The group largely sat out the stimulus fight, holding house parties and continuing to fundraise, while gearing up for Obama’s signature policy initiative. “I think we all knew that health care would be the big one,” Jeremy Bird, the organization’s 31-year-old deputy director, told me. But when the health care debate arrived with a fury this summer, OFA ran into problems.

The first was timing: Staff were still filtering into the states in July–and, because the Senate Finance Committee hadn’t produced a bill yet, OFA had little concrete to advocate for, even as conservatives found plenty to argue against. The second was tactical: Obama’s campaign had never used the kind of in-your-face antics the tea-partiers embraced, focusing instead on story-telling and canvassing. “What you see on the right is an organizing model that’s based on grandstanding in front of cameras, in August for example,” Bird says. “That’s not what we ever did on the campaign. Our organizing was the nitty gritty. I mean it really was the real, hard-core organizing work that we think moves folks and wins elections and changes peoples’ lives and is based on person-to-person conversations.”

But the biggest problem was built into OFA’s very structure–the structure that Plouffe had wanted and Hildebrand had warned against. Obama’s people had created something both entirely new and entirely old: an Internet version of the top-down political machines built by Richard Daley in Chicago or Boss Tweed in New York. The difference (other than technology) was that this new machine would rely on ideological loyalty, not patronage. And that was a big difference. The old machines survived as top-down organizations because they gave people on the bottom something tangible in return for their participation. By contrast, successful organizations built mainly on shared philosophy tend to be driven by their memberships.