The $75 Million Woman

By early February, Obama had recruited billionaire hotel heiress Penny Pritzker to head his national finance team. The two had met when Michelle Obama's brother was coaching her children's basketball team, and they became friendly before Obama launched his political career.

When Obama broached the idea of running for Senate, Pritzker recalled, she had her doubts. "We decided we would put aside political assessments about odds of winning or losing," she said. A similar reluctance gripped her in the face of a presidential bid against a Clinton, but she said her husband convinced her that "you have to find a way to do this."

Obama also landed several Kerry bundlers, including Silicon Valley venture capitalist Mark Gorenberg, and lured two former fundraisers of Bill Clinton's, Boston financier Alan Solomont and New York investment manager Orin Kramer. Solomont said he was surprised by the notice his decision received. "I wasn't looking to make a statement about the Clintons," he said. "My decision wasn't in any way based on less affection or respect for her. [Obama] just had this energy. I could tell this was going to be something different."

Smoot knew Obama was not alone in pursuing potential fundraisers. Some were getting daily calls from presidential candidates. One potential bundler contacted by Smoot was Norman Hsu, one of the most reliable donors from her tenure as finance chair for the Democratic Senatorial Campaign Committee. Hsu would later become mired in scandal as a top bundler for the Clinton campaign, but he was regarded at the time as a prime target because of his reputation for producing a steady flow of campaign cash.

In an interview -- before it was reported that Hsu was a fugitive trying to outrun a 15-year-old conviction for running a Ponzi scheme -- he recalled his call from Smoot. She asked what he thought of Obama's bid and whether he might consider helping. "I told her, 'You're asking for an unbiased opinion from someone who is very biased.' She knew I was loyal to Senator Clinton. I told her she was asking the wrong person. We both respected each other well enough not to talk about it after that."

Two key donors in Philadelphia, lawyers Richard L. Shiffrin and Mark A. Aronchick, took weeks to decide between the two campaigns. A key Clinton aide invited the two men and their wives to Washington. "It was one of the most unbelievably thrilling and well-organized days of anything I have done in all my years in politics," Aronchick said. "And I don't get dazzled easily."

Smoot had an aide call and propose that Obama meet the two lawyers at the Philadelphia train station. They could ride with him to a fundraiser. Later, she asked Pritzker to reach out. But both enlisted with Clinton and say they have since bundled more than $650,000 for her.

Online Successes

Smoot and Pritzker soon began talking about another, less glamorous component of the Obama fundraising machine.

"It seemed to me, consistent with the grass-roots nature of the campaign that Barack had envisioned, that online fundraising ought to be successful," Pritzker recalled telling Smoot. "The question was, could we execute?"

Smoot had hired Meaghan Burdick, 31, to coordinate fundraising online and through the mail, the same job she had been doing for the Democrats' congressional campaign committee. The prospects looked uncertain, at best, Burdick said. "The senator didn't do much mail in his Senate campaign, and he really didn't do a whole lot of fundraising, period," she said. But Joe Rospars, Obama's Internet guru, thought he saw potential in the grass-roots approach the campaign seemed to be taking. He wanted to design a Web site, he said, that would "take it to the people."

Burdick's first appeal through the mail was shipped out to a list of 800,000 people she had cobbled together using addresses collected during Obama's earlier campaigns and ones rented from unusual sources, including Sojourners magazine and the Martin Luther King Jr. Library in Atlanta. The three-page letter evoked themes of "hope" and "change" and closed with a quote from King: "The arc of the moral universe is long, but it bends towards justice."

More than 17,000 donations came back, Burdick said -- about double what she had expected.