Who will follow in Amanda Burden's (very stylish) footsteps?

With the New York City mayor's race not even past the Democratic primary, it's a bit early to be handicapping the city's next chief city planner, but where's the fun in being coy?

Crain's has taken a look at who might fill the post, which it calls "perhaps more important than any deputy mayor position at City Hall," arriving at a short list that includes names ranging from Vishaan Chakrabarti, a consummate real estate industry insider and former director of the Manhattan office of the Department of City Planning, to the more community-minded Anna Levin, a member of the City Planning Commission and the chair of Manhattan Community Board 4's Land Use Commission during most of the 2000s.

But when we spoke to Greenwich Village Society for Historic Preservation's Andrew Berman about who might be the city's next chief city planner, he threw cold water on the speculation.

"I think that the choice of who the chair will be, while it certainly tells you something, who the mayor is tells you more," Mr. Berman said.

He cited the evolution of Amanda Burden, widely heralded as driving the relatively radical rezonings—radical, at least, for the staid post-war planning years; there hasn't been a major revision to the city's code since the 1961 overhaul—of the Bloomberg years. Under Burden, development rules for a third of the city's land were changed in one way or another.

"Amanda was a very, very different member of the City Planning Commission when she was Mark Green's commissioner"—Mr. Green appointed Ms. Burden to the commission as the city's first public advocate—"than when she was Mike Bloomberg's."

"Some would argue," Mr. Berman continued, "that the Amanda Burden who served on the City Planning Commission [under Mark Green] wouldn't even recognize [today's] Amanda Burden."

Back before she became the face of Michael Bloomberg's Big Real Estate-friendly rezonings, Ms. Burden was not so well received by the industry. “I think there’s a concern about the prejudices she may bring to the position,” one developer told The Observer back in 2002. “I don’t think she was at the top of [our] list. But I think we feel that we can work with her, since we have no choice.”

Dapper though Mr. Chakrabarti may be, don't expect New York City's next chief planner to make the cover of Women's Wear Daily.

Of the candidates identified by Crain's, Mr. Chakrabarti and Ms. Levin sit on opposite sides of the pro- and anti-development spectrum.

"Folks from the real estate industry feel that they are entitled to more or less choose who the next chair is," Mr. Berman told The Observer. He wouldn't single out any candidate, but we can't help but think he was referring to Mr. Chakrabarti, who has been an unfailing advocate for density around New York's many transit hubs.

"Mr. Chakrabarti's group at Columbia University," wrote Crain's, "is expected to release a report soon showing that the city does not have the zoning capacity for the 1 million new New Yorkers expected by 2030 and is short about 300,000 residential units. As commissioner, Mr. Chakrabarti would likely support the upzoning of neighborhoods like Long Island City and the South Bronx that are one or two subway stops away from midtown."

Mr. Levin, on the other hand, has shown herself to be much more interested in affordable housing, and less interested in increasing the size of the city's overall housing stock, often expressing that distinctly West Side antipathy towards density.

She was, for example, the lone vote against Extell's Riverside Center project, saying the project was "too big."

And Ms. Levin and Mr. Chakrabarti stood on opposite sides of an early debate over the future of Hudson Yards back in 2003.

"We feel that the amount of growth planned for the area is essential to the long-term growth needs of the City of New York," Mr. Chakrabarti, then with the Department of City Planning, told The Observer.

Ms. Levin felt differently. "The city wants to create five World Trade Centers’ worth of new development. We feel that this is just too much," she said at the time, arguing that "the city must proceed without crushing the existing neighborhood."

Massing diagram of the Astoria Cove project, from the environmental assessment statement.

The Halletts Point redevelopment proposal to bring 2,644 apartments to a forlorn peninsula of the Queens waterfront has been in the works for three years, but now a different developer is throwing its hat into the ring.

The vaguely-named 2030 Astoria Developers LLC submitted an early application to the Department of City Planning today to rezone another smaller chunk of Halletts Point. They're calling the project Astoria Cove and they want to build another 1,535 housing units—a combination of townhouses and apartments—on a site overlooking Pot Cove in Astoria, with a pristine view of the Queens leg of the Triborough (RFK) Bridge. Twenty percent of the project, or about 340 units, would be set aside for affordable housing.

The site sits on Halletts Point, the bulbous peninsula on the Astoria waterfront right above Roosevelt Island.

When asked about the identify of those behind the LLC, Sean Crowley, the lobbyist who's representing the developers and is the brother of Congressman Joe Crowley, told The Observer, "I'd rather not speak for them at the moment."

"The buildings located along the waterfront," reads the environmental assessment statement, "would have base heights between 80 to 100 feet that would be topped with towers ranging in height from 120 to 300 feet," with the buildings further inland topping out at around 80 feet.

In addition to opening up the waterfront—with about twice the 20 feet of space required by the Department of City Planning, according the developer's lobbyist—the builder is also planning to leave room for a 456-seat public elementary school, and "is exploring providing shuttle service for residents during the weekday a.m. and p.m. peak hours to and from the 30th Avenue station serving the N and Q lines." (The proposed development is about three-quarters of a mile from the nearest train station.)

Contacted by The Observer this afternoon, Councilman Peter Vallone, who represents Astoria, said that he hasn't yet thrown his support behind even the first project. The project, he said, "came in at almost twice the size they are now, so for years we've been working to whittle it down to something that's economically feasible for them."

The site is currently made up of vacant lots and underused industrial structures.

"That peninsula needs development," Mr. Vallone said, "and can't be left as it is. It has dilapidated warehouses on the waterfront. People on the peninsula have no bank, no supermarket." The developers are planning to build 117,000 square feet of retail, including a 25,000-square foot supermarket.

"But the problem," Mr. Vallone continued, "is that both of these projects are going to be very large, and until I get commitments from the city"—on transportation infrastructure, especially—“I can't support them."

He did, however, acknowledge the economic realities of development in the city. “If they can't come in big," he said, "they're not coming in."

The Municipal Art Society is worried that the Midtown East upzoning would allow development that would block views of the Chrysler Building, among other landmarks.

Based on the arguments made by those both for and against the Midtown East rezoning—a "sweeping proposal," wrote New York magazine architecture critic Justin Davidson, with "swollen ambitions for the skyline"—one might think that the proposed land use change, which would affect 78 blocks between Second and Fifth Avenues and East 39th and East 57th Streets, would be a dramatic revision of New York City's most hallowed business district.

Crain's New York Business calls the plan "essential." The Post’s Steve Cuozzo, ever a friend to big real estate, says it's “vital to the city's future, a way to ensure that Manhattan's most desirable commercial zone can compete in the future with global capitals like London and Shanghai."

Meanwhile, opponents of the plan to rezone the area north of Grand Central Terminal have painted it as a death knell for some of New York's most iconic sites, and a massive imposition on an already-overburdened transit system. "The rezoning study makes no mention of protected-view corridors," wrote starchitect Robert A.M. Stern, coming out against the plan in today's New York Times. "I can hardly make my way to the stairways and escalators that lead to the Lexington Avenue subway platforms."

The Municipal Art Society, which has proposed landmarking 17 pre- and postwar towers in the area (the Historic Districts Council has a list of 33), commissioned mock-ups of potential new towers that could obscure the district's most famous buildings, writing, "The verifiable photo simulations show how iconic buildings such as the Chrysler building will not be visible from many vantage points if development occurs as proposed."

But delve into the actual numbers on the proposed rezoning, and it starts to look like much ado about nothing. As the Wall Street Journal’s Eliot Brown pointed out on Twitter, only 3.8 million square feet of office development is expected beyond what would be built without any zoning changes, according to an environmental assessment released by the city on Friday, or 4.4 million square feet of total extra development taking into account all uses. (While more than 14 million square feet of new office space could rise, two-thirds of that would replace existing buildings.)

Compare this to the rezoning of Manhattan's far west side earlier in Mr. Bloomberg's term, where nearly 26 million square feet of new office space was allowed in Hudson Yards—an area with far worse transit and less new investment ($8.4 billion for East Side Access, which will bring the Long Island Rail Road into Grand Central, versus just $2.1 billion for the 7 train extension to 34th Street and 11th Avenue)—and the Midtown East rezoning starts to look downright puny.

With just 3.8 million square feet of new office development expected out of the plan in an area that already contains 70 million square feet of office space, the Midtown East upzoning would barely add more floorspace to the district than the Port Authority is building in One World Trade Center—3.5 million square feet of floorspace in one tower alone.

Even the Williamsburg and Greenpoint rezonings, which added over 30 million square feet of residential development rights, dwarf what Mr. Bloomberg and the real estate industry want to add to Midtown East.

Given the relatively small numbers involved, both sides should drop the histrionics: the Grand Central upzoning just isn't that grand, and isn't going to make or break Midtown East either way.

A massing diagram from 606 West 57th Street's rezoning application.

Back in 2011, AvalonBay abandoned plans to build a 44-story, 700-unit rental building on the block south of West 57th Street between Eleventh and Twelfth Avenues. TF Cornerstone was rumored to be interested in the site, and it turns out the rumors were true: the Manhattan-based developer now wants to build a 45-story, 1,189-unit residential tower on the same site, according to documents filed with the Department of City Planning.

If approved, the project would contain a total of 1.2 million square feet of floorspace, with 42,000 square feet set aside for commercial use and a 550-space underground parking garage. Of the apartments, 20 percent—238 units—would be set aside as affordable housing under the city's inclusionary zoning program.

The project would, along with the residential pyramid that Bjarke Ingels is building for Durst Fetner on the north side of 57th Street, anchor the booming crosstown corridor, where half a dozen other luxury towers are in the works.

One of the site's more attractive buildings.

TF Cornerstone will have to go through the same private rezoning process for 606 West 57th as Dursts and Fetners had to do with the Bjarke Ingels building, involving a slurry of acronyms and eventually a vote in City Council. They're seeking to rezone the parcels—which make up most, but not all of the block—from their old manufacturing designations to a zone that allows the highest residential density in the city.

A building on the southeastern corner of the block, included in the rezoning application but not in TF Cornerstone's project, is owned by Republican mayoral candidate and Gristedes owner John Catsimatidis.

TF Cornerstone signed a 99-year lease for the site last May, leasing the land from Montgomery, Alabama-based Four Plus. Charles Edgar Appleby, the progenitor of Four Plus, first acquired land on Manhattan's West Side in the 19th century. He once declared, "It has been my rule to keep the value of my property in land, not in buildings." Apparently his offspring feel the same way.

Holding out for hotels. (Getty)

Everyone has been praying for the inclusion of churches and synagogues in the Midtown East rezoning, but no one has checked in on the situation of hotels yet.

The religious institutions fear they will not be able to profit from the rezoning the same way their private neighbors will. Now, the hotel union and its political backers are worrying that hoteliers might be in the opposite position, of profiting too much from the rezoning. They are requesting that the Department of City Planning require special permits for new hotel development within the rezoning area. So far, the Department of City Planning has reservations about the proposal.

The Hotel and Motel Trades Council, which represents some 30,000 hospitality workers in the city, is arguing that without requiring developers to seek a special permit, hotel construction might outstrip that of office development, which is the main goal of the rezoning. The rezoning area stretches roughly from 57th Street to 39th Street between Fifth and Third avenues, with a heavy emphasis of promoting development along Park Avenue and around Grand Central.

A special permit also helps ensure union jobs within any hotels that do get built, as The Observer's David Freedlander explained in a profile of the union's boss, Peter Ward. By making hotels pass through the city's public review process, they require the stamp of the City Council, which is hugely pro-union. Granted requiring this support explicitly is forbidden, but that is what private negotiations are for.

The union thus sees this provision not only as a boon for office builders but also the city's hard working masses. "Many hospitality jobs are middle-class jobs in New York City because of the Hotel Trades Council contract," union political director Josh Gold said. "By implementing a special permit process, we can ensure that this area is not overrun by too many hotels. Protecting middle class hotel jobs is a clear way to stem growing income inequality in New York."

The union points to areas like Hudson Square and Times Square, where hotels have proliferated, at times in direct competition with office space. The Hudson Square rezoning already features a hotel special permit prevision to put an end to the new hotels (there was a minor boomlet with the Trump Soho and some budget-rate places) and instead encourage new offices down there.

The hotel union wants to see the same thing in Midtown, but the Department of City Planning, in its initial analysis of the area's needs, does not yet consider such a permit necessary, and even sees it as a possible detriment to the redevelopment of Midtown East.

"Hotels provide accommodations for visitors, space for meetings, conferences and entertainment, foot traffic for businesses in the area and jobs for New Yorkers," a department spokeswoman said in a statement. "East Midtown is, in fact, the ideal location for hotels–it is centrally located with excellent access to mass transit, and is home to some of the city’s best business, landmark and tourist destinations. Hotels in East Midtown are key to the continuing growth of New York City’s tourism industry, and they have always been integral to Midtown’s identity and success."

Councilman Dan Garodnick, who will have final say on the Midtown East Rezoning should it enter public review next year as planned, disagrees with the department's stance. He said in an interview he was worried about having hotels overtake other types of commercial development. He also cited neighborhood concerns as a reason to require special permits for hotels.

"From a community perspective, I hear about hotels from my constituents all the time," he said. "When you have neighborhoods that are residential, with hotels in them that are 24/7, it can cause problems. There are deliveries, there's catering, drop-offs, visitors, conferences. From a land-use perspective, they're a totally different animal."

They want more to look at. (Getty)

Earlier this week, Councilman Dan Garodnick called on the Department of City Planning to slow down the planning for the new Midtown East rezoning that would add possible a dozen new skyscrapers to the Manhattan skyline. The argument was that with such an important rezoning—the city's fate as a competitive marketplace hangs in the balance!—more time was needed to consult all the parties and get the plan right.

For essentially the same reasons, the department is now arguing that it cannot wait. Time is of the essence to get these new projects underway.

In an email statement (in full below, with highlights by us), the department argues that developers need time to to assemble their sites and start building when the restriction preventing new projects before 2017 lapses. Previously, the department had argued that it was not as though all these new buildings would be built overnight, but rather this was a long-term plan that would take decades to fully develop. This raises the question of whether waiting six more months to debate the plan, as Councilman Garodnick and the local community boards are asking for, would really hurt the plan.

"We want to make sure that there is certainty, and we also want to make sure this is done right," Councilman Garodnick said in a statement. "The proposal has merit, and allowing a few more months to what will be a decades-long process would help ensure that all issues are vetted and considered."

The department remains eager to finish this before the end of the Bloomberg administration, though it must also be careful not to anger the Council, which after all has final say on all rezonings.

The purpose of the East Midtown rezoning proposal is to secure the area’s future as a premier business district by encouraging the development of a small number of new, state-of-the art Class A office buildings over the next two decades. Recognizing the fundamental importance of East Midtown to the City’s economic future, the Mayor has made this rezoning a priority for the Administration.

Under the proposed timeline for this project, the first new buildings are not likely to come online until later this decade or next, but this can only happen if we set in place zoning mechanisms now. Adopting a predictable zoning framework in 2013 is a necessary prerequisite for the development of new high-end commercial buildings over the long term. In the near term, property owners need certainty and predictability to make significant financial commitments that will ultimately lead to these new developments. It takes many years to assemble sites, and yet more time to decant, demolish, and prep the site for development. Having the new zoning in place within 2013 will provide the certainty and predictability necessary.

With these new developments will come much needed improvements to both the on‐street and below ground pedestrian networks. We are proposing that major new office towers be required to contribute to a fund for specific and targeted transit and pedestrian improvements in and around Grand Central Terminal that will reduce subway congestion points, increase capacity on platforms and transform Vanderbilt Avenue into a signature pedestrian gateway

As with all of our projects, we have been carefully analyzing the area and meeting with area stakeholders, including the community boards, to discuss the issues and proposed policy solutions so that an appropriate long‐term zoning framework for East Midtown can be created. There is ample time to complete all the necessary review and analyses for this project, and we are committed to continue working closely with the community and other stakeholders as the process moves forward.

Some have compared East Midtown to Hudson Yards, saying that the Hudson Yards rezoning took years before it entered the public review process. East Midtown is a vastly different proposal than the Hudson Yards rezoning, which contemplated a complete transformation of the area equivalent to adding half of downtown Boston’s office space floor area. This was in addition to new streets, parks and open space, more than 14,000 apartments, an expanded Javits Center, a Sports and Convention Center and the extension of the #7 subway. In East Midtown, our proposal is much more targeted—it builds on the existing character of the area and is designed to facilitate a substantially smaller amount of new development.

Any delay of this proposal means uncertainty for East Midtown. Given the importance of East Midtown to the City—for its jobs, tax base, and its critical transportation role—we must put into place a new regulatory framework that strengthens, not stymies, East Midtown’s continued competitiveness on the global stage.

Lofty goals. (Trinity Real Estate)

Last Friday night on far west Spring Street, the Ear Inn was crowded as usual. A mix of neighborhood regulars and happy-hour-indulging co-workers from the nearby loft buildings—architects, ad execs, programmers, writers—were crammed around the mahogany bar imbibing. Others were gathered outside around benches on the uncrowned sidewalk two blocks from the West Side Highway.

The bar has been there for 195 years, but forget asking for some sort of mixological cocktail that could be found at hundreds of establishments citywide pretending at this sort of authenticity. Above the bar, beyond the shelves of dusty liquor bottles, are glass carboys, ruddy green and brown glass, the size of harbor buoys. They held wine more than a century ago and disappeared into the bowels of the basement, only to be excavated in the 1970s when the bar was made over by a band of eccentric artists. One of their rank tended bar until five years ago. He has since moved upstate. Things change, then they don't.

“We’ve gotten the holy trinity of Pret a Manger, Starbucks and Hale & Hearty soups, but otherwise the neighborhood looks the way you imagine it did 100 years ago,” said James Parvin, a segment producer at NBC who lives in a loft he converted himself on nearby Charlton Street.

With the exception of those at the Ear Inn and down the block eating at 508 Restaurant & Bar, by 7 o’clock the surrounding streets had largely emptied out. The only real activity was the wall of cars creeping, honking, into the Holland Tunnel. Empty is how the streets would largely remain until 7 o’clock Monday morning, when the workers would begin filing back into their postindustrial warrens along Hudson and Varick Streets.

This is how vast swaths of downtown Manhattan used to look, dead in all but daylight, from Soho to Chelsea to the Financial District. Hudson Square, as developers began calling the area bounded by Houston Street, Sixth Avenue, Canal Street and the river in the 1980s, is all that is left. Or all that was.

Nothing but blue skies that I see. (gsz/Flickr)

On Monday Afternoon, the City Planning Commission certified a carefully crafted rezoning scheme furnished by Trinity Real Estate, the property management arm of the city’s oldest church, and once its largest landowner. Trinity’s holdings have been winnowed down over the years, confined largely to the plots it owns in Hudson Square.

For the past five years, Trinity has been devising a plan to turn a number of sites it controls in the area into housing, that most lucrative of New York City real estate ventures. Along the way, it has created the largest private rezoning in city history, twice the size of the massive 26-acre Hudson Yards development 40 blocks to the north, three times the size of Columbia’s new Manhattanville campus.

“Mixed-use communities, such as the Flatiron District and Union Square, which are attracting new businesses and residents, contribute significantly to the dynamic appeal and economic vitality of the city,” Jason Pizer, president of Trinity Real Estate, said in statement Monday. “The proposed rezoning would reinforce Hudson Square as a vital hub for the jobs which are so integral to the city’s future.” Trinity declined to publicly discuss the project until it goes before the local community board next month.

Will this effort really be able to transform the last untouched corner of Manhattan, to make it look, feel and behave like the rest? An earlier rezoning along Renwick Street a decade ago saw a spate of new condo projects that would portend much of the development that swept the city in the ensuing years. Philip Johnson’s last building is here, the Urban Glass House, completed after his death. His modern lofts were, until a few months ago, uniformly selling for less than the bankers and lawyers and foreigners had been paying when they first moved in a few years prior.

One of the most quietly beautiful couples in the entire city, Jennifer Connelly and Paul Bettany, traded Park Slope—Park Slope!—for Hudson Square. Now they are reportedly leaving, their West Street penthouse on the market for $8.5 million. Their neighbors include John Slattery, James Gandolfini and that other fabulous couple Lou Reed and Laurie Anderson. All have said they were drawn here because of the quiet of this unassuming neighborhood, so hard to find anywhere else these days.

“We’ve gotten pretty used to construction over the past decade,” Gary Lawlor, an Ear Inn bartender for twice as long, said. “That hasn’t changed anything, so I don’t think some more new buildings will, either.”

The question has become: How much say should any one entity have over an entire neighborhood?

Arguably (even inarguably) Mayor Bloomberg and his planning commissioner Amanda Burden have exercised the power to reshape the entire city during the past decade, but they were elected and appointed to the job. Carl Weisbrod has Hudson Square almost to himself.

A City Hall hand going back to the Koch administration, Mr. Weisbrod arrived at Trinity in 2005 to run the real estate division. He spent a good part of that time very astutely filling the former printing plants, but his big task was going beyond business. He was focused on the streets, not the C suites. Mr. Weisbrod, who left Trinity last year to become a partner at planning shop HR&A, certainly had the experience. He spent 20 odd years cleaning up Times Square followed by a decade in Lower Manhattan as founding director of the Downtown Alliance. Half that time was spent helping to rebuild after 9/11. Reshaping a neighborhood like Hudson Square would be nothing.

Always a school, always. Here, part of a marquee development on Canal Street. (SHoP Architects)

It is the same thing Trinity has been doing for downtown for more than three centuries. The church was established in 1697 by the grace of King William III. The third church still stands at the top of Wall Street, its 281-foot steeple, completed in 1846, was the highest point in the land until the New York World building surpassed it 54 years later. Real estate has always been at the heart of the church.

Queen Anne made Trinity what it is to this day through the generous land grant of 215 acres, much of it farmland (the annual rent was one peppercorn). Over time, much of that land was given away, granted to churches, schools and other charities, most notably Kings College, today Columbia University. What remains of the church’s holdings is concentrated in Hudson Square.

The area has largely risen and fallen with the tides of the city. After the cows and crops moved on, it became dockland when Manhattan was ringed with piers. When wheels began to replace rudders, Hudson Square became a hub of printing, starting in the 1920s, primarily for Wall Street—contracts, prospectuses, research—though everything from books to greeting cards was common. They were perhaps the very first victims of the digital age.

By the mid-1980s, half of Trinity’s 6 million square feet of industrial space in the neighborhood was bankrupt. The church rectors decided something had to be done. In 1987, Tishman Speyer, building on Trinity’s land, completed 375 Hudson Street. Saatchi & Saatchi, which took nearly half of the 900,000-square-foot building, was the anchor tenant. One by one, the old printing lofts were remade, and many stalwarts of the creative class—MTV, New York magazine, Edelman, Rafael Viñoly architects—followed. Vacancies stand at 5 percent, the lowest rate in the entire city.

It would seem Trinity should be building more office space, but the church is going in a different direction. To attract the kind of vibrant retail that will truly make their tenants’ lives (and their rents) top-notch, some lovely loft apartments would surely help the street life. Many storefronts are perennial losers, especially the restaurants.

Trinity wants to transform some five undeveloped sites it owns, along with up to a dozen it does not, into grand new apartment buildings in the style of the neighborhood’s existing industrial buildings. A number of complex zoning regulations have been proposed. These are meant to maintain the bulky historical look of the area while limiting the slender hotel towers, most notably one bearing the name Trump, that have sprouted in the neighborhood over the past decade. Still, along the avenues, buildings up to 30 stories will be allowed.

In total, the rezoning is expected to create more than 3,000 new apartments in the area, spread across those dozen sites, with the possibility of additional smaller projects. Roughly one in five apartments will be affordable, through development bonuses offered in the zoning. Special measures have been put in place to discourage the demolition of the existing loft buildings or their conversation into apartments. Basically, any office space that is eliminated must be replaced in a one-to-one basis somewhere within the district. Special approvals are also required for new hotel construction.

It is largely the same playbook the Department of City Planning has been honing throughout the Bloomberg years to encourage development, preserve neighborhood character and foster affordable housing. And yet the plan does not sit well with many in the neighborhood, precisely because it is being undertaken by Trinity and not the department itself.

Occupy Hudson Square. (Getty)

Hudson Square has been through a lot in the past few years.

Before the rezoning, there was the hullaboo about the outsized Trump Soho, where 391 “condos” were for sale in the 46-story “hotel.” Residences are illegal in construction zones, so an eventual compromise was reached to restrict owners to 120 days a year at a stretch of no more than 30 days. It was this sort of out-of-context, out-of-bounds development that helped spur on the rezoning.

Then came Mayor Bloomberg with plans for a sanitation garage. The garbage trucks have to park somewhere after all, and the mayor had rightly vowed to stop dumping them all in the outer boroughs, especially the South Bronx. Each borough would have to take its fair share. Messrs. Gandolfini, Slattery and Reed were far from O.K. with this—think of the property values!—and they hosted rallies and benefits, replete with red carpet, even commissioned a local architect to offer an alternative. Mr. Gandolfini was among the plaintiffs of a lawsuit attacking the city for the plan. It passed anyway, and steel currently rises to five stories at the corner of Spring Street and the West Side Highway. Trinity seems to have embraced the building as a mark of the neighborhood’s mixed character.

Then there was the Occupation. One of Trinity’s main reasons for developing all this real estate is to fund the church’s charitable work. In addition to fighting to end apartheid by funding Reverend Desmond Tutu and providing brown bag lunches every Wednesday on the steps of the old church, Trinity gave greatly of money and resources to Occupy Wall Street, including office space in Hudson Square. When the eviction finally came from Zuccotti Park last December, the Occupiers briefly moved into Duarte Park, the future site of that marquee tower. After vandalism and other strains of lawlessness ensued, they were evicted from the space.

Now it is Trinity’s turn to stir things up a little.

At Monday’s planning meeting, some commissioners questioned why it was a private developer, and not the city itself, that was undertaking such a monumental planning effort. “This is a private application that very much looks and smells and feels like a neighborhood rezoning,” Commissioner Anna Levin said. “I’m curious about the degree of interchange between staff and the applicant in taking this up and shaping it. Also, the extent to which other stakeholders and other property owners have been consulted.”

Edith Hsu-Chen, director of the department’s Manhattan office, responded, “Certainly this is a neighborhood rezoning, one put forward by a private applicant. As we have many applications, certainly, with this amount of coverage, there have been discussions with the department. But again, this is a private application, as we want to make clear.”

There are the usual complaints from the neighbors, of course, about schools and affordable housing. The preservationists are worried not only about the integrity of the old loft buildings but also some Federalist-style townhouses sprinkled throughout the district. But the biggest bellows actually come from a number of prominent developers who own land in the area but do not bear the cross.

“The urban design regulations are too generic, they don’t apply well to Hudson Square’s unique grid, and they don’t accommodate the type of development the plan aims to produce.” Anthony Borelli, vice president of planning and development at Edison Properties, told The Observer. His firm owns a parking lot just above the mouth of the Holland Tunnel, a fact that makes its redevelopment difficult, as half the site is unbuildable—dig down for a foundation and you hit the dead space below. But the historical covenants in place make a setback tower impossible.

“On one hand, Trinity’s plan sets a goal for creating approximately 6,000 residential units, including affordable housing, to make the area a vibrant 24-hour neighborhood,” Mr. Borelli said. “But then on the other hand, its urban design regulations make it virtually impossible to achieve that many units or to fully use the city’s inclusionary housing program.”

Gary Barnett, head of Extell Development, placed much of the blame on City Planning. “I’m not sure Trinity really cares,” he said.

Too big, too fast? (DCP)

Easy does it. That is the message from Councilman Dan Garodnick, echoing concerns of two Midtown community boards, that the Bloomberg administration is moving too fast in its plans to rezone Midtown East to allow for taller skyscrapers.

The Councilman, who represents the eastern flank of Manhattan, applauded the plan in a letter [PDF] to Planning Commish Amanda Burden last week shared with The Observer, but he worries to plan is so complex, it needs more time to be considered. The Department of City Planning argues there is enough time to get the job done before the Bloomberg administration is out in a year and a half.

"It's certainly important to ensure that our Midtown core remains competitive with cities around the world," Mr. Garodnick told The Observer. "At the same time, we need to approach this rezoning proposal deliberately. I understand that the mayor's term has less than 500 days remaining, but that should not be the prime factor in driving the time frame for such an important proposal."

Primarily, Mr. Garodnick wants the scoping session, when the framework is solidified, pushed back six months to March. In the letter, he also criticized plans to release an initial framework in the coming weeks, "before Labor Day—when many New Yorkers are totally disengaged from the political process." The plan was to have the massive rezoning—both in space and scope—enter public review by the first quarter of next year, but pushing back scoping would likely push that into the summer or fall. The rezoning would almost certainly be approved by the next administration as a result.

There is some concern this could scuttle the plan, but Mr. Garodnick sees it as a way to foster a stronger one. "Indeed, there is no harm in having this proposal be initiated by the Bloomberg administration and finalized by the next mayor, whoever it may be, and for it be a shared legacy," Mr. Garodnick wrote. He argues that because the plan will be implemented until 2017, there is no need to rush the rezoning.

In a July 20 letter to the department, Community Board 5 mounted a similar case:

Given the enormous complexity and high stakes for this rezoning, we ask that the Department slow down its timetable so that the community can fully consider and respond to your plans and so that the Department can take the community's concerns and wishes into account, allowing time for town hall meetings, public hearings, and other forums. As a point of comparison, by its own account, the Department spent about five years to develop the plan for Hudson Yards, and just recently, the same amount of time to rezone a stretch of the Upper West Side. Closer to East Midtown, DOT and the Grand Central Partnership have spent nearly three years thus far to develop the plan for the Pershing Square pedestrian plaza. Certainly a project with the magnitude of East Midtown at least merits similar timetables.

There are those who believe the city is dragging its feet, however, namely Post real estate columnist Steve Cuozzo. He took to the tab's editorial pages today to slam the Midtown East plan from the other side. He said the city should not wait until 2017 to let developers build bigger. But his main issue is with a neighborhood improvement fund developers would finance by buying air rights: "The city wants the dough to remedy such horrible 'pedestrian realm challenges' as 'narrow sidewalks and bottlenecks in subway stations.' Hello, slush fund?"

The neighborhood New York forgot. (Hudson Square Connection)

Trinity Church has controlled vast swaths of Lower Manhattan real estate for more than three centuries, since the Queen of England deeded 215-acres to the church in 1705. Much of that property has been given away or sold off, but the church still controls one pocket of land at the mouth of the Holland Tunnel, known affectionately these days thanks to developers and brokers, as Hudson Square.

Over the years, the neighborhood has been remade repeatedly, from farmland to factories to the heart of the city’s printing district. More recently, it has become a hub of media and tech firms—Saatchi and Saatchi, New York magazine, MTV, the New York Genome Center—but the church wants to take things a step further and create a 24/7 live-work neighborhood, like neighboring Soho and Tribeca.

For the past five years, Trinity has been working on a rezoning of 50 acres spread over some 20 off-the-grid blocks—the area often feels remote cut off from the rest of the city as it is by the Holland Tunnel. On Monday, it officially begins the public review process, as the City Planning Commission is expected to certify Trinity's in-hourse rezoning proposal.

The area is generally bounded by Sixth Avenue on the East, the Hudson River on the West, Houston Street to the north and Canal Street to the south. The rezoning will be slightly smaller than that, but at twice the size of the Hudson Yards development 40 blocks north, and three times as big as Columbia’s new Manhattanville campus further north from there, it is by far the largest private rezoning the Department of City Planning has ever underwritten.

It is also one of the most complex, with contextual zoning elements meant to preserve the neighborhood character; open space provisions meant to foster more plazas and parks in an area that has almost none; plus schools, affordable housing, even plans for dealing with night clubs, of which there are already a few in the area. The idea is to create opportunities for housing without stymieing the businesses that have already taken root.

A spokesman for Trinity declined to discuss the project until it is officially certified.

Some locals have already complained that height limits for new buildings are already too high while developers outside of Trinity express concerns about their ability to build. The area is home to celebrities, among them James Gandolfini, Jennifer Garner and Lou Reed, as well as ignominy in the form of a coming garbage truck garage all those stars hate. Meanwhile, one of the primest development sites, Duarte Square along Canal Street and Sixth Avenue, has already made headlines.

It is the empty lot, once a temporary art park, that was taken over by Occupy Wall Street following their eviction from Zucotti Park. Initially, Trinity was happy to have the guests until they showed hostility toward their hosts, at which point the NYPD forced them out, and the park has remained locked up ever since.

Hopefully the rezoning will prove to be less contentious.

Correction:A previous version of this post misstated the year the Queen deeded the land to the church. It was 1705, not 1773. The Observer regrets the error.

Now that's a skyline. (William Weber/Curbed)

How does it compare to today?

Back when we did our big report one what the Bloomberg administration has in store for Midtown East under an in-the-works rezoning, we came up with a little dream/doomsday scenario of what that might look like. Then, when the city officially unveiled the plans, they revealed that some sites could potentially see buildings as big or bigger than the Empire State Building, and they produced their own images of this brave new world.

Now, our pals over at Curbed have come up with their own rendering of a Midtown of the future, which are equally exciting and terrifying, depending on where you stand on cool new skyscrapers and the crowds and shadows that come with them. Which camp are you in? Let us know in the comments.