Obama: How He Learned to Win

(2 of 3)

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."