Obama: How He Learned to Win

By Michael Weisskopf/Chicago

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-elite 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.

From the ashes, though, Obama could see a way out. The only ward he had won was the largely white working-class Irish Catholic 19th ward, where the local party organization had endorsed Rush but a state legislator, Tom Dart, broke ranks for Obama. Dart walked the precincts and marched with Obama at the annual South Side St. Patrick's Day parade, passing out O'BAMA buttons with shamrocks. Nearly three-quarters of the ward--a conservative community of cops, firefighters and schoolteachers--went for Obama, suggesting a wider reach among white voters. "He didn't need to be pigeonholed in his Hyde Park base," said Dart.

But if Obama was going to make his great leap forward, he would need the help of men like Emil Jones. A former sewer inspector in Chicago, Jones worked his way up the Democratic machine on the Far South Side to become Illinois's senate president in 2003, a pork-barreling, wheeling-and-dealing powerhouse. Early that year, he met privately with Obama at the statehouse. Obama had passed up various statewide races but now had found one to his liking: the U.S. Senate seat held by Republican Peter Fitzgerald, a quirky maverick up for re-election in 2004. If Obama were to have any hope of becoming the Democratic nominee, he would have to overcome two weaknesses exposed in 2000: shaky support among working-class blacks and the dearth of party regulars. Jones, now president after a Democratic takeover of the state senate, held the key to both problems. "You've got a lot of power," Obama told him. "You have the power to make a United States Senator." Jones asked Obama who, exactly, he might have in mind. Obama then described his strategy for getting elected. Jones recalls that the two men discussed the idea for a while and then he said, "Let's go for it."

By embracing Obama early, Jones stopped pivotal endorsements of rivals. Candidate Blair Hull, who made a fortune in securities trading, had a claim on the support of Governor Rod Blagojevich, whose 2002 victory Hull had helped underwrite. But, as Jones put it, "the governor needs support for his initiatives, so naturally he's not going to take a chance at alienating me." Blagojevich stayed neutral. Illinois comptroller Dan Hynes was the presumptive favorite, the son of a former state senate president, longtime 19th-ward boss and close Daley ally. The AFL-CIO was gearing up for an early endorsement of the younger Hynes. Jones caught wind of the plans and called its president. "If you proceed in that direction, you lose me," Jones told her. The union backed off, giving him and Obama time to line up support from affiliates that had large and heavily black memberships--teachers, government employees and service workers.

With Hull and Hynes likely to split the white vote, Obama would need blanket support from African Americans. But in seven years in Springfield, he was best known for passing ethics reform. The GOP majority hadn't made it any easier to pass social-justice legislation. Now Jones was in control of the body and its agenda. He picked Obama to steer and ultimately get credit for laws that passed in the second half of 2003 after years of demands by the black community: death-penalty reform, taping of homicide interrogations, fattening tax credits for the working poor and a measure to curb racial profiling.

Though Jones leaned on the black caucus to get behind Obama, many saw him as an undeserving outsider who jumped the line, who wore ambition on his sleeve. Some were "very upset" to see Jones hand important bills to Obama instead of spreading out the goodies to other Democrats, said Delmarie Cobb, a black Democratic consultant who supports Hillary Clinton for President. Jones was less successful outside Springfield. Some old-line black politicians in Chicago backed Hynes out of loyalty to his father. Rush endorsed Hull.

Obama, meanwhile, had junked his starchy speaking style in favor of something that helped him shore up his base. Dan Shomon, his campaign manager against Rush, believes Obama learned the art of public speaking at the scores of black churches he visited in 2000, absorbing the rhythm and flourishes of pastors and watching how their congregations reacted. David Mendell notes in his biography of Obama how the candidate would "drop into a Southern drawl, pepper his prose with a neatly placed 'ya'll' and call up various black colloquialisms." He rarely missed a chance to speak at Sunday services in black churches, where, Mendell writes, he linked his candidacy to the larger march forward of African Americans. He emphasized his Christian faith and often mentioned his pastor, Jeremiah Wright. While Wright has been a liability to Obama this year, in 2004, when Obama faced doubts on racial authenticity, he was a campaign asset. "It affirmed his roots," said Cobb.

Obama drew from other parts of his life story to broaden support among whites. His rise from a modest upbringing to the pinnacle of U.S. education drew a connection to the life struggles of ordinary people. Even his rival Hynes admired Obama's appeal to "anybody who may have shared his passion for trying to make it." Partly as a result, Obama won the endorsements of some white lawmakers from small towns whom he'd gotten to know in legislative battles and occasional poker games played amid cigars and beer.

And while Obama couldn't win the support of the Daleys' political machine--he knew they would back Hynes--he shrewdly planted some political seeds. He wrote Bill Daley, a longtime Democratic wise man, saying that while it was only right for the Daleys to support a loyal friend, he hoped they would be for him if he won the primary. "I thought, that's a very smooth move," said the younger Daley, who now supports Obama for the White House.

"I guarantee you, I can win"

Obama was now politicking at a high level and building a different kind of organization to pay for it. In the 2000 loss to Rush, Obama raised $600,000, an eye-popping figure for a first-time congressional candidate. Now, four years later, Obama laid down a challenge to Marty Nesbitt, a top fund raiser, as he eyed the U.S. Senate. "If you raise $4 million, I have a 40% chance of winning," Nesbitt recalls him saying. "If you raise $6 million, I have a 60% chance of winning. You raise $10 million, I guarantee you I can win." Said Nesbitt: "It was a matter of having the money to tell his story."

Obama had already opened a rich vein of political cash in Chicago's black business elite, a new generation of corporate executives, capital managers, consultants, manufacturers and bankers. He put a flamboyant Chicago real estate tycoon named Tony Rezko on his finance committee to hit up the developer crowd. But to raise $10 million, he would have to win over Chicago's biggest political donors, many of them Jewish professionals and business owners, known as lakeside liberals. They lived along the North Shore of Lake Michigan, and most had had no personal contact with Obama.

Many of them did know Obama's black inner circle, however. Nesbitt was close to Penny Pritzker of the Hyatt hotel clan, who had helped finance Nesbitt's airport-parking company. Riding home together from a board meeting in 2002, Nesbitt mentioned Obama's Senate plans and asked her to lend a hand. She was initially skeptical--"Didn't he just lose a congressional race to Bobby Rush?" she asked--but agreed to hear Obama out. She invited Obama to her Michigan summer home for a weekend. He won her over, landing on his finance committee a Pritzker whose Rolodex contained the names of Chicago's leading business, cultural and philanthropic figures.

Obama raised almost $6 million in the primary, and some of it came from sources Obama now shuns--$180,000 from political-action committees and $40,000 from lobbyists, according to the Center for Responsive Politics. More than half his war chest came from people working for industry groups--legal, securities, real estate, banking, business services, health care, publishing, utilities and insurance among them. Rezko raised $160,000 for the primary and later general election--funds Obama gave to charity after Rezko was indicted on corruption charges for which he's now being tried. Obama's contributor list made some uncomfortable. "Is he really reform-minded, transcendent, clean, fresh and new, or is this just another politician?" asked a donor wooed by Obama but signed by Clinton. "The answer is, he's just another politician."

Obama's lunge for high office would not prove much of a contest. His Democratic rivals tore each other up, letting Obama's mostly keep to the high road. He never threw a lot of punches, but he never had to take one either. He lured both blacks and whites to his coalition without facing a clash of their interests. And the speech that turned out to be his most important won him the least attention. Not long before he announced his Senate candidacy, he agreed to speak at a downtown rally against the U.S. invasion of Iraq. "I don't oppose all wars," he said, "what I'm opposed to is a dumb war." Obama wasn't even mentioned in a Chicago Tribune story the next day. But his prophetic words would power his campaign for the nomination four years later.

The Senate race turned into a rout, with Obama taking nearly 53% of the vote in a three-way race. Not only did he score a landslide victory in the African-American community, but he also handily won a pair of ethnic-white wards on Chicago's Northwest Side. And he won a third of the vote in downstate Illinois, backed by college students and farmers.

The commitment of Obama's new coalition was never really tested in a difficult campaign; Obama went on to crush a Republican stand-in, Alan Keyes, after the incumbent decided not to run and the GOP's nominee had to withdraw amid a scandal. But the seeds of Obama's political future were planted during that Democratic primary campaign. At his primary victory party in May 2004, he noted the improbable triumph of a "skinny guy from the South Side with a funny name like Barack Obama." And then he repeated a line that had capped his campaign commercials: "Yes, we can. Yes, we can."