From the Malcolm Gladwell book Outliers "son when you leave New York City everywhere is Bridgeport" is not a literal statement. It's likely a figurative expression to emphasize that anywhere outside of the vibrant and unique environment of New York City might seem less exciting or notable in comparison for people who have grown accustomed to NYC life.
By the way, Bridgeport, Connecticut is a city located in Fairfield County, Connecticut. It's not actually bad.
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