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How 5 essential NYC buildings reveal ‘the soul of the city’

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New York’s hundreds of thousands of buildings are key to understanding its history

Grand Central Terminal.
Max Touhey

If you’ve lived in New York City for long enough, chances are that you have your own personal inventory of notable buildings: the place where your first apartment was located, or the one that’s your lodestar for finding your bearings in a neighborhood, or the one you love simply because it’s beautiful.

There are hundreds of thousands of buildings in the five boroughs, and each one has its own story—both in the larger context of the city’s 400-year history, as well as to individual New Yorkers. That idea is what led veteran journalist and New York Times correspondent Sam Roberts to write his latest book, A History of New York in 27 Buildings (Bloomsbury, $28). Like his previous work, A History of New York in 101 Objects, the book serves as a compendium of interesting structures, with a larger goal of “reveal[ing] the soul of the city,” as Roberts writes in the introduction.

But the list of structures he included is by no means comprehensive—it is, after all, merely 27 out of what may be as many as 700,000 buildings in the city. “This is not the list of definitive buildings,” Roberts says. “This is a list, and more subjectively, this is my list.” In choosing the buildings for the book, he had several criteria: The structure must still be standing, and must have been connected to some important or transformative time in history.

But, more importantly, Roberts wanted to include “the ones people would not notice, the ones that would arouse curiosity, and the ones that would evoke New York history in different ways.” So while there are some famous buildings (like the Empire State, perhaps the most famous building), there are also ones like 123 Lexington Avenue, currently home to the epic Indian grocery store Kalustyan’s, but at one point known for being the spot where President Chester A. Arthur was sworn into office. By revealing the untold stories of these structures, Roberts hopes to spark curiosity about the history hidden beneath the surface of the city—and inspire people to make their own lists of notable buildings.

“I would consider the book to be a starting point,” Roberts says. “I think of this as sort of a parlor game to make people think in a different way about history and about New York—that it’s an ongoing process, that it’s a living process. History is not a dead subject; it’s about things surrounding us that are alive, that tell the story of not what happened in the past, but where we are today and where we’re going as a city.”

Here are five of the buildings to keep an eye out for, straight from Roberts himself.

21 Stuyvesant Street

The Hamilton Fish house, a three-story, early 19th century townhouse located on Stuyvesant Street, is “noteworthy for what it isn’t,” Roberts writes. When the Commissioners’ Plan of 1811, which created the Manhattan street grid, was adopted, Stuyvesant—a block-long roadway situated between Second and Third avenues—was allowed to exist in all its crooked glory. The reason? Its wealthy residents, descendants of that Stuyvesant family, reached a compromise with the commissioners to leave the street alone. “People were fighting over ‘not in my back yard’ over two centuries ago,” Roberts says. (Fun fact: The street is the only one on the island of was Manhattan that aligns exactly with the east and west points on a compass.)

The Bossert Hotel.
Photo by Geo. P. Hall & Son/The New York Historical Society/Getty Images

Grand Central Terminal

Roberts included some famous buildings in the book—including Grand Central, which he’d previously explored in his 2013 tome, Grand Central: How a Train Station Transformed America. Though he initially worried that the subtitle was hyperbole, the more he dug into the history of the building, the more it seemed to fit. “Particularly in terms of urban planning, it shifted the center of gravity in Manhattan from downtown to Midtown,” he explains. But it also changed the way people traveled, in electric trains versus steam-powered ones; it changed how New York City approached historic preservation, with an assist from Jackie Kennedy; it even changed how we tell time. (No, really: Standard time was first used by railroad operators at the terminal.)

Bossert Hotel, Brooklyn Heights

The erstwhile “Waldorf-Astoria of Brooklyn” became famous for its association with the Brooklyn Dodgers in the 1940s and ’50, which is what led Roberts to include it in the book. “First of all, I’m from Brooklyn, so I have a great affinity for [the Dodgers],” he says. But the connections between the hotel and the team go further than that, with Jackie Robinson being courted by team managers there, and the Dodgers celebrating their World Series win in 1955 in its basement. Bossert is also where, in 1957, team owner Walter O’Malley made it clear that the Dodgers would be moving to Los Angeles. “It’s not the be all and end all” of Brooklyn buildings, Roberts says. “But it became the vehicle to be able to tell that story.”

134 East 60th Street

There’s a four-story brownstone embedded within a glassy Upper East Side high-rise, and it’s all thanks to Jean Herman, who lived in a rent-controlled apartment at 134 East 60th Street for more than 30 years. Her refusal to vacate her apartment led Cohen Brothers Realty, the developer who bought the building, to construct a skyscraper around it—and even though Herman died in 1992, the odd arrangement remains to this day. Roberts included it as a nod to the development fights happening throughout the city today. “Too often we think of things happening for the first time, when in fact many are part of a continuum,” he says, citing holdouts and fights over development as examples. “One of the things history helps give us is a sense of where things are coming from and where they’re going.”

American Bank Note Plant, South Bronx

A positively massive, block-long building in the South Bronx was, for a period of time in the 20th century, churning out billions of dollars every day—literally, since it was a plant used by the American Bank Note Company to print currency until the 1980s. But its identity remained largely secret, despite its location within a borough that was experiencing devastating fires, displacement of its residents, and urban decay. “Here’s the poorest neighborhood in the country, and here’s an obscure, isolated factory turning out billions of dollars in currency that nobody knows about,” Roberts says. “These dichotomies, these contradictions—I just found fascinating.” Now, it’s known as the Banknote Building, and has been renovated into office space.