De Blasio’s signature campaign promise will test his political skills immediately once he’s elected—actually, the machinations are well under way. De Blasio needs state legislative approval to raise taxes on wealthy city residents and fund the pre-K and after-school programs that he says will slowly close the economic divide. Governor Cuomo, who says he’s determined to lower New York’s taxes, has questioned whether the proposal is merely campaign rhetoric. “Never forget that Bill worked for Andrew” at HUD, a Democratic strategist says. “And Andrew will always see the relationship that way.” The dynamic won’t be nearly that simple, though. De Blasio’s camp believes a landslide in November will become momentum in Albany. “Andrew is going to want De Blasio to help him next year, big time, on the left,” a pol who knows them both says. “Now, here’s the dilemma for De Blasio: What does he do if Andrew gives him the money for pre-K but eviscerates poor people outside the city?”
De Blasio often begins his answer to tough questions with a version of “Let me frame this,” and then proceeds to rearrange the subject to his advantage. It’s a skill he shares with Cuomo—and one reason he thinks he understands the governor’s psyche so well. “Bill is New York’s leading Cuomo-ologist,” a liberal strategist says. “Whenever we had questions about Andrew, it was, ‘Call De Blasio!’ ” He is being careful not to antagonize the governor even before he’s officially mayor. The pending state referendum on the expansion of casino gambling provides an intriguing example. You might expect De Blasio, the “true progressive,” to oppose such a regressive industry. But in addition to seeing policy benefits from casinos, De Blasio the pol knows that the referendum is highly important to Cuomo. “I don’t accept the characterization [that legalized gambling is incompatible with progressive values], first of all,” he says. “That may get back to my mother’s pragmatism. The industry exists. It’s state sanctioned when you call it Lotto. The money and the jobs are going elsewhere; we’re not in a position to let that kind of economic impact go elsewhere. And you know, since that is the reality, certainly the financial impact on a city, if we get $50 million, $100 million, whatever the final figure is each year for our schools, you know, that’s gonna do some good. I think it’s a very practical equation. I think we have to, at the same time, try to address the underlying dynamics—help people get the best jobs, the best education possible, then they will make their own choices.”
The financial industry won’t be going away, either, despite its fears of De Blasio. One fringe benefit to his enormous general-election lead over Joe Lhota is that De Blasio has had time to sit down with Wall Street giants and real-estate-industry players, cashing their checks and parrying their skepticism. “I don’t think we have to have a philosophical ‘Kumbaya’ moment,” De Blasio tells me. “I think it’s clear I’m a progressive and that if the people choose me, I’m going to take this city in a progressive direction to address these inequality issues, and I think that certainly some of the business leaders I have met are not particularly interested in doing that. Some are, to be fair—there are some very progressive people within the business community who have told me with energy that they agree the inequality crisis is getting out of hand. All I care about there is where we have to work together practically to create jobs.” A top Democratic strategist who has worked with De Blasio puts it much plainer: “He’s more pragmatic than progressive. He’s a deal guy—which is why Wall Street should love him. They’re deal people, too!”
De Blasio is far from selecting a City Hall lineup, at least publicly. His campaign aides quickly bat down the names of potential commissioners that have been floated in the media, leery of looking overconfident, even with a 44-point lead. “I’ve been talking to people for advice for the last year or two while simultaneously assessing them,” De Blasio tells me. “You can do a lot of deep thinking, a lot of playing things out in your mind. If I’m the one [elected], I’m certainly not going to be caught flat-footed.”
The exception to this wariness, however, has been instructive. De Blasio himself has talked up two people he’d consider selecting for police commissioner. The first, Bill Bratton, is associated with dramatic turnarounds in both Los Angeles and New York—and, usefully for De Blasio, Bratton is also remembered positively by many in the city for clashing with Rudy Giuliani. The second, Philip Banks III, is currently chief of department in the NYPD—and, usefully for De Blasio, Banks is African-American. Both are law-enforcement lifers and very much in the mainstream of policing theory and practice, which allows De Blasio to tamp down worries that he’d make radical changes in a department that’s reduced crime to record lows. But, again, the floating of these names is more political than executive. De Blasio is savvy enough to understand the downsides: Bratton is a media magnet, and some police insiders consider Banks too nice a guy to run the department forcefully.