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.