"New York City is f****d."

How would one get a category 4 hurricane on top of that perfidious City then?

Quoting from a professor of meteorology at SUNY-Stony Brook (state University on Long Island) "it's very, very unlikely, but not impossible". You'd need something like a path/speed of the Hurricane of 1938...or a scenario like the one I've described.
It may be unlikely...but it IS theoretically possible. Forecasters have screwed up before en masse.
 
How would one get a category 4 hurricane on top of that perfidious City then?


You don't, it's too far north; and why do you require Cat 4 vs a lower one?

If you want to maximum screw New York City, per the thread title: have a strong Cat 2 hit in the summer of 1977. The city was on the brink of financial collapse, the electrical grid was unstable (have the Blackout occur the day before, so people aren't warned the storm has changed course and is now headed straight for Manhattan; and so the Citicorp building's tuned mass damper is offline), and the Son of Sam is still out there.

Hurricane to City: "Drop Dead".
 
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How would one get a category 4 hurricane on top of that perfidious City then?
Hurricanes generally slow down as they intensify, remember that they don't do well with upper level shear like a jet stream. One with the proper setup hitting NYC could happen, and indeed, I forget if it was Irma or Maria last year, but for a few model runs, it was looking like a Cat 2-4 WAS going to hit NYC last year. On 9/11 of all days.
 
A worst case scenario is always very unlikely. Id propose for the op to weed out some of the major unnecessary improbabilities, but to stick with his premise. A major hurricane was expected to pass, but it changed course and gut the City.
So what to change. Move slower if it is big hurricane (yes, I want a story about a category 4, not something about to happen last year), a warning in place, but no evacuation orders (the hurricane is expected to pass).
Then when the outskirts are touching the shorelines, major power failures, the hurricane turns and the X hour evacuation warning just doesn’t reach people.
Now, very unlikely/unlucky, but not impossible and NYC is still very very F****D.
 
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