So I wanted to break down a timeline for everyone to understand if Chicago has actually "lost ground" in the American Skyscraper race. While this only includes top ten data (trust me I know New York is churning out supertalls and this doesn't convey the totals as a city), it gives you an idea at how the general public would of understood where the tallest buildings in the country were located. And honestly, as for the top ten, Chicago is in a very similar situation that it has been in recent decades. But as we've said in this thread, Chicago blows other American cities away. And the past 50 years we've seen a two dog race. I Know this may not be the best thread to post this on, but since we're talking about this kinda stuff right now I'd figure I'd drop it here.
Moreover, like what Zapatan said, we represent the American Skyscraper. While I wish Chicago was neck and neck with New York, we both represent an American Icon and where it began. And like I said before, I think Chicago will grab a couple more of these seats back by 2030. But a 7:3 Ratio is probably expected. And honestly generous to Chicago considering New York has roughly 5 times the high rise count.
Also, the recurring buildings from decade to decade can give us insight to how the standings shook up. In 2020, only 4 buildings from 2010 are in the top ten. That's the lowest amount since 1930. America's top ten have been relatively constant, or took at least 20+ years to have shift around. This may explain why we feel shook up over how New York's skyline has rapidly changed. It's the roaring twenties all over again. But instead of art deco, it's skinny supertalls.
Also, ESB is a stud. He's like Babe Ruth and the Home Run Record. So far ahead of his time. It's amazing how ESB is still in the top ten, truly amazing.
For Comparison:
ESB is on 9 decades up until 2020
Chrysler was on 9 up until 2010
40 Wall St was on 6 up until 1980
Sears is on 5 up until 2020
Hancock is on 5 up until 2010
70 Pine St was on 5 up until 1980
Woolworth was on 5 up until 1960
The American Skyscraper
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1920
New York-6
Boston-1
Cincinnati-1
Hartford-1
Seattle-1

1920 by [url=https://www.flickr.com/photos/157979292@N05/]
1930
New York-8
Cleveland-1
Detroit-1
Recurring-2

1930 by [url=https://www.flickr.com/photos/157979292@N05/]
1940
New York-9
Cleveland-1
Recurring-5

1940 by [url=https://www.flickr.com/photos/157979292@N05/]
1950
New York-9
Cleveland-1
Recurring-10

1950 by [url=https://www.flickr.com/photos/157979292@N05/]
1960
New York-9
Cleveland-1
Recurring-9

1960 by [url=https://www.flickr.com/photos/157979292@N05/]
1970
New York-7
Chicago-2
Pittsburgh-1
Recurring-5

1970 by [url=https://www.flickr.com/photos/157979292@N05/]
1980
New York-7
Chicago-3
Recurring-5

1980 by [url=https://www.flickr.com/photos/157979292@N05/]
1990
Chicago-4
New York-4
Houston-1
Los Angeles-1
Recurring-7

1990 by [url=https://www.flickr.com/photos/157979292@N05/]
2000
Chicago-4
New York-4
Atlanta-1
Los Angeles-1
Recurring-9

2000 by [url=https://www.flickr.com/photos/157979292@N05/]
2010
Chicago-4
New York-4
Atlanta-1
Los Angeles-1
Recurring- 7

2010 by [url=https://www.flickr.com/photos/157979292@N05/]
2020
New York-7
Chicago-3
Recurring-4

2020 by [url=https://www.flickr.com/photos/157979292@N05/]