4. Manhattan’s Two-Part Skyline

A view of the city skyline from across the water.

Manhattan’s downtown cluster of skyscrapers rose in the early 20th century, notably in the Art Deco style, while Midtown rose decades later, especially in the Modern style.

From 1890 until 1973 Manhattan had nine buildings that were the “tallest-in-the-world;” a title that leapfrogged four times over 83 years between downtown and midtown. The first three (the World, Park Row, and Singer Tower) were in the vicinity of City Hall for the first 20 years. For four years, from 1909-1913, the title went uptown at 23rd Street with the Met Life Clocktower before returning downtown again for 16 years with the Woolworth Building and 40 Wall Street. In 1929 it returned back uptown with the Chrysler Building, and 42nd Street became the uptown limit of New York’s “world’s tallest” buildings. When the Empire State Building opened at 34th Street it would hold the title for a stunning 40 years until 1971, when it returned downtown for the last time with the World Trade Center. In 1973 Chicago took the title and it hasn’t been back.

Of New York’s nine tallest-buildings-in-the-world, six were downtown (three faced City Hall), and three were uptown between 23rd and 42nd Streets, barely Midtown. 

It’s interesting that the Empire State Building was built 8 blocks downtown from the Chrysler Building (in an otherwise uptown-moving city), and downhill from Grand Central Terminal (for which it needed easy and convenient access; Penn Station aside). It’s something of an anomaly, considering the importance of a building to its site, that the Empire State Building was built at the bottom of Murray Hill.

This is a great example of the palimpsest metaphor as a tool for thinking about how cities change through time and space, and a way to decode the streetscape by building, block and neighborhood (an upcoming post). The Empire State Building shows how an alchemy of histories, from geography to transit and even an Astor family grudge, shaped the cityscape in ways that were logical and comprehensible, but wildly non-linear and with fascinating consequences.  

The Empire State Building is at the bottom of Murray Hill because that’s where the first Waldorf Astoria hotel was when it was a short, 10-block carriage ride to the Gilded Age city at 23rd Street in Madison Square along a flat, strollable Fifth Avenue. Okay, the Waldorf Astoria was where it was because that’s where two Astor brothers, their families and descendent sons (and cousins), lived as neighbors in roomy brownstones from the 1850s to the 1890s. The hotel came in two parts as the result of a family grudge; the Waldorf hotel replaced the home of one cousin to make the other’s homelife miserable, which was the impetus for the Astoria hotel to be built alongside and connected (when it came to money they did work together). But there’s a chance it could have happened anyway, their grandfather, John Jacob Astor, had done the same thing 60 years early downtown on Broadway across from City Hall with the neighborhood block he and his family had lived on for 30 years before redeveloping it has Astor House in 1836. 

So why did the Astors, who could live anywhere in Manhattan, chose to live at the bottom of a hill? Especially when their just as wealthy introverted social foils, the Wendells, lived at the top? Even high ground real estate follows the rules of location! location! location! The Wendells could keep the top of Murray Hill. The Croton Reservoir was right there, though not unpleasant it was a bulwark, and 42nd Street was a major crosstown thoroughfare and sometime cattle drive. The city’s social scene would be at the bottom of Murray Hill throughout most of the second half of the 19th century and beyond. 

So why was the Empire State Building built on the site of the Waldorf Astoria? It was a project blinded by such exuberance for the future (its builders believed the stock market would literally rise forever), it couldn’t see how fixed it was in the past. While 34th Street and Fifth Avenue was a fine location for an upscale hotel looking downtown to the Gilded Age city center, it was a different reality for later commuters, who were often oriented in the opposite direction, uptown, and uphill to Grand Central at the end of work every day for their commute home. The Empire State Building wouldn’t be a white collar office tower, its main early occupants were wholesale shoe-sellers and it’s more in the Garment District than the Midtown Business District.  

So why is there miles-long gap between the skyscrapers of Lower Manhattan and the Midtown Business District, including New York’s tallest-buildings-in-the-world which barely touch on it?

Through decades of near non-stop economic and population growth, New York’s two-part skyline was the product of timing, technology and transit. Otherwise, the natural laws of real estate development were at work guiding the builder to seek a property’s “highest and best use” in the determination of what was “legally permissible, physically possible, financially feasible, and maximally productive.”

A newspaper with an illustration of the elevated express.

General Research Division, The New York Public Library. “The Elevated Express” New York Public Library Digital Collections. Accessed February 5, 2025. https://digitalcollections.nypl.org/items/465dc0f0-5d6f-013d-bf87-0242ac110004

What made and sustained all uptown growth was a feedback loop between local rail transit: horsecar lines, elevated trains, and early subways, and ever-larger, uptown-moving business districts. There is virtually no trace of the first two rail systems that came and went on Manhattan, the subways of course continue. Interestingly, rail lines from decades earlier are still with us today in very different ways.

The first rail lines in Manhattan extended long distances “through the core and on the shore.” Their decendents are MetroNorth’s Harlem Line (from Grand Central) and The Highline elevated park, both are over the respective ruts and rails of the New York & Harlem (1831) and the Hudson River (1847) Railroads. Both lines carried passengers and freight. Later horsecars, elevated trains and subways were literally between the “core and shore” lines in time and space, and transported people only. 

The long, skinny shape of the Manhattan, and the fact “the city” started downtown, would have extraordinary ramifications for history and the city’s development. The “city,” by any definition, had no where to go but up. New York’s historic mass transit systems of horsecars, elevated trains and even the first subways were virtual straightaways running up and down 2nd, 3rd, 6th and 9th (or nearby adjacent) avenues. New transit came generationally, and it all worked together to do the same thing along a fixed column of rails: business districts formed at one end, and ever farther flung suburbs at the other. Successive transit systems ran along the surface, above, and then below the road; and channels of transit did not substitute, but supplemented one another in an effort to move families out of the city while some members “commuted” back to work.

By the daily act of going to work (technically these New Yorkers were not “commuters” who, by definition, hold discounted weekly or monthly passes) residents of neighborhoods like Hells Kitchen, San Juan Hill and Yorkville on the periphery provided the occupational workforce for the third wave of blue collar commercial business districts that moved uptown through the middle of Manhattan.

Transit was geo-spatially indexed in time and space to development through the central corridor such that, cast iron buildings in SoHo from the 1860s and 70s were predicated on the horse car lines of the 1850s, just as later steel-frame manufacturing loft buildings around Madison Square from the 1890s and 1900s were predicated on the elevated trains of the 1880s. As much as any force pushed or pulled the “city” uptown, the city was pumped uptown generationally by the daily act of going to work in ever larger, later, farther uptown business districts. 

Open Geometric Structure IV, 1990. Sol LeWitt. credit to https://MutualArt.com

The skyline slopes up from City Hall to Central Park! The artist Sol LeWitt represents the idea well with his minimalist work. Horizontal steel rails and ever-larger vertical cast iron and steel cage construction engaged in a feedback loop to build New York City; in Coney Island they bent the steel for rollercoasters!

Business districts progressed uptown in cast iron and ever-taller versions of steel frame because it always made more sense, at every point in time, for developers to look uptown to declining residential neighborhoods of brownstone home-turned-boardinghouse communities for redevelopment, rather then downtown to neighborhoods that were industrialized decades earlier; though buildings were obsolete, such districts were still going concerns. The alternative to uptown-advancing business districts is redevelopment in situ, which did happen along high volume and value channels like Broadway and Fifth Avenue; Broadway in SoHo is a remarkable of mix of brick, cast-iron, and steel frame buildings. Otherwise, business districts of advancing technologies are articulated in cast-iron and steel frame groupings (districts) going uptown through SoHo and Madison Square, generally west of Broadway and Fifth Avenue.  

Then too, there was a great railroad differentiation between the inter-city long distance rail lines “on the core and the shore,” and the local intra-city transit in between and on the periphery. As local rail systems saturated the periphery with redundant channels of transit, over the same period, rail travel through the central corridor retreated from development. The New York & Harlem Railroad removed from 27th Street in Madison Square in 1872 to 42nd Street with the first Grand Central Depot, facilitating commercial growth through the center.

So why didn’t the Midtown Business District form around the Met Life Building and the Empire State Building? Because at the time the Midtown Business District developed, Madison Square was already filled with decades-old steel frame  “state-of-the-art manufacturing loft buildings.” As well, Madison Square never had any good crosstown mass transit, whereas crosstown subways came to 14th, 42nd, and 53rd and even 59th Streets, in time for the Modern Era.

Image from the International Space Station