By now, just about everybody’s got a Barack Obama story. Some are even about the man—over the years he’s worked with, met, or spoken to thousands of Chicagoans. Thousands more have argued about his qualifications or wondered about his symbolic importance over beers or on the airwaves. Others have stories that are really more about themselves—where they were on election night when he was called the winner, what their parents thought of his speech, how any of what he said might help them find a job.

I’ve got a few myself, and my favorite is from early in his 2004 Senate campaign. Obama was still an underdog, if not an afterthought, in the months before the Democratic primary—among his six opponents were the son of a party power broker and a billionaire. I was working for the Chicago Reporter, a monthly that focuses on racial issues, and had no problem getting his staff to set up a sit-down. But when a colleague and I showed up at the appointed time—around 5 PM one weekday—the candidate strode out of his office with an annoyed look. It quickly became clear that no one had told him we were coming. “This is really not a good time, guys,” he said. “This is a time I need to be making phone calls. I need to be fund-raising.”

The young, cool, progressive state senator who needed press was going to blow us off? To call rich people and ask them for money? So it seemed. Obama shook his head, repeated that this was a bad time, looked at his watch. “Come on,” he finally muttered, gesturing for us to follow him back to his office. “But we’ve only got a few minutes.”

All it took was a few basic questions about why he was running and why he thought he could win and Obama was off to wonky wonderland, outlining policy ideas, citing election data, and arguing about political history for the next hour and a half. He took visible pleasure in thinking through the questions. Even if he was quite confident that he had the right answers to most of them, he wanted to get our take, and on the points where we more or less told him we thought he was full of shit, he more or less refused to deny that politics involves careful strategizing. Which I still think was an honest a way of avoiding a stand.

A couple days later my colleague and I ran into him in the Grant Park garage. We were hurrying to our car and a flag football game, and we invited him to join us, thinking his height and athleticism could only lessen our chances of losing again by four touchdowns. “I’d love to, guys,” he said, “but this time I’ve really got to go do some fund-raising.”

The Reader has been collecting more substantial stories than mine about Obama since 1995, when it ran what might be the first in-depth profile of the young politician. On the eve of his inauguration, we thought we’d share with our readers (and those of our D.C. sister publication, Washington City Paper) some of the best, as well as some new reflections and a couple of prescient stories about two key advisers: chief of staff Rahm Emanuel and media consultant David Axelrod. Here’s to four more years of following the “skinny kid from the south side with the funny name.” —Mick Dumke

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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