Obama: How He Learned to Win

Obama had already opened a rich vein of political cash in Chicago's black business élite, 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."