De Blasio seems to have replaced Anthony Weiner and John Liu as the Democratic contender who gets under Bloomberg’s skin the most; when De Blasio floated the idea of raising taxes on the city’s wealthy, the mayor called it “about as dumb a policy as I can think of.” If De Blasio, in third place in early polls, gets traction against Quinn, it will lead to a fateful strategic crossroads next year. Bloomberg’s new super-pac spent $9 million in a largely successful debut this fall, and the city’s political class assumes the mayor will be unable to resist pouring money into the race to follow him to City Hall. Whether it would work—as a way to extend Bloomberg’s legacy by helping elect Quinn—is hotly debated. “I think he’s a very bad messenger in a Democratic primary,” a De Blasio ally says. “It’s hard to see a Bloomberg-financed pac doing anything but hurting the candidate he’s trying to help.” Another Democrat, unaligned with any of the current candidates, scoffs. “It’s $10 million against $2 million or $3 million,” he says. “Would the Times editorial page be apoplectic? Perhaps. But who cares? The ads are out there doing damage. If that happens, nothing you’re writing now amounts to anything.”
Gee, thanks. Big money, smart tactics, and cold demographics may well determine the winner. Yet this city has an uncanny way of matching new mayors to the moment. In 2001, Bloomberg’s millions wouldn’t have mattered without 9/11, after which a business résumé suddenly seemed the exact right credential to lead a city with a reeling economy. In 1986, a gang of white Howard Beach thugs chased three black men whose car had stalled; one of the men, Michael Griffith, fled onto Shore Parkway and was killed by a car. That tragedy helped form the context for the emergence of David Dinkins.
Today, De Blasio is around the corner from New Park Pizza, the place where the Howard Beach episode escalated. New Park still sells great pies, but 26 years later its customers are the unremarkably amazing New York multiracial mix. The mood that will elect the next mayor has yet to cohere, and key blocs of votes—especially Latinos—are up for grabs. But part of the game will be whether Bill de Blasio can paint Chris Quinn as too Manhattan, and too much like Mike Bloomberg, to be a mayor for all the city.