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Chicago had a grid system before the great fire, maybe NY is a good example of this but I do not know. See this[0] 1869 map which shows Chicago was already quite regularized

0: https://upload.wikimedia.org/wikipedia/commons/a/a8/1869_Bla...

It's not. The older parts of NYC are still not on a grid, there was no massive fire in NYC that needed to be rebuilt. They may have been thinking of London `¯\_(ツ)_/¯`

We've had a couple of big fires: https://en.wikipedia.org/wiki/Great_Boston_Fire

Somehow they didn't result in exchanging grids for winding streets.

The back bay, though, is newer than other parts of the city and it's a grid.

Re, Boston: The way I heard it was "Three rights make left, except in Boston."