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I think most of the cities in upstate NY would thrive if they weren't in NY. I'm talking Buffalo, Rochester, and Albany. They all have walkable neighborhoods. Lots of great ethnic food. Strong working class/blue collar mentalities.
^This or just make some governmental structural changes.
St. Louis could have been more than it is but it intentionally shot itself in the foot when it became its own county making annexation of more land nearly impossible. The second major blow was disowning and deterioration of the Illinois side of the river. Complacency, inertia, and provincialism replaced the progressive stance that the place once had. Today St. Louis and Kansas City reside in one of the most backward states in the nation and a strong hostility has developed between urban and rural counties.
That being said, I enjoy visiting St. Louis probably more than any other major city and it has a fairly secure position as a middle-sized, robust, and historically significant American city. A century ago it was the fourth largest city in the US. Huge swaths of the old north side have now been cleared and are ready for new development. The city's infrastructure is already established for a place twice its present size.
I think this is the winner, so much so that a lot of people do not know where Cairo is LOL.
Philadelphia probably got hurt a bit by being between New York and Washington, although Baltimore and Wilmington have it worse because of Philadelphia! New Haven lost out to some extent to Hartford. Fort Worth and St Paul probably lost some potential due to they larger twin cities. And Milwaukee possibly missed some of her potential because of Chicago.
Another interesting example of lost potential might be the Norfolk/Hampton Roads area of Virginia. Don't get me wrong, I know the area is today developed and growing but with its great harbor and central location you would think the area might have become much larger then it is now.
Birmingham, AL is another candidate. In the first half of the 20th century, it was a peer to Atlanta; Atlanta decided to take a more progressive, business-friendly path and it has obviously reaped the benefits and left its former peer behind.
Los Angeles but for different reasons being discussed so far. It has a great setting and climate but ruined it by catering to the automobile. The built environment is pretty ugly overall and doesn't take advantage of the climate.
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