The Education of Barack Obama

When reporters go one on one with Barack Obama, they end up writing things they'll regret in the morning papers. It's a phenomenon called "drinking the Obama juice." One besotted scribe called him "tall, fresh and elegant." And the august Atlantic Monthly mooned about his "charisma, intelligence and ambition, tempered by a self-deprecating wit," titling its article "The Natural."

OK, Obama is tall (6'2"), intelligent (Harvard Law, two bestselling books), and damn, he's ambitious (running for president after two years in Congress). But he's no natural. He's a driven politician who had to lose an election, in humiliating fashion, before he discovered the voice, the style and the agenda that have made him a celebrity senator, and the next Next President.

As a correspondent for the Chicago Reader, I covered Obama's 2000 campaign to unseat Rep. Bobby Rush, the ex-Black Panther and South Side civil rights hero. It's the only election he's ever lost. As even one of Obama's admirers put it, "He was a stiff." You think Al Gore and John Kerry looked wooden, haughty and condescending on the campaign trail? You should have seen this kid Obama. He was the elitist Ivy League Democrat to top them all.

I got my first sight of Obama early that winter, at a church in Bronzeville. It was a Saturday afternoon -- as a greenhorn challenger, Obama wasn't getting the Sunday pulpit invitations -- and maybe a dozen people were scattered in the worn pews. This was half-a-decade before "-mania" was added to Obama's name. Weak December light strained through the stained glass. Obama wore a suit and tie -- he hadn't yet pioneered high-fashioned, open-necked campaign casual -- and, posing uncomfortably before the baptismal, tried to relax the crowd with self-deprecating wit.

"The first thing people ask me is 'How did you get that name, Obama,' although they don't always pronounce it right. Some people say 'Alabama,' some people say 'Yo Mama.' I got my name from Kenya, which is where my father's from, and I got my accent from Kansas, which is where my mother's from."

At the time, Obama was teaching constitutional law at the University of Chicago, and this was the sort of awkward, beginning-of-the-semester joke you hear from a professor trying too hard to prove a sense of humor. If anyone caught that Obama was trying to connect himself to the birthplace of civil rights and the black community's favorite party joke, they didn't laugh, or nod. He went on to give a speech attacking Rush as "reactive." Afterwards, when I polled his listeners, one told me Obama represented a "new generation" of black leadership, which is the wrong way to sell yourself in a primary election dominated by senior citizens. Another was a hip-hop poet. He handed me a business card, featuring a photo of himself wearing clown makeup.

Every account of that campaign points out that Obama was tagged as "not black enough" for the South Side. State Sen. Donne Trotter, the third wheel in the primary, sneered that "Barack is viewed in part to be the white man in blackface in our community." Black nationalists grumbled about an "Obama project," led by the candidate's political godfather, former Clinton White House counsel Abner Mikva. But no one appreciates how hard the man tried to earn his ghetto pass. At a rally for South Side teachers, held in a dim, tiny nightclub called Honeysuckle's, Obama lashed out at the critics who were calling him too bright and too white.

"When Congressman Rush and his allies attack me for going to Harvard and teaching at the University of Chicago, they're sending a signal to black kids that if you're well-educated, somehow you're not 'keeping it real.'"

The air quotes hung over the silent gathering.

Wherever Obama went, he talked like a poli. sci. thesis. Here's how he bragged on himself: "My experience of being able to walk into a public housing development and turn around and walk into a corporate boardroom and communicate effectively in either venue means I'm more likely to build the kinds of coalitions and craft the sort of message that appeals to a broad range of people."

Obama just couldn't -- or wouldn't -- loosen up. The dignified demeanor that had won him a Senate seat in the university community of Hyde Park did not translate to the district's inner-city precincts. His internal rhythm was set to "Pomp and Circumstance." "Arrogant," scoffed a South Side radio host. Even his body language signaled he was slumming. During a debate with Trotter, in the dank basement of a park field house, he sat with his lanky legs crossed, chin cocked at a heroic angle. He wasn't even trying to conceal his impatience with a mere state senate peer, or with this grungy necessity of campaigning. Trotter, who embodied bourgeois black Chicago, from his bow ties to his soul food lunches to the smooth jazz oozing from the speakers of his Jeep, hunched over his microphone, taking digs at his increasing irritated rival. When he finally needled Obama for failing to pass a child support bill, the calm dissolved.

"Senator, that's a distortion!" Obama snapped. His baritone went full fathom five, but he never unbent from his patrician pose.

Obama may have been testy because he did have a reputation as an ineffectual legislator -- for many of the same reasons he was tanking as a campaigner. Some of his colleagues saw him as a self-righteous goo-goo who thought he was too cool for the chamber, and disdained the hard work of digging up votes.

"Barack is a very intelligent man," said Rich Miller, publisher of Capitol Fax, a statehouse dope sheet. "He hasn't had a lot of success here, and it could be because he places himself above everybody. He likes people to know he went to Harvard."

Obama had been a golden boy for so long: embraced by the Ivy League, profiled in The New York Times, published by Times Books. At 38, it gnawed at him that others his age were already moving up the political ladder. U.S. Sen. Peter Fitzgerald, whose seat Obama now holds, was only a year older. But for the first time in Obama's life, his ambitions were blocked. The world was pushing back. His impatience showed in a condescension to his surroundings.

When I interviewed