Mayor Enters New Urbanist Lion’s Den

It fills in a failed urban renewal highway. Does that make it “new urbanism”?

That question has hovered above New Haven’s biggest development project in a generation, Downtown Crossing. Another way of asking the question: Is New Haven undoing a major mistake and learning from its past? Or is it repeating the mistake?

Mayor John DeStefano traveled to West Palm Beach, Florida, to try convince his toughest skeptics that New Haven has learned, that New Haven is rebuilding community and neighborhood and a lively streetscape where bulldozers once killed them. He spoke by invitation on a panel at a conference organized by a group called the Congress For The New Urbanism.

He earned points from the skeptics for showing up and making his case. He didn’t win many converts.

“With all due respect Mr. Mayor,” asked one participant, a designer from California, “what the fuck were you thinking?”

Here’s what DeStefano was and is thinking, he told the group: “Don’t let the perfect be the enemy of the good.”

The “good” he referred to was Downtown Crossing, phase one of which is before the Board of Aldermen for approval.

Under the plan, DeStefano is hoping to fill in the Route 34 Connector mini-highway-to-nowhere that slashed through downtown a half-century ago during the height of urban renewal. The dream then was to connect commuters from I-95 to the Naugatuck Valley. It was called the “Oak Street Connector” though it was more like an Oak Street Eviscerator. And it was never finished. In the end, it just went three blocks—but helped destroy a neighborhood and separate downtown from the Hill.

The city hopes to begin its rebuilding effort by filling in the block nearest to the Air Rights Garage and having developer Carter Winstanley build a 10-story biomedical office building. That phase should cost $140 million, including Winstanley’s building and government-backed road changes.

At first blush, the enterprise seems to typify the “New Urbanist” creed. That philosophy calls for reversing the strategy of mid-20th century urban renewal (of which new Haven is the most concentrated example). Instead of large single-use modern buildings and highways and car-centric street grids, New Urbanism combines stores, apartments, green spaces, offices, all together on a human scale with a walkable and bikeable streetscape and narrow, slow-moving two-way roads. Downtown Crossing was originally sold as a way to stitch back together the Hill and downtown, with an emphasis on pedestrians and active street life.

By the time it came up for approvals, it featured the 10-story office building (pictured) with five lanes of one-way traffic and no new cross streets. Critics saw a new highway replacing an old highway, with endless cars and a corporate island keeping neighborhoods apart and people away. Officials estimate Downtown Crossing will bring the city hundreds of new jobs and more than $1 million in new annual tax revenue.

Click here and here and here to read some previous stories outlining that criticism. And click here to read a critical analysis released by New Haven’s Urban Design League.

That criticism spread from New Haven to the Congress for a New Urbanism, a national group. The group invited DeStefano down to an annual conference in Florida last week—and he accepted.

He knew to expect criticism. He hadn’t realized he would walk into a lion’s den.

He was one of four scheduled panelists to address a 2 p.m. breakout session called “Urban Freeways: Devastation and Opportunity.” New Haven was one of several examples of cities tackling “urban freeways [that] destroyed traditional, often poor, neighborhoods” and exploring how “to repair the urban fabric and make cities whole again.”

The mayor brought along a 19-slide PowerPoint presentation entitled “A Dream Comes True!” It began with the picture at the top of this article. Then-Mayor Dick Lee, the father of New Haven’s nationally watched urban renewal, distributed it as part of a 1959 campaign brochure to argue that he was remaking the city in a smart way to create jobs.

On the subject of the highway, DeStefano agrees with the new urbanists: It was a mistake.

“They thought the highway was the dream,” DeStefano said of the Lee administration planners in a subsequent conversation about his Friday presentation. They had rundown homes torn down all over town to make way for progress—including a home on East Street where the DeStefano family lived.

“Highways were used as slum clearance. We didn’t know we lived in a slum. We didn’t live in a slum. It was a three-family house with a lot of people,” DeStefano said.

He noted that the circled numbers in the flyer pointed to new buildings where new jobs beckoned: the George Street phone company headquarters, the College Plaza, the former Channel 8 retail plaza. The mayor made two observations about that. One: The planners saw transportation policy as a way to make way for new jobs. And two: All those locations have now morphed into medical-related labs and offices or Yale-owned space. “Eds and meds”—education and medical-related development, the current engine of New Haven’s job-creation strategy.

In other words, times change. And New Haven is rebuilding that area with new jobs in mind. We can learn from the past and still aim high the way the city did then.

“They were very smart and very competent and did a lot of great things. Dick [Lee] said, ‘Our goals were great, so too were our failures,” DeStefano said.

DeStefano also offered a slide (pictured) of how the city envisions the larger area developing over time as the highway fills in.

Other members of DeStefano’s panel discussed Boston’s Big Dig and Miami’s Overtown Expressway. When it came time for audience questions, almost all the attention turned to DeStefano and New Haven’s Downtown Crossing.

The participant asking the expletive-enhanced question quoted higher up in this story was R. John Anderson, founder of a Chico, California, architecture and design firm and a prominent New Urbanism proponent.

“We should not let the lame be the enemy of the perfectly adequate,” Anderson told DeStefano, according to notes taken by another New Havener present, Philip Langdon.

DeStefano’s reply: “You have no money on the table.” In other words: That’s nice in theory, but the city has to deal with practical realities like investment and revenue and the existing streetscape.

In his presentation, the mayor emphasized that the city has other priorities beyond design, such as school reform, job-creation and public safety. He also noted that his administration obtained 121 variances from Connecticut’s transportation department in the design to accommodate design concerns, including reducing travel lanes to 10 feet wide.

New Haven’s Langdon said he came away with the conclusion that the Dick Lee campaign brochure was an unintentionally apt choice for the mayor’s presentation: “The mayor is more in the Dick Lee tradition than he realizes.”

Anderson said Monday that he didn’t find the mayor’s response—that the city put together an important job-creation project that is worth pursuing even if it’s not perfect—convincing. He called Downtown Crossing as currently designed an “epic mistake.”

“I did tell the mayor that I believe he is making a huge mistake in making a lame project the enemy of a perfectly good project. By not reconnecting the street grid and leaving the grade separation, he is wasting the potential for future private investment in a high value area that can reconnect the medical district with downtown and the surrounding neighborhood,” Anderson wrote in an email message.

“The tone of the mayor’s remarks was that he had done all that could be done and the grown-ups had decided that half a loaf was better than none. The plan that mayor is pushing is breathtakingly stupid because it does not deliver even half a loaf. ... I regret that I could not be more polite in my remarks following the mayor’s presentation, but we were all watching him blithely wander off into oncoming traffic. I hope that he will not continue on his current course.”

Norman Garrick, a UConn professor, praised DeStefano for showing up.

“I was real impressed that he did come. People had a different perspective of what we need to do,” Garrick said in a conversation Monday. “He got almost all the questions. It was people trying to get across a different design.”

Garrick’s takeaway from the event: “It doesn’t seem from their [the city’s] plan that they’re [really] losing the highway.

“What they’re building including the Winstanley building seems like a continuation of the suburbanization ... It’s a big box. It’s a lot of cars. It’s not integrated with the neighborhood.”

DeStefano’s takeaway from the event: The designers in the audience don’t operate in the real world.

“We are removing a six-lane limited express highway. And their arguments had to do with number of turn lanes and lane width. It is fundamentally different than what is there now. To me the idea that somehow this is not an incredible departure is removed from any meaningful sense of reality,” DeStefano said Monday. “They just ignore any real discussion of budget constraints, any real grounding.”

For instance, DeStefano said, participants argued that the loading docks for the Smilow Cancer Hospital and other nearby facilities should return to street grade. (The city moved them to below the Air Rights Garage.) He said that would create a broad range of new traffic and safety problems. Similarly, he said, participants pointed to the three lanes of traffic coming off I-91 at Trumbull Street as an example of how Frontage Road could work coming off the highway. “We have ten times as much traffic” there than at Trumbull Street, he said.

“I don’t have a green field [to build on from scratch],” DeStefano said. “I have an imperfect world that I’m trying to make it better. This makes it better. It’s an abstract exercise for them.”

In the end, despite some discussion he considered “bizarre to the extreme,” the mayor said he’s glad he ventured into the New Urbanist lion’s den.

“I love designers. But right now we’ve got this huge opportunity to do this project,” he said.

“I wish I was able to satisfy every person every way they’d like. I think that’s hard to do sometimes. I also think it’s good to have people prodding you and pushing you even though you find it annoying. What do we learn more from—our accomplishments, or our mistakes?”


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posted by: RJohnAnderson on May 14, 2012  5:11pm

The Mayor asks “What do we learn more from—our accomplishments, or our mistakes?”  Downtown Crossing as it is currently configured has to potential to make Mayor DeStefano a very wise man.

posted by: streever on May 14, 2012  5:41pm

DeStefano says the urban planners just don’t get it-remarkable. What a strange fantasy world we live in where a mayor cramming a land transfer through a hostile public process says that engineers, planners, and designers just don’t get how to do their jobs.

posted by: HhE on May 14, 2012  7:19pm

I’ll give points to the Mayor for daring to show up, but that is as far as I will go.

I too think he is Mayor Lee II.  Richard Lee was a very smart man, with nothing but the best in intentions, and look where it got us. 

I think what has happen is City Hall has embraced an idea (a bad idea), and as residents and experts push back on it, the city just digs in deeper.

Wise is the person who knows when to walk away from a mistake, instead of dogmatically hanging on to it. 

History wil tell, and I think it will judge this administration most unkindly.

posted by: Trajan on May 14, 2012  8:02pm

At age 51 I still retain memories of seeing my family’s business bulldozed into the ground to make way for a Route 34 that was never built. All these years later I still make occasional trips down the Boulevard and circle around empty lots where homes once stood and think about how many lives were disrupted and destroyed in that vacant corridor. I loathe DeStefano but on this single occasion I will give him credit for trying. Although it may be imperfect the fact that it could happen at all is a miracle. And DeStefano is correct in telling Mr. Anderson of faraway Chico, CA that he has no money on the table in this. Johnson also has, apparently, no knowledge of the tortured history of Route 34, the byzantine world of New Haven politics or any sense that money is not exactly falling from the trees on The Green.

posted by: Kevin M on May 14, 2012  8:14pm

No, it is not entirely of New Urbanist principles despite it’s more pedestrian concern. It is not entirely Modernist either though this saga belongs more towards these principles.

Either way there exist SIGNIFICANT promise for development in that area especially compared to other similar cities. Given the competitive nature in today’s ever-volatile world and New Haven’s bright aspects for future certainty, it is of most importance to initiate this whole development responsibly and soon rather than waiting perhaps several years for any shovel to be dug.

Mr. Winstanley’s project will likely activate adjacent projects in the following years, assuming demand and barring crises, primarily through manifesting commitment. His design aspects may still improve or surprisingly worsen. For other future developments particularly along Church Street and a hopefully extended Orange Street, it would be desirable to have a more publicly concerned and less auto-centric pattern.

Critics may be right in that many screw-ups happened from the onset or that there’s “no excuse!” for the current plan’s lasting effects, but it could be a terribly blown opportunity for any dogmatism or technicality to stall Downtown Crossing for who knows how long. Built environments do have the capacity to change for the better and there can be many more opportunities ahead once the ball gets rolling.

*This is from a young man’s perspective with hopefully many more years and the long term in mind.

posted by: Stephen Harris on May 15, 2012  5:52am

I’m glad the Mayor went to the CNU conference. It’s always a good idea to go these things and exchange views.

The most interesting takeaway from the article was the comment about theory versus the real world. I think it’s an indication of just how far off the track modern planning has gone.

New Urbanism (Traditional Urbanism would be an accurate name) is anything but new and it’s not theory. Ironically, it’s the most time-tested way to build urban environments from small villages to large cities.

Anyone who lives here knows that much of New Haven still reflects time-tested urbanism. The city has good bones, as they say. Another way to understand what traditional urbanism is all about is found on a little known land use map tucked away in the library of the City Plan Department. It’s a very large linen map from the early 1920’s depicting the entire city. It shows fine grain, mixed use neighborhoods, an active and bustling downtown, a large working port and railroad. All of these areas are connected by an extensive trolley system. No theory there. It reflects what was on the ground at the time.

What’s new about urban planning was the sudden turn from what works to the auto-dominated experiment dating from about the 1940’s to today. The experiment of planning around the needs of cars has failed because it’s alienating and unsustainable.

Elizabeth Plater-Zyberk and Andres Duany gave a very good presentation of Miami’s new Form-Based zoning code at The Bourse a little while ago. I was disappointed that the Mayor, nor his key representatives didn’t attend. That’s too bad because they would have learned about the process of writing a code that reflects time-tested values.

Does the real world collide with what we want? Sure. It always does, everywhere and everytime. But so what. You soldier on anyway.

I don’t think New Haven’s upper management or political class understands the power of a zoning code to shape development. The mindset here is to negotiate a deal. I truly think that is a backward way to manage growth and prepare for a future that will be very different than the one we live in now.

The low energy cost world of tomorrow is gone for good and the financial system is headed towards a large waterfall. Now is the time to act.

posted by: Atwater on May 15, 2012  8:02am

New Urbanism is a misnomer, actually a branding device for a new program that seeks to exile the working class from the nation’s cities. There is nothing new about new urbanism, its just urban planning pre-Eisenhower age. However, instead of highways cutting off and driving out working people it is high rents, jobs that require an expensive education and a culture that promotes an elitist homogeneity. It’s the suburbs with high buildings, sidewalks and bike paths instead of parkways, strip malls, manicured lawns and cookie cutter houses.

posted by: streever on May 15, 2012  8:36am

I think Hhe nails it on the head, and I think the presentation of one quote is a bit off:

“DeStefano’s reply: “You have no money on the table.” In other words: That’s nice in theory, but the city has to deal with practical realities like investment and revenue and the existing streetscape.”

I don’t actually think this is what is meant. I think it is instead a realist statement of fact. There are certainly any number of aspects to this new plan that are not mandated by the streetscape and existing laws—but the developer has money, and can, in essence, pay to play.

The Mayor has always struck me as very pragmatic, certainly, and I don’t think that is a surprise to anyone who has worked with this administration. I think after 20 years of doing a very hard job, it is not a surprise at all that the Mayor is pursuing a path of least resistance, which is what this incredibly lame and vision-less plan is.

posted by: Curious on May 15, 2012  8:47am

“What they’re building including the Winstanley building seems like a continuation of the suburbanization ... It’s a big box. It’s a lot of cars. It’s not integrated with the neighborhood.”

Amen.  Not integrated, not a destination for anyone other than the people who work there.

posted by: Noteworthy on May 15, 2012  8:48am

Two quick points:

First, I like the core question at the top of the article as it can be applied to a lot more subject areas than just this development.

Second, is the mayor’s concept that half a loaf, that something less than our best is just fine. That’s like getting a “C” in school and it’s not fine. As a city, we should strive to be the best we can be, to achieve the most cohesive, beneficial outcome possible to every collaboration whether it be this development or something else. Instead we settle far too many times for the expedient and easy and only find out later just how expensive and unsatisfying that really is. This development is a case in point and still there are unanswered or unaddressed questions about core issues.

posted by: Scot on May 15, 2012  8:57am

Did any of the plans include leaving the existing expressway to the Air Rights garage in tact as a tunnel and building over it?  I’m not familiar with the various ideas that have been presented, but in theory that seems ideal.  The expressway already sits below the grade of the surrounding streets. Those that want to live in surrounding towns can have a quick and easy commute in, zipping under the city streets.  Then above them we could have nice, calm, pedestrian friendly, two lane roads, bike paths, trees, and can knit the neighborhood back together.  It would get rid of the grade separation from a pedestrian’s perspective, and would also free up additional land for development (since lanes stacked above and below take up less space than 4-5 lane roads).  Does anyone know if a plan like this ever existed?

posted by: anonymous on May 15, 2012  9:05am

“the mayor emphasized that the city has other priorities beyond design, such as school reform, job-creation and public safety.”

Big mistake to separate the two.  The cities seeing job growth, safety, less asthma, and inclusion of lower income residents especially are the cities with good design. The cities that are seeing worse outcomes in these areas are the ones designing everything as anti-urban buildings with huge parking garages for suburban commuters. 

Every designer not on the city’s payroll or a city contractor has said this is a disaster in its current configuration, and that since nothing is being done to mitigate traffic and pollution, surrounding neighborhoods will continue to suffer greatly. Despite 5 years of requests the city refuses to create a model for public view and all renderings, including those shown at CNU, are photoshopped to the point of inaccuracy. Is the Mayor out of his mind when he suggests that viable, sustainable urban design isn’t a priority for our city?

This project has been widely referred to as the worst Federal highway project since the “Bridge to Nowhere” in Alaska, but I think it may be seen as worse since it is right in the middle of the city, with a massive parking garage, and includes no sidewalk in portions. That makes it in clear violation of multiple local, state, and Federal laws. Continuing to build New Haven as if it is just a highway-ringed suburb of Guilford and New Canaan will ultimately cost far more jobs than it creates. At that point, the Mayor and contractors won’t care, because they will have taken the money and ran.

posted by: samgoat on May 15, 2012  9:56am

Why cant we just rebuild the old neighborhood?
It looked really nice from the before photos on
If it was high density, mixed use, and walkable and bikeable it would generate way more tax per acre, and way less car trips than the single one time use glass monstrosity and parking lot currently planned.
Just a thought..

posted by: RJohnAnderson on May 15, 2012  10:18am

“You have no money on the table”

Under this kind of reasoning, if you observe someone making a hugely stupid bet with their constituent’s money, (or in this case Federal money)you cannot say anything if you have not placed a bet yourself.

What will be the result of limiting observations on the Emperor’s new clothes to people with a direct financial interest?

When Route 34 tore out an entire neighborhood, did those people have money on the table?

posted by: Kevin M on May 15, 2012  10:55am

Scot, I believe that is basically the plan which also includes implementing subterranean parking.

Of course Downtown Crossing should be designed to maximize its viability through creating reasons for people to visit and stay. An emphasis on on-street and wrapped parking would help along with strategic and evenly distributed positioning of building frontages and entrances.

However, it may be too much of a stretch to pass a plan that largely “restrains” 34’s vehicular traffic (e.g. terminating 34 earlier). If some commuters consistently drove in and out of New Haven without adding any further engagement, it would be unfortunate. As long as following developments are built well, the area would nevertheless be successful as a place active with life, especially with apartments. I don’t even believe many people would totally skip the city, and they’d be missing out if they were. Having a 34 tunnel with on/off ramps around Church street is a good and practical approach that could best facilitate development.

posted by: streever on May 15, 2012  11:10am

Exactly my read on the meaning behind “You have no money on the table”—I’m not sure what caused the paper to read that the way they did, the expression means “pay to play”—you can’t bet if you don’t put money on the table.

I think—in general—we have a very pragmatic city administration, and I find it unlikely that the intent behind that phrase was as reported here.

posted by: RJohnAnderson on May 15, 2012  11:53am


I can’t speak to how it was reported, but I was there when the guy said it to me. 

He will dismiss alternative designs that are more pragmatic if the author does not pay is what he said.

I figure he will reject more pragmatic designs if he does not understand them and dismiss what he does not understand as impractical.

The mayor is a smart and pragmatic guy, but he remains uninformed or perhaps willfully ignorant on this project.

posted by: streever on May 15, 2012  1:08pm

Thank you for following up and confirming that it was said to you: I’m glad you took the extra step to clear up the intention behind the comment! I’m frustrated when newspapers incorrectly boil down intent/meaning, and glad the comments exist to let you clarify how it sounded to you. The way it was reported seemed very off to me.

posted by: Stephen Harris on May 15, 2012  4:41pm

Atwater and Others,

Here are some useful links:

And New Haven’s very own resource:

These are all great resources.

I would add that Miami had a progressive Mayor who pushed for the new code and made it happen because he understood the good that it will do for Miami over time.

posted by: Jonathan Hopkins on May 15, 2012  4:59pm

The mayor has a point. How would an alternative project be funded? In order to keep the Frontage Roads narrow AND bring the highway to grade, we need connections at Temple and Orange. In order to shrink Winstanley’s garage we need significant transit investments, and the study that would have determined those investments was already crushed by the BOA. Would the State fund the Orange Street connection as part of the redevelopment of Church Street South?
I agree with most of the criticism. Winstanley’s building and the proposed road system are typologically the same as the office and lab buildings and roads shown in the image at the top of the article. The entire system - financing instruments, land-use ordinance, transportation design standards, etc. - favor thisype of development pattern. While New Urbanists and other reformers have been working very hard to change these things, in the meantime, what do we do?

While its true that most of the built New Urban projects fit your description, that is more reflective of the perverse development policies that are currently in place than of the actual New Urban practices. One of the results of New Urban development is to raise property and land values, but those costs are offset by a reduced dependence on automobiles and reduced need for large square footage houses and lots. Mixed use, walkable development enables walking, biking and transit use as a viable option to driving. The development pattern that New Urbanists advocate for also enables for the creation of parks, playgrounds, and shared recreational facilities that are accessibile to children and families from their homes by walking, which reduces the need for individual households to buy their own personal swing set, jungle gym, pool, entertainment room, play room, etc. So property taxes and house prices might be higher, but its still cheaper than the suburban alternative.

A project to rebuild the old neighborhood probably wouldn’t generate a good enough return on investment for anyone to want to finance it. There’s also the issue of the existing highway that needs to be addressed somehow.

You can check out the “Future of the Route 34 Corridor Study”, which the city consulted in the early design for Downtown Crossing, but later abandoned in favor of Winstanley’s plan. Pages 45-68 have different alternatives, although none of them call for maintaining the below ground lanes.

posted by: anonymous on May 15, 2012  8:44pm

Does anyone have access to the list of Winstanley and Winstanley relatives (cousins, brothers, etc.) who have donated to the DeStefano campaign over the past 10 years, including the amounts given? Would make an interesting NHI piece.

posted by: Stephen Harris on May 16, 2012  5:49am


You raise very good points. The overall project is extremely expensive and it unlikely that the best development scenario will be funded.

What do we do in the meantime? My suggestion is that we work with what we have, one step at a time. The Rt. 34E train has left the station but it can fixed down the road by others.

The next step is to abandon the mindset of the big project. They always come with big price tags and, as history shows, don’t have a good track record.

I think the best approach, the one that doesn’t come with immediate gratification or cost that much to implement, is to first get the zoning right. Once that’s in place development can proceed at its own pace in response to financing.

posted by: William Kurtz on May 16, 2012  6:56am

With respect to all, the phrase “no money on the table” is probably better interpreted along the same lines as, “no skin in the game” or “no dog in the fight”; in other words, Mayor DeStefano is (right or wrong) saying that Mr. Anderson, with “no money on the table,” is speaking from a position in which he assumes none of the risks from the wrong course of action. He’s neither a resident of the area nor an investor or stakeholder in the project–except in the ideological sense. It’s a stretch to suggest that it’s a tacit acknowledgment of pay-to-play politics.

Having said that, I am among the critics–not opponents–of the current design of the Downtown Crossing project, even while I understand there are pragmatic considerations that are difficult to overcome. But public policy and development decisions should take a longer span of time into account. This current design is based substantially on the current needs of single-occupant motor vehicles when it should be creating incentives for future transportation needs.

posted by: RJohnAnderson on May 16, 2012  10:07am

No money on the table, no dog in this fight, no skin in the game…
All of these are thrown out to reduce the standing of another person and by extension, the content of their argument.

Is it reasonable that the future of the City can only be decided by those who have a direct personal interest?

The alternatives presented to the Downtown Crossing project went a long way to frame the benefits to Yale Medical, the developer, the mayor, the residents of the Hill neighborhood, and the citizens of New Haven at large,

Eliminating the freeway ramp, filling the ditch with below grade parking for more new buildings, connecting the cross streets with slower speed walkable streets is a reasonable thing to do in which everyone can win. 

A good outcome for all the folks who have skin in the game and money on the table might still be doable if the mayor can remove his head from it’s current location.

If you doubt that such win/win outcomes are possible, look at the replacement of the Central Freeway in San Francisco with the current Octavia Boulevard.