Q&A: Dan Doctoroff on 'Greater Than Ever' and the rebuilding of NYC

The former deputy mayor on the city's past, present, and future

"Doing anything in an urban environment is hard."

Former deputy mayor Daniel L. Doctoroff says this near the end of a chat with Curbed about his new book, Greater Than Ever (Hachette, out now), and it's a tidy encapsulation of what, exactly, that book is all about. It's partly a look back at his tenure during the Bloomberg administration, but also what he calls a "memoir-manifesto" about how to promote growth in cities—and the often rocky path it takes to get there.

Doctoroff served as the deputy mayor for economic development for seven years under former Mayor Michael Bloomberg, beginning his tenure just two months after the September 11 attacks devastated lower Manhattan. That catastrophic event was the catalyst behind some of the Bloomberg administration's defining initiatives—the rebuilding of the World Trade Center, for example—and in his position, Doctoroff had a front-row seat for what happened. He also worked on successful ventures outside of downtown (the development of Hudson Yards, rezoning of many NYC neighborhoods) as well as less-successful ones (the bid for the 2012 Olympics).

Doctoroff details all of this with refreshing candor—there are insights about his former boss, as well as choice words reserved for Donald Trump and Sheldon Silver—and more than a little bit of wonky, policy-oriented details. The resulting book is a fascinating peek at a critical moment in New York's history.

Doctoroff spoke with Curbed by phone from his office at Hudson Yards, where his start-up Sidewalk Labs is located, about the book and why cities must always be looking forward. You can also hear him discuss those topics tonight at the 92nd Street Y.

Curbed: Why did you feel that now was the right time to look back on your years in the Bloomberg administration?

Dan Doctoroff: It's been almost 10 years since I left City Hall. One of the lessons about the book is that a lot of these plans require a very long-term perspective. Think about Hudson Yards as an example, where I'm sitting now. I first came up with the idea of Hudson Yards as part of the Olympic bid in 1996. Here it is, 21 years later, and it's really coming to fruition. There's a good moment where the memories of what happened are still fresh, but enough has occurred that we can validate where things went right, and in some cases, where they didn't go as well.

It's interesting because Greater Than Ever is sort of a memoir, but it's also wonky policy details, and almost a manifesto about how to run a city. What was the process of writing it like?

DD: It evolved a lot. I really wanted to explain how we engineered the comeback of New York. I thought that my journey was important, in part because the Olympic bid was so fundamental to the story. Much of what we developed as part of the Olympic bid found its way into plans that we ended up pursuing and executing. That was a very personal thing for me, and it's the source of a lot of the highs and lows.

But then in terms of city history and some of the policy stuff, I couldn't actually explain what we did without going into descriptions of what the policy means, and what and how and why we thought about it. Overlaying all of this was a belief in cities, and how we think about cities, and what's good for cities.

You start the book with an anecdote about how you hated New York City when you were a kid and never anticipated moving here. Do you think that gave you a different viewpoint of the city than someone who may have always had this romantic, starry-eyed notion of NYC?

DD: By the time I started getting involved in New York, I did have a romantic notion of the city. The whole idea of the Olympic bid that I developed sitting in the stands at that stadium was founded on a romantic notion of New York.

I think what I did have—and this was also the result of the Olympic bid—is that I did see the city through the eyes of outsiders, or maybe even our competitors. I had a somewhat more objective view as a result of that competition. The second thing I had, which I think was a benefit, is naiveté. That's a plus and a minus. When we came into office, everybody said how hard it was to get everything done. I didn't know enough to know that that really wasn't true. I also was hurt by it—I had no idea how to deal with the legislature in Albany, which I still think is a complete hall of mirrors.

As you were reflecting on that period and all of the projects that the Bloomberg administration undertook, what stood out to you as the most difficult time?

DD: Personally, the defeat of the [West Side] stadium. I do point out in the book that while I am convinced that pursuing it there was the right thing because of the catalytic impact it had on the development of Hudson Yards, I think it's fair to question whether the use of that for those blocks for a stadium was the right thing.

I think what it also points out is sometimes out of great tragedy—at least from my perspective at the moment—comes incredible opportunity. Six days later, we had signed agreements for two stadiums [Citi Field and Yankee Stadium], and the Olympic bid was able to continue. Of course, a month later, then we lost again. That period in 2005 was just a remarkable roller coaster.

Photo by John Moore/Getty Images

"The High Line is an example of something nobody dreams would have the impact that it did."

What about successes? Is there anything you worked on that, looking back, you feel was successful beyond what you had even imagined?

DD: The High Line is an example of something nobody dreams would have the impact that it did, and the impact both in terms of creating just a remarkable public space, but also the impact on surrounding community.

To be honest, I think the vast majority of things have turned out much better than we actually expected. I'm really proud of what happened in Lower Manhattan, and on the World Trade Center site specifically. The number of residents there has tripled, the retail and the street improvements, the number of parks, and the infrastructure that's been created there has created a truly unique community. [And] everything in Brooklyn, that's worked out in ways way beyond our expectations, including the parks and things like that.

Where I think there's some disappointment is that we didn't calibrate as effectively as we could the impact of everything we did, and the city grew a lot faster. A negative consequence was it got more expensive more quickly. In retrospect, we probably didn't do enough. I'm not sure what I would have done differently at the moment, because the city just took off in a way we didn't expect.

It is a common criticism of the Bloomberg administration—that the success of initiatives like the High Line or Hudson Yards have come at the expense of affordability.

DD: I think the recovery occurred so quickly, and the success of so many of these things became apparent, that it was hard to anticipate. Remember, we started with a $3.5 billion housing plan with 65,000 units in 2002. Then, as we saw the city recovering, we more than doubled down in 2006, and increased it to $7.5 billion and 165,000 units. We did respond, as we saw it, and then it just continued to take off. I think it is hard to get it exactly right.

I look back on other things I'm really proud of. I think PlaNYC was pretty revolutionary. It really encompassed every aspect of the physical environment. I think it changed the whole conversation about sustainability in the city on many different dimensions, and in fact had that impact because it was used as a model around the world.

On the other hand, one of the initiatives that didn't happen was congestion pricing. It finally went down to defeat after I left. It is ironic that as this book's coming out, there's been a serious discussion about congestion pricing. I think it's inevitable that it's gotta come back, because we just need the sources of revenue in order to pay for the improvement of the transit system.

Do you feel somewhat vindicated about that?

DD: Look, that may have been a failure on our part to effectively sell the seriousness of the problem. We obviously didn't do a good enough job of selling that, and we tried really hard. Sometimes you are just ahead of your time, sometimes it's your own fault. In that case, maybe it was a combination of the two.

Do you intend for the book to be seen as a blueprint for what cities can do in order to boost economic development, or implement big ideas in their own cities?

DD: I hope so. Obviously, our situation is unique. I try to infuse some of that stuff into the body of it, but really, it's in the epilogue, where I talk about the four elements that I think enabled us to get things done: the catalyst, a philosophy, a plan, and execution, basically.

We had 9/11 as a catalyst. With PlaNYC, there was no real catalyst—the catalyst was a group of city officials who said, "Hey, you know what? We believe that growth is good. We foresee significant growth. We know that the thing that's gonna limit our capacity to grow is our inability to accommodate all these additional people. We better deal with it."

I give Mike Bloomberg incredible credit for being the one who encouraged us to think that way. But leadership is actually identifying problems before they're obvious, posing creative solutions to them, figuring out how to execute on them, especially when nobody is calling for it.

In terms of big civic projects that are currently in the works, what's something you're excited to see come to fruition?

DD: I think the rezoning of Midtown East is really important. As Midtown becomes mustier, if you will, it has to change, so I think that is going to be really important to continuing to modernize the city's office space. The plans for affordable housing—we believe very strongly in mixed-income neighborhoods, and our commitments to help people who couldn't otherwise afford to be able to live in places, to be able to afford it. The De Blasio administration has stepped that up somewhat.

I think there's a potential set of infrastructure projects that are on the table that in some ways connect a lot of the things that we did that are really interesting. The BQX that runs down the Queens/Brooklyn waterfront—connecting all these new neighborhoods is really important. There's a discussion about gondolas, which I was an advocate of early on, connecting downtown Brooklyn or the Brooklyn piers, and Governors Island in Lower Manhattan. Unlocking the value of Governors Island is really an interesting project.

Just listing those different initiatives, it's kind of remarkable realizing how much the city has changed even in the years since you left the Bloomberg administration, for example.

DD: That's the beauty of the city. The danger is that we become complacent, or that we simply fail to recognize that the world is changing, and that we have to change with it. The competitive environment for cities change, the needs of cities change, the needs of citizens for their cities change, the need to grow is perpetual. If you don't think about this stuff, you're going to stifle your growth, and you're gonna set the city back into reverse. That's what you can never let happen.

A great quote about the city is—I forget who it was, but—"It'll be a great place if they ever finish it." [ed. note: It's an O. Henry quote.] Of course, that's exactly not the point. The point is, it can never be finished, because the world changes.

You have to give people the tools to capitalize on the opportunity that the city uniquely creates.

What do you think is the biggest challenge that New York City is facing currently?

DD: Unquestionably, it is affordability. Some of that is part of an international trend—middle-income jobs, particularly ones that do not require extensive education, are disappearing as a result of technology. I think that is the fundamental thing that we have to wrestle with.

The only way to deal with it at the end of the day is to generate money to invest back into the city, to improve social services, to improve transportation, to ultimately give people greater access to opportunity. You have to give people the tools to capitalize on the opportunity that the city uniquely creates.

How has your experience influenced what you're doing now with Sidewalk Labs?

DD: It's a combination of my last two careers. Helping to run New York City, and then running Bloomberg, which is still, I think, the largest technology company in New York. What we're trying to do at Sidewalk Labs is really attempting to bridge the divide between urbanists and technologists. If we don't do that, then the implementation of technology to help dramatically increase quality of life in cities will just take a lot longer, and the potential will not be fulfilled.

Is there one galvanizing issue you think those two groups can come together behind?

DD: The most complicated one is around mobility, generally. We're not gonna be creating lots of new roads, we're not gonna be creating many new subways … but either at the federal level, or at the city and state level, we're going to have to figure out ways to use what we've got. The only way to do that is with technology.

The good news is, through shared vehicles and self-driving vehicles, the capacity to do that and dramatically lower costs is going to be real. Ushering that in is going require not just technology, but a new set of rules and approaches from a regulatory perspective and from a business model perspective.

But if you can begin to solve the transportation problem, a lot of other pieces begin to fall into place. Not to say that's the only thing, but it really lies at the core of addressing many of the urban problems.

What would you say the defining accomplishment of the Bloomberg years is?

DD: Well, I know what Mike Bloomberg would say—and I can't claim any real credit for it—which is increasing the average life expectancy of a New Yorker by three years during his tenure. From my perspective, the fact that over the course of the Bloomberg administration, the population actually grew the way it did.

Hopefully, what comes through here [in Greater Than Ever] that it was the product of a remarkable group of people coming together at a critical moment in the city's history, and finding ways to work together that were uncommon in government, to do, in many cases, historic things.

This interview has been condensed and edited.