How Obama learned to be a natural

Today he drips with charisma and inspires fawning admiration from all quarters. But Obama began his journey as a smug young man with little political future.

Topics: 2008 Elections, Barack Obama, Chicago,

How Obama learned to be a natural

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 Obama’s “charisma, intelligence and ambition, tempered by a self-deprecating wit,” titling its article “The Natural.”

OK, Obama is tall (6 feet 2 inches), intelligent (Harvard Law, two bestselling books), and damn, he’s ambitious (running for president after two years in Congress). But he’s no natural.

As a correspondent for the Chicago Reader, I covered Obama’s 2000 campaign to unseat Bobby Rush, the ex-Black Panther who’s been a Democratic congressman from Chicago’s South Side since 1993. It’s the only election Obama has ever lost. As even one of his admirers put it, “He was a stiff.” You think John Kerry looked wooden and condescending on the campaign trail? You should have seen this kid Obama. He was the elitist Ivy League Democrat to top them all. Only after losing that race, in humiliating fashion, did he develop the voice, the style, the track record and the agenda that have made him a celebrity senator, and a Next President.

I got my first sight of Obama early that winter, at a church in the South Side’s Bronzeville neighborhood. 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. Obama was a mere two-term state senator, and this was half a decade before “-mania” was added to his 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 both to the birthplace of civil rights and a time-honored black 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 with 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, told me then, with a sneer, 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 back then, as I reported in the Reader: “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 state 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 who disdained the hard work of digging up votes.

“Barack is a very intelligent man,” Rich Miller, publisher of Capitol Fax, a statehouse news service, told me in 2000. “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 condescension to his surroundings.

Back in 2000, when I interviewed Obama in his cubicle-size office at a downtown law firm, he started the meeting by checking his watch. Then he dissed his congressional district, half-joking that he was more committed to the South Side than his opponents, because, number one, he’d moved there from Hawaii, and number two, he could have been raking it in on Wall Street.

“I really have to want to live here,” he said. “I’m like a salmon swimming upstream on the South Side of Chicago. At every juncture of my life, I could have taken the path of least resistance but much higher pay. Being the president of the Harvard Law Review is a big deal. The typical path for someone like myself is to clerk for the Supreme Court, and then basically you have your pick of any law firm in the country.”

Didn’t the people appreciate the sacrifices he’d made? To grind out a voter registration drive when he could have been earning $200K a year at a white-shoe firm? They didn’t. On Primary Day, Obama received 31 percent of the vote. He didn’t lose because he was “too white.” He lost because he was a presumptuous young man challenging a popular incumbent. If anything, his whiteness spared him a bigger beating. He ran strongly in Beverly, an enclave of Irish cops who had never forgiven Rush for his Black Panther past.

Trotter, who is plenty black, got 7 percent. In fact, Obama may be lucky he didn’t win. It’s harder to get to the U.S. Senate — or the cover of Men’s Vogue, or the drawing rooms of Manhattan donors — from a black-majority district.

Obama returned to Springfield a loser. The week of his defeat, he sat down to his regular poker game at the home of state Sen. Terry Link, a fellow Democrat from the Chicago suburbs. The same words were on the lips of every pol at that table: I told you so. Obama didn’t need to hear it. He knew he’d blundered.

“He made a lot of mistakes, and he learned,” Link says now. “He forgot who he was. That he’s Barack. He tried to sell to a crowd who wasn’t buying.”

Around that time, Obama also had a soul-searching drink with Miller, the Capitol Fax publisher. He was upset about the way Miller had characterized him, but “he took that criticism the right way,” Miller remembers six years later, “and he could have taken it the wrong way.”

“A lot of politicians, they know that they’re smart,” Miller says. “They know that they’re capable. It messes with their minds. Politics is not a game of qualifications. It’s a game of winning. That congressional campaign really showed that to him.”

On the state Senate floor, Miller saw a more focused, more collegial Obama, who began to take his work — and his fellow legislators — seriously. Using his experience in constitutional law, he passed legislation to curtail racially motivated traffic stops and to require police to videotape murder confessions. He sponsored legislation that added 20,000 children to the state’s health insurance program.

“I just can’t emphasize enough how much this guy became respected, and how transformative it was,” Miller says. “By 2004, he just had this aura about him.”

Even black legislators, who had resented Obama in his early years, were won over. He earned the respect of Trotter, who watched his fellow senator mature from a résumé in search of an office to an effective legislator. Trotter was so impressed, he now sits on Obama’s presidential exploratory committee.

“I wouldn’t say losing humbled him,” Trotter says, swatting away a term used by many of his white colleagues. “Barack is a competitor, and being a competitor, you don’t like to lose. When he came back, he really immersed himself in the process. He learned he had to get an agenda, to get issues he felt passionately about. He also learned some of those ‘get-along’ qualities you need to get a bill passed. He has proven himself to me that he can take advice. He’s not a one-man operation.”

I’d thought Obama had campaigned like an ass, but I expected him to run for the U.S. Senate. And I expected him to win. His white upbringing would appeal to suburbanites, while South Siders might figure that Obama was as black a senator as they were going to get, after the Carol Moseley Braun debacle. His braininess, his haughtiness, his sense of entitlement — they could only be pluses in a Senate campaign. They don’t call that place Ego Mountain for nothing.

In 2004, I went down to his Michigan Avenue campaign office to interview him for the Reader. His press secretary had already scolded me for the “negative” quotes in my last article. I was expecting another preening, insecure performance. But Obama charmed me right away. He did it to dozens of reporters that year. “Good to see you again,” he intoned, casually, gliding across the room like Fred Astaire playing Abe Lincoln. He had doffed his suit coat for shirtsleeves.

We went into his office, where, sitting under a giant photo of Muhammad Ali knocking out Sonny Liston, Obama tried out some lines he would use at the Democratic National Convention.

“There is a tradition of politics that says we are all connected,” he said. “If there is a child on the South Side who cannot read, it makes a difference in my life, even if it’s not my child. If there’s an Arab-American family who’s being rounded up by John Ashcroft without benefit of due process, that threatens my civil liberties. Black folks, white folks, gay, straight, Asian — the reason we can share this space is that we have a mutual regard. That’s what this country’s about: e pluribus unum. Out of many, one.”

That was the mission statement of 21st-century Obama. As a black candidate, he’d been too inhibited, too embarrassed, to force out phrases like “our community.” Finally, he was comfortable in his own skin, now that he’d accepted that the skin was half-white. Obama wasn’t born to be a voice of black empowerment, like Rush or Jesse Jackson. It’s not just a racial thing. It’s generational, too. Confrontational ’60s-style politics are not his bag. But as a multicultural politician, trying to find the unified theory of ethnic politics, he was rolling like Tiger Woods at the Masters. The aloofness was gone as well. Very intently, he laid out his plan for a federal Children’s Health Insurance Program.

“I think it’d be a good opportunity to lay the groundwork toward expanding health care to all the uninsured,” he said.

Obama was no longer selling himself. Now, he had a legislative goal and a strategy for making it happen. Or maybe, because he knew I was one of his skeptics, he was selling me on the idea that he wasn’t selling himself. In the words of an old police reporter, Obama makes grease look gritty. Just as he was looking two moves ahead, politically, I’m sure he was two moves ahead of my expectations. It was working. I was impressed that he finally believed in something. He was a big-government liberal, no weaseling about it.

“How would you have voted on the Iraq war resolution?” I asked.

“I would have voted no.” And then, with a simplicity that his old self might have thought simple-minded, he said, “I’m not opposed to all wars. I’m opposed to dumb wars.”

Then I asked him about his race against Bobby Rush.

“I got a good spanking,” he said, evenly. “I think that was youthful impatience on my part. I knew I was going to lose on Election Day. I was standing outside a polling place, and old ladies kept coming up to me and saying, ‘You seem like a nice young man, but Bobby hasn’t done anything wrong.’”

Later, when I called his office for follow-up questions, Obama jumped on the line and drilled me with more details of his healthcare plan. He also repeated his “E Pluribus Unum” speech, tweaking a few words. He was proud of that one.

A few weeks after that, I heard him speak at a North Side organic restaurant known for its liberal politics. The Heartland Café had welcomed Harold Washington during his run for mayor, and now it welcomed this new South Side phenom. Obama climbed up on the bandstand and filled that dining room with the same energy he’d project across the Fleet Center: “If there is a child on the South Side who cannot read … If there is an Arab-American family who’s being rounded up by John Ashcroft!” I was startled. The pedantic lecturer had been retired. Now, Obama was a fight announcer, a preacher and a motivational speaker, all on the same platform. Full of conviction, he drove his words into our ears like a carpenter pounding nails. The white folks loved him because he was liberal. The black folks loved him because, as one said to me, “We need someone who can reach beyond the race. He can go to Washington and talk their language.”

That wasn’t the Obama I’d known. But it was the Obama America came to know. I was sold. I voted for him twice that year. That July, the Democrats made him the keynote speaker at their convention. It was partly a defensive move against a rumored candidacy by ex-Chicago Bears coach Mike Ditka. Obama delivered a maiden speech to rival that of Hubert Humphrey in 1948, or William Jennings Bryan in 1896.

Terry Link believes that losing that congressional race liberated Obama to be the real Obama — the bright young charmer Link had met as a fellow freshman in Springfield.

“When he ran for the Senate, he was so comfortable,” Link says. “It’s like speaking from your heart, against speaking from notes. I thought, ‘This is the one I knew. It’s Barack again.’” Trotter saw a different dynamic: “He grew up around whites, so he’s very comfortable in those venues. That was obvious when he went over to [the South Side Irish enclave of] Beverly. His comfort zone was in those circles. That is who he is. This is the face of his grandparents.”

So what do you make of a campaigner whose persona changed so drastically in four years? That he’s finally learned to be himself, or that he’s putting on an act? He’s doing both. All great politicians are also great performers. Obama has been called the Democrats’ Ronald Reagan because he has the personality to sell the public on programs it might reject on their merits. (In Reagan’s case, it was supply-side economics. In Obama’s, it would be national healthcare.) They’re alike in another way. Reagan was a washed-up thesp, doing Vegas and General Electric ads, until he was cast as governor of California, then president. Obama has also grown into the character he was born to play: the great uniter who can bring together old and young, black and white, Democrat and Republican. So far, he’s playing it brilliantly. Even his comic timing has improved — he’s got his new audiences laughing at the same old Alabama/Yo Mama joke. And Bobby Rush has backed him for president.

Some of us, though, are still trying to figure out how he got to be Elvis, Lord Byron and Bobby Kennedy, all in the same dark suit.

“Charisma is in the eye of the beholder,” says Donne Trotter. Much as he admires Obama, he’s not going to drink The Juice over a community organizer from his old neighborhood. “I can’t define him as being this charismatic guy. He’s no Svengali or Jim Jones. Certainly, he has learned, though. He’s a very fast learner.”

This story has been corrected since it was originally posted.

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