his props. I still think he was lucky. But he had the sense to put together a realistic plan and the determination and tenacity to carry it out. Obviously his reluctance to take on Daley was calculated. It was pointless to try to lead the people where they are too afraid to go. I don’t think he’d ever admit it in a million years, but he clearly saw us for the hopeless losers that we are and began to plot his way out almost from the moment he parachuted into town.

Of course I wish him well. I hope those kids in Iowa are right and he does indeed change the world. And maybe he can—if he can get out of this town without being caked in sludge then hey, anything’s possible.   R


Plus An Inauguration Guide, Inauguration Metaguide, and more coverage from our sister paper, the Washington City Paper

For additional Obama stories from the Reader archives visit chicagoreader.com/obama/


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