New York Metropolitan Vintage Photo Collection


120858 05 by nick dewolf photo archive, on Flickr

88-456 by nick dewolf photo archive, on Flickr

88-458 by nick dewolf photo archive, on Flickr

88-439 by nick dewolf photo archive, on Flickr


40 Wall was so dirty back then.

I wish they hadn’t torn down the National City Building. 48 Wall Street looks so alone without it


the wild west (today known as Hudson Yards)

aerial view of midtown manhattan looking northeast from hudson river april 1959 by eralsoto, on Flickr

world fair monorail

US NY NYC 1964 Worlds Fair Monorail - Steve Zabel Collection (23914) by David Pirmann, on Flickr


Some infamous ex-landmarks, (ironically doomed because of the lack of said status)

Singer Building, somewhere between 1948 and 1964

World Building, between 1950 and 1955

Tribune Building, sometime before 1955

Tribune Building 1959

World Building demolition, 1955

Tribune Building demolition, 1966

Singer Building demolition, October 1967




Battery Tunnel exit in 1955. Notice the four 1800s era buildings being demolished on the right: they were gone by 1956 and replaced by the sinful annex to that parking garage that we love so much today


Seagram Building not long after completion

Union Carbide Building not long after completion

The thing that intrigues me is the fact that many old buildings around them were demolished not long after the photo was taken and replaced by generic ugly boxes: the pictures depict the short time when boxes like these on or near Park Ave were new, rare and incredible.


These were the nice boxes. The soul crushers like the WTC and XYZ buildings came later. Less and less glass until post modernism burst into the skyline. Luckily next to no brutalist skyscrapers were constructed in Manhattan.


Agreed there. I liked the WTC for a few reasons but none of them were the design, same with the XYZ towers. Leave just one of them and we’d all be as soulless as they are. I tend to hate the 50s Emery buildings and like or ignore the larger later SOM 60s ones (though I despise 1 Liberty Plaza) but that’s just me.


I think the biggest issue with 1 Liberty is that it replaced the Singer Building, which was a triumph of design. Although as I understand it, part of the decision making behind demolition was that the Singer couldn’t realistically be updated for modern office use. Not defending that stance btw, just saying what I’ve read


From Library of Congress


I find steel facade skyscrapers incredibly aesthetically pleasing (at least from the outside), so I don’t really share the vitriol some express regarding 1 Liberty Plaza replacing the Singer Building. Would I still take its predecessors over it? yeah, probably.

IMG_9727.JPG by josh s jackson, on Flickr


Yea I agree, I don’t mind 1 Liberty Plaza and actually like the design (compared to postmodern stuff).

What gets me though is that the Singer Building was surrounded by dozens of 3,4,5 story ugly buildings (some still exist today). Why would the developer go through the hassle of buying a huge building only to demolish is when there were plenty of other lots around with less than spectacular buildings.

Was buying one large building with a big footprint and tearing it down really that much easier than trying to acquire a group of small ugly buildings? The economics just dont add up to me unless they got a crazy good deal on the Singer Building (or if people who built 1 Liberty already owned the Singer).


I personally don’t like it. I prefer more slim, smooth and sleek towers, but it has the exterior steel skeleton and looks shabby to me. Not to mention when they need to paint it. But that’s my opinion.

I hate that not only did they tear down my favorite building and an iconic building of the city’s history (not even mentioning 165 Broadway next door) but the park added to the loss:

and the tallest removed for the park

while literally a block away…

I’m pretty sure that these parcels near the corner, as well as the buildings on the site of 22 Cortlandt Street and the savings bank were for sale as well, adding insult to injury.


Yea that to me is what I just don’t understand. There are so many ugly small buildings from that era that are still around to this day. Why on earth would you tear down on of the tallest buildings in the world when there were so many other lots right nearby? I have tried to figure that question out for years now.

The only thing I can come up with is that the owners of those small buildings didn’t want to sell or that it was too complex to acquire enough small buildings to create a big enough footprint. But still, one of the tallest buildings in the world… why???


From what I understand it was denied landmark status because finding a buyer would be tough… if I recall correctly this thought came from the experience of the Jerome Mansion being demolished because of no buyers, but I’m fairly sure that a 47 story skyscraper would have a chance of finding a buyer compared to a 4 story mansion.

Also, going by the tallest building order circa 1967:

1: 70 Pine Street
2: 40 Wall Street
3: Chase Manhattan Plaza
4: Woolworth Building
5: 20 Exchange Place
6: Marine Midland Building
7: 1 Wall Street
8: Home Insurance Building

Singer would come next. When it came down it was the 9th tallest building in all of downtown.

Just why?


While we’re on this discussion, has some good footage of downtown in September 1967. As seen below are the massive beasts that once were 165 Broadway and the Singer Building, Being it was September, there was a situation, safely said…


That’s great old footage! One of those clips got me thinking.

I’m a huge fan of the Woolworth building and the modern building that sits right next to it seems kinda tiny. There are actually a bunch of those buildings throughout the city that were built in the 50/60’s that arn’t really that tall. To me those are some of the ugliest in the city and they don’t seem to be maximizing the space like they could.

I wonder if those will ever be replaced with supertalls? They have large footprints but are short. To me those are prime properties to be redeveloped. Heck if they did it with the Singer, why not do it with an ugly building using the same logic :slight_smile:


I’ve been expecting that too. I think this will start with midtown since midtown has jesus-style zoning and can sprout buildings up like it has been, but downtown will probably have a supertall boom too and these things will die a hard death.

1 Whitehall Street is a twin of that minus maybe 2 floors. That should go too.


There are a couple on Wall Street which I hoped would eventually get redeveloped sine they weren’t that tall but I think one was just converted into condos. SMH

I hope that doesn’t happen with more because converting all those old buildings into condos seems to be the going trend. Like the Woolworth I think thy just turned the Tribune Tower in Chicago into condos. Let’s just hope they don’t do it with 50’s/60’s garbage.