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Thompson’s campaign believes it can make an issue of Bloomberg’s spending and wealth. “There was a different economic landscape during the 2005 election,” says Thompson campaign manager Eddy Castell. “No one resented an out-of-touch billionaire; everyone wanted to be a billionaire. Now it’s all Madoff, AIG, and Bloomberg saying he loves rich people.”

The mayor’s billions are at the core of his political power. But Bloomberg is exploiting fundamental weaknesses on the Democratic side that have nothing to do with his riches. That’s vividly apparent when it come to another main thrust of Thompson’s campaign: He’d be … nicer than Mike. Thompson, for instance, supports mayoral control of the schools, but with more input from parents. After the Dinkins-endorsement press conference, in which the former mayor said he was backing Thompson because the candidate supports “Democratic values,” I asked Thompson how he defined those values for New York in 2009. “It’s caring about the interests of middle-class and working New Yorkers and understanding that people are suffering,” Thompson said. “It’s about wanting to help small business and the self-employed. More than anything, it’s a belief in people.”

No one is against believing in people. But the core philosophy of the city’s Democratic Establishment has evolved little since the late eighties: It still revolves around identity politics and social services. We may be more enlightened, tolerant, and humane than other cities, but we’re also more highly taxed, with a rapidly eroding business sector and an inequitable public-education system. If Democrats want to win City Hall ever again, those are the kinds of issues they need to tackle. Unfortunately, there’s nothing resembling a local Democratic Leadership Council, the nineties outside-the-mainstream group that shook up Democratic-policy orthodoxy and gave the world Bill Clinton. The Drum Major Institute is the rare New York outfit to have wrestled with what a revamped progressive agenda might look like; in February, its executive director took a new job—on the Bloomberg campaign.

The local Democratic malaise, however, may be indicative of a larger shift. Perhaps we’ve entered a new, less partisan, two-tiered era of government. “The party structure produces legislatures, but it can’t groom executives—at the city, state, or federal level,” says a political strategist who has worked on both sides of the party aisle. “It’s not that people don’t want Democrats as mayor. They want someone who can positively affect their life. Rudy capitalized on a lot of Democratic ideas. It was Ray Kelly and others who’d talked about ‘broken windows.’ But Dinkins and the Democratic structure fought those ideas. The party continues to fight education reform that would make their candidates acceptable to a broader audience. Neither Obama nor Bloomberg came up through the ranks, and when it comes to executives, voters don’t want the organization man.”

There are some stirrings about remaking the organization. Scott Stringer, the 49-year-old Manhattan borough president, is no radical, but he recognizes that his party has gone stale. “One thing that Bloomberg and Spitzer—before the fall—changed was the notion that doing ‘good enough’ was enough,” he says. “Those days are gone. You have to grab issues instead of just taking issues that come to you. As New York Democrats, we have numbers in our favor, but we could lose it all if we don’t stand for something. We have not shown real leadership.” Other less-entrenched Democrats—like Brooklyn state assemblyman Hakeem Jeffries, 38—are showing encouraging signs of restlessness. Eric Gioia, 36, of Queens, running for public advocate, has wonky potential. The spiky Eva Moskowitz, 45, is just offstage, commanding charter schools. Stringer, who may challenge Senator Kirsten Gillibrand in a 2010 primary, sees nontraditional candidates jumping into the Democratic mayoral field in 2013. “Unless,” he says with a dark laugh, “Bloomberg decides he needs a fourth term.”

E-mail: chris_smith@nymag.com.


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