Bill de Blasio earned the little bit of beach time he’s enjoying this weekend in Puerto Rico. His three-year run to victory was a remarkable feat of political smarts and good luck. He sold his case with style and discipline, with one brilliant TV ad starring his son and a million repetitions of the phrase “a tale of two cities”—which his campaign strategists originally intended as a placeholder until they came up with a more original slogan. They never did, and De Blasio made the Dickens work—one indication of how deft he was at seeing that voters wanted a progressive corrective to twelve years of Mayor Michael Bloomberg. He rose from an obscure public office to handily defeat a better-known, more experienced front-runner in the Democratic mayoral primary and then won the general election by the biggest open-seat margin ever. All very impressive.
The reward is four years of nonstop headaches that will make being mocked as a socialist by Joe Lhota seem like happy hour. There is no shortage of major problems on the horizon: a $2 billion city budget deficit, more than 100 municipal labor unions clamoring for raises, the need to maintain public safety while easing up on stop and frisk. Those challenges will unfold slowly, and the men and women De Blasio hires for his administration will be crucial to addressing them. But De Blasio will, in all instances, be the central decision-maker. And how he handles his relationships with two of New York’s prickliest political players merits particular attention—not just because of the direct policy implications, but because of what each drama will reveal about De Blasio’s chances to succeed as mayor.
The first, and by far more important, is with Governor Andrew Cuomo. A small hint of how fascinating the dynamic will be came in September at a press conference on the steps of City Hall. The protocol at these rituals is pretty well established. The endorser introduces the endorsed—the candidate, the person the event is designed to boost—who closes the press conference on a high note. Yet here was De Blasio introducing Cuomo—the freshly minted Democratic nominee for mayor turning over the microphone and the spotlight to the incumbent governor, who proceeded to give a stem-winding speech that stole the show. It was a very odd speaking order—and one that top aides to the two politicians, um, discussed right up until the last minute.
Cuomo and De Blasio are genuinely friendly, nearly the same age, and have bonds going back twenty years. Their deepest day-to-day shared experience came when Cuomo, as HUD secretary, was De Blasio’s boss for two years, a pecking order that’s in the process of being drastically altered. Cuomo will still outrank De Blasio, but the mayor of New York City has a more powerful pulpit than the governor of the state. To say that the political media is eager for fireworks is a laughable understatement. There will certainly be strains and flare-ups. But I think the governor and the new mayor are going to surprise and disappoint us by getting along famously—not least because Cuomo sounds so eager to make the relationship work, both for one another and for New York. “A governor and a mayor, there’s a natural tension between the two. But there’s also a natural affinity,” the governor told me. “We’ve gone through hell and back, Bill and I—in our personal lives, in our political lives, and together. And neither of us are going to let anything disrupt the fundamental relationship.”
De Blasio is equally effusive. “[Working for Cuomo at HUD] was a great learning experience, in that he had this tremendous ability to stay focused on his core agenda,” he told me recently. “Andrew also understood the difference between working toward a goal and actually achieving the goal. We’re not graded on effort; we’re graded on results. So that was a very, very helpful time for me in understanding how to take a set of goals and get them to permeate an organization.” He sees the governor’s successful first year in office as something of a model for what he’ll do as mayor, pointing in particular to Cuomo’s 2011 Medicaid-redesign commission as a “great template” for how De Blasio will try to create at least the appearance of consensus on contentious issues.
Still, the biggest force in keeping the peace will be that both men have political incentives to function as partners. De Blasio wants to deliver on his campaign rhetoric about reshaping the city into a progressive capital; Cuomo wants to keep his left flank covered to roll up a big reelection margin in 2014—and just in case the chance to run for president in 2016 happens to arise. So what seems like an inevitable collision could turn out to be an opportunity for both to score points. De Blasio needs Albany’s approval for a signature campaign promise, raising taxes on the wealthy to pay for universal prekindergarten and expanded after-school programs; Cuomo says he’s all for beefing up education, but he’s determined to keep lowering New York’s taxes. If De Blasio slogs through the Legislature trying to win approval for the tax increase, only to run into a dead end with Senate Republicans, Cuomo might come up with an alternative route to fund the program. Or Cuomo could persuade De Blasio to resolve the labor contracts before pursuing the schools idea. “They can sort this out,” a Democratic colleague says. “Unless Bill presses for a tax increase for the sake of a tax increase. That’s not a fight the governor would shy away from.” De Blasio told me that he doesn’t see any alternative to raising levies on the rich: “To me what’s quite obvious is that there is no other practical pathway.” But: “If new ideas emerge, we’ll cross that bridge when we get to it,” he said. “I think, in terms of the larger debate we’ve had in this city, there’s no question that a lot of people in this town want to see folks who’ve done well give back to society. There’s no question about that. But this is ultimately a practical proposal.” And De Blasio and Cuomo are nothing if not practical politicians.
On another front, however, the new mayor seems ready to go to war. De Blasio and Eva Moskowitz overlapped for four years in the City Council, and for the most part cordially, which is somewhat unusual, because the hard-charging Moskowitz has a talent for getting under people’s skin. After leaving public office, she founded Success Academy in Harlem; since 2006, it has grown to operate 22 charter schools in four boroughs and racked up impressive test scores, as well as a series of complaints that the schools cull low-performing and special-ed students. That’s made Moskowitz a lightning rod for charter opponents, and during the Democratic primary she was a convenient target for contenders trying to endear themselves to the teachers union, De Blasio among them. He proposed that charters already sharing space with conventional schools start paying rent—but his attacks took on an unusually harsh personal edge. “There’s no way in hell Eva Moskowitz should get free rent [for her schools], okay?” De Blasio said at a forum in June. Even his allies found the vehemence a little hard to figure. “I understand Bill’s points about income inequality, affordable housing, stop and frisk,” one Democrat says, “and how his critique of education reform fit into his anti-Bloomberg attack. But the charter-school stuff struck me as less genuine. Many of those schools are serving the poor kids he cares about.”
Indeed, De Blasio now says he’s willing to learn from the charters that work best. “I think there are some charters that are doing a good job, that are representative, that provide a good model, and we’ll work with them,” he told me. “But they will never replace the core capacity of our traditional public schools.”
Perhaps that’s what’s really fueling his annoyance with Moskowitz. De Blasio’s main problem with charters isn’t philosophical—it’s that they suck up a disproportionate amount of political time and attention. He’d rather ignore the charter-school movement than kill it, and instead devote his educational energies to improving the 90 percent of the city’s schools that aren’t charters. Yet one of the many things that’s not clear about De Blasio as a leader is whether he can separate business from personal. Bloomberg, as mayor, was generally able to scorn an adversary one day and consider him an ally the next. Moskowitz will provide an intriguing test case, because she seems determined to goad De Blasio into backing up his campaign rhetoric. In October, she led a save-the-charters protest march across the Brooklyn Bridge, and she isn’t backing off now. Wasn’t the Million Moskowitz March prematurely confrontational? “Bill de Blasio took on Success Academy very directly in his campaign and threatened our very existence,” she says. “To fulfill his campaign promise [about charging rent to charters] he would have to hurt the very children he genuinely wants to help. And that I want to help. I’m delighted that the mayor-elect cares about equality, because that means equality of funding, that means equality of space. And charter schools have been discriminated against in so many ways. And I’m not sure he’s aware of all those ways.”
Bill de Blasio has plenty of reasons to be friends with Andrew Cuomo and enemies with Eva Moskowitz. Finding a productive balance in those relationships, and in dozens of other conflicting interests, will be tougher. But achieving that balance will determine whether De Blasio can go from righteous candidate to agile mayor—and actually bring New York’s two cities closer together.