Campaign 2008: How Big Money Picks a Winner

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Illustration by Dave Wheeler

Dave Wheeler for TIME

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On the G.O.P. side, McCain already has 21 of the biggest bundlers from the last Bush campaign, more than any other Republican hopeful. But Barry Wynn, a former Bush Pioneer and finance chair of his 2004 campaign, is helping Rudy Giuliani raise money in South Carolina. Giuliani's leadership post-9/11 was, of course, a factor in Wynn's choice. As for Rudy being a nontraditional Republican, for Wynn, that's exactly the point: "We need to rebuild the brand." Wynn committed after both Romney and McCain came calling. "Oh, I have had my lunches. And my breakfasts," he says with a little groan. But in general, the courtships for Republican donors have been low key. The Bush White House has not signaled a preference for a successor, so there is little sense that backing one candidate or another would be a betrayal of the President.

In the small world of Washington, there are many who have simply come to know a certain candidate personally and feel something akin to a social obligation. Says a high-level Democratic activist: "Your children are in the same school. You see them in nonpolitical circumstances. People wind up making choices that surprise people because of existing loyalties." There's the story of the young ex-Clinton aide who failed to sign on to Clinton's campaign and instead went to work for Senator Joe Biden. Why? Because Biden gave her husband his first job, and she felt she had to--in the words of someone close to her--"respect that relationship." But old relationships can take you only so far, and candidates will have to continue to schmooze, seduce and cajole big money to join their team. Says a G.O.P. member: "You can't get to $100 million at $2,300 a clip"--the limit set by the McCain-Feingold reforms in 2002--"by just calling your friends. Nobody has that many friends."