Howard Wolfson was formerly a longtime Democratic communications strategist who has been described as the “chief architect” of Hillary Clinton’s 2008 presidential campaign. (After Clinton conceded to Barack Obama, Wolfson briefly published a blog on this website called “The Flack.”) But he went to work for Mayor Michael Bloomberg’s second re-election bid, and for the past three-and-a-half years, he has served as New York’s deputy mayor for government affairs and communications.

Wolfson has recently been in the news for criticizing public advocate and Democratic mayoral candidate Bill de Blasio. Earlier this week, Wolfson accused him of wanting to return the city to a time of “higher taxes … more regulation on business … more permissive policing” and for allegedly flip-flopping on whether New York officials should be subject to term limits.

I spoke to Wolfson last Friday afternoon in a small room off the main bullpen at City Hall. I apologized for being sweaty, explaining I had used a CitiBike—the bike-sharing program Bloomberg championed—to come downtown. He scolded me for apparently not wearing a helmet.1 I motioned to my backpack, in which I had put mine.

Marc Tracy: I was biking on the Brooklyn Bridge on the way home one night, and as I passed someone, she started shouting—she was on her own bike—“You’re on a clunker, it’s just a billboard for the bank!” How should I have responded?

Howard Wolfson: I guess what I would’ve said is—“How could you be against something that encourages people who’ve never biked to get on a bike? And has provided a real transportation alternative to cars and other forms of motor vehicles?”

MT: I feel like there’s two types of people. There’s types like me—I didn’t engage partly because I was biking uphill, but also I generally don’t engage like that. And there’s another type, who is eager to engage.

HW: I would’ve engaged.

MT: So you’re that type.

HW: I’m definitely that type.

MT: Since taking on this role, have you seen your portfolio expand—both within the administration and from what you were doing with, say, Hillary Clinton’s campaign?

HW: There is a heavy policy aspect to the job. There is certainly a heavy communications aspect, but much of what I spent might day on today was facilitating a parade.

MT: Today there was an op-ed by the mayor about Big Tobacco [criticizing the Obama administration]. Do you think the mayor still regrets not running for president in 2008?

HW: Not that he’s told me.

MT: Does the mayor plan to continue to target legislators, including some Democrats, over guns?

HW: Yes.

MT: Why?

HW: Because for too long our side has basically given members of Congress a free pass. There has not been any electoral or political price for voting against common-sense gun laws. The [National Rifle Association] takes a long view—to their credit. And we’ve got to take the long view. If there are members who vote the wrong way, we need to make sure they understand that people are going to hold them accountable. That applies to Democrats and Republicans.

MT: Have you spoken to your old boss Senator Schumer [the third-ranking Senate Democrat] about this?

HW: I have. He has a different point of view.

MT: And do you exchange those different points of views amicably and go your separate ways?

HW: Absolutely. I have enormous respect for Chuck. He’s incredibly smart and very invested in this issue. He’s also invested in a Democratic majority. We’re not as invested in a Democratic majority.

MT: He would argue the two issues dovetail.

HW: Well, except for the fact that the Senate couldn’t pass this bill.

MT: Two years ago, The New York Times reported that Bloomberg privately told everyone that he hopes Quinn succeeds him. Do you think that was true then?

HW: I think if we have news to make on the mayor’s race, we will make it not in the context of this interview.

MT: I think it’s fair to ask you about this quote, though, because it’s something you’ve already said. You said: “He has a very 1960s, 1970s view of the city—”

HW: Yes! My friend Bill de Blasio.

MT: “If you prefer the version of the city that existed then, he’s your guy.”

HW: I was literally just on the phone with him when you walked in, dealing with the Pakistani Day Parade. Bill and I have known each other for a very long time. We were colleagues on the Clinton campaign of 1999–2000. I spent an enormous amount of time with him, got to know him well, got to know his family. I like him very much. I contributed to his campaigns in the past.

MT: Have you contributed this year?

HW: No. [laughs] When I took this job, he and I used to have lunch maybe once a month, just to catch up on stuff. So I like him. I have real and genuine affection for him. I think he has the wrong view of what is right for this city: I think higher taxes and more regulation and more permissive policing is not the right approach. That was the policy New York City employed in the ’60s and ’70s. They’ve tried that in other cities, and it has not worked there, and it would be a mistake to do it here. That’s an argument on the substance.

MT: Let’s say [de Blasio] is elected mayor, and he is successful in implementing his agenda. Do you think New York will revert back to the ’60s and ’70s?

HW: I don’t think the subways become graffitied overnight.

MT: But over four years?

HW: No city, no brand, no company, no individual can live off the value of legacy. You have to constantly keep moving forward, constantly keep innovating, constantly working, constantly improving. We are competing with every other major city in the world for talent, for capital, for resources. So yes, I think New York’s future is not inevitable, progress is not guaranteed. And I worry that an approach that argues for, as I said, higher taxes and more regulations will be bad for New York.

MT: De Blasio wants to raise taxes on those making more than half a million dollars to pay for pre-K and after-school. Tell me exactly what’s wrong with that.

HW: We’re already the highest-taxed jurisdiction at the high end in the country.2 People who live here are already making a decision that says, “It’s more expensive for me to live here then anywhere else, and I’m willing to pay that price.” What changes that? You can raise the price, and people could decide it’s not worth it anymore. Or it could be because crime goes up or it becomes dirtier. Or both of those things could happen. A combination of things could really have an impact.

MT: You say people might leave. And you imply that you would rather have those less-affluent people leave than have the people making more than $500,000 leave. Why?

HW: In a pure economic sense, one person who pays an enormous amount of money in taxes is worth more to the city than someone who doesn’t. A very small number of people in the city pay a very large portion of our taxes. That’s all redistributionist. And that’s fine! God bless. That’s America. But you only need a very small number of those people to leave before you have a revenue problem.

MT: So you’re saying that the economic imperative trumps all the others? We could all adopt a sort of libertarian, anarchic …

HW: Well Mike Bloomberg is very far from that.

MT: I think we know that. But on economic issues …

HW: Here’s the thing. We can all whistle “The Internationale.” But this is the most redistributionist place in the country.

MT: But it’s also the most unequal place in the country, and when you extrapolate to the five boroughs, it’s the most unequal big city. And that’s fine, there’s reasons for that.

HW: I was gonna say, Detroit is very equal.

MT: I get that. But given that, why isn’t it okay to make a little correction?

HW: I guess I’m more concerned about mobility than inequality. I’m more concerned about poverty than inequality. To me, inequality is a political argument, and from an economic or policy perspective, we ought to be talking about mobility. I would rather have a conversation about how we reduce poverty and increase mobility than how we redistribute wealth.

MT: Why go negative or even take a position on any mayoral candidate—much less in the primary, much less in the primary of the party the mayor does not belong to?

HW: Part of my job is to defend this mayor’s record and legacy. And if there are candidates who are attacking his record, his legacy—I’m not going to respond on a daily basis, but I have an obligation to respond. I wrote an op-ed about Bill Thompson. I’m going to do that from time to time.

MT: Do you consider yourself a Democrat?

HW: Yes, I am a Democrat. I am a registered Democrat—I will be voting in the Democratic primary.

MT: Let’s say, for the sake of argument, it is Bill de Blasio versus [Republican] Joe Lhota in the general election. What do you do?

HW: I don’t know. I’d have to think long and hard about that. I suspect I wouldn’t be the only one.

MT: There have been concerns about the voting-machine situation. [New York is prone to long counts and old machines; if there is a close run-off in the primary, the Democratic nominee may be unclear until just a couple weeks before the general election.]

HW: The Board of Elections is not under our purview, unfortunately.

MT: Do you wish it were?

HW: If I could wave a wand putting it under the mayor or the governor? Yeah. I think accountability is a good thing.

MT: Same principle as the Board of Ed? [Which Bloomberg essentially took over.]

HW: Yes.

MT: You mentioned that you used to have lunch with de Blasio about once a month. When did the lunches stop?

HW: Probably earlier this year, when it became increasingly clear that he was going to be basically running against us. There was not as much to talk about at that point!

MT: What do you anticipate doing after 2013?

HW: I don’t know.

MTWhat do you anticipate the mayor doing?

HW: He’s certainly going to be involved with his philanthropy. He’s going to remain involved in issues like guns and immigration and choice. How he spends the rest of his time, I think he’s still thinking about it.

MT: Do you hope Hillary Clinton runs?

HW: I do. I think she’d be a great president.

MT: Would you want to work for her?

HW: I think one presidential campaign is enough. They basically rob you of your life.

MT: To seek your advice as “The Flack”: There are about three different potential fiscal crises coming up in D.C. You are a relatively disinterested expert in communications. I’ll note that you did air-quotes when I said “expert.” How do you think Obama is doing?

HW: I haven’t really been paying much attention. One of the nice things about living in New York is you can spend a lot of your time focused on New York. The daily back-and-forth in D.C., I don’t spend a lot of time on it.

MT: Congratulations on the soccer team. [In May New York City landed a second Major League Soccer team, to be co-owned by the New York Yankees and Manchester City Football Club.] Why did you think it should go in the park in Queens?

HW: That was what we came up with as the best site—certainly there are other possibilities. I hope we can get a site somewhere in the five boroughs before we leave.

MT: Who should fund the stadium?

HW: Private enterprise.

MT: Will this be your favorite MLS team?

HW: Undoubtedly.

MT: I know you’re a soccer fan.

HW: I am. This is now taking us far afield.3 I am so anguished over the possibility of Tottenham selling Gareth Bale. I don’t understand how such a thing could be possible. Being able to watch him on television playing in the [English Premier League] is such a source of joy. Going to White Hart Lane and watching him in person is sublime. And the fact that a team in London that is this close to the top four would sell their best player, one of the best players in the league—I’m just mystified by this. I’m so upset about it. I don’t understand how NBC doesn’t put their foot down and say, “We just spent a billion dollars on rights to your league. How could you sell your best player to another league?”

MT: Usually I believe the leagues dictate to the networks rather than vice-versa.

HW: If I paid a lot of money for a product and one of the best parts of the product disappeared, I might be a little upset.

Marc Tracy is a staff writer for The New Republic. Follow @marcatracy.

This interview has been edited and condensed.

  1. Although Bloomberg opposes a helmet law.

  2. For those above $150,000, it’s actually Bridgeport, Connecticut; Philadelphia; and then New York.

  3. I believe the pun was unintended.