Jeff Ruby hated the sleazy, scary New York of the past—but he hates the sterile, safe New York of today even more. Here, his angry rant against both Manhattans

In my first trip to Manhattan, a pigeon dropped a load on my dad’s shoulder, then flew off into Battery Park. It didn’t take an English major to see the symbolism there, especially for a dyed-in-the-wool Midwesterner like me, who hated New York before I could even spell it.

While traveling abroad during college, I once challenged an East Coast snob to draw a map of the United States, and he came up with an amorphous blob with nothing between Ohio and Nevada. (It looked eerily similar to that famous cover of The New Yorker that depicted Manhattan in great detail and everything west of Jersey crammed into a mostly barren rectangle. But my guy wasn’t trying to be funny.) When I mentioned that he’d forgotten a few states, he thought for a moment and then added Minnesota and Texas, their borders kissing somewhere near where Missouri should have been. I felt like my dad’s shoulder. With a single sketch, the kid had wiped 100 million Americans from existence—and fossilized my geographic prejudices for decades to come.

I hate New York
Illustration by Monika Melnychuk

As an angry young journalist years later, I pitched a Chicago–versus–New York feature for this publication: In impossibly clever ways, I would compare every important aspect of both cities, and after careful analysis (they suck; we rule) I would declare Chicago victorious. The boss gently said no. He explained that the Chicago-NYC face-off was one of the stalest themes in local journalism, this rah-rah stuff was amateurish, and any comparison could only devolve into dogmatic floundering about bagels and skyscrapers. I did not pitch another story for three years.

Fast forward to Oscar night, 2003: Chicago is up for Best Picture against Gangs of New York. When Rob Marshall’s sumptuous musical wins, I’m surprised to find myself thrilled, subconsciously identifying this as a victory for my city. The fact that it was filmed in Toronto was a mere asterisk on our triumph over the forces of evil. Up yours, Scorsese!

In the years that followed, when Chicago started winning everything else—the World Series, Top Chef, the presidency—the city around me began to affect a distinct swagger. I did not share its confidence. While everyone else in town was acting all cool, as though we’d had dozens of intellectual Hyde Parkers in the White House over the years, Chicago’s triumphs only peeled a scab off my neuroses. Somewhere in the afterglow of Obama’s election, I went on to find out when the last New Yorker was president (In your face, FDR?), then erased my laptop’s search history to hide my lingering feelings of inadequacy.

In post-Obama Chicago, though, I’m no longer allowed to hate New York. As a writer, a liberal, and a freethinking human, I am required to gaze lovingly toward Manhattan. And the New York–Chicago rivalry, at least outside of pizza message boards, is no longer acknowledged by anyone in either city. We’re all supposed to accept that these two complex cities—maddening and mesmerizing in their own special ways—are apples and onions. Are they equal? To ask the question is to mark yourself as a provincial twit, but I can’t just stop cold turkey.

On a recent trip to New York, I did my best to avoid making the inevitable urban comparisons, instead seeking out positives. My compliments tended to be halfhearted (“their street performers are pretty good” . . . “their stoplights are certainly well timed”), but baby steps were all I was capable of. For one lovely moment while crossing the Brooklyn Bridge, I surrendered to the city’s infectious vibe, and my rage faded into nothing more than the nagging suspicion that loathing an entire city based on little more than a pigeon and a map was just silly.

Philadelphia, though? The worst.

Photo credits for video