Obama: How He Learned to Win

Barack Obama had not been in politics for long when he got his tail whipped by a veteran Chicago Congressman in his own backyard. For a brief period that followed, Obama seemed a bit unsure about what to do with his life--the same kind of unsettling early stumble made by others who went on to seek--and often win--the presidency. Yet within four years, Obama had won a seat in the U.S. Senate. Less than four years after that, he has all but clinched the Democratic nomination for President.

How did the man who is virtually certain to face John McCain in the fall come so far so fast? Much of the answer can be traced to the lessons of his first thumping. It was after that brief race in 2000, say dozens of aides and associates who spoke with TIME, that Obama learned how to be a politician. He jettisoned his Harvard-tested speaking style for something more down-home. He learned how to cultivate those in power without being defined by them. And he learned how to be different things to different people: a reformer groomed by an old-fashioned machine boss, an African American heavily financed by white liberals, a Harvard lawyer whose bootstrapping life story gained traction with white ethnics. Abner Mikva, a former federal judge and Congressman from Chicago, credits Obama with figuring out "how to appeal to different constituencies without being inconsistent."

At various points during Obama's bid for the Democratic nomination, all those skills have been on display. This is the story of how he mastered them.

Gambling--and losing

In the great midcentury heyday of Chicago's Democratic machine, politics was open only to those with a sponsor--"We don't want nobody nobody sent," a ward boss famously said. By the time Obama got into the game in the 1990s, it was no longer an exclusive club. The centrally controlled party organization had splintered into a loose group of ward committees that operated like autonomous fiefs. Still, old practices died hard; the same virtues of loyalty and familiarity were rewarded by new bosses who expected political newcomers to pay their dues--and wait their turn.

One exception was Hyde Park, a small, integrated, partially gentrified neighborhood of professionals and University of Chicago professors, with a long tradition of independent politics. Obama moved there as a newly minted lawyer specializing in civil rights cases and lecturing at the university's law school. In 1996 he won his first political election to represent Hyde Park in the state senate, using legal challenges to keep rivals off the ballot. But after three years in the state capital of Springfield, he got restless and turned an eye to the seat for the First Congressional District of Illinois.

The First had the longest continuous black representation and one of the highest percentages of African Americans of any district in Congress. Since 1992, the First had been represented by a man with his own claim to history. Bobby Rush co-founded the Illinois Black Panther Party before going mainstream as an alderman and ward committeeman. But Rush stumbled badly in early 1999 when he challenged incumbent Richard M. Daley in the Democratic primary for the mayor's job. Rush lost, doing poorly among black voters and failing to carry his own ward.

His misstep made Obama think he could take Rush on. So in Obama jumped--only to discover he would have to fight for every vote. Rush started off with 90% name recognition, vs. 9% for Obama, a poll showed. The challenger had hoped to find common ground with Daley, but the mayor saw no percentage in crossing a sitting Congressman. Daley, according to his brother Bill, told Obama that just because Rush had been creamed for the mayoralty didn't mean he could be dethroned by a newcomer. "You're not going to win," Daley said.

Obama argued that Rush had failed in leadership and vision. But his delivery was stiff and professorial--"more Harvard than Chicago," said an adviser who had watched Obama put a church audience to sleep. The problem was deeper than speaking style. Obama was a cultural outsider. Rush attacked his Ivy League education, using the E word for the first time. "He went to Harvard and became an educated fool," the Congressman told the Chicago Reader. "We're not impressed with these folks with these Eastern-élite degrees." Not growing up on the South Side raised other suspicions about Obama. So did his white mother and his Establishment diction. Obama's first encounter with racial politics was over the perception that he wasn't black enough. "Barack is viewed in part to be the white man in blackface in our community," state senator Donne Trotter, who was also running for Rush's job, told the Reader.

The contest raised another question that haunts Obama to this day: Does he have the will to win? Halfway through the race, he took his family to Hawaii for Christmas, missing a key vote in Springfield on legislation to make illegal gun possession a felony. The measure was intended to deter violence in the kind of gun-ravaged neighborhoods he was seeking to represent. Illinois's governor, who called a special session to pass the measure, pleaded with Obama to come back. His staff did too. But Obama, who had previously supported the bill, refused to return for the vote on grounds that his 18-month-old daughter was sick. When the bill lost narrowly, Obama came in for a large share of the blame. Rush, whose 29-year-old son had been gunned down on the South Side a couple of months earlier, said there was no excuse for missing "one of the most important votes in memory."

It fell to Bill Clinton to deliver the coup de grace. The President broke his policy of staying neutral in primaries and endorsed Rush in a glowing radio spot. When it was over, Rush piled up 61% of the vote, compared with 30% for Obama. He lost the most heavily black wards by more than 4 to 1. The race was called before Obama could even make his way to a would-be victory party at the Ramada Inn in Hyde Park. "I confess to you," he told about 50 supporters on a chilly March evening, "winning is better than losing."

Once more, with friends

The campaign left him $60,000 in debt and unsure of his future. At 38, he was a state legislator in a party out of power, a black politician trounced in the black heartland, an outsider in the tribal world of Chicago politics. His long absences from home had angered his wife. "He was very dejected when it was over," said Mikva, "and thinking of how else he could use his talents." When a nonprofit group dangled a high-paying job, as director, Obama was so nervous--for fear that he might get it--that his hands were shaking on the way to the interview, a former aide reported.