Who Will Run New York? It's a Wide Open Race

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DAVID SHIPLEY: I thought we would start the conversation the way you started your interviews with the ’20-’21 mayoral candidates: with a little history, specifically your history around New York City politics, which gave you a special perspective on the candidates. Can you fill us in?

HOWARD WOLFSON: I got my start in New York politics working for Congresswoman Nita Lowey, who represented part of New York City. And then I worked on Chuck Schumer’s 1998 Senate campaign against Al D’Amato. Worked on Hillary Clinton’s 2000 Senate candidate campaign against Rudy Giuliani and then Rick Lazio; worked on her re-election in 2006; helped Andrew Cuomo run for attorney general in 2006. And then worked on Mike Bloomberg’s 2009 mayoral campaign and became a deputy mayor for him during the third term, from 2010 through 2013.

DS: As you look at these interviews, do you see themes that would be useful to highlight as New Yorkers try to make sense of the candidates?

HW: One of the most interesting, I thought, was that they all essentially have the same critique of Bill de Blasio, which is that he is well-intended: “We like universal pre-K, but he’s not a good manager and not able to really deliver on a lot of his ideas and promises.” That critique undergirds a lot of their messaging, which is, “I’ll be a progressive who gets things done.” You get that from many of the candidates — a sense that the city has been profoundly shaken by Covid, but that it is also dealing with a set of challenges that are also profound around inequity, economic inequity and racial inequity.

DS: Is it possible to order the candidates along some subjective political spectrum?

HW: I think there are a couple of different ways you could group them. One is left versus more moderate. Maya Wiley, Dianne Morales and Scott Stringer are the most progressive of the candidates. And then Andrew Yang, Eric Adams, Kathryn Garcia, Shaun Donovan and Ray McGuire are somewhat more moderate. I want to use that term advisedly because even the ones who are moderate are pretty progressive. There is definitely the outside versus inside. McGuire and Yang are obviously much more of the outsiders, and the rest of the field has fairly significant experience either in government or politics.

DS: How connected were these candidates to the city that you see? Do they know what’s going on at street level? Are the right issues getting attention?

HW: The way I think about campaigns is that the successful candidate is one who has their finger on the pulse of the city, identifies the zeitgeist, marries that with their own biography in a way that is authentic and real, and then communicates that effectively. When you think about the de Blasio campaign of 2013, you have a guy who understood that there was profound unease with some of the economic and racial inequities in the city. He spoke about his own family and his own experiences effectively in that context.

Or Mike Bloomberg in 2001 after 9/11 — people are worried, they’re scared. They don’t know whether the city is going to really survive. And Mike presents himself as a business figure who can bring the city back.

In a lot of ways this campaign began last year in a different New York. Covid has been such an overwhelming presence in our lives that it’s understandable that candidates were running in its shadow. But the spring of 2021 is not the spring of 2020. And I do wonder whether all of the candidates have adjusted to the new reality that we face coming out of Covid. It’s not clear to me that the candidates have really identified the zeitgeist. The one candidate who I think has picked up on some of the optimism and hope that people have coming out of Covid is Andrew Yang.

DS: As a former deputy mayor, what do you look for in a mayor?

HW: Someone who is focused on hiring — really takes it seriously. Someone who is comfortable being challenged. Someone who can delegate responsibility but also exercise oversight. It’s tough — you have to pay attention to the nuts and bolts of government while also imagining what the city should look and be like in 10 or 20 years. I guess the last balancing act is that you have to be comfortable with both the operational and the performative aspects of the job. When you’re at that podium, and something has happened in this city that’s at the center of so much, the eyes of the world are on you.

DS: I got the sense from the interviews that you felt that this seemed to be a pretty impressive group. Do you agree?

HW: Nicole Gelinas, who writes for the New York Post, said that there’s somebody in this race for everyone. I think that that’s right. I came away impressed after my conversations — obviously everybody has different strengths and weaknesses, but I think this is a field of people who should be able to produce a quality mayor.

DS: Let’s go through a few issues — recognizing that the pandemic runs through everything. Who in your view thought most rigorously about recovering from Covid’s economic damage?

HW: What stayed with me from these interviews were some of the candidates’ personal stories. Eric Adams — his story of becoming a police officer, being the victim of police abuse as a teenager, being recruited by activists and ministers to join the force, to fight abuse from the inside, taking on misconduct while also fighting crime is just a really interesting, powerful, potentially unifying story. Maya Wiley’s really tragic and poignant story of literally watching her father drown in a boating accident and her efforts to seek help for him afterwards were incredibly powerful, very moving. Ray McGuire has got this incredible American success story: kid on the other side of the tracks, up from the bootstraps to the pinnacles of success on Wall Street.

But around Covid and the economic recovery, I’m not sure that I could really tell you what some of the fine print was. With the exception of Yang’s universal basic income, I’d be hard-pressed to recapitulate some of the other plans.

DS: Did you have a clearer sense on education?

HW: You have candidates who are more rather than less supportive of charter schools. That was an interesting divide. I asked Scott Stringer — who just got the United Federation of Teachers’ endorsement — whether there were any areas of education policy where he differed with the UFT and he couldn’t come up with any. Someone like McGuire, for instance, I think is much more supportive of charter schools, someone like Adams also, than Scott Stringer or Maya Wiley.

DS: What about policing and public safety? I should add that we’re talking about this the morning after Derek Chauvin was convicted in the murder of George Floyd.

HW: This was one of these areas where it was almost like it was still the summer of 2020, where murder went up 40% last year. It’s up 20% this year over last. I was surprised that more of the candidates didn’t speak to the imperative of reducing crime and also ensuring respectful, responsible policing. Some did; it’s a big part of McGuire’s message. It’s a big part of Adams’s message. But some of the candidates are calling for significant reductions in the police budget, like Stringer and Wiley.

DS: Anything stand out to you on understanding the budget and the city finances?

HW: Obviously Scott Stringer understands the budget pretty well. I mean, he’s the comptroller. I was very impressed with Kathryn Garcia’s knowledge of New York City government and its operations. She is somebody who could teach a class on how government actually operates.

DS: You gave them open-ended questions, and infrastructure and transportation didn’t seem to come up all that much. I don’t recall anyone talking much about potholes. Did that surprise you?

HW: I’m very interested in transportation policy. I was very much involved with expanding bike lanes during our third term and the rollout of Citi Bike. When I look back on the interviews, I wish I had asked more about that. A lot of the candidates have got some pretty bold ideas around expanding access to safe streets and making the city more livable, more pedestrian-friendly, more bike-friendly. We’ve made an enormous amount of progress in the city politically around this. The expansion of bike lanes and bikes was itself fairly controversial during Mike Bloomberg’s third term, and now seems really rather cemented and broadly popular if you judge by the candidates.

DS: In terms of having a policy-based vision for the future — that is, keeping people here, attracting new ones, seeing to it that the city is on the edge of technology and information, connecting all of the above — is there anyone whose policies have a sense of what the future of New York would look like?

HW: Andrew Yang definitely talks about that. And he’s the candidate who seems most actively campaigning at sporting events or theaters or restaurants. And the message that he said he was trying to send is that New York is open for business, and that is an important part of being mayor, being the cheerleader for the city. And I do think that Yang is more aggressively owning that message than some of the others.

DS: As part of this project, you interviewed Thomas Dyja, who’s just written a history of New York City, and he talked about reaction and counter-reaction. Mayors tend to emerge in opposition to their predecessors — Koch begat Dinkins, who begat Giuliani, and so on. What governing and leadership style is the city looking for now, and what temperament, and is it in reaction to de Blasio, or has Covid skewed the dynamics?

HW: Dyja suggests that the city goes through cycles where it wants more order and then cycles where it is more tolerant of disorder. His book only goes back to Koch, but if you think about the arc of New York history since World War II, kind of ’45 to ’65, this period of order, which in fairness, it’s a period of a lot of conformity and order around the country. And then from, broadly speaking, ’65 to ’93, you’ve got a much greater tolerance of disorder, which certainly through the ’60s and the ’70s, I think coincides with a loosening of strictures around the country. And then from ’93 to ’13, you have more of a return to order. It’s probably too soon to tell, but we seem to be in something of a period of a return to disorder.

DS: Does a period of disorder lead you to think that the city will be looking for a mayor who will restore order?

HW: None of them are really arguing for a return to order. Some of them are more orderly than others, but I think we are in another period of disorder.

DS: To this point, the campaign has been conducted largely over Zoom, and that’s changing with vaccinations and better weather, but how would you characterize the Zoom portion of the campaign and what dynamics do you think it’s created?

HW: If you’re a citizen who’s interested in learning about the candidates, there’s now so much information archived on YouTube from these Zoom forums that you can really educate yourself rather comprehensively and rather quickly. And that’s terrific, right? What’s missing is the traditional New York street campaigning. I remember in 2005, when Anthony Wiener was running for mayor the first time, my wife and I saw him on three separate occasions campaigning in person that summer, and New York City’s a big city.

This is a city of people who I think correctly see themselves as hardworking people. People come here to make something of themselves. This can be a pretty demanding place, and if you’re not prepared to work hard, it can be difficult. When New Yorkers look at themselves in the mirror, they see a city of hustling, striving people. And we want to see our candidates for mayor working hard, getting out there, asking us for our vote, pushing themselves.

DS: The race has been pretty static — Andrew Yang leading, followed by Eric Adams, and then Scott Stringer and Maya Wiley coming up next. So how durable is the lead and this ordering?

HW: Yang’s lead has been fairly consistent over many polls. But the advertising phase of the campaign has not begun. Effective advertising impacts voter decision-making; it doesn’t guarantee an outcome. You gotta have the right message articulated by the right candidate.

DS: I have to imagine name recognition is a factor with Yang, but there must be something else that has kept him in the lead.

HW: The fact that Andrew Yang gained a certain amount of celebrity running for president has certainly helped him so far in this mayoral race. But to your point, it’s not just celebrity. He has carved out a lane that is optimistic, hopeful, future-oriented, a bit more moderate than some of the others.

John Mollenkopf, who is a political science professor here in the city, offered up a somewhat more skeptical take on Yang around the idea that what matters in electing mayors in New York is grassroots and organizations, labor, neighborhood strength. The question is, in 2021, is that still true?

Again, Yang is in the mid-20s. I’d rather be him than one of the other candidates now, based on the polls, but his lead at this moment is actually fairly modest.

DS: So ranked-choice voting, which we have for the first time, means the race is pretty fluid?

HW: I don’t think it’s about ranked choice. There is every opportunity for one of the other candidates to grab the bull by the horns, to identify the mood of the city, to marry that with their biography and to advertise it effectively and become mayor.

DS: In that calculation, do you think experience with city government will matter?

HW: Yes, I do. I think one of the reasons Yang is at 25 and not 35 is that there may be some reservations about somebody who doesn’t seem to have voted very often in New York City and doesn’t have any experience in New York City government.

DS: You asked all the candidates for their second choice and only two, I think, answered you. Shaun Donovan said he’d vote for Maya Wiley, and Andrew Yang said he’d vote for Kathryn Garcia. What does this tell you?

HW: That there’s a political advantage for a male candidate to associate himself with a female candidate. And in the case of Yang, the opportunity to associate himself with the candidate who has the most governmental experience.

DS: How has ranked choice shaped the dynamics of the race?

HW: The biggest difference is that if the race ended today and we were under the old system, chances are, nobody would get to 40% and there would be a runoff, two candidates going at each other day after day. And frequently you get a lot of comparative or negative advertising in that context. It’s not clear to me that anybody’s gonna air a negative ad in this race because in the ranked-choice format, it’s not nearly as obvious that it makes sense to do that.

DS: So a good thing — not being subjected to a hailstorm of negative advertising.

HW: Negative advertising that is untrue or unfair is distasteful. But in a race this important, the candidates have differences, and sometimes it’s important to talk about those differences. I think that you’ll see it at a debate, but I’m not sure that you’ll see it on television.

DS: One of the things that’s been striking is that there’s been no real breakthrough moment, where a candidate really found a way to distinguish himself or herself from the pack. If that drawing of distinctions is minimized in this process, what odds do you give as a strategist for a breakthrough moment actually taking place?

HW: Oh, I think there’re opportunities. If I were advising one of the candidates not named Yang, I would say, “Don’t worry so much about Andrew Yang. Worry about your own message and putting forth your own agenda for the city. There’s every opportunity to make your case. And if it catches on, people will respond to it.” If Andrew Yang wins and becomes mayor, it will be in part because none of the other candidates was able to catch on.

DS: Do endorsements matter?

HW: It depends on the endorsement, but sure. The New York Times endorsement will matter. AOC’s endorsement would matter if she endorsed.

DS: How much is money gonna matter? Has public financing minimized it? The Campaign Finance Board has awarded $20 million, $22 million in public financing so far, and some candidates are self-funding.

HW: My guess is the candidates will have enough money to get their message out. You know, nobody’s going to be able to overwhelm the field with money. If that were the case, it would already be happening.

DS: Why has New York never elected a woman mayor?

HW: That’s a very good question. You know, when I worked for Hillary Clinton, we used to talk about this because New York had not at that point elected any woman to statewide office, either. And one of the theories was that the tabloid culture in New York City that promotes and rewards a certain kind of pugilistic sensibility doesn’t always reward women for being pugilistic. And I think there’s some truth to that. There are, I’m sure, a host of factors, but I think there’s some truth to that.

DS: If you follow the logic here and ranked choice creates an environment where potentially you’re drawing fewer distinctions, or there is a minimization of the pugilistic side of things, does that lead you to conclude that there are new opportunities for women candidates?

HW: Yeah, in theory. I asked Maya Wiley about this, and she did talk about the opportunities created by public financing for women. And Dianne Morales was very eloquent about a moment where you look in the mirror and you say, “Well, why not me? Why not someone like me?” And I do think public financing does provide an avenue and a vehicle for candidates in a way that did not exist previously.

DS: What should we be looking for in the coming months?

HW: New Yorkers will see a lot of advertising and that will reflect the essence of the candidates’ message in a distilled format. The debates will be important. I would encourage people to watch the debates. There are three, and I think they will be lively. A lot of our readers will be interested in the Times endorsement. The candidates will be campaigning more in person, they’ll be out and about. And that will be interesting to watch.

DS: You’ve been asking the candidates lots of questions. What should we be asking them?

HW: The city is facing some profound challenges. You have a central business district that is essentially a ghost town. You have people who have moved away during Covid. You have a tourism industry that is vital to the city’s future that has been decimated, and you have a profound set of racial and economic inequities that are crisis-like in some measure. And the next mayor will not inherit the relative peace and prosperity that Bill de Blasio inherited from Mike Bloomberg. These challenges will be on that person’s doorstep on Day One. We all want to ask tough questions about who has a vision for both restoring the aspects of the city that worked well prior to Covid and also fixing those things that were broken before Covid, and who do we think has the vision, management chops and overall ability to do those things.

DS: One group you did not ask questions of: Republicans. Doesn’t that say a lot about the state of the GOP locally?

HW: I think that given the Republican field and given the moment, the chances of a Republican being elected mayor are pretty minimal.

DS: So then the winner of the Democratic primary, whoever that is, is likely to be the next mayor of New York City.

HW: Without a doubt.

DS: What would you suggest that person do between June and the general election?

HW: Well, it’s going to be the longest lame-duck period that we’ve ever really had. Usually we have a September primary, not a June primary. As Mike Bloomberg would say, you’ve got to attract talent, you’ve got to build your team and go out and get the very best people to become deputy mayors and commissioners. Hopefully whoever is the next mayor-presumptive goes out and tries to hire really terrific people, regardless of whether they voted for them, regardless of party ideology.

DS: Can you imagine a different sort of transition even before the general?

HW: I think that lame-duck period over many months is going to be awkward because whoever is going to be the next mayor will have been at least something of a critic of Bill de Blasio. It’s not like he’s being succeeded by his loyal vice president. And I think it will be awkward.

DS: Putting you on the spot — any favorites?

HW: There are things about all of them, frankly, that I liked. I’m still undecided and I’m still waiting to see how it plays out.

This column does not necessarily reflect the opinion of the editorial board or Bloomberg LP and its owners.

David Shipley is senior executive editor of Bloomberg Opinion. He was deputy editorial page editor and op-ed page editor of the New York Times, and served in the Clinton administration as special assistant to the president and senior presidential speechwriter. Shipley is co-author of “Send,” a guide to email.

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